SUBSTITUTED COMPOUNDS OF PYRIMIDINIUM, COMPOSITION, AGRICULTURAL COMPOSITION, METHOD FOR THE PROTECT

专利摘要:
substituted pyrimidinium compounds, composition, agricultural composition, method for crop protection, plants, plant propagation material, method for combating, controlling, preventing or protecting invertebrate pests, non-therapeutic method for treating animals and using of the compounds. the present invention relates to substituted pyrimidinium compounds of general formula (i) and their uses for combating animal pests. the present invention also relates to substituted pyrimidinium compounds of formula (i), their stereoisomers or their salts or tautomers or their n-oxides and compositions comprising these compounds. the present invention also relates to the methods and uses of these substituted pyrimidinium compounds and their compositions, for combating and controlling animal pests. moreover, the present invention also relates to methods of applying pesticides such substituted pyrimidinium compounds. the substituted pyrimidinium compounds of the present invention are defined by formula (i): wherein x, y, z, r 1, r 2, a and het are defined as described.
公开号:BR112015021863B1
申请号:R112015021863-6
申请日:2014-04-11
公开日:2020-08-18
发明作者:Joachim Dickhaut；Jean-Yves Wach；Nina Gertrud Bandur；Arun Narine；Swetlana Derksen；Raffael KOLLER；Wolfgang Von Deyn；Deborah L. Culbertson
申请人:Basf Se；
IPC主号:

专利说明:

FIELD OF THE INVENTION
[001] The present invention relates to substituted insecticidal pyrimidinium compounds and / or compositions comprising such AtAtcompounds for combating invertebrate pests. The present invention also relates to the pesticidal methods, uses and applications of the substituted pyrimidinium compounds, as described in the present invention, and their stereoisomers, salts, tautomers and N-oxides, as well as the compositions comprising them. BACKGROUND OF THE INVENTION
[002] Invertebrate pests and, in particular, insects, arthropods and nematodes destroy cultivation and harvesting and attack wooden housing and commercial structures, thereby causing great economic losses to food supply and property . Although a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is a continuing need for new agents to combat invertebrate pests such as insects, arachnids and nematodes. It is therefore an object of the present invention to provide compounds that have good pesticidal activity and that show a broad spectrum of activity against a large number of different invertebrate pests, especially against insects, arachnids and nematodes that are difficult to control. BRIEF DESCRIPTION OF THE INVENTION
[003] It has been discovered that these objects can be reached by substituted pyrimidinium compounds of general Formula (I), as defined below, including stereoisomers, salts, in particular, agriculturally and veterinarily acceptable salts, tautomers and N -oxides thereof.
[004] Accordingly, in a first aspect, the present invention provides the pyrimidinium compounds of Formula (I) or a composition comprising at least one substituted pyrimidinium compound of Formula (I)
- where - each X, Y, independently, is O or S; - Z is a direct link, O, S (O) m, NRb, C (RaRaa) O, C (= X1), C (= X1) Y1, or Y1C (= X1); - X1 is O, S, or NRb; - Y1 is O, S, or NRC; - A is CH or N and, where the nitrogen of the pyrimidinium ring taken together with the contiguous carbon atom and A, as represented in Formula (I), form a four to seven membered ring, where each remaining ring member is selected from the carbon atoms and up to 3 hetero atoms are independently selected from up to 2 O, up to 2 S, and up to 3 N (RC) P, where up to 2 ring members of the atoms of carbon are independently selected from C (= O) and C (= S), and the ring members of the sulfur atoms are independently selected from S (= O) m, where each ring can be replaced by up to three Ra; - Het is a three to ten membered heterocyclic ring or a seven to eleven membered heterocyclic ring system, each ring or ring member system is selected from carbon atoms and up to 4 hetero atoms are independently selected from up to 2 O, up to 2 S, and up to 4 N (RC) P, where up to 3 ring members of the carbon atoms are independently selected from C (= O) and C (= S) and the ring members of the sulfur atoms are independently selected from S (= O) o (= NRb) q, each ring or ring system optionally substituted by up to five Ra; - each o, q, independently, are 0, 1 or 2, as long as the sum (o + q) is 0, 1 or 2, in each ring; - R1 is hydrogen, C1-Cβ alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C10 cycloalkyl, C4-C10 cycloalkenyl, C5-C14 or R1 cycloalkylalkylalkyl or R1 can form a saturated carbo- or heterocyclic ring or ring system , or partially unsaturated or aromatic from three to eleven members, which may contain from 1 to 4 heteroatoms selected from N (RC) P, O, and S, where S can be oxidized, and in which the groups mentioned above and the carbo- or heterocyclic ring system can be unsubstituted, partially or completely replaced by Ra; or - R1 is C (= O) Rb, C (= O) ORe, NRbRc, C (= O) NRbRc, C (= S) NRbRc, SO2NRbRc, OC (= O) RC, OC (= O) ORe , OC (= O) NRbRe, N (Rc) C (= O) Rc, N (Rc) C (= O) ORe, N (Rc) C (= O) NRbRc, NRcSθ2Rb, NRcSθ2NRbRc, Si (Rd) 3 , C (= NRC) RC, C (= NORC) RC, C (= NNRbRc) Rc, C (= NN (C (= O) Rb) Rc) Rc, C (= NN (C = O) ORC) ( RC) 2, S (= O) o (= NRb) qRc, or N = CRbRc; - each Ra, independently, is halogen, Ci-Cβ alkyl, Ci-Cβ haloalkyl, Ci-C alkoxy, Ci-Ce haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C3-Cβ cycloalkyl, CN, ORC, NRbRc , NO2, C (= O) (O) PRC, OC (= O) (O) PRe, C (= O) NRbRc, OC (= O) NRbRe, NRbC (= O) (O) PRe, NRbC (= O) NRbRc, C (= S) NRbRc, S (0) mRb, SO2NRbRc, OSO2RC, OSO2NRbRc, NRbSO2Rc, NRbSO2NRbRc, N = S (= O) PRCRC, S (= O) o (= NRb) qRc, SFβ, OCN, SCN, Si (Rd) 3 or a saturated, or partially unsaturated or aromatic, three- to six-membered carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N (Rc) p, O, and S, which can be oxidized, and in which the groups mentioned above and the carbo- or heterocyclic ring can be partially or totally replaced by Raa or - two geminally linked Ra groups, together, can form a group selected from = 0, = S, = CRbRc, = NRC, = NORC, e = NNRCRC; - each Raa, independently, is halogen, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy or Ci-Ce haloalkoxy; - each Rb, independently, is hydrogen, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-C alkoxy, Ci-Ce haloalkoxy or a saturated, partially unsaturated or aromatic three to six membered carbo- or heterocyclic ring, which it can contain 1 to 3 heteroatoms selected from N (Rc) p, O, and S, where S can be oxidized and where the carbo- or heterocyclic ring can be partially or totally replaced by Raa; - each Rc, independently, is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylcarbonyl, Ci-Ce cycloalkyl, or a saturated, partially unsaturated or aromatic three- to six-membered carbon- or heterocyclic ring, which it can contain 1 to 3 heteroatoms selected from N (Raa) p, O and S, where S can be oxidized and where the carbo- or heterocyclic ring can be partially or totally replaced by Raa; - in which two groups RbRb, RcRbor RCRC twinned together or together with the atom to which they are attached, can form a 3, 4, 5, 6 or 7 membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which can contain from 1 to 2 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO2 and in which the carbo- or heterocyclic ring can be partially or totally replaced by R3; - each Rd, independently, is hydrogen, phenyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, or C 1 -C alkoxyalkyl, where the groups mentioned above can be replaced by one or more halogens; - each Re, independently, is C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylcarbonyl, C-Cβ cycloalkyl, or a saturated, partially unsaturated or aromatic 3- to six-membered carbo- or heterocyclic ring, which may contain from 1 to 3 heteroatoms selected from N (Raa) p, O and S, where S can be oxidized and where the carbo- or heterocyclic ring can be partially or totally replaced by Raa; - n is 0, 1 or 2; - m is 0, 1, or 2; - p is 0 or 1; - R2 is H, halogen, CN, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C10 cycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, Cβ-Cu cycloalkylalkyl, Cyl-cycloalkyl, C1-6 alkyl or C3-Cβ cycloalkenyl, where the groups mentioned above may be unsubstituted, partially, or completely substituted by R2a, or R2 may form a three to ten membered carb- or heterocyclic ring or a seven to eleven membered ring system , where the ring or ring system can be saturated, partially unsaturated, or aromatic, and where the ring or ring system can contain 1 to 4 heteroatoms selected from N (RC) P, O, and S, where S can be oxidized, and where the carbo- or heterocyclic ring or ring system can be unsubstituted, partially or totally replaced by R2a; - with the proviso that if R2 is halogen or CN, then Z is a direct bond; - each R2a, independently, is halogen, Ci-Cβ alkyl, Ci-Cβ haloalkyl, Ci-Cβ alkoxy, Ci-Cβ haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CN, ORC, NRbRc , NO2, C (= O) (O) PRc, OC (= O) (O) PRe, C (= O) NRbRc, OC (= O) NRbRe, NRbC (= O) (O) PRe, NRbC (= O) NRbRc, C (= S) NRbRc, S (O) mRb, Sθ2NRbRc, OSO2RC, 0S02NRbRc, NRbS02Rc, NRbS02NRbRc, SFβ, OCN, SCN, Si (Rd) 3, C (= N (O) pRb) Rb, C (= NNRbRc) Rb, C (= NN (C (= O) OPRc) Rc) Rb, ON = CRbRc, ONRbRc, S (= O) o (= NRb) qRc, SO2NRb (= O) NRbRc, P ( = X2) RbRθ, OP (= X2) (OPRc) Rb, OP (= X2) (ORC) 2, N = CRbRc, NRbN = CRbRc, NRbNRbRc, NRbC (= S) NRbRc, NRbC (= NRb) NRbRc, NRbNRbC (= X2) NRbRc, NRbNRbSO2NRbRc, N = S (= O) pRcRc, or a saturated, partially unsaturated or aromatic 3- to 6-membered carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N - (RC) P, O, and S, where S can be oxidized, and where the groups mentioned above and the carbo- or heterocyclic ring can be partially or totally replaced by R2aa, or; - two groups R2a twinned together, can form a group selected from = 0, = S, = CRbRc, = NRC, = NORC, and = NNRCRC; - each R2aa, independently, is halogen, Ci-Cβ alkyl, Ci-Cβ haloalkyl, Ci-Cβ alkoxy, Ci-Cβ haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C3-Cβ cycloalkyl, CN, ORC, NRbRc , NO2, C (= O) (O) PRC, OC (= O) (O) PRe, C (= O) NRbRc, OC (= O) NRbRe, NRbC (= O) (O) PRe, NRbC (= O) NRbRc, C (= S) NRbRc, S (0) mRb, SO2NRbRc, OSO2RC, 0S02NRbRc, NRbSO2Rc, NRbS02NRbRc, SFs, OCN, SCN, Si (Rd) 3, C (= N (O) PRb) Rb, C (= NNRbRc) Rb, C (= NN (C (= O) OPRc) Rb) Rb, ON = CRbRc, ONRbRc, S (= O) o (= NRb) qRc, S02NRb (= 0) NRbRc, P ( = X2) RbRc, OP (= X2) (OPRc) Rb, OP (= X2) (ORC) 2, N = CRbRc, NRbN = CRbRc, NRbNRbRc, NRbC (= S) NRbRc, NRbC (= NRb) NRbRc, NRb -NRbC (= X2) NRbRc, NRbNRbSO2NRbRc, or N = S (= O) PRCRC, or - two groups R2aa twinned together can form a group selected from = 0, = S, = CRbRc, = NRC , = NORC, e = NNRCRC; C4, C3-C6 cycloalkyl, CN, ORC, NRbRc, NO2, C (= O) (O) PRC, OC (= O) (O) PRe, C (= O) NRbRc, OC (= O) NRbRe, NRbC (= O) (O) PRe, NRbC (= O) NRbRc, C (= S) NRbRc, S (O) mRb, Sθ2NRbRc, OSO2RC, OSO2NRbRc, NRbSO2Rc, NRbSO2NRbRc, SFs, OCN, SCN, Si (Rd) 3 , C (= N (O) pRb) Rb, C (= NNRbRc) Rb, C (= NN (C (= O) OPRc) Rb) Rb, ON = CRbRc, ONRbRc, S (= O) o (= NRb ) qRc, SO2NRb (= O) NRbRc, P (= X2) RbRc, OP (= X2) (OPRc) Rb, OP (= X2) (ORC) 2> N = CRbRc, NRbN = CRbRc, NRbNRbRc, NRbC (= S) NRbRc, NRbC (= NRb) NRbRc, NRbNRbC (= X2) NRbRc, NRbNRbSO2NRbRc, or N = S (= O) PRCRC, or - two R3 geminally linked groups, together, can form a group selected from = 0, = S, = CRbRc, = NRC, = NORC, e = NNRCRC; - and / or stereoisomers or agriculturally or veterinarily acceptable salts or tautomers or N-oxides thereof.
[005] The substituted pyrimidinium compounds of Formula (I), and their agriculturally acceptable salts are highly active against animal pests, that is, harmful arthropod and nematode species, especially against insects and Acaridae that are difficult to control.
[006] In addition, the present invention relates to and includes the following embodiments: - compositions comprising at least one compound of Formula (I), as defined above; - agricultural and veterinary compositions comprising an amount from at least one compound of Formula (I) or an enantiomer, diastereomer or salt thereof, as defined above; - a method for combating invertebrate pests, infestation or infection with invertebrate pests, that method includes contacting said pest or its supply of food, habitat or breeding ground with an effective amount as a pesticide, at least at least, a compound of Formula (I), as defined above, or a composition thereof; - a method for the control of invertebrate pests, against infestation and infection by invertebrate pests, this method comprises the contact of said pest or its supply of food, habitat or breeding ground with an effective amount as a pesticide, at least at least one compound of Formula (I) as defined above or a composition comprising at least one compound of Formula (I); - a method for the prevention or protection against invertebrate pests that comprises contact of the invertebrate pests, or their supply of food, habitat or breeding ground with the substituted pyrimidinium compounds of General Formula (I), as defined above , or a composition comprising at least one compound of Formula (I), as defined above, or a composition comprising at least one compound of Formula (I); - a method for the protection of crops, plants, plant propagating material and / or plants growing from attack or infestation by invertebrate pests comprising contact with or treatment of crops, plants, plant propagation material and plants in growth, or the soil, material, surface, space, area or water in which the crops, vegetables, plant propagating material is stored or the plant grows, with a pesticide-effective amount of at least one Formula ( I), as defined above, or a composition comprising at least one compound of Formula (I); - a non-therapeutic method for the treatment of animals infested or infected by parasites or the prevention of animals from being infected or infested by parasites or the protection of animals against infestation or infection by parasites comprising oral, topical or oral administration or application parenterally to animals a parasiticidal amount of a compound of Formula (I), as defined above, or a composition comprising at least one compound of Formula (I); - a method for the treatment, control, prevention or protection of animals against infestation or infection by parasites through the application or oral, topical or parenteral administration to animals of a substituted Formula (I) pyrimidinium compound, as defined above, or a composition that comprises at least one compound of Formula (I); - the seed comprising a compound of Formula (I), as defined above, in an amount from 0.1 g to 10 kg per 100 kg of seeds; - the use of the compounds of Formula (I), as defined above, for the protection of growing plants or plant propagating material from attack or infestation by invertebrate pests; - the use of the compounds of Formula (I) or their enantiomers, diastereomers or veterinarily acceptable salts to combat pests in and on animals; - a process for the preparation of a veterinary composition for the treatment, control, prevention or protection of animals against infestation or infection by parasites, which comprises the addition of a parasiticide effective amount of a compound of Formula (I) or the its enantiomers, diastereomers and / or veterinarily acceptable salt to a carrier composition suitable for veterinary use; - the use of a compound of Formula (I) or its enantiomers, diastereomers and / or veterinarily acceptable salt, for the preparation of a medicine for the treatment, control, prevention or protection of animals against infestation or infection by parasites.
[007] All compounds of the present invention, including, if applicable, their stereoisomers, their tautomers, their salts or their N-oxides, as well as their compositions are especially useful for the control of invertebrate pests, in particular especially for the control of arthropods and nematodes and especially insects. Accordingly, the present invention relates to the use of a compound, as described in the present invention, for combating or controlling invertebrate pests, in particular, the invertebrate pests of the group of insects, arachnids or nematodes.
[008] The term "compound (s) according to the present invention", or "compounds of Formula (I)", as used in the present invention, refers to and comprises the compound (s) as defined at present, and / or its stereoisomer (s), salt (s), tautomer (s) or N-oxide (s). The term "compound (s) of the present invention" is to be understood as being equivalent to the term "compound (s) according to the present invention", therefore, it also comprises the stereoisomer (s), salt (s) ), tautomer (s) or N-oxide (s) of the compounds of Formula (I).
[009] The term "composition (s) according to the present invention" or "composition (s) of the present invention" encompasses the composition (s) comprising at least one compound of Formula (I), according to the present invention, as defined above, therefore, also including a stereoisomer, an agriculturally or veterinarily acceptable salt, tautomer or an N-oxide of the compounds of Formula (!) ■
[010] The substituted pyrimidinium compounds of Formula (I) according to the present invention have not yet been described for pesticide uses or applications in the agricultural pesticide industry or veterinary practice.
[011] Substituted heterocyclic pyridinium derivatives and their use as pesticides have been described in publication WO 2009/099929, as well as in publications WO 2011/017347 and WO 2011/017351.
[012] However, substituted pyrimidinium compounds especially of Formula (I) with the characteristic substitution pattern as defined in the present invention have not yet been described.
[013] Depending on the substitution pattern, compounds of Formula (I) may have one or more chirality centers, in the case that they are present as mixtures of diastereomers or enantiomers. The present invention provides the individual pure enantiomers or the pure diastereomers of the compounds of Formula (I), and mixtures thereof and the use, in accordance with the present invention, of the pure enantiomers or pure diastereomers of the compound of Formula (I) or their mixtures. Suitable compounds of Formula (I) also include all possible geometric stereoisomers (isomers w / w / trans) and mixtures thereof. Cis / trans isomers may be present in relation to an alkene, carbon-nitrogen double bond or amide group. The term “stereoisomer (s)” encompasses optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one chirality center in the molecule, as well as geometric isomers (cis / trans isomers). refers to all possible stereoisomers of the compounds of Formula (I), that is, the individual enantiomers or diastereomers, as well as their mixtures.
[014] Depending on the substitution pattern, the compounds of Formula (I) may be present in the form of their tautomers. Accordingly, the present invention also relates to tautomers of Formula (I) and to stereoisomers, tautomers and salts, N-oxides of said tautomers.
[015] The compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) or modifications that may have different macroscopic properties, such as stability or have different biological properties, such as activity. The present invention relates to the amorphous and crystalline compounds of Formula (I), to mixtures of different crystalline states or modifications of said compound I, as well as the salts of these amorphous or crystalline products.
[016] The salts of the compounds of Formula (I) are preferably the agriculturally or veterinarily acceptable salts. They can be formed in a usual method, for example, by reacting the compound with an acid of the anion in question, if the compound of Formula (I) has a base functionality or by reacting an acidic compound of Formula (I ) on an adequate basis.
[017] Suitable agriculturally or veterinarily useful salts are especially the cations or acid addition salts of these acids, whose cations and anions, respectively, have no adverse effect on the action of the compounds according to the present invention. Suitable cations, in particular, are alkali metal ions, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium, magnesium and barium, and transition metals, preferably manganese, copper, zinc and iron, as well as ammonium (NH4 +) and substituted ammonium, where 1 to 4 of the hydrogen atoms are replaced by C1-C4 alkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy, alkoxy- C1-C4-C1-C4-alkyl, hydroxy-C1-4 alkoxy-C1-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyethoxy) ethylammonium, bis (2-hydroxyethylethyl) addition, phosphonium ions, sulfonium ions, preferably tri (C1-C4 alkyl) sulfonium and sulfoxonium ions, preferably tri (C-C4 alkyl) sulfoxonium.
[018] Anions of useful acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and anions of the C1-C4 alkanoic acids, preferably the formate, acetate, propionate and butyrate. They can be formed by reacting a compound of Formula I with a corresponding anion acid, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
[019] The term "N-oxide" includes any compound of the present invention, containing at least one tertiary nitrogen atom which is oxidized to a portion of N-oxide.
[020] The organic portions mentioned in the definitions above the variables are - like the term halogen - collective terms for the individual lists of the individual members of the group. The prefix Cn-Cm indicates, in each case, the possible number of carbon atoms in the group.
[021] The term "halogen" means fluorine, bromine, chlorine and iodine, in particular fluorine, chlorine or bromine.
[022] The term “partially or fully halogenated” means that 1 or more, for example, 1,2, 3, 4 or 5 or all the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular, fluorine or chlorine.
[023] The term "Cn-Cm alkyl" as used herein (and also in Cn-Cm alkylamino, Cn-Cm di-alkylamino, Cn-Cm alkylaminocarbonyl, di- (Cn-Cm alkylamino) carbonyl, Cn- alkylthio Cm, alkylsulfinyl Cn-Cm and alkylsulfonyl Cn-Cm) refers to a saturated, branched or unbranched hydrocarbon group containing, for example, 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. The term "C1-C4 alkyl" means, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.
[024] The term "Cn-Cm haloalkyl" as used herein (and also in Cn-Cm haloalkylsulfonyl and Cn-Cm haloalkylsulfonyl) refers to a straight or branched chain alkyl group with, for example, carbon atoms , from 1 to 10, in particular from 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms of these groups can be replaced by halogen atoms, as mentioned above, for example, haloalkyl C1-C4, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 chloroethyl, 1-bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2-fluoroethyl, 2-fluoroethyl 2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term "C1-C4 haloalkyl", in particular, comprises fluoroalkyl C1-C2, 0 which is synonymous with methyl or ethyl, where 1,2, 3, 4 or 5 hydrogen atoms are replaced by fluorine atoms, such as such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.
[025] Similarly, the terms "Cn-Cm alkoxy" and "Cn-Cm alkylthio" (or Cn-Cm alkylsulfenyl, respectively) refer to straight or branched alkyl groups containing carbon atoms, for example , from 1 to 10, in particular, from 1 to 6 or from 1 to 4 carbon atoms (as mentioned above), linked through oxygen bonds (or sulfur bonds, respectively), at any bond in the alkyl group. Examples include C1-C4 alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, additional C1-C4 alkylthio, such as methylthio, ethyl, propyl, isopropyl, and n -butylthio.
[026] Consequently, the terms "haloalkoxy Cn-Cm" and "haloalkylthio Cn-Cm" (or haloalkylsulfenyl Cn-Cm, respectively) refer to the alkyl groups of straight or branched chains containing, in particular, carbon atoms, for example 1 to 10, in a particle of 1 to 6 or from 1 to 4 carbon atoms (as mentioned above), linked via oxygen or sulfur bonds, respectively, to any bond in the alkyl group, where some or all of the hydrogen atoms of these groups can be replaced by halogen atoms, as mentioned above, for example, the C1-C2 haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, chlorofluoromethoxy, dichloro -chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2 -dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy, additional C1-C2 halogenoalkylthio, such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, fluoromethylthio, 2-fluoroethylthio, 2-fluoroethyl 2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichlorethylthio and pentafluoroethylthio ee similar. Similarly, the terms "C1-C2 fluoroalkoxy" and "C-C2 fluoroalkylthio" refer to C1-2 fluoroalkyl that is linked to the rest of the molecule by means of an oxygen atom or a sulfur atom, respectively.
[027] The term "C2-Cm alkenyl", as used herein, means an unsaturated, branched or unbranched hydrocarbon group containing 2 am, for example 2 to 10 or 2 to 6 carbon atoms and a bond double in any position, such as ethylene, 1-propenyl, 2-propenyl, 1-methyl-ethylenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1- propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3- methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2- propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl- 1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2- methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1- butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3- butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1- butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butyl, 2-ethyl-2- butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl- 2-methyl-2-propenyl.
[028] The term “Cs-Cm alkynyl”, as used herein, refers to a branched or unbranched unsaturated hydrocarbon group containing 2 am, for example 2 to 10 or 2 to 6 atoms of carbon and containing at least one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.
[029] The term "Cn-Cm-Cn-Cm alkoxy", as used herein, refers to alkyl containing carbon atoms, for example, as specific examples mentioned above, in which a hydrogen atom of the radical alkyl is replaced by a Cn-Cm alkoxy group; wherein the value of n and m of the alkoxy group, independently, is selected from the alkyl group.
[030] The suffix "carbonyl" in a group or "C (= O)" indicates a group in which, in each case, the group is linked to the rest of the molecule through a carbonyl group (C = O). This is the case, for example, in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.
[031] The term "aryl" as used herein, refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical, such as the phenyl or naphthyl radical, in particular phenyl (also referred to as CθHs as a substituent) .
[032] The term "ring system" means two or more rings directly connected.
[033] The term "Ca-Cm cycloalkyl", as used herein, refers to a monocyclic ring saturated with the 3-membered cycloaliphatic radicals, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.
[034] The term "alkylcycloalkyl" also indicates the term "alkyl that can be substituted by cycloalkyl" an alkyl group that is replaced by a cycloalkyl ring, where alkyl and cycloalkyl are as defined herein.
[035] The term "cycloalkylalkyl" also means the term "cycloalkyl that can be substituted by alkyl" a cycloalkyl ring that is replaced by an alkyl group, where alkyl and cycloalkyl are as defined herein.
[036] The term "alkylcycloalkylalkyl" also indicates the term "alkylcycloalkyl that can be substituted for alkyl" an alkylcycloalkyl group, which is replaced by an alkyl group, where alkyl and alkylcycloalkyl are as defined herein.
[037] The term "C3-Cm cycloalkenyl", as used herein, refers to a monocyclic ring of partially unsaturated cycloaliphatic radicals of 3 to m members.
[038] The term "cycloalkylcycloalkyl" also means the term "cycloalkyl that can be substituted by cycloalkyl" a cycloalkyl substitution on another cycloalkyl ring, in which each cycloalkyl ring, independently, has 3 to 7 members of the ring of carbon atoms and the cycloalkyl groups are linked through a single bond or contain a common carbon atom. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (for example, 1,1'-bicyclopropyl-2-yl), cyclohexylcyclohexyl in which the two rings are connected through a single common carbon atom (for example, the 1,1-bicycle -2-yl), cyclohexylcyclopentyl in which the two rings are connected through a single bond (for example, 4-cyclopentylcyclohexyl) and their different stereoisomers, such as (1R, 2S) - 1,1 '- bicyclopropyl-2-yl and (1R, 2R) -1,1-bicyclopropyl-2-yl.
[039] The term "3- to 6-membered carbocyclic ring", as used herein, refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings.
[040] The term “3, 4, 5, 6 or 7-membered aromatic, saturated, partially unsaturated heterocyclic ring that may contain 1,2, 3 or 4 heteroatoms” or “containing the groups of heteroatoms”, where the (s) heteroatom group (s) is (are) selected from N (N-substituted groups), O and S (substituted S groups) as used herein, refers to monocyclic radicals, monocyclic radicals they can be saturated, partially unsaturated or aromatic (completely unsaturated). The heterocyclic radical can be attached to the rest of the molecule through a carbon ring member or through a nitrogen ring member.
[041] Examples of 3, 4, 5, 6 or 7-membered saturated heterocyclic or heterocyclyl rings include oxiranyl, aziridinyl, azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 5-isoxazolidinyl thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2, 4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4- thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxane-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl a, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4 hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1 -oxothiomorfolin-2-yl, 1-oxothiomorfolin-3-yl, 1,1-dioxothiomorfolin-2-yl, 1,1-dioxothiomorfolin-3-yl, hexaidroazepin-1-, -2-, -3- or -4 -il, hexahydroxepinyl, hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl, hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl, hexahydro-1,3-dioxepinyl, hexahydro-1,4 -dioxepinyl and the like.
[042] Examples of 3, 4, 5, 6 or 7-membered partially unsaturated heterocyclic or heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4- dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrotien-2-yl, 2,4- dihydrotien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin- 3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5- useful, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-i1, 4-isothiazolin-3-i1, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydroppyrazol-1-yl, 2,3-dihydropyrazole-2- useful, 2,3-dihydroppyrazol-3-yl, 2,3 dihydroppyrazol-4-yl, 2,3-dihydroppyrazol-5-yl, 3,4-dihydroppyrazol-1-yl, 3,4 dihydroppyrazol-3-yl, 3,4-dihydroppyrazol-4-yl, 3,4-dihydroppyrazol-5-yl, 4,5 dihydroppyrazol-1-yl, 4,5-hydropyrazol-3-yl, 4,5-dihydroppyrazol-4-i 1,4,5-dihydropyrazol-5-yl, 2,3-dihydroxazol-2-yl, 2,3-dihydroxazol-3-yl, 2,3-dihydroxazol-4-yl, 2,3-dihydroxazole-5- yl, 3,4-dihydroxazol-2-yl, 3,4-dihydro-3-yl, 3,4-dihydroxazol-4-yl, 3,4-dihydro-5-yl, 3,4-dihydro-2- useful, 3,4-dihydroxazol-3-yl, 3,4-dihydroxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4- di or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di or tetrahydropyrimidinyl, diou tetrahydropyrimidinyl, 1,3,5-di- or tetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro [1H] azepine-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3 , 4,5,6-tetrahydro [2H] azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro [1H] azepine- 1 -, -2 -, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1H] azepine-1-, -2-, - 3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro [1H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7- tetrahydro [1H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl , 2,3,6,7 tetrahydro [1 H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl, tetrahydro- 1,3- oxazepinyl, tetrahydro-1,4-oxazepinyl, tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.
[043] Examples of 5- or 6-membered heteroaromatic or heterocyclic aromatic rings (hetaryl) are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazole-2- useful, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
[044] The term "C2-Cm alkylene" is an aliphatic, saturated divalent chain, preferably branched or unbranched, containing 2 am, for example, 2 to 7 carbon atoms, for example, CH2CH2, -CH (CH3) -, CH2CH2CH2, CH (CH3) CH2, CH2CH (CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.
[045] The preferred embodiments and compounds of the present invention for use in pesticide and insecticide methods for application purposes are described in the following paragraphs.
[046] The observations made below regarding the preferred realizations of the variables (substituents) of the compounds, according to the present invention, especially regarding their substituents X, Y, Z, X1, X2, Y1, A, R1, Ra , Raa, Rb, RC Rd, Re, R2, R2a R2aa, R3, m, n, pθ Hθt ARE VALID in isolation and, in particular, in each possible combination between them and, if appropriate, the uses, methods and compositions according to the present invention.
[047] In a special embodiment, the variables of the compounds of Formula (I) have the second meanings, these meanings, alone or in combination with each other, being special realizations of the compounds of Formula (I):
[048] In a preferred embodiment of the compounds of Formula (I), X is O. These compounds correspond to the compounds of Formula (1.1).
[049] In another embodiment of the compounds of Formula (I), X is S. These compounds correspond to the compounds of Formula (I.2).

[050] In another embodiment of the compounds of Formula (I), Y is S. These compounds correspond to the compounds of Formula (I.A).
[051] In another embodiment of the compounds of Formula (I), Y is O. These compounds correspond to the compounds of Formula (IB).

[052] In another embodiment of the compounds of Formula (I), Y is the S and X is the O. These compounds correspond to the compounds of Formula

[053] In another embodiment of the compounds of Formula (I), Y is S and X is S. These compounds correspond to the compounds of Formula (I.2.A).

[054] In another embodiment of the compounds of Formula (I), Y is O and X is O. These compounds correspond to the compounds of Formula (I.1.B).

[055] In another embodiment of the compounds of Formula (I), Y is O and X is S. These compounds correspond to the compounds of Formula (I.2.B).

[056] Within these embodiments, the compound of Formula (1.1.B) is preferred.
[057] In a reaction of the compounds of Formula (i), Z is a Het O Het S Het O direct bond or C (RaRaa) 0.
[058] In another embodiment of the compounds of Formula (I), Z is a direct bond.
[059] In one embodiment of the compounds of Formula (I), Z is O, S (O) m, NRb, C (= X1), C (= X1) Y1, or Y1C (= X1)). In another embodiment, Z is O, S (O) m, or NRb. In another embodiment, Z is C (= X1), C (= X1) Y1, or Y1C (= X1).
[060] In an embodiment of the compounds of Formula (I), X1 is O.
[061] In an embodiment of the compounds of Formula (I), X1 is S.
[062] In an embodiment of the compounds of Formula (I), X1 is NRb.
[063] In one embodiment of the compounds of Formula (I), Y1 is O.
[064] In an embodiment of the compounds of Formula (I), Y1 is S.
[065] In one embodiment of the compounds of Formula (I), Y1 is the NRC.
[066] In one embodiment of the compounds of Formula (I), A is CH or N, and in which the nitrogen of the pyrimidinium ring taken together with the contiguous carbon atom and A, as represented in Formula (I) , forms a five- or six-membered ring, in which each remaining ring member is selected from carbon atoms and up to a heteroatom independently selected from O, S, and N (RC) P, where each ring can be replaced by up to a Ra, where Ra has the meaning, as described below.
[067] In another embodiment of the compounds of Formula (I), A is CH or N, and in which the nitrogen of the pyrimidinium ring taken together with the contiguous carbon atom and A, as represented in Formula ( I), forms a five-membered ring, where each member of the remaining ring is selected from carbon atoms and up to a heteroatom independently selected from O, S, and N (RC) P.
[068] In another embodiment of the compounds of Formula (I), A is CH or N, and in which the nitrogen of the pyrimidinium ring taken together with the contiguous carbon atom and A, as represented in Formula ( I), forms a six-membered ring, in which each member of the remaining ring is selected from carbon atoms and up to a heteroatom independently selected from O, S, and N (RC) P.
[069] In another embodiment, compounds of Formula (I), in which A is CH, and in which the nitrogen of the pyrimidinium ring taken together with the contiguous carbon atom and A, as shown, are preferred in Formula (I), it forms a five or six membered ring resulting in the compounds of Formula (II) selected from the group of compounds of Formulas 11-1 to 11-15:

[070] In another embodiment, compounds of Formula (I) are selected from the group of compounds of Formulas 11-1, II-2, II-3, II-4, II-5, II-6, II -7 and 11-15.
[071] In another embodiment, the compounds of Formula (I) are selected from the group of compounds of Formulas 11-1, II-2, II-3, II-4, II-5, II-6 and II -7.
[072] In a preferred embodiment, the compounds of Formula (I) is a compound of Formula 11-1.
[073] In another embodiment, the compound of Formula (I) is a compound of Formula 11-15.
[074] In another embodiment, the compound of Formula (I) is a compound of Formula 11-16.
[075] In one embodiment, R1 is hydrogen, C1-Cs alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C4-C10 cycloalkenyl or C5-C11 cycloalkylalkyl, where the C atoms of the groups mentioned above can be unsubstituted, or partially or completely replaced by Ra, where Ra has the meaning, as described below.
[076] In another embodiment, R1 is a three to ten membered, saturated, or partially saturated heterocyclic ring system that can contain 1 to 3 heteroatoms selected from N (RC) P, O, and S , where S can be oxidized and which heterocyclic ring can be unsubstituted or substituted by Ra.
[077] In another embodiment, R1 is hydrogen, C1-C4 alkyl, C2-C8 alkenyl, Ci-Ce alkoxy, C3-C6 cycloalkyl or C5-C11 cycloalkylcycloalkyl, in which the C atoms of the groups mentioned above can be unsubstituted, or partially or totally replaced by halogen atoms.
[078] In another embodiment R1 is C1-C4 alkyl, C2-Ce alkenyl, C3-C6 cycloalkyl, phenyl or benzyl, in which the C atoms of the groups mentioned above can be unsubstituted, or partially or totally replaced by Ra, where Ra has the meaning, as described below.
[079] In another embodiment R1 is C1-C4 alkyl, C3-C6 cycloalkyl or phenyl, wherein the C atoms of the groups mentioned above can be unsubstituted, or partially or totally substituted by halogen or C1-C4 alkyl.
[080] In another embodiment R1 is C1-C4 alkyl, C2-C4 alkenyl, phenyl or benzyl, in which the C atoms of the groups mentioned above can be partially or completely replaced by halogen, preferably Cl or F .
[081] In another embodiment R1 is C1-C4 alkyl, C3-C6 cycloalkyl or phenyl, preferably 0 CH3, CH2CH3, CH (CH3) 2, cyclopropyl or phenyl.
[082] In another embodiment R1 is C1-C3 alkyl, preferably CH3, CH2CH3 or CH (CH3) 2; especially, R1 is CH2CH3.
[083] In one embodiment, R2 is hydrogen, halogen, CN, NO2, C1-C6 alkyl, Ci-Ce haloalkyl, Ci-Cβ haloalkoxy, Ci-Cθ alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3 cycloalkyl -C6, Cs-Cβ cycloalkenyl, C5-C14 cycloalkylcycloalkyl or S (0) mRb, wherein the C atoms of the groups mentioned above can be unsubstituted, or partially or totally substituted by R2a.
[084] In one embodiment, R2 is hydrogen, halogen, CN, C1-C6 alkyl, C1-C2 alkoxy, C1-C2 alkyl or C3-C6 cycloalkyl, in which the C atoms of the groups mentioned above can be substituted by halogen or CN.
[085] In one embodiment, R2 is hydrogen, halogen, CN or C1-C4 alkyl that can be replaced by halogen.
[086] In another realization R2 is the CN.
[087] In another embodiment, R2 is hydrogen or C1-C2 alkyl, especially CH3.
[088] In another embodiment, R2 is C-i-Cβ haloalkyl, of prθfθi-θncia, C1-C2 haloalkyl, especially halomethyl, such as CF3 or CHF2.
[089] In another embodiment, R2 is C1-C2 alkoxy-C1-C2 alkyl, preferably C1-C2 alkoxymethyl, especially CH2OCH3.
[090] In another embodiment, R2 is C3-C6 cycloalkyl, preferably cyclopropyl, which can be substituted, preferably, by halogen or cyan atoms.
[091] In another embodiment, R2 is C2-Ce alkyl, preferably C2-C4 alkyl, especially CH2CH3 or C (CH3) 3.
[092] In another embodiment, R2 is C1-Cβ alkyl, preferably C1-C2 alkyl, especially CH3.
[093] In another embodiment, R2 is halogen, preferably 0 Cl or F, especially F.
[094] In another embodiment, R2 is a five- or six-membered carb- or heterocyclic ring, that ring may be unsubstituted, partially or fully replaced by R2a, and where R2a is as defined below or R2a, from preferably, it is halogen, Ci-Ce haloalkyl, C-Cβ haloalkoxy, ORC, C (= O) ORC, C (= O) NRbRc, phenyl, or pyridyl that can be replaced by halogen, Ci-Ce haloalkyl or Ci haloalkoxy -Ce.
[095] In another embodiment, R2 is a six-membered carb- or heterocyclic ring, that ring can be unsubstituted, partially or totally replaced by R2a, and where R2a is halogen, C1- Ce haloalkyl, C1- haloalkoxy Ce, ORC, C (= O) ORc, C (= O) NRbRc, phenyl, or pyridyl that can be replaced by R2aa, where R2aa is as defined below.
[096] In another embodiment, R2 is a six-membered aromatic carbocyclic ring, that ring can be unsubstituted, partially or fully replaced by R2a, and where R2a is 0 halogen, haloalkyl Ci-Ce, haloalkoxy Ci-Ce , ORC, C (= O) ORc, C (= O) NRbRc, phenyl, or pyridyl which can be replaced by R2aa, where R2aa is as defined below, preferably R2aa is halogen, haloalkyl Ci-Ce or haloalkoxy Ci-Ce.
[097] Within this realization, R2 is phenyl that can be replaced by halogen, Ci-Ce haloalkyl OR Ci-Cβ haloalkoxy.
[098] Furthermore, within this realization R2 is the phenyl that can be replaced by phenyl.
[099] In another embodiment, R2 is a six-membered heterocyclic ring, containing 1 or 2, preferably 1, heteroatom (s) selected from N-Rc, O, and S, where S can be oxidized, wherein the heterocyclic ring is unsubstituted or substituted by one or more groups from among R2a, where R2a is as defined below.
[100] In one embodiment, Ra is halogen, Ci-Cβ alkyl, Ci-Cβ haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3-C6 cycloalkyl, CN, ORC, NRbRc, NO2, phenyl, pyridyl, thiazila , furanyl, pyrimidinyl or thienyl, where the C atoms mentioned above, the groups can be unsubstituted or replaced by one or more Raa, where Raa is as defined below.
[101] In another embodiment, Ra is 0 halogen, C1-C4 alkyl, C1-C4-haloalkyl or C3-C6 cycloalkyl.
[102] In another embodiment, Ra is 0 halogen, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl.
[103] In another embodiment, Ra is halogen.
[104] In one embodiment, Ra is halogen, CN, NO2, S (0) mRb, C (O) RC, C (O) ORC, C (O) NRbRc, C (= S) NRbRc, C1- alkyl Cβ, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C-Cβ alkoxy, C2-C6 alkenyloxy or C2-Ce alkynyloxy, where the C atoms of the groups mentioned above may be unsubstituted, partially or totally replaced by Raa, where it is as defined below.
[105] In another embodiment, Ra is halogen, CN, C-Cβ alkyl, Cs-Ce cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Cβ alkoxy, C2-Cβ alkenyloxy or C2-C6 alkenyloxy, wherein the C atoms of the groups mentioned above can be unsubstituted, partially or completely replaced by Raa, where Raa is as defined below.
[106] In another embodiment, Ra is halogen, CN, C-Cβ alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce alkoxy, C2-C6 alkenyloxy or C2-C6 alkynyloxy, wherein the C atoms of the groups mentioned above can be unsubstituted, partially or totally replaced by halogen atoms.
[107] In another embodiment, Ra is halogen, C-Cβ haloalkyl or Ci-Cβ alkoxy.
[108] In another embodiment, Ra is halogen, CN or C1-C2 haloalkyl.
[109] In another embodiment, Ra is C1-C2 halogen or haloalkyl.
[110] In one embodiment, Ra is halogen, preferably Br, Cl or F, especially Cl.
[111] In another embodiment, Ra is C1-C2 haloalkyl, preferably halomethyl, such as CHF2 or CF3, especially CF3.
[112] In one embodiment, two Ra groups twinned together can form a group selected from = 0, = S, = CRbRc, = NRC, = NORC, and = NNRCRC;
[113] In another embodiment, two Ra groups twinned together can form a group selected from = CRbRc, = NRC, = NORC, and = NNRCRC;
[114] In another embodiment, two Ra groups twinned together can form a group selected from = 0, = S and = N (C 1 -C alkyl).
[115] In another embodiment, two Ra groups twinned together can form a group = N (C 1 -Cβ alkyl).
[116] In one embodiment, Rb is hydrogen, Ci-Cβ alkyl, Ci-Cβ haloalkyl, Ci-Cβ alkoxy, Ci-Cβ haloalkoxy, phenyl, pyridyl, thiazil or thienyl, in which the carbon atoms of the groups mentioned above can be replaced by Raa, where Raa is as defined below. In another embodiment, Rb is hydrogen, C-i-Cβ alkyl, Ci-Cθ haloalkyl, Ci-Cβ alkoxy or Ci-Cθ haloalkoxy. In another embodiment, Rb is hydrogen, C-i-Cβ alkyl or Ci-Ce haloalkyl. In one embodiment, Rb is C1-6 alkyl or C-i-Cβ haloalkyl. In one embodiment, Rb is H.
[117] In one embodiment, Rc is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylcarbonyl, C1-C6 cycloalkyl, phenyl, pyridyl, thiazil or thienyl, in which the C atoms of the groups mentioned above can be replaced by Raa, where Raa is as defined below. In another embodiment, Rc is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C-C4 alkylcarbonyl, or C-i-Cβ cycloalkyl. In one embodiment, Rc is hydrogen, C1-C6 alkyl or C1-C6 haloalkyl. In one embodiment, Rc is C1-C6 alkyl or C1-C6 haloalkyl. In one embodiment, Re is 0 H.
[118] In one embodiment, two groups RbRb, RcRbor RCRC geminally linked or together with the atom to which they are attached, can form a 3, 4, 5, 6 or 7 aromatic, saturated, partially unsaturated or aromatic carbo- or heterocyclic ring members, which may contain 1 to 2 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO2 and in which the carbo- or heterocyclic ring can be partially or totally replaced by R3.
[119] In another embodiment, two geminally linked RbRb, RcRb or RCRC groups, together with the atom to which they are attached, can form a 5- or 6-membered, saturated, partially unsaturated or aromatic carbocyclic ring, that ring can be partially or totally replaced by R3 and where R3 is as defined below.
[120] In another embodiment, two geminally linked RbRb, RcRb or RCRC groups, together with the atom to which they are attached, can form a 5- or 6- membered, saturated, partially unsaturated or aromatic 5- or 6-membered ring, which may contain 1 or 2 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO2, where the heterocyclic ring can be partially or totally replaced by R3, and where R3 is as defined below.
[121] In one embodiment, Rd is hydrogen, phenyl, C1-C4 alkyl or C2-C6 alkenyl, where the groups mentioned above can be replaced by one or more halogens. In another embodiment, Rd is C1-C4 alkyl or phenyl, which can be replaced by halogen. In another embodiment, Rc is C1-C4 alkyl, preferably CH3.
[122] In one embodiment, Re is C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylcarbonyl, C1-Cβ cycloalkyl, phenyl, pyridyl, thienyl or thiazyl in which the groups mentioned above can be replaced by Raa, in that Raa is as defined below. In another embodiment, Re is C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylcarbonyl, or CI-CΘ cycloalkyl. In another embodiment, Re is C1-C4 alkyl or C1-C4 haloalkyl.
[123] In one embodiment, Raa is halogen, C 1 -C 6 alkyl or C 1-C 6 haloalkyl. In another embodiment, Raa is the C-i-Cβ alkoxy or C-i-Cδ haloalkoxy. In one embodiment, Raa is halogen.
[124] In one embodiment, R2a is halogen, haloalkyl CI-CΘ, alkoxy Ci-Cδ, haloalkoxy Ci-Cβ, ORC, C (= O) ORC, C (= O) NRbRc, or phenyl, in which the atoms of C of the groups mentioned above can be unsubstituted or substituted by one or more R2aa, where R2aa is as defined below, especially, R2a is halogen, C1-Cβ alkoxy, or C1-C haloalkoxy.
[125] In one embodiment, two twinned R2a groups together can form a group selected from = 0, = S and = N (C 1 -Cβ alkyl).
[126] In one embodiment, R2a is halogen, Ci-Cβ alkyl, Ci-Cβ haloalkyl, Ci-Ce alkoxy, Ci-Cβ haloalkoxy, C3-C6 cycloalkyl, CN, ORC, NRbRc, NO2, phenyl, pyridyl, thiazila , furanyl, pyrimidinyl or thienyl, wherein the C atoms of the groups mentioned above can be unsubstituted or substituted by one or more R2aa, where R2aa is as defined below.
[127] In another embodiment, R2a is halogen, C-C4 haloalkyl or C3-C6 haloalkoxy.
[128] In another embodiment, R2a is the phenyl that can be replaced by one or more R2aa.
[129] In another embodiment, R2a is halogen. In another embodiment, R2a is the Ci-Cβ haloalkyl. In another embodiment, R2a is the Ci-Cβ haloalkoxy.
[130] In another embodiment, R2a is halogen, CN, NO2, S (0) mRb, C (= O) RC, C (= O) ORC, C (O) NRbRc, C (= S) NRbRc, C 1 -C 6 alkyl, C 3-C 6 cycloalkyl, C 2-C 6 alkenyl, C 2-C 6 alkynyl, C 1 -C alkoxy, C 2-C alkenyloxy or C 2-C 6 alkynyloxy, where the C atoms of the groups mentioned above may be unsubstituted, partially or totally replaced by Raa, where it is as defined below.
[131] In another embodiment, R2a is C (= O) ORC or C (= O) NRbRc.
[132] In another embodiment, R2a is halogen, CN, C-Cβ alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, Ci-Ce alkoxy, C2-C6 alkenyloxy or C2-C6 alkynyloxy, wherein the C atoms of the groups mentioned above can be unsubstituted, partially or totally replaced by R2aa, where R2aa is as defined below.
[133] In one embodiment, R2a is Br, Cl or F, especially 0 Cl.
[134] In another embodiment, R2a is C1-C2 haloalkyl, preferably halomethyl, such as CHF2 or CF3, especially CF3.
[135] In one embodiment, R2aa is halogen, CI-CΘ alkyl, Ci-Cθ haloalkyl, Ci-Cθ alkoxy, Ci-Cθ haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CN, N (Ci-Cθ alkyl) (Ci-Cθ alkyl), C (= O) (O) p (C-Cθ alkyl), C (= O) N (Ci-Cθ alkyl) (Ci-Cθ alkyl), S ( O) m (Ci-Cθ alkyl), Sθ2N (C-Cθ alkyl) (Ci-Cθ alkyl), OSO2 (Ci-Cθ alkyl), N (Ci-Cθ alkyl) SO2 (Ci-Cβ alkyl), or S ( = O) p (= N (C 1 -Cθ alkyl)) (C 1 -C 8 alkyl), or two groups R2aa twinned together, can form a group selected from -O, -S and = N (C- alkyl) Cθ).
[136] In one embodiment, R2aa is halogen, Ci-Cθ alkyl, Ci-Cθ haloalkyl, Ci-Cθ alkoxy, Ci-Cθ haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CN, N (Ci-Cθ alkyl) (Ci-Cθ alkyl), C (= O) (O) p (C-Cθ alkyl), C (= O) N (Ci-Cθ alkyl) (Ci-Cθ alkyl), S ( O) m (Ci-Cθ alkyl), Sθ2N (C-Cθ alkyl) (Ci-Cθ alkyl), OSO2 (Ci-Cθ alkyl), N (Ci-Cθ alkyl) Sθ2 (Ci-Cθ alkyl), or S ( = O) p (= N (C 1 -Cθ alkyl)) (C 1 -Cθ alkyl). In another embodiment, two groups R2aa twinned together can form a group selected from = 0, = S and = N (C 1 -Cθ alkyl).
[137] In one embodiment, R3 is halogen, Ci-Cθ alkyl, Ci-Cθ haloalkyl, Ci-Cθ alkoxy, Ci-Cθ haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, Cs-Cθ, CN, N cycloalkyl (Ci-Cθ alkyl) (Ci-Cθ alkyl), C (-O) (O) p (C-Cθ alkyl), C (= O) N (Ci-Cθ alkyl) (Ci-Cθ alkyl), S ( O) m (Ci-Cθ alkyl), Sθ2N (C-Cθ alkyl) (Ci-Cβ alkyl), OSO2 (Ci-Cθ alkyl), N (Ci-Cθ alkyl) S02 (C-Cθ alkyl), S ( = O) P (= N (C1-Cθ alkyl)) (C1-Cθ alkyl), or - two geminally linked R3 groups, together, can form a group selected from = 0, = S and = N (alkyl Ci-Cθ).
[138] In one embodiment, R3a is halogen, Ci-Cθ alkyl, Ci-Cθ haloalkyl, Ci-Cθ alkoxy, Ci-Cθ haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CN, N (Ci-Cβ alkyl) (Ci-Cβ alkyl), C (= O) (O) P (C-Cβ alkyl), C (= O) N (Ci-Cβ alkyl) (Ci-Cβ alkyl), S ( O) m (Ci-Cβ alkyl), Sθ2N (C-Cβ alkyl) (Ci-Cβ alkyl), OSO2 (Ci-Cβ alkyl), N (Ci-Cβ alkyl) Sθ2 (Ci-Cβ alkyl), or S ( = O) P (= N (Ci-Cβ alkyl)) (Ci-Cβ alkyl). In another embodiment, two R3a groups twinned together can form a group selected from = 0, = S and = N (C 1 -C 10 alkyl).
[139] In one realization, m is 0. In another realization, m is 1. In another realization, m is 2.
[140] In one realization, n is 0. In another realization, n is 1. In another realization, n is 2.
[141] In one embodiment, p is 0. In another embodiment, p is 1.
[142] In one embodiment, Het is a 5- or 6-membered, saturated, partially unsaturated or aromatic heterocyclic ring, which may contain 1 to 4 heteroatoms selected from N (RC) P, O and S, where 0 heterocyclic ring is replaced by (Ra) n and the remaining variables in the meaning of Het are as defined above.
[143] In one embodiment, Het is a 5- or 6-membered, saturated, partially unsaturated or aromatic heterocyclic ring, which may contain 1 or 2 heteroatoms selected from N (RC) P, O and S, where the ring heterocyclic is replaced by (Ra) n.
[144] In one embodiment, Het is a five-membered aromatic heterocyclic ring, containing 2 heteroatoms selected from N (RC) P, O and S, where the heterocyclic ring is replaced by (Ra) n.
[145] In one embodiment, Het is a saturated five-membered heterocyclic ring, which contains a heteroatom selected from N (RC) P, O and S, preferably O, where the heterocyclic ring is replaced by (Ra) n.
[146] In one embodiment, Het is a six-membered aromatic heterocyclic ring, containing 2 heteroatoms selected from N (RC) P, O and S, preferably N (RC) P, where the ring heterocyclic is replaced by (Ra) n
[147] In one embodiment, Het is a six-membered aromatic heterocyclic ring, which contains a heteroatom selected from N (RC) P, O and S, preferably N (RC) P, where the ring heterocyclic is replaced by (Ra) n.
[148] In one embodiment, Het is the pyridyl that is replaced by (Ra) n.
[149] In one embodiment, Het is tetrahydrofuryl, which is replaced by (Ra) n.
[150] In another realization, Het is selected from


[151] Whenever used in a structure, the following: # indicates the link to A in Formula (I).
[152] In another embodiment, Het is selected from any of the following ring systems:

[153] In another embodiment, Het is selected from the following ring systems D-2, D-9, D-22, D-25, D-28, D-29 and D-54:
- where Ra is halogen, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkylthio or phenyl; preferably, Ra is halogen or halomethyl.
[154] In another embodiment, Het is selected from the following ring systems D-2, D-9 and D-25:
- where Ra is halogen, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkylthio or phenyl, preferably halogen or C1-C4 haloalkyl; most preferably, Ra is Cl, Br, F or CF 3, most preferably, Ra is Cl or CF3.
[155] In another embodiment, Het is selected from the following D-2, D-25, or D-54 ring systems:
- where Ra is C1-C4 halogen or haloalkyl; preferably, Ra is 0 Cl, Br, F or CF3, more preferably, Ra is Cl or CF3.
[156] In another embodiment, Het is selected from the following ring systems D-2a, D-2b, D-2c, D-25a, D-54a:
- where Ra, independently of each other, is selected from Cl, Br, F and CF3.
[157] In another embodiment, Het is D-2, preferably D-
[158] In another embodiment, Het is D-2a.
[159] In another embodiment, Het is D-25, preferably D-25 replaced by Cl.
[160] In another embodiment, Het is the D-9, preferably the D-9a or D9B.
[161] In another embodiment, Het is the D-56, preferably the D-56a.
[162] In particular, in view of their use, preference is given to the compounds of Formula (I) compiled in the Tables below, these compounds correspond to the compounds of Formulas 1.1.B (that is, where X and Y are the O) and for the preferred compounds of Formula 11-1, II-2, II-3, II-4, II-5, II-6, II-7,11-15, e.g. Each of the groups mentioned for the substituents indicated in the Tables, moreover, are per se, regardless of the combination in which they are mentioned, an especially preferred aspect of the substituent in question. In addition, the individual meaning of a substituent in the Tables constitutes an especially preferred embodiment of the substituents in question. TABLE 1
[163] The compounds of Formula (111-1) which correspond to the compounds of Formula 11-1, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:

[164] The compounds of Formula (III-2) corresponding to the compounds of Formula II-2, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:

[165] The compounds of Formula (III-3) corresponding to the compounds of Formula II-3, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.

[166] The Formula (III-4) compounds that correspond to the Formula II-4 compounds, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.

[167] The Formula (HI-5) compounds that correspond to the Formula II-5 compounds, where X and Y are O, Het is D-2b where Raéo Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 6
[168] The compounds of Formula (III-6) corresponding to the compounds of Formula II-6, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 7
[169] The compounds of Formula (III-7) that correspond to Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 8
[170] The compounds of Formula (III-8) that correspond to the compounds of Formula 11-15, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 9
[171] The compounds of Formula (III-9) which correspond to the compounds of Formula 11-1, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:
TABLE 10
[172] The compounds of Formula (111-10) which correspond to the compounds of Formula II-2, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 11
[173] The compounds of Formula (111-11) which correspond to the compounds of Formula II-3, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 12
[174] The compounds of Formula (111-12) which correspond to the compounds of Formula II-4, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 13
[175] The compounds of Formula (111-13) which correspond to the compounds of Formula II-5, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 14
[176] The compounds of Formula (111-14) that correspond to the compounds of Formula II-6, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 15
[177] The compounds of Formula (111-15) which correspond to the compounds of Formula II-7, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE16
[178] The compounds of Formula (111-16) which correspond to compounds of Formula 11-15, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 17
[179] The compounds of Formula (111-17) that correspond to the compounds of Formula 11-1, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:
TABLE18
[180] The compounds of Formula (111-18) corresponding to the compounds of Formula II-2, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case of a row in Table A:
TABLE19
[181] The compounds of Formula (111-19) which correspond to the compounds of Formula II-3, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case to a row in Table A
TABLE 20
[182] The compounds of Formula (III-20) corresponding to the compounds of Formula II-4, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case to a row in Table A.
TABLE 21
[183] The compounds of Formula (111-21) corresponding to the compounds of Formula II-5, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case to a row in Table A.
TABLE 22
[184] The compounds of Formula (HI-22) which correspond to the compounds of Formula II-6, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case to a row in Table A.
TABLE 23
[185] The compounds of Formula (III-23) corresponding to the compounds of Formula II-7, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case to a row in Table A.
TABLE 24
[186] The compounds of Formula (III-24) corresponding to the compounds of Formula 11-15, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case to a row in Table A.
TABLE25
[187] The Formula (III-25) compounds that correspond to the Formula 11-1 compounds, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A:
TABLE 26
[188] The compounds of Formula (III-26) corresponding to the compounds of Formula II-2, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 27
[189] The compounds of Formula (III-27) which correspond to the compounds of Formula II-3, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 28
[190] The compounds of Formula (III-28) that correspond to compounds of Formula II-4, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 29
[191] The Formula (III-29) compounds that correspond to the Formula II-5 compounds, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 30
[192] The Formula (III-30) compounds that correspond to the Formula II-6 compounds, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE31
[193] The compounds of Formula (111-31) corresponding to those of Formula II-7, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 32
[194] The Formula (III-32) compounds that correspond to the Formula 11-15 compounds, where X and Y are O, Het is D-25a where Ra is S-CH3, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 33
[195] The Formula (III-33) compounds that correspond to the Formula 11-1 compounds, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A:
TABLE 34
[196] The compounds of Formula (HI-34) corresponding to the compounds of Formula II-2, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:
TABLE 35
[197] The compounds of Formula (III-35) corresponding to the compounds of Formula II-3, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 36
[198] The Formula (III-36) compounds that correspond to the Formula II-4 compounds, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 37
[199] The Formula (III-37) compounds that correspond to the Formula II-5 compounds, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 38
[200] The Formula (III-38) compounds that correspond to the Formula II-6 compounds, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 39
[201] The compounds of Formula (III-39) corresponding to the compounds of Formula II-7, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE40
[202] The compounds of Formula (III-40) corresponding to the compounds of Formula 11-15, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 41
[203] The compounds of Formula (111-41) which correspond to the compounds of Formula 11-1, where X and Y are O, Het is D-56a where Ra is O-Me, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A:
TABLE 42
[204] The Formula (III-42) compounds that correspond to the Formula II-2 compounds, where X and Y are O, Het is D-56a where Ra is O-Me, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 43
[205] The Formula (III-43) compounds that correspond to the Formula II-3 compounds, where X and Y are O, Het is D-56a where Ra is O-Me, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 44
[206] The compounds of Formula (111-12) that correspond to the compounds of Formula II-4, where X and Y are O, Het is D-56a where Ra is O-Me, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 45
[207] The compounds of Formula (III-45) which correspond to compounds of Formula II-5, where X and Y are O, Het is D-56a where Ra is O-Me, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 46
[208] The Formula (III-46) compounds that correspond to the Formula II-6 compounds, where X and Y are O, Het is D-56a where Ra is O-Me, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 47
[209] The Formula (III-47) compounds that correspond to the Formula II-7 compounds, where X and Y are O, Het is D-56a where Ra is O-Me, and the combination of R1, ZR2for a compound corresponds, in each case, to a row in Table A.
TABLE 48
[210] The Formula (III-48) compounds that correspond to the Formula 11-15 compounds, where X and Y are O, Het is D-56a where Ra is O-Me, and with the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A.
TABLE 49
[211] The Formula (HI-49) compounds that correspond to the Formula 11-16 compounds, where X and Y are O, Het is D-2b where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:
TABLE 50
[212] The Formula (III-50) compounds that correspond to the Formula 11-16 compounds, where X and Y are O, Het is D-25a where Ra is Cl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:
TABLE 51
[213] The compounds of Formula (111-51) which correspond to the compounds of Formula 11-16, where X and Y are O, Het is D-2c where Ra is Cl and phenyl, and the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:
TABLE 52
[214] The Formula (III-52) compounds that correspond to the Formula 11-16 compounds, where X and Y are O, Het is D-25a where Ra is S-Me, and with the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:
TABLE 53
[215] The compounds of Formula (III-53) corresponding to the compounds of Formula 11-16, where X and Y are O, Het is D-9b, and the combination of R1, ZR2 for a compound corresponds, in each case of a row in Table A:
TABLE 54
[216] The Formula (III-54) compounds that correspond to the Formula 11-16 compounds, where X and Y are O, Het is D-56a where Ra is O-Me, and with the combination of R1, ZR2 for a compound corresponds, in each case, to a row in Table A:






[217] The compound of Formula (I), according to the present invention, can be prepared according to the following synthetic routes, for example, according to the methods for the preparation and schemes for the preparation, as described below .
[218] The compound of Formula (I), according to the present invention, can be prepared, according to, for example, the methods for the preparation and schemes for the preparation, as described below.
[219] The compounds used as starting materials for the syntheses of the compounds according to the present invention, in general, can be prepared using standard methods of organic chemistry. If not specified otherwise, the definitions of the variables, such as the X, Y, Het, R1 and R2 of the structures provided in the diagrams have the same meaning, as defined above.
[220] The compounds of Formula (I), for example, can be prepared by reacting compound P-1 suitably substituted by a P-2 malonate derivative analogous to the methods described by Holyoke et al., In WO 2009 / 099929 (Scheme 1):

[221] Compounds, such as P-1, can be prepared from the corresponding 3-P compounds, by reaction with an amine nucleophile such as P-4, as described, for example, by Michel Langlois et al., Journal of Heterocyclic Chemistry, 19 (1), 193-200; 1982, where LG indicates a leaving group, such as halogen (for example, chlorine or bromine), OR ', or SR', with R 'being C 1 -Cβ alkyl, preferably methoxy ethoxy chlorine , methylthio or ethylthio (Scheme 2):

[222] The compounds, such as P-3, are available from the corresponding P-5 lactams through standard procedures known to the person skilled in the art. For example, see Allen, Jennifer Rebecca et al., WO 2004/094382 or Lang, Kai et al., Journal of Organic Chemistry, 75 (19), 6.424-6.435; 2010 (Scheme 3):

[223] Lactams are common in organic chemistry and the methods for their production are well known. For example, see: Smith, M.B. in Science of Synthesis, (2005) 21,653.
[224] If the individual compounds cannot be prepared using the routes described above, they can be prepared by derivatizing other compounds of Formula (I) or through the usual modifications of the described synthetic routes.
[225] For example, in individual cases, certain compounds of Formula (I) can advantageously be prepared from other compounds of Formula (I) by derivatization, for example, by ester hydrolysis, amidation, esterification, cleavage of ether, olefin, reduction, oxidation and the like, or through the usual modifications of the described synthesis pathways.
[226] The reaction mixtures are processed in the usual way, for example, by mixing with water, separating the phases and, if appropriate, purifying the crude products by chromatography, for example, on alumina or on silica gel.
[227] The term “invertebrate pest”, as used herein, encompasses animal populations, such as arthropod pests, including insects and arachnids, as well as nematodes that can attack plants, thereby causing damage substances to the attacked plants, as well as the ectoparasites that can infest animals, especially warm-blooded animals, such as, for example, mammals or birds or other superior animals, such as reptiles, amphibians and fish, causing substantial damage infested animals.
[228] The compounds of Formula (I), according to the present invention, are suitable for the efficient control of arthropod pests, such as arachnids, myrtles and insects, as well as nematodes.
[229] The compounds of Formula (I) are especially suitable for combating, efficiently, the following pests: - insects of the order of lepidopterans (Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphaniamisalalis, grandchildren, Diaphaniaia nitidalis, grandiflora Evoulia bouliana, Feltia subterranean, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellc, Leopard, Keiferia, Keiferia, Keiferia , Lithocolletis blancardella, Lobesia botrana, Loxo stege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea, Phthorimaea operand , Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera; - beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Bluchtophausha Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diathema, stenicbrica, Ctenicis. Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lemma bilineata, Lema melanopus, Leptinotarsa melonisanisanisanisanisanisil, communist, Limonius , Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Vegetable phyllopertha, Phyllotreta nemorum, Phyllotreta striolata, Sitophiaaria, Popillia Japonica, for example, Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaomya, Chivora viciniana, Callipora , Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalacura, Culisitae, Culis quinacura, Culiseta , Delia antique, Delia co arctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophiius intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates sppt. , Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinhorya frit, Pegomya frit, Pegomya -bia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaus span. Tabanus similis, Tipula oleracea and Tipula paludosa-, - thrips (Thysanoptera), for example, Dichromothrips corbetti, Dichromothrips ssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, - termites (Isoptera), for example, Calotermes, flavis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus-, - cockroaches (Blattaria - Blattodeella, german, blattina, German, for example) , Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalise - bedbugs, aphids, grasshoppers, whiteflies, mealybugs, cicadas (Hemiptera), for example, Acrosternum hilare, Blissus leucopterus, Dyrystisatus, Cyrtopus Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gisypne, Aphis gypsy Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, persicae Brachycaudus, prunicola Brachycaudus, brassicae Brevicoryne, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, ribis Cryptomyzus, nordmannianae Dreyfusia, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani , Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Myopoly, persian, Myriazis, Persian, Myanzis lugens, Pemphigus bur sarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis malai, Sappaphis mali, Schizaphis auris, aurora, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., And Arilus critatus-, - ants, bees, wasps, hornets (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta laevigata Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmym barbhe, Phagonomyrmex barbath, Phagonomyrmex barbatus, Phagonomyrmex barbatus, spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Do lichovespula maculata, Wasp crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile-, - crickets, grasshoppers, locusts (Orthoptera), for example, Acheta domestica, Gryllotalpa gryllotalpa, Locusta migradora, Melanoplus bivittatus, Melanoplus mexurrus Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, italicus, Chraicharia angulifera, Kraussaria angulifera; - arachnids, such as arachnids (Acarina), for example, from the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus decoloratus, Boophilus decoloratus, Boophilus decoloratus, Boophilus decoloratus, Boophilus decoloratus, Boophilus decoloratus, Dermacentor eersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, rubicundus Ixodes scapularis Ixodes, holocyclus Ixodes, pacificus Ixodes, Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini, gallinae Dermanyssus, ovis Psoroptes, Rhipicephalus sanguineus, Rhipicephalus appendiculatus , Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp., Such as Aculus schlechtendali, Phyllocoptrata oleivora, and Eriophyes sheldonr, Tarsonemidae spp., Such as Phytonemus pallidus and Polyphagotarsonemus latuse, Tenpidae spp. such as Brevipalpus phoenicis Tetranychidae spp., such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratens, and Oligonychus pratens reclusa-, - the flies (Siphonaptera), for example, Ctenocephaiides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, - book moths, earwig, (Thysanura), for example, Lepisma saccharina and Thermobia domestica, - centipedes (Chilopoda), for example, Scutigera coleoptrata, - myriapods (Diplopoda), for example, Narceus spp. - lacraias (Dermaptera), for example, Forficula auricularia, - lice (Phthiraptera), for example, Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovise, Men , Menacanthus stramineus and Solenopotes capillatus. - collembola (springtails), for example, Onychiurus ssp.
[230] The compounds of Formula (I) are also suitable for the control of nematodes: parasitic nematodes such as root nodule nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne species, cyst-forming nematodes , Globodera rostochiensis and other species of Globodera; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other species of Heterodera; seed gall nematodes, Anguina- species, stem and leaf nematodes, Aphelenchoides- species, sting nematodes, Belonolaimus longicaudatus and other Belonolaimus' species, pine nematodes, Bursaphelenchus xilophilus and other species of Bursaphelenchus-, neurs ring, Criconema species, Criconemella species, Criconemoides species, Mesocriconema- species, stem and bulb nematodes Ditilenchus destructor, Ditilenchus dipsaci and other Ditilenchus species, borer nematodes, Dolichodorus- species, spiral nematodes, Heliocotilenchus multicinctus and other species of Helicotylenchus-, sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides' species, Hirshmanniella species; sandeel nematodes, Hoploaimus species; false root node nematodes, Nacobbus species; needle nematodes, Longidorus elongates and other species of Longidorus; lesion nematodes, Pratilenchus neglectes, Pratilenchus penetrans, Pratilenchus curvitates, Pratilenchus goodeyi and other species of Pratilenchus; excavating nematodes, Radopholus similis and other species of Radopholus; reniform nematodes, Rotilenchus robustes and other species of Rotilenchus, species of Scutellonema; nematodes in the short and thick root, Tríchodorus prímitivuse other species of Tríchodorus, species of Paratrichodorus; inhibited nematodes, Tilenchorhynchus claytoni, Tilenchorhynchus dubius and other species of Tylenchorhynchus; citrus nematodes; Tilenchulus species, stylus nematodes, Xiphinema species; and other species of plant parasitic nematodes.
[231] The compounds of Formula (I) are especially useful for the control, or combat, or treatment, or prevention or protection of each individual group of target pests as listed above, as well as each of their combinations.
[232] Each of the groups or subgroups of the pests listed above, consists per se, independently of all possible combinations of a particular preferred target pest for which the compounds of the present invention are useful and, therefore, the special embodiment. Useful in this context should be understood as: - the use to combat such pest (s) or, - the use to control such pest (s) or, - the use to protect against pests attacks from such pests (s) or, - use for treatment against infestation or infection by such pests (s) or, - use for control against infestation or infection by such ( (a) pests (s) or, - use for the prevention of infestation or portal infection (s) pests (s) or, - use for the protection against infection or infestation by such pests (s) .
[233] The compounds of Formula (I) are especially useful for insect control, preferably sucking and perforating insects, such as insects of the genera Thysanoptera, Diptera and Hemiptera.
[234] The compounds of Formula (I) are especially useful for the control of insects of the order Hemiptera and Thysanoptera.
[235] For use in a method according to the present invention, compounds of Formula (I) can be converted into the usual formulations, for example, solutions, emulsions, suspensions, dust, powders, pastes, granules and solutions directly sprayable. The form of use depends on the purpose and method of application. The formulation and application methods are selected, in each case, to ensure a fine and uniform distribution of the compound of Formula (I), according to the present invention.
[236] The agrochemical composition according to the present invention comprises a pesticide-effective amount of a compound of Formula (I) according to the present invention. The term "effective amount" means an amount of the Formula (I) composition or compounds, which is sufficient for the control of animal pests in a location, such as crops, cultivated vegetables or in the protection of materials, and which does not result substantial damage to the treated vegetables. This amount can vary over a wide range and depends on several factors, such as the species of animal pests to be controlled, the plant grown or the material treated, the climatic conditions and the specific compound of Formula (I) used.
[237] The compounds of Formula (I), according to the present invention, can be converted into usual types of agrochemical compositions, for example, solutions, emulsions, suspensions, dust, powders, pastes, granules, presses, capsules, and their mixtures. Examples of types of composition are suspensions (for example, SC, OD, FS), emulsifiable concentrates (for example, EC), emulsions (for example, EW, EO, ES, ME), capsules (for example, CS, ZC), pastes, wafers, dusts or wettable powders (for example, WP, SP, WS, DP, DS), pressed (for example, BR, TB, DT), granules (for example, WG, SG, GR, FG , GG, MG), insecticidal articles (for example, LN), as well as gel formulations for the treatment of plant propagation materials, such as seeds (GF). These and other types of compositions are defined in the “Catalog of pesticide formulation types and international coding system”, Technical Monograph n ° 2, 6aed. May 2008, CropLife International.
[238] The compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
[239] Examples of suitable auxiliaries for formulations and / or agrochemical compositions according to the present invention are solvents, liquid vehicles, solid vehicles or excipients, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, promoters penetrating agents, protective colloids, adhesives, thickeners, humectants, repellents, attractions, food stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, adhesives and binders.
[240] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions, for example kerosene or diesel oil; oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example, toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, such as methanol, ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example, cyclohexanone; esters, for example, lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example, N-methylpyrrolidone, fatty acid dimethylamides, and mixtures thereof.
[241] Suitable solid vehicles or excipients are earthy minerals, such as silicates, silica gels, talc, kaolin, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate and magnesium sulfate, magnesium oxide; polysaccharides, for example, cellulose, starch; fertilizers, for example, ammonium sulphate, ammonium phosphate and ammonium nitrate, ureas; vegetable products, such as cereal flour, tree bark flour, wood flour, nutshell flour, and mixtures thereof.
[242] Suitable surfactants are surfactant compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration promoter, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon, Vol.1: Emulsifiers & Detergents, McCutcheon's Directors, Glen Rock, USA, 2008 (International Edition or North American Edition).
[243] Suitable anionic surfactants are the alkaline, alkaline earth or ammonium salts of the sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulphonates are alkylarylsulphonates, diphenylsulphonates, alpha-olefin sulphonates, lignin sulphonates, fatty acid sulphonates and oils, ethoxylated alkylphenol sulphonates, alkoxylated arylphenol sulphonates, condensed naphthalene sulphonates, sulphonates and sulphide sulphides naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinates. Examples of sulfates are fatty acid sulfates and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.
[244] Suitable non-ionic surfactants are alkoxylated, N-substituted fatty acid amides, amine oxides, sugar-based esters or surfactants, polymeric surfactants and their mixtures. Examples of alkoxylates are compounds, such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with from 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid starches are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are vinylpyrrolidone homo- or copolymers, vinylalcohols or vinylacetate.
[245] Examples of suitable cationic surfactants are quaternary surfactants, for example, quaternary ammonium compounds with one or two hydrophobic groups, or salts of long chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are block polymers of type A-B or A-B-A comprising the blocks of polyethylene oxide and polypropylene oxide or type A-B-C comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are the alkaline salts of polyacrylic acid. Examples of polybases are polyvinylamines or polyethyleneamines.
[246] Suitable adjuvants are compounds, which have negligible pesticidal activity or even no pesticidal activity, and which enhance the biological performance of the Formula (I) compound on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Other examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T & F Informa UK, 2006, chapter 5.
[247] Suitable thickeners are polysaccharides (for example, xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or not), polycarboxylates, and silicates.
[248] Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.
[249] Suitable antifreeze agents are ethylene glycol, propylene glycol, glycerin and urea.
[250] Suitable defoaming agents are silicones, long-chain alcohols and fatty acid salts.
[251] Suitable dyes are pigments (eg red, blue or green) with low water solubility and water-soluble dyes. Examples are inorganic dyes (for example, iron oxide, titanium oxide, iron hexacyanoferrate) and organic dyes (for example, alizarin-, azo- and phthalocyanine dyes).
[252] Suitable adhesives or binders are polyvinylpyrrolidones, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
[253] Examples of types of composition and their preparation are as follows: (I) HYDRO SOLUBLE CONCENTRATES (SL, LS) - From 10 to 60% by weight a compound of Formula (I), according to the present invention, and from 5 to 15% by weight of wetting agent (for example, alcohol alkoxylates) are dissolved in water and / or in a water-soluble solvent (for example, alcohols) up to 100% by weight. The active substance dissolves after dilution with water. (II) DISPERSIBLE CONCENTRATES (PC) - From 5 to 25% by weight of a compound of Formula (I), according to the present invention, and from 1 to 10% by weight of dispersant (for example, polyvinylpyrrolidone) are dissolved in up to 100% by weight of organic solvent (eg cyclohexanone). Dilution in water provides a dispersion. (In) EMULSIONABLE CONCENTRATES (EC) - From 15 to 70% by weight of a compound of Formula (I), according to the present invention, and from 5 to 10% by weight of emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (for example, aromatic hydrocarbons) at 100% by weight. Dilution in water provides an emulsion. (Iv) EMULSIONS (EW, EO, ES) - From 5 to 40% by weight of a compound of Formula (I), according to the present invention, and from 1 to 10% by weight of emulsifiers (for example, dodecylbenzenesulfonate calcium and castor oil ethoxylate) are dissolved in 20 to 40% by weight of non-water-soluble organic solvent (for example, aromatic hydrocarbons). This mixture is introduced in up to 100% by weight of water by means of an emulsifying machine and in a homogeneous emulsion. Dilution in water provides an emulsion. (V) SUSPENSIONS (SC, OD, FS) - In an agitated ball mill, 20 to 60% by weight of a compound of Formula (I), according to the present invention, are crushed with the addition of 2 to 10% by weight of dispersants and wetting agents (eg sodium lignosulfonate and ethoxylated alcohol), 0.1 to 2% by weight of thickener (eg xanthan gum) and up to 100% by weight of water for provide a fine suspension of active substance. Dilution in water provides a stable suspension of the active substance. For the type FS composition, up to 40% by weight of the binder (eg polyvinyl alcohol) is added. (VI) WATER-DISPERSIBLE GRANULES AND WATER-SOLUBLE GRANULES (WG, SG) - From 50 to 80% by weight a compound of Formula (I), according to the present invention, is finely ground with the addition of up to 100% by weight dispersants and wetting agents (for example, sodium lignosulfonate and ethoxylated alcohols) and prepared in the form of water-dispersible or water-soluble granules, by means of technical devices (for example, extrusion, spray tower, fluidized bed). Dilution with water provides a stable dispersion or solution of the active substance. (VII) POWERS DISPERSIBLE IN WATER AND WATER-SOLUBLE POWDER (WP, SP, WS) - From 50 to 80% by weight, a compound of Formula (I), according to the present invention, is ground in a rotor mill with the addition of 1 to 5% by weight of dispersants (for example, sodium lignosulfonate), 1 to 3% by weight of wetting agents (for example, alcohol ethoxylate) and up to 100% by weight of solid vehicle, for example example, silica gel. Dilution with water provides a stable dispersion or solution of the active substance. (Saw) GEL (GW, GF) - In a stirred ball mill, 5 to 25% by weight of a compound of Formula (I), according to the present invention, are crushed with the addition of 3 to 10% by weight of dispersants (for example, sodium lignosulfonate), from 1 to 5% by weight of thickener (for example, carboxymethylcellulose) and water up to 100% by weight, to provide a fine suspension of the active substance. Dilution with water provides a stable suspension of the active substance. (Ix) MICROEMULSION (ME) - From 5 to 20% by weight a compound of Formula (I), according to the present invention, is added to 5 to 30% by weight of the organic solvent mixture (for example, to fatty acid dimethylamide and cyclohexanone), from 10 to 25% by weight of the surfactant mixture (eg ethoxylated alcohol and ethoxylated arylphenol), and water up to 100%. This mixture is stirred for 1 hour to spontaneously produce a thermodynamically stable microemulsion. (X) MICROCapsules (CS) - An oil phase comprising from 5 to 50% by weight of a compound of Formula (I), according to the present invention, from 0 to 40% by weight of non-water-soluble organic solvent ( for example, aromatic hydrocarbons), from 2 to 15% by weight of acrylic monomers (for example, methyl methacrylate, methacrylic acid and a di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (for example, alcohol polyvinyl). The radical polymerization initiated through a radical initiator results in the formation of poly (meth) acrylate microcapsules. Alternatively, an oil phase comprising from 5 to 50% by weight of compound I, according to the present invention, from 0 to 40% by weight of non-water-soluble organic solvent (for example, aromatic hydrocarbons), and an isocyanate monomer (for example, diphenylmethen-4,4'-diisocyanatae) is dispersed in an aqueous solution of a protective colloid (for example, polyvinyl alcohol). The addition of a polyamine (for example, hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers is 1 to 10% by weight. The percentage (%) by weight refers to the total CS composition. (XI) DUSTY Powders (DP, DS) - From 1 to 10% by weight of a compound of Formula (I), according to the present invention, are finely crushed and intimately mixed with the solid carrier (for example, kaolin finely divided) to 100% by weight. (XII) GRANULES (GR, FG) - From 0.5 to 30% by weight of a compound of Formula (I), according to the present invention, are finely ground and associated with the solid vehicle (for example, silicate ) to 10% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed. (XIII) ULTRA LOW VOLUMES (UL) - From 1 to 50% by weight of a compound of Formula (I), according to the present invention, are dissolved in an organic solvent (for example, aromatic hydrocarbons) at 100 % by weight. The types of compositions from (i) to (xii) can optionally comprise other auxiliaries, such as from 0.1 to 1% by weight of bactericides, from 5 to 15% by weight of antifreeze agents, from 0.1 to 1% by weight of defoaming agents, and 0.1 to 1% by weight of colorants.
[254] Agrochemical compositions, in general, comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 0.5 and 75% by weight of the active substances, that is, the compounds of Formula (I) according to the present invention. The active substances are used in a purity of 90% to 100%, preferably from 95% to 100% (according to the NMR spectrum).
[255] Water-soluble concentrates (LS), suspoemulsions (SE), fluid concentrates (FS), treatment of dusty powders (DS), water-dispersible powders for sludge treatment (WS), water-soluble powders (SS), emulsions (ES ) emulsifiable concentrates (EC) and gels (GF), in general, are used for the purposes of treating plant propagation materials, especially seeds.
[256] The compositions in question, according to this invention, after being diluted by a factor of two to ten, provide the concentrations of the active substance from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in ready-to-use preparations.
[257] The application can be carried out before or during sowing. The methods for the application of the compound of Formula (I) and its compositions, respectively, in the propagation materials of the plants, especially the seeds include the methods of application by covering, coating, pelletizing, sprinkling, immersion and in the furrow of the propagation material . Preferably, the compound of Formula (I) or its compositions, respectively, is applied to the plant propagation material through a method in such a way that germination is not induced, for example, through the segment by covering, pelletizing, coating and sprinkling of seeds.
[258] When used to protect plants, the amounts of active substances used are, depending on the type of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, of greater preferably, from 0.005 to 0.9 kg per ha, and in particular, from 0.1 to 0.75 kg per ha.
[259] In the treatment of plant propagating material, such as seeds, for example, by sprinkling, coating or soaking the seeds, the amounts of the active substance from 0.1 to 1,000 g, preferably from 1 and 1,000 g, more preferably, from 1 to 100 g and even more preferably, from 5 and 100 g per 100 kg of plant propagation material (preferably seeds), in general, are needed.
[260] When used to protect stored materials or products, the amount of active substance applied depends on the type of application area and the desired effect. The amounts normally applied in protecting materials, for example, are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg of the active substance per cubic meter of the treated material.
[261] Various types of oils, wetters, adjuvants, fertilizers, or micronutrients and other pesticides (for example, herbicides, insecticides, fungicides, growth regulators, protective agents) can be added to the active substances, or to the compositions that comprise as a pre-mix or, if appropriate, not even immediately before use (tank mix). These agents can be mixed with the compositions according to the present invention in a weight ratio of 1: 100 to 100: 1, preferably from 1:10 to 10: 1.
[262] The user applies the composition, according to the process of the present invention, from a pre-dosing device, a backpack sprayer, a spray tank or an irrigation system. Usually, the agrochemical composition is made with water, buffer, and / or other auxiliary agents for the desired application concentration and the ready-to-use spray solution or agrochemical composition, according to the present invention, is therefore obtained . Normally, from 20 to 2,000 liters, preferably from 50 to 400 liters, of the spray solution ready for use are applied per hectare of the useful agricultural area.
[263] In accordance with an embodiment of the present invention, the individual components of the agrochemical composition, according to the present invention, such as parts of a set or parts of a binary or ternary mixture can be mixed by the user himself, in a spray tank and other auxiliaries can be added, if appropriate.
[264] In another embodiment, either individual components of the agrochemical composition according to the present invention, or partially premixed components, for example, comprising the components of the compounds of Formula (I) and, optionally, the substances Additional actives from groups M.1 to M.26, including MX or Fl to F.XII, can be mixed by the user in a spray tank and other auxiliaries and additives can be added, if appropriate.
[265] In another embodiment, the individual components of the composition according to the present invention, or the partially premixed components, for example, comprising the components of the compounds of Formula (I) and, optionally, the active substances Additional from groups M.1 to M.26, including MX or Fl to F.XII, can be applied together (for example, after tank mixing) or successively. MIXTURES
[266] The following M list of pesticides, grouped and numbered, according to the Insecticide Resistance Action Committee (IRAC) Classification Mode of Action, together with which the compounds according to the present invention can used and with which the potential synergistic effects can be produced, are intended to illustrate the possible combinations, but do not impose any limitations: - M.1: acetylcholine esterase inhibitors (AChE) from the - M.1A class : carbamates, for example, aldicarb, alanicarb, bendiocarb, benfuracarb, butocarboxy, butoxycarboxy, carbaryl, carbofuran, carbosulfan, etiofencarb, phenobucarb, formethanate, furatiocarb, isoprocarb, metiocarb, methoxy, tyrol, methanol, propyl, methanol, propyl, methoxy, methoxy, methoxy, methoxy, methoxy, propyl, methoxy, methoxy, propyl, thiofanox, trimetacarb, XMC, xylylcarb, triazamate; or from the class of - M.1B: organophosphates, for example, acephate, azametiphos, azinphos-ethyl, azinphos-methyl, cadusaphos, chlorethoxyphos, chlorfenvinfos, chlorephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton- S-methyl, diazinon, dichlorvós / DDPV, dichrotophos, dimetoate, dimethylvinphos, disulfotone, EPN, ethione, etoprofós, famfur, fenamiphos, fenitrothione, fentiona, fostiazato, heptenofós, imiciafos, isofenoxide-phosphorus (salicyl), salic isopropyl, isoxathione, malationa, mecarbam, metamidophos, metidation, mevinfós, monocrotofós, naled, ometoate, oxidemeton-methyl, parationa, paration-methyl, fentoate, phorate, fosalone, fosmet, phosphamidone, close, pyrimiphosphosphos, prophenyl protiofós, piraclofós, pyridafentiona, quinalfós, sulfotep, tebupirinfós, temefós, terbufós, tetrachlorvinfós, thiometone, triazofós, triclorfon; vamidothione; - M.2: GABA-activated chlorine channel antagonists, such as: - M.2A: cyclodienic organochlorine compounds, such as branches, for example, endosulfan or chlordane, or - M2B: fiprols (phenylpyrazoles), such such as, for example, etiprol, fipronil, flufiprol, pirafluprol and pyriprol; - M.3: sodium channel modulators from the class of - M.3A: pyrethroids, for example, acrinatrin, alethrin, d-cis-trans alethrin, d-trans alethrin, bifenthrin, bioalethrin, bioalectrin S -cilclopentenyl, bioresmethrin, cycloprotrine, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, teta-cypermethrin, zeta-cypermethrin, etherprenetrotin, emphytamine, emyrine , fenpropatrin, fenvalerate, flucitrinate, flumetrin, taufluvalinate, halfenprox, heptaflutrin, imiprotrine, meperflutrin, metoflutrin, permethrin, phenothrin, pralethrin, pyrethrin, pyrethrin, tetramethrine, tetrofluorethylene, tetrofluorethylene, tetrofluorethylene, tetrafluetamine, or - M.3B: sodium channel modulators, such as DDT or methoxychlorine; - M.4: nicotinic acetylcholine receptor (nAChR) agonists from the - M.4A class: neonicotinoids, for example, acetamipride, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpiram, thiaclopride and thiamethoxam, or compounds M.4A.2: (2E -) - 1 - [(6-chloropyridin-3-yl) methyl] -N-nitro-2-pentylidenoidrazincarboximidamide; or - M4.A.3: 1 - [(6-chloropyridin-3-yl) methyl] -7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexaidroimidazo [1 , 2-a] pyridine; - or from class M.4B: nicotine; - M.5: allotic nicotinic acetylcholine receptor activators from the class of spinosyns, for example, espinosad or espinetorama; - M.6: chlorine channel activators from the avermectin class and milbemycins, for example, abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin; - M.7: juvenile hormone simulators, such as - M.7A: juvenile hormone analogs, such as hydroprene, quinoprene and methoprene, or others such as M.7B: phenoxycarb or M.7C: pyriproxyphene ; - M.8: several non-specific inhibitors (multilocation), for example, - M.8A: alkyl halides, such as methyl bromide and other alkyl halides, or - M.8.B: chloropicrine or M .8C: sulfuryl fluoride, or M.8D: borax, or M.8E: emetic tartar; example, - M.9B: pimetrozine, or M.9C: flonicamide; - M.10: mite growth inhibitors, for example, - M.10A: clofentezine, hexitiazox and diflovidazin, or M.10B: ethoxazole; - M.11: the microbial disruptors of the intestinal membranes of insects, for example, Bacillus thuringiensis or Bacillus sphaericus, and the inset proteins they produce, such as Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki and Bacillus thuringiensis subsp. tenebrionis or proteins from Bt cultures: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34 / 35Ab1; - M.12: mitochondrial ATP synthase inhibitors, for example, - M.12A: diafentiurone, or - M.12B: organostanic acaricides, such as azocyclotine, cyhexatin or fenbutatin oxide, or M.12C: o propargite, or M.12D: tetradifone; - M.13: decouplers of oxidative phosphorylation by interrupting the proton gradient, for example, chlorfenapira, DNOC or sulfluramide; - M.14: nicotinic acetylcholine receptor channel blockers (nAChR), for example, nereistoxin analogues, such as bensultap, cartap hydrochloride, thiocyclam or sodium thiosultap; - M.15: type 0 chitin biosynthesis inhibitors, such as benzoylureans, such as, for example, bistriflurone, chlorfluazurone, diflubenzurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, noviflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, triflumurone, trifluurone. - M.16: type 1 chitin biosynthesis inhibitors, such as, for example, buprofezin; - M.17: the feather exchange disruptors, Diptera, such as, for example, cyromazine; - M.18: Ecdyson receptor agonists, such as diacylhydrazines, for example, methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide; - M.19: Octopamin receptor agonists, such as, for example, amitraz; - M.20: mitochondrial inhibitors of complex III electron transport, for example, - - M.20A: hydramethylnone, or M.20B: acequinocyl, or M.20C: fluacripyrim; - M.21: mitochondrial complex I electron transport inhibitors, for example, - M.21 A: METI acaricides and insecticides, such as phenazaquin, fenpyroximate, pyrimidifen, pyridabem, tebufenepirad or tolfenpirad or M.21B: rotenone; - M.22: voltage-dependent sodium channel blockers, for example, - M.22A: indoxacarb, or M.22B: metaflumizone, or M.22B.1: 2- [2- (4-cyanophenyl ) -1- [3- (trifluoromethyl) phenyl] ethyliden] -N- [4- (difluoromethoxy) phenyl] - hydrazinecarboxamide or M.22B.2: N- (3-chloro-2-methylphenyl) -2 - [( 4-chlorophenyl) [4- [methyl (methylsulfonyl) amino] phenyl] methylen] -hydrazinecarboxamide; - M.23: acetyl-CoA carboxylase inhibitors, such as tetronic and tetramic acid derivatives, for example, spirodiclofen, spiromesifene or spirotetramato; - M.24: the mitochondrial electron transport inhibitors of the IV complex, for example - M.24A: phosphine, such as aluminum phosphide, calcium phosphide, phosphine phosphide or zinc phosphide, or M.24B : cyanide; - M.25: mitochondrial inhibitors of complex II electron transport, such as beta-ketonitrile derivatives, for example, cienopyrafen or ciflumetofen; - M.28: ryanodine-modulating receptors of the diamide class, such as, for example, flubendiamide, chloranthraniliprol (rinaxipira®), cyantraniliprol (ciazipira®), or the phthalamide compounds M.28.1: (R) - 3-chloro-N1- {2-methyl-4- [1,2,2,2-tetrafluor-1- (trifluoromethyl) ethyl] phenyl} -N2- (1-methyl-2-methylsulfonylethyl) phthalamide, and M. 28.2: (S) -3-chloro-N1- {2-methyl-4- [1,2,2,2-tetrafluor-1- (trifluoromethyl) ethyl] phenyl} -N2- (1-methyl-2-methylsulfonylethyl ) phthalamide, or the compound M.28.3: 3-bromo-N- {2-bromo-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl} -1- (3-chlorpyridin-2-yl) - 1 H-pyrazol-5-carboxamide (proposed ISO name: cyclaniliprol), or the compound - M.28.4: methyl-2- [3,5-dibromo-2 - ({[3-bromo-1 - (3-chlorpiridin -2-iI) - 1 H-pyrazol-5-yl] carbonyl} amino) benzoyl] -1,2-dimethylhydrazincarboxylate; or a compound selected from M.28.5a) to M.28.5I): M.28.5a): N- [4,6-dichloro-2 - [(diethyl-lambda-4-sulfaniliden) carbamoyl] -phenyl ] -2- (3-chloro-2-pyridyl) -5- (trifluoromethyl) pyrazole-3-carboxamide; - M.28.5b: N- [4-chloro-2 - [(diethyl-lambda-4-sulfanylidene) carbamoyl] - 6-methyl-phenyl] -2- (3-chloro-2-pyridyl) -5- ( trifluoromethyl) pyrazol-3-carboxamide; M.28.5c: N- [4-chloro-2 - [(di-2-propyl-lambda-4-sulfanylidene) carbamoyl] -6-methyl-phenyl] -2- (3-chloro-2-pyridyl) - 5- (trifluoromethyl) pyrazol-3-carboxamide; M.28.5d: N- [4,6-dichloro-2 - [(di-2-propyl-lambda-4-sulfaniliden) carbamoyl] -phenyl] -2- (3-chloro-2-pyridyl) -5- (trifluoromethyl) pyrazol-3-carboxamide; M.28.5e: N- [4,6-dichloro-2 - [(diethyl-lambda-4-sulfaniliden) carbamoyl] -phenyl] -2- (3-chloro-2-pyridyl) -5- (difluoromethyl) pyrazole Carboxamide; M.28.5Í: N- [4,6-dibromo-2 - [(di-2-propyl-lambda-4-sulfaniliden) carbamoyl] -phenyl] -2- (3-chloro-2-pyridyl) -5- (trifluoromethyl) pyrazol-3-carboxamide; M.28.5g: N- [4-chloro-2 - [(di-2-propyl-lambda-4-sulfanylidene) carbamoyl] -6-cyano-phenyl] -2- (3-chloro-2-pyridyl) - 5- (trifluoromethyl) pyrazol-3-carboxamide; M.28.5h: N- [4,6-dibromo-2 - [(diethyl-lambda-4-sulfaniliden) carbamoyl] -phenyl] -2- (3-chloro-2-pyridyl) -5- (trifluoromethyl) pyrazole Carboxamide; - M.28.5Í: N- [2- (5-amino-1,3,4-thiadiazol-2-yl) -4-chloro-6-methyl-phenyl] -5-bromo-2- (3-chloro -2-pyridyl) pyrazol-3-carboxamide; - M.28.5j: 3-chloro-1 - (3-chloro-2-pyridinyl) -N- [2,4-dichloro-6 - [[((1-cyano-1-methylethyl) amino] carbonyl] phenyl] -1 H-pyrazol-5-carboxamide; - M.28.5k: 3-bromo-N- [2,4-dichloro-6- (methylcarbamoyl) phenyl] -1- (3,5-dichloro-2-pyridyl) -1H-pyrazol-5-carboxamide; M.28.5I: N- [4-chloro-2 - [[(1,1-dimethylethyl) amino] carbonyl] -6-methylphenyl] -1- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -1H-pyrazol-5-carboxamide; - or a compound selected from M.28.6: N- (2-cyanopropan-2-yl) -N- (2,4-dimethylphenyl) -3-iodobenzene-1,2-dicarboxamide; or M.28.7: 3-chloro-N- (2-cyanopropan-2-yl) -N- (2,4-dimethylphenyl) -benzene-1,2-dicarboxamide; M.28.8a: 1- (3-chloro-2-pyridinyl) -N- [4-cyano-2-methyl-6- [(methylamino) carbonyl] phenyl] -3 - [[5- (trifluoromethyl) -2H -tetrazol-2-yl] methyl] -1H-pyrazol-5-carboxamide; or M.28.8b: 1- (3-chloro-2-pyridinyl) -N- [4-cyano-2-methyl-6- [(methylamino) carbonyl] phenyl] -3 - [[5- (trifluoromethyl) - 1 H-tetrazol-1-i] methyl I] -1 H-pyrazole-5-carboxamide; - M.UN. insecticidal active compounds in an unknown or uncertain way of action, such as, for example, aphidopyropene, afoxolaner, azadiractin, amidoflumet, benzoxide, biphenazate, bromopropylate, quinometionat, cryolite, dicofol, flufenerin, flometoquin, fluensulfone, fluensulfone, fluensulfone, fluensulfone, fluensulfone, fluensulfone methoxadiazone, piperonyl butoxide, piflubumide, pyridalyl, pyrifluquinazone, sulfoxaflor, thioxazafene, triflumezopyrim, or the compounds M.UN.3: 11- (4-chloro-2,6-dimethylphenyl) -12-hydroxy-1,4-dioxa -9- azadispiro [4.2.4.2] -tetradec-11-en-10-one, or compound II-MX4: 3- (4'-fluoro-2,4-dimethylbiphenyl-3-yl) -4-hydroxy- 8-oxa-1-azospiro [4,5] dec-3-en-2-one, or the compound - II-MX5: 1- [2-fluoro-4-methyl-5 - [(2,2, 2-trifluoroethyl) sulfinyl] phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine, or active ingredients based on Bacillus firmus (Votivo, 1-1,582), or a compound selected from from the group of M.UN.6, where the compound is selected from M.UN.6a) to M.UN.βk): - M.UN.βa: (E / Z) -N- [1 - [(6-chloro- 3-pyridiI) methyl] -2-pyridiiden] -2,2,2-trifluoro-acetamide; - M.UN.βb: (E / Z) -N- [1 - [(6-chloro-5-fluoro-3-pyridyl) methyl] -2-pyridiliden] - 2,2,2-trifluoro-acetamide; - M.UN.6c: (E / Z) -2,2,2-trifluoro-N- [1 - [(6-fluoro-3-pyridi) methyl] -2-pyridyliden] acetamide; - M.UN.6d: (E / Z) -N- [1 - [(6-bromo-3-pyridyl) methyl] -2-pyridyliden] -2,2,2-trifluoro-acetamide; - M.UN.βe: (E / Z) -N- [1- [1- (6-chloro-3-pyridyl) ethyl] -2-pyridyliden] -2,2,2-trifluoro-acetamide; M.UN.6Í: (E / Z) -N- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridyliden] -2,2-difluoro-acetamide; - M.UN.βg: (E / Z) -2-chloro-N- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridine] - 2,2-difluoro-acetamide; - M.UN.6h: (E / Z) -N- [1 - [(2-chloropyrimidine-5-yl) methyl] -2-pyridine] - 2,2,2-trifluoro-acetamide; M.UN.6Í: (E / Z) -N- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridine] - 2,2,3,3,3- pentafluoro-propanamide); - M.UN.6j: N- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridyliden] -2,2,2-trifluoro-thioacetamide or the compound - M.UN.βk: N - [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridiliden] -2,2,2-trifluoro- N-isopropyl-acetamidine - or the compounds - M.UN.8: 8-chloro- N- [2-chloro-5-methoxyphenyl) sulfonyl] -6-trifluoromethyl) -imidazo [1,2-a] pyridin-2-carboxamide; or - M.UN.9: 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4H-isoxazol-3-yl] - 2-methyl-N- (1 -oxothietan-3-yl ) benzamide; or - M.UN.10: 5- [3- [2,6-dichloro-4- (3,3-dichloroalyloxy) phenoxy] propoxy] -1 H-pyrazole; or a compound selected from the group M.UN.11, where the compound is selected from M.UN.11a to M.UN.11p: M.UN.11.a: 3- [benzoyl (methyl) amino] -N- [2-bromo-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethyl) phenyl] -2-fluoro-benzamide; M.UN.11.b: 3- (benzoylmethylamino) -N- [2-bromo-4- [1,2,2,3,3,3-hexafluoro-1- (trifluoromethyl) propyl] -6- (trifluoromethyl ) phenyl] -2-fluoro-benzamide; - M.UN.11 .c: 3- (benzoylmethylamino) -2-fluoro-N- [2-iodo-4- [1,2,2,2- tetrafluoro-1- (trifluoromethyl) ethyl] -6- ( trifluoromethyl) phenyl] -benzamide; M.UN.11.e: N- [3 - [[[2-bromo ^ - [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethyl) phenyl] amino] carbonyl ] -2-fluorophenyl] -4-fluoro-N-methyl-benzamide; - M.UN.11 .f: 4-fluoro-N- [2-fluoro-3 - [[[2-iodo-4- [1,2,2,2-tetrafluoro-1- ““ -MU ”, , »(Tπfluoromethyl) ethyl] -6- (tπfluoromethyl) phenyl] amino] carbonyl] phenyl] -3-pyridinecarboxamide; - M.UN.11.i: 4-cyano-N- [2-cyano-5 - [[2,6-dibromo-4- [1,2,2,3,3,3-hexafluoro-1- ( trifluoromethyl) propyl] phenyl] carbamoyl] phenyl] -2-methyl-benzamide; M.UN. ,, »d> Glo, o-4 ,,, 2,2l3,3lS-» SKa, uo, u -, - (, n, uu, u »» UI) p, op> l | fe »L] -2-πuo, o-“ “: N“ - M.UN.11.1: N- [5 - [[2-bromo-6-chloro-4- [2,2,2-trifluoro-1- hydroxy-1- (trifluoromethyl) ethyl] phenyl] carbamoyl] -2-cyano-phenyl] -4-cyano-2-methyl-benzamide; - M.UN.11 .m: N- [5 - [[2-bromo-6-chloro-4- [1,2,2,3,3,3-hexafluoro-1- (trifluoromethyl) propyl] phenyl] carbamoyl] -2-cyano-phenyl] -4-cyano-2-methyl-benzamide; - M.UN.11.n: 4-cyano-N- [2-cyano-5 - [[2,6-dichloro-4- [1,2,2,3,3,3-hexafluoro-1- ( trifluoromethyl) propyl] phenyl] carbamoyl] phenyl] -2-methyl-benzamide; M.UN.11.o: 4-cyano-N- [2-cyano-5 - [[2,6-dichloro-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl ] carbamoyl] phenyl] -2-methyl-benzamide; (trifluoromethyl) ethyl] phenyl] carbamoyl] -2-cyano-phenyl] -4-cyano-2-methyl-benzamide; - or a compound selected from the group of M.UN.12, where the compound is selected from M.UN.12a to M.UN.12m: - M.UN.12.a: 2- (1 , 3-dioxan-2-yl) -6- [2- (3-pyridinyl) -5-thiazolyl] -pyridine; M.UN.12.b: 2- [6- [2- (5-fluoro-3-pyridinyl) -5-thiazolyl] -2-pyridinyl] - pyrimidine; - M.UN.12.c: 2- [6- [2- (3-pyridinyl) -5-thiazolyl] -2-pyridinyl] -pyrimidine; M.UN.12.d: N-methylsulfonyl-6- [2- (3-pyridyl) thiazol-5-yl] pyridin-2-carboxamide M.UN.12.e: N-methylsulfonyl-6- [2- (3-pyridyl) thiazol-5-yl] pyridin-2-carboxamide M.UN.12.Í: N-ethyl-N- [4-methyl-2- (3-pyridyl) thiazol-5-yl] -3 -methylthio-propanamide - M.UN.12.g: N-methyl-N- [4-methyl-2- (3-pyridyl) thiazol-5-yl] -3-methylthiopropanamide - M.UN.12. h: N, 2-dimethyl-N- [4-methyl-2- (3-pyridyl) thiazol-5-yl] -3-methylthio-propanamide M.UN.12.Í: N-ethyl-2-methyl- N- [4-methyl-2- (3-pyridyl) thiazol-5-yl] -3-methylthio-propanamide M.UN.12.j: N- [4-chloro-2- (3-pyridyl) thiazole- 5-yl] -N-ethyl-2-methyl-3-methylthio-propanamide - M.UN.12.k: N- [4-chloro-2- (3-pyridyl) thiazol-5-yl] -N, 2-dimethyl-3-methylthiopropanamide - M.UN.12.1: N- [4-chloro-2- (3-pyridyl) thiazol-5-yl] -N-methyl-3-methylthiopropanamide M.UN. 12.m: N- [4-chloro-2- (3-pyridyl) thiazol-5-yl] -N-ethyl-3-methylthiopropanamide; or the compound trifluoropropylsulfonyl) acetonitrile; - or the compounds - M.UN.14a: 1 - [(6-chloro-3-pyridinyl) methyl] -1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8- nitro-imidazo [1,2-a] pyridine; or - M.UN.14b: 1 - [(6-chloropyridin-3-yl) methyl] -7-methyl-8-nitro-1,2,3,5,6,7-hexaidroimidazo [1,2-a ] pyridin -5-ol; or the compound - M.UN.15: 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (3,5-dichlorophenyl) -9-methyl-4-oxo-4H -pyrido [1,2-a] pyramid-n-1 -ium-2-olate.
[267] The commercially available group M compounds listed above can be found in The Pesticide Manual, 15th Edition, C.D.S. Tomlin, British Crop Protection Council (2011), among other publications.
[268] The neonicotinoid cycloxaprid is known from WO 2012/0069266 and WO 2011/06946, and the neonicotinoid compound M.4A.2 is sometimes also called Guadipir, it is known from WO 2013/003977 , and the neonicotinoid compound M.4A.3. (approved as paichongding in China) is known from WO 2010/069266. M.22B.1 analogous to metaflumizone is described in patent CN 10.171.577 and M.22B.2 analogous to patent CN 102.126.994. Phthalamides M.28.1 and M.28.2 are both known from WO 2007/101540. Anthranilamide M.28.3 has been described in publication WO 2005/077934. The hydrazide compound M.28.4 has been described in publication WO 2007/043677. Anthranilamides from M.28.5 a) to M.28.5 h) can be prepared as in publications WO 2007/006670, WO 2013/024009 and WO 2013/024010, the anthranilamide compound M.28.5Í) is described in publication WO 2011 / 085575, compound M.28.5j) in publication WO 2008/134969, compound M.28.5k) in US patent 2011 / 046.186 and compound M.28.5I) in publication WO 2012/034403. The diamide compounds M.28.6 and M.28.7 can be found in patent CN 102,613,183. The anthranilamide compounds M.28.8a) and M.28.8b) are known from WO 2010/069502.
[269] The quinoline derivative of flometoquine is shown in publication WO 2006/013896. The aminofuranone compounds of flupiradifurone are known from WO 2007/115644. The sulfoxaflor sulfoximine compound is known from WO 2007/149134. Pyrethroid momfluorothrin is known from US patent 6,908,945 and heptaflutrin from publication WO 10133098. The oxadiazolone methoxyzazone compound can be found in JP 2013 / 166,707. Pyrazole acaricide piflubumide is known from WO 2007/020986. The isoxazoline compounds have been described in the following publications: the fluralaner in publication WO 2005/085216, the afoxolaner in publication WO 2009/002809 and in publication WO 2011/149749 and the isoxazoline compound M.UN.9 in publication WO 2013/050317 . The pyripiropene derivative afidopyropen has been described in WO 2006/129714. The thioxazafene nematicide has been described in publication WO 09023721 and the fluopyram nematicide in publication WO 2008/126922, the nematicidal mixtures comprising flupy in publication WO 2010/108616. The triflumezopyrim compound has been described in WO 2012/092115.
[270] The cyclic ketoenol derivative M.UN.3 replaced by spirocetal is known from publication WO 2006/089633 and the spirocyclic ketoenol derivative M.UN.4 replaced by biphenyl in publication WO 2008/067911. M.UN.5 triazoylphenylsulfide has been described in publication WO 2006/043635, and biological control agents based on Bacillus firmus in publication WO 2009/124707.
[271] The compounds of M.UN.6a) to M.UN.6Í) listed in M.UN.6 have been described in publication WO 2012/029672 and compounds M.UN.6j) and M.UN.6k) in publication WO 2013/129688. M.UN.8 composed of nematicides in publication WO 2013/055584 and M.UN.10 analog of pyridalyl-type in publication WO 2010/060379. The carboxamide compounds from M.UN.11.a) to M.UN.Hh) can be prepared as described in publication WO 2010/018714 and the carboxamide from M.UN.11Í) to M.UN.Hp) are described in WO 2010/127926. The pyridylthiazois of M.UN.12.a) to M.UN.12.C) are known from WO 2010/006713, M.UN.12.c) and M.UN.12.d) in the publication WO 2012/000896 and from M.UN.12.Í) to M.UN.12.m) in WO 2010/129497. The M.UN.13 malononitrile compound was described in WO 2009/005110. The compounds M.UN.14a) and M.UN.14b) are known from WO 2007/101369. The compound M.UN.15 can be found in publication WO 2013/192035.
[272] The following list F of fungicidal active substances, together with which the compounds according to the present invention can be used, is intended to illustrate the possible combinations, but not to limit: (Fl) BREATH INHIBITORS - (FI -1) Complex III inhibitors at the Qo site: strobilurins: azoxystrobin, coumetoxistrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, cresoxim-methyl, metominostrobin, orisastrobin, picoxystrobin, pyraclostrobin, pyracyclostrobin, pyracyclostrobin, pyracyclostrobin, pyracyclostrobin, pyracyclostrobin, pyracyclostrobin, pyracyclostrin, pyracyclostrin , 2- [2- (2,5-dimethyl-phenoxymethyl) -phenyl] -3-methoxy-acrylic acid methyl ester, and 2- (2- (3- (2,6-di-chlorophenyl) -1 -methyl-alliliden-aminooxy-methyl) -phenyl) -2-methoxyimino-N-methyl-acetamide; oxazolidinediones and imidazolinones: famoxadone, phenamidone; - (FI-2) Complex II inhibitors (for example, carboxamides): - carboxanilides: benodanil, benzovindiflupir, bixafen, boscalid, cartoxine, fenfuram, fenexamide, fluopiram, flutolanil, furametpir, isopirazam, isothyanyl, mepronil, mepronil , penflufen, pentiopirad, silkxane, keyboardoftalam, tifluzamide, thiadinyl, 2-amino-4 methyl-thiazol-5-carboxanilide, N- (3,, 4 ', 5'fluoromethylthiobiphenyl-2-yl) -3-difluoromethyl-1 - methyl-1 H-pyrazol-4-carboxamide (fluxpyroxad), N- (4'-trifluoromethyl Itiobifen i l-2-i I) -3-d if I uoromethi 1-1 -methyl-1 H-pyrazol- 4-carboxamide, N- (2- (1,3,3-trimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluor-1 H-pyrazol-4-carboxamide, 3- (difluoromethyl) -1 -methyl-N- (1,1,3-trimethyl-indan-4-yl) pyrazol-4-carboxamide, 3- (trifluoromethyl) -1-methyl-N- (1,1,3-trimethyl-indan-4 -yl) pyrazol-4-carboxamide, 1,3-dimethyl-N- (1,1,3-trimethylindan-4-yl) pyrazol-4-carboxamide, 3- (trifluoromethyl) -1,5-dimethyl-N- (1,1,3-trimethylindan-4-yl) -pyrazol-4-carboxamide, 3- (difluoromethyl)-1,5-dimethyl-N- (1,1,3-trimethylindan-4-yl) pyrazol-4-carboxamide, 1,3,5-trimethyl-N- (1,1,3-trimethylindan-4-yl) pyrazol-4-carboxamide, 3- (difluoromethyl) - 1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazol-4-carboxamide, 3- (trifluoromethyl) -1- methyl-N- (1,1,3-trimethylindan- 4-yl) pyrazol-4-carboxamide, 1,3-dimethyl-N- (1,1,3-yl) pyrazol-4-carboxamide; - (FI-3) Complex III inhibitors at the Qi site: [(3S, 6S, 7R, 8R) -8-benzyl-3 - [(3-acetoxy-4-methoxy-) cyanozofamide, amisulbroma, 2-methylpropanoate pyridine-2-carbonyl) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl], [(3S, 6S, 7R, 8R) -8-benzyl-2-methylpropanoate - [[3- (acetoxymethoxy) -4-methoxy-pyridine-2-carbonyl] amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl], [(3S 2-methylpropanoate , 6S, 7R, 8R) -8-benzyl-3 - [(3-isobutoxycarbonyloxy-4-methoxy-pyridin-2-carbonyl) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7 -il, [(3S, 6S, 7R, 8R) -8-benzyl-3 - [[3- (1,3-benzodioxol-5-ylmethoxy) - 4-methoxy-pyridin-2-carbonyl] 2-methylpropanoate amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl], 3S, 6S, 7R, 8R 2-methylpropanoate -3 - [[((3-hydroxy-4- methoxy-2-pyridinyl) carbonyl] amino] -6-methyl-4,9-dioxo-8- (phenylmethyl) -1,5-di-dioxonan-7-yl; - (F.I-4) Other respiration inhibitors (complex I uncouplers): diflumetorim; (5,8-difluoro-quinazolin-4-yl) - {2- [2-fluoro-4- (4-trifluoromethylpyridin-2-yloxy) -phenyl] -ethyl} -amine; technazene; ferimzone; ametoctradine; siltiofam; nitrophenyl derivatives: binapacril, dinobutone, dinocap, fluazinam, nitrtal-isopropyl, and including organometallic compounds: fentine salts, such as fentin acetate, fentin chloride, or fentin hydroxide; - (F.ll) Sterol biosynthesis inhibitors (SBI fungicides) - (F.II-1) C14 demethylase inhibitors (DMI fungicides, for example, triazole, imidazole) - triazoles: azaconazole, bitertanol, bromuconazole , cyproconazole, diphenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, miclobutanil, triclone, protonazole, protonazole, protonazole, protonazole , uniconazole, 1- [re / - (2S, 3 / ) - 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) -oxyranylmethyl] -5-thiocyanate-1 H- [1,2, 4] triazole, 2- [re / - (2S, 3 / ) - 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) -oxyranyl-methyl] -2H- [1,2,4] triazole-3-thiol; - imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole; - pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforin, 1 - [re / - (2S, 3 / ) - 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) - oxiranylmethyl] -5-thiocyanate-1 H- [1,2,4] triazole, 2- [rel- (2S, 3 / ) - 3- (2-chlorophenyl) -2- (2,4-difluorophenyl) -oxyranyl- methyl] -2H- [1,2,4] triazole-3-thiol; - (F.II-2) Delta 14 reductase inhibitors (amines, for example, morpholines, piperidines), morpholines: aldimorf, dodemorf, dodemorf acetate, fenpropimorf, tridemorf; - piperidines: phenpropidine, piperalin; spiroquetalamines: spiroxamine; - (F.II-3) 3-keto reductase inhibitors: hydroxyanilides: fenexamide; - (F.lll) Nucleic acid synthesis inhibitors - (F.111-1) RNA, DNA topisomerase inhibitors - the acyl amino acid phenylamides or fungicides selected from benalaxyl, benalaxyl-M, ciralaxil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixil; - isoxazoles and iosothiazolones: himexazole, octyline; - (F.III-2) DNA topisomerase inhibitors: oxolinic acid; - (F.III-3) Inhibitors of nucleotide metabolism (for example, adenosine deaminase), hydroxy- (2-amino) -pyrimidines: bupirimate; - (F.IV) Inhibitors of cell division and or cytoskeleton - (F.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl; - triazolopyrimidines: 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorphenyl) - [1,2,4] triazole [1,5-a] pyrimidine - (F.IV-2) Other cell division inhibitors: benzamides and phenyl acetamides: dietofencarb, etaboxam, pencicurone, fluopicolide, zoxamide; - (F.IV-3) actin inhibitors: benzophenones: metrafenone, pyriophenone; - (F.V) Inhibitors of the synthesis of amino acids and proteins - (F.V-1) Inhibitors of the synthesis of methionine (anilino-pyrimidines) - the anilino-pyrimidines: cyprodinil, mepanipirim, nitrapirin, pyrimethanil; - (F.V-2) Protein synthesis inhibitors (anilino-pyrimidines) - antibiotics: blasticidin-S, casugamycin, casugamycin hydrochloride, mildiomycin, streptomycin, oxytetracycline, polyoxin, validamycin A; - (F.VI) Signal transduction inhibitors - (F.VI-1) MAP / histidine kinase inhibitors (eg anilino-pyrimidines): dicarboximides: fluoroimide, iprodione, procymidone, vinclozoline; - phenylpyrroles: fenpiclonil, fludioxonil; - (F.VI-2) Protein G inhibitors: quinolines: quinoxyphene; - (F.VII) Inhibitors of lipid and membrane synthesis - (F. VI1-1) Inhibitors of phospholipid biosynthesis, organophosphate compounds: edifenfos, iprobenfos, pyrazophos; dithiolans: isoprothiolan; - (F.VII-2) Lipid peroxidation: aromatic hydrocarbons: dichloran, quintozena, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole; - (F.VII-3) Carboxylic acid amides (CAA fungicides) - cinnamic or mandelic acid amides: dimetomorf, flumorf, mandiproamid, pirimorf; - valinamide carbamates: bentiavalicarb, iprovalicarb, pyribencarb, valifenalate and N- (1- (1- (4-cyano-phenyl) -ethanesulfonyl) -but-2-yl) acid ester; - (F.VII-4) Compounds that affect the permeability of the cell membrane and fatty acids and: 1 - [4- [4- [5- (2,6-d if I uorophen i I) -4,5- dihydro-3-isoxazol yl] -2-thiazol i I] -1 - piperidinyl] -2- [5-methyl-3- (trifluoromethyl) -1 H-pyrazol-1-yl] ethanone, carbamates: propamocarb , propamocarb hydrochloride; - (F.VII-5) Fatty acid amide hydrolase inhibitors: 1- [4- [4- [5- (2,6-difluorophenyl) -4,5-dihydro-3-isoxazolyl] -2-thiazolyl ] -1-piperidinyl] -2- [5-methyl-3- (trifluoromethyl) -1 H-pyrazol-1-yl] ethanone; - (F.VI11) Multilocalized Inhibitors - (F.VIII-1) Inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; - (F.VIII-2) Uncle and dithiocarbamates: ferbam, mancozeb, maneb, metam, metasulfocarb, metiram, propineb, tiram, zineb, ziram; - (F.VIII-3) Organochlorine compounds (eg phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanide, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenol and its salts, phthalide, tolalide, tolalide, tolalide, tolalide N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide; - (F.VIII-4) Guanidinase other guanidines, dodine, dodine-free base, guazatin, guazatin acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesylate), dithianone, 2,6-dimethyl-1H, 5H- [1.4] ditiin [2,3-c: 5,6-c '] dipyrrol-1,3,5,7 (2H, 6H) -tetraone; - (F.VIII-5) Anthraquinones: dithianone; - (F.IX) Inhibitors of cell wall synthesis - (F.IX-1) Inhibitors of glucan synthesis: validamycin, polyoxin B; - (F.IX-2) Melanin synthesis inhibitors selected from piroquilon, triciclazole, carpropamide, diciclomet, fenoxanil; - (F.X) Vegetable defense inducers - (FX-1) Salicylic acid pathway: acibenzolar-S-methyl; - (FX-2) Others: probenazole, isothianyl, thiadinyl, calcium proexadione; phosphonates: fosetil, fosetil-aluminum, phosphoric acid and its salts; - (F.XI) Unknown mode of action: bronopol, quinomethionate, cyflufenamide, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat methylsulfate, diphenylamine, phenpyrazamine, flumetover, flusulfamide, flutianyl, metasulfocarb, nitropyrine, nitrapirine, nitrate oxatiapiproline, oxintin, proquinazide, tebufloquin, keyboardophthalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one, N- (cyclopropylmethoxyimino- (6-difluoro-methoxy-2,3-difluoro-phenyl) methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methyl, N-' formamidine (4- (4-fluoro-3-trifluoro-methyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methyl, N '- (2-methyl-5-trifluoromethyl-4- (3- trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methyl, N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methyl 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin (1,2,3,4-tetrahydro-naphthalen-1-yl) -amide -4-il} methyl-t iazol-4-carboxylic acid, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazole-1-1,2,3,4-tetrahydro-naphthalen-1-yl-amide-1- (2-) il) -acetyl] -piperidin-4-yl} methyl-thiazol-4-carboxylic acid, 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl methoxy-acetic acid and N -Methyl-2- {1 - [(5-methyl-3-trifluoro-methyl-1 H-pyrazol-1 -i I) -acety l] -pi peridi n-4-yl} -N - [(1 R) -1,2,3,4-tetrahydronaphthalen-1-yl] - 4-thiazolcarboxamide, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin- S-allyl ester 3-yl] -pyridine, pyrisoxazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazol-1-carbothioic S-allyl ester, cyclopropanecarboxylic acid amide N- (6-methoxy-pyridin-3-yl), 5-chloro-1 - (4,6-dimethoxy-pyrimidin-2-yl) -2-methyl-1H-benzimidazole, 2- (4-chloro-phenyl ) -N- [4- (3,4-dimethoxy-phenyl) - isoxazol-5-yl] -2-prop-2-inyloxy-acetamide, - (F.XII) Growth regulators: - abscisic acid, amidochlor , ancimidol, 6-benzylaminopurine, brassinolide, butralin, clormequat (clormequat chloride), choline chloride, cyclanilide, daminozide, diquegulac, dimethypine, 2,6-dimethylpuridine, etherone, flumetraline, flurprimidol, fluthiacet, forclorfenurone, gibberellic acid, inabenfide, indole-3-acetic acid, maléhydide, meiquid, meiquidide ), naphthalene acetic acid, N-6-benzyladenine, paclobutrazol, proexadione (calcium proexadione), proidrojasmon, tidiazuron, triapentenol, tributylphosphorotritioate, 2,3,5-triiodo-benzoic acid, trinexapac-ethyl and uniconazole; - (F.XII) biological control agents - Ampelomyces quisqualis (eg AQ 10® by Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (eg AFLAGUARD® by Syngenta, CH), Aureobasidium pullulans (by example, BOTECTOR® by bioferm GmbH, Germany), Bacillus pumilus (for example, NRRL accession number B-30087 in SONATA® and BALLAD® Plus by AgraQuest Inc., United States), Bacillus subtilis (for example, isolated NRRL number B-21661 in Rhapsody®, Serenade® Max and Serenade® ASO by AgraQuest Inc., United States), Bacillus subtilis var. amyloliquefaciens FZB24 (for example, Taegro® by Novozyme Biologicals, Inc., United States), Candida oleophila I-82 (for example, Aspire® by Ecogen Inc., United States), Candida saitoana (for example, BIOCURE® (in mixture with lysozyme) and Biocoat® from Micro Flo Company, United States (BASF SE) and Arysta), chitosan (e.g., ARMOR-ZEN by BotriZen Ltd., NZ), Clonostachys rosea f. catenulata, also called Gliocladium catenulatum (for example, J1446 isolated: Prestop® from Verdera, Finland), Coniothyrium minitans (for example, Contans® of Prophyta, Germany), Cryphonectria parasitica (for example, Endothia parasitica from CNICM, France), Cryptococcus albidus (for example, Yield Plus® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (for example, BIOFOX® from SIAPA, Italy, Fusacean® from Natural Plant Protection, France), Metschnikowia fructicola (for example, Shemer® Agrogreen, Israel), Microdochium dimerum (for example, Antibot® from Agrauxine, France), Phlebiopsis gigantea (for example, Rotsop® from Verdera, Finland), Pseudozyma flocculosa (for example, Sporodex® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (for example, Polyversum® by Remeslo SSRO, Biopreparaty, Czech Republic), Reynoutria sachlinensis (for example, Regalia® by Marrone BioInnovations, United States), Talaromyces flavus V117b (for example, Protus® by Prophyta,Germany), Trichoderma asperellum SKT-1 (for example, Ecohope® by Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (for example, Sentinel® by Agrimm Technologies Ltd, NZ), T. harzianumT-22 (for example, Plantshield® der Firma BioWorks Inc., United States), T. harzianum TH 35 (for example, Root Pro® of Mycontrol Ltd., Israel), T. harzianum T-39 (for example, Trichodex® and Trichoderma 2000® by Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T.harzianum and T. viride (for example, Trichopel from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (for example, Remedier ® WP from Isagro Ricerca, Italy), T. polysporum and T. harzianum (for example, BINAB® from BINAB Bio-Innovation AB, Sweden), T. stromaticum (for example, Tricovab® from CEPLAC, Brazil), T. virens GL-21 (for example, Soilgard® by Certis LLC, United States), T. viride (for example, Trieco® by Ecosense Labs. (India) Pvt. Ltd., India, Bio-Cure® F by T. Stanes & Co. Ltd., India), T. vinde TV1 (e.g., T. viride TV1 from Agribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g., Botry-Zen® by Botry-Zen Ltd, NZ).
[273] Animal pests, that is, insects, arachnids and nematodes, the vegetable, water or soil in which the vegetable grows, may come into contact with the present compounds of Formula (I) or composition (s) that contain by any application method known in the prior art. In this way, the term "contact" includes direct contact (application of compounds / compositions directly to animal or plant pests) and indirect contact (applying compounds / compositions to the site of the animal or plant pest).
[274] The compounds of Formula (I) or the pesticidal compositions containing them can be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, arachnids or mites or through contact of the plant / culture with a pesticide-effective amount of the compounds of Formula (I). The term "culture" refers to cultivation and harvesting.
[275] The compounds of the present invention and the compositions containing them are especially important for the control of a wide variety of insects in various cultivated vegetables, such as cereals, tubers, oil crops, vegetables, spices, ornamental vegetables, for example , durum wheat seeds and other wheat, barley, oats, rye, maize (fodder maize and sugar / sweet corn and field maize), soybeans, oilseeds, cruciferous, cotton, sunflower, bananas, rice, oilseeds rapeseed, wild turnip, fodder beet, eggplants, potatoes, grass, lawn, pasture, fodder grass, tomatoes, leek, pumpkin / strawberry, cabbage, lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onion, carrot, tuberous vegetables such as potatoes, sugar cane, tobacco, grapes, petunias, geranium / pelargonium, perfect loves and don't touch me.
[276] The compounds of the present invention are used as such or in the form of compositions through the treatment of insects or vegetables, plant propagating materials, such as seeds, soils, surfaces, materials or places to be protected from insecticidal attack. with an insecticidal effective amount of the compound of Formula (I). The application can be carried out before or after the infection of insects in plants, propagation materials of the plant, such as seeds, soils, surfaces, materials or places.
[277] The present invention also includes a method for combating animal pests that comprises the contact of animal pests, their habitat, breeding ground, food source, plant, seed, soil, areas, material or environment in which the pests animals grow or can grow, or the materials, vegetables, seeds, soils, surfaces or spaces to be protected from attack or infestation by animals, with an insecticide effective amount of at least one compound of Formula (I). In addition, animal pests can be controlled by contacting the target pest, its food source, habitat, breeding ground or its location with a pesticide-effective amount of the Formula (I) compounds. In this way, application can be carried out before or after infection of the sites, cultivation of crops, or harvesting by the pest.
[278] The compounds of the present invention can also be applied preventively to the places where the occurrence of pests is expected.
[279] The Formula (I) compounds can also be used for the protection of growing plants from attack or pest infestation by contacting the plant with a pesticide-effective amount of the Formula (I) compounds. Thus, the term "contact" includes direct contact (application of compounds / compositions directly on pests and / or the plant - usually on the foliage, stem or roots of the plant), and indirect contact (application of compounds / compositions to the location of the pest and / or plant).
[280] The term “local” means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or can grow.
[281] The term “plant propagating material” should be understood as designating all the generative parts of the plant, such as the seeds and material of the vegetative plant, such as grafts and tubers (for example, potatoes), which can be used for plant multiplication. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, sprouts, shoots and other parts of vegetables. Seedlings and young plants, which will be transplanted after germination, or after the emergence of the soil can also be included. These plant propagation materials can be treated prophylactically with a plant protection compound, before or during planting or transplantation.
[282] The term "cultivated vegetables" should be understood to include plants that have been modified by reproduction, mutagenesis or genetic engineering. Genetically modified vegetables are vegetables in which the genetic material has been modified in this way through the use of recombinant DNA techniques, which in natural circumstances cannot be obtained by cross-breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant, to improve certain properties of the plant. These genetic modifications include, but are not limited to, the targeted post-transitory modification of the protein (s), oligo- or polypeptides), for example, through glycosylation or addition of polymer such as the prenylated, acetylated or farnesylated moieties or portions of PEG (for example, as described in Biotechnol Prog. July-August 2001; 17 (4): 720-8, Protein Eng Des Sei.January 2004; 17 (1): 57-66, Nat Protoc. 2007 ; 2 (5): 1.225-35, Curr Opin Chem Biol, October 2006; 10 (5): 487-91. Epub August 28, 2006, Biomaterials, March 2001,22 (5): 405-17 , Bioconjug Chem. January-February 2005; 16 (1): 113-21).
[283] The term “cultivated vegetables” should also be understood, including vegetables that have been made tolerant to the application of certain classes of herbicides, such as hydroxyphenylpyruvate dioxigenase inhibitors (HPPD); acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see, for example, US patent 6,222,100, and publications WO 2001/82685, WO 2000/26390, WO 1997/41218, WO 1998/02526 , WO 1998/02527, WO 2004/106529, WO 2005/20673, WO 2003/14357, WO 2003/13225, WO 2003/14356, WO 2004/16073) or imidazolinones (see, for example, US patent 6,222. 100, and publications WO 2001/82685, WO 2000/26390, WO 1997/41218, WO 1998/02526, WO 1998/02527, WO 2004/106529, WO 2005/20673, WO 2003/14357, WO 2003/13225, WO 2003/14356, WO 2004/16073); the 3-phosphate-enolpyruvylshikimate synthase inhibitors (EPSPS), such as glyphosate (see, for example, publication WO 1992/00377); glutamine synthase (GS) inhibitors, such as glufosinate (see, for example, EP-A 242 236, EP-A 242 246) or oxynyl herbicides (see, for example, US patent 5,559,024 ) as a result of traditional methods of reproduction or genetic engineering. Several cultivated vegetables have been made tolerant to herbicides through traditional methods of reproduction (mutagenesis), for example, the Clearfield® summer rape (Canola) being tolerant to imidazolinones, for example, imazamox. Genetic engineering methods are used to make cultivated vegetables, such as soybeans, cotton, corn, beets and oilseed rape seed, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and Libertylink® (glufosinate).
[284] The term “cultivated vegetables” should also be understood to include vegetables that are, through the use of recombinant DNA techniques, capable of synthesizing one or more insecticidal proteins, especially those known from bacteria of the genus Bacillus, particularly the from Bacillus thuringiensis, such as δ-endotoxins, for example, CrylA (b), CrylA (c), CrilF, CrilF (a2), CrilIA (b), CrillIA, CrilllB (b1) or Cry9c; vegetative insecticidal proteins (VIP), for example, VIP1, VIP2, VIP3 or VIP3A; the insecticidal proteins of nematode colonizing bacteria, for example, Photorhabdus spp. or Xenorhabdus spp., toxins produced by animals, such as toxins, scorpion toxins, arachnid toxins or wasp toxins, or other insect-specific neurotoxins, fungal toxins such as Streptomycetes toxins, plant lectins , such as peas, barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribosome inactivation proteins (RIP), such as ricin, corn RIP, abrina, lufin, saporin or briodine, steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdiesteroid-IDP-glycosyl transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as sodium or calcium channel blockers; juvenile hormonal esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention, these insecticidal proteins or toxins are also expressly understood as pre-toxins, truncated or hybrid proteins, proteins modified in another way. Hybrid proteins are characterized by a new combination of protein domains, (see, for example, publication WO 2002/015701). Other examples of such toxins or genetically modified plants, capable of synthesizing such toxins, for example, are described in EP-A 374.753, WO 1993/007278, WO 1995/34656, EP-A 427.529, EP-A 451.878, WO 2003 / 18810 and WO 2003/52073. Methods for producing such genetically modified vegetables are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in genetically modified plants provide the plants that produce these proteins with protection against pests of certain taxonomic groups of arthropods, especially beetles (Coeloptera), flies (Diptera) and moths and moths (Lepidoptera) and parasitic nematodes of vegetables (Nematoda).
[285] The term “cultured vegetables” should also be understood to include vegetables that are, through the use of recombinant DNA techniques, capable of synthesizing one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral pathogens and fungal. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, for example, EP-A 392,225), genes for resistance to plant diseases (for example, potato cultivars, which express resistance genes that act against Phytophthora weeds derived from Mexican wild potato Solatium bulbocastanum) or T4-lysozyme (for example, cultivars capable of synthesizing these proteins, with increased resistance against bacteria, such as Erwinia amilvora ). Methods for producing such genetically modified vegetables are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
[286] The term “cultivated vegetables” should also be understood to include vegetables that are, through the use of recombinant DNA techniques, capable of synthesizing one or more proteins to increase productivity (for example, biomass production, productivity grain content, starch content, oil content, or protein content), tolerance to aridity, salinity or other environmental factors limiting growth or tolerance to pests and fungal, viral or bacterial pathogens of these vegetables.
[287] The term "cultivated vegetables" should also be understood to include vegetables that contain, through the use of recombinant DNA techniques, a quantity of substances of content or new substances of content, specifically to improve human or animal nutrition, for example, oil crops for the production of long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids that promote health (for example, Nexera® rapeseed).
[288] The term “cultivated vegetables” should also be understood to include vegetables that contain, through the use of recombinant DNA techniques, a quantity of substances of content or new substances of content, specifically to improve the production of the raw material, for example, potatoes that produce increased amounts of amylopectin (for example, Amflora® potatoes).
[289] In general, the term "pesticide-effective amount" means the necessary amount of active ingredient (at present, the compound of Formula (I)) to achieve an observable effect on growth, including the effects of necrosis, death, delay , prevention and removal, destruction, or otherwise reducing the occurrence and activity of the target organism. The amount effective as a pesticide can vary according to the different compounds / compositions used in the invention. A pesticide-effective amount of the compositions will also vary according to the prevailing conditions, such as the desired effect and duration of the pesticide, the time, the target species, the location, the manner of application, and the like.
[290] In the case of soil treatment or application for the pest in homes or nests, the amount of the active ingredient varies from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
[291] The usual application rates for protecting materials, for example, are from 0.01 g to 1,000 g of active compounds per m2 of the treated material, desirably from 0.1 g to 50 g per m2.
[292] Insecticidal compositions for use in impregnating materials normally contain from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight and, most preferably, from 1 to 25% by weight of at least one repellent and / or insecticide.
[293] For use in the treatment of cultivated vegetables, the application rate of the active ingredients of the present invention can be in the range from 0.1 g to 4000 g per hectare, preferably from 25 g to 600 g per hectare , most preferably, from 50 g to 500 g per hectare.
[294] The compounds of Formula (I) are effective through contact (via soil, glass, wall, mosquito net, carpet, parts of plants or parts of animals), and ingestion (bait, or part of the plant).
[295] The compounds of the present invention can also be used against non-agricultural insect pests, such as ants, termites, wasps, flies, mosquitoes, crickets, locusts or cockroaches. For use against said non-agricultural pests, the compounds of Formula (I) are preferably used in a bait composition.
[296] The bait can be a liquid, solid or semi-solid preparation (for example, a gel). Solid baits can be formed in various shapes and forms suitable for the respective application, for example, granules, tablets, sticks, discs. Liquid baits can be filled in various devices to ensure correct application, for example, open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated for particular needs in terms of adhesion, moisture retention or aging.
[297] The bait used in the composition is a product that is attractive enough to incite insects, such as ants, termites, wasps, flies, mosquitoes, crickets and similar or cheap to eat it. Attraction can be manipulated through the use of food stimulants or sexual pheromones. Food stimulants are selected, for example, but not exclusively, from proteins of animal and / or vegetable origin (from meat, fish or blood meal, insect parts, egg yolk), from fats and oils from animal and / or vegetable origin, or mono, oligo or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or molasses or honey. Fresh or decomposing parts of fruits, crops, vegetables, animals, insects or their specific parts can also serve as a food stimulant. Sexual pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
[298] For use in bait compositions, the typical content of the active ingredient is from 0.001% by weight to 15% by weight, desirably from 0.001% by weight to 5% by weight of the active ingredient in the ingredient harmful.
[299] Formulations of Formula (I) compounds such as aerosols (for example, in spray cans), pump sprayers or oil sprayers are highly suitable for the non-professional user for pest control, such as flies , fleas, ticks, mosquitoes or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, such as lower alcohols (for example, methanol, ethanol, propanol, butanol), ketones (for example, acetone, methyl ethyl ketone), hydrocarbons of paraffin (for example, kerosenes) that have boiling ranges of about 50 to 250 ° C, dimethylformamide, Nmethylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons, such as toluene, xylene, water, and auxiliary agents such as emulsifiers, such as sorbitol monooleate, oleyl ethoxylate which contains 3 to 7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils, such as essential oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if necessary, stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if necessary, propellants such as propane, butane, nitrogen , compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
[300] Oil spray formulations differ from aerosol recipes in which no propellant is used. For use in spray compositions, the content of the active ingredient is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight and, most preferably, from 0.01 to 15% by weight.
[301] The Formula (I) compound and its respective compositions can also be used in mosquito coils and fumigators, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other systems heat-independent vaporization
[302] The methods for controlling infectious diseases transmitted by insects (for example, malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with the compounds of Formula (I) and their respective compositions also include surface treatment huts and houses, aerial spraying and impregnation of curtains, tents, clothing items, mosquito nets, tsetse fly traps or similar. Insecticidal compositions for application to materials of fibers, fabrics, knits, nonwovens, mesh material or sheets and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents, for example, are N, N-diethyl-meta-toluamide (DEET), N, N-diethylphenylacetamidia (DEPA), 1- (3-cyclohexan-1-yl-carbonyl) -2-methylpiperine, lactone of acetic acid (2-hydroxymethylcyclohexyl), 2-ethyl-1,3-hexanediol, indalone, methylneodecanamide (MNDA), an unused pyrethroid for insect control, such as {(+/-) - 3-allyl-2 -methyl-4-oxocyclopent- 2 - (+) - enyl- (+) - trans-chrysantemate (sbiotrin), a repellent derived or identical to plant extracts, such as limonene, eugenol, (+) - eucamalol (1) , (-) - 1-epi- eucamalol or crude plant extracts of vegetables, such as Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemongrass), Cymopogan nartdus (citronella). Suitable binders are selected, for example, from the polymers and copolymers of vinyl esters of aliphatic acids (such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2 - ethylexyl and methyl acrylate, mono and diethylenically unsaturated hydrocarbons, such as styrene and aliphatic diens, such as butadiene.
[303] The impregnation of curtains and mosquito nets, in general, is carried out by immersing the textile material in the emulsions or dispersions of the insecticide or by spraying on the nets.
[304] The compound of Formula (I) and its compositions can be used for the protection of wood materials, such as trees, partition fences, beams, and the like and buildings such as houses, porches, factories, but also building materials, furniture, leather, fibers, vinyl articles, electric cables and wires, and the like of ants and / or termites, and for the control of ants and termites that cause damage to crops or to humans (for example, when pests invade public houses and facilities). The Formula (I) compounds are applied not only to the surrounding soil surface or to the soil under the floor, for the protection of wooden materials, but can also be applied to heavy articles such as concrete surfaces under the floor, poles alcove, beams, plywood, furniture, and the like, wooden articles, such as particulate panels, half panels, and the like and vinyl articles, such as coated electrical wires, vinyl plates, thermal insulating material, such such as styrene foams, and the like. In the case of application against ants that cause damage to crops or humans, the ant controller of the present invention is applied to crops or to the surrounding soil, or are applied directly to the ant's nest or the like.
[305] The compounds of Formula (I) are also suitable for the treatment of seeds, for the protection of the seed against insect pests, in particular, against the insect pests that live in the soil and the resulting plant roots and sprouts against soil pests and leaf insects.
[306] The compounds of Formula (I) are especially useful for protecting seeds against soil pests and resulting plant roots and sprouts against soil pests and leaf insects. Protection of the roots and shoots of the resulting plant is preferred. Most preferably, it is the protection of the roots and shoots of the resulting plant against sucking and perforating insects, in which protection against aphids is the most preferred.
[307] Therefore, the present invention comprises a method for the protection of seeds against insects, in particular, against soil insects and the roots and shoots of insect seedlings, in particular, against soil and leaf insects, said method comprises placing the seeds before sowing and / or after pre-germination, in contact with a compound of Formula (I) or a salt thereof. Especially preferred is a method, in which the roots and shoots of the vegetable are protected, more preferably, a method, in which the shoots of the vegetables are protected from sucking and perforating insects, more preferably, a method, in which the roots and the shoots of vegetables are protected against aphids.
[308] The term “seed” covers the seeds and propagules of vegetables of all types, which includes, but is not limited to, true seeds, parts of seeds, suckers, corms, bulbs, fruit, tubers, grains, grafts, graft shoots and the like and means, in a preferred embodiment, the true seeds.
[309] The term "seed treatment" includes all suitable seed treatment techniques known in the art, such as seed treatment, seed coating, seed sprinkling, seed immersion and seed pelleting.
[310] The present invention also comprises seeds coated with or containing the compound of Formula (I). The term "coated with and / or containing" generally means that the active ingredient is on most of the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate the propagation product, depending on application method. When said propagation product is (re) planted, it can absorb the active ingredient.
[311] Suitable seed is the seed of cereals, root crops, oil crops, vegetables, spices, ornamental vegetables, for example, durum wheat seeds and other wheat, barley, oats, rye, maize (forage maize and sugar corn / sweet and field corn), soybeans, oilseeds, cruciferous crops, cotton, sunflower, bananas, rice, oilseed rape seed, wild turnip, sugar beet, fodder beet, eggplants, potatoes, grass, lawn, grass, forage grass, tomatoes, leek, pumpkin / strawberry, cabbage, lettuce, pepper, cucumbers, melons, brassica species, melons, beans, peas, garlic, onion, carrot, tuberoses, such as potatoes, sugar cane, tobacco, grapes, petunias, geranium / pelargonium, perfect loves and don't touch me.
[312] In addition, the compound of Formula (I) can also be used for the treatment of vegetable seeds, which tolerate the action of herbicides or fungicides or insecticides due to animal reproduction, which includes genetic engineering methods.
[313] For example, the compound of Formula (I) can be used to treat vegetable seeds, which are resistant to herbicides from the group consisting of sulfonylureas, imidazolinones, glufosinate-ammonium, isopropylammonium glyphosate and analogous active substances (see, for example, EP-A.242.236, EP-A.242.246, publication WO 1992/00377, EP-A.257.993, US 5,013,659) or on transgenic crops, for example, cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) that make vegetables resistant to certain pests (EP-A 142,924, EP-A 193,259),
[314] In addition, the compound of Formula (I) can also be used for the treatment of vegetable seeds, which have modified characteristics in comparison with the existing vegetables consist, which can be generated, for example, through traditional methods of reproduction and / or generation of the mutants, or through recombinant procedures). For example, a number of cases of recombinant modifications of cultured vegetables have been described with the aim of modifying the starch synthesized in plants (for example, WO 1992/11376, WO 1992/14827, WO 1991/19806) or transgenic crop vegetables with a modified fatty acid composition (publication WO 1991/13972).
[315] The application of the seed treatment of the compound of Formula (I) is carried out by spraying or by spraying the seeds before sowing the vegetables and before the emergence of the vegetables.
[316] The compositions, which are especially useful for seed treatment, for example, are:

[317] Conventional seed treatment formulations include, for example, FS fluid concentrates, LS solutions, DS dry treatment powders, water dispersible powders for the treatment of WG syrup, SS water soluble powders and ES and EC emulsion. and the GF gel formulation. These formulations can be applied to the seed diluted or undiluted. The application to the seeds is carried out before sowing, directly on the seeds or after their pre-germination.
[318] In a preferred embodiment, an FS formulation is used for seed treatment. Normally, an SC formulation can comprise from 1 to 800 g / L of the active ingredient, 1 to 200 g / L of surfactants, from 0 to 200 g / L of antifreeze agent, from 0 to 400 g / L of binder, from 0 to 200 g / L of a pigment, and up to 1 liter of a solvent, preferably water.
[319] Especially preferred FS formulations of compounds of Formula (I) for seed treatment, in general, comprise from 0.1 to 80% by weight, (from 1 to 800 g / L), of the active ingredient , from 0.1 to 20% by weight (from 1 to 200 g / L) of at least one surfactant, for example from 0.05 to 5% by weight of a wetting agent and from 0, 5 to 15% by weight of a dispersing agent, up to 20% by weight, for example, from 5 to 20% of an antifreeze agent, from 0 to 15% by weight, for example, from 1 to 15 % by weight of a pigment and / or a dye, from 0 to 40% by weight, for example, from 1 to 40% by weight of a binder (adhesive / adhesion agent), optionally up to 5% by weight, for example, from 0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of a defoaming agent, and optionally a preservative, such as a biocide, antioxidant or the like, for example , in an amount from 0.01 to 1% by weight, and an excipient / vehicle up to 100% in weight Weight.
[320] Seed treatment formulations, in addition, can also comprise binders and, optionally, dyes.
[321] Binders can be added to improve the adhesion of active materials to seeds after treatment. Suitable binders are the alkylene oxide homo and copolymers, such as ethylene oxide or propylene oxide, polyvinyl acetate, polyvinyl alcohol, polyvinylpyrrolidones and their copolymers, ethylene-vinyl acetate copolymers, homo- and copolymers polyethyleneamines, polyethyleneamides and polyethyleneimines, polysaccharides such as celluloses, tilose and starch, homo and polyolefin copolymers such as anhydride olefin / maleic copolymers, homo and copolymers of polyurethanes, polyesters, polystyrene.
[322] Optionally, dyes can also be included in the formulation. The dyes or dyes suitable for seed treatment formulations are Rhodamin B, pigment C.l. red 112, solvent C.l. red 1, blue pigment 15: 4, blue pigment 15: 3, blue pigment 15: 2, blue pigment 15: 1, blue pigment 80, yellow pigment 1, yellow pigment 13, red pigment 112, red pigment 48: 2, pigment red 48: 1, red pigment 57: 1, red pigment 53: 1, orange pigment 43, orange pigment 34, orange pigment 5, green pigment 36, green pigment 7, white pigment 6, brown pigment 25, basic violet 10, violet basic 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
[323] Examples of a gelling agent are carrageenan (Satiagel®).
[324] In seed treatment, the application rates of the compounds of the present invention, in general, are from 0.1 g to 10 kg per 100 kg of seeds, preferably from 0.5 g to 5 kg per 100 kg of seed, most preferably from 1 g to 1,000 g per 100 kg of seeds and in particular from 1 g to 200 g per 100 kg of seeds.
[325] Accordingly, the present invention also relates to seeds that comprise a compound of Formula (I), or an agriculturally useful salt of I, as defined herein. The amount of the compound of Formula (I) or its agriculturally useful salt, in general, varies from 0.1 g to 10 kg per 100 kg of seeds, preferably from 1 g to 5 kg per 100 kg of seeds in particular, from 1 g to 1,000 g per 100 kg of seeds. For certain crops, such as lettuce, the rate may be higher.
[326] The compounds of Formula (I) or the enantiomers or their acceptable veterinary salts, in particular, are also suitable for use to combat pests in and on animals.
[327] Therefore, an object of the present invention is also to provide new methods for the control of parasites in and on animals. Another object of the present invention is to provide the safest pesticides for animals. Another object of the present invention is to provide animals with pesticides, which can be used in lower doses than existing pesticides. Another object of the present invention is to provide pesticides to animals, which provide long-term residual control of parasites.
[328] The present invention also relates to compositions that contain a parasiticidal effective amount of the compounds of Formula (I) or their enantiomers or their veterinarily acceptable salts, and an acceptable vehicle for combating pests in and on animals .
[329] The present invention also provides a method for the treatment, control, prevention and protection of animals against infestation and infection by parasites, comprising administering or applying orally, topically or parenterally to animals, an effective amount as a parasiticide of a compound of Formula (I) or its enantiomers or its veterinary acceptable salts or a composition comprising them.
[330] The present invention also provides a process for the preparation of a composition for the treatment, control, prevention and protection of animals against infestation or infection by parasites, which comprises a parasiticidal amount of a compound of Formula (I ) or its enantiomers or its veterinary acceptable salts or a composition comprising them.
[331] The activity of compounds against agricultural pests does not suggest their suitability for the control of endoparasites and ectoparasites in and in animals that require, for example, low non-emetic dosages, in the case of oral application, the animal's metabolic compatibility , low toxicity and safe handling.
[332] Surprisingly, it has been found that the compounds of Formula (I) are suitable for combating endoparasites and ectoparasites in and on animals.
[333] The compounds of Formula (I) or their enantiomers or their veterinary acceptable salts, and the compositions comprising them, are preferably used for the control and prevention of animal infestations and infections, including blood animals (including humans) and fish. They, for example, are suitable for the control and prevention of infestations and infections in mammals, such as cattle, sheep, pigs, camels, deer, horses, pigs, birds, rabbits, goats, dogs and cats, buffaloes, donkeys, deer and reindeer, and also in animals with skin such as mink, chinchilla and raccoon, birds such as chickens, geese, turkeys and ducks and fish such as freshwater and saltwater fish such as trout, carp and eels.
[334] The compounds of Formula (I) or their enantiomers or their veterinary acceptable salts, and the compositions comprising them, are preferably used for the control and prevention of infestations and infections of domestic animals, such as dogs or cats.
[335] Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nostrils, lice, biting flies, muscoid flies, flies, myiasitic fly larvae, larvae, mosquitoes, and mosquitoes fleas.
[336] The compounds of Formula (I) or the enantiomers or their veterinarily acceptable salts, and the compositions comprising them are suitable for the systemic and / or non-systemic control of ectoparasites and / or endoparasites. They are active against some or all stages of development.
[337] The compounds of Formula (I) are especially useful for combating ectoparasites.
[338] The compounds of Formula (I) are especially useful for combating parasites of the following orders and species (for example, as listed above above in target pests if not explicitly listed below), respectively: - fleas (Siphonaptera) ; - cockroaches (Blattaria - Blattodea); - flies, mosquitoes (Diptera); - lice (Phthiraptera); - ticks and parasitic mites (Parasitiformes) of arachnoidea; - Actinedida (Prostigmata) and Acaridida (Astigmata); - bedbugs (Heteropterida); - anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.] Mallophagida (Arnblycerina and Ischnocerina subordens), for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp, - Nematoda roundworms, for example, worms and trichinosis (Trichosyringida), for example, Trichinellidae (Trichinella spp.), (Trichurella sp. Trichurís spp., Capillaria spp - Rhabditida, for example, Rhabditis spp, Strongyloides spp., Helicephalobus spp, - Strongylida, for example, Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Anthurus dentatus, spp., Uncinaría spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale; - intestinal roundworms (Ascaridida), for example, Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi, - by Caxymall small, , Dracunculus medinensis (Guinea worm) - Spirurida, for example, Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp. ', - spiny-headed worms (Acanthocephala), for example, o Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp. - planarians (Platelmintas): - worms (Trematoda), for example, Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., And Nanocyetes spp, - Cercomeromorpha, in particular Cestoda (flatworms), for example, Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesym spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp. The compounds of Formula (I) and the compositions that comprise them are especially useful for pest control of the orders Diptera, Siphonaptera and Ixodida.
[339] In addition, the use of the compounds of Formula (I) and the compositions containing them to fight mosquitoes is especially preferred.
[340] The use of the compounds of Formula (I) and the compositions comprising them for combating flies is another preferred embodiment of the present invention.
[341] In addition, the use of the compounds of Formula (I) and the compositions comprising them for combating fleas are especially preferred.
[342] The use of the compounds of Formula (I) and the compositions comprising them for combating ticks is another preferred embodiment of the present invention.
[343] The Formula (I) compounds are also especially useful for combating endoparasites (Nematoda roundworms, spiny-headed and planar worms). [346] For oral administration in warm-blooded animals, the compounds of Formula (I) can be formulated as animal feed, animal feed pre-mixes, animal feed concentrates, tablets, solutions, pastes, suspensions, liquid medicines, gels, tablets, cakes and capsules. In addition, the compounds of Formula (I) can be administered to animals in their drinking water. For oral administration, the selected dosage form should provide the animal with 0.01 mg / kg to 100 mg / kg in body weight of the animal per day of the compound of Formula (I), preferably 0.5 mg / kg to 100 mg / kg of the animal's body weight per day.
[344] Administration can be carried out prophylactically or therapeutically.
[345] The administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically / parenterally, or dermally. The term "active component (s)", as used above, means that it comprises at least one compound of Formula (I) and, optionally, the additional active compound (s) ).
[346] For oral administration to warm-blooded animals, compounds of Formula (I) can be formulated as animal feed, animal feed pre-mixes, animal feed concentrates, tablets, solutions, pastes, suspensions, liquid medicines, gels, tablets, cakes and capsules. In addition, the compounds of Formula (I) can be administered to animals in their drinking water. For oral administration, the selected dosage form should provide the animal with 0.01 mg / kg to 100 mg / kg in body weight of the animal per day of the compound of Formula (I), preferably 0.5 mg / kg to 100 mg / kg of the animal's body weight per day.
[347] Alternatively, the compounds of Formula (I) can be administered to animals parenterally, for example, through intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of Formula (I) can be dispersed or dissolved in a physiologically acceptable vehicle through subcutaneous injection. Alternatively, the compounds of Formula (I) can be formulated into an implant for subcutaneous administration. In addition, the compound of Formula (I) can be administered to animals transdermally. For parenteral administration, the selected dosage form should provide the animal with 0.01 mg / kg to 100 mg / kg in body weight of the animal per day of the compound of Formula (!).
[348] The compounds of Formula (I) can also be applied topically to animals in the form of immersion formulations, dust, powders, collars, medallions, sprays, shampoos, “in loco” (spot on) and dumping ( pour on) and in water-in-oil or oil-in-water ointments or emulsions For topical application, dips and sprays usually contain from 0.5 ppm to 5,000 ppm and, preferably, from 1 ppm to 3,000 ppm of the compound of Formula (I) In addition, the compounds of Formula (I) can be formulated as insecticidal earrings for animals, especially quadrupeds such as cattle and sheep:
[349] Suitable preparations, for example, are: - solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour on formulations, gels; - emulsions and suspensions for oral or cutaneous administration, semi-solid preparations; - formulations in which the active compound is processed into an ointment base or an oil-in-water and water-in-oil emulsion base; - solid preparations, such as powders, premixes or concentrates, granules, pellets, tablets, cake pills, capsules, aerosols and inhalants, and the active compounds that contain the molded articles.
[350] Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and, optionally, the addition of other ingredients, such as acids, bases, buffer salts, preservatives and solubilizers. The solutions are filtered and introduced in a sterile medium.
[351] Suitable solvents are physiologically tolerable solvents, such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.
[352] The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils, which are suitable for injection.
[353] Suitable solubilizers are solvents that promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil and polyoxyethylated sorbitan ester.
[354] Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters and n-butanol.
[355] Oral solutions are administered directly. The concentrates are administered orally after dilution, before using the concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injectable solutions, sterile procedures are not necessary.
[356] Solutions for use on the skin are dripped, spread, rubbed, dusted or sprayed.
[357] Solutions for use on the skin are prepared according to the state of the art and as described above for injection solutions, sterile procedures are not necessary.
[358] In general, the “pesticide effective amount” means the amount of the active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, delay, prevention and removal, destruction, or otherwise to reduce occurrence and activity of the target organism. The amount effective as a pesticide can vary according to the various compounds / compositions used in the present invention. A pesticide-effective amount of the compositions will also vary according to prevailing conditions, such as the desired effect and parasiticidal duration, target species, mode of application, and the like.
[359] The compositions that can be used in the present invention, in general, can comprise from about 0.001 to 95% by weight of the compound of Formula (I).
[360] In general, it is favorable to apply the compounds of Formula (I), in total amounts from 0.5 mg / kg to 100 mg / kg per day, preferably from 1 mg / kg to 50 mg / kg per day .
[361] Ready-to-use preparations contain compounds that act against parasites, preferably ectoparasites, in concentrations from 10 ppm to 80% by weight, preferably from 0.1 to 65% by weight more preferably from 1 to 50% by weight, most preferably from 5 to 40% by weight.
[362] Preparations that are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90% by weight, preferably from 1 to 50% by weight.
[363] In addition, the preparations comprise the compounds of Formula (I) against endoparasites in concentrations of 10 ppm to 2% by weight, preferably from 0.05 to 0.9% by weight, more preferably, from 0.005 to 0.25% by weight.
[364] In a preferred embodiment of the present invention, compositions comprising the compounds of Formula (I) are applied dermally / topically.
[365] In another preferred embodiment, topical application is carried out in the form of molded articles containing the compound, such as collars, medallions, insecticidal earrings, fixation strips on body parts, and strips and adhesive sheets.
[366] In general, it is favorable to apply the solid formulations that release the compounds of Formula (I), in total amounts from 10 mg / kg to 300 mg / kg, preferably from 20 mg / kg to 200 mg / kg, most preferably, from 25 mg / kg to 160 mg / kg of body weight of the treated animal, over the course of three weeks.
[367] For the preparation of molded articles, flexible thermoplastics and plastics, as well as thermoplastic elastomers and elastomers are used. Suitable plastics and elastomers are polyvinyl, polyurethane, polyacrylate resins, epoxy resins, cellulose, cellulose derivatives, polyamides and polyesters that are sufficiently compatible with the compounds of Formula (I). A detailed list of plastics and elastomers, as well as the procedures for preparing molded articles, is provided, for example, in publication WO 2003/086075.
[368] The present invention is currently illustrated in greater detail by the following examples, without imposing any limitations on it. S. EXAMPLES OF SYNTHESIS EXAMPLE 1 SYNTHESIS1
[369] Synthesis of Example numbered C-3: 6- (6-chloro-3-pyridyl) -1- isopropyl-3-methyl-4-oxo-7,8-dihydro-6H-pyrrole [1,2-a ] pyrimidin-1-ium-2-olate

[370] To a solution of LIAH4 (25 g, 0.65 mol) in THF (1,500 ml) was added a solution of 6-chloropyridin-3-carboxylic acid (50 g, 0.323 mol) in THF dropwise at 0o C, and the mixture was stirred for 3 h at 0 ° C. THF and Na2Sθ4 x 5H2O were slowly added. After stirring for 20 min, the mixture was filtered and the filtrate was concentrated to provide the crude product (26 g, yield: 57.1%). STEP 1.2 - 6-chloropyridin-3-carbaldehyde
[371] To a solution of PCC (58 g, 0.27 mol) in DCM (1,500 mL) was added the product from the previous step (26 g, 0.184 mol) as a solution in DCM, dropwise, at 0 ° C The mixture was then stirred for 2 h at 20 ° C. It was filtered through diatomaceous earth and the contents of the filters were washed with DCM. The organic phase was concentrated to provide the crude product, which was purified by column chromatography to provide the product (15 g, yield: 60.1%).
[372] NMR 1H (400 MHz, CDCh): δ 10.067 (s, 1H), 8.874 (s, 1H, J = 3 Hz), from 8.158 to about 8.138 (d, 1H, J = 8 Hz), from 7.534 to about 7.513 (d, 1H, J = 8 Hz) STEP 1.3 - Methyl 4- (6-chloro-3-pyridyl) -4-oxo-butanoate
[373] To a solution of 6-chloropyridin-3-carbaldehyde (10 g, 70 mmol) in DMF (40 mL) was added NaCN (0.7 g, 14 mmol). The mixture was stirred for 1 h followed by the dropwise addition of methyl acrylate (5.2 g, 60 mmol). Stirring was continued for 3 h at room temperature, the solution was poured into water, and extracted with EtOAc. The organic phase was dried, filtered and concentrated to provide methyl 4- (6-chloro-3-pyridyl) -4-oxo-butanoate (6.8 g, yield: 42.5%).
[374] NMR 1H (400 MHz, CDCh): δ from 8.971 to about 8.968 (m, 1H), from 8.219 to about 8.198 (d, 1H, J = 8.4 Hz), from 7.462 to about 7.441 (d, 1H, J = 8.4 Hz), 3.710 (s, 3H), from 3.306 to about 3.274 (m, 1H), from 2.812 to about 2.760 (m, 2H). STEP 1.4 - 5- (6-chloro-3-pyridyl) pyrrolidin-2-one
[375] To a solution of methyl 4- (6-chloro-3-pyridyl) -4-oxo-butanoate (6.7 g, 29.5 mmol) in MeOH (100 mL) was added NH4OAC (6, 8 g, 88.3 mmol) and NaBHsCN (5.6 g, 88.3 mmol), and the mixture was refluxed overnight. The solvent was removed in vacuo, the residue was dissolved in DCM, washed with brine, dried, and concentrated to provide the crude product. Purification by column chromatography gave the product (3 g, yield: 51.9%).
[376] NMR 1H (400 MHz, CDCh): δ from 8.336 to about 8.330 (d, 1H, J = 2.4 Hz), from 7.642 to about 7.616 (m, 1H), from 7.361 to about 7.340 (d, 1H, J = 8.4 Hz), 6.987 (s, 1H), from 4.819 to about 4.782 (m, 1H), from 2.634 to about 2.482 (m, 1H), from 2.474 to about 2.432 (m, 2H), from 1.967 to about 1.935 (m, 1H). STEP 1.5 - 5- (3-pyridyl-6-chlorine) pyrrolidine-2-thione
[377] To a solution of the compound from the previous step (2.4 g, 12.24 mmol) in dioxane (150 mL) was added P2S5 (3.3 g, 14.7 mmol) at room temperature. The mixture was heated to 110 ° C and stirred for 2.0 h. After filtration of the hot mixture, the filtrate was concentrated to produce the crude material. Purification by column chromatography obtained the pure product (1.56 g, yield: 60.2%). STEP 1.6 - 2-chloro-5- (5-methylsulfanyl-3,4-dihydro-2H-pyrrol-2-yl) pyridine
[378] To a solution of 5- (6-chloro-3-pyridyl) pyrrolidine-2-thion (2 g, 9.4 mmol) in acetone (100 mL) was added K2CO3. After stirring at room temperature for 30 min, iodomethane was added and stirred for an additional 3 h at room temperature. After filtration, the filtrate was concentrated to provide the crude material. Purification by column chromatography yielded the pure product (2.1 g, yield: 97.6%).
[379] NMR 1H (400 MHz, CDCh): δ 8.320 (s, 1H), from 7.564 to about 7.544 (d, 1H, J = 8.0 Hz), from 7.298 to about 7.278 (d, 1H, J = 8.0 Hz), from 5.105 to about 5.068 (m, 1H), from 2.856 to about 2.792 (m, 2H), from 2.634 to about 2.513 (m, 2H), 2.179 (s, 3H) , from 1.820 to about 1.255 (m, 1H). STEP 1.7 - 2- (6-chloro-3-pyridyl) -N-isopropyl-3,4-dihydro-2H-pyrrole-5-amine
[380] For the product from step 6 (0.25 g, 1.03 mmol) in THF (30 mL), isopropylamine (580 mg, 10.3 mmol) was added and the mixture was heated in a sealed tube at 130 ° C overnight. It was cooled to 20 ° C, the solvent was removed in vacuo. The residue was dissolved in EtOAc (60 ml), washed with water (30 ml), brine, and concentrated to provide the product (230 mg, yield: 88.1 %). STEP 1.8 3- (6-chloro-3-pyridyl) -8- (dimethylamino) -5-oxo-6-phenyl-1,2,3,8-tetrahydroindolizin-4-ium-7-olate.
[381] The product from step 7 (0.23 g, 0.96 mmol) and bis (2,4,6-trichlorophenyl) 2-phenylpropanedioate (0.62 g, 1.2 mmol) was taken in toluene (5 mL) with a few drops of DMF. The reaction mixture was heated in a microwave oven at 150 ° C for 90 min. After cooling to room temperature, poured into water (10 ml), and extracted with EtOAc (45 ml). The organic phase was dried with Na2SO4, and concentrated to provide the crude material. Purification by column chromatography yielded the pure product (0.155 g, yield: 57.8%).
[382] NMR 1H (400 MHz, CDCh): δ from 8,400 to about 8,394 (d, 1H, J = 2.4 Hz), from 7.8818 to about 7.791 (m, 1H), from 7.470 to about from 7.395 (m, 3H), from 7.285 to about 7.142 (m, 3H), from 5.841 to about 5.807 (m, 1H), from 3.771 to about 3.608 (m, 2H), from 2.982 to about 2.869 (m, 2H), from 2.249 to about 2.192 (m, 1H), from 1.722 to about 1.671 (m, 6H). EXAMPLE 2 S2 SUMMARY
[383] Synthesis of Example numbered C-8: 6- (6-chloro-3-pyridyl) -1 - methyl-4-oxo-3-phenyl-6,7,8,9-tetrahydropyride [1,2-a ] pyrimidin-5-ium-2-olate
- methyl 5- (6-chloro-3-pyridyl) -5-oxo-pentanoate
[384] To a mixture of metallic Zn (21.7 g, 0.339 mol) and DMI (38.6 g, 0.339 mol) in MeCN (300 ml) were added under an argon atmosphere 0.2 ml of TMSCI at 60 ° C ° C stirred for 5 min, followed by the addition of methyl 4-iodo-butanoate (58 g, 0.254 mol). The mixture was stirred for 2 hours at this temperature and then cooled to room temperature. This solution was directly used.
[385] To a mixture of 6-chloropyridin-3-carbonyl chloride (14.8 g, 0.085 mol) and Pd (OAc) 2 (0.57 g, 0.00254 mol) in MeCN (300 ml) was added under an argon atmosphere, the alkyl zinc reagent is stirred at room temperature. After 2 hours, the saturated NH4 Cl solution was added to the reaction mixture and extracted with 0 EtOAc. The organic phases were combined, washed with brine, dried, filtered and concentrated to provide the crude product. Purification by column chromatography yielded the pure product (9.5 g).
[386] NMR 1H (400 MHz, CDCh): δ from 8.88 to about 8.89 (d, 1H, J = 2 Hz), from 8.13 to about 8.19 (m, 1H), from 7.36 to about 7.40 (d, 1H, J = 16 Hz), from 4.03 to about 4.01 (q, 2H), from 2.98 to about 3.02 (t, 2H, J = 6.8 Hz), from 2.37 to about 2.407 (t, 2H, J = 7.2 Hz), from 1.98 to about 2.05 (m, 2H), from 1, 15 to about 1.22 (t, 2H, J = 13 Hz). STEP2.2 - 6- (6-chloro-3-pyridyl) -piperidin-2-one
[387] To a solution of methyl 5- (6-chloro-3-pyridyl) -5-oxo-pentanoate (9.5 g, 39.4 mmol) in MeOH (150 mL) was added NH4OAC (6, 1 g, 78.8 mmol) and NaBHaCN (5 g, 78.8 mmol), and the mixture was refluxed overnight. Cooled to room temperature, the solvent was removed in vacuo, the residue was dissolved in DCM, washed with brine, dried concentrated to provide the crude product. Purification by column chromatography yielded the pure product (5 g, yield: 61%). STEP 2.3 - 6- (6-chloro-3-pyridyl) piperidine-2-thione
[388] the pure product (1.5 g, yield: 63.5%). To a solution of 6- (6-chloro-3-pyridyl) -piperidin-2-one (2.2 g, 10.4 mmol) in dioxane (150 mL) was added P2S5 (2.8 g, 12, 6 mmol) at 20 ° C. The mixture was stirred for 2.5 h at 120 ° C. After filtration of the hot mixture, the filtrate was concentrated to produce the crude material. Purification by column chromatography produced STEP 2.4 - 2-chloro-5- (6-methyl-sulfanyl-2,3,4,5-tetrahydropyridin-2-yl) pyridine
[389] To a solution of 6- (6-chloro-3-pyridyl) piperidine-2-thione (1.5 g, 6.64 mmol) in acetone (120 mL) was added K2CO3 and stirred for 30 min, then, iodine methane (1.42 g, 9.96 mmol) was added and stirred overnight at 20 ° C. After filtration, the filtrate was concentrated to provide the crude material. Purification by column chromatography yielded the pure product (1.2 g, yield: 75.3%). STEP 2.5 - 2- (6-chloro-3-pyridyl) -N-methyl-2,3,4,5-tetrahydropyridin-6-amine
[390] 2-chloro-5- (6-methylsulfanyl-2,3,4,5-tetrahydropyridin-2-yl) pyridine (0.6 g, 2.5 mmol) was taken up in methylamine (20 mL , 40 mmol), and the mixture was heated in a sealed tube at 80 ° C overnight. It was cooled to 20 ° C, the solvent was removed in vacuo, the residue was dissolved in EtOAc (60 ml) and washed with water (30 ml), and brine. The organic phase was concentrated to provide the product (480 mg, crude). STEP 2.6 6- (6-chloro-3-pyridyl) -1-methyl-4-oxo-3-phenyl-6,7,8,9-tetrahydropyrido [1,2-a] pyrimidin-5-ium-2-olate
[391] The product from the previous step (0.48 g, crude) and bis (2,4,6-trichlorophenyl) 2-phenylpropanedioate (1.4 g, 2.4 mmol) was taken in toluene (5 mL ) with a few drops of DMF. The reaction mixture was heated in a microwave oven at 150 ° C for 90 min. After cooling to room temperature, it was poured into water (10 ml), and extracted with EtOAc (45 ml). The organic phase was dried with Na2SO4, and concentrated to provide the crude material. Purification by column chromatography yielded the pure product (0.4 g, yield: 50.7%).
[392] NMR 1H (400 MHz, CDCh): δ from 8.381 to about 8.375 (d, 1H, J = 2.4 Hz), from 7.818 to about 7.791 (m, 1H), from 7.552 to about 7.485 (m, 3H), from 7.207 to about 7.048 (m, 3H), from 5.941 to about 5.933 (s, 1H), 3.495 (s, 3H), from 3.236 to about 3.174 (m, 2H), from 2.179 to about 2.123 (m, 2H), from 1.822 to about 1.426 (m, 2H). EXAMPLE 3 S3 SYNTHESIS
[393] Synthesis of Example numbered C-6: 6- (2-chlorothiazol-5-yl) -1- methyl-4-oxo-3-phenyl-3,6,7,8-tetrahydro-2H-pyrrole [1 , 2-a] pyrimidin-5-ium-2-olate

[394] A mixture of 2- (2-chlorothiazol-5-yl) -N-methyl-3,4-dihydro-2H-pyrrole-5-amine (230 mg, 1.07 mmol) and bis 2-phenylpropanedioate (2,4,6-trichlorophenyl) (632 mg, 1.17 mmol) in toluene (10 mL) in a sealed tube was heated to 150 ° C for 90 minutes under microwave irradiation. Cooled to room temperature, the resulting mixture was concentrated, and the residue was purified by preparative TLC to provide 6- (2-chlorothiazol-5-yl) -1-methyl-4-oxo-3-phenyl-3,6 , 7,8-tetrahydro-2H-pyrrolo [1,2-a] pyrimidin-5-ium-2-olate (90 mg, yield: 23%) as a yellow solid.
[395] NMR 1H (400 MHz, CDCh): δ d 7.87 (s, 1H), 7.60 (d, 2H, J = 7.2 Hz), 7.23 (t, 2H, J = 7 , 6 Hz), 7.08 (t, 1H, J = 7.6 Hz), from 5.98 to about 5.95 (m, 1H), from 3.67 to about 3.59 (m, 1H), from 3.51 to about 3.44 (m, 1H), 3.37 (s, 3H), from 2.69 to about 2.67 (m, 1H), from 2.60 to about 2.54 (m, 1H).
[396] The compounds, in general, can be characterized, for example, by coupling High Pressure Liquid Chromatography / mass spectrometry (HPLC / MS), by 1H-NMR and / or by their melting points. CONDITIONS
[397] HPLC analytical column 1: RP-18 column (Merck KgaA Chromolith Speed Rod, Germany). Elution: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0.1% trifluoroacetic acid (TFA), in a ratio from 5:95 to 95: 5, in 5 minutes at 40 ° C . Rt rt = HPLC retention time: m / z of the peaks [M + H] +, [M + Na] + or [M + K] + ..
[398] HPLC analytical column 2: 1.7 pm Phenomenex Kinetex XB-C18 100A, 50 x 2.1 mm elution: A: acetonitrile + 0.1% trifluoroacetic acid (TFA) Water + 0.1% of trifluoroacetic acid (TFA) in a ratio from 5:95 to 95: 5 in 1.5 minutes at 50 ° C.
[399] MS-method: ESI positive.
[400] 1H-NMR, respectively, 13C-NMR: Signals are characterized by chemical shift (ppm) versus tetramethylsilane, respectively CDCh to 13C-NMR, by their multiplicity and by their integer (relative number of hydrogen atoms provided ). The following abbreviations are used to characterize the multiplicity of signs: m = multiplet, q = quartet, t = triplet, d = doublet and s = singlet. The coupling constant (J) is expressed in Hertz (Hz).
[401] Examples of other compounds of the present invention were prepared by analogy with the synthetic methods described above and the Table below illustrates, without any limitation, the Examples of the compounds of Formula (I) including their corresponding characterization data :













[402] The biological activity of the compounds of Formula (I) of the present invention can be evaluated in biological tests, as described below. GENERAL CONDITIONS
[403] Unless otherwise specified, most test solutions are prepared as follows: - the active compound is dissolved in the desired concentration in a mixture of 1: 1 (vokvol) distilled water: acteone. The test solution is prepared on the day of use.
[404] Test solutions, in general, are prepared in concentrations of 2,500 ppm, 1,000 ppm, 500 ppm, 300 ppm, 100 ppm and 30 ppm (w / vol). COTTON BEE (ANTHONOMUS GRANDIS)
[405] For the evaluation of the control of cotton weevil (Anthonomus grandis), the test unit consisted of 96-well microtiter plates containing an insect feed and 5 to 10 A. grandis eggs.
[406] The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of the formulated compounds were sprayed on the insect feed at 5 pL, using a microatomizer built to order, in two repetitions.
[407] After application, the microtiter plates were incubated at about 25 + 1 ° C and about 75 + 5% relative humidity for 5 days. The mortality of the egg and the larva was then assessed visually.
[408] In this test, the compounds of C-3, C-47, C-29, C-40 and C-44 at 2,500 ppm showed mortality greater than 75% compared to untreated controls. GREEN PEACH APHYDE (MYZUS PERSICAE)
[409] For the evaluation of the control of the green aphid of the peach tree (Myzus persicae), through systemic means, the test unit consisted of 96 well microtiter plates containing a liquid artificial feed under an artificial membrane.
[410] The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of the formulated compounds were pipetted into the aphid's feed, using a pipette built to order, in two repetitions.
[411] After application, 5 to 8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then able to suck the treated and incubated aphid feed at about 23 + 1 ° C and about 50 + 5% relative humidity for 3 days. The aphid mortality and fertility were then visually assessed.
[412] In this test, compounds C-1, C-2, C-3, C-6, C-8, C-9, C-12, C-13, C-21, C-34, C- 45, C-23, C-22, C-24, C-27, C-49, C-47, C-48, C-50, C-29, C-40, C-32, C-43, C-44, C-38, C-17, C-41 and C-31 at 2,500 ppm showed mortality greater than 75% compared to untreated controls compared to untreated controls. ORCHID TRIPS (DICHROMOTHRIPS CORBETTÍ)
[413] The adult Dichromothrips corbettí used for biotest were obtained from a colony maintained continuously under laboratory conditions. For test purposes, the test compound is diluted to a concentration of 500 ppm (compound weight: diluent volume) in a 1: 1 mixture of acetone: water (vokvol), plus 0.01% vol / vol of the Alkamuls® EL 620 surfactant.
[414] The thrips potency of each compound was assessed using a floral immersion technique. Plastic Petri dishes were used as test arenas. All petals of the individual intact orchid flowers were immersed in the treatment solution and allowed to dry. The treated flowers were placed in individual petri dishes, together with about 20 adult thrips. The plates were then covered with lids. All test arenas were maintained under continuous light and a temperature of about 28 ° C for the duration of the test. After 3 days, the number of live thrips was counted on each flower, and along the inner walls of each petri dish. The mortality percentage was recorded 72 hours after treatment.
[415] In this test, those with posts C-1, C-2, C-3, C-6, C-8, C-34, C- 45, C-22, C-24, C-27, C -49, C -47, C-28, C-48, C-50, C-29, C-42, C-35 and C-38 at 500 ppm showed a mortality rate greater than 75% compared to non-controls treated. CLGARRINHA GREEN RICE (NEPHOTETTIX VIRESCENS)
[416] Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone: water (vokvol), and 0.1 vol% vol / vol of surfactant (EL 620) was added. The potted rice seedlings were sprayed with 5 mL of test solution, air dried and placed in cages and inoculated with 10 adults. The treated rice vegetables were kept at 28 to 29 ° C and a relative humidity of about 50 to 60%. The mortality percentage was recorded after 72 hours.
[417] In this test, compounds C-1, C-2, C-6, C-8, C-22, C-24, C-47, C-28, C-42 and C-38 at 500 ppm showed mortality greater than 75% compared to untreated controls. CLGARRINHA BROWN RICE (NILAPARVATA LUGENS)
[418] The rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone: water (vokvol), and 0.1 vol% vol / vol of surfactant (EL 620) was added. The potted rice seedlings were sprayed with 5 mL of test solution, air dried and placed in cages and inoculated with 10 adults. The treated rice vegetables were kept at 28 to 29 ° C and a relative humidity of about 50 to 60%. The mortality percentage was recorded after 72 hours.
[419] In this test, compounds C-1, C-6, C-24, C-28, C-29, C-42 and C-38 at 500 ppm showed mortality greater than 75% compared to controls untreated. RED MITE (TETRANYCHUS SPP.)
[420] The active compound is dissolved in the desired concentration in a mixture of 1: 1 (vokvol) distilled water: acetone. The test solution is prepared on the day of use.
[421] The cotton vegetables potted at two weeks of age were cleaned, air dried and inoculated with about 50 mites of various stages. The potted vegetables are sprayed after the registered pest population. The mortality percentage is recorded 72 hours after treatment.
[422] In this test, compounds C-9 and C-42 at 500 ppm showed mortality greater than 75% compared to untreated controls. TOBACCO Caterpillar (HELIOTHIS VIRESCENS)
[423] For the control of tobacco caterpillar (Heliothis virescens) control, the test unit consisted of 96 well microtiter plates containing a liquid artificial feed and 15 to 25 eggs of H. virescens.
[424] The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of the formulated compounds were sprayed on the insect's feed in 10 pl, using a micro atomizer built to order, in two repetitions.
[425] After application, microtiter plates were incubated at about 28 + 1 ° C and about 80 + 5% relative humidity for 5 days. The mortality of the egg and the larva was then visually assessed.
[426] In this test, compounds C-1, C-45, C-44 and C-38 at 2,500 ppm showed mortality greater than 75% compared to untreated controls. PEA PULGÃO (MEGOURA VICIAE)
[427] For the evaluation of the control of vetch (Megoura viciae) through contact or by systemic means, the test unit consisted of 24-well microtiter plates containing broad discs of bean leaves.
[428] The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of the formulated compounds were sprayed onto the leaf discs in 2.5 pL, using a micro atomizer built to order, in two repetitions.
[429] After application, the leaf discs were air-dried and 5 to 8 adult aphids were placed on the leaf discs within the microtiter plate wells. The aphids were then allowed to suck the treated leaf discs and incubated at about 23 + 1 ° C and about 50 + 5% relative humidity for 5 days. The aphid mortality and fertility were then visually assessed.
[430] In this test, compounds C-1, C-2, C-3, C-6, C-8, C-9, C-13, C-34, C-45, C-22, C- 24, C -27, C-49, C-47, C-48, C-50, C-29, C-40, C-44, C-38, C-19 and C-31 at 2,500 ppm showed a mortality greater than 75% compared to untreated controls.

权利要求:
Claims (14)
[0001]
1. SUBSTITUTED PYRIMIDINUM COMPOUNDS, characterized by being of Formula (I)
[0002]
2. COMPOUNDS according to claim 1, characterized in that Het is selected from any of the following ring systems:
[0003]
COMPOUNDS according to any one of claims 1 to 2, characterized in that Het is selected from structures D-2, D-9, D-22, D25, D28, D-29, D-54 and D- 56:
[0004]
COMPOUNDS according to any one of claims 1 to 3, characterized in that A is CH or N, in which the nitrogen of the pyrimidinium ring, taken together with the contiguous carbon atom and A, as represented in the Formula (I), forms a ring of five or six members, in which each member of the remaining ring is selected from carbon atoms and up to a hetero atom selected from O, S and N (RC) P, in which the ring can be replaced by Ra.
[0005]
COMPOUNDS according to any one of claims 1 to 4, characterized in that X and Y are O.
[0006]
6. COMPOUNDS according to any one of claims 1 to 5, characterized in that - Z is a direct bond, and - R2 is a six-membered carbon- or heterocyclic ring, said ring which can be unsubstituted, partially or totally replaced by R2a, and where R2a is halogen, Ci-Cβ haloalkyl, Ci-Cβ haloalkoxy, ORC, C (= O) ORc, C (= O) NRbRc, phenyl, or pyridyl, which can be substituted by halogen, C1- haloalkyl Cβ or Ci-Cβ haloalkoxy.
[0007]
7. COMPOUNDS according to any one of claims 1 to 6, characterized in that - R1 is C1-C4 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, benzyl or phenyl, said groups which may be partially or totally substituted by halogen or C1-C4 alkyl.
[0008]
8. COMPOUNDS according to claim 3, characterized in that - each X, Y is O; - To be CH, and the nitrogen of the pyrimidinium ring, taken together with the carbon atom of contiguous bond and A, as represented in Formula (I), form a ring of five or six members, in which each member of the ring remainder is selected from 2 and 3 carbon atoms; - R1 is CH3, CH2CH3, isopropyl, cyclopropyl, CH2CF3, phenyl, allyl or benzyl; - R2 is phenyl that can be replaced by halogen, haloalkyl Ci-Cβ, haloalkoxy Ci-Cβ or phenyl; - Z is a direct bond and - Het is D-2, D-9 D-25 D-56 or and Ra is Cl, Br, F, SCH3, CF3, OCH3 or phenyl.
[0009]
9. COMPOSITION, characterized in that it comprises at least one compound of Formula (I) as defined in any one of claims 1 to 8 and at least one inert liquid and / or solid vehicle.
[0010]
10. AGRICULTURAL COMPOSITION for the control of pests and animals, characterized by comprising at least one compound of Formula (I) and / or stereoisomers, agriculturally or veterinarily acceptable salts, tautomers or N-oxides thereof, as defined in any of the claims 1 to 8, and at least one inert liquid and / or acceptable solid vehicle and, if desired, at least one surfactant.
[0011]
11. METHOD FOR THE PROTECTION OF CROPS, VEGETABLES, VEGETABLE PROPAGATION MATERIAL and / or plants growing from attack or infestation by invertebrate pests, characterized by understanding the contact or treatment of crops, vegetables, plant propagation material and growing vegetables, or soil, material, surface, space, area or water in which crops, vegetables, plant propagating material are stored or in which the plant grows, with a pesticide-effective amount of at least one compound of Formula (I) and / or stereoisomers or agriculturally or veterinarily acceptable salts or tautomers or N-oxides thereof, as defined in any of claims 1 to 8, or with a composition as defined in any of claims 9 to 10.
[0012]
12. METHOD FOR COMBATING, CONTROL, PREVENTION OR PROTECTION against infestation or infection by invertebrate pests, characterized by the method of understanding the contact of said pest or its supply of food, habitat or breeding ground with an effective amount as a pesticide. at least one compound of Formula (I) and / or stereoisomers or agriculturally or veterinarily acceptable salts or tautomers or N-oxides thereof, as defined in any of claims 1 to 8, or a composition as defined in any of claims 9 to 10.
[0013]
13. USE OF COMPOUNDS OF Formula (I) and / or stereoisomers or agriculturally or veterinarily acceptable salts or tautomers or N-oxides thereof, as defined in any of claims 1 to 8, characterized by being for the protection of growing vegetables or plant propagation material from attack or infestation by invertebrate pests.
[0014]
14. USE OF COMPOUNDS OF Formula (I) and / or stereoisomers or agriculturally or veterinarily acceptable salts or tautomers or N-oxides thereof, as defined in any one of claims 1 to 8, characterized in that it is for the preparation of a veterinary composition for the treatment of animals infested or infected by parasites, to prevent animals from being infected or infested by parasites or for the protection of animals against infestation or infection by parasites.

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法律状态:
2018-02-27| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|

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2019-05-21| B06T| Formal requirements before examination [chapter 6.20 patent gazette]|

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2020-04-14| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2020-06-16| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2020-08-18| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 11/04/2014, OBSERVADAS AS CONDICOES LEGAIS. |

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申请号 | 申请日 | 专利标题

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