USE OF HETEROARYL-TRIAZOLE COMPOUNDS AND HETEROARYL-TETRAZOLE AS PESTICIDES IN PLANT PROTECTION

专利摘要:
the present invention relates to the use of heteroaryl-triazole and heteroaryl-tetrazole compounds, to the use of formulations and compositions comprising such compounds for the control of animal pests, including arthropods and insects, in plant protection.
公开号:BR112020016946A2
申请号:R112020016946-3
申请日:2019-03-05
公开日:2020-12-15
发明作者:Hans-Georg Schwarz；Martin Füsslein；Yolanda Cancho Grande；Arunas Jonas DAMIJONAITIS；Werner Hallenbach；Alexander ARLT；Kerstin Ilg；Marc Linka；Elke Hellwege；Ulrich Ebbinghaus-Kintscher；Sebastian Horstmann；Peter Jeschke
申请人:Bayer Aktiengesellschaft；
IPC主号:

专利说明:

[001] [001] The present invention relates to the use of heteroaryl-triazole and heteroaryl-tetrazole compounds, and to the use of formulations and compositions comprising such compounds for the control of animal pests, including arthropods and insects, in plant protection.
[002] [002] Heteroaryl-triazole and heteroaryl-tetrazole compounds of formula I for use in the control of ectoparasites in animals are described in WO 2017/192385. Plant protection properties have not been described or described.
[003] [003] Crop protection compositions, which also include pesticides, need to satisfy many requirements, for example, in terms of effectiveness, persistence, spectrum, resistance loss properties, pollination and advantageous safety of their action and possible use. Toxicity problems, the ability to combine with other active compounds or formulation aids have their role, as well as the problem of the expenses necessary for the synthesis of an active compound. In addition, resistance is likely to occur. For all these reasons, the search for new compositions for crop protection cannot be considered finished, and new compounds are constantly needed, presenting properties that, compared to known compounds, are improved at least in relation to individual aspects.
[004] [004] An objective of the present invention was to present compounds that expand the spectrum of plant protective pesticides in several aspects. Surprisingly, it has been discovered that known heteroaryl-triazole and heteroaryl-tetrazole compounds of formula I have broad insecticidal activity in the field of plant protection.
[005] [005] The present invention therefore presents the use of compounds of formula I:
[006] [006] In an alternative embodiment, the present invention features the use of compounds of formula I: (I) where: X is O or S; Q1 and Q2 are independently CR5 or N, provided that at least one of Q1 and Q2 is N; Y is a direct bond or CH2; R1 is H; C1-C6alkyl optionally substituted with a substituent selected from: CN, CONH2, COOH and NO2; C1-C6haloalkyl; C2-C6 alkenyl; C2-C6haloalkenyl: C2-C6alkynyl; C2-C6haloalkynyl; C3-C4cycloalkyl-C1-C2alkyl- where C3-C4cycloalkyl is optionally substituted with 1 or 2 halogen atoms; oxetan-3-yl-CH2-; or benzyl optionally substituted with halo or C1-C3haloalkyl; R2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, where phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided that the substituents are not on any carbon adjacent to the carbon attached to the group, each one independently selected from: C1- C3alkyl, C1-C3haloalkyl, C1-C3haloalkylsulfanyl, C1- C3alkoxy, C1-C3haloalkoxy, halo, NO2, SF5, CN, CONH2 and COOH; R3 is C1-C3alkyl or C1-C3haloalkyl; R4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with a substituent selected from: C1- C3alkyl; C1-C3haloalkyl, C1-C3alkoxy, C1- C4cycloalkyl, halo or hydroxy; R5 is H, C1-C3alkyl, C1-C3haloalkyl, C3-C4cycloalkyl or C1-C3alkoxy; or a salt thereof, for the control of animal pests including arthropods and insects in plant protection.
[007] [007] As will be perceived by the person skilled in the art, compounds of formula I contain a stereogenic center which is indicated by an asterisk in the structure below: (I)
[008] [008] The present invention contemplates the use of both racemates and individual enantiomers. The compounds with preferred stereochemistry are shown below.
[009] [009] Preferred compounds of formula I or salts thereof include compounds having one or more of the following attributes: a) Y is a direct bond; b) X is O: c) X is S; d) R3 is methyl; e) Q1 is N; f) Q2 is CR5 and R5 is H, C1-C3alkyl, C1-C3alkoxyC (O) -, or (C1- C3alkoxy) 2CH-; f-2) Q2 is CR5 and R5 is H, C1-C3alkyl, C1-C3alkoxyC (O) -, (C1- C3alkoxy) 2CH- or C1-C3haloalkyl; g) Q2 is CR5 and R5 is H, C1-C3alkyl, or (C1-C3alkoxy) 2CH-; g-2) Q2 is CR5 and R5 is H, C1-C3alkyl, (C1-C3alkoxy) 2CH- or C1- C3haloalkyl; h) Q2 is CR5 and R5 is H or C1-C3alkyl; h-2) Q2 is CR5 and R5 is H, C1-C3alkyl or C1-C3haloalkyl; i) Q2 is CR5 and R5 is H, methyl or (CH3CH2O) 2CH-; i-2) Q2 is CR5 and R5 is H, methyl, (CH3CH2O) 2CH- or CF3; j) Q2 is CR5 and R5 is H or methyl; j-2) Q2 is CR5 and R5 is H, methyl or CF3; k) Q2 is CR5 and R5 is H; k-2) Q2 is CR5 and R5 is H or CF3; l) Q1 is N, Q2 is CR5 and R5 is H, methyl or (CH3CH2O) 2CH-; 1-2) Q1 is N, Q2 is CR5 and R5 is H, methyl, (CH3CH2O) 2CH- or CF3; m) Q1 is N, Q2 is CR5 and R5 is H or methyl; m-2) Q1 is N, Q2 is CR5 and R5 is H, methyl or CF3;
[0010] [0010] For the control of animal pests, including arthropods and insects, in plant protection, the preferred compounds of the present invention are compounds of formula II ': (II') X is O or S; R1 is H; C1-C6haloalkyl; C1-C6alkyl optionally substituted with CN or -Si (CH3) 3; C3-C6alkynyl; C3-C4cycloalkyl-C1- C2alkyl where C3-C4cycloalkyl is optionally substituted with 1 or 2 halogen atoms; oxetan-3-yl-CH2-; or benzyl optionally substituted with halo; R2 is phenyl, 3-pyridine or 4-pyridine substituted with one to three substituents selected from: C1-C3haloalkyl, C1- C3haloalkoxy, C1-C3haloalkylsulfanyl, halo, CN or C (S) NH2, provided that the substituents are not in any carbon adjacent to the carbon attached to the group; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, where 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1-C3alkoxy, halo, or C1- C3haloalkyl;
[0011] [0011] In an alternative embodiment, for the control of animal pests, including arthropods and insects, in plant protection, the preferred compounds of the present invention are compounds of formula II ': (II') X is O or S; R1 is H; C1-C6haloalkyl; C1-C6alkyl optionally substituted with CN or -Si (CH3) 3; C3-C6alkynyl; C3-C4cycloalkyl-C1- C2alkyl where C3-C4cycloalkyl is optionally substituted with 1 or 2 halogen atoms; oxetan-3-yl-CH2-; or benzyl optionally substituted with halo; R2 is phenyl, 2-pyridine, 2-pyrazine, 3-pyridine or 4-pyridine substituted with one to three substituents selected from: C1-C3alkyl, C1-C3haloalkyl, C1-C3haloalkoxy, C1-C3haloalkylsulfanyl, halo, CN or C ( S) NH2, provided that the substituents are not on any carbon adjacent to the carbon attached to the group; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, where 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1-C3alkoxy, halo, C1-C3haloalkyl, or C1-C3alkyl;
[0012] [0012] For the control of animal pests, including arthropods and insects, in plant protection, the preferred compounds of the present invention are compounds of formula II: (II) where: R1 is H; C1-C6haloalkyl; C1-C6alkyl; C3-C6alkynyl; benzyl, 3-oxetanyl or C3-C4cycloalkyl-C1-C2alkyl where C3-C4cycloalkyl is optionally substituted with 1 or 2 halogen atoms; R2 is phenyl or 3-pyridine substituted with one to three substituents selected from C1-C3haloalkyl, C1-C3haloalkoxy, C1- C3haloalkylsulfanyl, halo or CN, provided that the substituents are not on any carbon adjacent to the carbon attached to the group; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, where 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1-C3alkoxy, halo, or C1-C3haloalkyl R5 is H or C1-C3alkyl , or a salt thereof.
[0013] [0013] In an alternative embodiment, for the control of animal pests, including arthropods and insects, in plant protection, the preferred compounds of the present invention are compounds of formula II:
[0014] [0014] For the control of animal pests, including arthropods and insects, in plant protection, the particularly preferred compounds of the present invention are compounds of formula II'a or IIa: (II'a) (IIa) where X, R1 , R2, R4 and R5 have the definitions for formula II 'or formula II respectively; or a salt from them.
[0015] [0015] For the control of animal pests, including arthropods and insects, in plant protection, preferred compounds of formula I, II 'and II'a, or salts thereof, include those in which R1 is H, cyclopropyl-CH2- , cyclobutyl-CH2, CH3-, CH3CH2-, n-propyl, CH≡C- CH2-, CF3CH2CH2-, CHF2CH2, - FCH2CH2-, FCH2CH2CH2-, 2,2-difluorocyclopropyl-CH2-, 2,2-dichlorocyclopropyl-CH2 -, benzyl, 4-fluorobenzyl, 3-oxetanyl, (CH3) 3SiCH2-, or CN-CH2-; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylsulfanylphenyl 5-trifluoromethylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethylphenyl or 2,6-bis (trifluoromethyl) pyridin-4-yl; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, wherein 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1- C3alkoxy, halo, or C1-C3haloalkyl; and R5 is H, methyl or (CH3CH2O) 2CH-.
[0016] [0016] In an alternative modality, for the control of animal pests, including arthropods and insects, in plant protection, preferred compounds of formula I, II 'and II'a, or salts thereof, include those in which R1 is H , cyclopropyl-CH2-, cyclobutyl-CH2, CH3-, CH3CH2-, n-propyl, CH≡C-CH2-, CF3CH2CH2-, CHF2CH2, - FCH2CH2-, FCH2CH2CH2-, 2,2-difluorocyclopropyl-CH2-, 2, 2- dichlorocyclopropyl-CH2-, benzyl, 4-fluorobenzyl, 3-oxetanyl, (CH3) 3SiCH2-, or CN-CH2-; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, 3-bromo-5-chlorophenyl, 3-iodo-5-chlorophenyl, 4-chloro-3,5-difluorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-fluoro-5-cyanophenyl, 3-chloro - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3-chloro-5-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylsulfanylphenyl, 5-trifluoromethylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethylphenyl, 4-trifluoromethyl-6-chloropyridin-2-yl, 4,6-dichloropyrin 2-yl, 6-chloropyridazin-2-yl, or 2,6-bis (trifluoromethyl) pyridin-4-yl; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, wherein 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1- C3alkoxy, halo, C1-C3haloalkyl or C1-C3alkyl; and R5 is H, methyl, (CH3CH2O) 2CH- or trifluoromethyl.
[0017] [0017] For the control of animal pests, including arthropods and insects, in plant protection, preferred compounds of formula I, II ', II, II'a and IIa, or salts thereof, include those in which R1 is H, cyclopropyl-CH2-, cyclobutyl-CH2, CH3-, CH3CH2-, n-propyl, CH≡C- CH2-, CF3CH2CH2-, CHF2CH2-, FCH2CH2-, FCH2CH2CH2-, benzyl, 4-fluorobenzyl, 3-oxetanyl, 2, 2-difluorocyclopropyl-CH2- or 2,2-dichlorocyclopropyl-CH2-; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,4,5-trichlorophenyl 3-chlorophenyl, 4-chlorophenyl, 3,4-
[0018] [0018] In an alternative modality, for the control of animal pests, including arthropods and insects, in plant protection, preferred compounds of formula I, II ', II, II'a and IIa, or salts thereof, include those in which R1 is H, cyclopropyl-CH2-, cyclobutyl-CH2, CH3-, CH3CH2-, n-propyl, CH≡C-CH2-, CF3CH2CH2-, CHF2CH2-, FCH2CH2-, FCH2CH2CH2-, benzyl, 4-fluorobenzyl, 3 -oxetanil, 2,2-difluorocyclopropyl-CH2-, 2,2-dichlorocyclopropyl-CH2- or CN-CH2-; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, 3-bromo-5-chlorophenyl, 3-iodo-5-chlorophenyl, 3,4,5-trichlorophenyl, 4- chloro-3,5-difluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 3-chloro-phenyl 5-trifluoromethylsulfanylphenyl, 5-trifluoromethylpyridin-3-yl, 5-bromopyridin-3-yl, 5-trifluoromethylsulfanylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethyl-phenyl-clyl-3-trifluoromethyl-phenyl 5-cyanophenyl, 3-fluoro-5-cyanophenyl, 3-trifluoromethoxy-5-chlorophenyl, 3-trifluoromethylsulfanylphenyl, 3-chloro - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3-trifluoromethylsulfanyl-5-chlorophenyl, 4-trifluoromethyl-6-chloropyridin-2-yl, 4,6-dichloropyridin-2-yl, 6-chloropyridazin-
[0019] [0019] For the control of animal pests, including arthropods and insects, in plant protection, most preferred compounds of formula I, II ', II, II'a and IIa, or salts thereof, include those in which R1 is H , cyclopropyl-CH2-, cyclobutyl-CH2, CH3-, CH3CH2-, n-propyl, CH≡C- CH2-, CF3CH2CH2-, CHF2CH2-, FCH2CH2-, FCH2CH2CH2-, benzyl, 4-fluorobenzyl, 3-oxetanil or 2 , 2-difluorocyclopropyl-CH2-; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,4,5-trichlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5- trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 5-trifluoromethylpyridin-3-yl, 5-bromopyridin-3-yl, 5-trifluoromethylsulfanylpyridin-3-yl, 3-bromo-5-trifluoromethane 5-trifluoromethyl-phenyl, 3-chloro-5-cyanophenyl, 3-trifluoromethoxy-5-chlorophenyl, 3-trifluoromethylsulfanylphenyl, 3-trifluoromethylsulfanyl-5-chlorophenyl, 3-chloro-5-trifluoromethylsulfanylphenyl, or 2,6-trifluorine ) pyridin-4-yl; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, wherein 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1- C3alkoxy, halo, or C1-C3haloalkyl; and R5 is H or methyl.
[0020] [0020] In an alternative modality, for the control of animal pests, including arthropods and insects, in the protection of plants, most preferred compounds of formula I, II ', II, II'a and IIa, or salts thereof, include those in which R1 is H, cyclopropyl-CH2-, cyclobutyl-CH2, CH3-, CH3CH2-, n-propyl, CH≡C-CH2-, CF3CH2CH2-, CHF2CH2-, FCH2CH2-, FCH2CH2CH2-, benzyl, 4-fluorobenzyl, 3-oxetanyl, 2,2-difluorocyclopropyl-CH2- or CN-CH2-; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, 3-bromo-5-chlorophenyl, 3-iodo-5-chlorophenyl, 3,4,5-trichlorophenyl, 4- chloro-3,5-difluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 5-trifluoromethylpyridinyl 3-yl, 5-bromopyridin-3-yl, 5-trifluoromethylsulfanylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethyl-phenyl, 3-chloro-5-cyanophenyl, 3-fluoro- 5-cyanophenyl, 3-trifluoromethoxy-5-chlorophenyl, 3-trifluoromethylsulfanylphenyl, 3-chloro- [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3-trifluoromethylsulfanyl-5-chlorophenyl, 3-chloro-5-trifluoromethylsulfan, 4-trifluoromethyl-6-chloropyridin-2-yl, 4,6-dichloropyridin-2-yl, 6-chloropyridazin-2-yl, or 2,6-bis (trifluoromethyl) pyridin-4-yl; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, wherein 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1- C3alkoxy, halo, C1-C3haloalkyl or C1-C3alkyl; and R5 is H, methyl or trifluoromethyl.
[0021] [0021] For the control of animal pests, including arthropods and insects, in plant protection, most preferred compounds of formula I, II ', II, II'a and IIa, or salts thereof, include those in which R1 is H , cyclopropyl-CH2-, cyclobutyl-CH2-, CH3-, CH3CH2-, n-propyl, CH≡C-CH2-, CF3CH2CH2-, CHF2CH2-, FCH2CH2, FCH2CH2CH2-, benzyl or 3-oxetanil; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,4,5-trichlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5- trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-
[0022] [0022] In an alternative modality, for the control of animal pests, including arthropods and insects, in the protection of plants, most preferred compounds of formula I, II ', II, II'a and IIa, or salts thereof, include those in which R1 is H, cyclopropyl-CH2-, cyclobutyl-CH2-, CH3-, CH3CH2-, n-propyl, CH≡C-CH2-, CF3CH2CH2-, CHF2CH2-, FCH2CH2, FCH2CH2CH2-, benzyl, 4-fluorobenzyl; 3-oxetanil or CN-CH2-; R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, 3-bromo-5-chlorophenyl, 3-iodo-5-chlorophenyl, 3,4,5-trichlorophenyl, 4- chloro-3,5-difluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 3-chloro-phenyl 5-trifluoromethylsulfanylphenyl, 5-trifluoromethylpyridin-3-yl, 5-bromopyridin-3-yl, 5-trifluoromethylsulfanylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethyl-3-trifluoromethyl-phenyl 5-cyanophenyl, 3-fluoro-5-cyanophenyl, 3-trifluoromethoxy-5-chlorophenyl, 3-trifluoromethylsulfanylphenyl, 3-chloro- [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3-trifluoromethylsulfanyl-5-chlorophenyl, 4-trifluoromethyl-6-chloropyridin-2-yl, 4,6-dichloropyridin-2-yl, 6-chloropyridazin-2-yl, or 2,6-bis (trifluoromethyl) pyridin-4-yl; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, where 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1- C3alkoxy, halo, C1-C3haloalkyl, or C1-C3alkyl; and R5 is H, methyl or trifluoromethyl.
[0023] [0023] For the control of animal pests, including arthropods and insects, in the protection of plants, most preferred compounds of formula I, II ', and II'a, or salts thereof, include those in which R1 is H, cyclopropyl- CH2-, cyclobutyl-CH-2, CH3, CH3CH2-, CF3CH2CH2-, CHF2CH2-, benzyl, 3-oxetanyl, or CH≡C-CH2-: R2 is 3,5- bis (trifluoromethyl) phenyl, 3,5- dichlorophenyl, 3,4,5-trichlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 5- trifluoromethylpyridin-3-yl, 5-bromopyridin-3-yl, 5-trifluoromethylsulfanylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethyl-phenyl, 3-chloro-5-cyanophenyl, 3- trifluoromethoxy-5-chlorophenyl, 3-chloro-5-trifluoromethylsulfanylphenyl, 3-trifluoromethylsulfanylphenyl, 3-trifluoromethylsulfanyl-5-chlorophenyl, or 2,6-bis (trifluoromethyl) pyridin-4-yl; R4 is 2-pyridine, 3-pyridine, 4-pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, wherein 2-pyridine, 3-pyridine, 4- pyridine 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine is optionally substituted with a substituent selected from: C1- C3alkoxy, halo, or C1-C3haloalkyl: and R5 is H, methyl or (CH3CH2O) 2CH-.
[0024] [0024] In an alternative modality, for the control of animal pests, including arthropods and insects, in the protection of plants, most preferred compounds of formula I, II ', and II'a, or salts thereof, include those in which R1 is H, cyclopropyl-CH2-, cyclobutyl-CH2, CH3-, CH3CH2-, CF3CH2CH2-, CHF2CH2-, benzyl, 4-fluorobenzyl, 3-
[0025] [0025] For the control of animal pests, including arthropods and insects, in plant protection, a preferred compound of the present invention is N- (cyclopropylmethyl) -N- [l- (2-pyrimidin-2-yl-1,2 , 4-triazol-3-yl) ethyl] - 3,5-bis (trifluoromethyl) benzamide (I-48), or a salt thereof. An especially preferred compound is N- (cyclopropylmethyl) -N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -3,5-bis ( trifluoromethyl) benzamide (I-49), or a salt thereof. Another preferred compound of the present invention is N-prop-2-ynyl-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -3,5-bis (trifluoromethyl) benzamide (I-35), or a salt thereof. An especially preferred compound is N-prop-2-ynyl-N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -3,5- bis (trifluoromethyl) benzamide (I-46), or a salt thereof. Another preferred compound of the present invention is N-methyl- N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -3,5-bis (trifluoromethyl) benzamide (I-65), or a salt thereof. An especially preferred compound is N-methyl-N- [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -3,5-bis (trifluoromethyl) -benzamide (I-75), or a salt thereof.
[0026] [0026] Another preferred compound of the present invention is 3-chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] - 5- (trifluoromethyl) benzamide (I-06), or a salt thereof.
[0027] [0027] Another preferred compound of the present invention is 3-chloro-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) - N- (3,3,3-trifluoropropyl) benzamide (I-26), or a salt thereof.
[0028] [0028] Another preferred compound of the present invention is N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl ) pyridine-3-carboxamide (I-28), or a salt thereof.
[0029] [0029] Another preferred compound of the present invention is 3-chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] - 5- (trifluoromethoxy) benzamide (I-37), or a salt thereof.
[0030] [0030] Another preferred compound of the present invention is 3-cyano-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] benzamide (I-38), or a salt thereof.
[0031] [0031] Another preferred compound of the present invention is 3-chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] - 5- (trifluoromethyl) benzamide (I-40), or a salt thereof.
[0032] [0032] Another preferred compound of the present invention is 3-chloro-N-prop-2-ynyl-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl ] -5- (trifluoromethyl) benzamide (I-41), or a salt thereof.
[0033] [0033] Another preferred compound of the present invention is 3-cyano-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] - 5- (trifluoromethyl) benzamide (I-50), or a salt thereof.
[0034] [0034] Another preferred compound of the present invention is 3-bromo-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] - 5- (trifluoromethyl) benzamide (I-62), or a salt thereof.
[0035] [0035] Another preferred compound of the present invention is N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -3,5-bis (trifluoromethyl) benzamide ( I- 63), or a salt thereof. An especially preferred compound is N- [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -3,5-bis (trifluoromethyl) benzamide (I- 66), or a salt thereof.
[0036] [0036] Another preferred compound of the present invention is 3-chloro-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide (I-76), or a salt thereof. An especially preferred compound is 3-chloro-N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide (I -113), or a salt thereof.
[0037] [0037] Another preferred compound of the present invention is 3-chloro-N- (cyclopropylmethyl) -N- [1- [2- (5-fluoropyrimidin-2-yl) -5-methyl-1,2,4-triazole -3-yl] ethyl] -5- (trifluoromethyl) benzamide (I-77), or a salt thereof.
[0038] [0038] Another preferred compound of the present invention is 3-chloro-N- [1- [2- (5-chloropyrimidin-2-yl) -5-methyl-1,2,4-triazol-3-yl] ethyl ] -N- (cyclopropylmethyl) -5- (trifluoromethyl) benzamide (I-78), or a salt thereof.
[0039] [0039] Another preferred compound of the present invention is 3-chloro-N- [1- [2- (5-chloropyrimidin-2-yl) -1,2,4-triazol-3-yl] ethyl] -N- (cyclopropylmethyl) -5- (trifluoromethyl) benzamide (I-80), or a salt thereof.
[0040] [0040] Another preferred compound of the present invention is 3-chloro-N- (cyclopropylmethyl) -N- [1- [2- (5-fluoropyrimidin-2-yl) -1,2,4-triazol-3-yl ] ethyl] -5- (trifluoromethyl) benzamide (I-81), or a salt thereof.
[0041] [0041] Another preferred compound of the present invention is 3-chloro-N- [1- [2- (5-chloro-2-pyridyl) -1,2,4-triazol-3-yl] ethyl] -N- (cyclopropylmethyl) - 5- (trifluoromethyl) benzamide (I-84), or a salt thereof.
[0042] [0042] Another preferred compound of the present invention is 3-chloro-N- (2,2-difluoroethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl ) ethyl] -5- (trifluoromethyl) benzamide (I-89), or a salt thereof.
[0043] [0043] Another preferred compound of the present invention is N- [1- [2- (5-bromopyrimidin-2-yl) -1,2,4-triazol-3-yl] ethyl] -3-chloro-N- (cyclopropylmethyl) -5- (trifluoromethyl) benzamide (I-92), or a salt thereof.
[0044] [0044] Another preferred compound of the present invention is 3-chloro-N- (cyclopropylmethyl) -N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl ) ethyl] - 5- (trifluoromethyl) benzamide (I-93), or a salt thereof.
[0045] [0045] Another preferred compound of the present invention is 3-chloro-N-ethyl-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide (I-97), or a salt thereof.
[0046] [0046] Another preferred compound of the present invention is 3-chloro-N-methyl-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide (I-100), or a salt thereof.
[0047] [0047] Another preferred compound of the present invention is 3-chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] - 5- (trifluoromethylsulfanyl) benzamide (I-107), or a salt thereof.
[0048] [0048] Another preferred compound of the present invention is 3-chloro-5-cyano-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] benzamide (I - 114), or a salt thereof.
[0049] [0049] Another preferred compound of the present invention is 3-chloro-N - [(1S) -1- [2- (2-pyridyl) -1,2,4-triazol-3-yl] ethyl] -5- (trifluoromethyl) benzamide (I-117), or a salt thereof.
[0050] [0050] Another preferred compound of the present invention is 3-chloro-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethoxy) benzamide (I-119), or a salt thereof.
[0051] [0051] Another preferred compound of the present invention is 3-chloro-N - [(1S) -1- [2- (5-chloro-2-pyridyl) -1,2,4-triazol-3-yl] ethyl ] -5-
[0052] [0052] Another preferred compound of the present invention is 3-chloro-N- (2,2-difluoroethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl ) ethyl] -5- (trifluoromethoxy) benzamide (I-121), or a salt thereof.
[0053] [0053] Another preferred compound of the present invention is 3-bromo-5-chloro-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] benzamide (I - 125), or a salt thereof.
[0054] [0054] Another preferred compound of the present invention is 3-chloro-5-iodo-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] benzamide (I - 126), or a salt thereof.
[0055] [0055] Another preferred compound of the present invention is 3-chloro-N- (2,2-difluoroethyl) -N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazole -3-yl) ethyl] - 5- (trifluoromethyl) benzamide (I-127), or a salt thereof.
[0056] [0056] Another preferred compound of the present invention is N- [(1S) -1- [2- (5-bromo-2-pyridyl) -1,2,4-triazol-3-yl] ethyl] -3- chloro-5- (trifluoromethyl) benzamide (I-129), or a salt thereof.
[0057] [0057] Another preferred compound of the present invention is 3-chloro-N - [(1S) -1- [2- (5-chloro-2-pyridyl) -5- (trifluoromethyl) -1,2,4-triazole -3- yl] ethyl] -5- (trifluoromethyl) benzamide (I-131), or a salt thereof.
[0058] [0058] Another preferred compound of the present invention is 3-chloro-N - [(1S) -1- [2- (5-iodo-2-pyridyl) -1,2,4-triazol-3-yl] ethyl ] -5- (trifluoromethyl) benzamide (I-132), or a salt thereof.
[0059] [0059] Another preferred compound of the present invention is N- [(1S) -1- [2- (5-chloro-2-pyridyl) -5- (trifluoromethyl) -1,2,4-triazol-3-yl ] ethyl] -3,5- bis (trifluoromethyl) benzamide (I-136), or a salt thereof.
[0060] [0060] Another preferred compound of the present invention is 3-bromo-5-chloro-N - [(1S) -1- [2- (5-chloro-2-pyridyl) -1,2,4-triazole-3 - yl] ethyl] benzamide (I-137), or a salt thereof.
[0061] [0061] Another preferred compound of the present invention is 3,5-bis (trifluoromethyl) -N - [(1S) -1- [2- [5- (trifluoromethyl) pyrimidin-2-yl] -1,2,4 -
[0062] [0062] Another preferred compound of the present invention is 3-chloro-N - [(1S) -1- [2- (5-fluoro-2-pyridyl) -1,2,4-triazol-3-yl] ethyl ] -5- (trifluoromethyl) benzamide (I-143), or a salt thereof.
[0063] [0063] Another preferred compound of the present invention is 3-chloro-N - [(1S) -1- [2-pyrimidin-2-yl-5- (trifluoromethyl) -1,2,4-triazol-3-yl ] ethyl] -5- (trifluoromethyl) benzamide (I-145), or a salt thereof.
[0064] [0064] Another preferred compound of the present invention is 3-chloro-5- (trifluoromethyl) -N - [(1S) -1- [2- [5- (trifluoromethyl) -2-pyridyl] -1,2,4 - triazol-3-yl] ethyl] benzamide (I-151), or a salt thereof.
[0065] [0065] However, the use of compounds of formula (I), (II), (II '), (IIa) and (IIa') in the control of ectoparasites in animals is excluded.
[0066] [0066] In a preferred embodiment, the invention concerns the use of the compounds of formula (I), (II), (II '), (IIa) and (IIa') in the control of insects of the order of Blattodea, Coleoptera, Dermaptera, Diptera, Hemiptera, Heteroptera, Hymenoptera, Isopoda, Isoptera, Lepidoptera, Orthoptera or Saltatoria, Psocoptera, Thysanoptera and Zygentoma (= Thysanura) in plant protection.
[0067] [0067] More preferable is the use of the compounds of formula (I), (II), (II '), (IIa) and (IIa') in the control of Agriotes linneatus, Agriotes mancus, Anthonomus grandis, Anthonomus pomorum, Ceutorrhynchus assimilis , Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Diabrotica speciose, cucumeris Epitrix, Leptinotarsa decemlineata, oryzophilus Lissorhoptrus, Meligethes aeneus, Phaedon cochleariae, Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Sternechus paludatus Ceratitis capitate, Cerastium comatum, Chamaepsila rosae, Dacus ciliates, Delia antiqua, Deliarosia, radia, Melia, Delia plata, Delia plata Liriomyza huidobrensis, Liriomyza sativae, Rhagoletis cerasi, Rhag oletis indifferens, Acyrthosiphon pisum, Amrasca biguttula, Aonidiella aurantii, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletomi, Aphis niddletoni, Aphis niddletoni, Aphis niddletoni, Aphis niddletoni, Aphis niddletoni, Aphis niddletoni, Aphis niddletoni, Aphis , Aphis viburniphila, Bemisia tabaci, Brevicoryne brassicae, Cacopsylla pyri, Diaphorina citri, Dysaphis plantaginea, Eriosoma lanigerum, Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensiysi, Lipaphisalis, Lipapis cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nephotettix cincticeps, Nasonovia ribisnigri, Nephotettix nigropictus, Nilaparvata lugens, Pemphigus bursarium, Planococcus citri, Planococusisiotis, Perichosipis, Quadra Dichelops furcatus, Dichocrocis sp., Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Idioscopus clypealis, Lygus elisus, Lygus hesperus, Lygus lineolaris, Nezara viridula, Piezodorus guildinii, Sogatella furcifera, Adoxophyes orana, Agrotis et arg is Agr Agr Agr Agr Agr Agr Agr Agr Agr Agr Agr Agr Agr, Agrotis Chilo plejadellus, Chilo suppressalis, Chrysodeixis chalcites, Cnaphalocrocis medinalis, Cydia nigricana, Cydia pomonella, Diaphania hyalinata, Diaphania nitidalis, Diatraea saccharalis, Elasmopalpus lignosellus, Heliciaspa, Helixpa, Molecule, Helicopter, ambigella, Graphite undalis, Leucinodes orbonalis, Lobesia botrana, Mamestra brassicae, Ostrinia nubilalis, Pandemis heparana, Paralobesia viteana, Pectinophora gossypiella, Perileucoptera coffeella,
[0068] [0068] Particularly preferred is the use of the compounds of formula (I), (II), (II '), (IIa) and (IIa') in the control of Agriotes linneatus, Anthonomus grandis, Diabrotica balteata, Diabrotica barberi, Diabrotica virgifera virgifera, Diabrotica virgifera zea, Leptinotarsa decemlineata, Meligethes aeneus, Phaedon cochleariae, Cydia pomonella, Chilo suppressalis,; Elasmopalpus lignosellus, Helicoverpa armigera, Helicoverpa zea, Ostrinia nubilalis, Plutella xylostella, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Tuta absoluta, Aphis glycines, Metopolophium dirhodium, Rhopalosughilapata, Rhopalosiphumi padi; Nephotettix cincticeps, Nezara viridula, Dichelops furcatus, Euschistus heros, Lygus Hesperus in plant protection.
[0069] [0069] Very particularly preferred is the use for the control of Phaedon cochlearia in plant protection.
[0070] [0070] Very particularly preferred is the use for the control of Diabrotica balteata and plant protection.
[0071] [0071] Very particularly preferred is the use for the control of Spodoptera frugiperda in plant protection.
[0072] [0072] Very particularly preferred is the use for the control of Aphis gossypii in plant protection.
[0073] [0073] Very particularly preferred is the use for the control of Myzus persicae in plant protection.
[0074] [0074] Very particularly preferred is the use for the control of Tetranychus urticae in plant protection.
[0075] [0075] Very particularly preferred is the use for the control of Nilaparvata lugens in plant protection.
[0076] [0076] Very particularly preferred is the use for the control of Nezara viridula in plant protection.
[0077] [0077] Another matter of the invention is the use of a compound or a salt of formula (I), (II), (II '), (IIa) and (IIa') in vector control, in which the host is the human body.
[0078] [0078] Another subject of the invention is the vector control method in which a compound or a salt of formula (I), (II), (II '), (IIa) and (IIa') is left to act on the vectors and / or in their habitat, where the host is the human body, excluding methods of treating the human body.
[0079] [0079] As used in this application, the term "C1-C6alkyl" refers to a linear or branched monovalent saturated aliphatic chain of one to six carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, t- butyl, among others.
[0080] [0080] Likewise, the term "C1-C3alkyl" includes methyl, ethyl, isopropyl, among others.
[0081] [0081] As used in this application, the term "C1-C6haloalkyl" refers to a C1-C6alkyl moiety substituted with one or more halogen atoms that can be the same or different. Examples include trifluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 3,3,3-trifluoropropyl, 4-chlorobutyl, among others.
[0082] [0082] Likewise, the term "C1-C3haloalkyl" includes trifluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 3,3,3-trifluoropropyl, among others.
[0083] [0083] As used in this application, the term "C1-C3haloalkylsulfanyl" refers to a C1-C3haloalkyl moiety bonded by a sulfur atom.
[0084] [0084] As used in this application, the term "C3-C4cycloalkyl '' refers to cyclopropyl or cyclobutyl.
[0085] [0085] As used in this application, the term "C3-C4cycloalkyl-C1-C2alkyl-" refers to a C3-C4cycloalkyl linked by a C1-C2alkyl chain.
[0086] [0086] As used in this application, the term "C2-C6alkenyl" refers to a straight or branched alkenyl chain having two to six carbon atoms and a double bond, for example, ethylene, prop-1-enyl, but -2-enila, among others.
[0087] [0087] As used in this application, the term "C2-C6haloalkenyl '' refers to a C2-C6alkenyl moiety substituted with one or more halogen atoms that can be the same or different.
[0088] [0088] As used in this application, the term "C2-C6alkynyl" refers to a straight or branched alkynyl chain having two to six carbon atoms and a triple bond, for example, ethynyl, prop-2-inyl, but -3-inila, among others.
[0089] [0089] As used in this application, the term "C2-C6haloalkynyl" refers to a C2-C6alkynyl moiety substituted with one or more halogen atoms that can be the same or different.
[0090] [0090] As used in this application, the term "halo" 'refers to a chlorine, bromine, iodine or fluorine atom.
[0091] [0091] As used in this application, the term "C1-C3alkoxy" refers to a straight or branched alkyl chain having from 1 to 3 carbon atoms attached to an oxygen atom, for example, ethoxy, propoxy, ter-butoxy , among others.
[0092] [0092] As used in this application, the term "C1-C3haloalkoxy" refers to a C1-C3alkoxy moiety substituted with one or more halogen atoms that can be the same or different. Examples include trifluoromethoxy, 2-fluoroethoxy, 3-fluoropropoxy, 3,3,3-trifluoropropoxy, 4-chlorobutoxy, among others. Isomers
[0093] [0093] Depending on the nature of the substituents, the compounds of formula (I) can be in the form of geometric and / or optically active isomers or mixtures of the corresponding isomers in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Therefore, the invention encompasses both pure stereoisomers and any mixture of these isomers. Methods and uses
[0094] [0094] The invention relates to methods for the control of animal pests, in which compounds of formula (I) are left to act on the animal pests and / or their habitat. The control of animal pests is preferably carried out in agriculture and forestry, and in the protection of materials. Preferably methods for surgical or therapeutic treatment of the human or animal body and diagnostic methods performed on the human or animal body are excluded.
[0095] [0095] The invention also relates to the use of the compounds of formula (I) as pesticides, in particular as crop protection agents.
[0096] [0096] In the context of this application, the term "pesticide" in each case may also always include the term "crop protection agent".
[0097] [0097] The compounds of formula (I), which have good tolerance to plants, toxicity conducive to homeotherms and satisfactory compatibility with the environment, are suitable for protecting plants and plant organs against agents that cause biotic and abiotic stress, to increase crop yields, to improve the quality of harvested material and to control animal pests,
[0098] [0098] The compounds of formula (I) can preferably be used as pesticides. They are active against normally sensitive and resistant species and against all some stages of development. The above-mentioned pests include: pests of the Arthropoda phylum, in particular of the Arachnida class, for example, Acarus spp., For example, Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., For example, Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., for example, Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioides spp., Chorioptes sp. Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., For example, Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., For example, Eutetranychus banksi, Eriophyes spp., For example, Eriophyes pyri, destructor, Hempy, destructor, Glycyphag for example, Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., by and example, Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonysschchchpich, Panchischchischchpich, Panchischpich, Panchischpich, Panchischpich, Panchpisch, spich. ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneparsonus, Steneotarson. confusus, Tarsonemus pallidus, Tetranychus spp., for example, Tetranychus canadensis,
[0099] [0099] The compounds of formula (I) can also be used, in certain concentrations or rates of application, as herbicides, protectors, growth regulators or agents to improve the properties of plants, such as microbicides or gametocides, for example, as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (organisms similar to mycoplasma) and RLO (organisms similar to bacteria of the genus rickettsia). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds. Formulations
[00100] [00100] The present invention also relates to formulations and forms of use prepared therefrom as pesticides, for example, liquids for soaking, dripping and spraying, comprising at least one compound of formula (I). In some cases, the forms of use include other pesticides and / or adjuvants that improve their action, such as penetrants, for example, vegetable oils, for example, rapeseed oil, sunflower oil, mineral oils, for example, paraffin oils , alkyl esters of vegetable fatty acids, for example, rapeseed oil methyl ester or soy oil methyl ester, or alkanol alkoxylates and / or spreading agents, for example, alkylsiloxanes and / or salts, for example, ammonium salts or organic or inorganic phosphonium, for example, ammonium sulphate or diamonium hydrogen phosphate, and / or retention promoters, for example, dioctyl or hydroxypropyl guar polymers and / or humectants, for example, glycerol and / or fertilizers , for example, fertilizers containing ammonium, potassium or phosphorus.
[00101] [00101] Usual formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), water emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-soluble granules ( WG), granules (GR) and capsule concentrates (CS); these and other possible types of formulation are described, for example, by Crop Life International and emin Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN:
[00102] [00102] These are preferably formulations or forms of use that include auxiliaries, for example, diluents, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectors, biocides, thickeners and / or other auxiliaries, for example, adjuvants . An adjuvant in this context is a component that enhances the biological effect of the formulation, without the component itself having any biological effect. Examples of adjuvants are agents that favor retention, spreading, and attachment to the surface of the leaves, or penetration.
[00103] [00103] These formulations are prepared in a known manner, for example, by mixing the compounds of formula (I) with auxiliaries such as, for example, diluents, solvents and / or solid carriers and / or other auxiliaries such as, for example , surfactants. The formulations are prepared in suitable facilities or even before or during application.
[00104] [00104] The auxiliaries used can be substances suitable for imparting special properties, such as certain physical, technical and / or biological properties, to the formulation of the compounds of formula (I), or to the forms of use prepared from those formulations (for example , ready-to-use pesticides such as spraying liquids or seed ground products).
[00105] [00105] Suitable diluents are, for example, water, polar and non-polar organic chemical liquids, for example, from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which, if appropriate, they can also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, unsubstituted and substituted amines, amides, lactams (such as N -alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), carbonates and nitriles.
[00106] [00106] If the diluent used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example, mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, carbonates such as propylene carbonate , butylene carbonate, diethyl carbonate or dibutyl carbonate, or nitriles such as acetonitrile or propanonitrile.
[00107] [00107] In principle, it is possible to use all suitable solvents. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane, paraffins, petroleum fractions, mineral oils and vegetables, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulfoxide, carbonates such such as propylene carbonate, butylene carbonate, diethyl carbonate or dibutyl carbonate, nitriles such as acetonitrile or propanonitrile, and also water.
[00108] [00108] In principle, it is possible to use all suitable carriers. Useful carriers include especially: for example, ammonium salts and ground natural minerals such as kaolin, clays, talc, chalk, quartz, atapulgite, montmorillonite or diatomaceous earth; and ground synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Useful granule carriers include: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic flours, as well as granules of organic material such as sawdust, paper, bark coconut, corn cob and tobacco stalk.
[00109] [00109] Diluents or liquefied gas solvents can also be used. Particularly suitable diluents or carriers are those that are gaseous at room temperature and at atomic pressure, for example, propellant gases for aerosols, such as hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
[00110] [00110] Examples of emulsifiers and / or antifoams, dispersants or wetting agents with ionic or nonionic properties, or mixtures of these surfactants, are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensated oxide salts ethylene with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), isethionate derivatives, phosphoric esters of alcohols or polyethoxylated phenoxys, polyol fatty esters, and derivatives of compounds containing sulphates, sulphonates and phosphates, for example, alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates, protein hydrolysates, residual lignosulphite and methyl cellulose liquors. The presence of a surfactant will be advantageous if one of the compounds of formula (I) and / or one of the inert carriers is insoluble in water and when the application occurs in water.
[00111] [00111] Dyes such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metallic phthalocyanine dyes, and nutrients and nutrients can be used -traction such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts as additional auxiliaries in the formulations and the forms of use derived from them.
[00112] [00112] Additional components can be stabilizers, such as low temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve chemical and / or physical stability. Sparkling or defoamer may also be present.
[00113] [00113] Adherents such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or nets, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or even natural phospholipids such as cephalins and lecithins and synthetic phospholipids can also be present as additional auxiliaries in the formulations and in the forms of use derived from them. Other possible auxiliaries are mineral and vegetable oils.
[00114] [00114] Optionally, other auxiliaries may be present in the formulations and in the forms of use derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention promoters, stabilizers, scavengers, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) can be combined with any solid or liquid additive commonly used for formulation purposes.
[00115] [00115] Useful retention promoters include all substances that reduce dynamic surface tension, for example, dioctyl sulfosuccinate, or that increase viscoelasticity, for example, hydroxypropyl polymers.
[00116] [00116] Suitable penetrants in the present context are all those substances that are normally used to improve the penetration of active agrochemical compounds in plants. In this context, penetrants are defined by their ability to penetrate from the application liquid (usually aqueous) and / or the spray coating on the plant cuticle and thus increase the mobility of active compounds in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut acid ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, for example, rapeseed oil methyl ester or soy oil methyl ester, fatty amine alkoxylates, for example, sebumamine ethoxylate (15), or ammonium and / or phosphonium salts, for example, ammonium sulphate or diamonium hydrogen phosphate.
[00117] [00117] Preferably formulations comprise between 0.00000001 and 98% by weight of the compound of formula (I) or, particularly preferably preference, between 0.01% and 95% by weight of the compound of formula (I), more preferably between 0.5% and 90% by weight of the compound of formula (I), based on the weight of the formulation.
[00118] [00118] The content of the compound of formula (I) in the forms of use prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of compound of formula (I) in the forms of use generally varies between 0.00000001 and 95% by weight of the compound of formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the form of use. The compounds are used in a usual manner appropriate to the forms of use. Mixtures
[00119] [00119] The compounds of formula (I) can also be used as a mixture with one or more fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficial species, herbicides, fertilizers, bird repellents, phytotonics, sterilizers, protectors, semi-chemicals and / or plant growth regulators suitable for, for example, thus broadening the spectrum of action, prolonging the duration of action, increasing the rate of action, preventing repulsion or preventing the development of resistance. In addition, such combinations of active compounds can increase plant growth and / or tolerance to abiotic factors, for example, high or low temperatures, drought or a high water content or high soil salinity. It is also possible to improve flowering and fruiting performance, optimize germination capacity and root development, facilitate harvesting and increase yield, influence ripeness, improve the quality and / or nutritional value of harvested products, prolong life useful and / or improve the processability of the harvested products.
[00120] [00120] In addition, the compounds of formula (I) may be present in a mixture with other active or semi-chemical compounds such as attractants and / or repellents for birds and / or activators and / or growth regulators and / or plant fertilizers . Likewise, the compounds of formula (I) can be used to improve the properties of plants such as, for example, the growth, yield and quality of the harvested material.
[00121] [00121] In a particular embodiment according to the invention, the compounds of formula (I) are present in formulations or the forms of use prepared from these formulations are present in a mixture with other compounds, preferably those described above.
[00122] [00122] If one of the compounds mentioned below can occur in different tautomeric forms, these forms are also included although not explicitly mentioned in each case. In addition, all participants in specified mixtures may optionally, if their functional groups so permit, form salts with suitable bases or acids. Preferred insecticides / acaricides / nematicides for mixtures
[00123] [00123] The active compounds identified by their common names in this application are known and are described, for example, in the pesticide manual ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or can be found on the Internet (by example, http://www.alanwood.net/pesticides). The classification is based on the IRAC Mode of Action Classification Scheme
[00124] [00124] The active compounds specified in this application by their common name are known and are described, for example, in The Pesticide Manual (16th Ed.British Crop Protection Council) or can be found on the internet (for example, www.alanwood.net / pesticides).
[00125] [00125] All participants of the mentioned fungicidal mixtures belonging to classes (1) to (15) may, if their functional groups permit, optionally form salts with suitable bases or acids. All participants in mixtures belonging to classes (1) to (15) may include tautomeric forms, where applicable. 1) Ergosterol biosynthesis inhibitors, for example, (1,001) cyproconazole, (1,002) diphenoconazole, (1,003) epoxiconazole, (1,004) fenhexamid, (1,005) fenpropidine, (1,006) fenpropimorph, (1,007) fenpirazamine, (1.007) flupyazamine, , (1,009) flutriafol, (1,010) imazalil, (1,011) imazalyl sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazol, (1,016) prochloraz, (1,017) propiconazole, (1,018) prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetraconazole, (1,023) triadimenol, (1,024) tridemorph, (1,025) triticonazole, (1,026) (1R, 2S, 5S) - 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) - cyclo-pentanol, (1,027) (1S, 2R, 5R) -5 - (4-chlorobenzyl) -2- (chloromethyl) -2- methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1,028) (2R) -2- (1-chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazole-1-
[00126] [00126] The compounds of formula (I) can be combined with biological pesticides.
[00127] [00127] Biological pesticides comprise in particular bacteria, fungi, yeasts, extracts and plant products formed by microorganisms, including proteins and secondary metabolites.
[00128] [00128] Biological pesticides comprise bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
[00129] [00129] Examples of such bacteria that are employed or can be used as biological pesticides are: Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus, strain I- 1582 (Access CNCM number I-1582) or Bacillus pumilus, in particular strain GB34 (Access No. ATCC 700814) and strain QST2808 (Access No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Access No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14) , strain AM65-52
[00130] [00130] Examples of fungi and yeasts that are employed or can be used as biological pesticides are: Beauveria bassiana, in particular strain ATCC 74040, Coniothyrium minitans, in particular strain CON / M / 91-8 (Access No. DSM-9660) , Lecanicillium spp., In particular HRO LEC 12 strain, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular F52 strain (DSM3884 / ATCC 90448), Metschnikowia ceucpa NRucticola, in particular - 30752, Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus cepa 251 (AGAL 89/030550), Talaromyces flavus, in particular strain V117b, Trichoderma atroviride, in particular strain SC1 (Accession number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Access CNCM number I-952).
[00131] [00131] Examples of viruses that are employed or can be used as biological pesticides are: Adoxophyes orana granulose virus (summer fruit tortrix) (GV), Cydia pomonella granulation virus (carpocapsa) (GV), nuclear polyhedrosis of Helicoverpa armigera (cotton caterpillar) (NPV), Spodoptera exigua mNPV (military beet caterpillar), Spodoptera frugiperda mNPV (autumn military caterpillar), NPV of
[00132] [00132] Also included are bacteria and fungi which are added as an 'inoculant' for plants or parts of plants or plant organs and which, due to their particular properties, promote plant growth and plant health. Examples that can be mentioned are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gumpora spp., Or Gumpora spp. Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., In particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spomy.
[00133] [00133] Examples of plant extracts and products formed by microorganisms including proteins and secondary metabolites that are employed or can be used as biological pesticides are: Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum , chitin, Armor-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem ™ Insecticide", rotenone, ryania / rianodina, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, in particular powdered rapeseed or powdered mustard. Protectors as mixing components
[00134] [00134] The compounds of formula (I) can be combined with protectors such as, for example, benoxacor, cloquintocet (-mexyl), ciometrinyl, cyprosulfamide, dichlormide, phenclorazole (-ethyl), phenclorin, flurazole, fluxophenin, furilazole, isoxadifene (-ethyl), mefenpyr (-diethyl),
[00135] [00135] All plants and parts of plants can be treated according to the invention. In this application, plants are understood to mean all plants and parts of plants such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants), for example, cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, beets, sugar cane, tomatoes, peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage) and other vegetable species, cotton, tobacco, rapeseed, and also fruit plants (with fruits apples, pears, citrus fruits and vines). Tillage plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or by combinations of these methods, including transgenic plants and plant varieties that may or may not be protected by varietal property rights. . Plants are understood to mean all stages of development, such as seeds, seedlings, young (immature) plants to mature plants. Plant parts are understood to mean all plants and plant organs above and below ground, such as buds, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruit bodies, fruits and seeds , and also tubers, roots and rhizomes. Plant parts also include harvested plants or parts and material of vegetative and generative propagation of harvested plants, for example, seedlings, tubers, rhizomes, seedlings and seeds.
[00136] [00136] The treatment according to the invention of plants and parts of plants with compounds of formula (I) is carried out directly or by allowing the compounds to act in the surroundings, in the environment or in the storage area by traditional treatment methods, for example example, by immersion, spraying, evaporation, nebulization, spreading, deposition, injection and, in the case of propagating material, in particular in the case of seeds, also by applying one or more films.
[00137] [00137] As mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, species of wild plants and plant cultivars are treated, or those obtained by conventional biological breeding methods, such as crossing or fusion of protoplasts, and also parts thereof. In another preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods are treated, if appropriate in combination with conventional methods (genetically modified organisms), and parts thereof. The term "parts" or "parts of plants" has already been explained above. The invention is used with particular preference to treat plants of the respective commercially common cultivars or those that are in use. Plant cultivars are understood to mean plants with new properties ("traits") that have been obtained by conventional reproduction, mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes. Transgenic plant, seed treatment and integration events
[00138] [00138] Transgenic plants or plant cultivars (those obtained by genetic engineering) that are preferably treated according to the invention include all plants that, through genetic modification, have received genetic material that confers useful properties ("traits") and advantageous to plants.
[00139] [00139] The treatment of plants and plant parts with the compounds of formula (I) is carried out directly or by action on their surroundings, habitat or storage area by usual treatment methods, for example, immersion, spraying, atomization, irrigation , evaporation, dusting, misting, spreading, foaming, deposition, spreading, injection, watering (drenching), drip irrigation and, in the case of propagating material, in particular in the case of seeds, still as a powder for dry treatment of seeds, a solution for treating seeds with liquid, a water-soluble powder for treatment with paste, by incrustation, by coating with one or more films, etc. It is also possible to apply the compounds of formula (I) by the ultra-low volume method or to inject the application formation or the compounds of formula (I) into the soil.
[00140] [00140] A preferred direct treatment of plants is foliar application, that is, the compounds of formula (I) are applied to the foliage, where the frequency of treatment and the application rate must be adjusted according to the level of infestation by pest in question.
[00141] [00141] In the case of systemically active compounds, the compounds of formula (I) also have access to plants through the root system. The plants are then treated by the action of the compounds of formula (I) in the plant's habitat. This can be done, for example, by soaking, or by mixing with the soil or the nutrient solution, that is, the location of the plant (for example, soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I) , or by application to the ground, that is, the compounds of formula (I) according to the invention are introduced in solid form (for example, in the form of granules) at the site of the lantas, or by drip application (generally also called "chemigation"), that is, the liquid application of the compounds of formula (I) according to the invention from surface or underground drip tubes for a certain period of time together with varying amounts of water in defined locations in the vicinity of the plants. In the case of rice crops, this can also be done by introducing a dose of the compound of formula (I) in a solid application form (for example, as granules) in a pond. Seed treatment
[00142] [00142] The control of animal pests through the treatment of plant seeds has been known for a long time and is the object of constant improvements. However, seed treatment generates a series of problems that cannot always be satisfactorily solved. Therefore, it is desirable to develop methods for the protection of seeds and germinating plants that dispense, or at least considerably reduce, the additional application of pesticides during storage, after sowing or after the emergence of plants. It is also desirable to optimize the amount of active compound used in order to provide the ideal protection for seeds and plants in germination against animal pests, but without damaging the plants themselves by the active compound used. In particular, seed treatment methods also take into account the intrinsic insecticidal or nematicidal properties of resistant or pest-tolerant transgenic plants in order to obtain the ideal protection of the seeds and also of the germinating plants with a minimum of pesticides being employed.
[00143] [00143] The present invention, therefore, also relates in particular to a method for the protection of germinating seeds and plants, against pests, by treating the seeds with one of the compounds of formula (I). The method according to the invention for protecting germinating seeds and plants against pest attack further comprises a method in which the seeds are treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixing component. It also comprises a method in which the seeds are treated at different times with a compound of formula (I) and a mixing component.
[00144] [00144] The invention also relates to the use of the compounds of formula (I) for the treatment of seeds to protect the resulting seeds and plants against animal pests.
[00145] [00145] In addition, the invention also relates to seeds that have been treated with a compound of formula (I) according to the invention in order to provide protection against animal pests. The invention also relates to seeds that have been treated simultaneously with a compound of formula (I) and a mixing component. The invention also relates to seeds that have been treated at different times with a compound of formula (I) and a mixing component. In the case of seeds that have been treated at different times with a compound of formula (I) and a mixing component, the individual substances may be present in the seeds in different layers. Here, the layers comprising a compound of formula (I) and mixing components can optionally be separated by an intermediate layer. The invention also relates to seeds to which a compound of formula (I) and a mixing component have been applied as a component of a coating or as an additional layer or layers in addition to a coating.
[00146] [00146] Furthermore, the invention relates to the fact that the seeds, after treatment with a compound of formula (I), are subjected to a coating process with a film to prevent abrasion of the seeds by dust.
[00147] [00147] One of the advantages observed with a compound of formula (I) with systemic action is the fact that, through the treatment of the seeds, not only the seeds themselves, but also the plants resulting from them are, after emergence, protected against animal pests. In this way, the immediate treatment of the crop at the moment of sowing or right after it can be eliminated.
[00148] [00148] One should consider as an advantage the fact that by treating the seeds with a compound of formula (I), the germination and emergence of the treated seeds can be improved.
[00149] [00149] The fact that the compounds of formula (I) can also be used in particular in transgenic seeds should also be considered advantageous.
[00150] [00150] Furthermore, the compounds of formula (I) can be used in combination with compositions or compounds of signaling technology, leading to better colonization by symbionts such as, for example, rhizobia, mycorrhizae and / or bacteria or endophytic fungi, and / or optimized nitrogen fixation.
[00151] [00151] The compounds of formula (I) are suitable for the protection of seeds of any variety of plant that is used in agriculture, greenhouses, forests or horticulture. In particular, these can be cereal seeds (for example, wheat, barley, rye, millet and oats), corn, cotton, soy, potato, sunflower, coffee, tobacco, canola, rapeseed, forage (for example, beet and fodder ), peanuts, vegetables (for example, tomatoes, cucumbers, beans, cruciferous vegetables, onions and lettuce), fruit plants, lawns and ornamental plants. The treatment of cereal seeds (such as wheat, barley, rye and oats), corn, soybeans, cotton, canola, rapeseed, vegetables and rice is of particular importance.
[00152] [00152] As already mentioned above, the treatment of transgenic seeds with a compound of formula (I) is also of particular importance. These can be seeds of plants that, as a rule, comprise at least one heterologous gene that controls the expression of a polypeptide with properties, in particular, insecticides and / or nematicides. The heterologous genes in transgenic seeds may originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seeds that comprise at least one heterologous gene originating from Bacillus sp. Particularly preferred is a heterologous gene derived from Bacillus thuringiensis.
[00153] [00153] In the context of the present invention, the compound of formula (I) is applied to the seed. Preferably, the seed is treated at a stage where it is sufficiently stable to avoid damage during treatment. In general, the seed can be treated at any time between harvest and sowing. The seed normally used was separated from the plant and released from cobs, peels, stems, films, hair or the flesh of the fruit. For example, it is possible to use seeds that have been harvested, washed and dried to a moisture content that allows their storage. Alternatively, it is also possible to use seeds that, after drying, have been treated with, for example, water and then dried again, for example, primed. In the case of rice seeds, it is also possible to use seeds that have been macerated, for example, in water up to a certain stage of the rice embryo ('pigeon breast stage'), stimulating germination and a more uniform emergence.
[00154] [00154] When treating the seeds, it should generally be observed that the amount of compound of formula (I) applied to the seeds and / or the amount of other additives is chosen so that the germination of the seeds is not adversely affected , or that the resulting plants are not damaged. This must be guaranteed particularly in the case of active compounds that can have phytotoxic effects at certain rates of application.
[00155] [00155] In general, the compounds of formula (I) are applied to the seeds in a suitable formulation. Formulations and processes suitable for seed treatment are already known to the person skilled in the art.
[00156] [00156] The compounds of formula (I) can be converted into usual seed coating formulations, such as solutions, emulsions, suspensions, powders, foams, pastes or other coating compositions, and also ULV formulations.
[00157] [00157] These formulations are prepared in a known manner, by mixing the compounds of formula (I) with usual additives such as, for example, usual diluents and also solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
[00158] [00158] Dyes that can be present in seed coating formulations that can be used according to the invention are all dyes that are usual for this purpose. It is possible to use pigments, which are moderately soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.
[00159] [00159] Useful wetting agents that can be present in seed coating formulations that can be used according to the invention are all substances that promote wetting and that are conventionally used for the formulation of agrochemically active compounds. Preference is given to the use of alkylnaphthalenesulfonates, such as diisopropyl- or diisobutylnaphthalenesulfonates.
[00160] [00160] Dispersants and / or emulsifiers that may be present in seed coating formulations that can be used according to the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of agrochemical active ingredients. Preference is given to the use of nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable non-ionic dispersants include in particular block polymers of ethylene oxide / propylene oxide, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and the phosphate or sulfate derivatives thereof. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate / formaldehyde condensates.
[00161] [00161] Defoamers that can be present in seed coating formulations that can be used according to the invention are all foam inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Preference is given to the use of silicone and magnesium stearate defoamers.
[00162] [00162] Preservatives that can be present in seed coating formulations that can be used according to the invention are all substances that can be used for this purpose in agrochemical compositions. Examples include dichlorophene and hemiformal benzyl alcohol.
[00163] [00163] Secondary thickeners that can be present in seed coating formulations that can be used according to the invention are all substances that can be used for this purpose in agrochemical compositions. Cellulose derivatives, derivatives of acrylic acid, xanthan, modified clays and finely divided silica are preferred.
[00164] [00164] Secondary thickeners that can be present in seed coating formulations that can be used according to the invention are all substances that can be used for this purpose in agrochemical compositions. Cellulose derivatives, derivatives of acrylic acid, xanthan, modified clays and finely divided silica are preferred.
[00165] [00165] Adhesives that can be present in seed coating formulations that can be used according to the invention are all the usual binders that can be used in seed treatment products. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose can be mentioned as preferred.
[00166] [00166] Gibberellins which may be present in seed coating formulations which can be used according to the invention are preferably gibberellins A1, A3 (= gibberellic acid), A4 and A7; gibberellic acid is especially preferably used. Gibberlins are already known (cf. R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", vol. 2, Springer Verlag, 1970, pp. 401-412).
[00167] [00167] Seed coating formulations that can be used according to the invention can be used to treat a wide variety of different types of seed either directly or after previous dilution in water. For example, concentrates or preparations that can be obtained from them by dilution in water can be used to treat cereal seeds, such as wheat, barley, rye, oats, and triticale, as well as corn, rice, rapeseed, peas, beans, cotton, sunflower, soy and forage, or a wide variety of seeds of different vegetables. Seed coating formulations that can be used according to the invention, or the diluted forms of use thereof, can also be used to treat seeds from transgenic plants.
[00168] [00168] For seed treatment with the seed coating formulations that can be used according to the invention, with the forms of use prepared from them by adding water, all mixing units normally used for the treatment of seeds are useful. Specifically, the seed coating procedure is to place the seeds in a mixer, operated intermittently or continuously, add the particular desired amount of seed coating formulations, either as is or after prior dilution with water, and mix all until the formulation is evenly distributed over the seeds. If appropriate, this procedure is followed by a drying operation.
[00169] [00169] The application rate of the seed coating formulations that can be used according to the invention can vary within a relatively wide range. It is dictated by the specific content of compounds of formula (I) in the formulations and by the seeds. Application rates of the compound of formula (I) generally vary between 0.001 and 50 g per kilo of seed, preferably between 0.01 and 15 g per kilo of seed. Vector control
[00170] [00170] The compounds of formula (I) can also be used in vector control. For the purposes of the present invention, a vector is an arthropod, in particular an insect or arachnid, capable of transmitting pathogens such as, for example, viruses, worms, single-celled organisms and bacteria from a reservoir (plant, animal, human, etc.) for a host. Pathogens can be transmitted either mechanically (eg, trachoma by non-biting flies) to a host, or by injection (eg, malaria parasites by mosquitoes) into a host.
[00171] [00171] Examples of vectors and the diseases or pathogens they transmit are: 1) Mosquitoes - Anopheles: malaria, filariasis; - Culex: Japanese encephalitis, other viral diseases, filariasis, transmission of other worms; - Aedes: yellow fever, dengue fever, other viral diseases, filariasis; - Simuliidae: transmission of worms, in particular Onchocerca volvulus; - Psychodidae: transmission of leishmaniasis 2) Lice: skin infections, epidemic typhus; 3) Fleas: plague, endemic typhus, basket; 4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases; 5) Mites: mites, epidemic typhus, smallpox for rickettsia, tularemia, Saint Louis encephalitis, tick-borne encephalitis (TBE), Crimean – Congo hemorrhagic fever, borreliosis; 6) Ticks: borelioses such as Borrelia burgdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesiosis (Babesia canis canis), ehrlichiosis.
[00172] [00172] Examples of vectors in the context of the present invention are insects, for example, aphids, flies, cicadas or thrips, which are capable of transmitting viruses from plants to plants. Other vectors capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.
[00173] [00173] Other examples of vectors in the context of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example, A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia, pests, fleas, flies, mites and ticks capable of transmitting pathogens to animals and / or humans.
[00174] [00174] Vector control is also possible if the compounds of formula (I) are resistance breakers.
[00175] [00175] The compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Therefore, another aspect of the present invention is the use of compounds of formula (I) for vector control, for example, in agriculture, horticulture, gardens and leisure areas, and also in the protection of materials and materials. stored products. PREPARATION OF COMPOUNDS
[00176] [00176] The compounds of formula I, II ', II, II'a and IIa can be prepared by the person skilled in the art by means of the following techniques and procedures recognized in the literature.
[00177] [00177] More specifically, compounds of formula I, II ', II, II'a and IIa can be prepared as shown on page 17, line 15 through page 24, line 7 of WO 2017/192385 and in schemes 1 - 7 of WO 2017/192385.
[00178] [00178] The 3-Chloro-5 - [(trifluoromethyl) sulfanyl] benzamides shown in example I-107 (scheme 8) can be synthesized in a manner analogous to that described in Angew. Chem. Int. Ed. 2012, 51, 2492 -
[00179] [00179] Scheme 9 illustrates the preparation of 3-haloalkyl triazoles shown, for example, in example I-131. In a first step, an amide hydrazine is formed in the manner described in the EP document
[00180] [00180] To 4.30 g of (30.00 mmol) 5-chloro-2-hydrazinyl-pyridine in methanol (30 mL) was added 7.74 g (42.00 mmol) of 2.2 ethyl acid ester , 2-trifluoro-etanimid, and the reaction mixture was stirred at room temperature for one night. The solvent was evaporated and the residue was then stirred with n-hexane (30 ml) and ethyl acetate (3 ml). The brownish precipitate was separated and dried to obtain 4.81 g (purity: 89.0%; yield: 59.8%) N '- (5-chloropyridin-2-yl) (trifluoro) ethane-hydrazonamide. Formula: C7H6ClF3N4 Molecular weight: 238.59 g / mol HPLC-MS (ESI Positiv): 239.0 (M + 1); Rt = 0.91; 0.93 min (instrument: LC-MS7)
[00181] [00181] To 596.5 mg (2.50 mmol) of (1Z) -N '- (5-chloropyridin-2-yl) (trifluoro) ethane-hydrazonamide in pyridine (10 mL), 594.1 mg was added (2.50 mmol) of (αS) -1,3-dihydro-α-methyl-1,3-dioxo- 2H-isoindol-2-acetyl chloride (see preparation of acid (αS) -1.3 -dihydro-α-methyl-1,3-dioxo-2H-isoindol-2-acetic (Pht-Ala-OH purchased from ABCR) and oxalyl chloride: Tetrahedron: Asymmetry, 21 (8), 936-942, 2010), and the reaction mixture was stirred at room temperature for one night. Then, a saturated NaHCO3 solution was added and the mixture was extracted with dichloromethane. The organic phase was separated, dried and the solvent was evaporated. The remaining solid residue was chromatographed with a cyclohexane / acetone gradient over silica gel to give 495.0 mg (purity: 96.8%; yield: 45.4%) of the title compound as a colorless solid. Formula: C18H11ClF3N5O2 Molecular weight: 421.76 g / mol HPLC-MS (ESI Positiv): 422.1 (M + 1); Rt = 1.50 min (instrument: LC-MS6) 13C-NMR with 1H dec. (CPD) (150 MHz, CD3CN, ppm) σ = 17.6 (H3C); 44.8 (CH); 119.1 (C-H, pyridinyl); 120.3 (F3C, triazolyl); 124.0 (2x C-H, phthalyl); 132.4 (2xC, phthalyl); 132.9 C-Cl, pyridinyl); 135.5 (2x C-H, phthalyl); 140.5 (C-H, pyridinyl); 147.8 (C-H, pyridinyl); 148.9 (C-N, pyridinyl); 153.1 (C, triazolyl), 158.2 (C, triazolyl); 168.0 (2x C = O, phthalyl). Step 3: (αS) -Methyl-1- (5-chloropyridin-2-yl) -1H-1,2,4-triazole-5-methanamine
[00182] [00182] A 440.0 mg (1.043 mmol) of 2 - [(1S) -1- [3- (trifluoromethyl) -1- (1- (5-chloropyridin-2-yl) -1H-1,2, 4-triazol-5-yl) ethyl] -1H-isoindol-1,3 (2H) -dione in ethanol (10 mL), 142.4 mg (1.565 mmol) of hydrazine hydrate was added, and the reaction mixture was heated to reflux. After 30 minutes, a colorless precipitate formed. The reaction mixture was stirred and heated to reflux for an additional hour, acetone (5 ml) was added and heating continued for an additional 30 minutes. The reaction mixture was concentrated and the solid residue was treated with ethanol. Then, the solvent was evaporated to give 190.0 mg (yield: 62.4%) of (αS) -methyl-1- (5-chloropyridin-2-yl) -1H-1,2,4-triazole- 5-methane amine, which was used in the N-acylation reaction (step 4) without purification. Formula: C10H9ClF3N5 Molecular weight: 291.66 g / mol HPLC-MS (ESI Positiv): 292.0 (M +); Rt = 0.52 min (wide) (instrument: LC-MS7) Step 4: 3-Chlorine-N - {(1S) -1- [1- (5-chloropyridin-2-yl) -3- (trifluoromethyl) -1H- 1,2,4-triazol-5-yl] ethyl} -5- (trifluoromethyl) benzamide
[00183] [00183] To 188.9 mg (0.648 mmol) (αS) -methyl-1- (5-chloro-2-pyridinyl) - 1H-1,2,4-triazole-5-methane amine, 150.0 were added mg (0.648 mmol) of 3-chloro-5- (trifluoromethyl) -benzoic acid, 108.8 mg (0.842 mmol) of N, N-diisopropylethylamine (Hünig's base) in N, N-dimethylformamide (DMF) (5 mL ), 296.6 mg (0.778 mmol) of [O- (7-azabenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate (HATU), and the reaction mixture was stirred at temperature environment for one night. The reaction mixture was concentrated and the solid residue was treated with dichloromethane and then extracted with a saturated solution of NaHCO3 and water. The organic phase was separated, dried and the solvent was evaporated. The remaining solid residue was chromatographed with a cyclohexane / acetone gradient over silica gel to give 230.0 mg (purity: 96.0%; yield: 68.4%) of the title compound. Formula: C18H11Cl2F6N5O Molecular weight: 498.20 g / mol HPLC-MS (ESI Positiv): 497.9 (M +), 498.9 (M + 1); Rt = 1.71 min
[00184] [00184] The compounds according to the invention described in Table 1 below are also preferred compounds of formula (I) according to the invention which are obtained according to the synthesis schemes described above or in WO 2017/192385 or from analogous to them. Table 1 Example Structure Example No. Structure No. I-01 I-02 I-03 I-04 I-05 I-06 I-07 I-08
[00185] [00185] The determination of [M + H] + or M- by LC-MS under acid chromatographic conditions was made with 1 ml of formic acid per liter of acetonitrile and 0.9 ml of formic acid per liter of Millipore water as eluents . The Zorbax Eclipse Plus C18 50 mm * 2.1 mm column was used. The column oven temperature was 55 ° C. Instruments: LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManager automatic classifier. Linear gradient 0.0 to 1.70 minutes from 10% acetonitrile to 95% acetonitrile, from 1.70 to 2.40 minutes constant 95% acetonitrile, flow 0.85 ml / min. LC-MS6 and LC-MS7: Agilent 1290 LC, Agilent MSD, HTS PAL automatic classifier. Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow 1.0 ml / min.
[00186] [00186] The determination of [M + H] + by LC-MS under neutral chromatographic conditions was done with acetonitrile and Millipore water containing 79 mg / l of ammonium carbonate as eluents. Instruments:
[00187] [00187] LC-MS4: Waters IClass Acquity with QDA mass spectrometer and automatic FTN classifier (Waters Acquity column 1.7 µm 50 mm * 2.1 mm, oven temperature 45 ° C). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow 0.7 ml / min.
[00188] [00188] LC-MS5: Agilent 1100 LC system with MSD mass spectrometer and HTS PAL automatic classifier (column: Zorbax XDB C18 1.8 µm 50 mm * 4.6 mm, oven temperature 55 ° C). Linear gradient 0.0 to 4.25 minutes from 10% acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95% acetonitrile, flow 2.0 ml / min.
[00189] [00189] The retention time indices were calculated in all cases according to the invention a homologous series of straight chain alkan-2-ones with 3 to 16 carbons where the index of the first alkanone was fixed at 300, the last alkanone in 1600, and those between these values were determined correspondingly by means of a linear interpolation between successive alkanones. NMR data from selected examples
[00190] [00190] The determination of 1H-NMR data was made using a 400 MHz Bruker Avance III spectrometer equipped with a 1.7 mm TCI test head, with tetramethylsilane as reference (0.00 ppm) and the measurements were usually registered from solutions in the CD3CN, CDCl3 or d6-DMSO solvents. Alternatively, a Bruker Avance III 600 MHz instrument equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz instrument equipped with a 5 mm TCI probe head were used for the measurements. In general, measurements were made with a probe head temperature of 24.85 ° C (298 K). Other measuring temperatures are explicitly mentioned. Peak NMR List Procedure
[00191] [00191] The 1H-NMR data of selected examples are presented as 1H-NMR peak ratios. The  values in ppm and the signal strength in parentheses are shown for each signal peak. The  - signal strength value pairs are separated by semicolons.
[00192] [00192] Therefore, the peak ratio of an example has the form: 1 (intensity1); 2 (intensity2); …… ..; i (intensityi); ……; n (intensity)
[00191] [00191] The intensity of sharp signals is correlated with the height of the signals in a printed material of a spectrum of 1H-NMR in cm and presents the real relations of the signal intensities. Several large signal peaks or the center of the signal and their relative strength compared to the most intense signal in the spectrum can also be shown.
[00192] [00192] Tetramethylsilane or the chemical deviation of the solvent in cases where the sample does not contain tetramethylsilane is used for a calibration of the chemical deviation for the 1H spectra. Therefore, the tetramethylsilane peak may appear in the 1 H-NMR peak ratio, but not necessarily.
[00193] [00193] The 1H-NMR peak ratios are equivalent to the classic 1H-NMR printouts and generally contain all of the peaks, which are also listed in the classic 1H-NMR interpretations.
[00194] [00194] In addition, they also show the signs of the solvents, stereoisomers of the compounds that are optionally the object of the invention, and / or impurity peaks, such as the classic 1H-NMR prints.
[00195] [00195] The 1H-NMR solvent signals, the tetramethylsilane signal and the water signal in the corresponding solvent are excluded from the relative intensity calibration because they can have very high intensity values.
[00196] [00196] On average, the peaks of the stereoisomers of the compounds according to the invention and / or the peaks of the impurities normally have a lower intensity than the peaks of the compounds according to the invention (for example, with a purity> 90 %).
[00197] [00197] Such stereoisomers and / or impurities may be typical for the specific preparation process. Therefore, the corresponding peaks can help to recognize the reproduction of the preparation process through the "fingerprints of the by-products".
[00198] [00198] An expert, who calculates the peaks of the target compounds by known methods (MestreC, ACD simulation, and also with empirically determined values), can determine the peaks of the target compounds as needed, using optionally additional intensity filters . This determination would be similar to researching the usual peak in classical 1H-NMR interpretations.
[00199] [00199] The solvent used can be found in the JCAMP file with the parameter "solvent", the frequency of the spectrometer with "observed frequency" and the type of spectrometer with "spectrometer / data system".
[00200] [00200] The 13C-NMR data are presented in a similar way to the 1H-NMR data as peak ratios from the broadband decoupled 13C-NMR spectra. The 13C-NMR and tetramethylsilane solvent signals are excluded from the relative intensity calibration because these signals can have very high intensity values.
[00201] [00201] Further details on the description of NMR data with peak ratios are presented in the publication "Citation of RMN Peaklist Data within Patent Applications" from Research Database Number 564025. Table 2 No. Structure NMR peak ratio I -06 I-06: 1H-NMR (600.1 MHz, CD3CN): δ = 8.4399 (3.6); 8.4324 (3.7); 8.0641 (12.1); 8.0473 (3.8); 8.0367 (2.1); 8.0341 (2.2); 8.0089 (5.9); 7.9992 (2.3); 7.9914 (2.3); 7.9399 (1.1); 7.9274 (2.1); 7.9160 (1.2); 7.9141 (1.2); 7.8496 (5.3); 7.8360 (4.6); 7.7683 (6.2); 7.7055 (2.9); 7.6918 (2.6); 7.5706 (3.6); 7.4618 (2.8); 7.4536 (3.0); 7.4496 (3.0); 7.4413 (2.7); 7.3586 (3.5); 7.3260 (1.6); 7.3176 (1.8); 7.3140 (1.8); 7.3056 (1.5); 7.2814 (3.2); 7.1916 (6.2); 7.0678 (6.5); 6.3792 (1.2); 6.3676 (3.7); 6.3560 (3.8); 6.3444 (1.2); 6.1649 (0.7); 6.1534 (2.1); 6.1418 (2.1); 6.1304 (0.7); 5.4720 (2.2); 3.6907 (1.2); 3.6804 (1.4); 3.6671 (1.7); 3.6565 (1.7); 3.5529 (1.7); 3.5412 (1.7); 3.5292 (1.3); 3.5176 (1.2); 2.8690 (2.1); 2.8572 (2.2); 2.8428 (3.1); 2.8310 (3.1); 2.7454 (3.0); 2.7357 (3.0); 2.7193 (2.0); 2.7097 (2.0); 2.2920 (70.9); 2.1805 (0.5); 2.0801 (0.4); 2.0760 (0.8); 2.0719 (1.2); 2.0677 (0.9); 2.0647 (1.0); 1.9920 (0.6); 1.9852 (1.5); 1.9771 (2.7); 1.9693 (67.3); 1.9652 (130.9); 1.9610 (192.6); 1.9570 (133.9); 1.9529 (68.7); 1.8541 (0.4); 1.8501 (0.8); 1.8460 (1.2); 1.8418 (0.9); 1.8376 (0.7); 1.8255 (16.0); 1.8139 (16.0); 1.7681 (8.4);
[00202] [00202] The following usage examples illustrate the invention without limiting it. In these examples, the compounds according to the invention cited refer to the compounds listed in the Table with the corresponding reference numbers (No.).
[00203] [00203] To produce a suitable preparation of active compound,
[00204] [00204] Chard leaf discs (Brassica pekinensis) were sprayed with a preparation of the active ingredient in the desired concentration. After drying, the leaf discs were infested with mustard beetle larvae (Phaedon cochleariae).
[00205] [00205] After 7 days the mortality in% was determined. 100% means that all beetle larvae have been eliminated and 0% means that no beetle larvae have been eliminated.
[00206] [00206] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 100% at an application rate of 500g / ha: I-06, I-26, I-28, I-37, I- 38, I-40, I- 41, I-48, I-50, I-52, I-62, I-63, I-66, I-76, I-77, I-78, I-79, I-80, I-81, I-82, I-83, I-84, I-88, I-89, I-90, I-92, I-93, I-95, I-97, I- 98, I-99, I-100, I-103, I-104, I-105, I-106, I-107, I-108, I-110, I-113, I-114, I-115, I-116, I-117, I-119, I-120, I-121, I-122.
[00207] [00207] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 83% at an application rate of 500g / ha: I-118. Spodoptera frugiperda - spray test Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
[00208] [00208] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Other test concentrations are prepared by diluting with water containing emulsifier.
[00209] [00209] Corn leaf sections (Zea mays) were sprayed with a preparation of the active ingredient in the desired concentration. After drying, the leaf sections were infested with larvae of military caterpillar (Spodoptera frugiperda).
[00210] [00210] After 7 days the mortality in% was determined. 100% means that all caterpillars have been eliminated and 0% means that none of the caterpillars have been eliminated.
[00211] [00211] In this test, for example, the following compounds from the preparation examples showed satisfactory activity of 100% at an application rate of 500 g / ha: I-06, I-26, I-37, I-40, I -41, I-48, I- 50, I-62, I-63, I-66, I-76, I-77, I-78, I-80, I-81, I-82, I-84 , I-88, I-89, I-92, I-93, I-95, I-96, I-97, I-99, I-100, I-101, I-106, I-107, I -110, I-113, I-114, I-116, I-117, I-118, I-119, I-120, I-121, I-123, I-124, I-125, I-126 , I-127, I-129, I-130, I-131, I-132, I-135, I-136, I-137.
[00212] [00212] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 83% at an application rate of 500 g / ha: I-83, I-98, I-115. Myzus persicae - spray test Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylarylpolyglycol ether
[00213] [00213] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Other test concentrations are prepared by diluting with water containing emulsifier.
[00214] [00214] Chard leaf discs (Brassica pekinensis) infected with all instants of the green peach aphid (Myzus persicae) are sprayed with a preparation of the active ingredient in the desired concentration.
[00215] [00215] After 5 days the mortality in% was determined. 100% means that all aphids have been eliminated and 0% means that none of the aphids have been eliminated.
[00216] [00216] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 100% at an application rate of 500 g / ha: I-93, I-127.
[00217] [00217] In this test, for example, the following compounds from the preparation examples showed satisfactory activity of 90% at an application rate of 500 g / ha: I-40, I-96, I-123, I-124, I -125, I-126, I-134. Myzus persicae - Solvent oral test: 100 parts by weight of acetone
[00218] [00218] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvent, and the concentrate is diluted with water to the desired concentration.
[00219] [00219] 50 µl of the compound solution were introduced into microtiter plates and 150 µl of the IPL41 insect medium (33% + 15% sugar) was added to obtain a total volume of 200 µl per well. After that, the plates were sealed with parafilm through which a mixed population of green peach aphids (Myzus persicae) could feed on the preparation of compost.
[00220] [00220] After 5 days the mortality in% was determined. 100% means that all aphids have been eliminated and 0% means that none of the aphids have been eliminated.
[00221] [00221] In this test, for example, the following compounds from the preparation examples showed satisfactory activity of 100%
[00222] [00222] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 90% at an application rate of 20 ppm: I-52, I-103, I-116. Aphis gossypii - oral test Solvent: 100 parts by weight of acetone
[00223] [00223] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvent, and the concentrate is diluted with water to the desired concentration.
[00224] [00224] 50 µl of the compound solution were introduced into microtiter plates and 150 µl of the IPL41 insect medium (33% + 15% sugar) was added to obtain a total volume of 200 µl per well. After that the plates were sealed with parafilm through which a mixed population of cotton aphids (Aphis gossypii) can feed on the preparation of compost.
[00225] [00225] After 5 days the mortality in% was determined. 100% means that all aphids have been eliminated and 0% means that none of the aphids have been eliminated.
[00226] [00226] In this test, for example, the following compounds from the preparation examples showed 100% satisfactory activity at an application rate of 100 ppm: I-06, I-26, I-28, I-37, I-38 , I-40, I-41, I-48, I-50, I-52, I-62, I-63, I-66, I-76, I-77, I-78, I-80, I -81, I-82, I-83, I-85, I-88, I-89, I-90, I-92, I-93, I-94, I-95, I-97, I-98 , I-99, I-100, I-101, I-103, I-106, I-107, I-110, I-113, I-114, I-115, I-116, I-117, I -119, I-120, I-121, I-
[00227] [00227] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 90% at an application rate of 100 ppm: I-104. Diabrotica balteata - spray test Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
[00228] [00228] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvent, and the concentrate is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Other test concentrations are prepared by diluting with water containing emulsifier.
[00229] [00229] Soaked wheat seeds (Triticum aestivum) were placed in a multi-well plate filled with agar and a little water and are incubated for 1 day to germinate (5 seeds per well). The germinated wheat seeds were sprayed with a test solution containing the desired concentration of the active ingredient. After that, each unit was infected with 10-20 larvae of the striped cucumber beetle (Diabrotica balteata).
[00230] [00230] After 7 days the effectiveness in% was determined. 100% means that all plants developed in the same way as in the uninfected and untreated control; 0% means that none of the seedlings has developed.
[00231] [00231] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 100% at an application rate of 160 µg / well: I-06, I-26, I-28, I-37, I -38, I-40, I-41, I-48, I-50, I-62, I-63, I-66, I-76, I-77, I-78, I-79, I-80 , I-81, I-82, I-83, I-84, I-85, I-87, I-88, I-89, I-91, I-92, I-93, I-94, I -95, I-97, I-98, I-99, I-100, I-101, I-102, I-103, I-104, I-105, I-106, I-107, I-108 , I-109, I-110, I-112, I-
[00232] [00232] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 80% at an application rate of 160 µg / well: I-131. Meloidogyne incognita - Solvent test: 125.0 parts by weight of acetone
[00233] [00233] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvent, and the concentrate is diluted with water to the desired concentration.
[00234] [00234] Pots were filled with sand, an active ingredient solution, a suspension containing eggs and nematode larvae of the southern galls (Meloidogyne incognita) and lettuce seeds. Lettuce seeds germinated and seedlings developed. Galls developed on the roots.
[00235] [00235] After 14 days the nematicidal activity was determined based on the percentage of gall formation. 100% means that no galls were found and 0% means that the number of galls found in the roots of the treated plants was equal to that in the untreated control plants.
[00236] [00236] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 100% at an application rate of 20 ppm: I-38, I-48, I-79, I-82, I-88 , I-89, I-93, I-109.
[00237] [00237] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 90% at an application rate of 20 ppm: I-80, I-95, I-107, I-108, I-111 . Tetranychus urticae - spray test resistant to OP Solvent: 78.0 parts by weight of acetone
[00238] [00238] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Other test concentrations are prepared by diluting with water containing emulsifier.
[00239] [00239] Discs of common bean leaves (Phaseolus vulgaris) infected with all instars of painted spider mite (Tetranychus urticae) were sprayed with a preparation of the active ingredient in the desired concentration.
[00240] [00240] After 6 days the mortality in% was determined. 100% means that all spider mites have been eliminated and 0% means that none of the spider mites have been eliminated.
[00241] [00241] In this test, for example, the following compounds from the preparation examples showed satisfactory activity of 100% at an application rate of 500 g / ha: I-83, I-123.
[00242] [00242] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 95% at an application rate of 500 g / ha: I-110, I-116.
[00243] [00243] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 90% at an application rate of 500 g / ha: I-37, I-41, I-96, I-112.
[00244] [00244] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 80% at an application rate of 500 g / ha: I-81, I-82, I-97. Nezara viridula - spray test 1 Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide
[00245] [00245] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvent, and the concentrate is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Other test concentrations are prepared by diluting with water containing emulsifier.
[00246] [00246] Barley plants (Hordeum vulgare) infested with southern green stink bug larvae (Nezara viridula) were sprayed with a test solution containing the desired concentration of active ingredient.
[00247] [00247] After 4 days the mortality in% was determined. 100% means that all bed bugs have been eliminated; 0% means that none of the bed bugs have been eliminated.
[00248] [00248] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 100% at an application rate of 500 g / ha: I-06, I-28, I-37, I-38, I -40, I-41, I- 48, I-50, I-52, I-63, I-66, I-76, I-77, I-78, I-80, I-81, I-82 , I-83, I-84, I-95, I-96, I-97, I-98, I-99, I-100, I-104, I-106, I-107, I-108, I -110, I-113, I-114, I-115, I-116, I-117, I-119, I-120, I-121, I-122, I-123, I-124, I-125 , I-126, I-127, I-128, I-129, I-129, I-131, I-132, I-134, I-137.
[00249] [00249] In this test, for example, the following compounds from the preparation examples showed satisfactory activity of 90% at an application rate of 500 g / ha: I-62, I-79. Nilaparvata lugens - spray test 1 Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
[00250] [00250] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Other test concentrations are prepared by diluting with water containing emulsifier.
[00251] [00251] Rice plants (Oryza sativa) were sprayed with a preparation of the active ingredient in the desired concentration and the plants were infested with brown locust (Nilaparvata lugens).
[00252] [00252] After 4 days the mortality in% was determined. 100% means that all locusts have been eliminated and 0% means that none of the locusts have been eliminated.
[00253] [00253] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 100% at an application rate of 500 g / ha: I-06, I-28, I-37, I-40, I -41, I-48, I- 52, I-63, I-66, I-76, I-77, I-78, I-79, I-81, I-82, I-83, I-93 , I-96, I-97, I-98, I-100, I-106, I-107, I-108, I-110, I-113, I-114, I-115, I-116, I -117, I-119, I-121, I-122, I-123, I-131, I-134.
[00254] [00254] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 90% at an application rate of 500 g / ha: I-26, I-62, I-81, I-95, I -99, I-124. Nezara viridula - spray test 2 Solvent: 52.5 parts by weight of acetone 7 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
[00255] [00255] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvent, and the concentrate is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Ammonium salt and / or penetration enhancer at a dosage of 1000 ppm are added to the desired concentration, if necessary.
[00256] [00256] Barley plants (Hordeum vulgare) infested with southern green stink bug larvae (Nezara viridula) were sprayed with a test solution containing the desired concentration of active ingredient.
[00257] [00257] After 4 days the mortality in% was determined. 100% means that all bed bugs have been eliminated; 0% means that none of the bed bugs have been eliminated.
[00258] [00258] In this test, for example, the following compounds of the preparation examples showed satisfactory activity of 100% at an application rate of 500 g / ha: I-40, I-76, I-93. Nilaparvata lugens - spray test 2 Solvent: 52.5 parts by weight of acetone 7 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
[00259] [00259] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stipulated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Other test concentrations are prepared by diluting with water containing emulsifier. Ammonium salt and / or penetration enhancer at a dosage of 1000 ppm are added to the desired concentration, if desired.
[00260] [00260] Rice plants (Oryza sativa) were sprayed with the desired concentration of active compound and were infested with brown locusts (Nilaparvata lugens).
[00261] [00261] After 4 days the mortality in% was determined. 100% means that all locusts have been eliminated and 0% means that none of the locusts have been eliminated.
[00262] [00262] In this test, for example, the following compounds from the preparation examples showed satisfactory activity of 100%
[00263] [00263] Solvent: Acetone + 2000 ppm rapeseed oil methyl oil (RME)
[00264] [00264] In order to produce a solution containing sufficient active ingredient it was necessary to dissolve the test compound in a mixture of acetone / RME solvents. This solution was pipetted on a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Culex quinquefasciatus (brown domestic mosquito) were placed on the dry surface. The exposure time was 30 minutes.
[00265] [00265] Mortality in percentage (%) was determined after 24 hours of contact with the treated surface. 100% mortality means that all test insects died, while 0% means that not a single insect died.
[00266] [00266] The following numbers of example compounds showed in this test an 80-100% efficacy at a surface concentration of 100mg / m2: I-93, I-113.
[00267] [00267] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 20mg / m2: I-37, I-48, I-63, I-77, I-81, I -93, I-113, I-114, I-119, I-120.
[00268] [00268] The following numbers of example compounds showed in this test an 80-100% efficacy at a surface concentration of 4mg / m2: I-37, I-48, I-63, I-77, I-81, I -93, I-113, I-114, I-119, I-120. Anopheles test (surface treatment against ANPHFU and contact test) Solvent: Acetone + 2000 ppm rapeseed oil methyl ester (RME)
[00269] [00269] In order to produce a solution containing enough active ingredient it was necessary to dissolve the test compound in a mixture of acetone / RME solvents. This solution was pipetted on a glazed tile and after evaporation of acetone, adult mosquitoes of the species Anopheles funestus strain FUMOZ-R (Hunt et al., Med Vet Entomol. 2005 Sep; 19 (3): 271-5) the dry surface. The exposure time was 30 minutes.
[00270] [00270] Mortality in percentage (%) was determined after 24 hours of contact with the treated surface. 100% mortality means that all test insects died, while 0% means that not a single insect died.
[00271] [00271] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 100mg / m2: I-93, I-113.
[00272] [00272] The following numbers of example compounds showed in this test an 80-100% efficacy at a surface concentration of 20mg / m2: I-93, I-113.
[00273] [00273] The following numbers of example compounds showed in this test an 80-100% efficacy at a surface concentration of 4mg / m2: I-93, I-113. Aedes test (surface treatment against AEDSAE and contact test) Solvent: Acetone + 2000 ppm rapeseed oil methyl ester (RME)
[00274] [00274] In order to produce a solution containing enough active ingredient it was necessary to dissolve the test compound in a mixture of acetone / RME solvents. This solution was pipetted on a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Aedes aegypti strain MONHEIM were placed on the dry surface. The exposure time was 30 minutes.
[00275] [00275] Mortality in percentage (%) was determined after 24 hours of contact with the treated surface. 100% mortality means that all test insects died, while 0% means that not a single insect died.
[00276] [00276] The following numbers of example compounds showed in this test an 80-100% efficacy at a surface concentration of 100mg / m2: I-93, I-113.
[00277] [00277] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 20mg / m2: I-37, I-48, I-63, I-77, I-81, I -93, I-113, I-114, I-119, I-120.
[00278] [00278] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 4mg / m2: I-37, I-48, I-63, I-81, I-93, I -113, I-114, I-119, I-
[00279] [00279] In order to produce a solution containing enough active ingredient it was necessary to dissolve the test compound in a mixture of acetone / RME solvents. This solution was pipetted on a glazed tile and after evaporation of acetone, adult flies of the species Musca domestica strain WHO-N were placed on the dry surface. The exposure time was 30 minutes.
[00280] [00280] Mortality in percentage (%) was determined after 24 hours of contact with the treated surface. 100% mortality means that all test insects died, while 0% means that not a single insect died.
[00281] [00281] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 20mg / m2: I-37, I-48, I-63, I-77, I-81, I -113, I-114, I-119, I-
[00282] [00282] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 4mg / m2: I-37, I-48, I-63, I-77, I-81, I -113, I-114, I-119, I-
[00283] [00283] In order to produce a solution containing sufficient active ingredient, it was necessary to dissolve the test compound in a mixture of acetone / RME solvents. This solution was pipetted on a glazed tile and after evaporation of acetone, adult animals of the species Blattella germanica cepa PAULINIA were placed on the dry surface. The exposure time was 30 minutes.
[00284] [00284] Mortality in percentage (%) was determined after 24 hours of contact with the treated surface. 100% mortality means that all test insects died, while 0% means that not a single insect died.
[00285] [00285] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 20mg / m2: I-37, I-48, I-63, I-77, I-81, I -114, I-119, I-120.
[00286] [00286] The following numbers of example compounds showed in this test 80-100% efficacy at a surface concentration of 4mg / m2: I-37, I-48, I-63, I-81, I-114, I -119.

权利要求:
Claims (19)
[1]
1. Use of a compound of Formula (I) (I) where: X is O or S; Q1 and Q2 are independently CR5 or N, provided that at least one of Q1 and Q2 is N; Y is a direct bond or CH2; R1 is H; C1-C6alkyl optionally substituted with a substituent selected from: CN, CONH2, COOH, NO2 and -Si (CH3) 3; C1-C6haloalkyl; C2-C6 alkenyl; C2-C6haloalkenyl; C2-C6alkynyl; C2-C6haloalkynyl; C3-C4cycloalkyl-C1-C2alkyl- where C3-C4cycloalkyl is optionally substituted with 1 or 2 halogen atoms; oxetan-3-yl-CH2-; or benzyl optionally substituted with halo or C1-C3haloalkyl; R2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, where phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided that the substituents are not on any carbon adjacent to the carbon attached to the group, each one independently selected from: C1- C3alkyl, C1-C3haloalkyl, C1-C3haloalkylsulfanyl, C1- C3alkoxy, C1-C3haloalkoxy, halo, NO2, SF5, CN, CONH2,
COOH and C (S) NH2; R3 is C1-C3alkyl or C1-C3haloalkyl; R4 is pyridine, pyrimidine, pyrazine or pyridazine, where pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with a substituent selected from: C1- C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3- C4cycloalkyl, halo or hydroxy; R5 is H, C1-C3alkyl, C1-C3haloalkyl, C3-C4cycloalkyl, C1-C3alkoxy, C1-C3alkoxyC (O) - or (C1-C3alkoxy) 2CH-; or a salt thereof, said use being characterized by the fact that it is for controlling animal pests, including arthropods and insects, in plant protection.
[2]
2. Use, according to claim 1, characterized by the fact that Y is a direct link.
[3]
3. Use according to claim 1 or 2, characterized by the fact that X is O.
[4]
Use according to any one of claims 1 to 3, characterized by the fact that R3 is methyl.
[5]
Use according to any one of claims 1 to 4, characterized by the fact that Q1 is N, Q2 is CR5 and R5 is H, methyl, (CH3CH2O) 2CH- or CF3.
[6]
Use according to any one of claims 1 to 5, characterized by the fact that R4 is 2-pyridine, 3-pyridine, 4-pyridine, 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine, where 2-pyridine, 3-pyridine, 4-pyridine, 2-pyrimidine, 4-pyrimidine, 5-pyrimidine, 2-pyrazine, 3-pyridazine or 4-pyridazine are optionally substituted with a substituent selected from: C1- C3alkoxy, halo, C1-C3haloalkyl, or C1-C3alkyl.
[7]
7. Use according to claim 6, characterized by the fact that R4 is 2-pyridine optionally substituted with F, Cl, Br, I, C1-C3alkyl or C1-C3haloalkyl; or 2-pyrimidine optionally substituted with C1-C3alkoxy, F, Cl, Br, I, C1-C3alkyl or C1- C3haloalkyl.
[8]
8. Use according to any one of claims 1 to 7, characterized in that R1 is H, cyclopropyl-CH2-, cyclobutyl-CH2-, CH3-, CH3CH2-, n-propyl, CH≡C-CH2- , CF3CH2CH2-, FCH2CH2-, FCH2CH2CH2-, CHF2CH2-, 2,2-difluorocyclopropyl-CH2-, 2,2-dichlorocyclopropyl-CH2-, benzyl, 4-fluorobenzyl, 3-oxetanyl, (CH3) 3SiCH2- or CN-CH2 -.
[9]
Use according to any one of claims 1 to 8, characterized by the fact that R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3,4,5-trichlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 5-trifluoromethylpyridin-3-yl, 5-bromopyridin-3-yl 5-trifluoromethylsulfanylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethyl-phenyl, 3-chloro-5-cyanophenyl, 3-trifluoromethoxy-5-chlorophenyl, 3-trifluoromethylsulfanylphenyl 5-chlorophenyl, 2,6-bis (trifluoromethyl) pyridin-4-yl, 3,5-dimethylphenyl, 4-trifluoromethyl-6-chloropyridin-2-yl, 4,6-dichloropyridin-2-yl, 6-chloropyridazin- 2-yl, 3-bromo-5-chlorophenyl, 3-iodo-5-chlorophenyl, 4-chloro-3,5-difluorophenyl, 3-fluoro-5-cyanophenyl, or 3-chloro - [(2,2,2 - trifluoroethyl) sulfanyl] phenyl.
[10]
10. Use according to claim 9, characterized by the fact that R2 is 3,5-bis (trifluoromethyl) phenyl, 3,5-dichlorophenyl, 3-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylphenyl, 3-cyanophenyl, 3-chloro-5-cyanophenyl, 3-chloro-5-trifluoromethoxyphenyl, 3-chloro-5-trifluoromethylsulfanylphenyl, 5-trifluoromethylpyridin-3-yl, 3-bromo-5-trifluoromethylphenyl, 3-cyano-5-trifluoromethyl-phenyl, phenyl 3,5-dimethylphenyl, 4-trifluoromethyl-6-chloropyridin-2-yl, 4,6-dichloropyridin-2-yl, 6-chloropyridazin-
2-yl, 3-bromo-5-chlorophenyl, 3-iodo-5-chlorophenyl, 4-chloro-3,5-difluorophenyl, 3-fluoro-5-cyanophenyl, or 3-chloro - [(2,2,2 - trifluoroethyl) sulfanyl] phenyl.
[11]
11. Use according to claim 1, characterized by the fact that it is N- (cyclopropylmethyl) -N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazole-3 -yl) ethyl] -3,5-bis (trifluoromethyl) benzamide, N-Prop-2-ynyl-N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazole- 3-yl) ethyl] -3,5-bis (trifluoromethyl) benzamide, N-methyl-N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl ) ethyl] -3,5- bis (trifluoromethyl) benzamide, 3-chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5-trifluoro-methyl) benzamide, 3-chloro-N-prop-2-ynyl-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl ] -5- (trifluoromethyl) benzamide, 3-chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) -N- (3.3 , 3-trifluoropropyl) benzamide, N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl- 1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) pyridine-3 -carboxamide, 3-chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethoxy) benzamide, 3-cyano-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] benzamide, 3- chloro-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N- prop-2-ynyl-N- [1- (2-pyrimidin-2-yl- 1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, 3-cyano-N- (cyclopropylmethyl ) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, 3-bromo-N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, N- [1- (2- pyrimidin-2-yl-1, 2,4-triazol-3-yl) ethyl] -3,5-bis (trifluoromethyl) benzamide, N- [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazole-3 -yl) ethyl] -3,5- bis (trifluoromethyl) benzamide, 3-chloro-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5 - (trifluoromethyl) benzamide, 3-chloro-N - [(1S) -1- (2-pyrimidin-2-yl- 1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N-
(cyclopropylmethyl) -N- [1- [2- (5-fluoropyrimidin-2-yl) -5-methyl-1,2,4-triazol-3-yl] ethyl] -5- (trifluoromethyl) benzamide, 3- chloro-N- [1- [2- (5-chloropyrimidin-2-yl) - 5-methyl-1,2,4-triazol-3-yl] ethyl] -N- (cyclopropylmethyl) -5- (trifluoromethyl) benzamide, 3-chloro-N- [1- [2- (5-chloropyrimidin-2-yl) -1,2,4-triazol-3-yl] ethyl] -N- (cyclopropylmethyl) -5- (trifluoromethyl) benzamide, 3-chloro- N- (cyclopropylmethyl) -N- [1- [2- (5-fluoropyrimidin-2-yl) -1,2,4-triazol-3-yl] ethyl] - 5- (trifluoromethyl) benzamide, 3-chloro-N- [1- [2- (5-chloro-2-pyridyl) -1,2,4-triazol-3-yl] ethyl] -N- (cyclopropylmethyl) -5- (trifluoromethyl) benzamide, 3-chloro- N- (2,2-difluoroethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, N- [1- [2- (5-bromopyrimidin-2-yl) -1,2,4-triazol-3-yl] ethyl] -3-chloro-N- (cyclopropylmethyl) -5- (trifluoromethyl) benzamide, 3-chloro-N- (cyclopropylmethyl) -N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N-ethyl-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluorom ethyl) benzamide, 3-chloro-N-methyl-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, 3- chloro- N- (cyclopropylmethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethylsulfanyl) benzamide, 3-chloro-5- cyano-N- [1- (2-pyrimidin-2-yl- 1,2,4-triazol-3-yl) ethyl] benzamide, 3-chloro-N - [(1S) -1- [2- (2 -pyridyl) -1,2,4- triazol-3-yl] ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N- [1- (2-pyrimidin-2-yl- 1,2,4- triazol-3-yl) ethyl] -5- (trifluoromethoxy) benzamide, or 3-chloro-N - [(1S) -1- [2- (5-chloro-2-pyridyl) -1,2,4-triazole -3-yl] ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N- (2,2-difluoroethyl) -N- [1- (2-pyrimidin-2-yl-1,2,4-triazole -3-yl) ethyl] -5- (trifluoromethoxy) benzamide, 3-bromo-5-chloro-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl ] benzamide, 3-chloro-5-iodo-N- [1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] benzamide, 3-chloro-N- (2, 2-difluoroethyl) -N - [(1S) -1- (2-pyrimidin-2-yl-1,2,4-triazol-3-yl) ethyl] -5- (trifluoromethyl) benzamide, N - [(1S ) - 1- [2- (5-bromo-2-pyridyl) -1,2,4-triazol-3-yl] et yl] -3-chloro-5- (trifluoromethyl) benzamide, 3-chloro-N - [(1S) -1- [2- (5-chloro-2-pyridyl) -5- (trifluoromethyl) -1,2, 4-triazol-3-yl] ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N - [(1S) -1- [2- (5-iodo-2-pyridyl) -1,2,4- triazol-3-yl] ethyl] -5-
(trifluoromethyl) benzamide, N - [(1S) -1- [2- (5-chloro-2-pyridyl) -5- (trifluoromethyl) -1,2,4-triazol-3-yl] ethyl] -3, 5-bis (trifluoromethyl) benzamide, 3-bromo-5-chloro-N - [(1S) -1- [2- (5-chloro-2-pyridyl) -1,2,4-triazol-3-yl] ethyl] benzamide, 3,5-bis (trifluoromethyl) -N - [(1S) -1- [2- [5- (trifluoromethyl) pyrimidin-2-yl] -1,2,4-triazol-3-yl] ethyl] benzamide, 3-chloro-N- [(1S) -1- [2- (5-fluoro-2-pyridyl) -1,2,4-triazol-3-yl] ethyl] -5- (trifluoromethyl) benzamide, 3-chloro-N - [(1S) -1- [2-pyrimidin-2-yl-5- (trifluoromethyl) -1,2,4-triazol-3-yl] ethyl] -5- (trifluoromethyl) benzamide, or 3-chloro-5- (trifluoromethyl) -N - [(1S) -1- [2- [5- (trifluoromethyl) -2-pyridyl] -1,2,4-triazol-3-yl] ethyl ] benzamide.
[12]
12. Method for controlling animal pests in plant protection, including arthropods and insects, characterized by the fact that a compound or a salt, as defined in any of claims 1 to 11, is left to act on animal pests and / or in habitat, methods of treatment of the human or animal body, by surgical methods or by therapeutic and diagnostic methods performed on the human or animal body, are excluded.
[13]
13. Use according to any of claims 1 to 11, characterized by the fact that it is for seed treatment.
[14]
14. Use according to any one of claims 1 to 11, characterized by the fact that it is in vector control, the host being the human body.
[15]
15. Vector control method, characterized by the fact that a compound or a salt, as defined in any one of claims 1 to 11, is left to act on the vectors and / or their habitat, in which the host is the body and in which methods of treatment of the human body, by surgical methods or by therapeutic and diagnostic methods performed on the human body, are excluded.
[16]
16. Compound, characterized by the fact that it is selected from the group consisting of the following compounds from Formula (I-76) to (I-151):
I-76 I-77 I-78
I-80 I-81 I-84
I-89 I-92 I-93
I-97 I-100 I-107
I-113 I-114 I-117
I-119 I-120 I-121
I-125 I-126 I-127
I-129 I-131 I-132
I-136 I-137 I-140 I-143 I-145 I-151
[17]
17. Formulation, characterized by the fact that it comprises a compound, as defined in any one of claims 1 to 11 and 16, or salts thereof, and agrochemically acceptable auxiliaries.
[18]
18. Use of a compound, as defined in any of claims 1 to 11 and 16, or of salts thereof, characterized by the fact that it is for the preparation of a formulation for controlling animal pests in the protection of plants, including arthropods and insects and / or vector control.
[19]
19. Pest-resistant seed, characterized by the fact that it comprises a seed coated with a compound, as defined in any of claims 1 to 11 and 16, or salts thereof, or a formulation, as defined in claim 17.

类似技术:

---

公开号 | 公开日 | 专利标题

---

BR112020016946A2|2020-12-15|USE OF HETEROARYL-TRIAZOLE COMPOUNDS AND HETEROARYL-TETRAZOLE AS PESTICIDES IN PLANT PROTECTION

---

EP3544978B1|2020-11-04|2-[3-|-2h-indazol-2-yl]-3h-imidazo[4,5-b]pyridine derivatives and related compounds as pesticides

---

EP3697217B1|2021-08-11|Active compound combinations having insecticidal/acaricidal properties

---

ES2702454T3|2019-03-01|Bipyrazole compounds substituted with halogen to control animal pests

---

EP3697216B1|2021-11-03|Active compound combinations having insecticidal/acaricidal properties

---

CN108699045B|2021-02-12|Substituted 2-oxoimidazolyl carboxamides as pest control agents

---

EP3608311A1|2020-02-12|Crystalline form a of n-[4-chloro-3-[|carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-|pyrazole-3-carboxamide

---

ES2894107T3|2022-02-11|Combinations of active compounds with insecticidal/acaricidal properties

---

US11191271B2|2021-12-07|Active compound combinations having insecticidal/acaricidal properties

---

JP6994504B2|2022-01-14|2- | aryl substituted fused bicyclic heterocyclic derivative as a pest control agent

---

US20210068396A1|2021-03-11|Active ingredient combinations with insecticidal, nematicidal and acaricidal properties

---

WO2019224143A1|2019-11-28|Active ingredient combinations with insecticidal, nematicidal and acaricidal properties

---

WO2020178067A1|2020-09-10|Active compound combinations having insecticidal/acaricidal properties

---

WO2019197615A1|2019-10-17|Active ingredient combinations with fungicides, insecticides and acaricidal properties

---

WO2021069575A1|2021-04-15|Heteroaryl-substituted pyrazine derivatives as pesticides

---

WO2021068179A1|2021-04-15|Novel heteroaryl-substituted pyrazine derivatives as pesticides

---

WO2020187656A1|2020-09-24|Active compound combinations having insecticidal/acaricidal properties

---

WO2019076751A1|2019-04-25|Active compound combinations having insecticidal/acaricidal properties

同族专利:

---

公开号 | 公开日

---

EP3761791A1|2021-01-13|

---

JP2021516238A|2021-07-01|

---

US20200404919A1|2020-12-31|

---

CL2020002323A1|2021-04-30|

---

AU2019229521A1|2020-09-03|

---

TW201940477A|2019-10-16|

---

CN111818801A|2020-10-23|

---

KR20200129128A|2020-11-17|

---

WO2019170626A1|2019-09-12|

---

UY38142A|2019-10-01|

---

PH12020551407A1|2021-09-01|

引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

JPS63135364A|1986-11-28|1988-06-07|Nissan Chem Ind Ltd|Amide-substituted acetonitrile derivative, production thereof and agricultural and horticultural germicide|

---

JPH10204066A|1997-01-28|1998-08-04|Nippon Bayer Agrochem Kk|1-phenyl-5-anilinotetrazoles and theirs utilization as agrochemical|

---

EP1099695A1|1999-11-09|2001-05-16|Laboratoire Theramex S.A.|5-aryl-1H-1,2,4-triazole compounds as inhibitors of cyclooxygenase-2 and pharmaceutical compositions containing them|

---

GB0213715D0|2002-06-14|2002-07-24|Syngenta Ltd|Chemical compounds|

---

TWI312272B|2003-05-12|2009-07-21|Sumitomo Chemical Co|Pyrimidine compound and pests controlling composition containing the same|

---

GB0414438D0|2004-06-28|2004-07-28|Syngenta Participations Ag|Chemical compounds|

---

AU2005296529B2|2004-10-20|2011-03-24|Ihara Chemical Industry Co., Ltd.|3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient|

---

SI1947098T1|2005-10-06|2012-02-29|Nippon Soda Co|Cyclic amine compounds and pest control agent|

---

JP5268461B2|2008-07-14|2013-08-21|ＭｅｉｊｉＳｅｉｋａファルマ株式会社|PF1364 substance, its production method, production strain, and agricultural and horticultural insecticide containing the same as an active ingredient|

---

CN101337940B|2008-08-12|2012-05-02|国家农药创制工程技术研究中心|Nitrogen heterocyclic ring dichlorin allyl ether compounds with insecticidal activity|

---

CN101337937B|2008-08-12|2010-12-22|国家农药创制工程技术研究中心|N-benz-3-substituted amino pyrazoles compounds with insecticidal activity|

---

CN101715774A|2008-10-09|2010-06-02|浙江化工科技集团有限公司|Preparation and use of compound having insecticidal activity|

---

EP2184273A1|2008-11-05|2010-05-12|Bayer CropScience AG|Halogen substituted compounds as pesticides|

---

GB0820344D0|2008-11-06|2008-12-17|Syngenta Ltd|Herbicidal compositions|

---

AU2009324389B2|2008-12-12|2016-04-28|Syngenta Limited|Spiroheterocyclic N-oxypiperidines as pesticides|

---

TWI487486B|2009-12-01|2015-06-11|Syngenta Participations Ag|Insecticidal compounds based on isoxazoline derivatives|

---

WO2011085575A1|2010-01-15|2011-07-21|江苏省农药研究所股份有限公司|Ortho-heterocyclyl formanilide compounds, their synthesis methods and use|

---

BR112012030408A2|2010-05-31|2015-09-29|Syngenta Participations Ag|crop breeding method|

---

CN101967139B|2010-09-14|2013-06-05|中化蓝天集团有限公司|Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof|

---

CN103261188A|2010-12-17|2013-08-21|先正达参股股份有限公司|Insecticidal compounds|

---

WO2013050317A1|2011-10-03|2013-04-11|Syngenta Limited|Polymorphs of an isoxazoline derivative|

---

CN103842346A|2011-10-03|2014-06-04|先正达参股股份有限公司|Isoxazoline derivatives as insecticidal compounds|

---

CN102391261A|2011-10-14|2012-03-28|上海交通大学|N-substituted dioxazine compound as well as preparation method and application thereof|

---

TWI566701B|2012-02-01|2017-01-21|日本農藥股份有限公司|Arylalkyloxypyrimidine derivatives and agrohorticultural insecticides comprising said derivatives as active ingredients, and method of use thereof|

---

EP2830421B1|2012-03-30|2017-03-01|Basf Se|N-substituted pyridinylidene thiocarbonyl compounds and their use for combating animal pests|

---

EP2647626A1|2012-04-03|2013-10-09|Syngenta Participations AG.|1-Aza-spiro[4.5]dec-3-ene and 1,8-diaza-spiro[4.5]dec-3-ene derivatives as pesticides|

---

US9282739B2|2012-04-27|2016-03-15|Dow Agrosciences Llc|Pesticidal compositions and processes related thereto|

---

MX2014013069A|2012-04-27|2015-07-06|Dow Agrosciences Llc|Pesticidal compositions and processes related thereto.|

---

CN103109816B|2013-01-25|2014-09-10|青岛科技大学|Thiobenzamide compounds and application thereof|

---

CN103232431B|2013-01-25|2014-11-05|青岛科技大学|Dihalogenated pyrazole amide compound and its use|

---

WO2014158644A1|2013-03-13|2014-10-02|Dow Agrosciences Llc|Process for the preparation of triaryl rhamnose carbamates|

---

BR112015029268B1|2013-05-23|2020-10-20|Syngenta Participations Ag|pesticide composition, combination package, use, method of increasing the effectiveness and reducing the phytotoxicity of pesticide-active tetramic acid compounds, non-therapeutic method to combat and control pests|

---

CN103265527B|2013-06-07|2014-08-13|江苏省农用激素工程技术研究中心有限公司|Anthranilamide compound as well as preparation method and application thereof|

---

CN103524422B|2013-10-11|2015-05-27|中国农业科学院植物保护研究所|Benzimidazole derivative, and preparation method and purpose thereof|

---

WO2015058021A1|2013-10-17|2015-04-23|Dow Agrosciences Llc|Processes for the preparation of pesticidal compounds|

---

CN105636441B|2013-10-17|2018-06-15|美国陶氏益农公司|The method for preparing Pesticidal compound|

---

AR108222A1|2016-05-05|2018-08-01|Elanco Tiergesundheit Ag|HETEROARIL-1,2,4-TRIAZOL AND HETEROARIL-TETRAZOL COMPOUNDS|

---

WO2018086605A1|2016-11-10|2018-05-17|山东罗欣药业集团股份有限公司|Nitrogenous macrocyclic compound, preparation method therefor, pharmaceutical composition and application thereof|UY38366A|2018-09-13|2020-04-30|Syngenta Participations Ag|PESTICIDALLY ACTIVE AZOL-AMIDE COMPOUNDS|

---

EP3941912A1|2019-03-20|2022-01-26|Syngenta Crop Protection AG|Pesticidally active azole amide compounds|

---

EP3725788A1|2019-04-15|2020-10-21|Bayer AG|Novel heteroaryl-substituted aminoalkyl azole compounds as pesticides|

---

TW202118754A|2019-07-23|2021-05-16|德商拜耳廠股份有限公司|Novel heteroaryl-triazole compounds as pesticides|

---

WO2021013719A1|2019-07-23|2021-01-28|Bayer Aktiengesellschaft|Novel heteroaryl-triazole compounds as pesticides|

---

TW202128664A|2019-10-09|2021-08-01|德商拜耳廠股份有限公司|Novel heteroaryl-triazole compounds as pesticides|

---

WO2021069569A1|2019-10-09|2021-04-15|Bayer Aktiengesellschaft|Novel heteroaryl-triazole compounds as pesticides|

---

WO2021068179A1|2019-10-11|2021-04-15|Bayer Animal Health Gmbh|Novel heteroaryl-substituted pyrazine derivatives as pesticides|

---

TW202128650A|2019-10-11|2021-08-01|德商拜耳動物保健有限公司|Novel heteroaryl-substituted pyrazine derivatives as pesticides|

---

TW202134226A|2019-11-18|2021-09-16|德商拜耳廠股份有限公司|Novel heteroaryl-triazole compounds as pesticides|

---

TW202136248A|2019-11-25|2021-10-01|德商拜耳廠股份有限公司|Novel heteroaryl-triazole compounds as pesticides|

---

WO2021122906A1|2019-12-18|2021-06-24|Intervet International B.V.|Anthelmintic compounds comprising azaindoles structure|

---

WO2021122911A1|2019-12-18|2021-06-24|Intervet International B.V.|Anthelmintic compounds comprising a quinoline structure|

---

WO2021165195A1|2020-02-18|2021-08-26|Bayer Aktiengesellschaft|Heteroaryl-triazole compounds as pesticides|

---

WO2021224323A1|2020-05-06|2021-11-11|Bayer Aktiengesellschaft|Novel heteroaryl-triazole compounds as pesticides|

---

EP3929189A4|2020-06-25|2021-12-29|Bayer Animal Health Gmbh|Novel heteroaryl-substituted pyrazine derivatives as pesticides|

法律状态:
2021-12-07| B350| Update of information on the portal [chapter 15.35 patent gazette]|

优先权:

---

申请号 | 申请日 | 专利标题

---

EP18160736|2018-03-08|

---

EP18160736.7|2018-03-08|

---

EP18185778|2018-07-26|

---

EP18185778.0|2018-07-26|

---

PCT/EP2019/055368|WO2019170626A1|2018-03-08|2019-03-05|Use of heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides in plant protection|

---