CAST HETEROCYCLIC COMPOUND, PEST CONTROL AGENT AND METHOD FOR PEST CONTROL

专利摘要:
the present invention relates to obtaining a fused heterocyclic compound represented by the formula (1) below, presenting excellent pest control, where a1 represents nr5 or similar, a2 and a3 represent a nitrogen atom or similar, r1 represents a hydrocarbon group c1 to c6 or similar, r2 represents a hydrocarbon group of c1 to c6 or similar, r3 and r4 are the same or different and represent a hydrocarbon group of c1 to c6 or similar, n represents 0, 1 or 2 and g any of the following formulas, (g1) (g2) (g3) (g4) (g5) (g6) (g7), where q represents an oxygen atom or similar, p represents 0 or 1 and r10 to r24 are the same or different, and represent a c1 to c6 chain hydrocarbon group, or the like.
公开号:BR112015032689B1
申请号:R112015032689-7
申请日:2014-06-25
公开日:2020-03-10
发明作者:Takamasa Tanabe；Hajime Mizuno；Ayaka TANAKA；Shinya Nishimura；Yoshihiko Nokura
申请人:Sumitomo Chemical Company, Limited；
IPC主号:

专利说明:

Descriptive Report of the Invention Patent for "Fused HETEROCYCLIC COMPOUND, PEST CONTROL AGENT AND METHOD FOR PEST CONTROL".
TECHNICAL FIELD
[0001] The present invention relates to a certain type of a fused heterocyclic compound and its use in pest control.
BACKGROUND TECHNIQUE
[0002] So far, for the purpose of pest control, several compounds have been studied and used in practice. In addition, a certain type of a fused heterocyclic compound (for example, see Patent Document 1) is known.
BACKGROUND DOCUMENT
PATENT DOCUMENT
[0003] Patent Document 1: WO2013 / 018928 SUMMARY OF THE INVENTION
PROBLEMS TO BE SOLVED BY THE INVENTION
[0004] It is an object of the present invention to provide a compound that has an excellent pest control effect and a method for controlling pests using the compound.
MEANS TO SOLVE THE PROBLEMS
[0005] As a result of an intensive study to solve the above problem, the present inventors found that a fused heterocyclic compound, represented by the formula (1) below, has an excellent pest control effect and, thus, achieves the present invention.
[0006] More specifically, the present invention is as described below.
[1] A fused heterocyclic compound represented by formula (1): where A1 represents NR5, an oxygen atom or a sulfur atom, A2 represents a nitrogen atom or CR6, A3 represents a nitrogen atom or CR7, R1 represents a C1 to C6 hydrocarbon group, optionally with one or more atoms or groups selected from the U group or an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the V group, R2 represents a C1 chain hydrocarbon group to C6 optionally with one or more atoms or groups selected from the group U, a phenyl group optionally with one or more atoms or groups selected from the group W, a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the group W, OR8, S (O) mR8, S (O) 2NR8R9, NR8R9, NR8CO2R9, NR8C (O) R9, CO2R8, C (O) R8, C (O) NR8R9, SF5, a cyan group, a nitro group, a halogen atom or a hydrogen atom, G represents a group represented by the G1 group, G2 group, G3 group, G4 group, G5 group, G6 group or G7 group of the following formulas: where Q represents an oxygen atom or a sulfur atom, p represents 0 or 1, R10 represents a hydrocarbon group C1 to C6 optionally having one or more atoms or groups selected from the group U, a phenyl group optionally having one or more atoms or groups selected from the group W, a hydrogen atom, a hydrocarbon group from chain C1 to C6 with one or more atoms or groups selected from group Z, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a heterocyclic group of 4, 5 or 6 members, optionally with one or more atoms or groups selected from the group W, CO2R8, C (O) R8 or C (O) NR8R9, R11 represents R25, R26, OR27, OR28, SR29, NR30R31 or C (O) R32, where R25 represents a C1 to C6 hydrocarbon group with one or more atoms or groups selected from the group Z, a group alicyclic hydrocarbon C3 to C9, optionally with one or more atoms or groups selected from group V, or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from group W; R26 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the U group, a phenyl group optionally with one or more atoms or groups selected from the W group or a hydrogen atom; R27 represents a C1 to C6 hydrocarbon group with one or more atoms or groups selected from the group Z, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W; R28 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the U group, a phenyl group optionally with one or more atoms or groups selected from the W group or a hydrogen atom; R29 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the W group, a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the W group or a hydrogen atom; R30 and R31 are the same or different and represent a chain hydrocarbon group C1 to C6, optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9, optionally with one or more atoms or groups selected group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, SO2R8, CO2R8, C (O ) R8 or a hydrogen atom; and R32 represents a chain hydrocarbon group C1 to C6, optionally with one or more atoms or groups selected from the group Y, OR8, NR8R9 or a hydrogen atom, when R11 represents R25, OR27, SR29, NR30R31 or C (O) R32 , R10 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the U group, a phenyl group optionally with one or more atoms or groups selected from the W group, a hydrogen atom, a chain hydrocarbon group C1 to C6 with one or more atoms or groups selected from the group Z, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a heterocyclic group of 4, 5 or 6 members, optionally with one or more atoms or groups selected from the group W, CO2R8, C (O) R8 or C (O) NR8R9, when R11 represents R26 or OR28, R10 represents a chain hydrocarbon group C1 to C6 with one or more atoms or groups selected from the group Z, a hydr group the alicyclic carbon from C3 to C9, optionally with one or more atoms or groups selected from group V, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from group W, CO2R8, C (O ) R8 or C (O) NR8R9, R12 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, a hydrogen atom, SO2R8, CO2R8, C (O) R8 or C (O) NR8R9, R13 represents R33, where R33 represents a C1 to C6 hydrocarbon group optionally with one or more atoms or groups selected from the Y group, a C3 to C9 alicyclic hydrocarbon group optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the group W or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, OR34, where R34 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the W group, a 4, 5 or 6 membered heterocyclic group optionally with one or more atoms or groups selected from the W group, or a hydrogen atom, or NR35R36, where R35 and R36 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms u groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W or a hydrogen atom , R14 and R15 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V , a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, a hydrogen atom, SO2R8, CO2R8 , C (O) R8 or C (O) NR8R9, R16 represents R37, where R37 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicylic hydrocarbon group I click C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a 4, 5 or 6 membered heterocyclic group optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, C (O) R38, where R38 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, or CO2R39, where R39 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C 3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, C (O) SR40, where R40 represents an optionally hydrocarbon group C1 to C6 with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W , C (O) NR41R42, where R41 and R42 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group o C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, SO2R43, where R43 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, S ( O) 2OR44, where R44 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the Y group, a C3 to C9 alicyclic hydrocarbon group optionally with one or m atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or S (O) 2NR45R46, where R45 and R46 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or an atom of hydrogen, R17 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms s or groups selected from group V, a phenyl group optionally having one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, an atom of hydrogen, SO2R8, CO2R8, C (O) R8 or C (O) NR8R9, R18 represents R47, where R47 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from group Y, a hydrocarbon group alicyclic C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, C (Q) R48, where R48 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 op optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, C (Q) OR49, where R49 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, or C (Q) NR50R51, where R50 and R51 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, a hydr group alicyclic carbon C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, R19 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the group Y, a C3 to C9 alicyclic hydrocarbon group optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from group W, a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from group W, or a hydrogen atom, R20 represents R52, where R52 represents a C1 to C6 hydrocarbon group optionally with one or more atoms or groups selected from the Y group, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, OR53, where R53 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the group Y, a C3 to C9 alicyclic hydrocarbon group optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the group W or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or NR54R55, where R54 and R55 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group single C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, R21 and R22 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the groups selected from group W, R23 represents a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected of the group W, or a hydrogen atom, R24 represents a chain hydrocarbon group C1 to C6 with one or more atoms or groups selected from the group Z, an alicyclic hydrocarbon group from C3 to C9, optionally with one or more atoms or groups selected group V, a 4, 5 or 6 membered heterocyclic group optionally with one or more atoms or groups selected from the group W, R3 and R4 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the U group, a phenyl group optionally with one or more atoms or groups selected from the W group, a 5- or 6-membered heterocyclic group optionally with one or more atoms or group are selected from the group W, OR8, S (O) mR8, S (O) 2NR8R9, NR8R9, NR8CO2R9, NR8C (O) R9, CO2R8, C (O) R8, C (O) NR8R9, SF5, a cyan group, a nitro group, a halogen atom or a hydrogen atom, or R3 and R4, together with the carbon atoms to which they are attached, form a benzene ring, optionally with one or more atoms or groups selected from the W group, a 5 or 6-membered heterocyclic ring, optionally with one or more atoms or groups selected from the group W or a 5, 6, 7 or 8-member non-aromatic ring optionally with one or more atoms or groups selected from the group V, R5 represents a C1 to C6 chain hydrocarbon group, optionally with one or more atoms or groups selected from the X group, a C1 to C6 chain hydrocarbon group with a phenyl group, wherein the phenyl group optionally has one or more atoms or groups selected from the W group, a C1 to C6 chain hydrocarbon group with a 5- or 6-membered heterocyclic group, in which het group erocyclic 5 or 6 member optionally has one or more atoms or groups selected from the group W, CO2R8, C (O) R8, an alicyclic hydroarbonide group from C3 to C9 optionally with one or more atoms or groups selected from the group V, or a hydrogen atom, R6 and R7 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more halogen atoms, OR8, S (O) mR8, NR8R9, CO2R8, C (O) R8, a cyano group, a nitro group, a halogen atom or a hydrogen atom, R8 and R9 are the same or different and represent a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the Y group, a group alicyclic hydrocarbon C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups select group W, or a hydrogen atom, and each m independently represents 0, 1 or 2, and n represents 0, 1 or 2, and when m is 1 or 2 in S (O) mR8, R8 does not represent an atom hydrogen;
Group U: a group consisting of C1 to C6 alkoxy groups, optionally with one or more halogen atoms, C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more atoms halogen groups, C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfinyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally with one or more halogen atoms, C2 alkylcarbonyl groups to C6 optionally with one or more halogen atoms, C2 to C6 alkoxycarbonyl group optionally with one or more halogen atoms, C3 to C9 cycloalkyl groups optionally with one or more halogen atoms or one or more C1 to C3 alkyl groups, cyano groups, hydroxy groups and halogen atoms, Group V: a group consisting of C1 to C6 chain hydrocarbon groups, optionally with one or more halogen atoms, alkoxy groups i C1 to C6 optionally with one or more halogen atoms, C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more halogen atoms, and halogen atoms, Group W: one group consisting of C1 to C6 chain hydrocarbon groups optionally with one or more halogen atoms, C1 to C6 alkoxy groups optionally with one or more halogen atoms, C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms, alkylsulfinyl groups C1 to C6 optionally with one or more halogen atoms, alkylsulfonyl groups C1 to C6 optionally with one or more halogen atoms, alkyl-mino groups C1 to C6 optionally with one or more halogen atoms, dialkylamino groups C2 to C8 optionally with one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally with one or more halogen atoms, C2 to C6 alkoxycarbonyl groups optionally with one or more s halogen atoms, halogen groups, cyano groups and nitro groups, Group X: a group consisting of C3 to C9 cycloalkyl groups, optionally with one or more halogen atoms, C1 to C6 alkoxy groups optionally with one or more atoms halogen, C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more halogen atoms, C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfinyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally with one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally with one or more halogen atoms, C2 to C6 alkoxycarbonyl group optionally with one or more atoms halogen, hydroxy groups, halogen atoms and cyano groups, Group Y: a group consisting of alicyclic hydrocarbon groups C3 to C9 optionally with one or more s atoms or groups selected from group V, C1 to C6 alkoxy groups optionally with one or more halogen atoms, C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more halogen atoms , C1 to C6 alkylsulphyl groups optionally with one or more halogen atoms, C1 to C6, C1 to C6 alkylsulfinyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally with one or more halogen atoms, groups alkylaminosulfonyl C1 to C6 optionally with one or more halogen atoms, dialkylaminosulfonyl groups C2 to C8 optionally with one or more halogen atoms, alkylamino groups C1 to C6 optionally, with one or more halogen atoms, dialkylamino groups C2 to C8 optionally with one or more halogen atoms, C2 to C6 alkylcarbonylamino groups optionally with one or more halogen atoms, C2 to alkoxycarbonylamino groups C6 optionally with one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally with one or more halogen atoms, C2 to C6 alkoxycarbonyl groups optionally having one or more halogen atoms, C2 to C6 alkylamino carbonyl groups optionally with one or more halogen atoms, C3 to C10 dialkylaminocarbonyl groups optionally with one or more halogen atoms, cyano groups, hydroxy groups and halogen atoms, Group Z: a group consisting of phenyl groups, optionally with one or more atoms or groups selected from the group W, heterocyclic groups with 4, 5 or 6 members, optionally with one or more atoms or groups selected from the group W, alkyl-mino groups C1 to C6 optionally with one or more halogen atoms, dialkylamino groups C2 to C8 optionally with one or more halogen atoms, C2 to C6 alkylcarbonylamino groups optionally with one or more halogen atoms, C2 to C6 alkoxycarbonylamino groups optionally with one or more halogen atoms, C2 to C6 alkyl minocarbonyl groups optionally with one or more halogen atoms and C3 to C10 dialkylaminocarbonyl groups optionally with one or more halogen atoms, or an N-oxide thereof (hereinafter, the fused heterocyclic compound represented by formula (1) and its N-oxide are referred to as the compound of the present invention).
[2] A compound according to [1], in which R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group has , optionally, one or more halogen atoms or one or more C1 to C3 alkyl groups, a C2 to C6 alkenyl group optionally with one or more halogen atoms, an C2 to C6 alkynyl group optionally with one or more halogen atoms, or a C3 to C6 cycloalkyl group optionally with one or more atoms or groups selected from the group consisting of halogen atoms and C1 to C6 alkyl groups, optionally with one or more halogen atoms, R2 is a halogen atom or a hydrogen atom, R3 and R4 are the same or different and are a hydrocarbon group of chains C1 to C6 optionally with one or more atoms or groups selected from the group U, OR8, S (O) mR8, a halogen atom or an atom of hydrogen, and R5 is a group hydrocarbon chain C1 to C6, optionally with one or more atoms or groups selected from the group X, CO2R8, C (O) R8, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, or a hydrogen atom.
[3] Compound, according to [1] or [2], where A1 is NR5.
[4] A compound according to [1] or [2], where A1 is an oxygen atom.
[5] A compound according to [1] or [2], where A1 is a sulfur atom.
[6] A compound, according to any one of [1] to [5], where A2 is CR6 and A3 is a nitrogen atom.
[7] Compound, according to any one of [1] to [5], where A2 is CR6 and A3 is CR7.
[8] Compound, according to any one of [1] to [7], where G is the G1 group.
[9] Compound, according to any one of [1] to [7], where G is the group G2.
[10] Compound, according to any one of [1] to [7], where G is the group G3.
[11] Compound, according to any one of [1] to [7], where G is the group G4.
[12] Compound, according to any one of [1] to [7], where G is the group G5.
[13] Compound, according to any one of [1] to [7], where G is the group G6.
[14] Compound, according to any one of [1] to [7], where G is the group G7.
[15] Compound, according to any one of [1] to [7], where G is the G1 group, and R11 is R25, OR27, SR29, NR30R31 or C (O) R32.
[16] Compound, according to any one of [1] to [7], where G is the G1 group, and R11 is R26 or OR28.
[17] A compound represented by formula (1A), where the symbols represent the same meaning as in formula (1).
[18] A compound represented by formula (1B), where the symbols represent the same meaning as in formula (1).
[19] A compound represented by the formula (1C), where the symbols represent the same meaning as in the formula (1).
[20] Pest control agent, which comprises the compound as defined in any one of [1] to [19], and an inert vehicle.
[21] A method of controlling pests, comprising applying an effective amount of the compound, as defined in any one from [1] to [19], to a pest or pest infested area. MODE FOR CARRYING OUT THE INVENTION
[0007] The groups used in the description of this descriptive report will be described below with the examples. The. The "halogen atom" in this invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
[0008] The "C1 to C6 hydrocarbon group" in that invention represents a C1 to C6 alkyl group, a C2 to C6 alkenyl group and a C2 to C6 alkynyl group.
[0009] Examples of the "C1 to C6 alkyl group" in that invention include C1 to C6 alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec- butyl, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group and the like. Examples of the "C2 to C6 alkenyl group" in that invention include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group and the like.
[0010] Examples of the "C2 to C6 alkynyl group" in that invention include an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group and the like. [0011] The notation of "chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group" U "in that invention represents a straight chain or branched chain hydrocarbon group comprising a number of carbon atoms of 1 to 6, in which a hydrogen atom attached to the carbon atom is optionally substituted by an atom or group selected from the U group, and that at that moment, having two or more atoms or groups selected from the U group, the atoms or groups selected of the U group can be the same or different from each other. Examples of the "C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the U group" include C1 to C6 alkyl groups, optionally with one or more atoms or groups selected from the U group as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a ne-opentyl group, a hexyl group, a methoxymethyl group, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, a tert-butyloxime-tila group, a 2-methoxyethyl group , a 2-ethoxyethyl group, a 2-pro-piloxyethyl group, a 2-isopropyloxyethyl group, a 2-butyloxyethyl group, a 2-sec-butyloxyethyl group, a 2-tert-butyloxyethyl group, a trifluoro-methyl group, a trichloromethyl group, a 2-fluorethyl group, a 2,2-difluorethyl group, a 2,2,2-trifluorethyl group, a pentafluorethyl group, a 2- (methylsulfanyl) ethyl group, a 2- (ethylsulfanyl) ethyl group, a 2- (methylsulfinyl) ethyl group, a 2- (methylsulfonyl) ethyl group, a 2-hydroxyethyl group, a cyclopropylmethyl group, a 1-methylcyclopropylmethyl group and a 2,2-difluorocyclopropylmethyl group;
[0012] C2 to C6 alkenyl groups, optionally with one or more atoms or groups selected from the U group as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl- 1-propenyl, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoralyl group and a pentafluoralyl group; and C2 to C6 alkynyl groups optionally with one or more atoms or groups selected from the U group, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1- group hexynyl and a 4,4,4-trifluor-2-butynyl group. [0013] The notation "chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group" X "in that invention represents a straight chain or branched chain hydrocarbon group comprising a number of carbon atoms of 1 to 6, in which a hydrogen atom attached to the carbon atom is optionally substituted by an atom or group selected from group X, and that at that moment, having two or more atoms or groups selected from group X, the atoms or groups selected group X may be the same or different from each other.
[0014] Examples of the "C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the X group" include C1 to C6 alkyl groups, optionally with one or more atoms or groups selected from the X group as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a methoxymethyl group, a group ethoxymethyl, a propyloxymethyl group, an isopropyl-loxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, a tert-butyloxymethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-propyloxyethyl group, a 2- group isopropyloxyethyl, a 2-bu-tiloxyethyl group, a 2-sec-butyloxyethyl group, a 2-tert-butyloxyethyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluorethyl group, a 2,2-difluorethyl group, a group 2,2,2-trifluorethyl, a pentafluo-retila group, a 2- (methylsu lfanyl) ethyl, a 2- (ethylsulfanyl) ethyl group, a 2- (methylsulfinyl) ethyl group, a 2- (methylsulfonylethyl) group, a 2-hi-droxyethyl group, a cyclopropylmethyl group, a 1-methylcyclopropylme-tila group, a 2,2-difluorcyclopropylmethyl group, a phenylmethyl group, a 4-chlorophenylmethyl group, a 4-trifluormethylphenylmethyl group, a tetrahydrofuran-2-ylmethyl group, a tetrahydropyran-2-ylmethyl group, a tetrahydropyran-3 group -ylmethyl, a thiazol-5-ylmethyl group, a 2-clo-rotiazol-5-ylmethyl group, a pyridin-3-ylmethyl group, a 6-chloropyridin-3-ylmethyl group and a 6-trifluormethylpyridin-3-ylmethyl group ;
C2 to C6 alkenyl groups, optionally with one or more atoms or groups selected from group X as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group , a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoralyl group and a pentafluoralyl group; and C2 to C6 alkynyl groups optionally with one or more atoms or groups selected from the X group, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1- group hexynyl and a 4,4,4-trifluor-2-butynyl group. [0015] The notation of "chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group" Y "in that invention represents a straight chain or branched chain hydrocarbon group comprising a number of carbon atoms of 1 to 6, in which a hydrogen atom attached to the carbon atom is optionally substituted by an atom or group selected from group Y, and that at that moment, having two or more atoms or groups selected from group Y, the atoms or groups selected group Y may be the same or different from each other. Examples of the "C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from group Y" include C1 to C6 alkyl groups, optionally with one or more atoms or groups selected group Y as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a g neopentyl group, a hexyl group, a methoxymethyl group, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, a tert-butyloxymethyl group, a 2-methoxyethyl group, a 2-methoxyethyl group 2-ethoxyethyl group, a 2-propyloxyethyl group, a 2-isopropyloxyethyl group, a 2-butyloxyethyl group, a 2-sec-bu-tilyloxyethyl group, a 2-tert-butyloxyethyl group, a trifluoromethyl group, a trichloromethyl group, a trichloromethyl group 2-fluorethyl group, a 2,2-difluorethyl group, a 2,2,2-trifluorethyl group, a pentafluorethyl group, a 2- (methylsulfanyl) ethyl group, a 2- (ethylsulfanyl) ethyl group, a 2 group - (methylsulfinyl) ethyl, a 2- (methylsulfonylethyl) group, a 2-hydroxyethyl group, a cyclopropylmethyl group, a 1-methylcyclopropylmethyl group, a 2,2-difluorci-clopropylmethyl group, a phenylmethyl group, a 4- group chlorophenylmethyl, a 4-trifluormethylphenylmethyl group, a tetrahydrofuran-2-ylmethyl group, a tetrahydropyran-2-ylmethyl group, a group tetrahydropyran-3-ylmethyl, a thiazol-5-ylmethyl group, a 2-chlorothiazol-5-ylmethyl group, a pyridin-3-ylmethyl group, a 6-chloropyridin-3-ylmethyl group and a 6-tri group -fluormethylpyridin-3-ylmethyl;
C2 to C6 alkenyl groups, optionally with one or more atoms or groups selected from the β group as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group , a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoralyl group and a pentafluoralyl group; and C2 to C6 alkynyl groups optionally with one or more atoms or groups selected from the Y group, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a group 1- hexynyl and a 4,4,4-trifluor-2-butynyl group. [0016] The notation of "C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the group" Z "in that invention represents a straight chain or branched chain hydrocarbon group comprising a number of carbon atoms of 1 to 6, in which a hydrogen atom attached to the carbon atom is optionally replaced by an atom or group selected from the group Z, and that at that moment, having two or more atoms or groups selected from the group Z, the atoms or groups selected of the Z group can be the same or different from each other. Examples of the "C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the Z group" include C1 to C6 alkyl groups, optionally with one or more atoms or groups selected group Z as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a g ne-opentyl group, a hexyl group, a cyclopropylmethyl group, a 1-me-tilcyclopropylmethyl group, a 2,2-difluorcyclopropylmethyl group, a fe-nilmethyl group, a 4-chlorophenylmethyl group, a 4-trifluormethylphenyl-methyl group, tetrahydrofuran-2-ylmethyl group, a tetrahydropyran-2-ylmethyl group, a tetrahydropyran-3-ylmethyl group, a thiazol-5-ylmeyl group, a 2-chlorothiazole-5-ylmethyl group, a pyridin-3-ylmethyl group, a 6-chloropyridin-3-ylmethyl group, a 6-trifluormethylpyridin-3-ylmethyl group, a 2- (methylamino) ethyl group, a 2- (dimethylamino) ethyl group, a 2- ( acetylaminocarbonyl) ethyl, a 2- (methoxycarbonylamino) ethyl group, a 2- (methylaminocarbonyl) ethyl group and a 2- (dimethylaminocarbonyl) ethyl group;
C2 to C6 alkenyl groups, optionally with one or more atoms or groups selected from the Z group as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group , a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 2-cyclopropyl vinyl group, a 2-phenyl vinyl group, a 3-phenyl-2 group -propenyl, a 2- (pyridin-3-yl) vinyl group and a 3- (dimethylamino) -2-propenyl group; and C2 to C6 alkynyl groups optionally with one or more atoms or groups selected from the Z group, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1- group hexynyl, a 2-phenylethynyl group and a 2- (pyridin-3-yl) ethynyl group.
[0017] Examples of the "C1 to C6 chain hydrocarbon group optionally with one or more halogen atoms" in that invention include C1 to C6 alkyl groups, optionally with one or more halogen atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a ne-opentyl group, a hexyl group, a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a trichloromethyl group, a 2-fluorethyl group, a 2-chloroethyl group, a 2- group bromoethyl, a 2,2-difluorethyl group, a 2,2,2-trifluorethyl group, a pentafluorethyl group, a heptafluorpropyl group and a heptafluorisopropyl group;
C2 to C6 alkenyl groups, optionally with one or more halogen atoms, such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoralyl group and a pentafluoralyl group; and C2 to C6 alkynyl groups optionally with one or more halogen atoms, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group and a group 4,4,4-trifluor-2-butynyl.
[0018] Examples of the "C1 to C6 alkyl group optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, wherein the cyclopropyl group optionally has one or more halogen atoms or one or more alkyl groups C1 to C3 "in this invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group , a hexyl group, a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a triclo-romethyl group, a group 2 -fluorethyl, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluorethyl group, a 2,2,2 group, -trifluorethyl, a pentafluorethyl group, a heptafluorpropyl group, a heptafluo-risopropyl group, a group cyclopropi lmethyl, a 2-cyclopropylethyl group, a 1-cyclopropylethyl group and the like.
[0019] Examples of the "C1 to C6 alkyl group optionally with one or more halogen atoms" in that invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a fluoromethyl group, a chloromethyl group, a bromomethyl group, an io-domethyl group, a difluoromethyl group, a dichloromethyl group , a tri-fluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a trichloromethyl group, a 2-fluorethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluorethyl group, a 2,2 group , 2-triflu-orethyl, a pentafluorethyl group, a heptafluorpropyl group and a heptafluorisopropyl group, and the like.
[0020] Examples of the "C1 to C6 chain hydrocarbon group with a phenyl group, wherein the phenyl group may have one or more atoms or groups selected from the W group" in that invention include a phenylmethyl group, a 4-chlorophenylmethyl group, a 4-trifluormethylphenyl-methyl group and the like. At that time, having two or more atoms or groups selected from the W group, the atoms or groups selected from the W group can be the same or different from each other.
[0021] Examples of the "C1 to C6 chain hydrocarbon group with a 5- or 6-membered heterocyclic group, wherein the 5- or 6-membered heterocyclic group may have one or more atoms or groups selected from the W group" therein The invention includes a tetrahydrofuran-2-ylmethyl group, a tetrahydropyran-2-ylmethyl group and a tetrahydropyran-3-ylmethyl group, a thiozol-5-ylmethyl group, a 2-chloro-thiozol-5- group ilmethyl, a pyridin-3-ylmethyl group, a 6-chloropyridin-3-ylmethyl group, a 6-trifluormethylpyridin-3-ylmethyl group and the like. At that time, having two or more atoms or groups selected from the W group, the atoms or groups selected from the W group can be the same or different from each other. Examples of "C2 to C6 alkenyl group optionally with one or more halogen atoms" in this invention include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl group 1-propenyl, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoralyl group and a pentafluoralyl group, and the like.
[0022] Examples of the "C2 to C6 alkynyl group optionally with one or more halogen atoms" in that invention include an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a group 1-hexynyl, a group 4,4,4-trifluor-2-butynyl and the like.
[0023] The notation "alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V" in that invention represents a cyclic non-aromatic hydrocarbon group comprising a number of carbon atoms from 3 to 9, wherein one hydrogen atom attached to the carbon atom is optionally substituted by an atom or group selected from group V, and that at that moment, having two or more atoms or groups selected from group V, the atoms or groups selected from group V can be the same or different from each other. Examples of the "C3 to C9 alicyclic hydrocarbon-grouping group optionally with one or more atoms or groups selected from the V group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group , a cyclooctyl group, a cyclononanyl group, a 1-cyclohexenyl group, a 2-cyclohexenyl group, a 3-cyclohexenyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group , a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2-methoxy-cyclohexyl group, a 3-methoxy-cyclohexyl group, a 4-methoxy-cyclohexyl group, a 1-fluorocyclohexyl group, a 2-fluorocyclohexyl group, a 3-fluorocyclohexyl group and a 4-fluorocyclohexyl group.
[0024] Examples of the "C3 to C6 cycloalkyl group" in that invention include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.
[0025] Examples of the "C3 to C6 cycloalkyl group optionally with one or more atoms or groups selected from the group consisting of halogen atoms and C1 to C6 alkyl groups, optionally with one or more halogen atoms" in this invention include a cyclic group clopropyl, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 1-fluorocyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2-dibromocyclopropyl group, a cyclobutyl group, a group cyclopentyl and a cyclohexyl group.
[0026] Examples of the "C3 to C9 cycloalkyl groups optionally with one or more halogen atoms" in that invention include a cyclopropyl group, a 1-fluorocyclopropyl group, a 2,2-difluorci-clopropyl group, a 2,2-dichlorocyclopropyl group , a 2,2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.
[0027] Examples of "C3 to C9 cycloalkyl groups optionally with one or more halogen atoms or one or more C1 to C3 alkyl groups" in that invention include a cyclopropyl group, a 1-me-methylcyclopropyl group, a 2-dimethylcyclopropyl group, a 1-fluorocyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group. The notation of "phenyl group optionally with one or more atoms or groups selected from the group W" in this invention represents a phenyl group in which a hydrogen atom of the phenyl group is optionally substituted by an atom or group selected from the group W, and that in that At the moment, having two or more atoms or groups selected from the W group, the atoms or groups selected from the W group can be the same or different from each other.
[0028] Examples of the "phenyl group optionally with one or more atoms or groups selected from the W group" include a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, a 2,3- difluorfenila, a 2,4-difluorfenila group, a 2,5-difluorfenila group, a 2,6-difluorfenila group, a 3,4-difluorfenila group, a 3,5-difluorfenila group, a 2,3,4 group, 5,6-pentafluorfenila, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2-bromophenyl group, a 3-bromophenyl group, a 4-bromophenyl group, a 2-iodophenyl group, a group 3-iodophenyl, a 4-iodophenyl group, a 2-trifluormethylphenyl group, a 3-trifluormethylphenyl group, a 4-tri-fluoromethylphenyl group, a 2-trifluormethoxyphenyl group, a 3-trifluoromethylphenyl group, a 4-trifluormethoxy group a 2-trifluormethylsulfa-nilphenyl group, a 3-trifluormethylsulfanylphenyl group, a 4-trifluormethylsulfanylphenyl group, a 4-methoxycarbonylphenyl group, a 4-nitrophenyl group, roup 4-cyanophenyl, a 4-methylaminophenyl group, a 4-di-methylaminophenyl group, a 4-methylsulfinylphenyl group, a 4-methylsulfo-nylphenyl group, a 4-acetylphenyl group and a 4-methoxycarbonylphenyl group.
[0029] The "heterocyclic group" in this invention represents a heterocyclic compound residue containing one or more nitrogen atoms, oxygen atoms or sulfur atoms, in addition to carbon atoms, as ring constituent atoms in the ring structure.
Examples of the "heterocyclic group" include 5-membered non-aromatic heterocyclic groups such as a pyrrolidine ring, a tetrahydrofuran ring and a tetrahydrothiophene ring, aromatic 5-membered heterocyclic groups such as a pyrrole ring, a pyrazole ring, an imine ring dazol, a furan ring, a thiophene ring, an oxazole ring and a ti-azole ring, 6-membered non-aromatic heterocyclic groups, such as a piperidine ring, a tetrahydropyran ring, a tetrahydrothiopyran ring, a piperazine ring morpholine group, and 6-membered aromatic heterocyclic groups such as a pyridine ring, a pyrimidine ring, a pyridazine ring and a pyrazine ring.
[0030] Furthermore, in that invention, the 5-membered heterocyclic group refers to a 5-membered non-aromatic heterocyclic group and a 5-membered aromatic heterocyclic group, and the 6-membered heterocyclic group refers to one 6-membered non-aromatic heterocyclic group and 6-membered aromatic heterocyclic group. Examples of the "5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the W group" in that invention include non-aromatic 5- or 6-membered heterocyclic groups, optionally with one or more atoms or groups selected from the W group, as a pyrrolidin-1-yl group, a 3,3,4,4-tetrafluorpirrolidin-1-yl group, a tetrahydrofuran-2-yl group, piperidyl groups, morpholyl groups and thiomorpholyl groups; and [0031] 5 or 6-membered aromatic heterocyclic groups optionally with one or more atoms or groups selected from the W group, such as a 2-pyrrolyl group, a 2-furyl group, a 3-furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1-pyrrolyl group, a 1-methyl-2-pyrrolyl group, a 2-methylsulfanyl-1-pyrrolyl group, a 2-methylsulfinyl-1-pyrrolyl group, a 2-methylsulfonyl- 1-pyrrolyl, a 2-methylamino-1-pyrrolyl group, a 2-dimethylamino-1-pyrrolyl group, a 5-bro-mo-2-furyl group, a 5-nitro-2-furyl group, a group 5-cyano-2-furyl, a 5-methoxy-2-furyl group, a 5-acetyl-2-furyl group, a 5-methoxy-carbonyl-2-furyl group, a 2-methyl-3-furyl group, a 2,5-dimethyl-3-furyl group, a 2,4-dimethyl-3-furyl group, a 5-methyl-2-thienyl group, a 3-methyl-2-thienyl group, a 1-methyl- 3-trifluormethyl-5-pyrazolyl, a 5-chloro-1,3-dimethyl-4-pyrazolyl group, a pyrazol-1-yl group, a 3-chloro-pyrazol-1-yl group, a 3-bromopyrazol- 1-yl, a 4-chloro group -pyrazol-1-yl, a 4-bromopyrazol-1-yl group, an imidazol-1-yl group, a 1,2,4-triazol-1-yl group, a 3-chloro-1,2,4 group -triazol-1-yl, a 1,2,3,4-tetrazol-1-yl group, a 1,2,3,5-tetrazol-1-yl group, a 2-thienyl group, a 3-thienyl group , a 3-trifluormethyl-1,2,4-triazol-1-yl group, a 4-trifluormethylpyrazol-1-yl group, a pyrazinyl group, a 4-pyrimidinyl group, a 5-pyrimidinyl group, a 2-pyridyl group , a 3-pyridyl group, a 4-pyridyl group, a 3-fluoro-2-pyridyl group, a 4-fluoro-2-pyridyl group, a 5-fluoro-2-pyridyl group, a 6-fluoro-2 group -pyridyl, a 2-pyrimidinyl group, a 3-chloro-5-trifluormethylpyridin-2-yl group, a 5-trifluormethylpyridin-2-yl group and a 5-trifluormethoxy pyridin-2-yl group. [0032] Examples of the "4, 5 or 6 membered heterocyclic group optionally with one or more atoms or groups selected from the group W" in that invention include 4, 5 or 6 membered non-aromatic heterocyclic groups, optionally with one or more atoms or groups selected from the W group, such as a tietan-3-yl group, a pyrrolidin-1-yl group, a 3,3,4,4-tetrafluorpirrolidin-1-yl group, a tetrahydrofuran-2-yl group, groups piperidyl, morpholyl groups and thio-morpholyl groups; and [0033] 5 or 6-membered aromatic heterocyclic groups optionally with one or more atoms or groups selected from the W group, such as a 2-pyrrolyl group, a 2-furyl group, a 3-furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1-pyrrolyl group, a 1-methyl-2-pyrrolyl group, a 2-methylsulfanyl-1-pyrrolyl group, a 2-methylsulfinyl-1-pyrrolyl group, a 2-methylsulfonyl- 1-pyrrolyl, a 2-methylamino-1-pyrrolyl group, a 2-dimethylamino-1-pyrrolyl group, a 5-bro-mo-2-furyl group, a 5-nitro-2-furyl group, a group 5-cyano-2-furyl, a 5-methoxy-2-furyl group, a 5-acetyl-2-furyl group, a 5-methoxy-carbonyl-2-furyl group, a 2-methyl-3-furyl group, a 2,5-dimethyl-3-furyl group, a 2,4-dimethyl-3-furyl group, a 5-methyl-2-thienyl group, a 3-methyl-2-thienyl group, a 1-methyl- 3-trifluormethyl-5-pyrazolyl, a 5-chloro-1,3-dimethyl-4-pyrazolyl group, a pyrazol-1-yl group, a 3-chloro-pyrazol-1-yl group, a 3-bromopyrazol- 1-yl, a 4-chlor group opirazol-1-yl, a 4-bromopyrazol-1-yl group, an imidazol-1-yl group, a 1,2,4-triazol-1-yl group, a 3-chloro-1,2,4- group triazol-1-yl, a 1,2,3,4-tetrazol-1-yl group, a 1,2,3,5-tetrazol-1-yl group, a 2-thienyl group, a 3-thienyl group, a 3-trifluormethyl-1,2,4-triazol-1-yl group, a 4-trifluormethylpyrazol-1-yl group, a pyrazinyl group, a 4-pyrimidinyl group, a 5-pyrimidinyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 3-fluoro-2-pyridyl group, a 4-fluoro-2-pyridyl group, a 5-fluoro-2-pyridyl group, a 6-fluoro-2- group pyridyl, a 2-pyri-midinyl group, a 3-chloro-5-trifluormethylpyridin-2-yl group, a 5-triflu-ormethylpyridin-2-yl group and a 5-trifluormethoxy pyridin-2-yl group.
[0034] Examples of "C1 to C6 alkoxy groups, optionally with one or more halogen atoms" in that invention include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2-tri-fluorethoxy group, a group propyloxy, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group and a hexyloxy group.
[0035] Examples of "C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms" in this invention include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl group, a hexylsulfanyl group, a trifluoromethylsulfanyl group, a 2,2,2-trifluorethylsulfanyl group and a pentafluorethylsulfanyl group.
[0036] Examples of the "C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms" in this invention include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, a hexylsulfinyl group , a trifluoromethylsulfinyl group, a 2,2,2-trifluorethylsulfinyl group and a pentafluorethylsulfinyl group.
[0037] Examples of the "C1 to C6 alkylsulfonyl groups optionally with one or more halogen atoms" in that invention include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a trifluoromethylsulfonyl group, a 2,2,2-trifluorethylsulfonyl group and a pentafluorethylsulfonyl group.
[0038] Examples of "C2 to C6 alkylcarbonyl groups optionally with one or more halogen atoms" in that invention include an acetyl group, a propionyl group, a butyryl group, a penta-noyl group, a hexanoyl group and a trifluoracetyl group.
[0039] Examples of the "C2 to C6 alkoxycarbonyl groups optionally with one or more halogen atoms" in that invention include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, a butyloxycarbonyl group, a pentyloxycarbonyl group, a tert-butyloxycarbonyl group and a 2,2,2-trifluorethyloxycarbonyl group.
Examples of "C1 to C6 alkylamino groups optionally with one or more halogen atoms" in that invention include a methylamino group, an ethylamino group, a 2,2,2-trifluorethylamino group, a propylamino group and an isopropylamino group.
[0041] Examples of the "C2 to C8 dialkylamino groups optionally with one or more halogen atoms" in that invention include a dimethylamino group, a diethylamino group, a bis (2,2,2-triflu-oroethyl) amino group and a dipropylamino group .
[0042] Examples of the "C2 to C6 alkenyloxy groups optionally with one or more halogen atoms" in that invention include a 2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2-bute-niloxy group, a group 3 -butenyloxy, a 2-pentenyloxy group, a 2-he-xenyloxy group, a 3,3-difluoralyloxy group and a 3,3-dichloroaloxy group.
[0043] Examples of the "C2 to C6 alkynyloxy groups optionally with one or more halogen atoms" in that invention include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 2-hexynyloxy group and a 4,4,4-trifluor-2-butynyloxy group.
Examples of "C1 to C6 alkylaminosulfonyl groups optionally with one or more halogen atoms" in that invention include a methylaminosulfonyl group, an ethylaminosulfonyl group, a 2,2,2-trifluorethylaminosulfonyl group, a propylaminosulfonyl group and an isopropylaminosulfonyl group .
[0045] Examples of "C2 to C8 dialkylaminosulfonyl groups optionally with one or more halogen atoms" in that invention include a dimethylaminosulfonyl group, a diethylaminosulfonyl group, a bis (2,2,2-trifluoroethyl) aminosulfonyl group and a dipropylami-oursulfonyl group .
Examples of the "C2 to C6 alkylcarbonylamino groups optionally having one or more halogen atoms" in that invention include an acetylamino group, a propionylamino group, a butyrylamino group, a pentanoylamino group, a hexanoylamino group and a trifluoracetylamino group.
[0047] Examples of "C2 to C6 alkoxycarbonyl groups optionally with one or more halogen atoms" in this invention include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, a butyloxycarbonyl group, a pentyloxycarbonyl group, a tert-butyloxycarbonyl group and a 2,2,2-trifluorethyloxycarbonyl group.
Examples of "C2 to C6 alkylaminocarbonyl groups optionally with one or more halogen atoms" in that invention include a methylaminocarbonyl group, an ethylaminocarbonyl group, a 2,2,2-trifluorethylaminocarbonyl group, a propylaminocarbonyl group and an isopropylaminocarbonyl group.
[0049] Examples of the "C3 to C10 dialkylaminocarbonyl groups optionally with one or more halogen atoms" in that invention include a dimethylaminocarbonyl group, a diethylaminocarbonyl group, a bis (2,2,2-trifluorethyl) aminocarbonyl group and a dipropylami-nocarbonyl group .
[0050] Specific examples of the compound in which "R3 and R4, together with the carbon atoms to which they are attached, form a benzene ring, optionally with one or more atoms or groups selected from the group W, a heterocyclic ring of 5 or 6 members, optionally with one or more atoms or groups selected from group W or a non-aromatic ring of 5, 6, 7 or 8 members optionally with one or more atoms or groups selected from group V ", include the following formulas (1K-1 ) to (1K-15): where W3, W13, W ° and W0 are the same or different, and each represents a hydrocarbon group C1 to C6 optionally with one or more halogen atoms, an alkoxy group C1 to C6 optionally with one or more halogen atoms, a C1 to C6 alkylsulfanyl group optionally with one or more halogen atoms, a C1 to C6 alkylsulfinyl group optionally with one or more halogen atoms, a C1 to C6 alkylsulfonyl group optionally with one or more halogen atoms, a group a alkylamino C1 to C6 optionally with one or more halogen atoms, a dialkylamino group C2 to C8 optionally with one or more halogen atoms, an alkylcarbonyl group C2 to C6 optionally with one or more halogen atoms, an alkoxycarbonyl group C2 to C6 optionally with one or more halogen atoms, a halogen atom, a cyano group, a nitro group or a hydrogen atom, W® represents a C1 to C6 alkyl group, optionally with one or more halogen atoms or an atom of hydrogen, and Va, Vb, Vc and Vd are the same or different, and each represents a C1 to C6 chain hydrocarbon group optionally with one or more halogen atoms, a C1 to C6 alkoxy group optionally with one or more halogen atoms , a C2 to C6 alkenyloxy group optionally with one or more halogen atoms, a C2 to C6 alkynyloxy group optionally with one or more halogen atoms, a halogen atom or a hydrogen atom.
[0051] Specific examples of groups G1 to G6 include groups (J1) to (J27) of the following formulas: where R10a represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from group Z, one alicyclic hydrocarbon group C3 to C9, optionally with one or more atoms or groups selected from group V, a 4, 5 or 6 membered heterocyclic group optionally with one or more atoms or groups selected from group W, CO2R8, C (O) R8 or C (O) NR8R9; and other symbols represent the same meaning, as in formula (1).
[0052] The N-oxide in this invention is a compound in which the nitrogen atom, constituting the ring in the heterocyclic group, is oxidized. Examples of the heterocyclic group that can form an N-oxide include a pyridine ring. In the compound of the present invention, the N-oxide includes the compounds represented by formulas (1N1) to (1N3) defined below.
[0053] Examples of the compound of the present invention include the following compounds.
In formula (1), compounds in which A1 is NR5;
In formula (1), compounds in which A1 is NR5 and R7 is a methyl group;
In formula (1), compounds in which A1 is a sulfur atom;
In formula (1), compounds in which A1 is an oxygen atom;
In formula (1), compounds in which A2 is a nitrogen atom;
In formula (1), compounds in which A2 is CR6;
In formula (1), compounds in which A2 is CH;
In formula (1), compounds in which A3 is a nitrogen atom;
In formula (1), compounds in which A3 is CR7;
In formula (1), compounds in which A3 is CH;
In formula (1), compounds where A1 is NR5, A2 is CR6 and A3 is a nitrogen atom;
In formula (1), compounds in which A1 is NR5, A2 is CR6 and A3 is CR7;
In formula (1), compounds where A1 is NR5, A2 is CH and A3 is a nitrogen atom;
In formula (1), compounds in which A1 is NR5, A2 is CH and A3 is CR7;
In formula (1), compounds in which A1 is NR5, A2 is CH and A3 is CH;
In formula (1), compounds in which A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is a nitrogen atom;
In formula (1), compounds in which A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is CR7;
In formula (1), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is a nitrogen atom;
In formula (1), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CR7;
In formula (1), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CH;
In formula (1), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is a nitrogen atom;
In formula (1), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is CR7;
In formula (1), compounds in which A1 is a sulfur atom, A2 is CH and A3 is a nitrogen atom;
In formula (1), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CR7;
In formula (1), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CH;
In formula (1), compounds in which A1 is an oxygen atom, A2 is CR6 and A3 is a nitrogen atom; 1 In formula (1), compounds in which A1 is an oxygen atom, A2 is CR6 and A3 is CR7;
In formula (1), compounds in which A1 is an oxygen atom, A2 is CH and A3 is a nitrogen atom;
In formula (1), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CR7;
In formula (1), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CH;
In formula (1), compounds in which R1 is a hydrocarbon group from the C1 to C6 chain optionally with one or more atoms or groups selected from the U group;
In formula (1), compounds in which R1 is an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V;
In formula (1), compounds in which R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups;
In formula (1), compounds in which R1 is a hydrocarbon group from the C1 to C6 chain optionally with one or more halogen atoms;
In formula (1), compounds in which R1 is a C1 to C6 alkyl group, optionally with one or more halogen atoms;
In formula (1), compounds in which R1 is a C3 to C6 cycloalkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and C1 to C6 alkyl groups, optionally with one or more halogen atoms;
In formula (1), compounds in which R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups, a C2 to C6 alkenyl group optionally with one or more halogen atoms, a C2 to C6 alkynyl group optionally with one or more halogen atoms or a C3 to C6 cycloalkyl group optionally with one or more atoms or groups selected from the group consisting of halogen atoms and C1 to C6 alkyl groups, optionally with one or more halogen atoms, In formula (1), compounds in which R1 is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a 2,2,2-trifluorethyl group, a cyclopropylmethyl group or a cyclopropyl group;
In formula (1), compounds in which R1 is a methyl group; In formula (1), compounds in which R1 is an ethyl group; In formula (1), compounds in which R1 is a propyl group; In formula (1), compounds in which R1 is a cyclopro-pilmethyl group;
In formula (1), compounds in which R1 is a cyclopropyl group;
In formula (1), compounds in which R2 is a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the U group;
In formula (1), compounds in which R2 is a phenyl group optionally having one or more atoms or groups selected from the group W;
In formula (1), compounds in which R2 is a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the group W, In formula (1), compounds in which R2 is OR8;
In formula (1), compounds in which R2 is S (O) mR8 or S (O) 2 NR8R9;
In formula (1), compounds in which R2 NR8R9, NR8CO2R9 or NR8C (O) R9;
In formula (1), compounds in which R2 is a CO2R8, C (O) R8 or C (O) NR8R9;
In formula (1), compounds in which R2 is a halogen atom;
In formula (1), compounds in which R2 is a halogen atom;
In formula (1), compounds in which R2 is a halogen atom or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the U group, or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different, and are a phenyl group optionally with one or more atoms or groups selected from the group W or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the group W, or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are OR8 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are S (O) mR8 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are SO2NR8R9 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are NR8R9 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are NR8CO2R9 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are NR8C (O) R9 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are CO2R8 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are C (O) R8 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are C (O) NR8R9 or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are a halogen atom or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different, and R3 and R4, together with the carbon atoms to which they are attached, form a benzene ring, optionally with one or more atoms or groups selected from the group W;
In formula (1), compounds in which R3 and R4 are the same or different, and form a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the group W;
In formula (1), compounds in which R3 and R4 are the same or different, and form a 5, 6, 7 or 8 membered non-aromatic ring optionally with one or more atoms or groups selected from group V;
In formula (1), compounds in which R3 and R4 are the same or different and are a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the group U, OR8, S (O) mR8, an atom of halogen or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different and are a C1 to C6 hydrocarbon group with one or more halogen atoms, OR8, where R8 represents a C1 to C6 hydrocarbon group with a or more halogen atoms, or S (O) mR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, a halogen atom or a hydrogen atom;
In formula (1), compounds in which R3 and R4 are the same or different, and are a C1 to C6 perfluoralkyl group with one or more halogen atoms, OR8, where R8 represents a C1 to C6 perfluoralkyl group, or S (O) mR8, where R8 represents a perfluoro-chyl group C1 to C6, a halogen atom or a hydrogen atom;
In formula (1), compounds in which R3 is a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the U group, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a phenyl group optionally having one or more atoms or groups selected from the group W, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the W group, and R4 is a hydrogen atom;
In formula (1), compounds where R3 is OR8, and R4 is a hydrogen atom;
In formula (1), compounds where R3 is S (O) mR8, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is SO2NR8R9, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is NR8R9, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is NR8CO2R9, and R4 is a hydrogen atom;
In formula (1), compounds where R3 is NR8C (O) R9, and R4 is a hydrogen atom;
In formula (1), compounds where R3 is CO2R8, and R4 is a hydrogen atom;
In formula (1), compounds where R3 is C (O) R8, and R4 is a hydrogen atom;
In formula (1), compounds where R3 is C (O) NR8R9, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a halogen atom, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a C1 to C6 hydrocarbon group optionally with one or more halogen atoms, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a hydrocarbon group of chains C1 to C6 with one or more halogen atoms, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a C1 to C6 alkyl group with one or more halogen atoms, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a perfluoroalkyl group C1 to C6, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is OR8, in which R8 represents a C1 to C6 hydrocarbon group with one or more halogen atoms, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is OR8, in which R8 represents a perfluoralkyl group C1 to C6, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is S (O) mR8, in which R8 represents a C1 to C6 perfluoralkyl group, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is OR8, in which R8 represents a perfluoralkyl group C1 to C6, and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a trifluoro-methyl group, a pentafluorethyl group, a heptafluorisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulphinyl group or a trifluoromethylsulfonyl group, and R4 is an hydrogen atom ;
In formula (1), compounds in which R3 is a trifluoromethyl group and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a pentafluethyl group and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a trifluoromethylsulfanyl group and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a trifluoromethylsulfinyl group and R4 is a hydrogen atom;
In formula (1), compounds in which R3 is a trifluoromethylsulfonyl group and R4 is a hydrogen atom;
In formula (1), compounds in which R5 is a C1 to C6 hydrocarbon group optionally with one or more atoms or groups selected from the group X, CO2R8, C (O) R8, an alicyclic hydrocarbon group C3 to C9 optionally with a or more atoms or groups selected from the group V, or a hydrogen atom;
In formula (1), compounds in which R5 is a hydrocarbon group of chain C1 to C6 optionally with one or more atoms or groups selected from the group X;
In formula (1), compounds in which R5 is CO2R8;
In formula (1), compounds in which R5 is C (O) R8;
In formula (1), compounds in which R5 is an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V;
In formula (1), compounds in which R5 is an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V;
In formula (1), compounds in which R5 is a hydrogen atom;
In formula (1), compounds in which R6 and R7 are the same or different and are a C1 to C6 chain hydrocarbon group optionally with one or more halogen atoms, or a hydrogen atom;
In formula (1), compounds in which R6 and R7 are the same or different and are a halogen atom or a hydrogen atom;
In formula (1), compounds in which R6 and R7 are the same or different and are OR8, S (O) mR8, NR8R9, a halogen atom or a hydrogen atom;
In formula (1), compounds in which R6 and R7 are a hydrogen atom;
In formula (1), compounds in which R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups, a C2 to C6 alkenyl group optionally with one or more halogen atoms, a C2 to C6 alkynyl group optionally with one or more halogen atoms or a C3 cycloalkyl group to C6 optionally with one or more atoms or groups selected from the group consisting of halogen atoms and alkyl groups C1 to C6, optionally with one or more halogen atoms, R2 is a halogen atom or a hydrogen atom, R3 and R4 are the same or different and are a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U, OR8, S (O) mR8, a halogen atom or a hydrogen atom, and R5 is a hydroc group chain carbon C1 to C6, optionally with one or more atoms or groups selected from the group X, CO2R8, C (O) R8, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, or a hydrogen atom;
In (1), compounds in which A1 is NR5, A2 is CR6, A3 is a nitrogen atom, R1 is a hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U and R2 is a hydrogen atom , G is group G1, group G2 or group G5, and Q is an oxygen atom, R10 is a hydrogen atom, R11 represents an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, OR25, where R25 represents a C1 to C6 chain hydrocarbon group with one or more atoms or groups selected from the Z group, NR30R31, where R30 and R31 are the same or different and optionally represent a C1 to C6 chain hydrocarbon group with one or more atoms or groups selected from the group Y, or C (O) R32, where R32 represents OR8, and R8 represents a hydrocarbon group from the C1 to C6 chain optionally with one or more atoms or groups selected from the Y group, R12 is a hydrogen atom, or SO2R33, where R33 represents a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from group Y, R13 is a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from group Y, R19 is a hydrogen atom , R20 is NR54R55, where R54 and R55 are the same or different, and are a C1 to C6 hydrocarbon group optionally with one or more atoms or groups selected from the Y group, R3 is a C1 to C6 hydrocarbon group optionally with one or more atoms or groups selected from the group U, R4 is a hydrogen atom, R5 is a hydrocarbon group from the C1 to C6 chain optionally with one or more atoms or groups selected from the X group, and R6 is a hydrogen atom;
In (1), compounds in which A1 is NR5, A2 is CR6, A3 is a nitrogen atom, R1 is a C1 to C6 alkyl group, optionally with one or more halogen atoms, R2 is a hydrogen atom; G is group G1, group G2 or group G5, and Q is an oxygen atom, R10 is a hydrogen atom, R11 are C3 to C9 cycloalkyl groups optionally with one or more halogen atoms, OR25, where R25 is a C1 to C6 alkyl group with a phenyl group optionally with one or more halogen atoms, NR30R31, where R30 and R31 are the same or different and represent a C1 to C6 alkyl group optionally with one or more halogen atoms, or C (O ) R32, where R32 represents OR8 and R8 represents a C1 to C6 alkyl group, optionally with one or more halogen atoms, R12 represents a hydrogen atom, or SO2R33, where R33 represents a C1 to C6 alkyl group, optionally with one or more halogen atoms, R13 is a C1 to C6 alkyl group, optionally with one or more halogen atoms, R19 is a hydrogen atom, R20 is NR54R55, where R54 and R55 are the same or different and represent an alkyl group C1 to C6 optionally with one or more atoms of halogen, R3 is a C1 to C6 alkyl group, optionally with one or more halogen atoms, R4 is a hydrogen atom, R5 is a C1 to C6 alkyl group, optionally with one or more halogen atoms, and R6 is an atom hydrogen;
In formula (1), compounds in which R1 is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a 2,2,2-trifluorethyl group, a cyclopropylmethyl group or a cyclopropyl group, R2 is a hydrogen atom; R3 and R4 are the same or different and are a C1 to C6 chain hydrocarbon group with one or more halogen atoms, OR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, or S (O) mR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, a halogen atom or a hydrogen atom, R5 is a C1 to C6 alkyl group, optionally with one or more halogen atoms or a hydrogen atom, and R6 and R7 are a hydrogen atom;
Compounds represented by formula (1 A), in which the symbols represent the same meaning as in formula (1);
In formula (1A), compounds where A1 is NR5, A2 is CR6 and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is NR5, A2 is CR6 and A3 is CR7;
In formula (1A), compounds in which A1 is NR5, A2 is CH and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is NR5, A2 is CH and A3 is CR7;
In formula (1A), compounds in which A1 is NR5, A2 is CH and A3 is CH;
In formula (1A), compounds where A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is CR7;
In formula (1A), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CR7;
In formula (1A), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CH;
In formula (1A), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is CR7;
In formula (1A), compounds in which A1 is a sulfur atom, A2 is CH and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CR7;
In formula (1A), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CH;
In formula (1A), compounds in which A1 is an oxygen atom, A2 is CR6 and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is an oxygen atom, A2 is CR6 and A3 is CR7;
In the formula (1A), compounds where A1 is an oxygen atom, A2 is CH and A3 is a nitrogen atom;
In formula (1A), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CR7;
In formula (1A), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CH;
Compounds represented by formula (1B), where the symbols represent the same meaning as in formula (1);
In formula (1B), compounds where A1 is NR5, A2 is CR6 and 3 A3 is a nitrogen atom;
In formula (1B), compounds where A1 is NR5, A2 is CR6 and A3 is CR7;
In formula (1B), compounds where A1 is NR5, A2 is CH and A3 is a nitrogen atom;
In formula (1B), compounds in which A1 is NR5, A2 is CH and A3 is CR7;
In formula (1B), compounds in which A1 is NR5, A2 is CH and A3 is CH;
In formula (1B), compounds where A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is a nitrogen atom;
In formula (1B), compounds in which A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is CR7;
In formula (1B), compounds where A1 is NR5, R5 is a methyl group, A2 is CH and A3 is a nitrogen atom;
In formula (1B), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CR7;
In formula (1B), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CH;
In formula (1B), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is a nitrogen atom;
In formula (1B), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is CR7;
In formula (1B), compounds in which A1 is a sulfur atom, A2 is CH and A3 is a nitrogen atom;
In formula (1B), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CR7;
In formula (1B), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CH;
In formula (1B), compounds in which A1 is an oxygen atom, A2 is CR6 and A3 is a nitrogen atom;
In formula (1B), compounds in which A1 is an oxygen atom, A2 is CR6 and A3 is CR7;
In formula (1B), compounds where A1 is an oxygen atom, A2 is CH and A3 is a nitrogen atom;
In formula (1B), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CR7;
In formula (1B), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CH;
In formula (1B), compounds where A1 is NR5 or an oxygen atom, A2 is CR6 and A3 is a CR7 or a nitrogen atom;
In formula (1B), compounds in which A1 is NR5 or an oxygen atom, A2 is CR6, A3 is CR7 or a nitrogen atom, R1 is a C1 to C6 hydrocarbon group optionally with one or more atoms or groups selected from the group U, R2 is a hydrogen atom; R3 is a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U, or S (O) mR8, and R4 is a hydrogen atom, In the formula (1B), compounds in which A1 is NR5 or an oxygen atom, R5 is a methyl group, A2 is CH, A3 is CH or a nitrogen atom, R1 is a C1 to C6 alkyl group, R2 is a hydrogen atom; R3 is a C1 to C6 alkyl group with one or more halogen atoms, a C1 to C6 alkylsulfanyl group with one or more halogen atoms, a C1 to C6 alkylsulfinyl group with one or more halogen atoms or a C1 to C6 alkylsulfonyl group with one or more halogen atoms, and R4 is a hydrogen atom, In the formula (1B), compounds in which A1 is NR5 or an oxygen atom, R5 is a methyl group, A2 is CH, A3 is CH or an atom nitrogen, R1 is an ethyl group, R2 is a hydrogen atom; R3 is a C1 to C3 perfluoralkyl group, a C1 to C3 perfluoralkylsulfanyl group, a C1 to C3 perfluoralkylsulfinyl group or a C1 to C3 perfluoralkylsulfonyl group, and R4 is a hydrogen atom, Compounds represented by the formula (1C), in which the symbols represent the same meaning as in formula (1);
In the formula (1C), compounds where A1 is NR5, A2 is CR6 and 3 A3 is a nitrogen atom;
In formula (1C), compounds in which A1 is NR5, A2 is CR6 and A3 is CR7;
In the formula (1C), compounds in which A1 is NR5, A2 is CH and A3 is a nitrogen atom;
In formula (1C), compounds in which A1 is NR5, A2 is CH and A3 is CR7;
In formula (1C), compounds in which A1 is NR5, A2 is CH and A3 is CH;
In the formula (1C), compounds where A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is a nitrogen atom;
In formula (1C), compounds in which A1 is NR5, R5 is a methyl group, A2 is CR6 and A3 is CR7;
In the formula (1C), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is a nitrogen atom;
In formula (1C), compounds where A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CR7;
In the formula (1C), compounds in which A1 is NR5, R5 is a methyl group, A2 is CH and A3 is CH;
In the formula (1C), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is a nitrogen atom;
In formula (1C), compounds in which A1 is a sulfur atom, A2 is CR6 and A3 is CR7;
In the formula (1C), compounds in which A1 is a sulfur atom, A2 is CH and A3 is a nitrogen atom;
In the formula (1C), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CR7;
In formula (1C), compounds in which A1 is a sulfur atom, A2 is CH and A3 is CH;
In formula (1C), compounds where A1 is an oxygen atom, A2 is CR6 and A3 is a nitrogen atom;
In the formula (1C), compounds in which A1 is an oxygen atom, A2 is CR6 and A3 is CR7;
In the formula (1C), compounds in which A1 is an oxygen atom, A2 is C and A3 is a nitrogen atom;
In the formula (1C), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CR7;
In the formula (1C), compounds in which A1 is an oxygen atom, A2 is CH and A3 is CH;
In formula (1), compounds where A1 is NR5 or an oxygen atom, A2 is CR6 and A3 is CR7 or a nitrogen atom;
In the formula (1C), compounds in which A1 is NR5 or an oxygen atom, A2 is CR6, A3 is CR7 or a nitrogen atom, R1 is a C1 to C6 hydrocarbon group optionally with one or more atoms or groups selected from the group U, R2 is a hydrogen atom; R3 is a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U, or S (O) mR8, and R4 is a hydrogen atom, In the formula (1C), compounds in which A1 is NR5 or an oxygen atom, R5 is a methyl group, A2 is CH, A3 is CH or a nitrogen atom, R1 is a C1 to C6 alkyl group, R2 is a hydrogen atom; R3 is a C1 to C6 alkyl group with one or more halogen atoms, a C1 to C6 alkylsulfanyl group with one or more halogen atoms, a C1 to C6 alkylsulfinyl group with one or more halogen atoms or a C1 to C6 alkylsulfonyl group with one or more halogen atoms, and R4 is a hydrogen atom, In the formula (1C), compounds in which A1 is NR5 or an oxygen atom, R5 is a methyl group, A2 is CH, A3 is CH or an atom nitrogen, R1 is an ethyl group, R2 is a hydrogen atom; R3 is a C1 to C3 perfluoralkyl group, a C1 to C3 perfluoralkylsulfanyl group, a C1 to C3 perfluoralkylsulfinyl group or a C1 to C3 perfluoralkylsulfonyl group, and R4 is a hydrogen atom, Compounds represented by the formula (1N1), in which the symbols represent the same meaning as in formula (1);
Compounds represented by the formula (1N2), in which the symbols represent the same meaning as in the formula (1);
Compounds represented by the formula (1N3), in which the symbols represent the same meaning as in the formula (1);
In formula (1), compounds where G is the G1 group;
In formula (1), compounds where G is the group G2;
In formula (1), compounds where G is the group G3;
In formula (1), compounds where G is the group G4;
In formula (1), compounds where G is the group G5;
In formula (1), compounds where G is the group G6;
In formula (1), compounds where G is the group G7;
In formula (1), compounds in which G is the group G2, group G3, group G4, group G5 or group G6;
In formula (1), compounds where G is the group G1 and R11 is R25, OR27, SR29, NR30R31 or C (O) R32;
In formula (1), compounds where G is the G1 group and R11 is R25 or OR27;
In formula (1), compounds where G is the group G1 and R11 is R26 or OR28;
In formula (1), compounds where G is the group G1 and R11 is R25, OR27, SR29, NR30R31 or C (O) R32;
In formula (1), compounds where G is the G1 group and R11 is SR29, NR30R31 or C (O) R32; and In formula (1A), compounds in which A1, A2, A3 and G are as in the combinations of [Table 1] to [Table 10] (mode 1 through mode 243).
[0054] Here, for example, modality 1 represents "in formula (1A), compounds in which A1 is NR5, A2 is CR6, A3 is CR7 and G is G1".
[Table 1] [Table 2] [Table 3] [Table 4] [Table 5] [Table 6] [Table 7] [Table 8] [Table 9] [Table 10] [0055] In the formula (1A), compounds where R5 is a methyl group, R6 and R7 are a hydrogen atom and A1, A2, A3 and G are as in the combinations in [Table 1] through [Table 10];
In formula (1A), compounds in which R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups, a C2 to C6 alkenyl group optionally with one or more halogen atoms, a C2 to C6 alkynyl group optionally with one or more halogen atoms or a C3 cycloalkyl group to C6 optionally with one or more atoms or groups selected from the group consisting of halogen atoms and alkyl groups C1 to C6, optionally with one or more halogen atoms, R2 is a halogen atom or a hydrogen atom, R3 and R4 are the same or different and are a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U, OR8, S (O) mR8, a halogen atom or a hydrogen atom, R5 is a hydrocarbon group chain carbide C1 to C6, optionally with one or more atoms or groups selected from group X, CO2R8, C (O) R8, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, or one hydrogen atom, and A1, A2, A3 and G are as in the combinations of [Table 1] to [Table 10];
In formula (1A), compounds in which R1 is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a 2,2,2-trifluorethyl group, a cyclopropylmethyl group or a cyclopropyl group, R2 is a hydrogen atom; R3 and R4 are the same or different and are a C1 to C6 hydrocarbon group with one or more halogen atoms, OR8, where R8 represents a C1 to C6 hydrocarbon group with one or more halogen atoms, or S ( O) mR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, a halogen atom or a hydrogen atom, R5 is a C1 to C6 alkyl group, optionally with one or more atoms halogen or a hydrogen atom, R6 and R7 are a hydrogen atom, and A1, A2, A3 and G are as in the combinations in [Table 1] to [Table 10];
In formula (1A), compounds in which R1 is an ethyl group, R2 is a hydrogen atom; R3 is a C1 to C3 perfluoralkyl group, a C1 to C3 perfluoralkylsulfanyl group, a C1 to C3 perfluoralkylsulfinyl group or a C1 to C3 perfluoralkylsulfonyl group, R4 is a hydrogen atom and A1, A2, A3 and G are as combinations from [Table 1] to [Table 10];
In formula (1B), compounds in which A1, A2, A3 and G are as in the combinations of [Table 1] to [Table 10] In formula (1B), compounds in which R5 is a methyl group, R6 and R7 are one hydrogen atom and A1, A2, A3 and G are as in the combinations from [Table 1] to [Table 10];
In formula (1B), compounds in which R5 is a methyl group, R6 and R7 are a hydrogen atom and A1, A2, A3 and G are as in the combinations in [Table 1] through [Table 10];
In formula (1B), compounds in which R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups, a C2 to C6 alkenyl group optionally with one or more halogen atoms, a C2 to C6 alkynyl group optionally with one or more halogen atoms or a C3 cycloalkyl group to C6 optionally with one or more atoms or groups selected from the group consisting of halogen atoms and alkyl groups C1 to C6, optionally with one or more halogen atoms, R2 is a halogen atom or a hydrogen atom, R3 and R4 are the same or different and are a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U, OR8, S (O) mR8, a halogen atom or a hydrogen atom, R5 is a hydrocarbon group chain carbide C1 to C6, optionally with one or more atoms or groups selected from group X, CO2R8, C (O) R8, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, or one hydrogen atom, and A1, A2, A3 and G are as in the combinations of [Table 1] to [Table 10];
In formula (1B), compounds in which R1 is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a 2,2,2-trifluorethyl group, a cyclopropylmethyl group or a cyclopropyl group, R2 is a hydrogen atom; R3 and R4 are the same or different and are a C1 to C6 chain hydrocarbon group with one or more halogen atoms, OR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, or S (O) mR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, a halogen atom or a hydrogen atom, R5 is a C1 to C6 alkyl group, optionally with one or more halogen atoms or a hydrogen atom, R6 and R7 are a hydrogen atom, and A1, A2, A3 and G are as in the combinations in [Table 1] to [Table 10];
In formula (1B), compounds in which R1 is an ethyl group, R2 is a hydrogen atom; R3 is a C1 to C3 perfluoralkyl group, a C1 to C3 perfluoralkylsulfanyl group, a C1 to C3 perfluoralkylsulfinyl group or a C1 to C3 perfluoralkylsulfonyl group, R4 is a hydrogen atom and A1, A2, A3 and G are as combinations from [Table 1] to [Table 10];
In formula (1C), compounds where A1, A2, A3 and G are as in the combinations of [Table 1] through [Table 10];
In the formula (1C), compounds in which R5 is a methyl group, R6 and R7 are a hydrogen atom and A1, A2, A3 and G are as in the combinations in [Table 1] through [Table 10];
In formula (1C), compounds in which R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups, a C2 to C6 alkenyl group optionally with one or more halogen atoms, a C2 to C6 alkynyl group optionally with one or more halogen atoms or a C3 cycloalkyl group to C6 optionally with one or more atoms or groups if selected from the group consisting of halogen atoms and C1 to C6 alkyl groups, optionally with one or more halogen atoms, R2 is a halogen atom or a hydrogen atom, R3 and R4 are the same or different and are a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the group U, OR8, S (O) mR8, a halogen atom or a hydrogen atom, R5 is a group hydrocar chain bonnet C1 to C6, optionally with one or more atoms or groups selected from the group X, -CO2R8, -C (O) R8, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from the group V, or a hydrogen atom, and A1, A2, A3 and G are as in the combinations in [Table 1] to [Table 10];
In formula (1C), compounds in which R1 is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a 2,2,2-trifluorethyl group, a cyclopropylmethyl group or a cyclopropyl group, R2 is a hydrogen atom; R3 and R4 are the same or different and are a C1 to C6 chain hydrocarbon group with one or more halogen atoms, OR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, or S (O) mR8, where R8 represents a C1 to C6 chain hydrocarbon group with one or more halogen atoms, a halogen atom or a hydrogen atom, R5 is a C1 to C6 alkyl group, optionally with one or more halogen atoms or a hydrogen atom, R6 and R7 are a hydrogen atom, and A1, A2, A3 and G are as in the combinations in [Table 1] to [Table 10];
In formula (1C), compounds in which R1 is an ethyl group, R2 is a hydrogen atom; R3 is a C1 to C3 perfluoralkyl group, a C1 to C3 perfluoralkylsulfanyl group, a C1 to C3 perfluoralkylsulfinyl group or a C1 to C3 perfluoralkylsulfonyl group, R4 is a hydrogen atom and A1, A2, A3 and G are as combinations from [Table 1] to [Table 10].
[0056] In the following, the method for producing the compound of the present invention will be described.
[0057] The compound of the present invention and the intermediate compound can be produced, for example, according to (Production Method 1) to (Production Method 7) below. (Production Method 1) [0058] The compound of the present invention (1-G1) where G is G1 in the formula (1) can be produced by reacting the intermediate compound (M1) with the compound (M2), the compound ( M3) or the compound (M4).
[0059] In the formula, the symbols represent the same meaning as in formula (1).
[0060] The compound of the present invention (1-G1) can be produced by reacting the intermediate compound (M1) with the compound (M2).
[0061] The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers, such as 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as THF) and tert-butylmethyl ether, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2 -dichloroethane and chlorobenzene, aromatic hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as N, N-dimethylforamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), 1,3-dimethyl-2-imidazolidinone and dimethylsulfoxide (hereinafter referred to as DMSO), aromatic compounds containing nitrogen, such as pyridine and quinolone, and mixtures thereof.
[0062] Examples of the condensing agent used in the reaction include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) hydrochloride (hereinafter referred to as EDCI hydrochloride) and 1,3-dici-clohexylcarbodi -imide.
[0063] The reaction can also be carried out by adding a catalyst as needed.
[0064] Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole (hereinafter referred to as HOBt).
[0065] In the reaction, the compound (M2) is normally used in a 1 to 2 mol ratio, the condensing agent is generally used in a 1 to 5 mol ratio and the catalyst is generally used in a 0.01 ratio to 1 mol, based on 1 mol of the intermediate compound (M1).
[0066] The reaction temperature in the reaction is generally in the range of 0 to 120 ° C. The reaction time in the reaction is usually within the range of 0.1 to 24 hours.
[0067] After the completion of the reaction, the compound of the present invention (1-G1) can be isolated by adding the reaction mixture to the water, then extracting the mixture with an organic solvent and concentrating the organic layer; collecting by filtration a solid generated by adding the reaction mixture to the water; or collecting by filtration a solid generated in the reaction mixture. The isolated compound of the present invention (1-G1) can also be further purified by recrystallization, chromatography or the like.
[0068] The compound of the present invention (1-G1) can be produced by reacting the intermediate compound (M1) with the compound (M3) or the compound (M4).
[0069] The reaction is usually carried out in the presence of a solvent.
[0070] Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane and octane, aromatic hydrocarbons, such as toluene and xylene, hydrocarbons halogenated compounds such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
[0071] The reaction can also be carried out by adding a base as needed.
[0072] The base used in the reaction includes alkali metal carbonates, such as sodium carbonate and potassium carbonate, tertiary amines, such as triethylamine and N, N-diisopropylethylamine, nitrogen-containing aromatics, such as pyridine, 4-dimethylaminopyridine and the like .
[0073] In the reaction, the compound (M3) or the compound (M4) is normally used in the ratio of 1 to 2 mol, and the base is generally used in the ratio of 1 to 5 mol, based on 1 mol of the intermediate compound (M1).
[0074] The reaction temperature in the reaction is generally in the range of -20 to 100 ° C. The reaction time in the reaction is normally in the range of 0.1 to 24 hours.
[0075] After the end of the reaction, the reaction mixture is subjected to post-treatment operations, such as adding water to the reaction mixture, extracting the reaction mixture with an organic solvent and drying and concentrating the organic layer, whereby the compound of the present invention (1-G1) can be isolated. The isolated compound of the present invention (1-G1) can also be further purified by chromatography, recrystallization or the like. (Production Method 2) [0076] The compound of the present invention (1-G2), where G is G2 in the formula (1), can be produced by the reaction of the internal compound (M5) with the compound (M6) or the compound (M7).
[0077] In the formula, the symbols represent the same meaning as in formula (1).
[0078] The reaction is usually carried out in the presence of a solvent.
[0079] Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane and octane, aromatic hydrocarbons, such as toluene and xylene, hydrocarbons halogenated compounds such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
[0080] The reaction can also be carried out by adding a base as needed.
[0081] The base used in the reaction includes alkali metal carbonates, such as sodium carbonate and potassium carbonate, tertiary amines, Ltendo nitrogen, such as pyridine, 4-dimethylaminopyridine and the like.
[0082] In the reaction, the compound (M6) or the compound (M7) is normally used in the ratio of 1 to 2 mol, and the base is generally used in the ratio of 1 to 5 mol, based on 1 mol of the intermediate compound (M5).
[0083] The reaction temperature in the reaction is generally in the range of -20 to 100 ° C. The reaction time in the reaction is normally in the range of 0.1 to 24 hours.
[0084] After the end of the reaction, the reaction mixture is subjected to post-treatment operations, such as adding water to the reaction mixture, extracting the reaction mixture with an organic solvent and drying and concentrating the organic layer, whereby the compound of the present invention (1-G2) can be isolated. The isolated compound of the present invention (1-G2) can also be further purified by chromatography, recrystallization or the like. (Production Method 3) [0085] The compound of the present invention (1-G3), where G is G3 in the formula (1), can be produced by reacting the intermediate compound (M8) with the compound (M9).
[0086] In the formula, X represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and other symbols represent the same meaning as in formula (1).
[0087] The reaction is usually carried out in the presence of a solvent.
[0088] Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane and octane, aromatic hydrocarbons, such as toluene and xylene, hydrocarbons halogenated compounds such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
[0089] The reaction can also be carried out by adding a base as needed.
[0090] The base used in the reaction includes inorganic bases, such as tripotassium phosphate, potassium carbonate and sodium hydride, tertiary amines such as triethylamine and N, N-diisopropylethylamine, aromatic compounds containing nitrogen, such as pyridine, 4-dimethylaminopyridine and the like .
[0091] In the reaction, the compound (M9) is normally used in a 1 to 5 mole ratio, and the base is generally used in a 1 to 5 mole ratio, based on 1 mole of the intermediate compound (M8). [0092] The reaction temperature in the reaction is generally in the range of 0 to 150 ° C. The reaction time in the reaction is normally in the range of 0.1 to 24 hours.
[0093] After the completion of the reaction, the reaction mixture is subjected to post-treatment operations, such as adding water to the reaction mixture, extracting the reaction mixture with an organic solvent and drying and concentrating the organic layer, whereby the compound of the present invention (1-G3) can be isolated. The isolated compound of the present invention (1-G3) can also be further purified by chromatography, recrystallization or the like. (Production Method 4) [0094] The compound of the present invention (1-G4), where G is G4 in formula (1), can be produced by reacting the intermediate compound (M8) with the compound (M10).
[0095] In the formula, the symbols represent the same meaning as described above.
[0096] The compound of the present invention (1-G4) can be produced using the compound (M10) in place of the compound (M9), according to the method described in Production Method 3. (Production Method 5) [ 0097] The compound of the present invention (1-G5), where G is G5 in formula (1), can be produced by reacting the intermediate compound (M11) with the compound (M12).
[0098] In the formula, the symbols represent the same meaning as in formula (1).
[0099] The reaction is carried out in the presence of a solvent, or the compound (M12) is used as a solvent.
[00100] Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1,4-dioxane, aliphatic hydrocarbons, such as hexane, heptane and octane, aromatic hydrocarbons, such as toluene and xylene, hydrocarbons halogenated, such as chlorobenzene, esters, such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents, such as DMF, NMP and DMSO, and mixtures thereof.
[00101] The reaction can also be carried out by adding a dehydrating agent as needed.
[00102] The dehydrating agent used in the reaction includes mineral acids, such as hydrochloric acid, and sulfonic acids, such as p-toluenesulfonic acid.
[00103] In the reaction, the compound (M12) is normally used in a ratio of 1 to 5 moles, and the dehydrating agent is normally used in a ratio of 0.1 to 2 moles, based on 1 mole of the intermediate compound (M11).
[00104] The reaction temperature in the reaction is generally in the range of 0 to 150 ° C. The reaction time in the reaction is normally in the range of 0.1 to 24 hours.
[00105] After completion of the reaction, the reaction mixture is subjected to post-treatment operations, such as adding water to the reaction mixture, extracting the reaction mixture with an organic solvent and drying and concentrating the organic layer, whereby the compound of the present invention (1-G5) can be isolated. The isolated compound of the present invention (1-G5) can also be further purified by chromatography, recrystallization or the like. (Production Method 6) [00106] The compound of the present invention (1-J26), where G is G6 and p is 0 in formula (1), can be produced by reacting the intermediate compound (M11) with the compound (M13 ), in the presence of an oxidizing agent. The compound of the present invention (1-J27), where G is G6 and p is 1 in formula (1), can be produced by oxidizing the compound of the present invention (1-J26).
[00107] In the formula, the symbols represent the same meaning as in formula (1).
[00108] The compound of the present invention (1-J26) can be produced by the reaction of the intermediate compound (M11) with the compound (M13), in the presence of an oxidizing agent.
[00109] The reaction is usually carried out in the presence of a solvent. [00110] Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1,4-dioxane, aliphatic hydrocarbons, such as hexane, heptane and octa-no, aromatic hydrocarbons, such as toluene and xylene, hydrocarbons halogenated compounds such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, polar aprotic solvents such as DMF, NMP and DMSO, alcohols such as methanol and ethanol, water and mixtures thereof.
[00111] Examples of the oxidizing agent used in the reaction include halogenating agents, such as N-chlorosuccinimide and hypervalent iodine compounds, such as iodobenzene diacetate.
[00112] In the reaction, the compound (M13) is normally used in a 1 to 5 mole ratio, and the oxidizing agent is normally used in a 1 to 5 mole ratio, based on 1 mole of the intermediate compound (M11) .
[00113] The reaction temperature in the reaction is generally in the range of 0 to 150 ° C. The reaction time in the reaction is normally in the range of 0.1 to 24 hours.
[00114] After the end of the reaction, the reaction mixture is subjected to post-treatment operations, such as adding water to the reaction mixture, extracting the reaction mixture with an organic solvent and drying and concentrating the organic layer, whereby the compound of the present invention (1-J26) can be isolated. The isolated compound of the present invention (1-J26) can also be further purified by chromatography, recrystallization or the like.
[00115] The compound of the present invention (1-J27), where G is G6 and p is 1 in formula (1), can be produced by oxidizing the compound of the present invention (1-J26).
[00116] The reaction is usually carried out in the presence of a solvent. [00117] Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons, such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water and mixtures thereof.
[00118] Examples of the oxidizing agent used in the reaction include sodium pyriodate and m-chloroperbenzoic acid.
[00119] In the reaction, the oxidizing agent is generally used in the ratio of 1 to 3 moles, based on 1 mol of the compound of the present invention (1-J26).
[00120] The reaction temperature in the reaction is generally in the range of -50 to 50 ° C. The reaction time in the reaction is normally in the range of 0.1 to 12 hours.
[00121] After the completion of the reaction, the reaction mixture is subjected to post-treatment operations, such as extracting the reaction mixture with an organic solvent, washing the organic layer with an aqueous solution of a reducing agent (for example, sulfite sodium, sodium thiosulfate) and an aqueous solution of a base (eg sodium bicarbonate), as needed, and drying and concentration of the organic layer, whereby the compound of the present invention (1-J27) can be isolated. The isolated compound of the present invention (1-J27) can also be further purified by chromatography, recrystallization or the like. (Production Method 7) [00122] The compound of the present invention (1-G7), where G is G7 in formula (1), can be produced by reacting the intermediate compound (M8) with the compound (M14).
[00123] In the formula, the symbols represent the same meaning as described above.
[00124] The compound of the present invention (1-G7) can be produced, using the compound (M14), in place of the compound (M9), according to the method described in Production Method 3. (Production Method 8) [00125] The intermediate compound (M8) can be synthesized, for example, by the method described in Patent Document 1 (WO2013 / 018928).
[00126] The intermediate compound (M1) can be produced by reacting the intermediate compound (M8) with the compound (M15).
[00127] The intermediate compound (M5) can be produced by reacting the intermediate compound (M8) with the compound (M16).
[00128] The intermediate compound (M11) can be produced by reacting the intermediate compound (M8) with sodium azide to produce the intermediate compound (M17) and then reducing the intermediate compound (M17).
[00129] In the formula, the symbols represent the same meaning as in formula (1).
[00130] The intermediate compound (M1) can be produced, using the compound (M15), in place of the compound (M9), according to the method of Production Method 3.
[00131] The intermediate compound (M5) can be produced, using the compound (M16), in place of the compound (M9), according to the Method of Production Method 3.
[00132] The intermediate compound (M17) can be produced by reacting the intermediate compound (M8) with sodium azide.
[00133] The reaction is usually carried out in the presence of a solvent.
[00134] Examples of the solvent used in the reaction include ethers, such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether and 1,4-dioxane, polar aprotic solvents such as DMF, NMP and DMSO, alcohols such as methanol and ethanol, water and mixtures thereof .
[00135] In the reaction, sodium azide is generally used in the ratio of 1 to 5 moles, based on 1 mol of the intermediate compound (M8). [00136] The reaction temperature in the reaction is generally in the range of 0 to 150 ° C. The reaction time in the reaction is normally in the range of 0.1 to 24 hours.
[00137] After the end of the reaction, the reaction mixture is subjected to post-treatment operations, such as adding water to the reaction mixture, extracting the mixture with an organic solvent and drying and concentrating the organic layer, whereby the intermediate compound (M17) can be isolated. The intermediate compound (M11) can be produced by reducing the intermediate compound (M17).
[00138] The reaction is usually carried out in the presence of a solvent.
[00139] Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane and octane, aromatic hydrocarbons, such as toluene and xylene, hydrocarbons halogenated compounds such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, polar aprotic solvents such as DMF, NMP and DMSO, alcohols such as methanol and ethanol, water and mixtures thereof.
[00140] Examples of the reducing agent used in the reaction include phosphine compounds such as triphenylphosphine and tributylphosphine, tin (II) chloride, zinc and the like.
[00141] The reaction can also be carried out by adding an acid as needed.
[00142] Examples of the acid used in the reaction include mineral acids, such as hydrochloric acid, and carboxylic acids, such as acetic acid.
[00143] In the reaction, the reducing agent is generally used in the ratio of 1 to 5 moles, and the acid is generally used in a ratio of 0.01 to 1 mol, based on 1 mol of the intermediate compound (M17).
[00144] The reaction temperature in the reaction is generally in the range of 0 to 150 ° C. The reaction time in the reaction is normally in the range of 0.1 to 24 hours.
[00145] After completion of the reaction, the reaction mixture is subjected to post-treatment operations, such as adding water to the reaction mixture, extracting the mixture with an organic solvent and drying and concentrating the organic layer, whereby the intermediate compound (M11) can be isolated. The isolated intermediate compound (M11) can also be further purified by chromatography, recrystallization or the like.
[00146] In the following, specific examples of the compound of the present invention are shown below.
[00147] Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] through [Table 21];
[Table 11] [Table 12] [Table 13] [Table 14] [Table 15] [Table 16] [Table 17] [Table 18] [Table 19] [Table 20] [Table 21] [00148] (Na [ Table 11] to [Table 21] above, CycPr represents a cyclopropyl group, pH represents a phenyl group, 2-furyl represents a furyl-2-yl group and Bn represents a benzyl group.) Compounds of the present invention, in the formula ( 1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] through [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1A), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfonyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfonyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfonyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1B), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfonyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a pentafluorethyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfanyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfinyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfonyl group, n is 0 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfonyl group, n is 1 and A1, A2, A3 and G are the combinations shown in [Table 11] to [Table 21];
[00149] Compounds of the present invention, in formula (1C), where R1 is an ethyl group, R2 and R4 are a hydrogen atom, R3 is a trifluoromethylsulfonyl group, n is 2 and A1, A2, A3 and G are the combinations shown in [Table 11] through [Table 21].
[00150] Examples of the pest on which the compound of the present invention has an effect include arthropod pests such as Insecta, Arachnida, Chilopoda, Diplopoda, Isopoda and Gastropoda, and Nematode pests such as Nematoda. Examples of insects that are pests include Hemiptera, Lepidoptera, Thysanoptera, Diptera, Coleoptera, Orthoptera, Siphonaptera, Anoplura, Mallophaga, Hymenoptera, Blat-todea, Isoptera and the like. Examples of Arachnida include the pests Araneae, Acarina and the like. Specifically, examples of the pests include those shown below.
[00151] Hemiptera: Delphacidae such as Laodelphax striatellus, Nila-parvata lugens, and Sogatella furcifera, Deltocephalidae as Nephotet-tix cincticeps, Nephotettix virescens and Empoasca onukii, Aphididae as Aphis gossype, Aysidea, Mycusic, Persian, Myzus solani, Rhopalo-siphum padi, Toxoptera citricidus and Hyalopterus pruni, Pentatomidae as Nezara antennata, Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus and Mixed halyomorpha, Aleyrodidae as Trialeuro-des vaporariuridocidaeurididaeuridae, tabia , Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi, Planococcus kraunhiae, Pseudococcus longispinis and Pseudaulacaspis pentagona, Tingidae, Cimicoidea such as Cimex lectularius and Psyliidae.
[00152] Lepidoptera: Pyralidae, such as Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia inter-punctella, Ostrinia furnacalis, Hellula undalis and Pediasia teterrellus, Noctuidae, as Spodoptera Agritica, spodoptera litura, ipsilon, Plusia nigrisigna, Thoriccoplusia spp., Heliothis spp. and Helicoverpa spp., Pieridae as Pieris rapae, Adoxophyes spp., Tortricidae as Grapholita molesta, Legu-minivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai., Homona magnanima, Archips fuscocia-pomean and Grynae theivora and Phyllonorycter ringoneella, Carposinidae as Carposina niponensis, Lyonetiidae as Lyonetia spp. and Lymantriidae as Lymantria spp. and Euproctis spp., Yponomeutidae as Plutella xylostella, Gelechiidae as Pectinophora gossypiella and Phthorimaea operculella, Arctiidae as Hyphantria cunea and Tineidae, as Tinea translucens and Tineola bisselliella.
[00153] Thysanoptera: Thripidae, such as Frankliniella occidentalis, Thrips parmi, Scirtothrips dorsalis, Thrips tabaci, and Frankliniella intonsa. [00154] Diptera: Culex as Culex pipiens pallens, Culex tritaeni-orhynchus, and Culex quinquefasciatus, Aedes spp. such as Aedes aegypti and Aedes albopictus, Anopheles spp. such as Anopheles sinensis, Chiro-nomidae, Muscidae as Musca domestica and Muscina stabulans, Cal-liphoridae, Sarcophagidae, Fanniidae, Anthomyiidae as Delia platu-ra and Delia antiqua, Agromyzidae as Agromyza oryzae, Hydrellia grie, liri e Chromatomyia horticola, Chloropidae as Chlorops oryzae, Tephritidae as Dacus cucurbi-tae and Ceratitis capitata, Drosophilidae, Phoridae as Megaselia spi-racularis, Psychodidae as Clogmia albipunctata, Sciaridae, Simuli-dae, Tabulidae and Tabulidae.
[00155] Coleoptera: Diabrotica as Diabrotica virgifera virgifera and Diabrotica undecimpunctata howardi, Scarabaeidae as Anomala cuprea Anomala rufocuprea and Popillia japonica, Curculionidae as Sitophilus zeamais, Lissorhoptrus oryzophisis and ryosemisis and rysobrown and such as Tenebrio molitor and Tribolium casta-neum, [00156] Chrysomelidae, such as Oulema oryzae, Aulacophora femora-lis, Phyllotreta striolata and Leptinotarsa decemlineata, Dermestidae as Anthrenus verbasci and Dermestes maculates, Anobiidaee as La-siodic, as an eiodic, brunneus, Scolytidae as Tomicus piniperda, Bostrychidae, Ptinidae, Cerambycidae as Anoplophora malasiaca, Elateridae as Agriotes spp. and Limonius spp., and Paederus fuscipes.
[00157] Orthoptera: Locusta migratoria, Gryllotalpa africana, Oxya yezoensis, Oxya japonica, and Grylloidea.
[00158] Aphaniptera: Ctenocephalides felis, Ctenocephalides canis, Pulex irritans, Xenopsylla cheopis, and the like.
[00159] Anoplura: Pediculus humanus corporis, Pediculus humanus humanus, Phthirus pubis, Haematopinus eurysternus, Dalmalinia ovis, Haematopinus suis, Linognathus setosus and the like.
[00160] Mallophaga: Dalmalinia ovis, Dalmalinia bovis, Menopon gallinae, Trichodectes canis, Felicola subrostrata and the like.
[00161] Hymenoptera: Formicidae such as Monomorium pharaosis, Formica fusca japonica, Ochetellus glaber, Pristomyrmex pungens, Pheidole noda, Acromyrmex spp., Solenopsis spp., And Linepithema hu-mile, Vespidae, Bethylidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee and Atenthinidaee.
[00162] Nematoda: Aphelenchoides besseyi, Nothotylenchus acris, Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Heterodera glycines, Globodera rostochiensis, Pratylenchus coffeae and Pratylenchus neglectus.
[00163] Blattodea: Blattella germanica, Periplaneta fuliginosa, American Peri-planet, Periplaneta brunnea and Blatta orientalis.
[00164] Isoptera: Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formo- sanus, Neotermes koshunensis, Glyptotermes satsumensis, Glypto-termes nakajimai, Glyptotermes fuscus, Glyptismes, glyptismes, glyptismes, Reticulitermes miyatakei, Reticulitermes flaviceps amami-anus, Reticulitermes sp., Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and the like.
[00165] Acarina: Tetranychidae, like Tetranychus urticae, Te-tranychus kanzawai, Panonychus citri, Panonychus ulmi, and Oli-gonychus spp., Eriophyidae like Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersis, Acacopsycysisis, Calacarus, Aculus schlechtendali, Tarsonemidae as Polyphagotarsonemus latus, Tenuipalpidae as Brevipalpus phoeni-cis, Tuckerellidae, Metastigmata such as Haemaphysalis longicornis, Ha-emaphysalis flava, Dermacentor taiwanicus, Dermacentorhysma, Oxidis, persma , Acari-dae as Tyrophagus putrescentiae and Tyrophagus similis, Pyroglyphi-dae as Dermatophagoides farinae and Dermatophagoides ptrenyss-nus, Cheyletidae as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus sciisie and Cheyleti moorei and Cheyletus moorei and Cheyleti moorei Lis-trophoridae, Cr yptostigmata, Dermanyssidae as Ornithonyssus ba-coti, Ornithonyssus sylvairum and Dermanyssus gallinae, Trombiculidae as Leptotrombidium akamushi and the like.
[00166] Acarina pests: Chiracanthium japonicum, Latrodectus has-seltii and the like.
[00167] Chilopoda, Scutigeromorpha pests: Thereuonema hilgen-dorfi, Scolopendra subspinipes, and the like.
[00168] Diplopoda, Polydesmoidea pests: Oxidus gracilis, Nedyo-pus tambanus and the like.
[00169] Malacostraca, Isopoda: Armadillidium vulgare and the like. [00170] Gastropoda, Stylommatophora pests: Limax marginatus, Limax flavus and the like.
[00171] The pest control agent of the present invention contains the compound of the present invention and an inert vehicle. The pest control agent of the present invention is usually obtained by mixing the compound of the present invention and an inert vehicle, such as a solid vehicle, a liquid vehicle or a gaseous vehicle, and adding a surfactant to other adjuvants for the formulation, if necessary , to be formulated in emulsifiable concentrates, in oily formulations, powder formulations, granules, wettable, dryable powders, in microcapsule formulations, aerosols, de-smoking agents, poisonous bait formulations, resin formulations, shampoo agents , paste formulations, foaming agents, carbon dioxide preparations, tablets and the like. These formulations can be transformed into mosquito repellent spirals, electric mosquito repellent mats, into a liquid mosquito repellent formulation, into a smoking agent, a fumigant, a leaf formulation, a locally applied agent, a oral treatment and used.
[00172] The pest control agent of the present invention generally contains the compound of the present invention in an amount of 0.01 to 95% by weight.
[00173] Examples of the solid carrier that is used in the formulation include fine powder and clay granules (kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay, etc.), synthetic hydrated silicon oxide, talc, ceramics , other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), fine powder and granulated chemical fertilizer substances (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, chloride ammonium, etc.) and the like, synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethylmethacrylate and polyethylene terephthalate, nylon resins such as nylon-6, nylon-11 and nylon-66, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer and the like).
[00174] Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylethylene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate , isopropyl myristate, ethyl oleate, de-isopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, 1,4- dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycolmohomethyl ether, propylene glycol monomethyl ether, dipropylene glycolmohomethyl ether, 3-methoxy-3-methyl-1-butanol, etc.), N-dimethyl amide, N, N , N-dimet ilacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), and propylene carbonate and vegetable oils (soybean oil, sunflower oil, etc.) .
[00175] Examples of the gaseous vehicle include fluorocarbon, bu-tane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.
[00176] Examples of the surfactant include non-ionic surfactants, such as polyoxyethylenealkyl ether, polyoxyethylenealkyl ether and polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates and alkyl sulfates.
[00177] The other adjuvants for the formulation include fixing, dispersing, coloring and stabilizing agents, specifically, for example, casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, ben-tonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl-pyrrolidone, polyacrylic acid, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (mixtures 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
[00178] Examples of a base material of the resin formulation include vinyl chloride polymer, polyurethane and the like, and a plasticizer such as phthalate esters (dimethyl phthalate, dioctyl phthalate, etc.), adipate esters or stearic acid can be added to these base materials, as needed. The resin formulation is obtained by kneading a compound into the base material using a common kneading device, and then molding it by injection molding, extrusion molding, pressing molding or the like, and the formulation obtained resin can be additionally subjected to a molding or cutting step, as needed, to be processed into a resin formulation in plate, film, tape, reticular or fiber. These resin formulations are processed, for example, in an animal collar, an ear tag for the animal, a leaf formulation, an induction cable and a gardening pole.
[00179] Examples of a poisonous bait base material include powdered grains, vegetable oil, sugar, crystalline cellulose and the like, and, in addition, an antioxidant such as dibutylhydroxytoluene and nordihydroguaiaretic acid, a preservative such as dehydroacetic acid , a substance to prevent accidental ingestion by children and pets, such as red pepper powder, an attractive pest flavor, such as a cheese flavor, onion flavor and peanut oil, or the like, are added as needed.
[00180] The method for controlling the pests of the present invention is carried out by applying an effective amount of the compound of the present invention in a pest directly and / or in an area infested by pests (plants, soil, interior of houses, body of the animal, etc.). In the pest control method of the present invention, the compound is generally used in the form of the pest control agent of the present invention.
[00181] When the pest control agent of the present invention is used in pest control in the agricultural domain, the amount of application is generally 1 to 10,000 g in the amount of the compound of the present invention per 10,000 m2. When the pest control agent of the present invention is formulated in an emulsifiable concentrate, a wettable powder, a flowable or similar, the pest control agent is generally diluted with water for an application in order to have a concentration of the active ingredient from 0.01 to 10,000 ppm, and powder, granule and similar formulations are usually applied as such.
[00182] These formulations and formulation solutions diluted with water can be applied directly because they are sprayed on a pest or a plant, such as crops that should be protected against pests, and can also be applied to a soil to control a pest that infests the soil of the cultivated land.
[00183] In addition, the resin formulation processed on a plate or fiber can also be applied by a method such as wrapping it around the crops, spreading them in the vicinity of the crops or spreading them in the soil around the roots of the cultures.
[00184] When the pest control agent of the present invention is used to control the pest that lives in the house, the amount of application normally ranges from 0.01 to 1000 mg in an amount of the compound of the present invention per 1 m2 of a area to be treated, if used in a flat area, and is normally equal to 0.01 to 500 mg, in an amount of the compound of the present invention per 1 m3 of a space to be treated, in the case of use it in a space. When the pest control agent of the present invention is formulated in an emulsifiable concentrate, wettable powder, flowable or similar, the pest control agent is usually diluted with water for an application in order to achieve a concentration of the active ingredient in 0.1 to 10,000 ppm, and oily formulations, aerosols, smoking agents, poisonous bait formulations and the like are applied as such.
[00185] When the arthropod pest control agent of the present invention is used to control external parasites in animals such as cows, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, methods known veterinarians can be applied to animals. As specific methods, the formulation is administered, for example, by means of a tablet, mixed with food, a suppository and injection (intramuscular, subcutaneous, intravenous, intraperitoneal injections, etc.), when systemic control is intended, and the formulation it is used, for example, by spraying an oily solution or an aqueous solution, spill or spot treatment, washing an animal with a shampoo formulation, or by placing a collar or ear tag made from a formulation resin for an animal, when non-systemic control is intended. The amount of the compound of the present invention, when administered to an animal body, is generally in the range of 0.1 to 1000 mg per 1 kg of an animal's weight.
[00186] The pest control agent of the present invention can be used on land where the following "crops" are grown.
[00187] Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soy, peanuts, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc.
[00188] Vegetables: solanaceous vegetables (eggplant, tomatoes, peppers, peppers, potatoes, etc.), cucurbits (cucumbers, squash, zucchini, watermelons, melons, etc.), cruciferous legumes (Japanese radish, turnip, horseradish, kohlrabi, chinese cabbage, cabbage, brown mustard, broccoli, cauliflower, etc.), Compositae legumes (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae legumes (welsh onion, onion, garlic, asparagus , etc.), Umbelliferae legumes (carrots, parsley, celery, parsnips, etc.), Chenopodiaceae le-legumes (spinach, Swiss chard, etc.), Labiatae legumes (Japanese mint, mint, basil, etc.), strawberry, sweet potato, yam, aracea, etc.
[00189] Fruit trees: from seed fruits (apple, common pear, Japanese pear, Chinese quince, quince, etc.), fleshy fruit with stones and fleshy fruit with stones (peach, plum, nectarine, Japanese plum, cherry, apricot, prune, etc.), citrus plants (satsuma tangerine, orange, lemon, lemon, grapefruit, etc.), walnuts (chestnut, walnut, hazelnut, almond, pistachio, cashew, macadamia, etc. .), berries (blueberry, blackberry, blackberry, raspberry, etc.), grape, persimmon, olive, loquat, banana, coffee, date, coconut, palm oil, etc.
[00190] Trees other than fruit trees: tea, blackberry, flower and shrub trees (azalea, camellia, hydrangea, sasanqua, Illicium religiosum, cherry, tulip, myrtle, fragrant olive, etc.), used trees in urban afforestation (ash, birch, cornice, eucalyptus, ginkgo, lilac, maple, oak, poplar, Cercis, Chinese liquidambar, plane tree, Zelkova, Japanese arborvitae, fir tree, Japanese hemlock, juniper needle, pine, fir , yew, elm, horse chestnut, etc.), sweet viburnum, Podocarpus macrophyllus, Japanese cedar, Japanese cypress, croton, common axis tree, Japanese photinia, etc. [00191] Grasses: emerald grass (Japanese lawn, mascarene grass, etc.), Bermuda grass (Cynodon dactylon, etc.), agrostis (crawling agrostis, Agrostis stolonifera, Agrostis tenuis, etc.), bluegrass (fennel herb) , common poa, etc.), fescue (fescue of the meadows, fes-tuca-Vermelha-das-dunas, crawling fescue, etc.), ryegrass (chaff, perennial ryegrass, etc.), Pé de cock, tail -cat, etc.
[00192] Other species: flowers (rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners (prairie gentian), gypsophils, gerbera, chandelier, sage, petunia, verbena, tulip, aster, gentian, lily, pansy , orchid, lily of the valley, lavender, ornamental cabbage, primrose, christmas flower, gladiolus, cattleya, daisy, cymbidium, begonia, etc.), biofuel plants (Jatropha, curcas, saffron, camphor alyssum, switchgrass , miscanthus, spotted reed, cane, kenaf, cassava, willow, algae, etc.), foliage plants, etc.
[00193] "Cultures" also includes genetically modified crops.
[00194] The pest control agent of the present invention can be used as a mixture with or in combination with other insecticides, miticides, nematicides, fungicides, plant development regulators, herbicides or synergists. Examples of the active ingredient of said insecticide, miticide, nematicide, fungicide, herbicide and synergist are shown below.
Insecticide Active Ingredients (1) Organic Phosphorus Compounds Acephate, Aluminum Phosphide, Butathiophes, Cadusaphous, Chloroxyphos, Chlor-Fenvinfos, Chlorpyrifos, Chlorpyrifos-Methyl, Cyanophos: CYAP, diazinon, DCIP (dichlorodi-isopropyl ether), dicl , dichlorvos: DDVP, dime-toate, dimethylvinfos, disulfoton, EPN, etio, etoprofos, etrimfos, fentião: MPP, fenitrotião: MEP fostiazato, formotião, hydrogen phosphide, isophenphos, isoxation, malation, mesulfenfos, metulfenfos, metides: monocroto-fos, nalede: BRP, oxideprofos: ESP paratipon, fosalone, phosmete: PMP, pirimiphos-methyl, pyridafention, quinalfos, fentoate: PAP profenofos, pro-paphos, protiofos, pirachlorfos, salition, sulprofos, tebupirimfos, tefupirimfos, temefovirofos, temefovirofos, temefovirofos, temefovirofos, temefovirfos, temefovimofos, temefovirfos terbufos, tiometon, triclorfon: DEP, vamidotion, forato and cadusafos. (2) Carbamate compounds alanicarb, bendiocarb, benfuracarb, BPMC, carbearyl, carbeofuran, carbeosulfan, cloetocarb, etiofencarb, phenobucarb, phenothio-carb, phenoxycarb, furatiocarb, isoprocarb: MIPC, metolcarb, metolcarb, metolcarb, metaccarb oxamil, pirimicarb, propoxur: PHC, XMC, thiodicarb, xylilcarb and aldicarb. (3) Pyrethroid compounds acrinatrine, alletrin, benflutrin, beta-cyfluthrin, bifenthrin, cycloprotrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, sphenoperine, eto-fenprox, fenpropatrin, fluvitrinate, flucitrinate, flucitrinate, flucitrinate, flucitrinate, flucitrinate, flucitrinate, flucitrinate, flucitrinate, flucitrinate, flucitrinate. , permethrin, pralethrin, pyrethrins, resmetrin, sigma-cypermethrin, silafluofen, teflutrin, tralometrine, transflutrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, tama-cihalotin, furma-cihalotin, furma-cihalotin, furma-cihalotin, furma-cihalotin, gamma-cihalotin, furma-cihalotin, , proflutrin, dimeflutrin, 2,3,5,6-tetrafluor-4- (methoxymethyl) benzyl (EZ) - (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2 , 3,5,6-tetrafluor-4-methylbenzyl (EZ) - (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxy-late, 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) - 2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate, and 2,3,5,6-tetrafluor-4- (methoxymethyl la) benzyl (EZ) - (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-cyano-1-propenyl) cyclopropanecarboxylate, (4) Nereistoxine Cartape, bensultape, thiocyclam, monosultape and bissultape compounds. (5) Neonicotinoid compounds imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinote-furan and clothianidin. (6) Benzoylurea compounds chlorfluazuron, bistrifluron, diafentiuron, diflubenzuron, fluazuron, fluci-cloxuron, flufenoxuron, exaflumuron, lufenuron, novaluron, noviflumu-ron, teflubenzuron, triflubururon, trifluburon, trifluburon, trifluburon, trifluburon, trifluburon, , pyriprole and pirafluprol. (8) Bt Toxins Live spores derived from Bacillus thuringiensis and produced crystalline toxins, and mixtures thereof; (9) Hydrazine, chromafenozide, halofenozide, methoxyfenozide and tebufenozide compounds, (10) Organic Chlorinated Compounds aldrin, dieldrin, dienochlor, endosulfan and methoxychlor. (11) Other active ingredients of insecticides machine oil, nicotine sulfate; avermectin-B, bromopropylate, buprofezin, chlorfenapyr, cyantraniliprol, cyromazine, DD (1,3-dichloropro-peno) -emamectin-benzoate, phenazaquin, flupirazophos, hydroprene, metoprene, indoxacarbine, pyroxyamine, pyrimethazine, pyrimethoxine, pyrimethazine, pyrimethazine , spinosad, sulfluramid, tolfenpirade, triaza-mato, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanami, calcium polysulphide, chlordane, DDT, DSP, flufenerima, flo-nicamide, flurimfen, formethanate, methamide, methamidate, methamide, methamide, methamidate, -sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifene, sulfoxa-flower, sulfur, metaflumizone, spirotetramato, pyrifluquinazone, espine-toram, chlorantraniliprol, tralopyril, cyantraniliprol, compounds represented by the formula (K) below chlorine, bromine or a trifluoromethyl group, R200 represents chlorine, bromine or a methyl group, and R300 represents chlorine, bromine or a cyano group, and compounds represented by the formula (L) below in that R1000 represents chlorine, bromine or iodine.
Active ingredients of Miticida acequinocila, amitraz, benzoxide, biphenate, bromopropylate, cinomeionion, chlorobenzylate, CPCBS (chlorfenson), clofentezine, ciflumetofen, queltane (dicofol), ethoxazole, fenbutatin oxide, fluoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxyoxy , propargite: BPPS, polynactins, pyridaben, pyrimidifen, tebufenpirad, tetradifon, spirodiclofen, spiromesi-fen, spirotetramat, amidoflumet and cienopirafen.
Active ingredients of Nematicide DCIP, fosthiazate, levamisole, methisothiocyanate, morantel tartrate and imiciafos.
Fungicide active ingredients azole fungicidal compounds, such as propiconazole, protioconazole, tria-dimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, diphenoconazole, cyproconazole, metconazol, trifolazole, trifolazole, triflol , triticonazole, bitertanol, imazalil and flutriafol; fungicidal cyclic amine compounds, such as fenpropimorf, tridemorf and fenpropidina; benzimidazole fungicidal compounds, such as carbendezime, thiaben-dazol, benomyl and thiophanate-methyl; procymidone; cyprodinil; pyrimethanil; dietofencarb; tiuram; fluazinam; mancozeb; iprodione; vinclozoline; chlorothalonil; captan; mepanipirim; fenpiclonil; fludioxonil; diclofluanid; folpet; quresoxim-methyl; azoxis-trobin; trifloxystrobin; fluoxastrobin; picoxystrobin; piraclostrobin; dimo-xistrobin; piribencarb; spiroxamine; quinoxifen; fenexamid; famoxa-dona; fenamidone; zoxamide; etaboxam; amisulbrom; iprovalicarb; bentiavalicarb; cyazofamid; mandipropamid; boscalid; pentiopirad; me-trafenone; fluopyran; bixafen; ciflufenamid; proquinazid; isothianyl and tia-dinila.
Herbicide active ingredients (1) Herbicidal compounds of phenoxygraxo acid 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop and naproanilide. (2) 2,3,6-TBA benzoate herbicidal compounds, dicamba, clopyralid, picloram, aminopyralid, quinclorac and quinmerac, (3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebutiu-ron, metabenztiazuron, cumiluron, daimuron and methyl-daimuron, (4) Triazine herbicidal compounds atrazine, ametorin, cyanazine, simazine, propazine, simetrin, dimetame-trin, prometrin, metribuzin, triaziflam, and indaziflam. (5) Paraquat and diquat herbicidal bipyridine compounds. (6) Hydroxybenzonitrile bromoxynil and ioxynil herbicidal compounds. (7) Herbicidal compounds of dinimroaniline pendimethalin, prodiamine and trifluralin. (8) Amiprofos-methyl organophosphate herbicidal compounds, butamiphos, bensulide, piperophos, anilophos, glyphosate, glufosinate, glufosinate-P and bialaphos. (9) Herbicide compounds of carbamate dialate, trialate, EPTC, butylate, bentiocarb, esprocarb, molinate, di-mepiperate, swep, chlorprofam, fenmedipham, phenisofam, pyributicarb and asulam. (10) Herbicidal compounds of propanyl acid amide, propizamide, bromobutide and etobenzanide. (11) Herbicidal compounds of chloroacetanilide acetochlor, alachlor, butachlor, dimethenamide, propachlor, metazachlor, methoxychlor, pretilachlor, tenilchlor and petoxamid. (12) Diphenyl acifluorfen-sodium etheric herbicidal compounds, bifenox, oxyfluorphene, lactophen, fomessafen, clo-methoxyinyl and aclonifene, (13) Cyclic imide herbicide compounds oxadiazon, cinidon-ethyl, carfentrazone-ethyl, flentrazone-ethyl, surfentrazone pentyl, flumioxazin, piraflufen-ethyl, oxadiargyl, pentoxazone, fluti-acet-methyl, butafenacil, benzfendizone, bencarbazone and saflufenacil. (14) Pyrazole benzofenap, pyrazolate, pyrazoxifen, topramezone and pirasulfotol herbicidal compounds. (15) Trichetone herbicidal compounds isoxaflutol, benzobicyclon, sulcotrione, mesotrione, tembotrione and tefuri-Itrione. (16) Herbicidal compounds of aryloxyphenoxypropionate clodinafop-propargyl, cihalofop-butyl, diclofop-methyl, phenoxaprop-ethyl, fluazifop-butyl, haloxifop-methyl and quizalofop-ethyl and metamifop. (17) Herbicidal compounds of alloxidim-sodium trione oxime, setoxidim, butroxidim, cletodim, cloproxidim, cycloxy-dim, tepraloxidim, tralquoxidim and profoxidim. (18) Chlorosulfuron, sulfometuron-methyl, methsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, tifensulfuron-methyl, pyrazosulfuron-ethyl, primisulfuron-methylsulfuron-methylsulfuron, sulfuryl-sulfonylurea, chlorosulfon-methylsulfonyl , rimsulfuron, halosulfuron-methyl, prosulfu-ron, etametsulfuron-methyl, triflusulfuron-methyl, flazasulfuron, ciclosul-famuron, flupirsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxa-sulfuron, metho-sulfuron, iodosulfuron, iodosulfuron , tritosulfuron, ortosulfamuron, flucetosulfuron and propyrisulfuron. (19) Midazolinone imazametabenz-methyl herbicidal compounds, imazametapyr, imazamox, imazapyr, imazaquin and imazetapyr. (20) Sulfonamide herbicidal compounds flumetsulame, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam and pyroxsulam. (21) Pyrimidinyloxybenzoate herbicidal compounds piritiobac-sodium, bispiribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid and pyrimisulfan. (22) Other herbicidal compounds bentazon, bromacila, terbacil, chlortiamid, isoxaben, dinoseb, amitrol, cinmetilin, tridifan, dalapon, diflufenzopir-sodium, dithiopir, thiazopyr, flu-carbazone-sodium, propoxycarbazone-sodium, flufenacetam, flefenacetam, cafenstrol, indanofan, oxazyclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picoli-nafen, beflubutamid, clomazone, amicarbazone, pinoxaden, pyraclonyl, pyroxasulfone, methacrylamine and aminocarbonate;
Synergistic Agent Active Ingredients piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinor-born-5-ene-2,3-dicarboximide (MGQU 264), N-decliimidazole ), WARF-antiresistant, Tribufos (TBPT), triphenyl phosphite (TPP), iprobenfos (IBP), methyl iodide (CH3I), t-phenylbutenone, diethylmaleate, bis (p-chloro-phenyl) methylcarbinol (DMC) and bis (p-chlorophenyl) trifluoromethyl carbinol (FDMC), EXAMPLES
[00195] Hereinafter, the present invention will be further described in detail with reference to production examples, formulation examples, test examples and the like. However, the present invention is not limited to these examples.
[00196] First, the production examples for the production of the compounds of the present invention are shown below.
Production Example 1 (1) [00197] To a mixture of 9.61 g of N2-methyl-5-trifluormethylpyridine-2,3-diamine (synthesized by a method described in WO2010-125985), 9.2 g of acid 3,5-dichloropyridine-2-carboxylic acid and 48 ml of pyridine, 9.64 g of EDCI hydrochloride and 0.64 g of HOBt were added, under refrigeration, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, and the precipitated solid was filtered. Ethyl acetate and water were added to the resulting solid and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to produce 15.73 g of 3,5-dichloro-N- (2-methylamino-5-trifluormethyl-pyridin-3-yl) -picolinamide. 3,5-dichloro-N- (2-methylamino-5-trifluormethylpyridin-3-yl) -picolinamide 1H NMR (CDCl3) ô: 9.33 (1H, brs), 8.51 (1H, d), 8, 37 (1H, d), 7.95 (1H, d), 7.86 (1H, d), 5.02 (1H, brs), 3.08 (3H, d).
Production Example 1 (2) [00198] A mixture of 15.73 g of 3,5-dichloro-N- (2-methylamino-5-trifluormethylpyridin-3-yl) -picolinamide and 43 ml of acetic acid was heated and stirred at 130 ° C for 4 hours. The chilled reaction mixture was added to the water, and the precipitated solid was filtered. Ethyl acetate and saturated aqueous sodium bicarbonate solution were added to the resulting solid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to produce 14.47 g of 2- (3,5-dichloropyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4, 5-b] pyridine. 2- (3,5-dichloropyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine 1H NMR (CDCl3) ò: 8.76 (1H, dd), 8 , 67 (1H, d), 8.40 (1H, dd), 8.01 (1H, d), 3.98 (3H, s).
Production Example 1 (3) [00199] A mixture of 1.1 ml of ethyl mercaptan and 5 ml of THF was added to a mixture of 5.0 g of 2- (3,5-dichloropyridin-2-yl) - 3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine, 0.63 g of 60% sodium hydride (oily) and 30 ml of THF for 30 minutes, and the mixture was stirred at room temperature room for 2 hours. The reaction mixture was added to the ice water, and the precipitated solid was filtered. The resulting solid was washed with water and hexane and dried under reduced pressure to produce 5.19 g of 2- (5-chloro-3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4 , 5-b] pyridine. 2- (5-chloro-3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine 1H NMR (CDCl3) ô: 8.74 (1H, dd) , 8.45 (1H, d), 8.40 (1H, dd), 7.72 (1H, d), 4.07 (3H, s), 2.98 (2H, q), 1.39 ( 3H, t).
Production Example 1 (4) [00199] To a mixture of 15.48 g of 2- (5-chloro-3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5 -b] pyridine and 208 ml of chloroform were added 21.96 g of m-chloroperbenzoic acid (purity equal to or greater than 65%), under refrigeration, and then the mixture was stirred at room temperature for 6.5 hours. A 10% aqueous sodium thiosulfate solution and a saturated sodium bicarbonate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then it was concentrated under reduced pressure. Ethyl acetate and hexane were added to the resulting crude product, and the precipitated solid was filtered and dried under reduced pressure to produce 12.94 g of 2- (5-chloro-3-ethylsulfonylpyridin-2-yl) -3-methyl- 6-trifluor-methyl-3H-imidazo [4,5-b] pyridine. 2- (5-chloro-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine 1H NMR (CDCl3) ô: 8.95 (1H, dd) , 8.77 (1H, dd), 8.53 (1H, dd), 8.32 (1H, dd), 3.94-3.86 (5H, m), 1.40 (3H, t).
Production Example 1 (5) [00200] To a mixture of 7.25 g of 2- (5-chloro-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5 -b] pyridine and 40 ml of NMP 1.52 g of sodium azide was added, and the mixture was stirred at 90 ° C for 4 hours. A saturated aqueous sodium bicarbonate solution was added to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate and concentrated under reduced pressure to produce 2- (5-azido-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H -imidazo [4,5-b] pyridine.
[00201] A mixture of the entire amount of 2- (5-azido-3-ethylsulfo-nilpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine produced above, 6 , 12 g of triphenylphosphine, 73 ml of THF and 7 ml of water were stirred at room temperature for 5.5 hours. 1 ml of concentrated hydrochloric acid was added to the reaction mixture, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then it was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 4.68 g of 2- (5-amino-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4, 5-b] pyridine. 2- (5-amino-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine 1H NMR (CDCl3) ô: 8.72 (1H, dd) , 8.36 (1H, d), 8.27 (1H, dd), 7.70 (1H, d), 4.36 (2H, brs), 3.84 (3H, s), 3.81 ( 2H, q), 1.36 (3H, t).
Production Example 1 (6) [00202] To a mixture of 0.15 g of 2- (5-amino-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5 -b] pyridine, 2 ml of chloroform and 0.1 ml of diisopropylethylamine, 0.03 ml of methanesulfonyl chloride was added under refrigeration, and the mixture was stirred at room temperature for 4 hours. 0.07 ml of diisopropylethylamine and 0.03 ml of methanesulfonyl chloride were added to the reaction mixture, under refrigeration, and the mixture was stirred at room temperature for 4 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then it was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 0.18 g of N- [5-ethylsulfonyl-6- (3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridin-2 -yl) -pyridin-3-yl] -methylsulfonimide (hereinafter referred to as the Compound of the Present Invention 2).
Compound of the Present Invention 2 1 H NMR (CDCh) ô: 8.95 (1H, d), 8.79 (1H, d), 8.52 (1H, d), 8.33 (1H, d), 3, 96 (3H, s), 3.93 (2H, q), 3.51 (6H, s), 1.40 (3H, t).
Production Example 2 [00203] To a mixture of 0.15 g of 2- (5-amino-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine, 2 ml of DMF and 0.2 ml of diisopropylethylamine 0.1 ml of propargyl chloroformate was added under refrigeration, and the mixture was stirred at room temperature for 4 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then it was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 0.08 g of N '- [5-ethylsulfonyl-6- (3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridin- 2-yl) -pyridin-3-yl] -N, N-dimethylformamidine (hereinafter referred to as the Compound of the Present Invention 3).
Compound of the Present Invention 3 1 H NMR (CDCl 3) δ: 8.73 (1H, d), 8.60 (1H, d), 8.28 (1H, d), 7.98 (1H, d), 7, 76 (1H, s), 3.85 (3H, s), 3.81 (2H, q), 3.17 (3H, s), 3.14 (3H, s), 1.36 (3H, t ). Production Example 3 [00204] To a mixture of 0.15 g of 2- (5-amino-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine and 2 ml of chloroform, 0.07 ml of methanesulfonic anhydride was added, under refrigeration, and the mixture was stirred at room temperature for 6 hours. 0.07 ml of diisopropylethylamine and 0.03 ml of methanesulfonyl chloride were added to the reaction mixture, under refrigeration, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then it was concentrated under reduced pressure. To the resulting residue were added 2 ml of chloroform, 0.01 ml of pyridinaq and 0.01 ml of methanesulfonyl chloride, and the mixture was stirred at room temperature for 9 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then it was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 0.08 g of N- [5-ethylsulfonyl-6- (3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridin-2 -yl) -pyridin-3-yl] -methylsulfo-namide (hereinafter referred to as the Compound of the Present Invention 4). Compound of the Present Invention 4 1H NMR (CDCl3) ô 8.86 (1H, d), 8.76 (1H, d), 8.32-8.30 (2H, m), 3,953.87 (5H, m) , 3.25 (3H, s), 1.39 (3H, t).
Production Example 4 [00205] To a mixture of 0.15 g of 2- (5-amino-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyridine and 2 ml of pyridine 0.07 ml of dimethylcarbamoyl chloride was added, under refrigeration, and the mixture was stirred at reflux under heating for 4 hours. Water was added to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 0.03 g of 3- [5-ethylsulfonyl-6- (3-methyl-6-trifluormethyl-3H-imidazo [4,5-b] pyri-din -2-yl) -pyridin-3-yl] -1,1-dimethylurea (hereinafter referred to as the Compound of the Present Invention 5).
Compound of the Present Invention 5 1H NMR (CDCl3) ô 9.22 (1H, dd), 8.74 (1H, dd), 8.50 (1H, dd), 8.29 (1H, dd), 6.85 (1H, brs), 3.92-3.82 (5H, m), 3.12 (6H, s), 1.38 (3H, t).
Production Example 5 (1) [00206] To a mixture of 5.0 g of 3,6-dichloropicolinic acid, 0.1 ml of DMF and 52 ml of toluene was added 3.8 ml of thionyl chloride, and to The mixture was stirred under reflux under heating for 3 hours. The reaction mixture cooled to room temperature was concentrated under reduced pressure to produce 3,6-dichloropicolinoyl chloride.
[00207] A mixture of 3,6-dichloropicolinyl chloride produced above and 5 mL of THF was added to a mixture of 5.7 g of 2-amino-4-trifluormethylsulfanylphenol and 52 mL of THF, under refrigeration, and the mixture it was stirred at room temperature for 6 hours. Water and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 8.94 g of 3,6-dichloro-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide. 3,6-dichloro-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide 1H NMR (CDCl3) ô: 9.92 (1H, s), 8.95-8.88 (1H, m), 7.92-7.85 (1H, m), 7.69-7.65 (1H, m), 7.53-7.48 (1H, m), 7.48-7.40 (1H, m ), 7.12-7.05 (1H, m).
Production Example 5 (2) [00208] To a mixture of 8.94 g of 3,6-dichloro-N- [2-hydroxy-5- (trifluormethylsulfanyl) phenyl] picolinamide, 47 ml of THF and 7.34 g of triphenylphosphine 7.10 g of di-2-methoxyethylazodicarboxylate (hereinafter referred to as DMEAD) were added, under refrigeration, and the mixture was stirred at room temperature overnight. Water and a saturated aqueous ammonium chloride solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 6.39 g of 2- (3,6-dichloropyridin-2-yl) -5- (trifluormethylsulfanyl) benzoxazole. 2- (3,6-dichloropyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole 1H NMR (CDCl3) ô 8.25 (1H, s), 7.91 (1H, d), 7.79-7, 72 (2H, m), 7.48 (1H, d).
Production Example 5 (3) [00209] To a mixture of 6.39 g of 2- (3,6-dichloropyridin-2-yl) -5- (tri-fluoromethylsulfanyl) benzoxazole and 45 ml of THF was added 0, 84 g of 60% sodium hydride (oily), and then a mixture of 1.29 ml of ethyl mercaptan and 4 ml of THF was added to this over 30 minutes, under refrigeration, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added to the ice water, and the precipitated solid was filtered. The resulting solid was washed with water and hexane, and dried under reduced pressure to yield 6.06 g of 2- (6-chloro-3-ethylsulfanylpyridin-2-yl) -5- (trifluormethylsulfanyl) benzoxazole. 2- (6-chloro-3-ethylsulfanylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole 1H NMR (CDCl3) ô 8.26 (1H, s), 7.77-7.69 (3H, m), 7.44 (1H, d), 3.06 (2H, q), 1.47 (3H, t).
Production Example 5 (4) [00210] To a mixture of 6.06 g of 2- (6-chloro-3-ethylsulfanylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole and 45 ml of chloroform were added 7, 13 g of m-chloroperbenzoic acid (purity equal to or greater than 65%), under refrigeration, and then the mixture was stirred for 4 hours under refrigeration. A 10% aqueous sodium thiosulfate solution and a saturated sodium bicarbonate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 4.24 g of 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluormethylsulfanyl) benzoxazole and 0.68 g of 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfinyl) benzoxazole. 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole 1H NMR (CDCl3) ô: 8.52 (1H, d), 8.18 (1H, s), 7.80 -7.72 (3H, m), 4.03 (2H, d), 1.43 (3H, t). 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfinyl) benzoxazole 1H NMR (CDCl3) ô: 8.53 (1H, d), 8.36 (1H, s), 7.94 (1H, d), 7.89 (1H, d), 7.76 (1H, d), 4.01 (2H, q), 1.44 (3H, t).
Production Example 5 (5) [00211] A mixture of 0.30 g of 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluormethylsulfanyl) benzoxazole, 0.14 ml of tetrahydrofurfurylamine, 0.24 ml of diisopropylethylamine and 0.5 ml of NMP was stirred at room temperature for 1 day. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to produce 0.28 g of [5-ethylsulfonyl-6- (5-trifluormethylsulfinylbenzoxa-zol-2-yl) -pyridin-2-yl] - (tetra -hydrofuran-2-ylmethyl) -amine (hereinafter referred to as the Compound of the Present Invention 36).
Compound of the Present Invention 36 1 H NMR (CDCl 3) δ 8.30 (1H, s), 8.07 (1H, d), 7.89-7.84 (2H, m), 6.65 (1H, d) , 5.67 (1H, s), 4.12-4.10 (1H, m), 3.91-3.88 (1H, m), 3.79-3.73 (4H, m), 3 , 39-3.32 (1H, m), 2.06-2.01 (1H, m), 1.98-1.90 (2H, m), 1.651.60 (1H, m), 1.38 (3H, t).
Production Example 6 (1) [00212] To a mixture of 10.0 g of 3,6-dichloropicolinic acid, 0.16 ml of DMF and 90 ml of toluene was added 7.20 ml of thionyl chloride, and to The mixture was stirred under reflux under heating for 2 hours. The reaction mixture was cooled to room temperature and was concentrated under reduced pressure to produce 10.88 g of 3,6-dichloropicolinoyl chloride.
[00213] A mixture of 3,6-dichloropicolinyl chloride produced above and 60 mL of THF was added to a mixture of 8.79 g of 2-amino-4-trifluoromethylsulfanylphenol and 40 mL of THF, under refrigeration, and the mixture it was stirred at room temperature for 3 hours. Water and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 16.22 g of 3,6-dichloro-N- [2-hydroxy-5- (trifluormethyl) phenyl] picolinamide. 3,6-dichloro-N- [2-hydroxy-5- (trifluormethyl) phenyl] picolinamide 1H NMR (CDCl3) ô 9.96 (1H, s), 8.82 (1H, s), 7.89 (1H , d), 7.62 (1H, d), 7.52 (1H, d), 7.44 (1H, dd), 7.14 (1H, d).
Production Example 6 (2) [00214] A mixture of 10.0 g of 3,6-dichloro-N- [2-hydroxy-5- (trifluoromethyl) phenyl] picolinamide, 1.08 g of p- toluenesulfonic monohydrate and 40 ml of xylene was stirred under reflux under heating for 3 hours during dehydration using a Dean-Stark apparatus. Water and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the resulting residue, 20 ml of isopropanol were added, and the mixture was stirred at 60 ° C for 2 hours and at room temperature for 1 hour. The precipitated solid was filtered to yield 6.19 g of 2- (3,6-dichloropyridin-2-yl) -5- (trifluormethyl) benzoxazole. 2- (3,6-dichloropyridin-2-yl) -5- (trifluoromethyl) benzoxazole 1H NMR (CDCl3) ô 8.22 (1H, s), 7.92 (1H, d), 7.81 (1H, d), 7.75 (1H, d), 7.49 (1H, d).
Production Example 6 (3) [00215] To a mixture of 7.50 g of 2- (3,6-dichloropyridin-2-yl) -5- (trifluormethyl) benzoxazole and 32 ml of THF was added 1.08 g of 55% sodium hydride (oily), then 1.67 ml of ethyl mercaptan was added to this over 30 minutes, under refrigeration, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added to the ice water, and the precipitated solid was filtered. The resulting solid was washed with water and hexane, and dried under reduced pressure to produce 6.46 g of 2- (6-chloro-3-ethylsulfanylpyridin-2-yl) -5- (trifluormethyl) benzoxazole. 2- (6-chloro-3-ethylsulfanylpyridin-2-yl) -5- (trifluoromethyl) benzoxazole 1H NMR (CDCl3) ô 8.23 (1H, s), 7.80 (1H, d), 7.74 ( 1H, d), 7.71 (1H, d), 7.44 (1H, d), 3.06 (2H, q), 1.47 (3H, t).
Production Example 6 (4) [00216] To a mixture of 2.0 g of 2- (6-chloro-3-ethylsulfanylpyridin-2-yl) -5- (trifluormethyl) benzoxazole and 20 ml of chloroform were added 2, 82 g of m-chloroperbenzoic acid (purity equal to or greater than 65%), under refrigeration, and then it was stirred at room temperature overnight. A 10% aqueous sodium thiosulfate solution and a saturated sodium bicarbonate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to produce 2.04 g of 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluormethyl) benzoxazole. 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethyl) benzoxazole 1H NMR (CDCl3) ô: 8.53 (1H, d), 8.15 (1H, s), 7.83 -7.72 (3H, m), 4.02 (2H, q), 1.44 (3H, t).
Production Example 6 (5) [00217] To a mixture of 0.20 g of 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethyl) benzoxazole, 77 mg of 6-chloro-3 -pyridinomethylamine and 2 ml of NMP, 79 mg of diisopropylethylamine were added, and the mixture was stirred at room temperature for 5 hours. Thereafter, 90 mg of 6-chloro-3-pyridinomethylamine were added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, under refrigeration, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 0.22 g of (6-chloropyridin-3-yl) - [5-ethylsulfonyl-6- (5-trifluormethylben-zoxazol-2-yl) -pyridin- 2-yl] amine (hereinafter referred to as the Compound of the Present Invention 38).
Compound of the Present Invention 38 1H NMR (CDCl3) ô: 8.42 (1H, d), 8.15 (1H, d), 8.12 (1H, d), 7.78-7.67 (3H, m ), 7.32 (1H, d), 6.65 (1H, d), 5.61 (1H, s), 4.69 (2H, d), 3.80 (2H, q), 1.39 (3H, t).
Production Example 7 [00218] To a mixture of 0.25 g of 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluormethyl) benzoxazole, 80 mg of O-methylhydroxyl hydrochloride mine and 2 ml of NMP, 194 mg of triethylamine was added, and the mixture was stirred at room temperature for 4 hours, and then it was stirred at 40 ° C for 2 hours. 0.26 g of O-methylhydroxylamine hydrochloride and 0.87 g of diisopropylethylamine were added to the reaction mixture at room temperature, and the mixture was stirred at 40 ° C for 6 hours. Water was added to the reaction mixture, under refrigeration, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 0.14 g of N- [5-ethylsulfonyl-6- (5-trifluormethylbenzoxazol-2-yl] -pyridin-2-yl] amino-O-methyl- hydroxylamine (hereinafter referred to as the Compound of the Present Invention 42).
Compound of the Present Invention 42 1 H NMR (CDCl 3) δ: 8.39 (1H, dd), 8.12 (1H, d), 7.99 (1H, s), 7.75 (1H, d), 7, 72 (1H, dd), 7.21 (1H, d), 3.89-3.83 (5H, m), 1.41 (3H, t).
Production Example 8 (1) [00219] To a mixture of 1.0 g of 2- (6-chloro-3-ethylsulfonylpyridin-2-yl) -5- (trifluormethyl) benzoxazole and 6.5 ml of NMP 1.55 ml of a 28% aqueous ammonia solution, and the mixture was stirred at room temperature for one day. 1.55 ml of a 28% aqueous ammonia solution was added to the reaction mixture, and the mixture was stirred at room temperature for one day. Water was added to the reaction mixture and the precipitated solid was filtered and dried under reduced pressure. The resulting residue was subjected to silica gel column chromatography to produce 0.14 g of 5-ethylsulfonyl-6- (5-trifluormethylbenzoxazol-2-yl) -pyridin-2-ylamine. 5-ethylsulfonyl-6- (5-trifluoromethylbenzoxazol-2-yl) -pyridin-2-ylamine 1H NMR (CDCh) ô: 8.18 (1H, d), 8.11 (1H, d), 7.75 ( 1H, d), 7.71 (1H, d), 6.74 (1H, d), 5.22 (2H, s), 3.82 (2H, q), 1.40 (3H, t).
Production Example 8 (2) [00220] To a mixture of 0.20 g of 5-ethylsulfonyl-6- (5-trifluormethyl-benzoxazol-2-yl) -pyridin-2-ylamine and 5 ml of toluene was added , 72 mL of N, N-dimethylformamitymethylacetal, and the mixture was stirred under reflux for 3 hours. The reaction mixture cooled to room temperature was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to produce 0.20 g of N '- [5-ethylsulfonyl-6- (5-trifluormethylbenzoxazole-2 -yl] -pyridin-2-yl] -N, N-dimethylformamidine (hereinafter referred to as the Compound of the Present Invention 58).
Compound of the Present Invention 58 1H NMR (CDCl3) ô: 8.64 (1H, s), 8.22 (1H, d), 8.11 (1H, d), 7.75 (1H, d), 7, 71 (1H, d), 7.16 (1H, d), 3.77 (2H, q), 3.16 (6H, s), 1.39 (3H, t).
[00221] The compounds described in the production examples described above and the compounds produced by the production method according to the method described in the production examples described above are shown in [Table 20] through [Table 23].
[00222] The compounds of the present invention represented by formula (1B): where A1, A2, A3, R1, R2, R3, R4, G and n represent the combinations shown in [Table 22] to [Table 23] shown below.
[00223] The compounds of the present invention represented by formula (1C): where A1, A2, A3, R1, R2, R3, R4, G and n represent the combinations shown in [Table 24] to [Table 25] shown below.
[Table 24] [00224] 1H NMR data of the compound of the present invention shown in [Table 22] through [Table 25] are shown below.
Compound of the Present Invention 1 1 H NMR (CDCl 3) δ 9.06 (1H, d), 8.74 (1H, d), 8.59 (1H, d), 8.29 (1H, d), 7.46 -7.37 (5H, m), 7.30 (1H, brs), 5.28 (2H, s), 3.86 (3H, s), 3.83 (2H, q), 1.35 ( 3H, t).
Compound of the Present Invention 6 1H NMR (CDCl3) ô: 9.39 (1H, d), 9.29 (1H, brs), 8.78-8.76 (2H, m), 8.31 (1H, dd ), 4.50 (2H, q), 3.93-3.87 (5H, m), 1.48 (3H, t), 1.40 (3H, t).
Compound of the Present Invention 7 1 H NMR (CDCl 3) δ: 9.51 (1H, d), 8.75 (1H, d), 8.59 (1H, d), 8.30 (1H, d), 8, 29 (1H, s), 3.94 (2H, q), 3.89 (3H, s), 2.84-2.74 (1H, m), 2.02-1.87 (4H, m) , 1.84-1.74 (2H, m), 1.68-1.58 (2H, m), 1.40 (3H, t).
Compound of the Present Invention 8 1 H NMR (CDCl 3) δ: 9.52 (1H, d), 8.76 (1H, d), 8.58 (1H, d), 8.31 (1H, d), 8, 09 (1H, s), 3.94 (2H, q), 3.89 (3H, s), 3.31-3.20 (1H, m), 2.48-2.37 (2H, m) , 2.31 - 2.20 (2H, m), 2.07 - 1.92 (2H, m), 1.40 (3H, t).
Compound of the Present Invention 9 1 H NMR (CDCl 3) δ: 8.72 (1H, d), 8.42 (1H, d), 8.27 (1H, d), 7.77 (1H, d), 4, 83 (1H, brs), 3.85-3.78 (5H, m), 2.66-2.58 (1H, m), 1.37 (3H, t), 1,000.92 (2H, m) , 0.69-0.63 (2H, m).
Compound of the Present Invention 10 1 H NMR (CDCl 3) ô: 9.62 (1H, s), 8.77 (1H, d), 8.67 (1H, d), 8.39-8.36 (1H, m ), 8.31 (1H, d), 8.18 (1H, d), 7.54-7.52 (1H, m), 6.84 (1H, d), 3.96 (2H, q) , 3.92 (3H, s), 1.39 (3H, t).
Compound of the Present Invention 11 1 H NMR (CDCl 3) δ: 8.80 (1H, d), 8.77 (1H, d), 8.37 (1H, d), 8.32 (1H, d), 3, 93-3.84 (5H, m), 1.51 (18H, s), 1.38 (3H, t).
Compound of the Present Invention 12 1H NMR (CDCl3) ô: 9.59 (1H, d), 8.83 (1H, s), 8.79-8.75 (2H, m), 8.31 (1H, d ), 7.60 (1H, d), 7.38 (1H, d), 6.63 (1H, dd), 3.93 (2H, q), 3.92 (3H, s), 1.39 (3H, t).
Compound of the present invention 13 1 H NMR (CDCl 3) δ: 9.05 (1H, d), 8.77 (1H, d), 8.45 (1H, d), 8.31 (1H, d), 3, 95-3.86 (5H, m), 3.52 (3H, s), 3.05 (3H, s), 1.40 (3H, t).
Compound of the present invention 14 1 H NMR (CDCl 3) δ: 9.46 (1H, d), 9.44 (1H, brs), 8.78-8.75 (2H, m), 8.31 (1H, d ), 4.04 (3H, s), 3.93 (2H, q), 3.91 (3H, s), 1.40 (3H, t).
Compound of the present invention 15 1 H NMR (CDCl 3) δ: 8.74 (1H, d), 8.53 (1H, d), 8.28 (1H, d), 7.89 (1H, d), 6, 80 (1H, brs), 6.32 (1H, brs), 3.87-3.79 (8H, m), 1.36 (3H, t).
Compound of the present invention 16 1 H NMR (CDCl 3) δ: 10.20 (1H, s), 9.31 (1H, d), 8.91 (1H, d), 8.76 (1H, dd), 8, 31 (1H, dd), 3.91 - 3.85 (5H, m), 3.56 (3H, s), 3.17 (3H, s), 1.39 (3H, t).
Compound of the present invention 17 1 H NMR (CDCl 3) δ 9.00 (1H, d), 8.76 (1H, d), 8.44 (1H, d), 8.30 (1H, d), 3.92 (3H, s), 3.87 (2H, q), 3.28-3.21 (1H, m), 2.51 (3H, s), 1.40 (3H, t), 1.28- 1.20 (2H, m), 0.80-0.74 (2H, m).
Compound of the present invention 18 1 H NMR (CDCl 3) δ: 9.04 (1H, d), 8.76 (1H, d), 8.48 (1H, d), 8.30 (1H, d), 3, 91 (3H, s), 3.89-3.82 (5H, m), 3.15-3.12 (1H, m), 1.39 (3H, t), 1,151.09 (2H, m) , 0.71-0.65 (2H, m).
Compound of the present invention 19 1H NMR (CDCl3) δ 8.72 (1H, d), 8.47 (1H, d), 8.28 (1H, d), 7.88 (1H, d), 6.12 (1H, brs), 3.86-3.77 (7H, m), 1.36 (3H, t).
Compound of the present invention 20 NMR 1H (CDCl3) δ 8.72 (1H, dd), 8.29-8.26 (2H, m), 7.57 (1H, d), 4.96 (1H, t) , 4.01-3.68 (9H, m), 3.28 (2H, dd), 2.67-2.58 (1H, m), 2.22-2.13 (1H, m), 1 , 77-1.68 (1H, m), 1.36 (3H, t).
Compound of the present invention 21 1 H NMR (CDCl 3) δ: 8.72 (1H, s), 8.42 (1H, s), 8.30 (1H, d), 8.27 (1H, s), 7, 69 (1H, dd), 7.61 (1H, d), 7.35 (1H, d), 5.44 (1H, t), 4.51 (2H, d), 3.89-3.77 (5H, m), 1.29 (3H, t).
Compound of the present invention 22 1 H NMR (CDCl 3) δ: 9.42 (1H, d), 9.19 (1H, s), 8.75 (1H, d), 8.67 (1H, d), 8, 30 (1H, d), 3.93 (2H, q), 3.88 (3H, s), 1.69-1.62 (1H, m), 1.39 (3H, t), 1.14 -1.10 (2H, m), 0.93-0.87 (2H, m).
Compound of the present invention 23 1 H NMR (CDCl 3) δ: 9.39 (1H, d), 9.03 (1H, brs), 8.75 (1H, d), 8.71 (1H, d), 8, 30 (1H, d), 4.55 (1H, dd), 4.14-4.07 (1H, m), 4.02-3.97 (1H, m), 3.92-3.85 ( 5H, m), 2.49-2.38 (1H, m), 2.26-2.17 (1H, m), 2.08-1.93 (2H, m), 1.39 (3H, t).
Compound of the present invention 24 1 H NMR (CDCl 3) δ: 10.53 (1H, s), 9.51 (1H, d), 8.94 (1H, d), 8.76 (1H, d), 8, 71-8.68 (1H, m), 8.37-8.33 (1H, m), 8.31 (1H, d), 8.03-7.98 (1H, m), 7.62- 7.58 (1H, m), 3.92-3.84 (5H, m), 1.42 (3H, t).
Compound of the present invention 25 1 H NMR (CDCl 3) δ: 8.71 (1H, d), 8.32-8.29 (1H, m), 8.25 (1H, d), 7.59- 7.57 (1H, m), 7.42-7.32 (5H, m), 5.00-4.88 (1H, m), 4.52-4.47 (2H, m), 3.83 (3H , s), 3.76 (2H, q), 1.26 (3H, t).
Compound of the present invention 26 1H NMR (CDCl3) δ: 8.71 (1H, d), 8.65-8.61 (1H, m), 8.42-8.40 (1H, m), 8.26 (1H, d), 7.78-7.72 (1H, m), 7.65 (1H, d), 7.35 (1H, d), 7.31-7.27 (1H, m), 6.14-6.08 (1H, m), 4.59 (2H, d), 3.86-3.76 (5H, m), 1.34 (3H, t).
Compound of the present invention 27 1 H NMR (CDCl 3) δ: 8.71 (1H, d), 8.67 (1H, d), 8.58 (1H, dd), 8.32 (1H, d), 8, 26 (1H, d), 7.74-7.70 (1H, m), 7.62 (1H, d), 7.34 (1H, dd), 5.30 (1H, t), 4.53 (2H, d), 3.83 (3H, s), 3.79 (2H, q), 1.28 (3H, t).
Compound of the present invention 28 1H NMR (DMSO-D6) δ: 11.25 (1H, s), 9.22 (1H, d), 8.89 (1H, d), 8.80 (1H, d), 8.38 (1H, d), 8.31 (1H, dd), 3.96 (2H, q), 1.94-1.84 (1H, m), 1.28 (3H, t), 1 , 02-0.88 (4H, m).
Compound of the present invention 29 1H NMR (DMSO-D6) ô: 10.83 (1H, brs), 9.13 (1H, d), 8.90 (1H, d), 8.80 (1H, d), 8.38 (1H, d), 8.31 (1H, dd), 3.99 (2H, q), 3.40-3.27 (6H, m), 1.32 (3H, t).
Compound of the present invention 30 1 H NMR (CDCl 3) δ 8.73 (1H, dd), 8.29 (1H, dd), 8.14 (1H, d), 6.73 (1H, d), 5.18 (3H, s), 3.85 (3H, s), 3.58 (2H, q), 1.31 (3H, t).
Compound of the present invention 31 1H NMR (CDCl3) δ: 8.72 (1H, s), 8.28 (1H, s), 8.19 (1H, d), 6.97 (1H, d), 5, 65 (1H, brs), 3.83 (3H, s), 3.58 (2H, q), 2.70-2.62 (1H, m), 1.32 (3H, t), 0.98 -0.92 (2H, m), 0.70-0.64 (2H, m).
Compound of the present invention 32 1H NMR (CDCl3) ô: 8.29 (1H, s), 8.24 (1H, d), 7.91-7.81 (2H, m), 7.01 (1H, d ), 5.79 (1H, s), 3.78 (2H, q), 2.70-2.61 (1H, m), 1.40 (3H, t), 0.980.90 (2H, m) , 0.70-0.62 (2H, m).
Compound of the present invention 33 1H NMR (CDCl3) ô: 8.31 (1H, s), 8.26 (1H, d), 7.92-7.80 (2H, m), 7.32 (1H, s ), 7.14 (1H, s), 6.97 (1H, d), 3.85-3.65 (5H, m), 1.39 (3H, t).
Compound of the present invention 34 1H NMR (CDCl3) δ: 8.30 (1H, s), 8.11 (1H, d), 7.88-7.85 (2H, m), 7.40- 7.30 (5H, m), 6.62 (1H, d), 5.74 (1H, s), 4.63 (2H, d), 3.77 (2H, q), 1.39 (3H, t) .
Compound of the present invention 35 1 H NMR (DMSO-D6) δ: 10.00 (1H, s), 8.38-8.36 (3H, m), 8.11 (1H, d), 7.97-7 , 95 (1H, m), 7.87-7.84 (3H, m), 7.22 (1H, d), 3.05 (2H, q), 1.27 (3H, t).
Compound of the present invention 37 1 H NMR (CDCl 3) δ: 8.30 (1H, s), 8.12 (1H, d), 7.93-7.84 (2H, m), 6.64 (1H, d ), 5.47 (1H, brs), 3.99-3.91 (1H, m), 3.88-3.82 (1H, m), 3.80-3.71 (3H, m), 3.68-3.62 (1H, m), 3.49-3.39 (2H, m), 2.67-2.56 (1H, m), 2,182.07 (1H, m), 1, 75-1.64 (1H, m), 1.39 (3H, t).
Compound of the present invention 39 1 H NMR (CDCl 3) δ: 8.44 (1H, d), 8.15 (1H, t), 8.12 (1H, d), 7.78-7.75 (2H, m ), 3.91 (2H, q), 3.72 (3H, s), 2.01-1.99 (1H, m), 1.42 (3H, t), 1.22-1.20 ( 2H, m), 1.00-0.98 (2H, m).
Compound of the present invention 40 1 H NMR (DMSO-D6) δ: 11.78 (1H, s), 8.43 (2H, d), 8.17 (1H, d), 7.95 (1H, d), 7.40 (1H, d), 3.79 (2H, q), 3.42 (3H, s), 1.25 (3H, t).
Compound of the present invention 41 1 H NMR (CDCl 3) δ 8.28 (1H, s), 7.89 (1H, d), 7.85 (2H, d), 6.83 (1H, d), 3.67 (2H, q), 3.09-3.01 (4H, m), 1.38-1.36 (9H, m).
Compound of the present invention 43 1 H NMR (CDCl 3) δ: 8.25 (1H, d), 8.11 (1H, t), 7.75 (1H, d), 7.71 (1H, dd), 7, 21 (1H, d), 3.82 (3H, s), 3.79 (2H, q), 3.44 (3H, s), 1.38 (3H, t).
Compound of the present invention 44 1 H NMR (CDCl 3) δ: 8.69 (1H, s), 8.56 (1H, d), 8.48 (1H, d), 8.17 (1H, d), 7, 76 (1H, dd), 7.69 (1H, d), 3.89 (2H, q), 1.61-1.59 (1H, m), 1.41 (3H, t), 1.19 -1.15 (2H, m), 0.99-0.97 (2H, m).
Compound of the present invention 45 1 H NMR (CDCl 3) δ: 9.07 (1H, s), 8.57 (1H, d), 8.47 (1H, d), 8.32 (1H, s), 7, 86 (1H, d), 7.78 (1H, d), 3.86 (2H, q), 1.71 to 1.69 (1H, m), 1.40 (3H, t), 1.18 -1.14 (2H, m), 0.98-0.96 (2H, m).
Compound of the present invention 46 1 H NMR (CDCl 3) δ: 8.40 (1H, d), 8.31 (1H, s), 8.11 (1H, d), 7.89 (1H, dd), 7, 86 (1H, dd), 7.68 (1H, dd), 7.31 (1H, d), 6.66 (1H, d), 5.77 (1H, s), 4.68 (2H, d ), 3.79 (2H, q), 1.39 (3H, t).
Compound of the present invention 47 1 H NMR (DMSO-D6) δ: 9.98 (1H, s), 9.01 (1H, d), 8.88 (1H, d), 8.77 (1H, d), 8.36 (1H, d), 8.30 (1H, d), 3.91 (2H, q), 1.27 (3H, t).
Compound of the present invention 48 1 H NMR (CDCl 3) δ: 8.49 (1H, d), 8.35 (1H, s), 7.90 (2H, s), 7.48 (1H, d), 3, 94 (2H, q), 3.40 (3H, s), 1.43 (3H, t).
Compound of the present invention 49 1H NMR (DMSO-D6) δ: 8.47 (1H, d), 8.25 (1H, dd), 8.09 (1H, d), 8.05 (1H, dd), 7.36 (1H, d), 3.66 (2H, q), 1.22 (3H, t).
Compound of the present invention 50 1 H NMR (CDCl 3) δ: 8.24 (1H, s), 7.83 (2H, d), 7.69 (2H, d), 7.52-7.50 (2H, m ), 7.42 (2H, t), 7.29-7.21 (5H, m), 6.58 (1H, d), 2.96 (2H, q), 1.38 (3H, t) .
Compound of the present invention 51 1 H NMR (CDCl 3) δ: 8.32 (1H, s), 8.24 (1H, d), 7.89-7.84 (2H, m), 7,527.44 (10H, m ), 6.80 (1H, d), 3.91 (2H, q), 1.36 (3H, t).
Compound of the present invention 52 1 H NMR (CDCl 3) δ: 8.23 (1H, t), 7.82 (1H, d), 7.78 (1H, d), 7.72 (1H, dd), 7, 49 (1H, d), 7.19 (1H, s), 3.27 (3H, s), 3.05 (2H, q), 1.44 (3H, t).
Compound of the present invention 53 1H NMR (CDCl3) δ: 8.20 (1H, t), 7.84 (2H, d), 7.74 (1H, d), 7.66 (1H, dd), 7, 52-7.51 (2H, m), 7.42 (2H, t), 7.30-7.22 (5H, m), 6.59 (1H, d), 2.96 (2H, q) , 1.37 (3H, t).
Compound of the present invention 54 1 H NMR (CDCl 3) δ: 8.23 (1H, d), 8.11 (1H, t), 7.76-7.70 (2H, m), 7.51- 7.35 (10H, m), 6.77 (1H, d), 3.93 (2H, q), 1.36 (3H, t).
Compound of the present invention 56 1H NMR (CDCl3) δ: 8.24 (1H, t), 7.80-7.78 (2H, m), 7.72 (1H, dd), 7.64 (1H, d ), 3.70 (3H, t), 3.07 (2H, q), 1.47 (3H, t).
Compound of the present invention 57 1 H NMR (CDCl 3) δ: 8.56 (1H, d), 8.16 (1H, s), 8.00 (1H, d), 7.79-7.78 (2H, m ), 3.96 (2H, q), 3.72 (3H, s), 1.44 (3H, t).
Compound of the present invention 59 1H NMR (CDCl3) ô: 8.26 (1H, s), 7.82 (1H, d, J = 8.9 Hz), 7.73 (2H, dd, J = 2.5 , 1.1Hz), 7.48 (1H, d, J = 8.9 Hz), 3.26 (3H, s), 3.05 (2H, q, J = 7.4 Hz), 1.45 (3H, t, J = 7.4 Hz).
Compound of the present invention 60 NMR 1H (CDCl3) ô: 8.33 (1H, d, J = 0.7 Hz), 8.13 (1H, d, J = 8.8 Hz), 7.91 (1H, dd, J = 8.6,0.5 Hz), 7.88 (1H, dd, J = 8.6.0.9 Hz), 7.48 (1H, s), 6.69 (1H, d , J = 9.1 Hz), 5.77 (1H, t, J = 6.0 Hz), 4.80 (2H, d, J = 5.9 Hz), 3.81 (2H, q, J = 7.5 Hz), 1.40 (3H, t, J = 7.4 Hz).
[00225] The following are examples of formulation of the compound of the present invention. Part means part by weight.
Formulation Example 1 [00226] 10 parts of any of the compounds of the present invention 1 to 60 are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, 14 parts of polyoxyethyl-styrene-phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added to this. The mixture is mixed to produce each emulsifiable concentrate.
Formulation Example 2 [00227] 4 parts of sodium lauryl sulfate, 2 parts of calcium lignosulfonate, 20 parts of fine powder of synthetic hydrated silicon oxide and 54 parts of diatomaceous earth are mixed, and 20 parts of any one of the compounds of the present invention 1 to 60 is added to that. The mixture is mixed to produce each wettable powder.
Formulation Example 3 [00228] 1 part fine powder of synthetic hydrated silicon oxide, 2 parts calcium lignosulfonate, 30 parts bentonite and 65 parts kaolin are added to 2 parts of any of the Compounds of the present invention 1 to 60. Subsequently, a suitable amount of water is added to this mixture, which is further agitated, granulated with a granulator and dried using forced air to produce each granule.
Formulation Example 4 [00229] 1 part of any of the Compounds of the Present Invention 1 to 60 is dissolved in an appropriate amount of acetone, and 5 parts of fine powder of synthetic hydrated silicon oxide, 0.3 part of PAP and 93.7 parts of Fubasami clay are added in addition. The mixture is sufficiently agitated and mixed to evaporate and remove the acetone, to produce each powder formulation.
Formulation Example 5 [00230] 35 parts of a mixture of ammonium salt of polyoxyethylenealkyl ether sulfate and white carbon (weight ratio 1: 1), 10 parts of any of the Compounds of the Present Invention 1 to 60 and 55 parts of water are mixed and, finally, sprayed by the wet grinding method to produce each flowable powder.
Formulation Example 6 [00231] 0.1 part of any of the Compounds of the Present Invention 1 to 60 is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and the mixture is mixed with 89.9 parts deodorized kerosene to produce each oily solution.
Formulation Example 7 [00232] 10 mg of any of the Compounds of the Present Invention 1 to 60 are dissolved in 0.5 ml of acetone, and this solution is applied to 5 g of the solid animal feed powder (powder of solid reason for creation CE-2, product of CLEA Japan, Inc.), and the mixture is uniformly mixed. Thereafter, the acetone is evaporated to dryness to produce each poisonous bait.
Formulation Example 8 [00233] 0.1 part of any of the Compounds of the Present Invention 1 to 60 and 49.9 parts of Neothiozol (Chuo Kasei Co., Ltd.) are filled in an aerosol can, and one The aerosol valve is attached, then the container is filled with 25 parts of di-methyl ether and 25 parts of LPG and is agitated, and a trigger is attached to produce oil-based aerosols.
Formulation Example 9 [00234] 0.6 part of any of the Compounds of the Present Invention 1 to 60, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of emulsifier {RHEODOL MO-60 (manufactured with Kao Corporation)} are mixed and dissolved, and the resulting solution and 50 parts of distilled water are filled in an aerosol container. A valve is attached to the container, then 40 parts of a propellant (LPG) are filled under pressure through the valve to produce an aqueous aerosol.
Formulation Example 10 [00235] 0.1 g of any of the compounds of the present invention 1 to 60 is dissolved in 2 ml of propylene glycol, and a 4.0 cm x 4.0 cm porous ceramic plate and 1 , 2 cm thick is impregnated with the solution to produce an agent that produces heating type smoke.
Formulation Example 11 [00236] 5 parts of any of the Compounds of the Present Invention 1 to 60 and 95 parts of an ethylene-methyl methacrylate copolymer (a ratio of methyl methacrylate to the copolymer: 10% by weight, Acryft WD301, produced by SUMITOMO CHEMICAL CO., Ltd.) are melted and kneaded with a closed pressurizer kneader (manufactured by Moriyama Works), resulting in kneaded material which is extruded from a molding machine through a molding mold to produce a mold rod shaped body with a size of 15 cm in length and 3 mm in diameter.
Formulation Example 12 [00237] 5 parts of any of the Compounds of the Present Invention 1 to 60 and 95 parts of a soft vinyl chloride resin are melted and kneaded with a closed pressurizing kneader (manufactured by Moriyama Works), and the resulting kneaded material is extruded from a molding machine through a molding mold to produce a rod shaped body 15 cm long and 3 mm in diameter.
Formulation Example 13 [00238] 100 mg of any of the Compounds of the Present Invention 1 to 60, 68.75 mg of lactose, 237.5 mg of corn starch, 43.75 mg of microcrystalline cellulose, 18.75 mg of polyvinylpyrrolidone, 28.75 mg of sodium carboxymethyl starch and 2.5 mg of magnesium stearate are mixed, and the resulting mixture was compressed to a suitable size to produce a tablet.
Formulation Example 14 [00239] 25 mg of any of the compounds of the present invention 1 to 60, 60 mg of lactose, 25 mg of corn starch, 6 mg of calcium carmelose and an adequate amount of hydroxypropylmethylcellulose. 5% pulp are mixed, and the resulting mixture is filled into a hard gelatin capsule or a hydroxypropyl methylcellulose capsule to produce an encapsulated formulation.
Formulation Example 15 [00240] Distilled water is added to 1000 mg of any of the Compounds of the Present Invention 1 to 60, 500 mg of fumaric acid, 2000 mg of sodium chloride, 150 mg of methylparaben, 50 mg of propylparaben , 25000 mg of granulated sugar, 13000 mg of sorbitol (70% solution), 100 mg of Veegum K (Vanderbilt Co.), 35 mg of flavoring and 500 mg of dye, so that a final volume is equal to 100 ml, and the mixture is mixed to produce a suspension for oral administration.
Formulation Example 16 [00241] 5% by weight of any of the Compounds of the Present Invention 1 to 60 is dissolved in 5% by weight of polysorbate 85, 3% by weight of benzyl alcohol and 30% by weight of propylene glycol, and one phosphate buffer is added to this solution, so that it has a pH of 6.0 to 6.5 and then water is added until it reaches the final volume to produce a liquid formulation for oral administration.
Formulation Example 17 [00243] 5% by weight of aluminum distearate is dispersed in 57% by weight of fractionated palm oil and 3% by weight of polysorbate 85 by heating. This dispersion is cooled to room temperature, and 25% by weight of saccharin is dispersed in an oily vehicle. 10% by weight of any of the Compounds of the Invention 1 to 60 is distributed in the dispersion to produce a paste formulation for oral administration.
Formulation Example 18 [00244] Any of the Compounds of the Present Invention 1 to 60 in an amount of 5% by weight and 95% by weight of limestone filler are mixed, and a granule for oral administration is produced using the granulation method wet.
Formulation Example 19 [00245] Any of the Compounds of the Present Invention 1 to 60 in an amount of 5 parts is dissolved in 80 parts of diethyleneglycolmonoethyl ether and 15 parts of propylene carbonate are mixed with it to produce a solution of local application.
Formulation Example 20 [00246] 10 parts of any of the Compounds of the Present Invention 1 to 60 are dissolved in 70 parts of diethylene glycolmoethyl ether, and 20 parts of 2-octyldodecanol are mixed with it to produce a solution to pour .
Formulation Example 21 [00247] NIKKOL TEALS-42 (Nikko Chemicals Co., Ltd., 42% aqueous solution of triethanolamine lauryl sulfate) in an amount of 60 parts and 20 parts of propylene glycol are added to 0.5 part of any one of the Compounds of the Present Invention 1 to 60, and the mixture is sufficiently stirred and mixed until it becomes a uniform solution, then 19.5 parts of water are added and, more sufficiently stirred and mixed to produce a shampoo agent such as a uniform solution.
Formulation Example 22 [00248] Any of the Compounds of the Present Invention 1 to 60 in an amount of 0.15% by weight, 95% by weight of animal feed and 4.85% by weight of a secondary calcium phosphate mixture , diatomaceous earth, Aerosil and carbonate (or limestone) are sufficiently agitated and mixed to produce a premix of feed for animal consumption.
Formulation Example 23 [00249] 7.2 g of any of the compounds of the present invention 1 to 60 and 92.8 g of VOSCO S-55 (manufactured with Maruishi Pharmaceutical Co., Ltd.) are dissolved and mixed at 100 ° C, poured into a suppository mold and cooled and solidified to produce a suppository.
Test Example 1 [00250] Formulations of the Compounds of the Present Invention 1 to 17, 19 to 27, 30 to 34, 36 to 39, 41 to 46, 48 to 49, 51, 54 and 57, as produced in the Formulation Example 5, were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00251] On the other hand, a cucumber seedling (the first true leaf stage) planted in a plastic cup was inoculated with about 30 Aphis gossypii (complete stage) and left to rest for one day. The test drug solution was sprayed in an amount of 20 mL in the seedling.
[00252] Six days after spraying, the number of parasitic survivors of Aphis gossypii on the cucumber leaves was examined, and the control value was calculated according to the following equation: Control value (%) = {1 - (Cb χ Tai) / (Cai χ Tb)} χ 100 where the symbols represent: Cb: the number of insects in an untreated section before treatment Cai: the number of parasitic insects surviving in an untreated section under observation Tb: o number of insects in a treated section before Tai treatment: the number of parasitic insects surviving in a treated section under observation where the untreated section refers to a section where the test pesticide solution prepared by diluting the formulation produced as in Formulation Example 5, but without containing the compound of the present invention with the same amount of water as in the treated section, was sprayed.
[00253] As a result, in the treated section where the test pesticide solution containing each of the Compounds of the present invention was used 1 to 17, 19 to 27, 30 to 34, 36 to 39, 41 to 46, 48 to 49, 51, 54 and 57, with the control value equal to 90% or more.
Test Example 2 [00254] Formulations of the Compounds of the Present Invention 2, 4 to 5, 8 to 9, 13, 15 to 16, 19, 22 to 23, 30 to 33 and 41, as produced in Formulation Example 5, were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00255] On the other hand, a cucumber seedling (in the second true leaf stage) planted in a plastic cup was soaked on your foot with 5 mL of test pesticide solution, and was kept in a greenhouse at 25 ° C for 7 days . About 30 Aphis gossypii (full-stage) were inoculated on the surface of the cucumber leaf and were additionally kept in the greenhouse for 6 days, and then the number of Aphis gossypii parasitic survivors on the cucumber leaves was examined, and the value The control value was calculated according to the following equation: Control value (%) = {1 - (Cb χ Tai) / (Cai χ Tb)} χ 100 in which the symbols represent: Cb: the number of insects in a section untreated before treatment Cai: the number of parasitic insects surviving in an untreated section under observation Tb: the number of insects in a treated section prior to treatment Tai: the number of parasitic insects surviving in a treated section under observation where untreated section refers to a section where the test pesticide solution prepared by diluting the formulation produced as in Formulation Example 5, but without containing the compound of the present invention to the same amount water as in the treated section, was sprayed.
[00256] As a result, in the treated section where the test pesticide solution containing each of the Compounds of the Present Invention 2, 4 to 5, 8 to 9, 13, 15 to 16, 19, 22 to 23, 30 to 33 and 41 was used, the control value was equal to 90% or more.
Test Example 3 [00257] Formulations of the Compounds of the Present Invention 3, 15 to 16, 19, 22 to 23, 30 to 34, 36 to 39, 41 to 46, 48, 51 and 54, as produced in the Formulation Example 5, were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00258] In a rice seedling in the second leaf stage planted in a polyethylene cup, 10 mL of each test pesticide solution was sprayed. After air drying, 20 three quarters of instar of Nilaparvata lugens larvae were released and kept in an oven at 25 ° C. After 6 days, the number of surviving Nilaparvata lugens parasites in rice was examined, and the control value was calculated according to the following equation: Control value (%) = {1 - (Cb χ Tai) / (Cai χ Tb )} χ 100 where the symbols represent: Cb: the number of insects in an untreated section before treatment Cai: the number of parasitic insects surviving in an untreated section under observation Tb: the number of insects in a section treated before of the Tai treatment: the number of parasitic insects surviving in a treated section under observation where the untreated section refers to a section where the test pesticide solution prepared by diluting the formulation produced as in Formulation Example 5, but without containing the compound of the present invention with the same amount of water as in the treated section, was sprayed.
[00259] As a result, in the treated section where the test pesticide solution containing each of the Compounds of the Present Invention 3, 15 to 16, 19, 22 to 23, 30 to 34, 36 to 39, 41 to 46, 48, 51 and 54 was used, the control value was equal to 90% or greater.
Test Example 4 [00260] Formulations of the Compounds of the Present Invention 3, 5 to 6, 8, 11, 15 to 16, 19 to 20, 22 to 23, 30 to 34, 39, 41 to 43 and 45, as produced in Formulation Example 5, they were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00261] On the other hand, a rice seedling (2 weeks after sowing in the second leaf stage) planted in a plastic cup was soaked on your foot with 5 mL of each test pesticide solution, and was kept in a greenhouse at 25 ° C for 7 days. Twenty-three larvae in the fourth instar of Nilaparvata lugens were released, and additionally kept in the greenhouse for 6 days, then the number of surviving Nilaparvata lugens parasites on the rice leaves was analyzed, and the control value was calculated according to the following equation: Control value (%) = {1 - (Cb χ Tai) / (Cai χ Tb)} χ 100 where the symbols represent: Cb: the number of insects in an untreated section before treatment Cai : the number of parasitic insects surviving in an untreated section under observation Tb: the number of insects in a treated section before treatment Tai: the number of parasitic insects surviving in a treated section under observation where the untreated section refers to a section where the test pesticide solution prepared by diluting the formulation produced, as in Formulation Examples 3, 5 to 6, 8, 11, 15 to 16, 19 to 20, 22 to 23, 30 to 34, 39, 41 to 43 and 45, but without containing the make up this invention with the same amount of water as in the treated section, was sprayed.
[00262] As a result, in the treated section where the test pesticide solution containing the Compound of the Present Invention 5 was used, the control value was equal to 90% or greater.
Test Example 5 [00263] The formulation of the compound of the present invention, as produced in Formulation Example 5, was diluted with water in order to have an active ingredient concentration equal to 500 ppm, to prepare a test pesticide solution.
[00264] On the other hand, adult Bemisia tabaci is released in a tomato seedling (the third true leaf stage) planted in a polyethylene cup and made so that the eggs are laid for about 72 hours. The tomato seedling is kept in a greenhouse for 8 days and, when the instar larvae hatch from the eggs, the above test pesticide solution is sprayed at a rate of 20 mL / cup, and the cup is kept in a greenhouse at 25 ° C . After 7 days, the number of instar larvae surviving on tomato leaves is examined, and the control value is calculated according to the following equation: Control value (%) = {1 - (Cb χ Tai) / (Cai χ Tb)} χ 100 where the symbols represent: Cb: the number of instar larvae in an untreated section before treatment Cai: the number of instar larvae surviving in an untreated section under observation Tb: the number of instar larvae in a treated section before Tai treatment: the number of instar larvae surviving in a treated section under observation where the untreated section refers to a section where the test pesticide solution prepared by diluting the formulation obtained as in Formulation Example 5, but without containing the compound of the present invention with the same amount of water as in the treated section, it was sprayed.
[00265] As a result, in the treated section where the test pesticide solution of the compound of the present invention is used, an excellent control value is produced.
Test Example 6 [00266] Formulations of the Compounds of the Present Invention 1, 6 to 9, 11, 14 to 16, 19, 22 to 24, 30 to 32, 34 to 39, 41 to 43 and 45 to 46, as produced in Formulation Example 5, they were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00267] On the other hand, the cabbage in the third leaf stage planted in a polyethylene cup was sprayed, at a rate of 20 mL / cup, the test pesticide solution. After the pesticide solution dried, the foliage part was cut and then placed in a 50 mL volume beaker. Five larvae in the second instar of Plutella xylostella were placed in the cup, and the cup was sealed with a lid. After the cup was kept at 25 ° C for 5 days, the number of dead insects was counted. The mortality rate was calculated according to the following equation: Mortality rate (%) = (number of dead insects / number of insects tested) χ 100 [00268] As a result, in the treated section where the test pesticide solution containing each of the Compounds of the Present Invention 1, 6 to 9, 11, 14 to 16, 19, 22 to 24, 30 to 32, 34 to 39, 41 to 43 and 45 to 46 was used, the mortality rate was equal to or greater than 80%.
Test Example 7 [00269] The formulations of the Compounds of the Present Invention 1, 3, 7 to 9, 11, 15 to 17, 19 to 22, 24 to 26 and 30 to 31 produced in Formulation Example 5, were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare a test spray solution.
[00270] On the other hand, an apple tree was planted in a plastic cup and cultivated until the real seventh-eighth leaf appears. The test pesticide solution was sprayed on the apple tree at a rate of 20 mL / glass. After the pesticide solution was dried, 60 larvae on the first instar of Adoxophyes orana fasciata were released, and covered with a plastic cup, the bottom of which was cut and on which a filter paper was placed, with the lid of the plastic cup being placed upside down. After 7 days, the number of dead insects was counted, and the mortality rate was calculated according to the following equation: Mortality rate (%) = (number of dead insects / number of insects tested) χ 100 [00271 As a result, in the treated section where the test pesticide solution containing each of the Compounds of the Present Invention 1, 3, 7 to 9, 11, 15 to 17, 19 to 22, 24 to 26 and 30 to 31 was used, the rate mortality was 90% or more.
Test Example 8 [00272] The formulations of the Compounds of the Present Invention 1,9, 15 to 16, 19, 22, 24, 31 to 32, 34, 41 and 45 to 46, as produced in the Example of Formulation 5, were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00273] A 5.5 cm diameter filter paper was spread on the bottom of a polyethylene cup of the same diameter and 0.7 mL of the test pesticide solution was added dropwise over the filter paper, and 30 mg of sucrose were placed evenly as bait. In the polyethylene cup, 10 female images of Musca domestica were released, and the cup was sealed with a lid. After 24 hours, live and dead Musca domestica were examined, the number of dead insects was counted and the mortality rate was calculated according to the following equation.
Mortality rate (%) = (number of dead insects / number of insects tested) χ 100 [00274] As a result, in the treated section where the test pesticide solution containing each of the Compounds of the present invention 1,9, 15 to 16, 19, 22, 24, 31 to 32, 34, 41 and 45 to 46 were used, the mortality rate was equal to 100%.
Test Example 9 [00275] The formulations of the Compounds of the Present Invention 9, 15 to 16, 19, 22, 30 to 32, 34, 41 and 45 to 46, as produced in the Example of Formulation 5, were diluted with water, in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00276] A 5.5 cm diameter filter paper was spread on the bottom of a polyethylene cup of the same diameter and 0.7 ml of the test pesticide solution was added dropwise over the filter paper, and 30 mg of sucrose were placed evenly as bait. In the polyethylene cup, 2 male images of Blattella germanica were released, and the cup was sealed with a lid. After 6 days, the live and dead Blattella germanica were examined, the number of dead insects was counted and the mortality rate was calculated according to the following equation.
Mortality rate (%) = (number of dead insects / number of insects tested) χ 100 [00277] As a result, in the treated section where the test pesticide solution containing each of the Compounds of the Present Invention 9, 15 to 16, 19, 22, 30 to 32, 34, 41 and 45 to 46 were used, the mortality rate was equal to 100%.
Test Example 10 [00278] The formulations of the Compounds of the Present Invention 1, 4, 6 to 12, 14 to 16, 19, 22 to 24, 30 to 32, 34, 36 to 39, 41 to 43 and 45 to 46, as produced in Formulation Example 5, were diluted with water in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00279] 0.7 mL of the test pesticide solution was added to 100 mL of ion exchange water (active ingredient concentration: 3.5 ppm). Twenty larvae in the last instar stage of Culex pipiens pallens were released into the solution. A day later, the living and dead Culex pipiens pallens were examined, and the number of dead insects was counted to calculate the mortality rate.
Mortality rate (%) = (number of dead insects / number of insects tested) χ 100 [00280] As a result, in the treated section where the test pesticide solution containing each of the Compounds of the present invention 1, 4, 6 a 12, 14 to 16, 19, 22 to 24, 30 to 32, 34, 36 to 39, 41 to 43 and 45 to 46 were used, the mortality rate was equal to or greater than 95%.
Test Example 11 [00281] Two milligrams of each of the compounds of the present invention 8 to 9, 20, 22 and 31 to 32 were weighed in a screw cap tube (Maruemu No. 5; 27 x 55 mm) and 0 , 2 ml of acetone was added thereto, and the screw cap tube was sealed with a cap to dissolve the compound. The screw cap tube was rotated and inverted to uniformly coat the pesticide solution across the inner wall of the tube. After removing the cap, the solution was air-dried for about 2 hours and then the nests of non-fed ducks, Haemaphysalis longicornis (5 ducks / group) were released, and the tube was sealed with cap. After 2 days, the number of dead insects was counted, and the mortality rate was calculated according to the following equation: Mortality rate (%) = 100 x (number of dead insects / number of insects tested) [00282 As a result, in the treated section where the test pesticide solution containing each of the Compounds of the Present Invention 8 to 9, 20, 22 and 31 to 32 was used, the mortality rate was equal to 100%. Test Example 12 [00283] Formulations of the Compounds of the Present Invention 3, 7, 28, 32 to 34, 36 to 46, 48 to 49, 51 to 54, as produced in Formulation Example 1, were diluted with water, in order to have an active ingredient concentration of 500 ppm to prepare each test pesticide solution.
[00284] On the other hand, in the third leaf stage cucumber planted in a polyethylene cup, the test pesticide solution was sprayed at a rate of 30 mL / cup. After the pesticide solution was dried, the second leaf was cut and then placed in a 200 ml beaker. Ten larvae in the second instar of Plutella xylostella were placed in the cup, and the cup was sealed with a lid. After the cup was kept at 25 ° C for 5 days, the number of dead insects was counted. The mortality rate was calculated according to the following equation: Mortality rate (%) = (number of dead insects / number of insects tested) χ 100 [00285] As a result, in the treated section where the test pesticide solution containing each one of the Compounds of the Present Invention 3, 7, 28, 32 to 34, 36 to 46, 48 to 49, 51 and 54 was used, the control value was equal to 80% or greater.
Test Example 13 [00286] The formulation of the compound of the present invention, as produced in Formulation Example 1, was diluted with water in order to have an active ingredient concentration equal to 500 ppm, to prepare a test pesticide solution.
[00287] On the other hand, the artificial feed for Diabrotica virgi-fera virgifera is prepared according to the procedures of Pleau, et al. (Entomologia Experimentalis et Applicata 105: 1-11, 2002), and 2 of the feed are placed in each well of a 24-well microplate (manufactured with Becton Dickinson). The test pesticide solution described above is sprayed on the artificial feed at a rate of 40 mL / well and, after the pesticide solution is dried, five Diabrotica virgifera vir-gifera in the first instar were released by 1 well, and the well is sealed and covered with parafilm (manufactured by Bemis Company, Inc.). The cup is kept at 25 ° C and, after 3 days of treatment, the number of dead insects is in contact. The mortality rate was calculated according to the following equation: Mortality rate (%) = (number of dead insects / number of insects tested) χ 100 [00288] As a result, in the treated section where the compound of the present invention is used, a control effect is noticed. INDUSTRIAL APPLICABILITY
[00289] The compound of the present invention has a pest control effect and is useful as an active ingredient in a pest control agent.

权利要求:
Claims (12)
[1]
1. Fused heterocyclic compound, characterized by the fact that it is represented by formula (1): where A1 represents NR5, an oxygen atom or a sulfur atom, A2 represents a nitrogen atom or CR6, A3 represents a nitrogen atom or CR7, R1 represents a chain hydrocarbon group C1 to C6, optionally with one or more atoms or groups selected from the group U or an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, R2 hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U, a phenyl group optionally with one or more atoms or groups selected from the group W, a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the group W, OR8, S (O) mR8, S (O) 2NR8R9, NR8R9, NR8CÜ2R9, NR8C (O) R9, CO2R8, C (O) R8, C (O) NR8R9, SF5, a cyan group , a nitro group, a halogen atom or an atom the hydrogen one, G represents a group represented by the group G5 of the following formula: where R19 represents a hydrocarbon group from the Ci to C6 chain optionally with one or more atoms or groups selected from the Y group, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from group W, a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from group W, or one hydrogen atom, R20 represents R52, where R52 represents a hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from the group W, a 4, 5 or 6 membered heterocyclic group optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, OR53, where R53 represents a hydrocarbon group from the C1 to C6 chain optionally with one or more atoms or groups selected from the Y group, an alicyclic hydrocarbon group from C3 to C9 optionally with one or more atoms or groups selected from the group V, a phenyl group optionally with one or more atoms or groups selected from the group W or a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W , or NR54R55, where R54 and R55 are the same or different and represent a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the Y group, a C3 to C9 alicyclic hydrocarbon group optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or groups selected from group W, a heterocyclic group of 4, 5 or 6 members optionally with one or more atoms or groups selected from the group W, or a hydrogen atom, R3 and R4 are the same or different and represent a chain hydrocarbon group C1 to C6 optionally with one or more atoms or groups selected from the group U, a phenyl group optionally with one or more atoms or groups selected from the W group, a 5- or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the W group, OR8, S (O) mR8, S (O) 2NR8R9, NR8R9, NR8CO2R9, NR8C (O) R9, CO2R8, C (O) R8, C (O) NR8R9, SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom, or R3 and R4, together with carbon atoms to which they are attached, form a benzene ring, optionally with one or more atoms or groups selected from the group W, a 5- or 6-membered heterocyclic ring, optionally with one or more atoms or groups selected from the group W or a ring non-aromatic 5, 6, 7 or 8 members optionally with one or more atoms or groups selected group V, R5 represents a C1 to C6 chain hydrocarbon group, optionally with one or more atoms or groups selected from the X group, a C1 to C6 chain hydrocarbon group with a phenyl group, where the phenyl group optionally has , one or more atoms or groups selected from the W group, a C1 to C6 chain hydrocarbon group with a 5- or 6-membered heterocyclic group, where the 5- or 6-membered heterocyclic group optionally has one or more atoms or groups selected group W, CO2R8, C (O) R8, an alicyclic hydroarbonide group from C3 to C9 optionally with one or more atoms or groups selected from group V, or a hydrogen atom, R6 and R7 are the same or different and represent a group hydrocarbon chain C1 to C6 optionally with one or more halogen atoms, OR8, S (O) mR8, NR8R9, CO2R8, C (O) R8, a cyano group, a nitro group, a halogen atom or a hydrogen atom , R8 and R9 are the same or different and represent a group hydrocarbon chain C1 to C6 optionally with one or more atoms or groups selected from group Y, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, a phenyl group optionally with one or more atoms or selected groups from the W group, a 4-, 5 or 6-membered heterocyclic group optionally with one or more atoms or groups selected from the W group, or a hydrogen atom, and each m independently represents 0, 1 or 2, and n represents 0, 1 or 2, where m is 1 or 2 in S (O) mR8, R8 does not represent a hydrogen atom; Group U: a group consisting of C1 to C6 alkoxy groups, optionally with one or more halogen atoms, C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more atoms halogen groups, C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfinyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally with one or more halogen atoms, C2 alkylcarbonyl groups to C6 optionally with one or more halogen atoms, alkoxycarbonyl group C2 to C6 optionally with one or more halogen atoms, cycloalkyl groups C3 to C9 optionally with one or more halogen atoms or one or more alkyl groups Ci to C3, cyano groups, hydroxy groups and halogen atoms, Group V: a group consisting of C1 to C6 chain hydrocarbon groups, optionally with one or more halogen atoms, alkoxy groups C1 to C6 optionally with one or more halogen atoms, C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more halogen atoms, and halogen atoms, Group W: a group consisting of C1 to C6 chain hydrocarbon groups optionally with one or more halogen atoms, C1 to C6 alkoxy groups optionally with one or more halogen atoms, C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms, groups alkylsulfinyl C1 to C6 optionally with one or more halogen atoms, alkylsulfonyl groups C1 to C6 optionally with one or more halogen atoms, alkyl-mino groups C1 to C6 optionally with one or more halogen atoms, dialkylamino groups C2 to Cs optionally with one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally with one or more halogen atoms, C2 to C6 alkoxycarbonyl groups optionally with one or more halogen atoms, halogen groups, cyano groups and nitro groups, Group X: a group consisting of C3 to C9 cycloalkyl groups, optionally with one or more halogen atoms, C1 to C6 alkoxy groups optionally with one or more halogen atoms , C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more halogen atoms, C1 to C6 alkylsulfanyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfinyl groups optionally with one or more halogen atoms, C1 to C6 alkylsulfonyl groups optionally with one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally with one or more halogen atoms, C2 to C6 alkoxycarbonyl group optionally with one or more halogen atoms , hydroxy groups, halogen atoms and cyano groups, Group Y: a group consisting of C3 to C9 alicyclic hydrocarbon groups optionally with one or more atoms or groups selected from group V, C1 to C6 alkoxy groups optionally with one or more halogen atoms, C2 to C6 alkenyloxy groups optionally with one or more halogen atoms, C2 to C6 alkynyloxy groups optionally with one or more halogen atoms, alkylsulfanyl groups C1 to C6 optionally with one or more halogen atoms, C1 to C6, alkylsulfinyl groups C1 to C6 optionally with one or more halogen atoms, alkylsulfonyl groups C1 to C6 optionally with one or more halogen atoms, alkylaminosulfonyl groups C1 to C6 optionally with one or more halogen atoms, di-alkylaminosulfonyl groups C2 to Cs optionally with one or more halogen atoms, alkylamino groups C1 to C6 optionally, with one or more halogen atoms, dialkylamino groups C2 to Cs optionally with one or more halogen atoms, C2 to C6 alkylcarbonylamino groups optionally with one or more halogen atoms, C2 to C alkoxycarbonylamino groups 6 optionally with one or more halogen atoms, C2 to C6 alkylcarbonyl groups optionally with one or more halogen atoms, C2 to C6 alkoxycarbonyl groups optionally having one or more halogen atoms, C2 to C6 alkylamino carbonyl groups optionally with one or more halogen atoms, dialkylaminocarbonyl groups C3 to C10 optionally with one or more halogen atoms, cyano groups, hydroxy groups and halogen atoms, or an N-oxide thereof.
[2]
2. A compound according to claim 1, characterized by the fact that R1 is a C1 to C6 alkyl group, optionally with one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups, in which the cyclopropyl group optionally has one or more halogen atoms or one or more C1 to C3 alkyl groups, a C2 to C6 alkenyl group optionally with one or more halogen atoms, an C2 to C6 alkynyl group optionally with one or more atoms halogen, or a C3 to C6 cycloalkyl group optionally with one or more atoms or groups selected from the group consisting of halogen atoms and C1 to C6 alkyl groups, optionally with one or more halogen atoms, R2 is an atom of halogen or a hydrogen atom, R3 and R4 are the same or different and are a C1 to C6 chain hydrocarbon group optionally with one or more atoms or groups selected from the group U, OR8, S (O) mR8, a halogen atom nio or a hydrogen atom, and R5 is a C1 to C6 chain hydrocarbon group, optionally with one or more atoms or groups selected from the group X, CO2R8, C (O) R8, an alicyclic hydrocarbon group C3 to C9 optionally with one or more atoms or groups selected from group V, or a hydrogen atom.
[3]
3. A compound according to claim 1 or claim 2, characterized by the fact that A1 is NR5.
[4]
4. A compound according to claim 1 or claim 2, characterized by the fact that A1 is an oxygen atom.
[5]
Compound according to claim 1 or claim 2, characterized in that A1 is a sulfur atom.
[6]
A compound according to any one of claims 1 to 5, characterized in that A2 is CR6 and A3 is a nitrogen atom.
[7]
Compound according to any one of claims 1 to 5, characterized in that A2 is CR6 and A3 is CR7.
[8]
8. Compound, characterized by the fact that it is represented by formula (1A), in which the symbols represent the same meaning as in formula (1).
[9]
9. Compound, characterized by the fact that it is represented by formula (1B), in which the symbols represent the same meaning as in formula (1).
[10]
10. Compound, characterized by the fact that it is represented by the formula (1C), in which the symbols represent the same meaning as in the formula (1).
[11]
11. Pest control agent, characterized in that it comprises the compound as defined in any one of claims 1 to 10, and an inert vehicle.
[12]
12. Method for controlling pests, characterized in that it comprises applying an effective amount of the compound, as defined in any one of claims 1 to 10, to a pest or pest infested area, wherein the therapeutic use of the compound as defined in any of claims 1 to 10 is excluded.

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引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

WO2002002540A1|2000-07-04|2002-01-10|Ube Industries, Ltd.|Benzoxazole compound, process for producing the same, and herbicide|

---

AR037228A1|2001-07-30|2004-11-03|Dow Agrosciences Llc|ACID COMPOUNDS 6- -4-AMYNOPYCOLINIC, HERBICIDE COMPOSITION THAT UNDERSTANDS AND METHOD TO CONTROL UNWANTED VEGETATION|

---

JP5369854B2|2008-04-21|2013-12-18|住友化学株式会社|Harmful arthropod control composition and condensed heterocyclic compound|

---

BRPI1015315B1|2009-04-28|2020-02-04|Sumitomo Chemical Co|fused heterocyclic compound, its use, composition and method of controlling a harmful arthropod|

---

TW201234965A|2010-12-24|2012-09-01|Sumitomo Chemical Co|Fused heterocyclic compound and use for pest control thereof|

---

TWI589570B|2011-08-04|2017-07-01|住友化學股份有限公司|Fused heterocyclic compound and use thereof for pest control|

---

TWI614242B|2013-01-31|2018-02-11|住友化學股份有限公司|Composition and method for controlling pests|

---

TWI607005B|2013-01-31|2017-12-01|住友化學股份有限公司|Composition and method for controlling pests|

---

EP2952098B1|2013-01-31|2017-12-20|Sumitomo Chemical Company, Limited|Pest-control method|

---

TWI621616B|2013-01-31|2018-04-21|住友化學股份有限公司|Composition and method for controlling pests|

---

JP6191626B2|2013-01-31|2017-09-06|住友化学株式会社|Pest control composition and pest control method|

---

JP6350528B2|2013-07-01|2018-07-04|住友化学株式会社|Fused heterocyclic compounds and their use for pest control|JP6350528B2|2013-07-01|2018-07-04|住友化学株式会社|Fused heterocyclic compounds and their use for pest control|

---

WO2015198859A1|2014-06-26|2015-12-30|住友化学株式会社|Condensed heterocyclic compound|

---

UY36547A|2015-02-05|2016-06-01|Bayer Cropscience Ag|BICYCLIC CONDENSED HETEROCYCLIC DERIVATIVES REPLACED BY 2-ARILO AS PESTICIDES|

---

MX2017010420A|2015-02-12|2017-11-28|Nissan Chemical Ind Ltd|Condensed heterocyclic compound and noxious organism control agent.|

---

AR105607A1|2015-08-07|2017-10-18|Bayer Cropscience Ag|HETEROCYCLIC CONDENSED DERIVATIVES REPLACED BY 2-ARILO AS PESTICIDES|

---

AU2016330299B2|2015-09-28|2020-04-30|Bayer Cropscience Aktiengesellschaft|2-Aryl-substituted condensed bicyclic heterocyclic derivatives as pest control agents|

---

EP3372595A4|2015-10-13|2019-04-24|Nihon Nohyaku Co., Ltd.|Oxime group-containing condensed heterocyclic compound or salts thereof and agricultural and horticultural insecticide containing said compound, and method for using same|

---

US10550116B2|2015-10-26|2020-02-04|Bayer Cropscience Aktiengesellschaft|Fused bicyclic heterocycle derivatives as pesticides|

---

KR20180088416A|2015-11-30|2018-08-03|혹꼬우 가가꾸 고오교오 가부시끼가이샤|1,2,3-triazole derivatives and insecticidal / acaricidal agents containing the derivatives as an active ingredient|

---

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---

BR112018014512A2|2016-02-26|2018-12-11|Nihon Nohyaku Co., Ltd.|benzoxazole compound, agricultural and horticultural insecticide, method to use it and animal ectoparasite control agent|

---

EP3428166A4|2016-03-10|2019-11-13|Nissan Chemical Corporation|Condensed heterocyclic compound and pest control agent|

---

KR101842344B1|2016-04-19|2018-03-26|경북대학교 산학협력단|Novel compound, fabrication method of the novel compound, and colorfilter for liquid crystal display including the novel compound|

---

EP3241830A1|2016-05-04|2017-11-08|Bayer CropScience Aktiengesellschaft|Condensed bicyclic heterocyclic derivatives as pesticides|

---

MX2019000793A|2016-07-19|2019-06-20|Bayer Cropscience Ag|Condensed bicyclic heterocycle derivatives as pest control agents.|

---

CN109996799A|2016-08-15|2019-07-09|拜耳作物科学股份公司|Fused bicyclic heterocycle derivative as pest control agent|

---

KR20190038890A|2016-08-16|2019-04-09|바이엘 크롭사이언스 악티엔게젤샤프트| -3H-imidazole [4,5-c] pyridine derivative by reaction of 3H-imidazo [4,5-c] pyridine derivative with an organometallic zinc- ] Pyridine derivatives and related compounds|

---

CN109415357B|2016-09-01|2021-10-29|日本农药株式会社|Condensed heterocyclic compound having hydrazone group or salt thereof, agricultural and horticultural insecticide containing the compound, and method for using the same|

---

MX2019004032A|2016-10-06|2019-07-04|Bayer Cropscience Ag|2-aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents.|

---

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---

US10961248B2|2016-12-01|2021-03-30|Syngenta Participations Ag|Pesticidally active heterocyclic derivatives with sulfur containing substituents|

---

WO2018105632A1|2016-12-07|2018-06-14|日本農薬株式会社|Quinoline compound having carbamate group, salt of same, insecticide for agricultural and horticultural use containing said compound, and use of said insecticide|

---

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---

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---

BR112019015139A2|2017-01-24|2020-03-24|Sumitomo Chemical Company, Limited|Fused HETEROCYCLIC COMPOUND AND COMPOSITION CONTAINING THE SAME|

---

TW201829408A|2017-02-06|2018-08-16|德商拜耳作物科學股份有限公司|Method for preparing halogenated imidazopyridine derivatives|

---

TW201833107A|2017-02-06|2018-09-16|德商拜耳廠股份有限公司|2-aryl-substituted fused heterocycle derivatives as pesticides|

---

EP3604300A4|2017-03-23|2020-12-16|Sumitomo Chemical Company, Limited|Fused heterocyclic compound and composition containing same|

---

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---

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---

JP2020172439A|2017-07-07|2020-10-22|日本農薬株式会社|Method for Producing Condensed Heterocyclic Compound|

---

US11203590B2|2017-07-13|2021-12-21|Sumitomo Chemical Company, Limited|Heterocyclic compound and harmful-arthropod control agent containing same|

---

WO2019076778A1|2017-10-16|2019-04-25|Syngenta Participations Ag|Pesticidally active heterocyclic derivatives with sulfur and sulfonimidamides containing substituents|

---

CN111770923A|2017-12-26|2020-10-13|住友化学株式会社|Heterocyclic compound and noxious arthropod control agent containing same|

---

US20210047291A1|2018-01-15|2021-02-18|Syngenta Participations Ag|Pesticidally active heterocyclic derivatives with sulfur containing substituents|

---

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---

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---

WO2019229088A1|2018-05-30|2019-12-05|Syngenta Participations Ag|Pesticidally active heterocyclic derivatives with sulfur containing substituents|

---

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---

AR115495A1|2018-06-06|2021-01-27|Syngenta Crop Protection Ag|HETEROCYCLIC DERIVATIVES WITH SUBSTITUENTS CONTAINING ACTIVE SULFUR AS PESTICIDES|

---

TW202017920A|2018-08-20|2020-05-16|日商住友化學股份有限公司|Benzoxazole compound and use thereof|

---

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---

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---

WO2021009311A1|2019-07-17|2021-01-21|Syngenta Crop Protection Ag|Pesticidally active heterocyclic derivatives with sulfur containing substituents|

---

WO2021213978A1|2020-04-21|2021-10-28|Bayer Aktiengesellschaft|2-aryl-substituted condensed heterocyclic derivatives as pest control agents|

---

WO2022002818A1|2020-07-02|2022-01-06|Bayer Aktiengesellschaft|Heterocyclene derivatives as pest control agents|

法律状态:
2017-12-12| B07D| Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]|Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS. |

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2018-05-02| B07G| Grant request does not fulfill article 229-c lpi (prior consent of anvisa) [chapter 7.7 patent gazette]|

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2019-05-14| B06T| Formal requirements before examination [chapter 6.20 patent gazette]|

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2019-12-03| B15K| Others concerning applications: alteration of classification|Free format text: AS CLASSIFICACOES ANTERIORES ERAM: C07D 413/04 , A01N 43/76 , A01N 43/78 , A01N 43/90 , A01N 47/12 , A01N 47/18 , A01N 47/36 , A01P 7/02 , A01P 7/04 , A61K 31/4439 , A61K 31/444 , A61P 31/00 , A61P 33/00 , C07D 413/14 , C07D 471/04 , C07D 471/14 Ipc: C07D 413/04 (1974.07), A01N 43/76 (1980.01), A01N |

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2019-12-10| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2020-01-14| B09X| Decision of grant: republication|

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2020-03-10| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 25/06/2014, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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JP2013137783|2013-07-01|

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JP2013-137783|2013-07-01|

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PCT/JP2014/067603|WO2015002211A1|2013-07-01|2014-06-25|Fused heterocyclic compound and pest control use thereof|

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