N-(cyclopropylmethyl)-5-(methylsulfonyl)-N-{1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}benzamide derivatives and corresponding pyridine-carboxamide derivatives as pesticides
By developing heteroaryl-triazole and heteroaryl-tetraazole compounds of general formula (I), the problems of resistance and cost of existing pesticides and veterinary anthelmintics have been solved, achieving broad-spectrum and highly effective insecticidal effects.
Patent Information
- Application Number
- JP2025040873
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2018-11-29
- Filing Date
- 2025-03-14
- Publication Date
- 2026-02-09
- Estimated Expiration
- 2039-04-10
AI Technical Summary
Existing pesticides and veterinary dewormers face problems such as resistance and high synthesis costs, and lack new compounds with broad-spectrum properties and improved performance.
A heteroaryl-triazole and heteroaryl-tetraazole compound of general formula (I) is provided as an insecticide and veterinary anthelmintic, having specific structural features and substituent groups to broaden its insecticidal spectrum and improve its efficacy.
These compounds are broad-spectrum and highly effective in controlling insects and parasites, overcoming resistance problems and reducing synthesis costs.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to novel heteroaryl-triazole compounds and heteroaryl-tetrazoles. compounds, formulations and compositions containing such compounds, and pesticides in plant protection In the control of animal pests (which includes arthropods and insects) and their use for controlling ectoparasites in animals. [Background technology]
[0002] Formula (I)(R 3b = hydrogen) and certain heteroaryl-triazole compounds Heteroaryl-tetrazole compounds for use in controlling ectoparasites in animals and is disclosed in WO2017 / 192385.
[0003] Modern plant protection products and veterinary ectoparasiticides offer a wide range of benefits, e.g., efficacy, durability, spectrum Torque and resistance breaking characteristics Many requirements must be met. The combinatorial possibilities of the active compounds, in addition to the cost involved in synthesizing them, play a role. Furthermore, resistance may develop. For all these reasons, new crop protection compositions or Therefore, the search for veterinary ectoparasiticides cannot be considered complete, and there are many compounds that are being developed in comparison with known compounds. In comparison, there is a constant demand for new compounds with improved properties, at least in terms of individual aspects. It is being done. [Prior art documents] [Patent documents]
[0004] [Patent Document 1] International Patent Application Publication No. 2017 / 192385 Summary of the Invention [Problem to be solved by the invention]
[0005] The object of the present invention is to provide compounds that broaden the spectrum of pesticides in various respects. The purpose was to provide [Means for solving the problem]
[0006] Therefore, the present invention provides a compound of general formula (I) [ka]
[0007] [In the formula (configuration 1-1): X is O or S; Q 1 and Q 2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or CH; R 1 is hydrogen; C1-C6 alkyl [wherein the alkyl is -CN, -CONH2, Substituted with one substituent selected from -COOH, -NO2 and -Si(CH3)3 C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl C2-C6 alkynyl;C2-C6 haloalkynyl;C3-C4 cycloalkyl-C 1-C2 alkyl- [wherein the C3-C4 cycloalkyl is substituted with one or two halogen atoms] oxetan-3-yl-CH2- or benzyl [which may be substituted by an atom]; wherein the benzyl may be substituted with halogen or C1-C3 haloalkyl. can be; R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine is substituted with 1 to 5 substituents. provided that at least one substituent is adjacent to the carbon bonded to the C=X group. and the substituents are halogen, hydroxy, -N H2, -CN, -SF5, -COOH, -CONH2, -NO2, or in any case C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, chloroalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl , C1-C6 alkylsulfonyl, C1-C3 haloalkylthio, C3-C6 cycloalkenyl alkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkyl Sulfonyl, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl , phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, -NH(C1- C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, - N(C1-C4 alkyl)CO-C1-C4 alkyl, -NHCO-phenyl, -CO2 C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl) -CONH(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)( C3-C6 cycloalkyl), -C(=NOC1-C4 alkyl)H, -C(=NOC1 -C4 alkyl)-C1-C4 alkyl; phenyl and 5-6 membered heteroaryl [wherein and the phenyl or 5-6 membered heteroaryl is halogen, -CN, in either case Optionally substituted C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy and optionally substituted with 1 to 2 substituents independently selected from the group consisting of alkoxy and alkoxy. each independently selected from the group consisting of: Or, R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine has a total of 1 to 3 substituents. and wherein the substituent is substituted with either of the carbons adjacent to the carbon bonded to the C=X group. and at least one and at most three substituents are C1-C6 Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3 -C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C 6 cycloalkylsulfonyl, C1-C3 haloalkylsulfinyl, C1-C3 haloa alkylsulfonyl, C3-C6 cycloalkyl, optionally substituted in any case; Phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, -NH(C1-C 4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N (C1-C4 alkyl)CO-C1-C4 alkyl -NHCO-phenyl, -CO2C 1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl )2, -CONH(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)(C 3-C6 cycloalkyl), -C(=NOC1-C4 alkyl)H, -C(=NOC1- C4 alkyl)-C1-C4 alkyl; phenyl and 5-6 membered heteroaryl [where The phenyl or 5- to 6-membered heteroaryl may be substituted with halogen, —CN, or Optionally substituted C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy 1 to 2 substituents independently selected from the group consisting of alkoxy and C1-C4 haloalkoxy independently selected from group A consisting of: The remaining 1 to 2 optional substituents are halogen, hydroxy, -NH2, -CN, -SF5, -COOH, -CONH2, -NO2, optionally substituted C1-C 6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1 -C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl , C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 halo Alkyl sulfonyl, phenyl sulfanyl, phenyl sulfinyl, phenyl sulfonyl -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1 -C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -NHCO- Phenyl, -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON (C1-C4 alkyl)2, -CONH(C3-C6 cycloalkyl), -CON(C1 -C4 alkyl)(C3-C6 cycloalkyl), -C(=NOC1-C4 alkyl)H , -C(=NOC1-C4 alkyl)-C1-C4 alkyl; phenyl and 5- to 6-membered phenyl wherein the phenyl or 5-6 membered heteroaryl is selected from the group consisting of halogen, -CN , optionally substituted C1-C6 alkyl, C1-C3 haloalkyl and 1 to 2 substituents independently selected from the group consisting of C1-C4 alkoxy. each independently selected from group B consisting of: Or, R 2 is naphthyl, wherein the naphthyl is selected from halogen, hydroxy, -CN, - COOH, -CONH2, -NO2, -SF5, -NH2, in all cases substituted C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, optionally -C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 halo Alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 Alkyl sulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkoxy sulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, phenylsulfonyl sulfonyl, phenylsulfinyl, phenylsulfonyl, -NH(C1-C4 alkyl ), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C 4 alkyl)CO-C1-C4 alkyl, -NHCO-phenyl, -CO2C1-C4 alkyl alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -C (=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alk alkyl; phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl Aryl is a C1-C6 alkyl group optionally substituted with halogen, -CN, each independently selected from the group consisting of alkyl, C1-C3 haloalkyl, and C1-C4 alkoxy; and each independently selected from the group consisting of: and optionally substituted with 1 to 3 substituents selected from the group consisting of methyl, ... Or, R 2 is a 4- to 10-membered saturated and partially unsaturated heterocyclyl, a 5-membered heteroaryl, a heterocyclic ring selected from the group consisting of 9-membered heteroaryl and 10-membered heteroaryl; where these are halogen, ═O (oxo), hydroxy, —CN, -COOH, -CONH2, -NO2, -SF5, -NH2, in all cases substituted Optionally, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkoxy C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 Haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C 6 alkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkenyl alkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio , C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, phenyl Sulfanyl, phenylsulfinyl, phenylsulfonyl, -NH(C1-C4 alkyl) -NHCO-C1-C4 alkyl, -N(C1- C4 alkyl)CO-C1-C4 alkyl, -NHCO-phenyl, -CO2C1-C4 Alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, - C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl alkyl; phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl is Heteroaryl is a C1-C6 alkyl group optionally substituted with halogen, -CN, independently selected from the group consisting of alkyl, C1-C3 haloalkyl, and C1-C4 alkoxy; and each independently selected from the group consisting of: and optionally substituted with 1 to 3 substituents selected from the group consisting of methyl, ... Or, R 2 is C1-C6 alkyl, C3-C6 cycloalkyl, or haloalkyl or C1-C6 haloalkyl; R 3a , R 3b are independently hydrogen; halogen; -CN; C1-C6 alkyl [where The alkyl is halogen, hydroxy, -CN, -COOH, -CONH2, -NO2 , -NH2, C1-C6 alkyl which may be substituted in either case, C3-C6 silyl Chloroalkyl, C1-C4 alkoxy, C1-C3 alkylthio, C1-C3 alkyls sulfinyl, C1-C3 alkylsulfonyl, -NH(C1-C4 alkyl), -N(C 1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl) CO-C1-C4 alkyl, -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl) 1 to 3 independently selected from the group consisting of -CON(C1-C4 alkyl) and -CON(C1-C4 alkyl) optionally substituted by a substituent selected from the group consisting of C3-C6 cycloalkyl; Optionally substituted C1-C6 haloalkyl; optionally substituted C2-C6 alkene Optionally substituted C2-C6 haloalkenyl; Optionally substituted C2-C 6 alkynyl; benzyl [wherein the phenyl substituents are halogen, hydroxy, -CN , -COOH, -CONH2, -NO2, -NH2, -SF5, in either case, C1-C6 alkyl, C1-C4 alkoxy, C1-C3 alkylthio, Select from the group consisting of C1-C3 alkylsulfinyl and C1-C3 alkylsulfonyl each of which may be substituted with 1 to 5 independently selected substituents; heterocyclyl-C 1-C6 alkyl, wherein the heterocyclyl substituent is a 4- to 10-membered saturated and partially unsaturated Selected from the group consisting of saturated heterocyclyl, 5-membered heteroaryl, and 6-membered heteroaryl where these are halogen, ═O (oxo), hydroxy, —CN, -COOH, -CONH2, -NO2, -NH2, which may be substituted in any case 1 to 4 alkyl groups independently selected from the group consisting of C1-C6 alkyl and C1-C4 alkoxy; phenyl, wherein the phenyl is optionally substituted with halogen, hydroxybenzoate ... hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2, -SF5, any optionally substituted C1-C6 alkyl, C1-C4 alkoxy, C1-C 3 alkylthio, C1-C3 alkylsulfinyl and C1-C3 alkylsulfonyl and optionally substituted with 1 to 5 substituents each independently selected from the group consisting of: heterocyclyl, wherein the heterocyclyl substituent is a 4- to 10-membered saturated and partially Selected from the group consisting of unsaturated heterocyclyl, 5-membered heteroaryl, and 6-membered heteroaryl. wherein these are selected from halogen, ═O (oxo), hydroxy, -CN, , -COOH, -CONH2, -NO2, -NH2, even if substituted in any case 1 independently selected from the group consisting of C1-C6 alkyl and C1-C4 alkoxy and optionally substituted with up to 3 substituents; Or, R 3a , R 3b together with the carbon to which they are attached form a C3-C6-carbocyclic ring system or Forming a 3- to 6-membered heterocyclic ring system, wherein the ring system is substituted with halogen, -CN, optionally substituted C1-C6 alkyl, C1-C4 alkoxy and C1-C3 substituted with 1 to 2 substituents independently selected from the group consisting of haloalkoxy; It's okay to be there; R 4 is pyridine, pyrimidine, pyrazine, pyridazine or a 5-membered heteroaryl wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is Halogen, hydroxy, -CN, -COOH, -CONH2, -CSNH2, -NO2, -NH2, C1-C6 alkyl, C3-C6 cycloalkyl, optionally substituted in any case C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfinyl sulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1- C3 haloalkylsulfonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl -NHCO-C1-C4 alkyl, -NHCO-C3-C6 cycloalkyl, - NHCO-phenyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -N(C -N(C1-C4 alkyl)CO-C3-C6 cycloalkyl, -N(C1-C4 alkyl)CO -phenyl, -N(SO2C1-C3 alkyl), -NH(SO2C1-C3 alkyl ), -N(C1-C4 alkyl)(SO2C1-C3 alkyl), -CO2C1-C4 alkyl alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -C (=NOC1-C4 alkyl)H and -C(=NOC1-C4 alkyl)-C1-C4 alkyl optionally substituted with 1 to 3 substituents selected from the group consisting of alkyl; R 5 is hydrogen, halogen, -CN or optionally substituted C1 -C3 alkyl, C3-C4 cycloalkyl, C1-C3 alkoxy, C1-C3 alkoxy C(O)-, (C1-C3 alkoxy)CH-, -CO2C1-C4 alkyl, - CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NHCO-C 1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -C(=N -OC(=NOC1-C4 alkyl)H or -C(=NOC1-C4 alkyl)-C1-C4 alkyl It is a kill. The present invention provides a compound represented by the formula:
[0008] The present invention further provides a compound of general formula (I) [In the formula (configuration 1-2), X is O or S; Q 1 and Q 2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or an optionally substituted CH; R 1 is hydrogen; C1-C6 alkyl [wherein the alkyl is -CN, -CONH2, Substituted with one substituent selected from -COOH, -NO2 and -Si(CH3)3 C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl C2-C6 alkynyl;C2-C6 haloalkynyl;C3-C4 cycloalkyl-C 1-C2 alkyl- [wherein the C3-C4 cycloalkyl is substituted with one or two halogen atoms] oxetan-3-yl-CH2- or benzyl [which may be substituted by an atom]; wherein the benzyl may be substituted with halogen or C1-C3 haloalkyl. can be; R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine is substituted with 1 to 5 substituents. provided that at least one substituent is adjacent to the carbon bonded to the C=X group. and the substituent is present on any carbon atom of Halogen, hydroxy, -NH2, -CN, -SF5, -COOH, -CONH2, -N O2 and C1-C6 alkyl, C3-C6 cycloalkyl, optionally substituted in either case , C3-C6 cycloalkyl-C1-C6 alkyl, C1-C6 haloalkyl, C1-C 6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl sulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C3- C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 Cycloalkylsulfonyl, C1-C6 haloalkylsulfinyl, C1-C6 haloal phenylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, -NH(C1-C6 alkyl), -N(C1-C6 alkyl)2, -NHCO-C1-C 6 alkyl, -N(C1-C6 alkyl)CO-C1-C6 alkyl, -NHCO-phenyl nyl, -CO2C1-C6 alkyl, -CONH(C1-C6 alkyl), -CON(C 1-C6 alkyl), -CONH(C3-C6 cycloalkyl), -CON(C1-C 6 alkyl) (C3-C6 cycloalkyl), -C(=NOC1-C6 alkyl)H, - C(=NOC1-C6 alkyl)-C1-C6 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from halogen, -CN, and optionally substituted C1-C6 alkyl. , each independently selected from the group consisting of C1-C6 haloalkyl and C1-C6 alkoxy; and Optionally substituted 4- to 6-membered saturated or partially unsaturated heterocyclic ring each independently selected from the group consisting of: Or, R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine has a total of 1 to 3 substituents. and wherein the substituent is substituted with either of the carbons adjacent to the carbon bonded to the C=X group. is not present on any carbon atom, and at least one and at most three substituents are optionally substituted C4-C6 alkyl; C1-C6 alkylthio [wherein the alkylthio is -NH2, -OH, -NO2, - CN, -SH, CO2C1-C4 alkyl, -CONH2, SF5, -SO2NH2, C 1-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl, C5-C6 cyclo alkenyl, C2-C4 alkynyl, -NH(C1-C6 alkyl), -N(C1-C 6 alkyl)2, N-C1-C4 alkanoylamino, C1-C4 alkoxy, C1-C 4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C3- C4 cycloalkoxy, C5-C6 cycloalkenyloxy, C1-C4 alkoxyalkane C2-C4 alkenyloxycarbonyl, C2-C4 alkynyloxycarbonyl C6-aryloxycarbonyl, C 10 -aryloxycarbonyl, C 14 -a C1-C4 alkanoyl, C2-C4 alkenylcarbonyl, C2-C4 alkynylcarbonyl, C6-arylcarbonyl, C 10 -arylcarbo Nill, C 14 -arylcarbonyl, C1-C4 alkylthio, C1-C4 haloalkyl Thio, C3-C4 cycloalkylthio, C2-C4 alkenylthio, C5-C6 cycloa Alkenylthio, C2-C4 alkynylthio, C1-C4 alkylsulfinyl, C1-C 4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl Sulfonyl, -SO2-NH(C1-C6 alkyl), -SO2-N(C1-C6 alkyl C1-C4 alkylphosphinyl, C1-C4 alkylphosphonyl, N-C1- C4 alkylaminocarbonyl, N,N-di-C1-C4 alkylaminocarbonyl, N -C1-C4 alkanoylaminocarbonyl, N-C1-C4 alkanoyl-N-C1- C4 alkylaminocarbonyl, C6 aryl, C 10 -aryl, C 14 -aryl , C6-aryloxy, C10 -aryloxy, C 14 -aryloxy, benzyl , benzyloxy, benzylthio, C6-arylthio, C 10 -arylthio, C 14 -arylthio, C6-arylamino, C 10 -arylamino, C 14 -Arria amino, benzylamino, heterocyclyl, heteroaryl and trialkylsilyl, double Substituents attached via a bond (e.g., C1-C4-alkylidene (e.g., methyl) from the group consisting of phenylene or ethylidene, oxo, imino and substituted imino groups and C4-C6 haloalkylthio, C4-C6 haloa, which may be substituted in any case. Alkoxy, C4-C6 alkoxy, C4-C6 haloalkyl, C3-C6 cycloalkyl , C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C6 cyclo Alkyl sulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkenyl alkylsulfonyl, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl C2-C6 alkenylsulfanyl, C2-C6 alkenylsulfinyl, C2- C6 alkenylsulfonyl, C2-C6 alkynylsulfanyl, C2-C6 alkynyl Sulfinyl, C2-C6 alkynylsulfonyl, phenylsulfanyl, phenylsulf phenyl, phenylsulfonyl, heterocyclylsulfanyl, heterocyclylsulfinyl heterocyclylsulfonyl, heteroarylsulfanyl, heteroarylsulf S-C1-C6 alkylsulfinimidoyl, heteroarylsulfonyl, S-C1-C6 alkylsulfinimidoyl, S -C3-C6 cycloalkylsulfinimidoyl, S-C2-C6 alkenylsulfi S-C2-C6 alkynylsulfinimidoyl, S-phenylsulfinimidoyl S-Heterocyclylsulfinimidoyl, S-Heteroarylsulfinimidoyl S-C1-C6 alkylsulfonimidoyl, S-C3-C6 cycloalkanol Alkenylsulfonimidoyl, S-C2-C6 Alkenylsulfonimidoyl, S-C2-C 6-Alkynylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclyl S-heteroarylsulfonimidoyl, -NH(C1-C6 alkylsulfonimidoyl), ... alkyl), -N(C1-C6 alkyl)2, -NHCO-C1-C6 alkyl, -N(C -C1-C6 alkyl)CO-C1-C6 alkyl, -N(C3-C6 cycloalkyl)CO -C1-C6 alkyl, -NHCO-phenyl, -N(C1-C6 alkyl)CO-phenyl -N(C3-C6 cycloalkyl)CO-phenyl, -NHCO-C3-C6 cycloalkyl -C1-C6 alkyl, -N(C1-C6 alkyl)CO-(C3-C6 cycloalkyl), -N( C3-C6 cycloalkyl)CO-(C3-C6 cycloalkyl), -NHCO-hetero Aryl, -N(C1-C6 alkyl)CO-heteroaryl, -N(C3-C6 cyclo -NHCO-heteroaryl, -N(C1-C6 alkyl)CO-heteroaryl -N(C3-C6 cycloalkyl)CO-heterocyclyl, -N(C3-C6 cycloalkyl)CO-heterocyclyl , -CO2C1-C6 alkyl, -CONH(C1-C6 alkyl), -CON(C1- C6 alkyl), -CONH(C3-C6 cycloalkyl), -CON(C1-C6 alkyl) -CON(C3-C6 cycloalkyl), -CON(C3-C6 cycloalkyl) CONH-phenyl, -CON(C1-C6 alkyl)phenyl, -CON(C3-C6 -CONH-cycloalkyl)phenyl, -CONH-heteroaryl, -CON(C1-C6 alkyl -CON(C3-C6 cycloalkyl)heteroaryl, -CON(C3-C6 cycloalkyl)heteroaryl, -CON H-heterocyclyl, -CON(C1-C6 alkyl)heterocyclyl, -CON(C3 -C6 cycloalkyl)heterocyclyl, -C(=NOC1-C6 alkyl)H, -C( =NOC1-C6 alkyl)-C1-C6 alkyl, -NHSO2-C1-C6 alkyl , -N(C1-C6 alkyl)SO2-C1-C6 alkyl, -N(C3-C6 cycloa -NHSO2-phenyl, -N(C1-C6 alkyl)SO2-C1-C6 alkyl, -NHSO2-phenyl, -N(C1-C6 alkyl -N(C3-C6 cycloalkyl)SO2-phenyl, -N(C3-C6 cycloalkyl)SO2-phenyl, -NH SO2-C3-C6 cycloalkyl, -N(C1-C6 alkyl)SO2-(C3-C6 cycloalkyl), -N(C3-C6 cycloalkyl)SO2-(C3-C6 cycloalkyl alkyl), -NHSO2-heterocyclyl, -N(C1-C4 alkyl)SO2-heterocyclyl -N(C3-C6 cycloalkyl)SO2-heterocyclyl, -NHSO2-heterocyclyl Heteroaryl, -N(C1-C6 alkyl)SO2-heteroaryl, -N(C3-C6 Cycloalkyl)SO2-heteroaryl, -SO2NH(C1-C6 alkyl), -S O2N(C1-C6 alkyl)2, -SO2N(C1-C6 alkyl)(C3-C6 cyclo -SO2NH(C3-C6 cycloalkyl), -SO2N(C3-C6 cycloalkyl) -SO2NH(phenyl), -SO2N(C1-C6 alkyl)(phenyl) -phenyl), -SO2N(C1-C4 cycloalkyl)(phenyl), -SO2NH(heteroalkyl)(phenyl) -SO2N(C1-C6 alkyl)(heteroaryl), -SO2N(C 3-C6 cycloalkyl) (heteroaryl), -SO2NH (heterocyclyl), -S -ON(C1-C4 alkyl)(heterocyclyl), -SON(C3-C6 cycloalkenyl) (heterocyclyl); and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from halogen, -CN, and optionally substituted C1-C6 alkyl. , C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy and an optionally substituted 4- to 6-membered saturated or partially unsaturated heterocyclic ring; and -SO2NH2; independently selected from Group A consisting of: The remaining 1 to 2 optional substituents are Halogen, hydroxy, -NH2, -CN, -SF5, -COOH, -CONH2, -N O2 and C1-C6 alkyl, C3-C6 cycloalkyl, optionally substituted in either case , C3-C6 cycloalkyl-C1-C6 alkyl, C1-C6 haloalkyl, C1-C 6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl sulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1- C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, phenylsulfa -nyl, phenylsulfinyl, phenylsulfonyl, -NH(C1-C6 alkyl), - N(C1-C6 alkyl)2, -NHCO-C1-C6 alkyl, -N(C1-C6 alk (C1-C6 alkyl), -NHCO-phenyl, -CO2C1-C6 alkyl , -CONH(C1-C6 alkyl), -CON(C1-C6 alkyl)2, -CONH (C3-C6 cycloalkyl), -CON(C1-C6 alkyl)(C3-C6 cycloa -C(=NOC1-C6 alkyl), -C(=NOC1-C6 alkyl)H, -C(=NOC1-C6 alkyl)- C1-C6 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from halogen, -CN, and optionally substituted C1-C6 alkyl. , each independently selected from the group consisting of C1-C6 haloalkyl and C1-C6 alkoxy; optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, ... each independently selected from Group B consisting of: Or, R 2 is naphthyl, wherein the naphthyl is Halogen, hydroxy, -CN, -COOH, -CONH2, -NO2, -SF5, -N H2, and C1-C6 alkyl, C3-C6 cycloalkyl, optionally substituted in either case , C3-C6 cycloalkyl-C1-C6 alkyl, C1-C6 haloalkyl, C1-C 6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl C1-C6 alkylsulfonyl, C3-C6 cycloalkylsulfanily C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C 1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloal phenylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, -NH(C1-C6 alkyl), -N(C1-C6 alkyl)2, -NHCO-C1-C 6 alkyl, -N(C1-C6 alkyl)CO-C1-C6 alkyl, -NHCO-phenyl nyl, -CO2C1-C6 alkyl, -CONH(C1-C6 alkyl), -CON(C 1-C6 alkyl)2, -C(=NOC1-C6 alkyl)H, -C(=NOC1-C6 alkyl)-C1-C6 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from halogen, -CN, and optionally substituted C1-C6 alkyl. , each independently selected from the group consisting of C1-C6 haloalkyl and C1-C6 alkoxy; optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, ... and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is a 4- to 10-membered saturated and partially unsaturated heterocyclyl, a 5-membered heteroaryl, a heterocyclic ring selected from the group consisting of 9-membered heteroaryl and 10-membered heteroaryl; where these are, respectively, Halogen, =O (oxo), hydroxy, -CN, -COOH, -CONH2, -NO2 , -SF5, -NH2, and C1-C6 alkyl, C3-C6 cycloalkyl, optionally substituted in either case , C3-C6 cycloalkyl-C1-C6 alkyl, C1-C6 haloalkyl, C1-C 6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl C1-C6 alkylsulfonyl, C3-C6 cycloalkylsulfanily C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C 1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloal phenylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, -NH(C1-C6 alkyl), -N(C1-C6 alkyl)2, -NHCO-C1-C 6 alkyl, -N(C1-C6 alkyl)CO-C1-C6 alkyl, -NHCO-phenyl nyl, -CO2C1-C6 alkyl, -CONH(C1-C6 alkyl), -CON(C 1-C6 alkyl)2, -C(=NOC1-C6 alkyl)H, -C(=NOC1-C6 alkyl)-C1-C6 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from halogen, -CN, and optionally substituted C1-C6 alkyl. , each independently selected from the group consisting of C1-C6 haloalkyl and C1-C6 alkoxy; optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, ... and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is C1-C6 alkyl, C3-C6 cycloalkyl, or haloalkyl or C1-C6 haloalkyl; R 3a , R 3b are independently hydrogen; halogen; -CN; C1-C6 alkyl [where The alkyl is halogen, hydroxy, -CN, -COOH, -CONH2, -NO2 , -NH2, C1-C6 alkyl which may be substituted in either case, C3-C6 silyl Chloroalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkyls sulfinyl, C1-C6 alkylsulfonyl, -NH(C1-C6 alkyl), -N(C 1-C6 alkyl)2, -NHCO-C1-C6 alkyl, -N(C1-C6 alkyl) CO-C1-C6 alkyl, -CO2C1-C6 alkyl, -CONH(C1-C6 alkyl) 1 to 3 independently selected from the group consisting of -CON(C1-C6 alkyl) and -CON(C1-C6 alkyl) optionally substituted by a substituent selected from the group consisting of C3-C6 cycloalkyl; Optionally substituted C1-C6 haloalkyl; optionally substituted C2-C6 alkene Optionally substituted C2-C6 haloalkenyl; Optionally substituted C2-C 6 alkynyl; benzyl [wherein the phenyl substituents are halogen, hydroxy, -CN , -COOH, -CONH2, -NO2, -NH2, -SF5, in either case, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, Select from the group consisting of C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl each of which may be substituted with 1 to 5 independently selected substituents; heterocyclyl-C 1-C6 alkyl, wherein the heterocyclyl substituent is a 4- to 10-membered saturated and partially unsaturated Selected from the group consisting of saturated heterocyclyl, 5-membered heteroaryl, and 6-membered heteroaryl where these are halogen, ═O (oxo), hydroxy, —CN, -COOH, -CONH2, -NO2, -NH2, which may be substituted in any case 1 to 6 alkyl groups independently selected from the group consisting of C1-C6 alkyl and C1-C6 alkoxy; phenyl, wherein the phenyl is optionally substituted with halogen, hydroxybenzoate ... hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2, -SF5, any optionally substituted C1-C6 alkyl, C1-C6 alkoxy, C1-C 6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl and optionally substituted with 1 to 5 substituents each independently selected from the group consisting of: heterocyclyl, wherein the heterocyclyl substituent is a 4- to 10-membered saturated and partially Selected from the group consisting of unsaturated heterocyclyl, 5-membered heteroaryl, and 6-membered heteroaryl. wherein these are selected from halogen, ═O (oxo), hydroxy, -CN, , -COOH, -CONH2, -NO2, -NH2, even if substituted in any case 1 independently selected from the group consisting of C1-C6 alkyl and C1-C6 alkoxy and optionally substituted with up to 3 substituents; Or, R 3a , R 3b together with the carbon to which they are attached form a C3-C6-carbocyclic ring system or Forming a 3- to 6-membered heterocyclic ring system, wherein the ring system is substituted with halogen, -CN, optionally substituted C1-C6 alkyl, C1-C6 alkoxy and C1-C6 substituted with 1 to 2 substituents independently selected from the group consisting of haloalkoxy; It's okay to be there; R 4 is pyridine, pyrimidine, pyrazine, pyridazine or a 5-membered heteroaryl wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is Halogen, hydroxy, -CN, -COOH, -CO2-C1-C6 alkyl, -SO2 NH2, -CONH2, -CSNH2, -NO2, -NH2, in either case, Optionally, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl , C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1- C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio O, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C3- C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 Cycloalkylsulfonyl, C2-C4 alkenylsulfanyl, C2-C4 alkenyl sulfinyl, C2-C4 alkenylsulfonyl, C2-C4 alkynylsulfanyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, phenylsulf phenyl, phenylsulfinyl, phenylsulfonyl, S-C1-C6 alkylsulfonyl S-C3-C6 Cycloalkylsulfinimidoyl, S-C2-C6 Alkylsulfinimidoyl S-C2-C6 alkynylsulfinimidoyl, S- Phenylsulfinimidoyl, S-C1-C6 Alkylsulfonimidoyl, S-C3 -C6 cycloalkylsulfonimidoyl, S-C2-C6 alkenylsulfonimidoyl S-C2-C6 alkynylsulfonimidoyl, S-phenylsulfonimidoyl, -NH(C1-C6 alkyl), -N(C1-C6 alkyl)2, -NHCO-C1-C 6 alkyl, -N(C1-C6 alkyl)CO-C1-C6 alkyl, -N(C3-C6 -cycloalkyl)CO-C1-C6 alkyl, -NHCO-C3-C6 cycloalkyl, -N(C1-C6 alkyl)CO-(C3-C6 cycloalkyl), -N(C3-C6 cycloalkyl) -C3-C6 cycloalkyl)CO-(C3-C6 cycloalkyl), -N(C1-C6 alkyl)CO -phenyl, -N(C3-C6 cycloalkyl)CO-phenyl, -NHCO-phenyl , -N(CO-C1-C6 alkyl)2, -N(CO-C3-C6 cycloalkyl)2, -N(CO-phenyl)2, -N(CO-C3-C6 cycloalkyl)(CO-C1-C 6 alkyl), -N(CO-C3-C6 cycloalkyl)(CO-phenyl), -N(C O-C1-C6 alkyl)(CO-phenyl), -CONH(C1-C6 alkyl), - CON(C1-C6 alkyl)2, -CONH(C3-C6 cycloalkyl), -CON (C1-C6 alkyl)(C3-C6 cycloalkyl), -CON(C3-C6 cycloa alkyl)2, -CONH-SO2-C1-C6 alkyl, -CONH-SO2-phenyl , -CONH-SO2-(C3-C6 cycloalkyl), -CON(C1-C6 alkyl )-SO2-C1-C6 alkyl, -CON(C1-C6 alkyl)-SO2-phenyl , -CON(C1-C6 alkyl)-SO2-(C3-C6 cycloalkyl), -CON H-phenyl, -CON(C1-C6 alkyl)phenyl, -CON(C3-C6 cyclo alkyl)phenyl, -N(SO2C1-C6 alkyl)2, -N(SO2C1-C6 hal cycloalkyl)2, -N(SO2C3-C6 cycloalkyl)2, -N(SO2C1-C6 alkyl)SO2-phenyl, -N(SO2C3-C6 cycloalkyl)SO2-phenyl -NHSO2-C1-C6 alkyl, -NHSO2-C1-C6 haloalkyl, -N (C1-C6 alkyl)SO2-C1-C6 alkyl, -N(C3-C6 cycloalkyl )SO2-C1-C6 alkyl, -NHSO2-phenyl, -N(C1-C6 alkyl) SO2-phenyl, -N(C3-C6 cycloalkyl)SO2-phenyl, -NHSO2 -C3-C6 cycloalkyl, -N(C1-C6 alkyl)SO2-(C3-C6 cyclo alkyl), -N(C3-C6 cycloalkyl)SO2-(C3-C6 cycloalkyl) , -SO2NH(C1-C6 alkyl), -SO2N(C1-C6 alkyl)2, -SO 2N(C1-C6 alkyl)(C3-C6 cycloalkyl), -SO2NH(C3-C6 cycloalkyl), -SO2N(C3-C6 cycloalkyl)2, -SO2NH(phenyl -SO2N(C1-C6 alkyl)(phenyl), -SO2N(C1-C4 cyclo alkyl)(phenyl), -C(=NOC1-C6 alkyl)H and -C(=NOC1- C6 alkyl)-C1-C6 alkyl may be used; R 5 is hydrogen, halogen, -CN or optionally substituted C1 -C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxy C(O)-, (C1-C6 alkoxy)2CH-, -CO2C1-C6 alkyl, - CONH(C1-C6 alkyl), -CON(C1-C6 alkyl)2, -NHCO-C 1-C6 alkyl, -N(C1-C6 alkyl)CO-C1-C6 alkyl, -C(=N -OC(=NOC1-C6 alkyl)H or -C(=NOC1-C6 alkyl)-C1-C6 alkyl It is a kill. The present invention provides a compound represented by the formula:
[0009] The compounds of formula (I) may further be prepared by reacting any diastereomers or enantiomers that exist. and N-oxomers and E / Z isomers, as well as salts and N-oxomers of the compounds of formula (I). The present invention also includes the use of insecticides and their applications for controlling pests.
[0010] Preferred definitions of radicals for the formulae specified above and below are as follows: Please see below. DETAILED DESCRIPTION OF THE INVENTION
[0011] Preferred is (Configuration 2-1), formula (I) [wherein, X is O or S; Q 1 and Q 2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or CH; R 1 is hydrogen; C1-C6 alkyl [wherein the alkyl is -CN, -CONH2, Substituted with one substituent selected from -COOH, -NO2 and -Si(CH3)3 C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl C2-C6 alkynyl;C2-C6 haloalkynyl;C3-C4 cycloalkyl-C 1-C2 alkyl- [wherein the C3-C4 cycloalkyl is substituted with one or two halogen atoms] oxetan-3-yl-CH2-; or benzyl [which may be substituted with an atom]; wherein the benzyl may be substituted with halogen or C1-C3 haloalkyl. can be; R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine is substituted with 1 to 5 substituents. provided that at least one substituent is adjacent to the carbon bonded to the C=X group. and the substituents are halogen, hydroxy, -N H2, -CN, -SF5, -COOH, -CONH2, -NO2, C1-C6 alkyl, Optionally substituted C3-C6 cycloalkyl; C3-C6 cycloalkyl-C1-C 6 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfinyl sulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfonyl C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 Haloalkylsulfinyl, C1-C3 haloalkylsulfonyl; Phenylsulfanyl , phenylsulfinyl, phenylsulfonyl [wherein, in either case, the phenyl is selected from the group consisting of halogen, CN, C1-C6 alkyl, and C1-C3 haloalkyl -NH(C1-C4 alkyl), - N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alk -NHCO-phenyl, wherein the phenyl is a halo selected from the group consisting of aryl, CN, C1-C6 alkyl, and C1-C3 haloalkyl optionally substituted with 1 to 2 substituents]; -CO2C1-C4 alkyl, -CONH( C1-C4 alkyl), -CON(C1-C4 alkyl)2, -CONH(C3-C6 alkyl) cycloalkyl), -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -C (=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alk alkyl; phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl Aryl is halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C substituted with 1 to 2 substituents independently selected from the group consisting of 1-C4 alkoxy; each independently selected from the group consisting of: Or, R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine has a total of 1 to 3 substituents. and wherein the substituent is substituted with either of the carbons adjacent to the carbon bonded to the C=X group. and at least one and at most three substituents are C1-C6 alkyl. Alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3- C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 Cycloalkylsulfonyl, C1-C3 haloalkylsulfinyl, C1-C3 haloal Phenylsulfonyl; phenylsulfanyl, phenylsulfinyl, phenylsulfonyl [ In each case, the phenyl may be selected from halogen, —CN, C1-C6 alkyl, and may be substituted with 1 to 2 substituents selected from the group consisting of C1-C3 haloalkyl optionally substituted C3-C6 cycloalkyl; -NH(C1-C4 alkyl) , -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl; -NHCO-phenyl, wherein the phenyl is Selected from the group consisting of halogen, CN, C1-C6 alkyl, and C1-C3 haloalkyl -CO2C1-C4 alkyl, -CON H(C1-C4 alkyl), -CON(C1-C4 alkyl), -CONH(C3-C 6 cycloalkyl), -CON(C1-C4 alkyl)(C3-C6 cycloalkyl), -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl; phenyl and 5- to 6-membered heteroaryl [wherein the phenyl or 5- to 6-membered heteroaryl Heteroaryl includes halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl, each independently selected from the group consisting of C1-C4 alkoxy and C1-C4 haloalkoxy; independently selected from Group A consisting of: The remaining 1 to 2 optional substituents are halogen, hydroxy, -NH2, -CN, -SF5, -COOH, -CONH2, -NO2, C1-C6 alkyl, optionally substituted C3 -C6 cycloalkyl; C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 ha C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio O, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C3 halo Alkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl phenylsulfanyl, phenylsulfinyl, phenylsulfonyl [wherein In this case, the phenyl is selected from halogen, CN, C1-C6 alkyl and C1-C3 halo. -NH(, optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl; C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl -NHCO-phenyl wherein the phenyl is selected from halogen, CN, C1-C6 alkyl and C1-C3 haloalkyl. and optionally substituted with 1 to 2 substituents selected from the group consisting of: 4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -CONH(C3-C6 cycloalkyl), -CON(C1-C4 alkyl)(C3-C 6 cycloalkyl), -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl) phenyl and 5-6 membered heteroaryl [wherein the phenyl Phenyl or 5-6 membered heteroaryl is halogen, -CN, C1-C6 alkyl, C1 -C3 haloalkyl and C1-C4 alkoxy, and each independently selected from group B consisting of: ; Or, R 2 is naphthyl, wherein the naphthyl is selected from halogen, hydroxy, -CN, - COOH, -CONH2, -NO2, -SF5, -NH2, C1-C6 alkyl, substituted C3-C6 cycloalkyl, optionally alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C 1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloa alkylsulfinyl, C1-C3 haloalkylsulfonyl; phenylsulfanyl, phenyl phenylsulfinyl, phenylsulfonyl (wherein, in either case, the phenyl is halo-, is selected from the group consisting of halogen, CN, C1-C6 alkyl, and C1-C3 haloalkyl and optionally substituted by 1 to 2 substituents; -NH(C1-C4 alkyl), -N(C 1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl) -CO-C1-C4 alkyl; -NHCO-phenyl, wherein the phenyl is selected from the group consisting of halogen, 1 to 2 selected from the group consisting of CN, C1-C6 alkyl, and C1-C3 haloalkyl -CO2C1-C4 alkyl, -CONH(C1- C4 alkyl), -CON(C1-C4 alkyl)2, -C(=NOC1-C4 alkyl) )H, -C(=NOC1-C4 alkyl)-C1-C4 alkyl; phenyl and 5-6 membered wherein the phenyl or 5- to 6-membered heteroaryl is selected from the group consisting of halogen, - consisting of CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy each of which may be substituted with 1 to 2 substituents independently selected from the group and optionally substituted with 1 to 3 substituents independently selected from: Or, R 2 is a 4- to 10-membered saturated and partially unsaturated heterocyclyl, a 5-membered heteroaryl, a heterocyclic ring selected from the group consisting of 9-membered heteroaryl and 10-membered heteroaryl; where these are halogen, ═O (oxo), hydroxy, —CN, -COOH, -CONH2, -NO2, -SF5, -NH2, C1-C6 alkyl, substituted C3-C6 cycloalkyl, optionally substituted; C3-C6 cycloalkyl-C1-C6 alkyl alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfo Nyl, C3-C6 cycloalkylsulfanyl, C3-C6 cycloalkylsulfinyl , C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 halo Alkyl sulfinyl, C1-C3 haloalkylsulfonyl; phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, wherein in each case, the phenyl is Selected from the group consisting of halogen, CN, C1-C6 alkyl, and C1-C3 haloalkyl -NH(C1-C4 alkyl), -N( C1-C4 alkyl), -NHCO-C1-C4 alkyl, -N(C1-C4 alkyl) )CO-C1-C4 alkyl; -NHCO-phenyl, wherein the phenyl is a halogen atom; , CN, C1-C6 alkyl, and C1-C3 haloalkyl 2 substituents]; -CO2C1-C4 alkyl, -CONH(C1 -C4 alkyl), -CON(C1-C4 alkyl)2, -C(=NOC1-C4 alkyl -C(=NOC1-C4 alkyl)-C1-C4 alkyl; phenyl and 5-6 phenyl or 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl is halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy and each of the groups may be substituted with 1 to 2 substituents independently selected from the group consisting of optionally substituted with 1 to 3 substituents independently selected from the group; Or, R 2 is C1-C6 alkyl, wherein the alkyl is C1-C3 alkoxy- , C1-C3 haloalkoxy-, C1-C6 alkylthio, C1-C6 alkylsulfi C1-C6 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloa alkylsulfinyl, C1-C3 haloalkylsulfonyl; phenyl and 5-6 membered heteroalkylsulfonyl wherein the phenyl or 5- to 6-membered heteroaryl is selected from halogen, —CN, from the group consisting of C1-C6 alkyl, C1-C3 haloalkyl, and C1-C4 alkoxy each of which may be substituted with 1 to 2 independently selected substituents]; C3-C6 cyclohexane cycloalkyl [wherein the cycloalkyl is a halogen, —CN, —COOH, —CONH 2. C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1- C6 alkoxy, -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl) and -CON(C1-C4 alkyl)2 optionally substituted with one substituent selected from the group consisting of C1-C6 haloalkyl; It is; R 3a , R 3b are independently hydrogen; halogen; -CN; C1-C6 alkyl [where The alkyl is hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2 , C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C 4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyl sulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1- C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, -NH(C1-C 4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N (C1-C4 alkyl)CO-C1-C4 alkyl, -CO2C1-C4 alkyl, -C Select independently from the group consisting of -ONH(C1-C4 alkyl) and -CON(C1-C4 alkyl) optionally substituted with 1 to 3 substituents independently selected from the group consisting of C3-C6 cycloalkyl; wherein the cycloalkyl is halogen, —CN, —COOH, —CONH 2 , C 1 — C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy oxy, C1-C6 haloalkoxy, -CO2C1-C4 alkyl, -CONH(C1-C 1 to 2 selected from the group consisting of -CON(C1-C4 alkyl) and -CON(C1-C4 alkyl) optionally substituted by a substituent group; C1-C6 haloalkyl, wherein the haloalkyl is , hydroxy, -CN, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 Haloalkoxy, -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl) and -CON(C1-C4 alkyl)2 C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkyl C2-C6 haloalkynyl; benzyl wherein the phenyl substituent is selected from the group consisting of halogen, Hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2, -SF5, C1 -C6 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C4 haloal Coxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkyl C1-C3 haloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl and C1-C3 haloalkylsulfonyl heterocyclyl-C1-C6 alkyl [wherein the heterocyclyl Heterocyclyl substituents include 4- to 10-membered saturated and partially unsaturated heterocyclyl, 5-membered heterocyclyl, and 6-membered heteroaryl, each of which is selected from the group consisting of: Halogen, ═O (oxo), hydroxy, -CN, -COOH, -CONH2, -N O2, -NH2, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy and optionally substituted with 1 to 3 substituents independently selected from the group consisting of phenyl, wherein the phenyl is selected from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH2 , -NO2, -NH2, -SF5, C1-C6 alkyl, C1-C3 haloalkyl, C1 -C4 alkoxy, C1-C4 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyl alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C From the group consisting of 1-C3 haloalkylsulfinyl and C1-C3 haloalkylsulfonyl and heterocyclic groups each independently selected from 1 to 5 substituents; Cyclyl [wherein the heterocyclyl substituent is a 4- to 10-membered saturated and partially unsaturated heterocyclyl] selected from the group consisting of tetracyclyl, 5-membered heteroaryl, and 6-membered heteroaryl; where these are halogen, ═O (oxo), hydroxy, -CN, and -COO, respectively. H, -CONH2, -NO2, -NH2, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy, may be selected from the group consisting of; Or, R 3a , R 3b together with the carbon to which they are attached form a C3-C6-carbocyclic ring system or Form a 3-6 membered heterocyclic ring system, wherein the ring system is substituted with halogen, -CN, C1-C6 Alkyl, C1-C3 haloalkyl, C1-C4 alkoxy and C1-C3 haloalkoxy optionally substituted with 1 to 2 substituents independently selected from the group consisting of R 4 is pyridine, pyrimidine, pyrazine, pyridazine or a 5-membered heteroaryl wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is Halogen, hydroxy, -CN, -COOH, -CONH2, -CSNH2, -NO2, -NH2, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio, C1-C 6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C3 haloalkylthio , C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, -NH( C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl -NHCO-C3-C6 cycloalkyl; -NHCO-phenyl [wherein the phenyl The alkyl group is selected from the group consisting of halogen, CN, C1-C6 alkyl, and C1-C3 haloalkyl. -N(C1-C4 alkyl)CO -C1-C4 alkyl, -N(C1-C4 alkyl)CO-C3-C6 cycloalkyl; -N(C1-C4 alkyl)CO-phenyl, wherein the phenyl is selected from the group consisting of halogen, -CN 1 to 2 substituents selected from the group consisting of C1-C6 alkyl and C1-C3 haloalkyl optionally substituted with a substituent]; -N(SO2C1-C3 alkyl)2, -NH(SO2 C1-C3 alkyl), -N(C1-C4 alkyl)(SO2C1-C3 alkyl), - CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 -C(=NOC1-C4 alkyl)H and -C(=NOC1-C4 alkyl) and (C1-C4 alkyl)-, and often; R 5 is hydrogen, halogen, -CN, C1-C3 alkyl, C1-C3 haloalkyl, C 3-C4 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C 3AlkoxyC(O)-, (C1-C3alkoxy)2CH-, -CO2C1-C4alkoxy alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NH CO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, - C(=NOC1-C4 alkyl)H or -C(=NOC1-C4 alkyl)-C1-C4 alkyl] It is a compound represented by the formula:
[0012] Similarly preferred is (Configuration 2-2), formula (I) [wherein, X is O or S; Q 1 and Q 2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or CH; R 1 is hydrogen; C1-C6 alkyl [wherein the alkyl is -CN, -CONH2, Substituted with one substituent selected from -COOH, -NO2 and -Si(CH3)3 C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl C2-C6 alkynyl;C2-C6 haloalkynyl;C3-C4 cycloalkyl-C 1-C2 alkyl- [wherein the C3-C4 cycloalkyl is substituted with one or two halogen atoms] oxetan-3-yl-CH2-; or benzyl [which may be substituted with an atom]; wherein the benzyl may be substituted with halogen or C1-C3 haloalkyl. can be; R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine is substituted with 1 to 5 substituents. provided that at least one substituent is adjacent to the carbon bonded to the C=X group. and the substituent is present on any carbon atom of Halogen, hydroxy, -NH2, -CN, -SF5, -COOH, -CONH2, -N O2, C1-C6 alkyl, optionally substituted C3-C6 cycloalkyl; C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 Alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl Sulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkylsulfanyl , C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1 -C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkyl sulfonyl; Phenylsulfanyl, phenylsulfinyl, phenylsulfonyl [wherein any of In some cases, the phenyl may be selected from halogen, CN, C1-C6 alkyl, and C1-C3 haloal. optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl; -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C 4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl; -NHCO-phenyl, wherein the phenyl is selected from the group consisting of halogen, CN, C1-C6 alkyl and and C1-C3 haloalkyl, good]; -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C 4 alkyl), -CONH(C3-C6 cycloalkyl), -CON(C1-C4 alkyl) -C(=NOC1-C4 alkyl)H, -C(= NOC1-C4 alkyl)-C1-C4 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl groups include halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C 4 alkoxy, each of which is substituted with 1 to 2 substituents independently selected from the group consisting of [May be] each independently selected from the group consisting of: Or, R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine has a total of 1 to 3 substituents. and wherein the substituent is substituted with either of the carbons adjacent to the carbon bonded to the C=X group. is not present on any carbon atom, and at least one and at most three substituents are C4-C6-Alkyl, C1-C6 Alkylthio, C1-C6 Alkylsulfinyl, C 1-C6 alkylsulfonyl, C3-C6 cycloalkylsulfanyl, C3-C6 cyclo C3-C6 cycloalkylsulfonyl, C1-C3 haloalkylsulfinyl, sulfinyl, C1-C3 haloalkylsulfonyl; Phenylsulfanyl, phenylsulfinyl, phenylsulfonyl [wherein any of In some cases, the phenyl may be selected from halogen, CN, C1-C6 alkyl, and C1-C3 haloal. optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl; optionally substituted C3-C6 cycloalkyl; -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C 4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, -NHCO-C3 -C4 cycloalkyl, -NHSO2-phenyl; -NHCO-phenyl, wherein the phenyl is selected from the group consisting of halogen, -CN, C1-C6 alkyl, and substituted with 1 to 2 substituents selected from the group consisting of C1-C3 haloalkyl may also]; -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C 4 alkyl), -CONH(C3-C6 cycloalkyl), -CON(C1-C4 alkyl) -C(=NOC1-C4 alkyl)H, -C(= NOC1-C4 alkyl)-C1-C4 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl groups are halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 1 independently selected from the group consisting of alkoxy and C1-C4 haloalkoxy may be substituted with up to 2 substituents] independently selected from Group A consisting of: The remaining 1 to 2 optional substituents are Halogen, hydroxy, -NH2, -CN, -SF5, -COOH, -CONH2, -N O2, C1-C6 alkyl, optionally substituted C3-C6 cycloalkyl; C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 Alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl Sulfinyl, C1-C6 alkylsulfonyl, C1-C3 haloalkylthio, C1-C 3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl; Phenylsulfanyl, phenylsulfinyl, phenylsulfonyl [wherein any of In some cases, the phenyl may be selected from halogen, CN, C1-C6 alkyl, and C1-C3 haloal. optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl; -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C 4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl; -NHCO-phenyl, wherein the phenyl is selected from the group consisting of halogen, CN, C1-C6 alkyl and and C1-C3 haloalkyl, good]; -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C 4 alkyl), -CONH(C3-C6 cycloalkyl), -CON(C1-C4 alkyl) -C(=NOC1-C4 alkyl)H, -C(= NOC1-C4 alkyl)-C1-C4 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl groups include halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C 4 alkoxy, each of which is substituted with 1 to 2 substituents independently selected from the group consisting of [May be] each independently selected from Group B consisting of: Or, R 2 is naphthyl, wherein the naphthyl is Halogen, hydroxy, -CN, -COOH, -CONH2, -NO2, -SF5, -N H2, C1-C6 alkyl, optionally substituted C3-C6 cycloalkyl; C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 Alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl Sulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkylsulfanyl , C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1 -C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkyl sulfonyl; Phenylsulfanyl, phenylsulfinyl, phenylsulfonyl [wherein any of In some cases, the phenyl may be selected from halogen, CN, C1-C6 alkyl, and C1-C3 haloal. optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl; -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C 4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl; -NHCO-phenyl, wherein the phenyl is selected from the group consisting of halogen, CN, C1-C6 alkyl and and C1-C3 haloalkyl, good]; -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C 4 alkyl)2, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl) (C1-C4 alkyl); and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl groups include halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C 4 alkoxy, each of which is substituted with 1 to 2 substituents independently selected from the group consisting of [May be] and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is a 4- to 10-membered saturated and partially unsaturated heterocyclyl, a 5-membered heteroaryl, a heterocyclic ring selected from the group consisting of 9-membered heteroaryl and 10-membered heteroaryl; where these are, respectively, Halogen, =O (oxo), hydroxy, -CN, -COOH, -CONH2, -NO2 , -SF5, -NH2, C1-C6 alkyl, optionally substituted C3-C6 cycloalkyl; C3-C6 cycloalkyl-C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 Alkoxy, C1-C3 haloalkoxy, C1-C6 alkylthio, C1-C6 alkyl Sulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkylsulfanyl , C3-C6 cycloalkylsulfinyl, C3-C6 cycloalkylsulfonyl, C1 -C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkyl sulfonyl; Phenylsulfanyl, phenylsulfinyl, phenylsulfonyl [wherein any of In some cases, the phenyl may be selected from halogen, CN, C1-C6 alkyl, and C1-C3 haloal. optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl; -NH(C1-C4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C 4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl; -NHCO-phenyl, wherein the phenyl is selected from the group consisting of halogen, CN, C1-C6 alkyl and and C1-C3 haloalkyl, good]; -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl), -CON(C1-C 4 alkyl)2, -C(=NOC1-C4 alkyl)H, -C(=NOC1-C4 alkyl) (C1-C4 alkyl); and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl groups include halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C 4 alkoxy, each of which is substituted with 1 to 2 substituents independently selected from the group consisting of [May be] and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is C1-C6 alkyl, wherein the alkyl is C1-C3 alkoxy-, C1-C3 haloalkoxy-, C1-C6 alkylthio, C1 -C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C3 haloalkyl Thio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl; Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl groups include halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C 4 alkoxy, each of which is substituted with 1 to 2 substituents independently selected from the group consisting of may]; C3-C6 cycloalkyl [wherein the cycloalkyl is halogen, -CN, -COO H, -CONH2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl alkyl, C1-C6 alkoxy, -CO2C1-C4 alkyl, -CONH(C1-C4 -CON(C1-C4 alkyl) and -CON(C1-C4 alkyl) and C1-C6 haloalkyl and is substituted with one substituent selected from the group consisting of: R 3a , R 3b are independently hydrogen; halogen; -CN; C1-C6 alkyl [where The alkyl is hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2 , C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C 4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyl sulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1- C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, -NH(C1-C 4 alkyl), -N(C1-C4 alkyl)2, -NHCO-C1-C4 alkyl, -N (C1-C4 alkyl)CO-C1-C4 alkyl, -CO2C1-C4 alkyl, -C Select independently from the group consisting of -ONH(C1-C4 alkyl) and -CON(C1-C4 alkyl) optionally substituted with 1 to 3 substituents independently selected from the group consisting of C3-C6 cycloalkyl; wherein the cycloalkyl is halogen, —CN, —COOH, —CONH 2 , C 1 — C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy oxy, C1-C6 haloalkoxy, -CO2C1-C4 alkyl, -CONH(C1-C 1 to 2 selected from the group consisting of -CON(C1-C4 alkyl) and -CON(C1-C4 alkyl) optionally substituted by a substituent group; C1-C6 haloalkyl, wherein the haloalkyl is , hydroxy, -CN, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 Haloalkoxy, -CO2C1-C4 alkyl, -CONH(C1-C4 alkyl) and -CON(C1-C4 alkyl)2 C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkyl C2-C6 haloalkynyl; benzyl wherein the phenyl substituent is selected from the group consisting of halogen, Hydroxy, -CN, -COOH, -CONH2, -NO2, -NH2, -SF5, C1 -C6 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C4 haloal Coxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkyl C1-C3 haloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl and C1-C3 haloalkylsulfonyl heterocyclyl-C1-C6 alkyl [wherein the heterocyclyl Heterocyclyl substituents include 4- to 10-membered saturated and partially unsaturated heterocyclyl, 5-membered heterocyclyl, and 6-membered heteroaryl, each of which is selected from the group consisting of: Halogen, ═O (oxo), hydroxy, -CN, -COOH, -CONH2, -N O2, -NH2, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy and optionally substituted with 1 to 3 substituents independently selected from the group consisting of phenyl, wherein the phenyl is selected from the group consisting of halogen, hydroxy, -CN, -COOH, -CONH2 , -NO2, -NH2, -SF5, C1-C6 alkyl, C1-C3 haloalkyl, C1 -C4 alkoxy, C1-C4 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyl alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C From the group consisting of 1-C3 haloalkylsulfinyl and C1-C3 haloalkylsulfonyl and heterocyclic groups each independently selected from 1 to 5 substituents; Cyclyl [wherein the heterocyclyl substituent is a 4- to 10-membered saturated and partially unsaturated heterocyclyl] selected from the group consisting of tetracyclyl, 5-membered heteroaryl, and 6-membered heteroaryl; where these are halogen, ═O (oxo), hydroxy, -CN, and -COO, respectively. H, -CONH2, -NO2, -NH2, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy, may be selected from the group consisting of; Or, R 3a , R 3b together with the carbon to which they are attached form a C3-C6-carbocyclic ring system or Form a 3-6 membered heterocyclic ring system, wherein the ring system is substituted with halogen, -CN, C1-C6 Alkyl, C1-C3 haloalkyl, C1-C4 alkoxy and C1-C3 haloalkoxy optionally substituted with 1 to 2 substituents independently selected from the group consisting of R 4 is pyridine, pyrimidine, pyrazine, pyridazine or a 5-membered heteroaryl wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is Halogen, hydroxy, -CN, -COOH, -CO2-C1-C6 alkyl, -CON H2, -CSNH2, -NO2, -NH2, C1-C6 alkyl, C3-C6 cycloalkenyl alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C 1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 halo alkylsulfonyl, -NH(C1-C4 alkyl), -N(C1-C4 alkyl) , -NHCO-C1-C4 alkyl [wherein the alkyl is -CN, C1-C6 alkyl] -NHCO-C1-C4 haloaryl and C1-C4 alkoxy; alkyl, -NHCO-C3-C6 cycloalkyl [wherein the cycloalkyl is a halogen atom or -C1-C6 alkyl or C1-C4 alkoxy. -NHCO-phenyl, wherein the phenyl is optionally substituted with up to two substituents; , halogen, —CN, C1-C6 alkyl, and C1-C3 haloalkyl and optionally substituted by 1 to 2 substituents selected from the group consisting of -N(C1-C4 alkyl)CO- C1-C4 alkyl, -N(C1-C4 alkyl)CO-C3-C6 cycloalkyl;- N(C1-C4 alkyl)CO-phenyl, wherein the phenyl is selected from the group consisting of halogen, CN, C 1 to 2 substituents selected from the group consisting of 1-C6 alkyl and C1-C3 haloalkyl -N(SO2C1-C3 alkyl)2, -NH(SO2C1 -C3 alkyl), -N(C1-C4 alkyl)(SO2C1-C3 alkyl), -N( SO2C1-C3 haloalkyl)2, -NH(SO2C1-C3 haloalkyl), -CO NH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -CONH-SO2 -C1-C3 alkyl, -CON(C1-C4 alkyl)(C3-C6 cycloalkyl) , -CONH(C1-C4 haloalkyl), -CONH(C3-C6 cycloalkyl), -CONH(C3-C6 cyanocycloalkyl), -C(=NOC1-C4 alkyl)H and -C(=NOC1-C4 alkyl)-C1-C4 alkyl; and -CONH-phenyl phenyl, wherein the phenyl is selected from halogen, —CN, C1-C6 alkyl, C1-C3 halo, 1 to 2 independently selected from the group consisting of alkyl and C1-C4 alkoxy and wherein the substituted group is substituted with 1 to 3 substituents selected from the group consisting of It's okay to be there; R 5 is hydrogen, halogen, -CN, C1-C3 alkyl, C1-C3 haloalkyl, C 3-C4 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C 3AlkoxyC(O)-, (C1-C3alkoxy)2CH-, -CO2C1-C4alkoxy alkyl, -CONH(C1-C4 alkyl), -CON(C1-C4 alkyl)2, -NH CO-C1-C4 alkyl, -N(C1-C4 alkyl)CO-C1-C4 alkyl, - C(=NOC1-C4 alkyl)H or -C(=NOC1-C4 alkyl)-C1-C4 alkyl] It is a compound represented by the formula:
[0013] Even more preferable is (Configuration 3-1), formula (I) [wherein, X is O or S; Q 1 and Q2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or CH; R 1 is hydrogen; C1-C3 alkyl [wherein the alkyl is -CN, -CONH2, Substituted with one substituent selected from -COOH, -NO2 and -Si(CH3)3 C1-C3 haloalkyl; C2-C4 alkenyl; C2-C4 haloalkenyl C2-C4 alkynyl;C2-C4 haloalkynyl;C3-C4 cycloalkyl-C 1-C2 alkyl- [wherein the C3-C4 cycloalkyl is substituted with one or two halogen atoms] oxetan-3-yl-CH2-; or benzyl [which may be substituted with an atom]; wherein the benzyl may be substituted with halogen or C1-C3 haloalkyl. can be; R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine is substituted with 1 to 5 substituents. provided that at least one substituent is adjacent to the carbon bonded to the C=X group. and the substituents are halogen, -CN, -NO2 , C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C 4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyl C1-C3 alkylsulfonyl, C3-C4 cycloalkylsulfanily C3-C4 cycloalkylsulfinyl, C3-C4 cycloalkylsulfonyl, C 1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloal phenyl and 5- to 6-membered heteroaryl [wherein the phenyl or 5- to 6-membered heteroaryl is The 6-membered heteroaryl includes halogen, —CN, C1-C3 alkyl, and C1-C3 haloaryl. and optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl, are each independently selected; Or, R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine has a total of 1 to 3 substituents. and wherein the substituent is substituted with either of the carbons adjacent to the carbon bonded to the C=X group. and at least one and at most two substituents are C3-C4 carbon atoms. Chloroalkyl, C1-C4 alkylthio, C1-C3 alkylsulfinyl, C1-C3 Alkyl sulfonyl, C3-C4 cycloalkylsulfanyl, C3-C4 cycloalkoxy C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylsulfonyl phenylsulfanyl, C1-C3 haloalkylsulfonyl; phenylsulfanyl [wherein the phenyl The alkyl group is selected from the group consisting of halogen, -CN, C1-C3 alkyl, or C1-C3 haloalkyl. phenylsulfinyl [wherein The phenyl may be selected from halogen, —CN, C1-C3 alkyl, or C1-C3 haloalkyl. optionally substituted with 1 to 2 substituents selected from the group consisting of: phenylsulfonyl wherein the phenyl is selected from halogen, —CN, C1-C3 alkyl, or C1-C3 haloa. -NHCO, optionally substituted with 1 to 2 substituents selected from the group consisting of alkyl, -phenyl, wherein the phenyl is selected from the group consisting of halogen, CN, C1-C6 alkyl and C1-C 3 haloalkyl]; CONH(C3-C4 cycloalkyl), -CON(C1-C3 alkyl)(C3-C4 cycloalkyl), -C(=NOC1-C3 alkyl)-C1-C3 alkyl; phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl is Halogen, -CN, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 haloa optionally substituted with 1 to 2 substituents selected from the group consisting of alkoxy, selected independently from A; The remaining 1-2 optional substituents are halogen, -CN, -NO2, C1-C6 alkyl, C 3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 Haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C 3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfonyl phenyl and 5-6 membered heteroaryl [wherein The phenyl and 5- to 6-membered heteroaryl are substituted with halogen, —CN, C1-C3 alkyl, or the like. substituted with 1 to 2 substituents selected from the group consisting of alkyl and C1-C3 haloalkyl; each independently selected from Group B consisting of: Or, R 2 are thiophene, furan, pyrazole, thiazole, isothiazole, oxazoline or isoxazole, wherein these are each selected from halogen, hydroxy, -CN, -NO2, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C3 haloa alkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C4 cycloa C3-C4 cycloalkylsulfanyl, C3-C4 cycloalkylsulfinyl, C3-C4 cycloalkylsulfonyl C1-C3 haloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl, C 1-C3 haloalkylsulfonyl; phenyl and 5-6 membered heteroaryl [wherein Phenyl or 5-6 membered heteroaryl is substituted with halogen, -CN, C1-C3 alkyl and may be substituted with 1 to 2 substituents selected from the group consisting of C1-C3 haloalkyl and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is C1-C6 alkyl, wherein the alkyl is C1-C3 alkoxy- , C1-C3 haloalkoxy-, C1-C3 alkylthio, C1-C3 alkylsulfi C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloa alkylsulfinyl, C1-C3 haloalkylsulfonyl; phenyl [wherein the phenyl The alkyl groups are halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkyl. substituted with 1 to 2 substituents independently selected from the group consisting of alkoxy, and optionally substituted with one substituent selected from the group consisting of: R 3a , R 3b are independently hydrogen; C1-C6 alkyl [wherein the alkyl is C 1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkyl Alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyls sulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 Independently from the group consisting of haloalkylsulfinyl and C1-C3 haloalkylsulfonyl optionally substituted with 1 to 3 substituents selected from the group consisting of C3-C6 cycloalkyl; C 1-C6 haloalkyl;C2-C6 alkenyl;C2-C6 haloalkenyl;C2-C6 Alkynyl; C2-C6 haloalkynyl; benzyl wherein the phenyl substituent is a halo Gen, -CN, -NO2, C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 alkyl 1 to 3 substituents independently selected from the group consisting of alkoxy and C1-C4 haloalkoxy or heterocyclyl-C1-C6 alkyl [wherein the Heterocyclyl substituents include 4- to 10-membered heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl. and aryl, each of which is selected from the group consisting of halogen, -CN, , -NO2, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: phenyl, wherein the phenyl is selected from halogen, -CN, -NO2, C1-C6 alkyl, C1 -substituted with one substituent selected from the group consisting of C3 haloalkyl and C1-C4 alkoxy; and optionally substituted; Or, R 3a , R 3b together with the carbon to which they are attached form a cyclopropane ring, a cyclobutane ring, and forming a tetrahydropyran ring, an oxetane ring, or a tetrahydropyran ring, wherein the ring is not substituted with a halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy each of which may be substituted with 1 to 2 substituents independently selected from the group consisting of: R 4 is pyridine, pyrimidine or thiazole, wherein (A) the pyridine or Pyrimidine is substituted with halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkenyl alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfo C1-C3 haloalkylsulfinyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl and C1-C 3 haloalkylsulfonyl, and (B) the thiazole is selected from the group consisting of halogen, —CN, —NO2, C1-C6 alkyl, , C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1- C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1 -C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfonyl 1 to 2 substituted alkylsulfonyl groups selected from the group consisting of phenyl and C1-C3 haloalkylsulfonyl optionally substituted with a group; R 5 is hydrogen, halogen, -CN, C1-C3 alkyl, C1-C3 haloalkyl, C 3-C4 cycloalkyl or C1-C3 alkoxy] It is a compound represented by the formula:
[0014] Likewise, it is even more preferable to (Configuration 3-2), formula (I) [wherein, X is O or S; Q 1 and Q 2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or CH; R 1 is hydrogen; C1-C3 alkyl [wherein the alkyl is -CN, -CONH2, Substituted with one substituent selected from -COOH, -NO2 and -Si(CH3)3 C1-C3 haloalkyl; C2-C4 alkenyl; C2-C4 haloalkenyl C2-C4 alkynyl;C2-C4 haloalkynyl;C3-C4 cycloalkyl-C 1-C2 alkyl- [wherein the C3-C4 cycloalkyl is substituted with one or two halogen atoms] oxetan-3-yl-CH2-; or benzyl [which may be substituted with an atom]; wherein the benzyl may be substituted with halogen or C1-C3 haloalkyl. can be; R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine is substituted with 1 to 5 substituents. provided that at least one substituent is adjacent to the carbon bonded to the C=X group. and the substituent is present on any carbon atom of Halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1- C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxy C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C 4 cycloalkylsulfanyl, C3-C4 cycloalkylsulfinyl, C3-C4 cycloalkylsulfinyl Chloroalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulf vinyl, C1-C3 haloalkylsulfonyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from the group consisting of halogen, -CN, C1-C3 alkyl, and C1-C3 haloalkyl. and optionally substituted with 1 to 2 substituents selected from each independently selected from the group consisting of: Or, R 2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein The phenyl, pyridine, pyrimidine, pyrazine or pyridazine has a total of 1 to 3 substituents. and wherein the substituent is substituted with either of the carbons adjacent to the carbon bonded to the C=X group. and at least one and at most two substituents are C4-alkyl, C3-C4 cycloalkyl, wherein the C3-C4 cycloalkyl is -CN or halogen], C1-C4 alkylthio, C1-C3 alkyl alkylsulfinyl, C1-C3 alkylsulfonyl, C3-C4 cycloalkylsulf anyl, C3-C4 cycloalkylsulfinyl, C3-C4 cycloalkylsulfonyl , C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl; and Phenylsulfanyl, wherein the phenyl is selected from the group consisting of halogen, —CN, C1-C3 alkyl, and substituted with 1 to 2 substituents selected from the group consisting of C1-C3 haloalkyl may also]; Phenylsulfinyl, wherein the phenyl is selected from the group consisting of halogen, —CN, C1-C3 alkyl, and substituted with 1 to 2 substituents selected from the group consisting of C1-C3 haloalkyl may also]; Phenylsulfonyl, wherein the phenyl is selected from halogen, —CN, C1-C3 alkyl and and C1-C3 haloalkyl, good]; -NHCO-phenyl, wherein the phenyl is selected from the group consisting of halogen, CN, C1-C6 alkyl and and C1-C3 haloalkyl, good]; -NHCO-C1-C3 alkyl, -NHCO-C3-C4 cycloalkyl, -NHSO 2-phenyl; -CONH(C3-C4 cycloalkyl), -CON(C1-C3 alkyl)(C3-C 4 cycloalkyl), -C(=NOC1-C3 alkyl)-C1-C3 alkyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl groups include halogen, -CN, C1-C3 alkyl, C1-C3 haloalkyl and C1-C 3 haloalkoxy] independently selected from Group A consisting of: The remaining 1 to 2 optional substituents are Halogen, -CN, -NO2, C1-C6 alkyl, C3-C6 cycloalkyl, C1- C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxy C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C 3 haloalkylthio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkyls sulfonyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl and 5-6 membered heteroaryl The alkyl group is selected from the group consisting of halogen, -CN, C1-C3 alkyl, and C1-C3 haloalkyl. and optionally substituted with 1 to 2 substituents selected from each independently selected from Group B consisting of: Or, R 2are thiophene, furan, pyrazole, thiazole, isothiazole, oxazoline or isoxazole, where these are respectively Halogen, hydroxy, -CN, -NO2, C1-C6 alkyl, C3-C4 cycloalkenyl alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C 1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl C3-C4 cycloalkylsulfanyl, C3-C4 cycloalkylsulfinyl, C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloa alkylsulfinyl, C1-C3 haloalkylsulfonyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from the group consisting of halogen, -CN, C1-C3 alkyl, and C1-C3 haloalkyl. and optionally substituted with 1 to 2 substituents selected from and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is C1-C6 alkyl, wherein the alkyl is C1-C3 alkoxy-, C1-C3 haloalkoxy-, C1-C3 alkylthio, C1 -C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkyl Thio, C1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl; and , Phenyl [wherein the phenyl is selected from the group consisting of halogen, —CN, C1-C6 alkyl, C1-C3 1 to 4, each independently selected from the group consisting of haloalkyl and C1-C4 alkoxy; 2, which may be substituted with the substituent and is substituted with one substituent selected from the group consisting of: Or, R 2 is naphthyl, wherein the naphthyl is Halogen, hydroxy, -CN, -NO2, C1-C6 alkyl, C3-C4 cycloalkenyl alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C 1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl C3-C4 cycloalkylsulfanyl, C3-C4 cycloalkylsulfinyl, C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloa alkylsulfinyl, C1-C3 haloalkylsulfonyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from the group consisting of halogen, -CN, C1-C3 alkyl, and C1-C3 haloalkyl. and optionally substituted with 1 to 2 substituents selected from and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is a 9- or 10-membered heteroaryl, wherein the heteroaryl is Halogen, hydroxy, -CN, -NO2, C1-C6 alkyl, C3-C4 cycloalkenyl alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, C 1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl C3-C4 cycloalkylsulfanyl, C3-C4 cycloalkylsulfinyl, C3-C4 cycloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloa alkylsulfinyl, C1-C3 haloalkylsulfonyl; and Phenyl and 5-6 membered heteroaryl [wherein the phenyl or 5-6 membered heteroaryl The alkyl group is selected from the group consisting of halogen, -CN, C1-C3 alkyl, and C1-C3 haloalkyl. and optionally substituted with 1 to 2 substituents selected from and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: R 3a , R 3b are independently hydrogen; C1-C6 alkyl [wherein the alkyl is C 1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1-C4 alkyl Alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyls sulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C1-C3 Independently from the group consisting of haloalkylsulfinyl and C1-C3 haloalkylsulfonyl optionally substituted with 1 to 3 substituents selected from the group consisting of C3-C6 cycloalkyl; C 1-C6 haloalkyl;C2-C6 alkenyl;C2-C6 haloalkenyl;C2-C6 Alkynyl; C2-C6 haloalkynyl; benzyl wherein the phenyl substituent is a halo Gen, -CN, -NO2, C1-C6 alkyl, C1-C3 haloalkyl, C1-C4 alkyl 1 to 3 substituents independently selected from the group consisting of alkoxy and C1-C4 haloalkoxy or heterocyclyl-C1-C6 alkyl [wherein the Heterocyclyl substituents include 4- to 10-membered heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl. and aryl, each of which is selected from the group consisting of halogen, -CN, , -NO2, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: phenyl, wherein the phenyl is selected from halogen, -CN, -NO2, C1-C6 alkyl, C1 -substituted with one substituent selected from the group consisting of C3 haloalkyl and C1-C4 alkoxy; and optionally substituted; Or, R 3a , R 3b together with the carbon to which they are attached form a cyclopropane ring, a cyclobutane ring, and forming a tetrahydropyran ring, an oxetane ring, or a tetrahydropyran ring, wherein the ring is not substituted with a halogen, -CN, C1-C6 alkyl, C1-C3 haloalkyl and C1-C4 alkoxy each of which may be substituted with 1 to 2 substituents independently selected from the group consisting of: R 4 is pyridine, pyrimidine, pyrazine, pyridazine or thiazole, (A) The pyridine, pyrimidine, pyrazine or pyridazine is not a halogen, —CN, —N H2, -NO2, -COOH, -CONH2, -CSNH2, -CO2-C1-C3 Al alkyl, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, C1 -C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkyl alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylthio, C 1-C3 haloalkylsulfinyl, C1-C3 haloalkylsulfonyl, -NHCO- C1-C3 alkyl, -NHCO-C1-C3 haloalkyl, -NHCO-C1-C3 silyl an alkyl, -NHCO-C3-C4 cycloalkyl, wherein the cycloalkyl is selected from the group consisting of fluorine, chlorine, -CN, C1-C6 alkyl, and C1-C4 alkoxy; -NHCO-phenyl [wherein the Phenyl is substituted with halogen, -CN, C1-C3 alkyl, C1-C3 haloalkyl, C1- 1 to 2 substituents selected from the group consisting of C3 alkoxy and C1-C3 haloalkoxy -NHSO2-C1-C3 alkyl, -NHSO2-C1- C3 haloalkyl, -CONH(C1-C3 alkyl), -CON(C1-C3 alkyl )2, -CONH-SO2-C1-C3 alkyl, -CON(C1-C3 alkyl)(C 3-C6 cycloalkyl), -CONH(C1-C3 haloalkyl), -CONH(C3 -C6 cycloalkyl), -CONH(1-cyano-C3-C6 cycloalkyl), -C ONH-phenyl, wherein the phenyl is selected from the group consisting of halogen, —CN, C1-C3 alkyl, C The group consisting of 1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy and optionally substituted with 1 to 2 substituents selected from the group consisting of 3 substituents; and (B) The thiazole is selected from the group consisting of halogen, —CN, —NO2, C1-C6 alkyl, C3-C6 Cycloalkyl, C1-C3 haloalkyl, C1-C4 alkoxy, C1-C3 haloal Coxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkyl C1-C3 haloalkylsulfonyl, C1-C3 haloalkylthio, C1-C3 haloalkylsulfinyl and C1-C3 haloalkylsulfonyl It's okay to have it; R 5 is hydrogen, halogen, -CN, C1-C3 alkyl, C1-C3 haloalkyl, C 3-C4 cycloalkyl or C1-C3 alkoxy] It is a compound represented by the formula:
[0015] Particularly preferred is (Configuration 4-1), formula (I) [wherein, X is O or S; Q 1 and Q 2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or CH; R 1 is hydrogen; C1-C3 alkyl [wherein the alkyl is -CN, -Si(CH3 )3 or selected from the group consisting of fluorine, chlorine or bromine. optionally substituted with 1 to 3 substituents selected from the group consisting of C2-C4 alkenyl; C2-C4 alkynyl; quinyl; C3-C4 cycloalkyl-C1-C2 alkyl- [wherein the C3-C4 cyclo The alkyl is substituted with 1 to 2 substituents selected from the group consisting of fluorine, chlorine and bromine. may be]; R 2 is phenyl or pyridine, wherein the phenyl or pyridine is one of 1 to 3 substituted with substituents, provided that at least one substituent is not bonded to the carbon atom bonded to the C=X group; and the substituent is fluorine, chlorine, Bromine, -CN, -NO2, methyl, cyclopropyl, difluoromethyl, trifluoromethyl Thiol, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, methylsulfonyl phenyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, isopropylthio, isopropylsulfinyl, isopropylsulfonyl, cyclopropyl Thio, cyclopropylsulfinyl, cyclopropylsulfonyl, difluoromethylthio , difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio O, trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethyl. and methyl, are each independently selected; Or, R 2 is phenyl or pyridine, wherein the phenyl or pyridine is 1 in total substituted with up to 3 substituents, provided that the substituents are not adjacent to the carbon bonded to the C=X group; and the substituents of 1 are not present on any of the carbon atoms adjacent to the cyclopropyl, methyl, O, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethyl sulfonyl, isopropylthio, isopropylsulfinyl, isopropylsulfonyl, tert-butylthio, tert-butylsulfinyl, tert-butylsulfonyl, Cyclopropylthio, cyclopropylsulfinyl, cyclopropylsulfonyl, difluoro Fluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylsulfinyl phenylsulfonyl, trifluoromethylsulfonyl; phenylsulfonyl, wherein the phenyl is fluorine; Selected from the group consisting of chlorine, bromine, -CN, difluoromethyl and trifluoromethyl -NHCO-phenyl [wherein the phenyl is optionally substituted by 1 to 2 substituents as defined above]; Phenyl is selected from the group consisting of fluorine, chlorine, CN, methyl and trifluoromethyl. (cyclopropylamino)carbonyl, 1 -(methoxyimino)ethyl; phenyl and 5-membered heteroaryl, wherein said phenyl or 5-membered heteroaryl is fluorine, chlorine, bromine, -CN, difluoromethyl, trifluoromethyl substituted with 1 to 2 substituents selected from the group consisting of methyl and trifluoromethoxy; independently selected from Group A consisting of: The remaining 1-2 optional substituents are fluorine, chlorine, bromine, -CN, -NO2, methyl, cyclohexane, Propyl, difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy , difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoro difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio Oromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl and Phenyl, wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoromethyl and and optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, methyltrifluoro ... each independently selected from Group B consisting of: Or, R 2 is thiophene, furan, pyrazole, thiazole, oxazole or isoxazole azoles, where these are fluorine, chlorine, bromine, -CN, -NO2, Methyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxy, trifluoro difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfinyl sulfonyl and phenyl, wherein the phenyl is selected from fluorine, chlorine, bromine, -CN, difluorine, substituted with 1 to 2 substituents selected from the group consisting of methyl and trifluoromethyl; may be substituted with 1 to 3 substituents independently selected from the group consisting of ; Or, R 2 is C1-C3 alkyl, wherein the alkyl is methoxy, trifluoro Methoxy, difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, Difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, Trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl phenyl and phenyl, wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoromethyl; substituted with 1 to 2 substituents selected from the group consisting of methyl and trifluoromethyl; and optionally substituted with one substituent selected from the group consisting of: R 3a , R 3b are independently hydrogen; C1-C3 alkyl, wherein the alkyl is methyl; ethyl, ethyl, isopropyl, n-propyl, cyclopropyl, cyclobutyl, difluoro Fluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethyl Oromethoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl The group consisting of ruthio, trifluoromethylsulfinyl and trifluoromethylsulfonyl and optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyclopropyl, dipropyl, and cyclopropyl. Fluoromethyl, trifluoromethyl, difluoromethyl, trifluoromethyl, 2,2 -difluoroethyl, 2,2,2-trifluoroethyl, ethynyl, 2-propene-1- benzyl, wherein the phenyl substituents are fluorine, chlorine, methyl ... independently selected from the group consisting of fluorine, bromine, -CN, NO2, methyl, trifluoromethyl and methoxy optionally substituted with 1 to 3 substituents selected from the group consisting of: heterocyclyl-methyl; Here, the heterocyclyl substituent is a 4- to 10-membered heterocyclyl, a 5-membered heteroaryl and 6-membered heteroaryl, each of which is selected from the group consisting of fluorine the group consisting of chlorine, bromine, -CN, -NO2, methyl, trifluoromethyl and methoxy and phenyl [which may be substituted with 1 to 3 substituents independently selected from the group consisting of wherein the phenyl is fluorine, chlorine, bromine, -CN, -NO2, methyl, trifluoromethyl and optionally substituted with one substituent selected from the group consisting of methyl and methoxy. selected from the group consisting of: Or, R 3a , R 3b together with the carbon to which they are attached form a cyclopropane ring, a cyclobutane ring, forming a ethane ring, an oxetane ring, or a tetrahydropyran ring; R 4 is pyridine, pyrimidine or thiazole, wherein (A) the pyridine or Pyrimidines are fluorine, chlorine, bromine, -CN, -NO2, methyl, ethyl, difluoromethyl ethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, methoxy, difluoro Oromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl difluoromethylsulfinyl, difluoromethylthio, difluoromethylsulfonyl, difluoromethylsulfonyl trifluoromethylsulfinyl and trifluoromethylthio and (B) The thiazole is selected from the group consisting of fluorine, chlorine, bromine, -CN, -NO2, methyl, ethyl, diphenyl Fluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, methoxy , difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methyl sulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethyl sulfonyl, trifluoromethylthio, trifluoromethylsulfinyl and trifluoro and optionally substituted with 1 to 2 substituents selected from the group consisting of methylsulfonyl, ... ; R 5 is hydrogen, fluorine, chlorine, bromine, -CN, methyl, ethyl, isopropyl, diphenyl fluoromethyl, trifluoromethyl, cyclopropyl, methoxy or ethoxy. It is a compound represented by the formula:
[0016] Likewise particularly preferred are (Configuration 4-2), formula (I) [wherein, X is O or S; Q 1 and Q 2 is independently 5 or N, where Q 1 and Q 2 At least one of Also 1 is N; Y is a direct bond or CH; R 1 is hydrogen; C1-C3 alkyl [wherein the alkyl is -CN, -Si(CH3 )3 or selected from the group consisting of fluorine, chlorine or bromine. optionally substituted with 1 to 3 substituents selected from the group consisting of C2-C4 alkenyl; C2-C4 alkynyl; quinyl; C3-C4 cycloalkyl-C1-C2 alkyl- [wherein the C3-C4 cyclo The alkyl is substituted with 1 to 2 substituents selected from the group consisting of fluorine, chlorine and bromine. may be]; R 2is phenyl or pyridine, wherein the phenyl or pyridine is one of 1 to 3 substituted with substituents, provided that at least one substituent is not bonded to the carbon atom bonded to the C=X group; and the substituent is present on any carbon adjacent to Fluorine, chlorine, bromine, -CN, -NO2, methyl, cyclopropyl, difluoromethyl, Trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio O, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethyl sulfonyl, isopropylthio, isopropylsulfinyl, isopropylsulfonyl, Cyclopropylthio, cyclopropylsulfinyl, cyclopropylsulfonyl, difluoro difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethyl trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, and, Phenyl, wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoromethyl, and and optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, methyltrifluoro ... each independently selected from the group consisting of: Or, R 2 is phenyl or pyridine, wherein the phenyl or pyridine is 1 in total substituted with up to 3 substituents, provided that the substituents are not adjacent to the carbon bonded to the C=X group; and one substituent is not present on any carbon atom that is tert-Butyl, cyclopropyl, 1-cyanocyclopropyl, methylthio, methyls sulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, Isopropylthio, isopropylsulfinyl, isopropylsulfonyl, tert-butyl butylthio, tert-butylsulfinyl, tert-butylsulfonyl, cyclopropyl Ruthio, cyclopropylsulfinyl, cyclopropylsulfonyl, difluoromethylsulfonyl sulfinyl, difluoromethylsulfonyl, trifluoromethylsulfinyl, trifluoro trifluoromethylsulfonyl, trifluoroethylsulfinyl, trifluoroethylsulfonyl Le; Phenylsulfonyl [wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoro substituted with 1 to 2 substituents selected from the group consisting of methyl and trifluoromethyl; may]; -NHCO-phenyl, wherein the phenyl is selected from fluorine, chlorine, CN, methyl and trifluor. and optionally substituted with 1 to 2 substituents selected from the group consisting of fluoromethyl; (cyclopropylamino)carbonyl, 1-(methoxyimino)ethyl, acetamide, (cyclopropylcarbonyl)amino, (phenylsulfonyl)amino; and Phenyl and 5-membered heteroaryl, wherein said phenyl or 5-membered heteroaryl is fluorine-containing. Chlorine, bromine, -CN, difluoromethyl, trifluoromethyl and trifluoromethan and optionally substituted with 1 to 2 substituents selected from the group consisting of aryl, aryloxy ... independently selected from Group A consisting of: The remaining 1 to 2 optional substituents are Fluorine, chlorine, bromine, -CN, -NO2, methyl, cyclopropyl, difluoromethyl, Trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio O, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethyl Sulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethyl methylsulfinyl, trifluoromethylsulfonyl; and Phenyl, wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoromethyl and and optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, methyltrifluoro ... each independently selected from Group B consisting of: Or, R 2 is thiophene, furan, pyrazole, thiazole, oxazole or isoxazole sol, where each of these is Fluorine, chlorine, bromine, -CN, -NO2, methyl, cyclopropyl, difluoromethyl, Trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio O, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethyl Sulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethyl methylsulfinyl, trifluoromethylsulfonyl; and Phenyl, wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoromethyl, and and optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, methyltrifluoro ... and optionally substituted with 1 to 3 substituents independently selected from the group consisting of: Or, R 2 is C1-C3 alkyl, wherein the alkyl is Methoxy, trifluoromethoxy, difluoromethoxy, methylthio, methylsulfini methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoro trifluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl; and Phenyl, wherein the phenyl is selected from fluorine, chlorine, bromine, —CN, difluoromethyl, and and optionally substituted with 1 to 2 substituents selected from the group consisting of methyl, methyltrifluoro ... and is substituted with one substituent selected from the group consisting of: Or, R 2 is naphthyl; or pyrazolo[1.5-a]pyridin-2-yl [wherein may be substituted by trifluoromethyl or chlorine; R 3a , R 3b are independently hydrogen; C1-C3 alkyl, wherein the alkyl is methyl; ethyl, ethyl, isopropyl, n-propyl, cyclopropyl, cyclobutyl, difluoro Fluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethyl Oromethoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl The group consisting of ruthio, trifluoromethylsulfinyl and trifluoromethylsulfonyl and optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyclopropyl, dipropyl, and cyclopropyl. Fluoromethyl, trifluoromethyl, difluoromethyl, trifluoromethyl, 2,2 -difluoroethyl, 2,2,2-trifluoroethyl, ethynyl, 2-propene-1- benzyl, wherein the phenyl substituents are fluorine, chlorine, methyl ... independently selected from the group consisting of fluorine, bromine, -CN, NO2, methyl, trifluoromethyl and methoxy optionally substituted with 1 to 3 substituents selected from the group consisting of: heterocyclyl-methyl; Here, the heterocyclyl substituent is a 4- to 10-membered heterocyclyl, a 5-membered heteroaryl and 6-membered heteroaryl, each of which is selected from the group consisting of fluorine the group consisting of chlorine, bromine, -CN, -NO2, methyl, trifluoromethyl and methoxy and phenyl [which may be substituted with 1 to 3 substituents independently selected from the group consisting of wherein the phenyl is fluorine, chlorine, bromine, -CN, -NO2, methyl, trifluoromethyl and optionally substituted with one substituent selected from the group consisting of methyl and methoxy. selected from the group consisting of: Or, R 3a , R 3b together with the carbon to which they are attached form a cyclopropane ring, a cyclobutane ring, forming a ethane ring, an oxetane ring, or a tetrahydropyran ring; R 4 is pyridine, pyrimidine, pyrazine or thiazole, wherein (A) the pyridine Lysine, pyrimidine or pyrazine may contain fluorine, chlorine, bromine, -CN, -NH2, -NO2 , -COOH, -CONH2, -CSNH2, -CO2Me, methyl, ethyl, difluoro chloromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, methoxy, difluoromethyl Fluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfinyl sulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfinyl sulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethyl Trimethylsulfonyl, -NHCO-methyl, -NHCO-trifluoromethyl, -NHCO- CH2CN, -NHCO-cyclopropyl, -NHCO-1-cyanocyclopropyl, - NHSO2-methyl, -NHSO2-trifluoromethyl, -NHCO-phenyl [where and the phenyl is fluorine, chlorine, bromine, -CN, methyl, difluoromethyl, trifluoromethyl, Selected from the group consisting of fluoromethyl, methoxy, difluoromethoxy and trifluoromethoxy -CONH-methyl, -CONH- SO2-methyl, -CON-(N-methyl)-N-cyclopropyl, -CONH-difluoro -O-ethyl, -CONH-trifluoroethyl, -CONH-cyclopropyl, -CON H-1-cyanocyclopropyl, -CONH-phenyl, wherein the phenyl is selected from the group consisting of fluorine , chlorine, bromine, -CN, methyl, difluoromethyl, trifluoromethyl, methoxy, di 1 to 2 substituents selected from the group consisting of fluoromethoxy and trifluoromethoxy and optionally substituted with 1 to 3 substituents selected from the group consisting of and, (B) The thiazole is selected from the group consisting of fluorine, chlorine, bromine, -CN, -NO2, methyl, ethyl, diphenyl Fluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, methoxy , difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methyl sulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethyl sulfonyl, trifluoromethylthio, trifluoromethylsulfinyl and trifluoro and optionally substituted with 1 to 2 substituents selected from the group consisting of methylsulfonyl, ... ; R 5 is hydrogen, fluorine, chlorine, bromine, -CN, methyl, ethyl, isopropyl, diphenyl fluoromethyl, trifluoromethyl, cyclopropyl, methoxy or ethoxy. It is a compound represented by the formula:
[0017] Very particularly preferred are (Configuration 5-1), formula (I) [wherein, X is O; Q 1 is N; Q 2 is CR 5 and; Y is a direct bond; R 1 is hydrogen, cyclopropyl-CH2-, 3,3,3-trifluoropropyl, ethyl 2,2-difluoroethyl; R 2 is 3-chloro-2-fluoro-5-(trifluoromethyl)phenyl, 3-chloro 5-(methylsulfonyl)phenyl, 5-(methylsulfonyl)pyridin-3-yl , 3-(methylsulfonyl)phenyl, 3-(trifluoromethylsulfonyl)phenyl , 5-[(trifluoromethyl)sulfonyl]pyridin-3-yl, 3-chloro-5-[ (cyclopropylamino)carbonyl]phenyl, 3-cyclopropyl-5-(triflate (chloromethyl)phenyl, 2,3,5-trichlorophenyl, 3-phenyl-5-(trifluoromethyl)phenyl (3-chloro-5-(trifluoromethyl)phenyl)phenyl, [3-chloro-5-(trifluoromethyl)phenyl]methyl , 3-(4-fluorophenyl)-5-(trifluoromethyl)phenyl, 2-chlorophenyl phenyl, 2,5-dichlorophenyl, 2,3,4-trichlorophenyl, 2,3-dichlorophenyl 2,4-dichlorophenyl, 2,6-difluorophenyl, 3-chloro-5 -(trifluoromethylsulfonyl)phenyl, 5-chloro-3-thienyl, 3,4,5 -Trichloro-2-thienyl, 2,5-dichloro-3-thienyl, 4,5-dichloro-2 -thienyl, 1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl, 4-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl, 5-Methyl-1,2-oxazol-3-yl, 5-cyclopropyl-1,2-oxazo 3-chloro-1,2-oxazol-5-yl, 2-chloro-1,3- Thiazol-5-yl, 1-methyl-1H-pyrazol-4-yl, 5-chloro-1-methyl ethyl-1H-pyrazol-4-yl, 3-chloro-5-cyclopropylsulfonylphenyl 3-chloro-5-(4-fluorophenyl)sulfonylphenyl, 3-chloro-5- Ethylsulfonylphenyl, 3-cyclopropyl-5-fluorophenyl, 3-chloro- 5-(isopropylthio)phenyl, 3-chloro-5-(1H-pyrazol-1-yl) phenyl, 3-chloro-5-(1H-1,2,4-triazol-1-yl)phenyl, 3-chloro-5-cyclopropylphenyl, 3-chloro-5-isopropylsulfonyl Phenyl, 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazoline phenyl-5-yl, 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 4-(trifluoromethoxy)phenyl (trifluoromethylsulfonyl)phenyl, 3-chloro-5-[1-(methoxyimino) ethyl]phenyl, 3-(tert-butylthio)-5-chlorophenyl, 1-(4-fluorophenyl) (4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl -(trifluoromethoxy)phenyl]pyridin-3-yl, 3-chloro-5-methyls sulfonylphenyl, 3-chloro-5-methylsulfinylphenyl or 3-benzami 5-chlorophenyl; R 3a is hydrogen, methyl or methoxymethyl; R 3b is R 3a is hydrogen, then it is methyl or methoxymethyl; R 3b is R 3a is hydrogen when is methyl or methoxymethyl; R 42-pyridinyl, 2-pyrimidin-2-yl, 2-pyrimidin-4-yl, 5 -chloropyridin-2-yl, 4-chloropyridin-2-yl, 5-cyanopyridin-2 -yl, 4-cyano-2-pyridinyl, 5-(trifluoromethyl)-pyridin-2-yl 5-(difluoromethoxy)pyridin-2-yl, 5-(trifluoromethylthio) Pyridin-2-yl, 3,5-difluoro-2-pyridinyl, 5-chloro-3-fluoro -2-pyridinyl, 5-fluoropyrimidin-2-yl, 5-chloropyrimidin-2-yl 2-pyrazin-2-yl or 1,3-thiazol-2-yl; R 5 is hydrogen or methyl. It is a compound represented by the formula:
[0018] Likewise very particularly preferred are (Configuration 5-2), formula (I) [wherein, X is O or S; Q 1 is N; Q 2 is CR 5 and; Y is a direct bond or CH; R 1 is hydrogen, methyl, ethyl, 2-(trimethylsilyl)ethyl, 2,2-difluoro trifluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl or chloroethyl chloropropyl-CH2-; R 2 is 3-chloro-2-fluoro-5-(trifluoromethyl)phenyl, 3-chloro 3-methylsulfonyl-5-(trifluoromethyl)phenyl 5-(methylsulfonyl)pyridin-3-yl, 3-(methylsulfonyl)phenyl phenyl, 3-(trifluoromethylsulfonyl)phenyl, 5-[(trifluoro methyl)sulfonyl]pyridin-3-yl, 3-chloro-5-[(cyclopropylamino )carbonyl]phenyl, 3-cyclopropyl-5-(trifluoromethyl)phenyl, 2,3,5-trichlorophenyl, 3-phenyl-5-(trifluoromethyl)phenyl , [3-chloro-5-(trifluoromethyl)phenyl]methyl, 3-(4-fluorophenyl) (phenyl)-5-(trifluoromethyl)phenyl, 2-chlorophenyl, 2,5-dichloro 2,3,4-trichlorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl Chlorophenyl, 2,6-difluorophenyl, 3-fluoro-5-(trifluoromethyl) 3-chloro-5-(trifluoromethylsulfonyl)phenyl, 3-chloro-5-(trifluoromethylsulfonyl)phenyl , 5-chloro-3-thienyl, 3,4,5-trichloro-2-thienyl, 2,5-dichloro 4,5-dichloro-2-thienyl, 1-methyl-5-(trifluoro methyl)-1H-pyrazol-3-yl, 4-chloro-1-methyl-3-(trifluoro methyl)-1H-pyrazol-5-yl, 5-methyl-1,2-oxazol-3-yl , 5-cyclopropyl-1,2-oxazol-3-yl, 3-chloro-1,2-oxazol-3-yl 2-chloro-1,3-thiazol-5-yl, 1-methyl-1H-pyridyl pyrazol-4-yl, 5-chloro-1-methyl-1H-pyrazol-4-yl, 3-chloro 3-chloro-5-(4-fluorophenyl) ) sulfonylphenyl, 3-chloro-5-ethylsulfonylphenyl, 3-cyclopropyl 3-chloro-5-(isopropylthio)phenyl, 3-chloro-5-fluorophenyl, 3-chloro-5-(1H-pyrazol-1-yl)phenyl, 3-chloro-5-(1H-pyrazol-1-yl)phenyl 4-triazol-1-yl)phenyl, 3-tert-butyl-5-chlorophenyl, 3-tert-butyl-5-bromophenyl, 3-fluoro-5-cyclopropylphenyl 3-chloro-5-cyclopropylphenyl, 3-chloro-5-isopropylsulfonyl phenyl, 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyra 3-cyclopropyl-5-(trifluoromethoxy)phenyl, 4- (trifluoromethylsulfonyl)phenyl, 3-chloro-5-[1-(methoxyimino )ethyl]phenyl, 3-(tert-butylthio)-5-chlorophenyl, 1-(4- 1-(4-fluorophenyl)-5-pyrazol-4-yl -(trifluoromethyl)-1H-pyrazol-3-yl, 5-[4-(trifluoromethyl)- (trioxy)phenyl]pyridin-3-yl, 3-chloro-5-methylsulfanylphenyl , 3-chloro-5-methylsulfinylphenyl, 3-benzamido-5-chlorophenyl 3-(tert-butylsulfonyl)-5-chlorophenyl, 5-[4-(trifluoromethyl)- (4-(trifluoromethyl)phenyl]-pyridin-3-yl, 5-[4-(trifluoromethoxy)phenyl]-pyridin-3-yl phenyl]-pyridin-3-yl, 5-(4-chlorophenyl)pyridin-3-yl, 5- (4-fluorophenyl)pyridin-3-yl, 3-chloro-5-[(phenylsulfonyl phenyl)amino]phenyl, 3-acetamido-5-chlorophenyl, 3-chloro-5-[( cyclopropylcarbonyl)amino]phenyl, 3-chloro-5-[(2,2,2-tri fluoroethyl)sulfinyl]phenyl, 3-chloro-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl (trifluoromethyl)sulfonyl]phenyl, 3-chloro-5-[3-(trifluoromethyl)- 1H-pyrazol-1-yl]phenyl, 3,5-bis(methylsulfonyl)phenyl, Pyrazolo[1,5-a]pyridin-2-yl, 7-(trifluoromethyl)pyrazolo[1 ,5-a]pyridin-2-yl, 6-chloropyrazolo[1,5-a]pyridin-2-yl , naphth-2-yl, 3-[4'-(trifluoromethoxy)phenyl]-phenyl, 3 -(4'-fluorophenyl)-5-(trifluoromethyl)phenyl or 3-chloro- 5-(1-cyanocyclopropyl)phenyl; R 3a is hydrogen, methyl or methoxymethyl; R 3b is R 3a is hydrogen, then it is methyl or methoxymethyl; R 3b is R 3a is hydrogen when is methyl or methoxymethyl; R 3a and R 3b form a cyclopropane ring together with the carbon to which they are attached; R 4 pyridin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, 5-fluoro 5-chloropyrimidin-2-yl, 5-cyanopyrimidine -2-yl, 5-(trifluoromethyl)pyrimidin-2-yl, 5-methylpyrimidine -2-yl, 5-fluoropyridin-2-yl, 5-chloropyridin-2-yl, 2-chloropyridin-2-yl 4-chloropyridin-4-yl, 5-cyanopyridin-2-yl, 4-cyano-pyridin-2-yl yl, 6-cyano-pyridin-2-yl, 5-methoxy-pyridin-2-yl, 5-(trimethylsilyl) (trifluoromethyl)-pyridin-2-yl, 5-(difluoromethoxy)pyridin-2-yl yl, 5-(trifluoromethylthio)pyridin-2-yl, 5-nitropyridin-2-yl yl, 5-aminopyridin-2-yl, 3,5-difluoropyridin-2-yl, 5-chloropyridin-2-yl 3-fluoropyridin-2-yl, pyridin-2-yl-5-carboxylic acid, pyridin Methyl N-pyridin-2-yl-5-carboxylate, Methyl N-pyridin-2-yl-5-carboxylate N-cyclopropyl-pyridin-2-yl-5-carboxamide, N-cyclopropyl-pyridin-2-yl-5-carboxamide propyl-N-methyl-pyridin-2-yl-5-carboxamide, N-(1-cyanocyclohexyl) N-(2,2-difluoropropyl)-pyridin-2-yl-5-carboxamide N-(2,2,2-trifluoroethyl)-pyridin-2-yl-5-carboxamide N-methylsulfonyl-pyridine- 2-yl-5-carboxamide, N-(4-fluorophenyl)-pyridin-2-yl- 5-Carboxamido, 5-acetamidopyridin-2-yl, 5-(trifluoroacetamido) Amido)-pyridin-2-yl, 5-(2-cyanoacetylamino)-pyridin-2-yl 5-[(cyclopropylcarbonyl)amino]pyridin-2-yl, 5-[(1-cyclopropylcarbonyl)amino]pyridin-2-yl 5-(methanesulfonic acid)-2-pyridin-2-yl)amino-5-(methylsulfonic acid)-2-pyridin-2-yl Amido)-pyridin-2-yl, 5-(trifluoromethylsulfonamido)-pyridine -2-yl, 5-[(4-fluorobenzoyl)amino]pyridin-2-yl pyrazine -2-yl, 2-cyano-pyrazin-5-yl or 1,3-thiazol-2-yl ; R 5 is hydrogen, methyl or trifluoromethyl. It is a compound represented by the formula:
[0019] In a further preferred embodiment, the present invention provides a compound of formula (I') [ka]
[0020] wherein the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 3a , R 3b , R 4 and R 5 is configuration (1-1) or configuration (2-1) or configuration (3-1) or has the meaning given in structure (4-1) or structure (5-1).
[0021] In yet another preferred embodiment, the present invention provides a compound of formula (I') [ka]
[0022] wherein the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 3a , R 3b , R 4 and R 5 is configuration (1-2) or configuration (2-2) or configuration (3-2) or has the meaning given in structure (4-2) or structure (5-2).
[0023] In a further preferred embodiment of the compound of formula (I'), Q 1 is N or CR 5 represents, and Q 2 represents N, as well as all further structural elements Y, R 1 , R 2 , R 3a , R 3b , R 4 and R 5 is configuration (1-1) or configuration (2-1) or configuration (3-1) Or it has the meaning described above in structure (4-1) or structure (5-1).
[0024] In yet another preferred embodiment of the compound of formula (I′), Q 1 is N or C R 5 represents, and Q 2 represents N, as well as all further structural elements Y, R 1 , R 2 , R 3a , R 3b , R 4 and R 5 is the structure (1-2) or the structure (2-2) or the structure (3- 2) or (4-2) or (5-2) have the meanings described above. .
[0025] In yet another preferred embodiment of the compound of formula (I′), Q 1 represents N , and Q 2 is CR 5 and all further structural elements Y, R 1 , R 2 , R 3 a , R 3b , R 4 and R 5 is structure (1-1) or structure (2-1) or structure (3-1) or has the meaning described above in the structure (4-1) or the structure (5-1).
[0026] In yet another preferred embodiment of the compound of formula (I′), Q 1 represents N , and Q 2 is CR 5and all further structural elements Y, R 1 , R 2 , R 3 a , R 3b , R 4 and R 5 is structure (1-2) or structure (2-2) or structure (3-2) or has the meaning described above in structure (4-2) or structure (5-2).
[0027] Among these, the following configurations are particularly preferred: [Table 1] TIFF0007812478000005.tif115133
[0028] In a further preferred embodiment, the present invention provides a compound of formula (I″) [ka]
[0029] wherein, in the formula, R 3b is C1-C3 alkyl (particularly preferred The most important ones are Me) and R 3a is H, where the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 4 and R 5 is configuration (1-1) or configuration (2-1) or configuration (3-1) or has the meaning given in structure (4-1) or structure (5-1).
[0030] In yet another preferred embodiment, the present invention provides a compound of formula (I″): [ka]
[0031] wherein, in the formula, R 3b is C1-C3 alkyl (particularly preferred The most important ones are Me) and R 3a is H, where the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 4 and R 5 is configuration (1-2) or configuration (2-2) or configuration (3-2) or has the meaning given in structure (4-2) or structure (5-2).
[0032] In a further preferred embodiment, the present invention provides a compound of formula (I''') [ka]
[0033] wherein, in the formula, R 3b is C1-C3 alkyl (particularly preferred The most important ones are Me) and R 3a is H, where the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 4 and R 5 is configuration (1-1) or configuration (2-1) or configuration (3-1) or has the meaning given in structure (4-1) or structure (5-1).
[0034] In yet another preferred embodiment, the present invention provides a compound of formula (I''') [ka]
[0035] wherein, in the formula, R 3b is C1-C3 alkyl (particularly preferred The most important ones are Me) and R 3a is H, where the structural elements Y, Q 1 , Q 2 , R 1 , R 2 , R 4 and R 5 is configuration (1-2) or configuration (2-2) or configuration (3-2) or has the meaning given in structure (4-2) or structure (5-2).
[0036] In a further preferred embodiment, the present invention provides a compound of formula (I'p1) [ka]
[0037] wherein Y is a direct bond and the structural element R 1 , R 2 , R 3a , R 3b , R 4 and R 5 have the meanings given in the table below. do: [Table 2] TIFF0007812478000012.tif63169
[0038] In yet another preferred embodiment, the present invention provides a compound of formula (I'p1) [ka]
[0039] wherein Y is a direct bond and the structural element R 1 , R 2 , R3a , R 3b , R 4 and R 5 have the meanings given in the table below. do: [Table 3]
[0040] TIFF0007812478000015.tif60167
[0041] According to a further aspect, the present invention provides a method for preparing a compound of general formula (I) above, Useful intermediate compounds are included.
[0042] In particular, the present invention relates to a compound of the general formula (a * ): [ka]
[0043] wherein the structural elements Y, R 1 , R 2 , R 3a and R 3b is the structure (1-1) or the structure (2-1) or the structure (3-1) or the structure (4-1 ) or has the meaning given in structure (5-1).
[0044] In particular, the present invention further provides compounds of the general formula (a * ): [ka]
[0045] wherein the structural elements Y, R 1 , R 2 , R 3a and R 3b is the structure (1-2) or the structure (2-2) or the structure (3-2) or the structure (4-2) ) or have the meaning given in structure (5-2).
[0046] In particular, the present invention provides a compound of the general formula (b * ): [ka]
[0047] The present invention also includes an intermediate compound represented by the formula: Wherein, in the above formula: E is hydrogen or C1-C6 alkyl; A is -CN, chlorine or fluorine; L is S, SO or SO2.
[0048] In particular, the present invention provides a compound of the general formula (c * ): [ka]
[0049] The present invention also includes an intermediate compound represented by the formula: Wherein, in the above formula: E is hydrogen or C1-C6 alkyl; A is bromine, chlorine, fluorine, —CN or trifluoromethyl, preferably chlorine. is.
[0050] In particular, the present invention provides a compound of the general formula (d * ): [ka]
[0051] The present invention also includes an intermediate compound represented by the formula: Wherein, in the above formula: E is hydrogen or C1-C6 alkyl; A is bromine, chlorine or fluorine, preferably chlorine; L is S, SO or SO2, preferably S or SO2, more preferably is SO2; J is ethyl, isopropyl, tert-butyl, cyclopropyl, 2,2,2-trimethylsilyl trifluoroethyl or 4-fluorophenyl; and where, the formula (d * The compound represented by the formula 3-(ethylsulfanyl)-5-fluoro 3-(tert-butylsulfanyl)-5-fluorobenzoic acid, not benzoic acid But not.
[0052] The present invention further provides the compound 3-cyclopropyl-5-(trifluoromethoxy)benzoic acid. acid and methyl 3-cyclopropyl-5-(trifluoromethoxy)benzoate.
[0053] The compound represented by formula (I) may exist in the form of stereoisomers depending on the type of substituents. i.e., geometric and / or optical isomeric forms or isomeric mixtures in various compositions. Although, generally, only for compounds of formula (I) Although discussed herein, the present invention does not include the pure stereoisomers and their derivatives. and any desired mixture of
[0054] However, according to the present invention, it is preferred to use an optically active compound of formula (I). Stereoisomers and their salts are used.
[0055] Thus, the present invention provides a method for controlling pests (which includes arthropods, and in particular insects). for the removal of enantiomers and diastereomers, both pure and their mixtures. do.
[0056] Where appropriate, the compounds of formula (I) may exist in different polymorphic forms or can exist as a mixture of different polymorphic forms. Both pure polymorphs and polymorphic mixtures are It is provided by and can be used in accordance with the present invention.
[0057] definition Those skilled in the art will understand that when the expressions "a" or "an" are used in this application, even if the Even if not explicitly stated, "one," "one or more," or "at least one" may be used depending on the context. " I know that it can mean ".
[0058] For all structures described herein, including ring systems and groups, adjacent atoms may be -O It must not be -O- or -OS-.
[0059] Structures with variable numbers of possible carbon atoms (C atoms) are intended to be more specific. In this application, C 炭素原子の下限 -C 炭素原子の上限 Structure (C LL -C UL For example, alkyl groups may be composed of 3 to 10 carbon atoms. In that case, C3-C 10 -alkyl. It consists of carbon atoms and heteroatoms. The resulting ring structure can be described as an "LL-UL membered" structure. An example of a six-membered ring structure is toluene. It is a methyl group-substituted six-membered ring structure.
[0060] Collective terms for substituents, e.g., C LL -C UL -alkyl may be a complex substituent, e.g. C LL -CUL -Cycloalkyl-C LL -C UL -If it is at the end of alkyl, The first component of the substituent, e.g., C LL -C UL -Cycloalkyl is the same as and independently, the latter substituents, e.g., C LL -C UL -Al The term "cyclic group" as used herein refers to chemical groups, ring systems, and cyclic radicals. All the collective words that are LL -C UL By adding "LL~UL member" It can be stated more specifically.
[0061] In the definitions of the symbols given in the formula above, a set of substituents generally representative of the following is provided: used the word.
[0062] Halogen is an element of the seventh main group, preferably fluorine, chlorine, bromine and iodine, more preferably Preferably it concerns fluorine, chlorine and bromine, even more preferably fluorine and chlorine.
[0063] Examples of heteroatoms are N, O, S, P, B, Si. Preferably, the term "heteroatom" is used. " relates to N, S and O.
[0064] According to the present invention, "alkyl", either alone or as part of a chemical group, preferably represents 1 Straight or branched chain hydrocarbons having up to 6 carbon atoms, such as methyl, ethyl, n- Propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl , 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl , 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 2 ,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-di Methylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethylbutyl and 2-ethylbutyl. Alkyl having 1 to 4 carbon atoms, e.g. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, sec-butyl or t-butyl are also preferred. Alkyl according to the present invention is defined as one or more The substituted groups may be the same or different radicals as above.
[0065] According to the present invention, "alkenyl", either alone or as part of a chemical group, preferably A straight or branched chain hydrocarbon having 2 to 6 carbon atoms and at least one double bond , for example, vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl , 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl -2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl , 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl 4-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4 -pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1 -dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3- Butenyl, 1,3-dimethyl-2-butenyl, 2,2-dimethyl-3-butenyl, 2,3 -dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl , 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl. Aryl having 2 to 4 carbon atoms. phenyl, for example, inter alia, 2-propenyl, 2-butenyl or 1-methyl-2-propenyl; Alkenyl according to the present invention is preferably one or more of the same or different It may be substituted with a radical such as
[0066] According to the present invention, "alkynyl", either alone or as part of a chemical group, preferably A straight or branched chain hydrocarbon having 2 to 6 carbon atoms and at least one triple bond , for example, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl , 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2- Methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl , 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5 -hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl -4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl 4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-3-butynyl , 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3 -butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and 2,5-hexadinyl. Alkynyl having 2 to 4 carbon atoms, for example, Also preferred are ethynyl, 2-propynyl, and 2-butynyl-2-propenyl. The alkynyl groups defined above may be substituted with one or more identical or different radicals. .
[0067] According to the present invention, "cycloalkyl" is preferred, either alone or as part of a chemical group. Monocyclic, bicyclic or tricyclic hydrocarbons having 3 to 10 carbon atoms, e.g., cyclohexane, Propyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclobutyl octyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl represents cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms, e.g. For example, cyclopropyl or cyclobutyl are particularly preferred. Alkyl can be substituted with one or more identical or different radicals.
[0068] According to the present invention, "alkylcycloalkyl" preferably has 4 to 10 or 4 to 7 alkyl groups. monocyclic, bicyclic or tricyclic alkylcycloalkyl having carbon atoms, for example, ethylcyclopropyl, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopropyl It represents cyclopentyl and 4-methylcyclohexyl. alkylcycloalkyl, such as, inter alia, ethylcyclopropyl or 4-methylcyclopropyl; Cyclohexyl and the like are also preferred. Alkylcycloalkyl according to the present invention is one or more identical or may be substituted with a different radical.
[0069] According to the present invention, "cycloalkylalkyl" preferably has 4 to 10 or 4 to 7 alkyl groups. monocyclic, bicyclic or tricyclic cycloalkylalkyl having carbon atoms, for example, Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl cyclopentylethyl and cyclopentylethyl. alkylalkyl, such as, inter alia, cyclopropylmethyl or cyclobutylmethyl; Cycloalkylalkyl according to the present invention is preferably one or more of the same or different The group may be substituted with any of the following radicals:
[0070] According to the present invention, "hydroxyalkyl" preferably has 1 to 6 carbon atoms. , straight or branched chain alcohols, such as methanol, ethanol, n-propanol, Isopropanol, n-butanol, isobutanol, s-butanol and t-butanol Hydroxyalkyl groups having 1 to 4 carbon atoms are also preferred. The hydroxyalkyl groups may be substituted with one or more identical or different radicals. do.
[0071] According to the present invention, "alkoxy" preferably refers to straight or is a branched O-alkyl, for example, methoxy, ethoxy, n-propoxy, isopropoxy It represents 1-4 carbon atoms, n-butoxy, isobutoxy, s-butoxy, and t-butoxy. Alkoxy groups containing one or more identical alkyl groups are also preferred. They may be substituted with the same or different radicals.
[0072] According to the present invention, "alkylthio" or "alkylsulfanyl" preferably means 1 to Straight or branched chain S-alkyl having 6 carbon atoms, for example, methylthio, ethyl Thio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio alkylthio and t-butylthio. Alkylthio groups having 1 to 4 carbon atoms are also preferred. Alkylthio groups according to the present invention may be substituted with one or more identical or different radicals. may be substituted with
[0073] According to the present invention, "alkylsulfinyl" preferably has 1 to 6 carbon atoms. straight-chain or branched alkylsulfinyl, for example, methylsulfinyl, ethylsulfinyl; sulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl isobutylsulfinyl, s-butylsulfinyl and t-butylsulfinyl Also preferred are alkylsulfinyl groups having 1 to 4 carbon atoms. The alkylsulfinyl group may be substituted with one or more identical or different radicals. and encompasses both enantiomers.
[0074] According to the present invention, "alkylsulfonyl" preferably has 1 to 6 carbon atoms. , straight or branched alkylsulfonyl, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutyl sulfonyl, s-butylsulfonyl and t-butylsulfonyl. Alkylsulfonyl groups having 1 alkyl groups are also preferred. The substituted groups may be the same or different.
[0075] According to the present invention, "cycloalkylthio" or "cycloalkylsulfanyl" is preferably -S-cycloalkyl, preferably having 3 to 6 carbon atoms, such as cyclopropyl Thio, cyclobutylthio, cyclopentylthio, cyclohexylthio. 3 to 5 Cycloalkylthio groups having carbon atoms are also preferred. Cycloalkylthio groups according to the present invention may be substituted with one or more identical or different radicals.
[0076] According to the present invention, "cycloalkylsulfinyl" preferably has 3 to 6 carbon atoms. -S(O)-cycloalkyl, for example, cyclopropylsulfinyl, cyclo represents butylsulfinyl, cyclopentylsulfinyl, and cyclohexylsulfinyl Cycloalkylsulfinyl groups having 3 to 5 carbon atoms are also preferred. A cycloalkylsulfinyl group may be substituted with one or more identical or different radicals. It can be exchanged and includes both enantiomers.
[0077] According to the present invention, "cycloalkylsulfonyl" preferably has 3 to 6 carbon atoms. -SO2-cycloalkyl, for example, cyclopropylsulfonyl, cyclobutyl Sulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl. 3 to 5 Cycloalkylsulfonyl groups having carbon atoms are also preferred. The sulfonyl groups may be substituted with one or more identical or different radicals.
[0078] According to the present invention, "phenylthio" or "phenylsulfanyl" means -S-phenyl phenylthio. The phenylthio groups according to the present invention may be one or more identical or or may be substituted with a different radical.
[0079] According to the present invention, "phenylsulfinyl" refers to -S(O)-phenyl, e.g., phenyl The phenylsulfinyl group according to the present invention may be one or more identical or different radicals and both enantiomers can be Contains.
[0080] According to the present invention, "phenylsulfonyl" refers to -SO2-phenyl, e.g., phenyl The phenylsulfonyl group according to the present invention may be one or more identical or different. It may be substituted with a radical which is
[0081] According to the present invention, "alkylcarbonyl" includes methylcarbonyl, ethylcarbonyl, n-Propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl and t-butylcarbonyl linear or branched alkyl groups, preferably having 2 to 7 carbon atoms, such as alkylcarbonyl; It represents alkyl-C(=O). Alkylcarbonyl having 1 to 4 carbon atoms is also preferred. Alkylcarbonyl according to the invention may be substituted with one or more identical or different radicals. can be exchanged.
[0082] According to the present invention, "alkoxycarbonyl" alone or as a component of a chemical group means an alkoxycarbonyl group. The alkoxy moiety preferably has 1 to 6 carbon atoms or 1 to 4 carbon atoms. linear or branched alkoxycarbonyl, for example, methoxycarbonyl, ethoxycarbonyl; carbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl The alkoxycarbonyl group according to the present invention represents one or more alkoxycarbonyl groups. The substituted groups may be the same or different radicals as above.
[0083] According to the present invention, "alkylaminocarbonyl" preferably has 1 to 6 alkyl groups in the alkyl moiety. a straight or branched chain alkylaminocarbonyl group having 1 to 4 carbon atoms; Nyl, for example, methylaminocarbonyl, ethylaminocarbonyl, n-propylamino carbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl The alkylaminocarbonyl group according to the present invention represents one or more identical aminocarbonyl groups. or may be substituted with a different radical.
[0084] According to the present invention, "N,N-dialkylaminocarbonyl" is preferred for the alkyl moiety. or straight or branched chain N,N-dicarboxylic acids having 1 to 6 carbon atoms or 1 to 4 carbon atoms Alkylaminocarbonyl, for example, N,N-dimethylaminocarbonyl, N,N-diaminocarbonyl N,N-di(n-propylamino)carbonyl, N,N-di(isopropylamino)carbonyl N,N-di-(s-butylamino)carbonyl and N,N-di-(s-propylamino)carbonyl The N,N-dialkylaminocarbonyl group according to the present invention may be one or more identical or different. It may be substituted with a radical which is
[0085] According to the present invention, "aryl" preferably refers to an alkyl group having 6 to 14, especially 6 to 10, ring carbon atoms. monocyclic, bicyclic or polycyclic aromatic systems having rings, for example phenyl, naphthyl, aryl, tolyl, phenanthrenyl, and preferably phenyl. Polycyclic systems in which the binding site is on the aromatic system, e.g., tetrahydronaphthyl, indenyl, indenyl Aryl groups according to the present invention also represent one or more aryl groups. The substitution may be with the same or different radicals.
[0086] An example of a substituted aryl is arylalkyl, which is a C1-C4-alkyl group. C6-C 14 - one or more identical or different in the aryl moiety Examples of such arylalkyls include benzophenone, ... Examples include diphenyl and phenyl-1-ethyl.
[0087] According to the present invention, a "heterocycle", a "heterocyclic ring" or a "heterocyclic ring system" is at least At least one carbon atom is a heteroatom (preferably N, O, S, P, B, Si, Se) and is substituted with a heteroatom selected from the group consisting of saturated, unsaturated or heteroaromatic at least one ring of the aryl group, wherein the ring is unsubstituted or substituted; The bond site is on a ring atom. Unless otherwise specified, the heterocyclic ring preferably contains 3 to 9 heterocyclic rings. Ring atoms (particularly, 3 to 6 ring atoms) and one or more (preferably, 1 to 4, particularly, 1, 2 one or three) heteroatoms (preferably heteroatoms selected from the group consisting of N, O and S) atom), but the two oxygen atoms must not be directly adjacent. Usually, it contains up to four nitrogen atoms and / or up to two oxygen atoms and / or up to two sulfur atoms. When the heterocyclyl radical or the heterocyclic ring is optionally substituted, The heterocyclyl radical or heterocyclic ring may be fused to another carbocyclic or heterocyclic ring. In the case of optionally substituted heterocyclyl, the invention also includes polycyclic systems, e.g. 8-Azabicyclo[3.2.1]octanyl or 1-azabicyclo[2.2.1]heptyl In the case of an optionally substituted heterocyclyl, the present invention also includes spirocyclic rings. Also included are systems such as 1-oxa-5-azaspiro[2.3]hexyl.
[0088] Heterocyclyl groups according to the invention include, for example, piperidinyl, piperazinyl, morpholinyl, methyl ... Linyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazo Lysinyl, dioxolanyl, dioxolyl, pyrazolidinyl, tetrahydrofuranyl, di Hydrofuranyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl, oxazetanyl oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyridine dioxopyrrolidinyl, oxomorpholinyl, oxopiperazinyl and oxo Cepanil, etc.
[0089] Of particular interest are heteroaryl, i.e., heteroaromatic systems. The term "heteroaryl" refers to heteroaromatic compounds, i.e., heterocycles, which are encompassed by the above definition of heterocycle. It represents a fully unsaturated aromatic heterocyclic compound. Preferred is one selected from the above group. having up to three (preferably one or two) identical or different heteroatoms; Heteroaryl according to the present invention is, for example, furyl, thienyl, phenyl ... Triazolyl, imidazolyl, 1,2,3-triazolyl and 1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,3 ,4-oxadiazolyl, 1,2,4-oxadiazolyl and 1,2,5-oxadiazolyl Aryl, azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1 ,3,5-triazinyl, 1,2,4-triazinyl and 1,2,3-triazinyl, 1 ,2,4-oxazinyl, 1,3,2-oxazinyl, 1,3,6-oxazinyl and 1 ,2,6-oxazinyl, oxepinyl, thiepinyl, 1,2,4-triazolonyl, and and 1,2,4-diazepinyl. Heteroaryl groups according to the present invention are those containing one or more of the same The substituents may be the same or different radicals.
[0090] The term "optionally substituted" refers to a group / substituent, e.g., alkyl, Alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and hetero This means that the aryl radicals and the like are substituted, for example, means a substituted radical derived from a base structure that is not one substituent or a plurality of substituents, preferably 1, 2, 3, 4, 5, 6 or 7 substituents ) is, for example, amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, Buto, isothiocyanato, C1-C4-carboxyl, carbonamido, SF5, amino Sulfonyl, C1-C4-alkyl, C1-C4-haloalkyl, C3-C4-cycloalkyl C2-C4-alkenyl, C5-C6-cycloalkenyl, C2-C4-alkyl Nyl, N-mono-C1-C4-alkylamino, N,N-di-C1-C4-alkylamino N-C1-C4-alkanoylamino, C1-C4-alkoxy, C1-C4-halo Alkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C3-C 4-Cycloalkoxy, C5-C6-cycloalkenyloxy, C1-C4-alkoxy Carbonyl, C2-C4-alkenyloxycarbonyl, C2-C4-alkynyloxy Carbonyl, C6-aryloxycarbonyl, C 10 -aryloxycarbonyl, C 14 -aryloxycarbonyl, C1-C4-alkanoyl, C2-C4-alkenyl Carbonyl, C2-C4-alkynylcarbonyl, C6-arylcarbonyl, C 10 - Arylcarbonyl, C 14 -arylcarbonyl, C1-C4-alkylthio, C1- C4-haloalkylthio, C3-C4-cycloalkylthio, C2-C4-alkenylthio O, C5-C6-cycloalkenylthio, C2-C4-alkynylthio, C1-C4-a alkylsulfinyl (wherein both enantiomers of the C1-C4-alkylsulfinyl group C1-C4-haloalkylsulfinyl (wherein C1-C4-haloalkylsulfinyl is included), both enantiomers of the alkylsulfinyl group are included), C1-C4-alkyl C1-C4-haloalkylsulfonyl, N-mono-C1-C4-alkyl Aminosulfonyl, N,N-di-C1-C4-alkylaminosulfonyl, C1-C4- alkylphosphinyl, C1-C4-alkylphosphonyl (wherein C1-C4-alkyl Both the C1-C4-alkylphosphonyl and C1-C4-alkylphosphonyl enantiomers are included. N-C1-C4-alkylaminocarbonyl, N,N-di-C1-C4-alkyl Aminocarbonyl, N-C1-C4-alkanoylaminocarbonyl, N-C1-C4- Alkanoyl-N-C1-C4-alkylaminocarbonyl, C6-aryl, C 10 - Aryl, C 14 -aryl, C6-aryloxy, C 10 -aryloxy, C 14 -aryloxy, benzyl, benzyloxy, benzylthio, C6-arylthio, C 10 -arylthio, C 14 -arylthio, C6-arylamino, C 10 -aryl Amino, C 14 -arylamino, benzylamino, heterocyclyl and trialkylamino alkyl, substituents attached through a double bond (e.g., C1-C4-alkylidene (e.g., methylidene or ethylidene), oxo group, imino group and substituted imino group). When two or more radicals form one or more rings, they are selected from the group consisting of: , carbocyclic, heterocyclic, saturated, partially saturated, unsaturated (including, for example, aromatic rings) and may be further substituted. Substituents ("first substituent level"), if they contain hydrocarbonaceous moieties, wherein further substituents ("second substituent level"), such as halogen, hydroxyl, Amino, nitro, cyano, isocyano, azido, acylamino, oxo and imino groups The term "substituted" refers to a group consisting of aryl, aryls ... The "(optionally)" group preferably includes only one or two substitution levels. Includes.
[0091] Halogen-substituted or halogenated chemical groups (e.g., alkyl or alkoxy) is substituted with one halogen or up to the maximum possible number of substituents. Such groups are also called halo groups (e.g., haloalkyl). In the case of poly-halogen substitution, the halogen atoms may be the same or different. They may all be bonded to one carbon atom or may be bonded to multiple carbon atoms. Halogen is in particular fluorine, chlorine, bromine or iodine, and is preferably Preferably, it is fluorine, chlorine or bromine, more preferably fluorine. The halogen-substituted group is monohalocycloalkyl, e.g., 1-fluorocycloalkyl. 2-fluorocyclopropyl or 1-fluorocyclobutyl, monohaloal Chlorethyl, e.g., 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroethyl chloroethyl, chloromethyl or fluoromethyl, perhaloalkyl, for example trichloromethyl methyl or trifluoromethyl or CF2CF3, polyhaloalkyl, e.g., difluoro Methyl, 2-fluoro-2-chloroethyl, dichloromethyl, 1,1,2,2-tetrafluoroethane Further examples of haloalkyl include fluoroethyl and 2,2,2-trifluoroethyl. , trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl , bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl , 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2, 2-difluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl and Pentafluoro-t-butyl is preferred. Preferred are those having 1 to 4 carbon atoms and fluorine or chlorine. and bromine, and 1 to 9 (preferably 1 to 5) the same or different Particularly preferred are haloalkyls having one or two carbon atoms. Atoms and 1 to 5 identical or different halogens selected from fluorine and chlorine haloalkyl having atoms such as difluoromethyl, trifluoromethyl, among others; or 2,2-difluoroethyl). Further examples of halogen-substituted compounds are: is haloalkoxy, for example, OCF3, OCHF2, OCH2F, OCF2CF3, O CH2CF3, OCH2CHF2 and OCH2CH2Cl, haloalkylsulfanyl, For example, difluoromethylthio, trifluoromethylthio, trichloromethylthio, chloromethylthio Fluorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2- Difluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio Fluoroethylthio or 2-chloro-1,1,2-trifluoroethylthio, haloalkyl sulfinyl, for example, difluoromethylsulfinyl, trifluoromethylsulfinyl nyl, trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoro Oroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethyl Sulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-tri Fluoroethylsulfinyl and 2-chloro-1,1,2-trifluoroethylsulfinyl haloalkylsulfinyl, for example, difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2- difluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-Trifluoroethylsulfinyl and 2-chloro-1,1,2-trifluoro haloethylsulfinyl, haloalkylsulfonyl groups, for example, difluoromethylsulfonyl trifluoromethylsulfonyl, trichloromethylsulfonyl, chlorodifluoromethyl Fluoroethylsulfonyl, 1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2, 2-difluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and 2-chloro-1,1,2-trifluoro It is ethylsulfonyl.
[0092] In the case of radicals having carbon atoms, preference is given to radicals having 1 to 4 carbon atoms, especially 1 or Generally, halogens (e.g., fluorine and chlorine) , (C1-C4) alkyl (preferably methyl or ethyl), (C1-C4) haloal alkyl (preferably trifluoromethyl), (C1-C4)alkoxy (preferably methyl), (C1-C4)haloalkoxy, nitro and cyano. Particularly preferred are the substituents methyl, methoxy, fluorine, and chlorine.
[0093] Substituted amino (for example, mono- or di-substituted amino) can be, for example, alkyl. one or two selected from the group consisting of aryl, hydroxy, amino, alkoxy, acyl and aryl; Substituted amino radicals N-substituted by identical or different radicals of means a radical selected from the group consisting of: -dialkylamino (e.g., methylamino, ethylamino, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-propylamino, N,N-diisopropylamino amino or N,N-dibutylamino), N-monoalkoxyalkylamino or N,N-di Alkoxyalkylamino groups (e.g., N-methoxymethylamino, N-methoxyethyl Amino, N,N-di(methoxymethyl)amino or N,N-di(methoxyethyl)amino ), N-monoarylamino and N,N-diarylamino, e.g., optionally substituted Good aniline, acylamino, N,N-diacylamino, N-alkyl-N-aryl amino, N-alkyl-N-acylamino and, furthermore, saturated N-heterocycles; and, preferred are alkyl radicals having 1 to 4 carbon atoms; The aryl is preferably phenyl or substituted phenyl; and for acyl, The definitions given further below apply, preferably (C1-C4)-alkano The same applies to substituted hydroxylamino or hydrazino. will be done.
[0094] The substituted amino may further be a quaternary amino having four organic substituents on the nitrogen atom. This also includes monium compounds (salts).
[0095] The optionally substituted phenyl is preferably unsubstituted phenyl or or halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C 4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1 -C4)-Alkyl, (C1-C4)-Haloalkyl, (C1-C4)-Haloalkoxy , (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4) -Alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4) -Alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, cyano, isocyano and nitro, substituted or polysubstituted (preferably up to trisubstituted) phenyl, for example, o-triphenyl; m-tolyl and p-tolyl, dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl phenyl and 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl and 4- Fluorophenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl and 4-trifluoromethylphenyl, and 4-trichloromethylphenyl, 2,4- Dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl and 2,3- Dichlorophenyl, o-methoxyphenyl, m-methoxyphenyl and p-methoxyphenyl and 4-heptafluorophenyl.
[0096] The optionally substituted cycloalkyl is preferably an unsubstituted cycloalkyl. or halogen, cyano, (C1-C4)-alkyl, (C1-C4)-alanyl Alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4) -alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkyl and (C1- C4)-haloalkoxy, Cycloalkyl mono- or polysubstituted (preferably up to three) with dialkyl , in particular cycloalkyl substituted by one or two (C1-C4)-alkyl radicals is.
[0097] The compounds of the present invention may be present in preferred embodiments. The embodiments can be combined with each other. It does not include combinations that would be excluded based on expert knowledge. For example, combinations of three or more adjacent Ring structures containing oxygen atoms of the formula: are excluded.
[0098] Isomers The compound represented by formula (I) may exist in the form of a geometric isomer depending on the type of the substituent. and / or in the form of optically active isomers or corresponding isomeric mixtures in various compositions. These stereoisomers can also exist in the form of enantiomers, diastereomers, etc. The present invention therefore provides pure stereoisomers and Any mixtures of these isomers are included.
[0099] Methods and Uses The present invention also relates to a method for controlling pests, wherein the method comprises administering a compound of formula (I): The compound is then allowed to act on the pests and / or their habitat. is practiced in agriculture and forestry and in the protection of materials. Preferably, methods for surgical or therapeutic treatment of the human or animal body and methods for treating human or animal diseases. Diagnostic methods performed on the body of an animal are excluded from the above methods.
[0100] The present invention further relates to compounds of formula (I) as pesticides, in particular as crop protection agents. The present invention also relates to the use of compounds that are
[0101] In the context of this application, the term "pesticide" is used in each case. always also encompasses the term "crop protection agent".
[0102] Good tolerance by plants, desirable toxicity to warm-blooded animals, and good The compounds of formula (I) that exhibit environmental compatibility are capable of mitigating biotic and abiotic stressors. It is suitable for protecting plants and plant organs against loess factors and for increasing yields. It is suitable for improving the quality of crops and is also useful in agriculture and horticulture. in livestock farming, in aquaculture, in forests, in gardens and leisure facilities, in stored products Pests encountered in the protection of materials and materials, and in the field of hygiene, in particular insects, It is suitable for controlling arachnids, helminths, especially nematodes, and mollusks.
[0103] In the context of this patent application, the term "hygiene" refers to the prevention of diseases (especially infectious diseases) Any and all means, methods and practices aimed at preventing, and the prevention of, human and animal Helps protect health and / or the environment and / or maintains cleanliness It is understood to mean any and all means, methods and implementations. means for cleaning, disinfecting and sterilizing, e.g. For example, textile or hard surfaces (especially glass, wood, concrete, porcelain, ceramic) Hand tools for cleaning surfaces made of plastic or even metal(s). means for disinfecting and sterilizing the same and for preventing sanitary pests and / or Means for ensuring that the waste remains free are included. In this connection, preferably, surgical or therapeutic procedures that can be performed on the human or animal body are also included. Devices and diagnostic methods performed on the human or animal body fall within the scope of protection according to the invention. are excluded from the scope.
[0104] The term "field of hygiene" therefore includes those areas in which such hygienic means, methods and practices are important. All areas, technical and industrial applications, such as kitchens, bakeries, airports, bathrooms, Regarding hygiene in swimming pools, department stores, hotels, hospitals, livestock sheds, livestock farms, etc. This includes all areas, technical fields and industrial applications that are relevant to the invention.
[0105] Therefore, the term "sanitary pest" refers to insects whose presence is problematic in the field of hygiene, especially those is understood to mean one or more pests that are problematic for health reasons. The main purpose is to avoid or minimize the presence of sanitary pests in the field of hygiene. Controlling and / or avoiding or minimizing contact with sanitary pests This is especially important for preventing outbreaks and for tackling existing outbreaks. This can be achieved by applying insecticides that can be used for both It is also possible to use preparations that avoid or reduce contact with pests. Examples of live pests include the organisms listed below.
[0106] Thus, the term "hygienic protection" includes such hygienic means, methods and practices. This includes all actions that maintain and / or improve the quality of the product.
[0107] The compounds of formula (I) can preferably be used as pesticides They are effective against normally sensitive and resistant species and at all developmental stages. The pests may include the following: can: Pests of the Arthropoda phylum, in particular the Arachnida class, e.g., Acarus species ( Acarus spp., e.g., Acarus siro, Ake Aceria kuko, Aceria sherdonii ldoni), Aculops spp., Acul us spp.), e.g., Aculus fockeui , Aculus schlechtendali, Ann Amblyomma spp., Amphitetranychus bienensii Amphitetranychus viennensis, Argus species gas spp.), Boophilus spp., Brevipal Brevipalpus spp., e.g., Brevipalpus hoenisis (Brevipalpus phoenicis), Bryobia graminoum (Bryo bia graminum), Bryobia praetiosa (Bryobia praet iosa), Centruroides spp., Coriopsis Chorioptes spp., Dermanisus gallinae yssus gallinae), Dermatophagoides pteronyssinus (Derma tophagoides pteronyssinus), Dermatophagoides phagoides Dermatophagoides farinae, Dermacentor species ( Dermacentor spp.), Eotetranych spp. us spp.), e.g., Eotetranychu hykoriae s hicoriae), Epitrimerus pyri , Eutetranychus spp., e.g., Euteto Eutetranychus banksi, Eriophyes genus Species (Eriophyes spp.), e.g., Eriophyes pili (Eriophy es pyri), Glycyphagus domesticus (Glycyphagus dome sticus), Halotydeus destru ctor), Hemitarsonemus spp., e.g. For example, Hemitarsonemus latus (= Poly Polyphagotarsonemus latus ), Hyalomma spp., Ixodes spp. spp.), Latrodectus spp., Loxoskelet Loxosceles spp., Neutrombicula autumnalis utrombicula autumnalis, Nuphersa species spp.), Oligonychus spp., e.g., Oligonychus spp. Oligonychus coffeae, Oligonychus coffeae Oligonychus coniferarum, Oligonychus i Oligonychus ilicis, Oligonychus indicus gonychus indicus, Oligonyx mangiferus (Oligony chus mangiferus), Oligonychus platensis (Oligonych us pratensis), Oligonychus punicae (Oligonychus pu nicae), Oligonychus yothersi ), Ornithodorus spp., Ornithonisus spp. (Ornithonyssus spp.), Panonychus spp. spp.), e.g., Panonychus citri (=Me Metatetranychus citri, Panonic Panonychus ulmi (=Met atetranychus ulmi), Phyllocopterta oleivora (Phyll ocoptruta oleivora), Platytetranychus multidigitalis (Pl atytetranychus multidigituli), Polyphagotarsonem Polyphagotarsonemus latus, Psoroptes genus species (Psoroptes spp.), Rhipicephalus spp. spp.), Rhizoglyphus spp., Sarcoptes Sarcoptes spp., Scorpio maurus maurus, Steneotarsonemus sp p.), Steneotarsonemus spi nki), Tarsonemus spp., e.g., Tarsonemus Tarsonemus confusus, Tarsonemus pallidus (Tarsonemus pallidus), Tetranych species us spp.), e.g., Tetranychus canadensis (Tetranychus c anadensis), Tetranychus cinnabarinus (Tetranychus ci nnabarinus), Tetranychus tu rkestani), Tetranychus urticae ae), Trombicula alfredduge si), Vaejovis spp., Basate lycopersici ( Vasates lycopersici); From the class Chilopoda, for example, the genus Geophilus spp.), Scutigera spp.; of the order Collembola or class Collembola, e.g., Onychiurus albicilla Onychiurus armatus; Sminturus viridis nthurus viridis); From the class Diplopoda, for example, Blaniurus guttulatus ulus guttulatus); From the class Insecta, for example, from the order Blattodea, for example , Blatta orientalis, Blatta a Blattella asahinai, Blattella germanica ttella germanica), Leucophaea maderae (Leucophae a maderae), Loboptera decipiens (Loboptera decipi ens), Neostylopyga rhombifolia (Neostylopyga rhombi folia), Panchlora spp., Parcobratta spp. (Parcoblatta spp.), Periplaneta spp. spp.), e.g., Periplaneta americana (Periplaneta americana) cana), Periplaneta australasiae (Periplaneta austr alasiae), Pycnoscelus surinamensis (Pycnoscelus suri namensis), Supella longipalpa ; Coleoptera, e.g., Acalinma vitatum ymma vittatum), Acanthocerides obtectus (Acanthosc elides obtectus), Adoretus spp. Aethina tumida, Agelastica arnii astica alni), Agrilus spp., e.g. Agrilus planipennis, Agrilus planipennis Coxalis (Agrilus coxalis), Agrilus bilineatus (Agri agrilus bilineatus, agrilus anx ius), Agriotes spp., e.g., Agriotes . Linneatus (Agriotes linneatus), Agriotes mancus (A griotes mancus), Alphitobius diaperinus (Alphitob ius diaperinus), Amphimaron solstitialis (Amphima llon solstitialis), Anobium punctatum punctatum), Anoplophora spp., e.g. For example, Anoplophora glabripennis is), Anthonomus spp., e.g., Anthonomus Anthonomus grandis, Anth renus spp.), Apion spp., Apogonia spp. pogonia spp.), Atomaria spp., e.g. , Atomaria linearis, Atagenus species (A ttagenus spp.), Baris caerulescens (Baris caerule scens), Bruchidius obtectus ), Bruchus spp., e.g., Brucus pisorum chus pisorum), Bruchus rufimanus (Bruchus rufima nus), Cassida spp., Cerotoma trifulcata (Ce rotoma trifurcata), Ceutorrhync species hus spp.), e.g., Ceutorrhynchus assimilis (Ceutorrhynchus us assimilis), Ceutorrhyn chus quadridens), Ceutorhynchus rapae (Ceutorrhync hus rapae), Chaetocnema spp., e.g. For example, Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema denticulata Chaetocnema ectypa, Cleonus menzicus (Cleonus mendicus), Conoderus spp. .), Cosmopolites spp., e.g. Cosmopolites sordidus, Costelitora Zealand deer (Costelytra zealandica), Ctenicella species (Ct enicera spp.), Curculio spp., e.g. , Curculio caryae, Curculio caryatori Pes (Curculio caryatrypes), Curculio obtusus (Cur culio obtusus), Curculio sayi (Curculio sayi), Cryptolestes ferrugineus s), Cryptolestes pusillus, Cryptorhynchus lapathi, cryptorhynchus Cryptorhynchus mangiferae , Cylindrocopturus spp., Cylindrocopturus Cylindrocopturus adspersus us), Cylindrocopturus furnisi (Cylindrocopturus furnisi) nissi), Dendroctonus spp., e.g. , Dendroctonus ponderosae ), Dermestes spp., Diabrotica spp. rotica spp.), e.g., Diabrotica balteata (Diabrotica balteata), Diabrotica barberi i), Diabrotica undecimpunctata howalji (Diabrotica und ecimpunctata howardi), Diabrotica undecimpunctata Diabrotica undecimpunctata un decimpunctata), Diabrotica virgifera virgifera (Diab rotica virgifera virgifera), Diabrotica virgifera Diabrotica virgifera zeae, Dicocrosis genus species (Dichocrocis spp.), Dichocrocis armigera (Dicladi spa armigera), Diloboderus spp. , Epicaerus spp., Epilachna spp. hna spp.), e.g., Epilachna borealis (Epilachna bore alis), Epilachna varivestis , Epitrix spp., e.g., Epitrix cucumeris (Epitrix cucumeris), Epitrix fuscula (Epitrix fuscula), Epitrix hirtipennis (Epitrix hirtipen nis), Epitrix subcrinita, E Epitrix tuberis, Faustinus species ustinus spp.), Gibbium psylloides (Gibbium psyllo ides), Gnathocerus cornutus , Hellula undalis, Heteronyx alatre ( Heteronychus arator), Heteronyx sp. spp.), Hylamorpha elegans, Hylotrupes bajulus, Hypera postica (Hypera postica), Hypomeces squamousus (Hypomeces squamosus), Hypothenemus spp., e.g. For example, Hypothenemus hampei, Hypothene Mus obscurus (Hypothenemus obscurus), Hypothenemus Hypothenemus pubescens, Lachnosterna con Sanguinea (Lachnosterna consanguinea), Rashidelma Lasioderma serricorne, Laticus oryzae (Latheticus oryzae), Lathridius species spp.), Lema spp., Leptinotarsa decemlineata (Le ptinotarsa decemlineata), Leucoptera species (Leucop tera spp.), e.g., Leucoptera copheera (Leucoptera c offeella), Limonius ectypus, Lissorhoptrus oryzophilus us), Listronotus spp. (=Hyperodes spp.) (Hyperodes spp.), Lixus spp., Luperode Luperodes spp., Luperomorpha xanthodera omorpha xanthodera), Lyctus spp. Megacyllene spp., e.g., Megacyllene robinia Megacyllene robiniae, Megascelis species is spp.), Melanotus spp., e.g. Melanotus longulus oregonensis onensis), Meligethes aeneus, Melolontha spp., e.g., Melolontha melolontha (Melolontha melolontha), Migdolus sp. spp.), Monochamus spp., Naupactus ki Santographus (Naupactus xanthographus), Necrobia species (Necrobia spp.), Neogalerucella spp. spp.), Niptus hololeucus, Ori Oryctes rhinoceros, Oryzaephilus Oryzaephilus surinamensis, Oryzafag Oryzaphagus oryzae, Oti orhynchus spp.), e.g., Othiorhynchus cribricollis (Otio rhynchus cribricollis), Othiorhynchus ligusticii (Oti orhynchus ligustici), Otiorhynchus ovatus (Otiorh ynchus ovatus), Otiorhynchus rugosostialus (Otiorhy nchus rugosostriarus, Othiorhynchus sulcatus (Otio rhynchus sulcatus), Oulema spp., e.g. For example, Oulema melanopus, Oulema oryzae Oulema oryzae, Oxycetonia jukunda a jucunda, Phaedon cochlea riae), Phyllophaga spp., Phyllophaga· Phyllophaga helleri, Phyllotoreta species treta spp.), e.g., Phyllotreta armolasiae (Phyllotre ta armoraciae), Phyllotreta pusilla (Phyllotreta pu silla), Phyllotreta ramosa, Phyllotreta Phyllotreta striolata, Popilia japonica (Popillia japonica), Premnotrypes species (Prem notrypes spp.), Prostepha torncatus (Prostepha nus truncatus), Psylliodes spp. For example, Psylliodes affinis, Psylliodes affinis Psylliodes chrysocephala, P Psylliodes punctulata, Putinus Ptinus spp., Rhizobius v e ntralis), Rhizopertha dominica ), Rhynchophorus spp., Rhynchophorus phe Rhynchophorus ferrugineus, Rhynchophorus ferrugineus palmarum (Rhynchophorus palmarum), Scolytus species (Sc olytus spp.), e.g., Scolytu multistriatus (Scolytu s multistriatus), Sinoxylon perforans (Sinoxylon perforans), Sitophilus spp., e.g. For example, Sitophilus granarius, Sitophilus linearis, Sitophilus o Sitophilus oryzae, Sitophilus zeamais philus zeamais), Sphenophorus species (Sphenophorus s pp.), Stegobium paniceum, Stegobium paniceum Sternechus spp., e.g., Sternechus pardatus (Sternechus paludatus), Symphyletes species etes spp., Tanymecus spp., e.g. Tanymecus dilaticollis, Tanymeku Tanymecus indicus, Tanymecus pariatus anymecus palliatus), Tenebrio molitor (Tenebrio molitor, Tenebrioides mauretanicus (Tenebrioides m auretanicus), Tribolium spp., e.g. For example, Tribolium audax, Tribolium ka Tribolium castaneum, Tribolium confusum ( Tribolium confusum), Trogoderma sp. spp.), Tychius spp., Xyl otrechus spp.), Zabrus spp., e.g. Zabrus tenebrioides; Dermaptera, for example, Anisolabis maritime solabis maritime), Forficula auricularia (Forficu la auricularia, Labidura riparia ia); Diptera, e.g., Aedes spp., e.g. Aedes aegypti, Aedes albopictus (Aedes albopictus), Aedes sti cticus, Aedes vexans, Agromyza species (Agromyza spp.), e.g., Agromyza frontera (Agromyza frontella), Agromyza parvicornis (Agromyza parvi cornis), Anastrepha spp., Anopheles Anopheles spp., e.g., Anopheles quadrimaculatus (Anopheles quadrimaculatus), Anopheles gumbiae (Anopheles gambiae), Asphondylia species a spp.), Bactrocera spp., e.g. Bactrocera cucurbitae, Bactrocera La dorsalis (Bactrocera dorsalis), Bactrocera oleae (Bactrocera oleae), Bibio hortulanus (Bibio hort ulanus), Calliphora erythrocephala cephala), Calliphora vicina, Serratia Ceratitis capitata, Chironomus species onomus spp., Chrysomya spp., Chryso Chrysops spp., Chrysozona pluvialis ona pluvialis), Cochliomya spp. , Contarinia spp., e.g., Contarinia jo Johnsoni (Contarinia johnsoni), Contarinia nasturtii (C ontarinia nasturtii), Contari nia pyrivora), Contarinia scruzi (Contarinia sch ulzi), Contarinia sorghicola ), Contarinia tritici, Cordylovia Anthropophaga (Cordylobia anthropophaga), Krikoto Cricotopus sylvestris, Cricotopus species (Culex spp.), e.g., Culex pipiens s), Culex quinquefasciatus us), Culicoides spp., Culicateta spp. iseta spp.), Cuterebra spp., Dacus Dacus oleae, Dasineura spp. ), for example, Dasineura brassicae, De Delia spp., e.g., Delia antqua iqua), Delia coarctata, Delia flora Delia florilega, Delia plat ura), Delia radicum, Dermatobia hominis (Dermatobia hominis), Drosophila species spp.), e.g., Drosphila melanogaster (Drosphila mela nogaster, Drosophila suzukii ), Echinocnemus spp., Eureia hercules Ray (Euleia heraclei), Fannia spp. , Gasterophilus spp., Glossina spp. Glossina spp.), Haematopota spp. ), Hydrellia spp., Hydrellia griseola (Hy drellia griseola), Hylemya spp., Hippobosca spp., Hypoderma spp. ma spp.), Liriomyza spp., e.g., Lirio Liriomyza brassicae, Liriomyza phidobu Liriomyza huidobrensis, Liriomyza sativae ( Liriomyza sativae), Lucilia spp., For example, Lucilia cuprina, Lutozomyia species ( Lutzomyia spp., Mansonia spp., Mu Musca spp., e.g., Musca domestica estica), Musca domestica vi cina), Oestrus spp., Oscinella fritillaria (Os cinella frit), Paratanytarsus species spp.), Paralauterborniella subcinctus (Paralauterborni ella subcincta), Pegomia or Pegomia species Pegomyia spp., e.g., Pegomyia bet ae), Pegomya hyoscyami, Pegomya ru Pegomya rubivora, Phlebotom species us spp.), Phorbia spp., Pho rmia spp.), Piophila casei, Platycodon Platyparea poeciloptera, Project Prodiplosis spp., Psila rosae osae), Rhagoletis spp., e.g. Rhagoletis cingulata, Rhagoletis completa (Rhagoletis completa), Rhagoletis fausta (Rhagol etis fausta), Rhagoletis inferens (Rhagoletis i ndifferens), Rhagoletis menda x), Rhagoletis pomonella, Sarcof Sarcophaga spp., Simulium spp. pp.), for example, Simulium meridiona le), Stomoxys spp., Tabanus spp. s spp.), Tetanopus spp., Ti pula spp.), e.g. Tipula paludosa , Tipula simplex, Toxotrypana curvica Uda (Toxotrypana curvicauda); Hemiptera, e.g., Aciscia acaciaevaileianae (Acizzia acaciaebaileyanae), Acizzia dodonaeae ( Acizzia dodonaeae, Acizzia uncatatoides (Acizzia uncatoides), Acrida turrita, Achillea Acyrthosiphon spp., e.g., Acyrthosiphon pis Acyrthosiphon pisum, Acrogoni species a spp.), Aeneolamia spp., Agonocena Agonoscena spp., Aleurocanthus spp. thus spp.), Aleyrodes proletella (Aleyrodes prolet ella), Aleurolobus barodensis (Aleurolobus baroden sis), Aleurothrix flocco sus), Allocaridara malayensis (Allocaridara malayen sis), Amrasca spp., e.g., Amrasca biguts Amrasca bigutulla, Amrasca devastans a devastans, Anuraphis cardu i), Aonidiella spp., e.g., Aonidiella Aonidiella aurantii, Aonidiella citrina ( Aonidiella citrina, Aonidiella inornata (Aonidie lla inornata), Aphanostigma pili (Aphanostigma pili) iri), Aphis spp., e.g., Aphis citricola (A Aphis citricola, Aphis craccivora ora), Aphis fabae, Aphis holvesi his forbesi), Aphis glycines, Aphis gossypii, Aphis hederae s hederae), Aphis illinoise nsis), Aphis middletoni, Aphis Aphis nasturtii, Aphis nerii erii), Aphis pomi, Aphis spiraecola his spiraecola), Aphis viburniphila niphila), Arboridia apicalis ), Arytainilla spp., Aspidiella spp. pidiella spp.), Aspidiotus spp. ), e.g., Aspidiotus nerii, Atanus Atanus spp., Aulacorthum solani solani), Bemisia tabaci, Blastopusilla Blastopsylla occidentalis, Borei Boreioglycaspis melaleuca e), Brachycaudus helichrysi ), Brachycolus spp., Brevicoryne brassicae Brevicoryne brassicae, Cacopsy lla spp.), e.g., Cacopsylla pyri cola), Calligypona marginata , Capulinia spp., Carneocephala fulgida (C arneocephala fulgida), Ceratovacuna lanigera (Cerato vacuna lanigera), Cercopidae, Ceropla Ceroplastes spp., Chaetosiphon fragaehorii (C haetosiphon fragaefolii), Chionaspis tegalensis (C hionaspis tegalensis), Chlorita onukii (Chlorita onukii), Chondracris rosea, Chromaphis juglandicola , Chrysomphalus aonidum, Chrysomphalus ficus, Chrysomphalina Mbira (Cicadulina mbila), Coccomytilus harii (Coccom ytilus halli), Coccus spp., e.g. Coccus hesperidum, Coccus longuli ( Coccus longulus, Coccus pseudomagnoliarum (Coccus pseudomagnoliarum), Coccus virilis idis), Cryptomyzus ribis, Cryptomyzus ribis Cryptoneossa spp., Cten arytaina spp.), Dalbulus spp., Zia Dialeurodes chittendeni, Dialeurodes chittendeni Dialeurodes citri, Dialeurodes citri aphorina citri), Diaspis spp., Jiu Diuraphis spp., Doralis sp. p.), Drosicha spp., Dysaph spp. is spp.), e.g., Dysaphis apiifolia olia), Dysaphis plantaginea ), Dysaphis tulipae, Dysmicoccus spp. (Dysmicoccus spp.), Empoasca spp. .), for example, Empoasca abrupta, Em Empoasca fabae, Empoasca marigna poasca maligna), Empoasca sola na), Empoasca stevensi, Erioso Eriosoma spp., e.g., Eriosoma americanum soma americanum, Eriosoma lanigerum nigerum), Eriosoma pyricola, E Erythroneura spp., Eucalyptolima spp. ucalyptolyma spp.), Euphyllura spp. pp.), Euscelis bilobatus, Ferri Ferrisia spp., Fiorinia sp. p.), Furcaspis oceanica, Geoco Geococcus coffeae, Glycaspis species (Gl ycaspis spp.), Heteropsylla cubana (Heteropsylla cu bana), Heteropsylla spinulosa a), Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus arundinis Hyalopterus pruni, Icery species a spp.), e.g., Icerya purchasi, I Idiocerus spp., Idioscopus spp. opus spp.), Laodelphax striatellus triatellus), Lecanium spp., e.g. Lecanium corni (= Parthenolecanium corni ( Parthenolecanium corni), Lepidosafes species osaphes spp.), e.g., Lepidosaphes ulmi (Lepidosaph es ulmi), Lipaphis erysimi, Rojo Leucasspis japonica (Lopholeucaspis japonica), Rico Lycorma delicatula, Macrosiphum species crosiphum spp.), e.g., Macrosiphum euphorbiae (Macro siphum euphorbiae, Macrosiphum lily m lilii), Macrosiphum rosae, Ma Macrosteles facifrons, Maha Narva spp., Melanaphis sacchari phis sacchari), Metcalfiella species (Metcalfiella s pp.), Metcalfa pruinosa, Metopo Metopolophium dirhodum, Moneria Monellia costalis, Monelliopsis pecanis nelliopsis pecanis), Myzus spp., e.g. Myzus ascalonicus, Myzus cerasi (Myzus cerasi), Myzus ligustri , Myzus ornatus, Myzu persicae s persicae), Myzus nicotianae , Nasonovia ribisnigri, Neomass Neomaskellia spp., Nephotetchchis spp. tettix spp.), e.g., Nephote tettix cincticeps (Nephote ttix cincticeps), Nephotettix nigropictus (Nephote ttix nigropictus), Nettigonicera spectre (Nettigoni clla spectra), Nilaparvata lugens (Nilaparvata lu gens), Oncometopia spp., Orthezia Orthezia praelonga, Oxya chinensis ya chinensis), Pachypsylla spp., Parabemisia myricae, Paratoliosa genus Species (Paratrioza spp.), e.g., Paratrioza cockleri (Para trioza cockerelli), Parlatoria spp. pp.), Pemphigus spp., e.g., Pemphigus Pemphigus bursarius, Pemphigus popplii Pemphigus populivenae, Peregrinus mykiss (Pe regrinus maidis), Perkinsiella species spp.), Phenacoccus spp., e.g. Na Phenacoccus madeirensis, pro Phloeomyzus passerinii, Holod Phorodon humuli, Phylloxera species ra spp.), e.g., Phylloxera devastratrichis devastatrix, Phylloxera notabilis (Phylloxera no tabilis), Pinnaspis aspidistrae (Pinnaspis aspid istrae), Planococcus spp., e.g. Planococcus citri, Prosopidopsilla Flava (Prosopidopsylla flava), Protopulvinaria pyrifolia Lummis (Protopulvinaria pyriformis), Pseudauracus Pseudaulacaspis pentagona, Pseudaulacaspis pentagona Pseudococcus spp., e.g., Pseudococcus ka Pseudococcus calceolariae, Pseudococcus Pseudococcus comstocki, Pseudococcus comstocki Pseudococcus longispinus, Pseudococcus longispinus Pseudococcus maritimus, Pseudococcus Pseudococcus viburni, Psilopsis genus Psyllopsis spp., Psylla spp., e.g. For example, Psylla buxi, Psylla mal i), Psylla pyri, Pteromal species us spp.), Pulvinaria spp., Pillira spp. (Pyrilla spp.), Quadraspidio tus spp.), e.g., Quadraspiziotus juglansregiae (Quad raspidiotus juglansregiae), Quadraspidiotus male Treaeformis (Quadraspidiotus ostreaeformis), Quadraspidiotus pernisiosus ciosus), Quesada gigas, Lastrococus Rastrococcus spp., Rhopalosi spp. phum spp.), e.g., Rhopalosiphum maydis maidis), Rhopalosiphum oxyacanthae (Rhopalosiphum o xyacanthae), Rhopalosiphum padi ), Rhopalosiphum rufiabdminare (Rhopalosiphum rufiabd ominale), Saissetia spp., e.g., Saissetia Saissetia coffeae, Saissetia miranda (S Saissetia miranda), Saissetia neglecta (Saissetia neglecta), Saissetia oleae, Ska Scaphoideus titanus, Scaphoideus g Schizaphis graminum, Serenaspizus alticulata Selenaspidus articulatus, Siph flava a flava), Sitobion avenae, Sogata Sogata spp., Sogatella fucifera rcifera), Sogatodes spp., Stictocepha La Festina (Stictocephala festina), Siphoninus philippinarum Siphoninus phillyreae, Tenaraphala maraiensi Tenalapha malayensis, Tetragonocephalus species tragonocephela spp.), Tinocaris cariaehoriae (Tino callis caryaefoliae), Tomaspis sp. p.), Toxoptera spp., e.g., Toxoptera Toxoptera aurantii, Toxoptera citricidus (Toxoptera citricidus), Trialeurodes vaporariorum ( Trialeurodes vaporariorum, Trioza species spp.), e.g., Trioza diospyri, Chi Typhlocyba spp., Unaspis spp. spp.), Viteus vitifolii, Zigina spp. (Zygina spp.); The suborder Heteroptera, for example, Aelia spp. pp.), Anasa tristis, Anthethiopsis spp. species (Antestiopsis spp.), Boisea spp. , Blissus spp., Calocoris spp. spp.), Campylomma livida, Caveleri Cavelerius spp., Cimex spp. , e.g., Cimex adjunctus, Cimex Hemipterus (Cimex hemipterus), Cimex rectularius (C Cimex lectularius), Cimex pilos ellus), Collaria spp., Creontiades jill Creontiades dilutus, Dasynu piperis s piperis), Dichelops furcatus s), Diconocoris hewetti, Diconocoris hewetti Dysdercus spp., Euschistus spp. us spp.), e.g., Euschistus herous s), Euschistus servus, Euschistus Euschistus tristigmus, Euschistus Euschistus variolarius, Eurydema genus species (Eurydema spp.), Eurygaster sp p.), Halyomorpha halys, Heliopal Heliopeltis spp., Horci as nobilellus), Leptocorisa spp. ), Leptocorisa varicornis, Leptoglossus occidentalis is), Leptoglossus phyllopus ), Lygocoris spp., e.g., Lygocoris pubulnii Lygocoris pabulinus, Lygus spp. For example, Lygus elisus, Lygus hesperus gus hesperus, Lygus lineolari s), Macropes excavatus, Megaco Megacopta cribraria, Miridae dae), Monalonion atratum, Nezha Nezara spp., e.g., Nezara virizura idula), Nysius spp., Oebalus spp. us spp.), Pentomidae, Piesma quadrata (P iesma quadrata), Piezodorus spp. ), for example, Piezodorus guildinii ), Psallus spp., Pseu dacysta persea), Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinoho Scotinophora spp., Stepha pear nitis nashi), Tibraca spp., Triatoma spp. Species (Triatoma spp.); Hymenoptera, for example, Acromyrmecichus species rmex spp.), Athalia spp., e.g., Athalia Athalia rosae, Atta spp., Campo Camponotus spp., Dolichovespula spp. vespula spp.), Diprion spp., e.g. Diprion similis, Hoplopha species locampa spp.), e.g., Hoplocampa kookaei (Hoplocampa cookei), Hoplocampa testud inea), Lasius spp., Linepithema (Iridiomyrmecium Linepithema (Iridiomyrmex) humile , Monomorium pharaonis, Parato Paratrechina spp., Paravespra spp. spula spp.), Plagiolepis spp., Sirex spp., e.g., Sirex noctilio noctilio, Solenopsis invicta a), Tapinoma spp., Technomyrmecides albipes ( Technomyrmex albipes, Urocerus species pp.), Vespa spp., e.g., Vespa crabro a crabro), Wasmannia auropunctata (Wasmannia auro punctata), Xeris spp.; Isopoda, e.g., Armadillidium vulgare (Arma dillidium vulgare, Oniscus asellus ellus), Porcellio scaber; From the order Isoptera, for example, Coptotermes species mes spp.), e.g., Coptotermes formosanus formosanus, Cornitermes cumulans (Cornitermes c umulans), Cryptotermes spp., Incisitermes spp., Ka lotermes spp.), Microtermes oveci (Microtermes o besi), Nasutitermes spp., Odontothe Odontotermes spp., Porote rmes spp.), Reticulitermes spp. .), for example, Reticulitermes flavipes (Reticulitermes fla vipes, Reticulitermes hes perus); Lepidoptera, e.g., Achro ia grisella), Acronicta major ), Adoxophyes spp., e.g., Adoxophyes Adoxophyes orana, Aedes leucomelas ia leucomelas), Agrotis spp., e.g. , Agrotis segetum, Agrotis epsilon (Agrotis ipsilon), Alabama spp., e.g. For example, Alabama argillacea, Amieloi Amyelois transitella, Anarcia species (A narsia spp.), Anticarsia spp., For example, Anticarsia gemmatalis ), Argyroploce spp., Autographa spp. Autographa spp.), Barathra brassicae (Barathra bra ssicae), Blastodacna atra, Boll Borbo cinnara, Bulatrix tulbergii cculatrix thurberiella), Bupa piniarius (Bupa lus piniarius), Busseola spp., Kako Cacoecia spp., Caloptilia teivora lia theivora), Capua reticulana ), Carpocapsa pomonella, Carposi Carposina niponensis, Carposina niponensis Mata (Cheimatobia brumata), Chilo spp. For example, Chilo plejadellus, Chilo sp lessaris (Chilo suppressalis), Coleucis pariana (Cho reutis pariana), Choristoneura sp. spp.), Chrysodeixis chalcites es), Clysia ambiguella, Cunafaro Cnaphalocerus spp., Cnaphalocerus medinarii Cnaphalocrocis medinalis, Cnephasia species phasia spp.), Conopomorpha spp. ), Conotrachelus spp., Copitarsia spp. (Copitarsia spp.), Cydia spp., e.g. Cydia nigricana, Cydia pomonella a pomonella), Dalaca noctuides ), Diaphania spp., Dipa ropsis spp.), Diatraea saccharalis (Diatraea sacc haralis), Dioryctria spp., e.g. Dioryctria zimmermani, Airy Earias spp., Ecdytropha aurantium lopha aurantium, Elasmopalpus lignocellus (Elasmop alpus lignosellus), Eldana saccharina charina), Ephestia spp., e.g. Ephestia elutella, Ephestia quaeniae Ephestia kuehniella, Epinotia species spp.), Epiphyas postvittan a), Erannis spp., Oerskobiella musculana (E rschoviella musculana), Etiella sp. p.), Eudocima spp., Eulia spp. spp.), Eupoecilia ambiguel la), Euproctis spp., e.g. Euproctis chrysorrhoea, Euproctis species (Euxoa spp.), Feltia spp., Galleria meliloti Galleria mellonella, Gracilaria species laria spp.), Grapholitha spp., e.g. For example, Grapholita molesta, Grapholita pu Grapholita prunivora, Hedyl spp. epta spp.), Helicoverpa spp., e.g. For example, Helicoverpa armigera, Helicoverpa Helicoverpa zea, Heliothi species s spp.), e.g., Heliothis virescens ens), Hofmannophila pseudospretella (Hofmannophila ps eudospretella), Homoeosoma spp. , Homona spp., Hyponomeuta padera ta padella), Kakivoria flavofasciata (Kakivoria fla vofasciata), Lampides spp., Rafigma Genus species (Laphygma spp.), Laspeyres ia molesta), Leucinodes orb onalis, Leucoptera spp., e.g., Leucoptera Leucoptera coffeella, Lithocoletis spp. Species (Lithocolletis spp.), e.g., Lithocolletis brancaldera (Lithocolletis blancardella), Lithophane antennina Lithophane antennata, Lobesia spp. pp.), e.g., Lobesia botrana, Loxag Loxagrotis albicosta, Lymantria genus Species (Lymantria spp.), e.g., Lymantria dispar (Lymant ria dispar), Lyonetia spp., e.g. Lyonetia clerkella, Malacosoma neus Malacosoma neustria, Malca testularis ca testulalis), Mamestra brassicae (Mamestra bras sicae), Melanitis leda, Mo cis spp.), Monopis obviella, Mythimna separata, Nemapogon croacellus (Nemapogon cloacellus), Nymphula spp. pp.), Oiketicus spp., Onphysa spp. phisa spp.), Operophtera spp., O Oria spp., Orthaga spp., Ost Ostrinia spp., e.g., Ostrinia nubilalis (Os trinia nubilalis), Panolis flammea (Panolis fla mmea), Parnara spp., Pectinophora spp. inophora spp.), e.g., Pectinophora gossipiera (Pectino phora gossypiella), Perileucoptera species (Perileucoptera species tera spp.), Phthorimaea spp., e.g. For example, Phthorimaea operculella , Phyllocnistis citrella, Phyllonorycter spp., e.g., Phyllonory Phyllonorycter blancardella , Phyllonorycter crataege lla), Pieris spp., e.g., Pieris rapae (Pi eris rapae), Platynota stulta na), Plodia interpunctella ), Plusia spp., Plutella xylostella la xylostella)(=Plutella macripennis (Plutella ma culipennis), Podesia spp., e.g., Podesia Podesia syringae, Prays species spp.), Prodenia spp., Protoparce spp. otoparce spp.), Pseudaletia spp. .), for example, Pseudaletia unipuncta (Pseudaletia unipun cta), Pseudoplusia includens (Pseudoplusia inclu dens), Pyrausta nubilalis, Raki Rachiplusia nu, Schoenobia species bius spp.), e.g., Schoenob bipunctifer (Schoenob ius bipunctifer), Scirpophaga sp. p.), e.g., Scirpophaga innotata a), Scotia segetum, Sesamia species mia spp., e.g., Sesamia inferens ens), Sparganothis spp., Spodoptera Spodoptera spp., e.g., Spodoptera ellagiana (Spo doptera eradiana), Spodoptera exigua a exigua), Spodoptera frugiperda (Spodoptera frugi perda), Spodoptera praefica ), Stathmopoda spp., Stenoma spp. oma spp.), Stomopteryx subesivera (Stomopteryx su bsecivella), Synanthedon spp., Te Tecia solanivora, Thaumatopoea species umetopoea spp.), Thermesia gemmatalis (Thermesia g emmatalis), Tinea cloacella, Tinea Tinea pellionella, Tinea bisselliera ineola bisselliella), Tortrix sp. p .), Trichophaga tapetzella, Trichoplusia spp., e.g., Trichoplusia Trichoplusia ni, Trypor yza incertulas), Tuta absoluta, Viracola spp.; Orthoptera or Saltatoria, for example, Aketa Acheta domesticus, Dichlopulus species roplus spp.), Gryllotalpa spp., For example, Gryllotalpa gryllotalpa a), Hieroglyphus spp., Locusta spp. ocusta spp.), e.g., Locusta migratoria (Locusta mig ratoria, Melanoplus spp., e.g. Melanoplus devastator, Paratra Paratlanticus ussuriensis, Schistocerca gregaria; From the order Phthiraptera, for example, Damalinia species ia spp.), Haematopinus spp., Rhino Linognathus spp., Pedicul us spp.), Phylloxera vasta trix), Phthirus pubis, Trichodectes species (Trichodectes spp.); From the order Psocoptera, for example, Lepinotus species tus spp.), Liposcelis spp.; From the order Siphonaptera, for example, Ceratophyllus species phyllus spp.), Ctenocephalides spp. spp.), e.g., Ctenocephalides canis (Ctenocephalide s canis), Ctenocephalides felis (Ctenocephalides felis), Pulex irritans, Tunga pene Tunga penetrans, Xenops ylla cheopis); Thysanoptera, e.g., Anaphotryps obscurus Anaphothrips obscurus, Variothrips biformis (B aliothrips biformis), Caetanahothrips leeuweni (Ch aetanaphothrips leeuweni), Drepanothrips leeuweni ( Drepanothrips reuteri), Enneothrips flavens (En neothrips flavens), Frankliniella species lla spp.), e.g., Frankliniella fusca (Frankliniella fusca), Frankliniella occidentalis (Frankliniella occidentalis), Franklinie sculptosa (Franklinie lla schultzei), Frankliniela tritici (Frankliniel la tritici), Frankliniella bassinii (Frankliniella vaccinii), Frankliniella williamsii (Frankliniella williamsi), Haplothrips spp., He Heliothrips spp., Heliothrips femora Squirrel (Hercinothrips femoralis), Chacothrips species (Kak othrips spp.), Rhipiphorothrips cruentatus (Rhipiphor othrips cruentatus), Scirtothri species ps spp.), Taeniothrips cardamomum damomi), Thrips spp., e.g., Thrips palmi (Thrips palmi), Thrips tabaci; Zygentoma (=Thysanura), e.g., Ctenolepisma Genus species (Ctenolepisma spp.), Lepisma saccharina (Lepisma saccharina), Lepismodes inquilinus (Lepismodes i nquilinus, Thermobia domestica ca); From the class Symphyla, for example, Scutigere species lla spp.), e.g., Scutigerella inmaculata immaculata); Pests of the phylum Mollusca, e.g., Bivalvia For example, Dreissena spp.; and also Gastropoda, for example, Arion spp. .), for example, Arion ater rufus, Bio Biomphalaria spp., Bulinus spp. us spp.), Deroceras spp., e.g. Deroceras laeve, Galba spp. ), Lymnaea spp., Oncomelania spp. lania spp.), Pomacea spp., Succinea spp. (Succinea spp.); Plant pests of the phylum Nematoda (i.e., plant-parasitic nematodes), especially Aggrenota Aglenchus spp., e.g., Aglenchus agricola (A glenchus agricola), Anguina spp. For example, Anguina tritici, Aphelenkoi Aphelenchoides spp., e.g., Aphelenchoides Aphelenchoides arachidis, Aphelenchoide Aphelenchoides fragariae, Belonolli Mus species (Belonolaimus spp.), e.g., Belonolaimus gracilis Belonolaimus gracilis, Belonolaimus longicaudatus Belonolaimus longicaudatus, Belonolaimus norvegicus Toni (Belonolaimus nortoni), Bursafelencus species (Bur saphelenchus spp.), e.g., Bursaphelenchus coccophyllus ( Bursaphelenchus cocophilus), Bursaphelenchus elegans Mus (Bursaphelenchus eremus), Bursaphelenchus xylo Bursaphelenchus xylophilus, Cacopaurus genus Cacopaurus spp., e.g., Cacopaurus pestis (Cacop aurus pestis), Criconemella spp. ), for example, Criconemella curvata, Criconemella onoensis, Crico Criconemella ornata, Criconemella lucius Criconemella rusium, Criconemella xenoplakis (Cr iconemella xenoplax)(=Mesocriconema xenoplakis(Me socriconema xenoplax), Criconnemoides species (Cricon emoides spp.), e.g., Cricon emoides ferniae (Cricon emoides ferniae), Criconemoides onoense (Criconem oides onoense), Criconemoides ornatum (Criconemoi des ornatum), Ditylenchus spp. For example, Ditylenchus dipsaci, Dolicho Dolichodorus spp., Globodera spp. ra spp.), e.g., Globodera pallida ), Globodera rostochiensis ), Helicotylenchus spp., e.g. Helicotylenchus dihystera , Hemicriconemoides spp., Hemi Hemicycliophora spp., Heterodera spp. eterodera spp.), e.g., Heterodera avenae (Heteroder a avenae), Heterodera glycine s), Heterodera schachtii, Hills Hirschmaniella spp., Hoplolimus spp. oplolaimus spp.), Longidorus spp. .), e.g., Longidorus africanu s), Meloidogyne spp., e.g., Meloidogyne Meloidogyne chitwoodi, Meloidogyne phala Rachis (Meloidogyne fallax), Meloidogyne hapula (Meloi dogyne hapla), Meloidogyne incognita (Meloidogyne incognita), Meloinema spp., Nacobbus Nacobbus spp., Neotylenchus spp. spp.), Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp. Species (Paratrichodorus spp.), e.g., Paratrichodorus minor (Paratrichodorus minor), Paratylenchus species (Paraty lenchus spp.), Pratylenchus spp. .), for example, Pratylenchus penetrance (Pratylenchus penetrance) rans), Pseudohalenchus spp., Psilenchus spp., Punct odera spp.), Quinisulcius spp. ), Radopholus spp., e.g., Radopholus citro Radopholus citrophilus, Radopholus similis ( Radopholus similis), Rotylenchu spp. lus spp.), Rotylenchus spp., Scute Scutellonema spp., Subanguina spp. uina spp.), Trichodorus spp., e.g. For example, Trichodorus obtusus, Trichodorus Trichodorus primitivus, Chilencolyne Tylenchorhynchus spp., e.g., Tylenchorhynchus Tylenchorhynchus annulatus, Chilench Tylenchulus spp., e.g., Tylenchulus semipennetra ance (Tylenchulus semipenetrans), Xiphinema species (X iphinema spp.), e.g., Xiphinema index (Xiphinem a index).
[0108] The compounds of formula (I) may optionally be used to remove the May also be used as an herbicide, safener, growth regulator or agent for improving plant properties or a microbicide or gametocide e) as, for example, fungicides, antifungal agents, c) Bactericides or viricides (which also include agents acting against viroids) or to treat MLO (mycoplasma-like organisms) and RLO (rickettsiae Where appropriate, they may also be used as agents against other activating compounds. They can also be used as intermediates or precursors for the synthesis of products.
[0109] formulation The present invention further provides a pesticide comprising at least one compound of formula (I): Formulations as pesticides and application forms prepared from such formulations (e.g., drench solutions, drip solutions, etc.) Optionally, the use forms may contain further pesticides and / or spray solutions. , adjuvants that improve the effect, such as penetrating agents, for example, vegetable oils (e.g., rapeseed oil) , sunflower oil), mineral oil (e.g., paraffin oil), vegetable fatty acid alkyl esters (e.g., For example, rapeseed oil methyl ester or soybean oil methyl ester), or alkanol alcohol siloxanes and / or spreading agents, such as alkylsiloxanes and / or salts, e.g. For example, organic or inorganic ammonium or phosphonium salts (e.g., ammonium sulfate or diammonium hydrogen phosphate, and / or retention promoters other) (e.g., dioctyl sulfosuccinate or hydroxypropyl guar polymer ), and / or wetting agents (e.g., glycerol), and / or fertilizers (e.g., ammonia), fertilizer containing ammonium, potassium or phosphorus.
[0110] Conventional formulations are, for example: aqueous solutions (SL), emulsifiable concentrates (EC), Oil-in-water emulsion (EW), suspension formulation (SC, SE, FS, OD), water dispersible granule ( WG), granules (GR), and capsule concentrates es)(CS); these and other possible formulations are described, for example, in Crop Life International and in Pe sticide Specifications, Manual on develo pment and use of FAO and WHO specificati ons for pesticides, FAO Plant Production and Protection Papers -173(Source: the FAO / WHO Joint Meeting on Pesticide Specifica tions, 2004, ISBN:9251048576). The preparation comprises a compound of formula (I): In addition to one or more of the compounds shown, optionally contain further pesticidal active compounds .
[0111] These are preferably free of adjuvants such as extenders, solvents, spontaneous promoters, etc. Neity promoter), carrier, emulsifier, dispersant, antifreeze (frost p protectants), biocides, thickeners and / or other auxiliary agents (e.g., adjuvants In this context, adjuvants are formulations or forms of use that contain A component that enhances the biological effect of the formulation, and which itself has a biological effect. Examples of adjuvants include those that retain, spread, or adhere to the leaf surface. agents that enhance penetration or agents that enhance penetration.
[0112] These preparations can be prepared in a known manner, for example by incorporating a compound of formula (I) into an adjuvant, such as Bulking agents, solvents and / or solid carriers, and / or other adjuvants, such as surfactants Such formulations may be prepared in suitable equipment or , prepared before or during application.
[0113] The adjuvants used may be formulations of the compounds of formula (I) or products prepared from such formulations. Use form (e.g., ready-to-use pesticides, e.g., , spray or seed dressing product) have special properties, e.g. particular physical, technical and The substance may be suitable for imparting biological properties and / or other properties.
[0114] Suitable extenders include, for example, water and polar and non-polar organic chemical liquids, such as: Selected from the following classes: aromatic and non-aromatic hydrocarbons (e.g., para- and chloro- fins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohol and polyols, which may, where appropriate, be substituted and etherified. and / or esterified), ketones (e.g., acetone, toluene, cyclohexanone), esters (which include fats and oils) and (poly i) Ethers, unsubstituted and substituted amines, amides, lactams (e.g., N-alkylpyrrolidones) and lactones, sulfones, and sulfoxides (e.g., dimethyl sulfoxide), carbonates and nitriles.
[0115] When the extender used is water, an organic solvent, for example, can also be used as a co-solvent. Essentially, suitable liquid solvents are: aromatic compounds, e.g. xylene; toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic carbon hydrogen, for example, chlorobenzenes, chloroethylenes or methylene chloride, aliphatic carbons Hydrogen, for example, cyclohexane or paraffins, for example, mineral oil fractions, mineral oils and vegetable oils Oils, alcohols, e.g. butanol or glycols and their ethers and esters esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, sulfoxides, carbonates, such as propylene carbonate, butylene carbonate, diethyl carbonate, or dibutyl carbonate, or nitriles, such as acetonitrile or propane nitrile Lil.
[0116] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons Hydrogen or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methyl chloride hydrocarbons such as cyclohexane, paraffins, petroleum fractions, mineral oils and vegetable oils. Oils, alcohols such as methanol, ethanol, isopropanol, and butanol or glycols and their ethers and esters, ketones, e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as diethyl ketone, Methyl sulfoxide, carbonates such as propylene carbonate, butylene carbonate, dicarbonate ethyl or dibutyl carbonate, nitriles such as acetonitrile or propanediol tolyl, and also water.
[0117] In principle, all suitable carriers can be used. Useful carriers include, in particular, Examples of suitable ammonium salts include ammonium salts and ground cereals. Natural minerals, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, Morillonite or diatomaceous earth, and ground synthetic materials such as finely ground silica, Alumina and natural or synthetic silicates, resins, waxes, and / or solid fertilizers Mixtures of such carriers may be used as well. Useful carriers for granules include: Examples include: crushed and separated natural rocks, e.g. , calcite, marble, pumice, sepiolite, dolomite, and composites of inorganic and organic coarse meals. Granules, as well as organic materials (e.g., sawdust, paper, coconut shells, corn, etc.) Granules made from cereals such as barley cobs and tobacco petioles.
[0118] It is also possible to use liquefied gas extenders or solvents. Particularly suitable extenders or carriers The body may be a bulking agent or carrier that is gaseous at ambient temperature and atmospheric pressure, e.g., an aerosol propellant. Gases such as halohydrocarbons, and also butane, propane, nitrogen and carbon dioxide And so on.
[0119] Emulsifiers and / or foam formers, dispersants or with ionic or non-ionic properties Examples of wetting agents or mixtures of these surfactants are: Polyacrylamide salts of lignosulfonic acid, salts of lignosulfonic acid, phenolsulfonic acid or naphthalenesulfonic acid Salts of acids, polycondensates of ethylene oxide and fatty alcohols or polycondensates of ethylene oxide and fatty Polycondensation products of fatty acids or polycondensation products of ethylene oxide and fatty amines, of substituted phenols (preferably alkylphenols or arylphenols) Polycondensation products, salts of sulfosuccinate esters, taurine derivatives (preferably alkyl taurine) esters), isethionate derivatives, phosphate esters or polyethoxylated alcohols Phosphate esters of ethoxylated phenols, fatty esters of polyols, and acetyl sulfates Derivatives of the compounds containing anions, sulfonate anions and phosphate anions, e.g. , alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfonates Phosphates, aryl sulfonates, protein hydrolysates, lignosulfite waste liquid and methylcellulose. One of the compounds represented by formula (I) and / or the inactive If one of the polymeric carriers is water-insoluble and application is by water, a surfactant may be present. It is advantageous to have it present.
[0120] Further adjuvants in the formulations and in the use forms derived therefrom include colorants, For example, inorganic pigments such as iron oxide, titanium oxide and Prussian blue n Blue), and organic dyes such as alizarin dyes, azo dyes and metal phthalo dyes. cyanine dyes, and nutrients and micronutrients, such as iron salts, manganese salts, boron salts, Copper salts, cobalt salts, molybdenum salts, zinc salts, and the like can be used.
[0121] Further ingredients may include stabilizers (e.g., low-temperature stabilizers), preservatives, antioxidants, light stabilizers, or may be another agent that improves chemical and / or physical stability. A foaming or defoaming agent may also be present.
[0122] The preparation and the use form derived from the preparation may contain, as additional adjuvants, adhesives, For example, carboxymethylcellulose, and powder, granules, or latex Natural and synthetic polymers in the form of e.g., gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids, such as cephalin and lecithin, and Synthetic phospholipids and the like can also be present. Further possible adjuvants are mineral oils and vegetable oils. It's oil.
[0123] Optionally, further adjuvants are also present in the formulation and in the use forms derived therefrom. Examples of such additives include fragrances, protective colloids, binders, etc. agents, adhesives, thickeners, thixotropic agents, penetrating agents, retention promoters, stabilizers, sequestering agents, complexing agents In general, the compounds of formula (I) are used as pharmaceutical agents. The composition may be combined with any solid or liquid additive commonly used in the art.
[0124] Useful retention aids include any material that reduces dynamic surface tension (e.g., sulfosuccinate). dioctyl ester) or any substance that increases viscoelasticity (e.g., hydroxypropyl guar Polymers) are included.
[0125] In the context of the present invention, suitable penetrants are those which are capable of enhancing the penetration of the pesticidal active compound into the plant. In this context, penetrants are all substances that are commonly used for These compounds penetrate into the plant cuticle from the (aqueous) application solution and / or from the spray coating. the ability to penetrate the skin and thereby enhance the intracuticular mobility of the active compound. To confirm this property, we used the literature (Baur et al., 1999). 97, Pesticide Science 51, 131-152) Examples of such methods include the use of alcohol alkoxylates, e.g. , coconut fatty ethoxylate ) (10) or isotridecyl ethoxylate (12), fatty acid esters, such as Rapeseed oil methyl ester or soybean oil methyl ester, fatty amine alkoxylate , for example, tallow amine ethoxylate (15), or ammonium salts and / or phosphates. sulfonium salts, such as ammonium sulfate or diammonium hydrogen phosphate; It is possible.
[0126] The preparation preferably contains 0.00000001% by weight to 9% by weight based on the weight of the preparation. 8% by weight of the compound of formula (I), or particularly preferably 0.01% by weight The composition preferably contains 0.5 to 95% by weight of the compound represented by formula (I). The composition contains 100% to 90% by weight of the compound represented by formula (I).
[0127] The compound represented by formula (I) in the use form prepared from the formulation (especially a pesticide) The content of the compound of formula (I) in the formulation can vary within a wide range. The concentration of the compound is generally 0.00000001% by weight based on the weight of its use form. up to 95% by weight of the compound represented by formula (I), preferably 0.00001% by weight to 1% by weight % of the compound of formula (I). The compound can be prepared by a conventional method suitable for the form of use. Use it.
[0128] mixture The compounds of formula (I) may be used, for example, in combination with a prolonged action to broaden the spectrum of action. To increase the duration, speed of action, and repulsion Use one or more suitable fungicides, fungicides, or fungicides to prevent the development of resistance. Bactericides, acaricides, molluscicides, nematicides, insecticides, microbiocides oculars), beneficial species, herbicides, fertilizers, bird repellents, plant enhancers (phytotoni c) in mixtures with sterilants, safeners, semiochemicals and / or plant growth regulators Furthermore, such active compound combinations can be used to improve plant growth. and / or tolerance to abiotic factors (e.g., high or low temperatures), Improving tolerance to drought or increased water content or soil salinity Furthermore, it is possible to improve flowering and fruiting performance, and germination ability. It is also possible to optimize the strength and root development, and to facilitate harvesting, It is possible to improve yield, influence maturity and It is also possible to improve the quality and / or nutritional value of the harvested produce. It may also increase shelf life and / or improve the processability of the harvested product It is also possible to do this.
[0129] Additionally, the compounds of formula (I) may be used in combination with other active compounds or semiochemicals (e.g., derivatives). attractants, and / or bird repellents, and / or plant activators, and / or growth regulators, and The compound represented by formula (I) can also be present in a mixture with a fertilizer (and / or fertilizer). The compounds are used to improve plant characteristics (e.g., growth, yield, and quality of the crop). It is also possible to use
[0130] In a particular embodiment according to the invention, the compound of formula (I) is present in the formulation or In the use forms prepared from such formulations, further compounds (preferably those described below) may be present. It exists in a mixed state with other compounds (compounds listed).
[0131] When one of the compounds described below can exist in various tautomeric forms , and in each case, even if not explicitly mentioned, these forms are equally included. Furthermore, all named mixing partners are possible due to their functional groups. If possible, salts can also be formed with suitable bases or acids.
[0132] Insecticides / Acaricides / Nematicides The active compounds identified herein by "common names" are known and For example, the pesticide handbook ("The Pesticide Manual” 16th Ed., British Cro p Protection Council 2012) or It can be found on the internet (e.g., http: / / www.alanw ood.net / pesticides). The classification was The latest IRAC Mode of Action Classification It is based on the "Scheme".
[0133] (1) Acetylcholinesterase (AChE) inhibitors, preferably Carbamates, including alanycarb, aldicarb, bendiocarb, and benflaca Rub, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbos fluphen, ethiofencarb, fenobucarb, formetanate, furathiocarb, ibuprofen Soprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, Lopoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XM C and xylylcarb; or Organic phosphate esters, such as acephate, azamethiphos, azinphos-ethyl, Azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlor Mephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, dimethicone Azinone, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famfur, Fenamiphos, Fen Nitrothion, fenthion, fosthiazate, heptenophos, imidazophos, isofen Nphos, O-(methoxyaminothiophosphoryl) salicylate isopropyl, isoxathio malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos methicone, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate phosalone, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methionine le, profenofos, propetamfos, prothiofos, pyraclofos, pyridaphenthio quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlor Selected from vinphos, thiometon, triazophos, trichlorfon and vamidothion .
[0134] (2) GABA-regulated chloride channel blockers, preferably Cyclodiene-organochlorine, selected from chlordane and endosulfan or Phenylpyrazoles (Fiproles) such as Ethiprole and Fipronil.
[0135] (3) sodium channel modulators, preferably Pyrethroids, which include acrinathrin, allethrin, and d-cis-trans allethrin d-transallethrin, bifenthrin, bioallethrin, bioallethrin s- Cyclopentenyl isomers, bioresmethrin, cycloprothrin, cyfluthrin, beta -Cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cyper Methrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], delta Methrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, Tofenprox, fenpropathrin, fenvalerate, flucythrinate, flu Methrin, Tau-fluvalinate, Halfenprox, Imiprothrin, Kadetrin , momfluorotrin, permethrin, phenothrin [(1R)-trans-isomer], Prallethrin, pyrethrins (pyrethrum), resmethrin, Silaf Luofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-isomer], selected from larometrin and transfluthrin; or DDT; or methoxychlor.
[0136] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, preferably Or, Neonicotinoids, which include acetamiprid, clothianidin, dinotefuran, and imipenem. selected from dacloprid, nitenpyram, thiacloprid and thiamethoxam; or , nicotine; or Sulfoxaflor or flupyradifurone.
[0137] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators -, preferably, Spinosyns, which are selected from spinetoram and spinosad.
[0138] (6) Allosteric modulation of glutamate-regulated chloride channels (GluCl) Tar, preferably Avermectins / milbemycins, which include abamectin, emamectin benzoate The compound is selected from the group consisting of lepimectin and milbemectin.
[0139] (7) Juvenile hormone mimetics, preferably Juvenile hormone analogs selected from hydroprene, kinoprene and methoprene. or Fenoxycarb; or pyriproxyfen.
[0140] (8) Various unspecified (multi-site) inhibitors, preferably Alkyl halides, selected from methyl bromide and other alkyl halides or Chloropicrin; or sulfuryl fluoride; or borax; or tartar emetic; or Methyl isocyanate generating substances, which are diazomet and metham are selected.
[0141] (9) Chordotonal organ TRPV channel modulators, including pymetrozine and pyrimidine fluquinazone.
[0142] (10) Mite growth inhibitors, such as clofentezine, hexythiazox, and diflovir. It is selected from Dazin and Etoxazole.
[0143] (11) A microbial disruptor of the insect gut membrane, Bacillus thuringiensis Bacillus thuringiensis subsp. ecies israelensis), Bacillus sphaericus sphaericus), Bacillus thuringiensis subsp. aizawai (Baci Illus thuringiensis subspecies aizawai), Bacillus thuringiensis subsp. kurstaki (Bacillus thuringiensis nsis subspecies kurstaki), Bacillus thuringiensis subspecies tenebrionis (Bacillus thuringiensis subspecies cies tenebrionis) and Bt plant proteins (which include Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCr y3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1 ) is selected.
[0144] (12) Inhibitors of mitochondrial ATP synthase, preferably an ATP disruptor, which is selected from diafenthiuron; or Organotin compounds, which consist of azocyclotin, cyhexatin and fenbutatin oxide selected; or Propargite; or tetradifon.
[0145] (13) Uncouplers of oxidative phosphorylation by disrupting the proton gradient, which It is selected from lorfenapir, DNOC and sulfluramide.
[0146] (14) Nicotinic acetylcholine receptor channel blockers, which include bensultat cartap, cartap hydrochloride, thiocylam and thiosultap sodium The compound is selected from the group consisting of ammonium, ammonium hydroxide, ammonium nitrate ...
[0147] (15) Chitin biosynthesis inhibitors (type 0), such as bistrifluron and chlorflurane. Luazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflu Muron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflum is selected from
[0148] (16) Chitin biosynthesis inhibitors (type 1), which are selected from buprofezin do.
[0149] (17) Molting disruptors (especially for Diptera, i.e., For dipterans), this is selected from cyromazine.
[0150] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, and metoprolol. It is selected from toxifenozide and tebufenozide.
[0151] (19) Octopamine receptor agonists, which are selected from amitraz.
[0152] (20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnon, It is selected from acequinocyl and fluacrypyrim.
[0153] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides, which include fenazaquin, fenpyroximate, pyrimidifen, selected from pyridaben, tebufenpyrad and tolfenpyrad; or Rotenone (Derris).
[0154] (22) Voltage-dependent sodium channel blockers, such as indoxacarb and metoprolol It is selected from taflumizone.
[0155] (23) Acetyl-CoA carboxylase inhibitors, preferably Tetronic acid derivatives and tetramic acid derivatives, such as spirodiclofen, spiromethicone, It is selected from phen and spirotetramat.
[0156] (24) Mitochondrial complex IV electron transport inhibitors, preferably Phosphine-based compounds, which include aluminum phosphide, calcium phosphide, phosphine, and phosphorus zinc oxide; or Cyanides, including calcium cyanide, potassium cyanide, and sodium cyanide is selected from.
[0157] (25) Mitochondrial complex II electron transport inhibitors, preferably β-ketonitrile derivatives, which are selected from cyenopyrafen and cyflumetofen. and Carboxanilides, which are selected from piflubumid.
[0158] (28) Ryanodine receptor modulators, preferably Diamides, including chlorantraniliprole, cyantraniliprole, and fulve The diamides are selected from the group consisting of phenylalanine, ...
[0159] (29) Chordotonal organ modulators (target sites undefined), which are The compound is selected from the group consisting of amides.
[0160] (30) An additional active ingredient selected from the following: acinonapir, afidopiro Pen, Afoxolaner, Azadirachtin, Benclotiaz, Benzoximate, Ben Zpirimoxan, bifenazate, broflanilide, bromopropylate, chinomethionine phosphate, chloroprallethrin, cryolite lite), cyclaniliprole, cycloxapride, cyhalodiamide (cyhalod iamide), dichloromezothiaz, dicofol, ε-metofluthrin, ε-momfluthrin Phosphorus (epsilon-momfluthrin), flometoquin, fluazaindrizi fluensulfone, flufenerim, flufenoxystrobin, flufiprole , fluhexafon, fluopyram, flupirimine, fluralaner, fluxametamide, Fenozide, guadipyr, heptafluthrin, imidacloth, iprodione, κ-bifu entrin, kappa-tefluthrin, lotilaner, meperfluthrin, oxazosulfil, Paichongding, pyridalyl, pyrifluquinazone, Riminostrobin, spirobudiclofen, spiro Pigeon, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole tigolaner, thioxazaphen, thiofluoximate ( thiofluoximate), triflumezopyrim, and iodomethane; , a preparation based on Bacillus firmus (I-15 82, BioNeem, Votivo), and further the following compounds: 1-{2 -fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl] {phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), {1' -[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluoro Rospiro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyri (Zin-4-yl)methanone (known from WO2003 / 106457) (CAS 6373 60-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl) yl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl )phenyl]isonicotinamide (known from WO2006 / 003494) (CAS 8 72999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydro Oxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (WO Known from 2010052161) (CAS 1225292-17-0), 3- (4- (2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro [4.5] Dec-3-en-4-yl ethyl carbonate (previously available from EP 2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy) -6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (WO20 Known from 04 / 099160) (CAS 792914-58-0), PF1364 (J Known from P2010 / 018586) (CAS 1204776-60-2), (3E) -3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1, 1-Trifluoro-propan-2-one (known from WO2013 / 144213) (CA S 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl] [phenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)- 1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CA S 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl ethyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyridine Zole-3-carboxamide (known from CN103232431) (CAS 14492 20-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5- (trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo 4-[5-(3,5-dichlorophenyl)-4, 5-Dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N -(trans-1-oxido-3-thietanyl)benzamide and 4-[(5S)-5- (3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3- Isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benz Amide (known from WO2013 / 050317A1) (CAS 1332628-83- 7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N -Ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide , (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl] -N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanol Imidazole and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4- -N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propionate Panamide (WO2013 / 162715A2, WO2013 / 162716A2, US Known from 2014 / 0213448A1) (CAS 1477923-37-7), 5- [[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro -4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl
[0023] -1H-pyrazole-3-carbonitrile (known from CN101337937A) CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6 -[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl )-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan , known from CN103109816A) (CAS 1232543-85-9); N-[ 4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methyl [phenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyridinyl CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazole- 2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2- pyridinyl)-1H-pyrazole-5-carboxamide (WO2011 / 085575A 1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro- 4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy ]-2-Methoxy-6-(trifluoromethyl)pyrimidine (CN101337940A (2E)- and 2(Z)-2-[2 -(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene] -N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (CN101 Known from 715774A) (CAS 1232543-85-9); 3-(2,2-dichloro- 2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl Nyl-cyclopropanecarboxylic acid ester (known from CN103524422A) (CA S 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[ [(Methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino] [carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carbohydrate Methyl carboxylic acid ester (known from CN102391261A) (CAS 1370358 -69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-,1-[N- [4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H -1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopeptide Lanose (known from US2014 / 0275503A1) (CAS 1181213-1 4-8);8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy) -3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3. 2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2- Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl)phenoxy (C)-3-(2-methyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane AS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy- 4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazine- 3-yl)-3-aza-bicyclo[3.2.1]octane (WO2007040280A 1, known from WO2007040282A1) (CAS 934001-66-8), N -[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl -3-[(3,3,3-trifluoropropyl)thio]-propanamide (WO2015 / 058021A1, known from WO2015 / 058028A1) (CAS 14779 19-27-9), and N-[4-(aminothioxomethyl)-2-methyl-6-[( Methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl (I)-1H-pyrazole-5-carboxamide (known from CN103265527A) CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[ [4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (WO2013 / 11 5391A1) (CAS 1449021-97-9), 3-(4-chloro-2 ,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5 ] decane-2,4-dione (known from WO2014 / 187846A1) (CAS 16 38765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy Di-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carboxylic acid ethyl ester (WO2010 / 066780A1, WO2011151 146A1) (CAS 1229023-00-0), 4-[(5S)-5-( 3,5-Dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl) N-[(4R)-2-ethyl-3-oxo-4-isoxazolyl]-N-[(4R)-2-ethyl-3-oxo-4-isoxazolyl]- oxazolidinyl]-2-methyl-benzamide (WO2011 / 067272, WO2 Known from 013 / 050302) (CAS 1309959-62-3).
[0161] disinfectant Active ingredients identified herein by "common name" are known and For example, see "The Pesticide Manual (16th Ed.Bri or listed in the National Crop Protection Council (Nat. Or you can search the internet (e.g. "www.alanwood. net / pesticides").
[0162] All biocidal mixtures named in classes (1) to (15) are If the functional groups allow it, it may also be possible to form salts with suitable bases or acids. All mixing partners named in classes (1) to (15) are to be used where appropriate. may include tautomeric forms.
[0163] (1) Inhibitors of ergosterol biosynthesis, e.g., (1.001) cyproconazole , (1.002) Difenoconazole, (1.003) Epoxiconazole, (1.00 4) Fenhexamid, (1.005) Fenpropidin, (1.006) Fenpropid Morph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1. 009) Flutriafol, (1.010) Imazalil, (1.011) Imazalil sulfate , (1.012) Ipconazole, (1.013) Metconazole, (1.014) Miconazole Ibutanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1. 017) Propiconazole, (1.018) Prothioconazole, (1.019) Pyriso Xazol, (1.020) Spiroxamine, (1.021) Tebuconazole, (1.0 22) Tetraconazole, (1.023) Triadimenol, (1.024) Tridemol F, (1.025) Triticonazole, (1.026) (1R,2S,5S)-5-(4 -chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-trimethylbenzyl) (1S,2R,5R)triazol-1-ylmethyl)cyclopentanol, (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 pyryl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1 .029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichloro Chlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butane- 2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(thiazolinone] [1H-1,2,4-trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl) Propan-2-ol, (1.031)(2S)-2-(1-chlorocyclopropyl)-4 -[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazo (1.032)(2S)-2-(1-chlorocyclohexane)-1-ylbutan-2-ol (1H-1,2-dichloropropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1, 2,4-triazol-1-yl)butan-2-ol, (1.033)(2S)-2- [4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H -1,2,4-triazol-1-yl)propan-2-ol, (1.034)(R -[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl) -1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035 )(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl) (phenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1 .036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl) (phenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1 .037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy) phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2, 4-Triazole, (1.038)1-({(2S,4S)-2-[2-chloro-4-( 4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl (1.039)1-{[3-(2-chlorophenyl)-1H-1,2,4-triazole (phenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H -1,2,4-triazol-5-yl thiocyanate, (1.040)1-{[rel (2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)o Xylan-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate ester, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2 -(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4 -triazol-5-yl thiocyanate, (1.042)2-[(2R,4R,5R) -1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhepta benzo-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, ( 1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxybenzoate Hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1 ,2,4-triazole-3-thione, (1.044)2-[(2R,4S,5R)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane- 4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1. 045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydro [2,4-dihydro-3H-1,2-xy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro- ,4-triazole-3-thione, (1.046)2-[(2S,4R,5R)-1-( 2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane-4- yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.04 7) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy -2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4 -triazole-3-thione, (1.048)2-[(2S,4S,5R)-1-(2, 4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl ]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2 ,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-trimethylheptan-4-yl Triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5 -Hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H -1,2,4-triazole-3-thione, (1.051)2-[2-chloro-4-(2 ,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazole-1- (1.052) 2-[2-chloro-4-(4-chlorophenoxy)-2-yl]propan-2-ol [1H-1,2,4-triazol-1-yl]butane-2- ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl [1H-1,2,4-triazol-1-yl]phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl) Phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol , (1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl) fluoride [phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl) (I)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazo 2-[[rel(2R,3R)-3-(2-chlorophenyl)-3-thione, (1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-3-thione, (phenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2, 4-Dihydro-3H-1,2,4-triazole-3-thione, (1.058)2-{[ rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) (I)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazo 4-chlorobenzyl-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl) -2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopenta (1.060) 5-(arylsulfanyl)-1-{[3-(2-chlorophenyl) (2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1 ,2,4-triazole, (1.061)5-(arylsulfanyl)-1-{[rel (2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)o Xylan-2-yl]methyl}-1H-1,2,4-triazole, (1.062)5- (arylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl) -2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2 ,4-triazole, (1.063)N'-(2,5-dimethyl-4-{[3-(1,1 ,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl -N-methylimidoformamide, (1.064)N'-(2,5-dimethyl-4-{[ 3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N- Ethyl-N-methylimidoformamide, (1.065)N'-(2,5-dimethyl-4 -{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl} (phenyl)-N-ethyl-N-methylimidoformamide, (1.066)N'-(2,5 -Dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl (1.067)N'-(2,5-diphenyl)-N-ethyl-N-methylimidoformamide Methyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenone (1.068)N'- (2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl] {phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl) sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070)N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfonyl] (phenyl)phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1 .071)N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl Thilimidoformamide, (1.072)N'-(4-{[3-(difluoromethoxy) Phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimide N'-(4-[(difluoromethyl)sulfanilide, (1.073) {phenyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoform Amide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-indene -2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimide Formamide, (1.075)N'-{4-[(4,5-dichloro-1,3-thiazole -2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidophos Fluoramide, (1.076)N'-{5-bromo-6-[(1R)-1-(3,5-difluoromethyl)- (fluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyl Imidoformamide, (1.077)N'-{5-bromo-6-[(1S)-1-(3 ,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl -N-methylimidoformamide, (1.078)N'-{5-bromo-6-[(cis- 4-Isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethoxy N-methylimidoformamide, (1.079)N'-{5-bromo-6-[(trimethylsilyl) trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.080)N'-{5-bromo-6 - [1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}- N-Ethyl-N-methylimidoformamide, (1.081) Mefentrifluconazole Mefentrifluconazole, (1.082) Ifentrifluconazole Nazole (ipfentrifluconazole).
[0164] (2) Inhibitors of the respiratory chain at complex I or complex II, e.g., (2.001)beta Nzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2. 004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, ( 2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isoflurane etamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4 S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R,9R), (2.012) isopyrazam (anti-epimer racemic compound 1RS ,4SR,9SR), (2.013) isopyrazam (syn-epimer racemic compound (1 RS, 4SR, 9RS) and the anti-epimer racemic compound (1RS, 4SR, 9SR) (2.014) Isopyrazam (syn-epimeric enantiomers 1R,4 S,9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S,4 R,9S), (2.016) isopyrazam (syn-epimer racemic compound 1RS,4 SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2 .019) Pydiflumetofen, (2.020) Pyraziflumid, (2.021) Sedaki San, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro dro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.0 23) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro -1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024 )1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025)1 -methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl [2-fluoro-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro -6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1 -methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl) (2.028) 3-(difluoromethyl)-1H-pyrazole-4-carboxamide )-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H- Inden-4-yl]-1H-pyrazole-4-carboxamide, (2.029) 3-( (3S)-1,1,3-trimethyl-2,3-difluoromethyl Dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2 .030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl- 2,3-Dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4- Carboxamide, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro Oro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1- Methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl (3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2 .033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoro (trimethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylate Ruboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N -Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyra 2.036) N-(2-tert-butylbenzyl)- N-Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pi 4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl )-N-Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H -pyrazole-4-carboxamide, (2.038)N-(5-chloro-2-isopropyl (Difluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl thyl-1H-pyrazole-4-carboxamide, (2.039)N-[(1R,4S)- 9-(Dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene -5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbo oxamide, (2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2, 3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl (2.041)N-[1-methyl-1H-pyrazole-4-carboxamide (2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoro Methyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042)N-[ 2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)benzyl (fluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl ]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H -pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl) [N-cyclopropyl-3-(difluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro 1-methyl-1H-pyrazole-4-carboxamide, (2.045)N-cyclopropanediol propyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2 -(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2. 046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoromethyl)- (fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide N-cyclopropyl-3-(difluoromethyl)-5-fluoro- N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4- Carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5- Fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxylate Rubothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5- Fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxylate Ruboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro Fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazo N-cyclopropyl-3-(difluoromethyl)-4-carboxamide, (2.051) (2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1 H-Pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl) (fluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl N-cyclopropyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3- (Difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1- Methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl- N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5- Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055)N- Chloropropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl) (2.0)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide 56) N-Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl) (ethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.
[0165] (3) Inhibitors of the respiratory chain at complex III, for example (3.001) Ametoctra Gin, (3.002) Amisulbrom, (3.003) Azoxystrobin, (3.00 4) Coumethoxystrobin, (3.005) Moxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin , (3.008) Enoxastrobin, (3.009) Famoxadone, (3.010) Fenamidon, (3.011) Flufenoxystrobin obin), (3.012) Fluoxastrobin, (3.013) Kresoxime-methionine Le, (3.014) metominostrobin, (3.015) orysastrobin, (3.01 6) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyramet Strobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin Bin, (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)- 1-Fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy) methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022 )(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl ]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3 .023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl} -2-Methoxy-N-methylacetamide, (3.024)(2S)-2-{2-[(2 ,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetami (3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[( (isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino ]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropionate Panoate, (3.026) 2-{2-[(2,5-dimethylphenoxy)methyl]phen N-(3-ethyl-2-methyl-N-methylacetamide), (3.027) N-(3-ethyl-3 ,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide (3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl )-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethyl Lupent-3-enamide, (3.029) {5-[3-(2,4-dimethylphenyl) -1H-pyrazol-1-yl]-2-methylbenzyl}carbamate methyl.
[0166] (4) Mitosis and cell division inhibitors, for example, (4.001) carbendazim, ( 4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluo Picolide, (4.005) Pencycuron, (4.006) Thiabendazole, (4.00 7) Thiophanate-methyl, (4.008) Zoxamide, (4.009) 3-chloro- 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.0 10) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridine-3- yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.0 12) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl) )-1,3-dimethyl-1H-pyrazol-5-amine, (4.013)4-(2-bromo (2-bromo-6-fluorophenyl)-N-(2-bromo-4-fluorophenyl)-1,3-di Methyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluoro (2-bromophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5 -amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro (4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, .016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)- 1,3-Dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo- (4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pi 4-(2-chloro-4-fluorophenyl)-N-thiazol-5-amine, (4.018) -(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine , (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6- Fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020 )4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3- Dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluoro (2-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole -5-Amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluoro phenyl)-3,6-dimethylpyridazine, (4.023)N-(2-bromo-6-fluoro (2-chloro-4-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H -pyrazol-5-amine, (4.024)N-(2-bromophenyl)-4-(2-chlorophenyl)- (4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4 -fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.
[0167] (5) Compounds capable of acting at multiple sites, e.g., (5.001) Bordeaux mixture, (5. 002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, ( 5.005) Copper hydroxide, (5.006) Copper naphthenate, (5.007) Copper oxide, (5.0 08) Basic copper chloride, (5.009) Copper(2+) sulfate, (5.010) Dithianon, (5 .011) Dodine, (5.012) Folpet, (5.013) Mancozeb, (5.014 ) Maneb, (5.015) Metiram, (5.016) Metiram zinc (metiram zinc), (5.017) copper oxine, (5.018) propineb, (5.019) sulfur Yellow and sulfur agents, for example, calcium polysulfide, (5.020) thiuram, (5.021) di Neb, (5.022) Ziram, (5.023) 6-ethyl-5,7-dioxo-6,7- Dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1 ,2]Thiazole-3-carbonitrile.
[0168] (6) Compounds capable of inducing host defenses, e.g., (6.001) acibenzolar-S -methyl, (6.002) isotianil, (6.003) probenazole, (6.004 )Tiadinil.
[0169] (7) Inhibitors of amino acid and / or protein biosynthesis, e.g., (7.001) cysteine Prodinil, (7.002) Kasugamycin, (7.003) Kasugamycin Hydrochloride Hydrate substance, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.00 6) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinone (1-phenyl)quinoline.
[0170] (8) Inhibitors of ATP production, for example, (8.001) silthiofam.
[0171] (9) Inhibitors of cell wall synthesis, for example, (9.001) benthiavalicarb, (9.0 02) Dimethomorph, (9.003) Flumorph, (9.004) Iprovalicarb, ( 9.005) Mandipropamid, (9.006) Pyrimorph, ( 9.007) Valifenalate, (9.008) (2E)-3-(4-tert-butyl (phenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)propionate L-2-en-1-one, (9.009)(2Z)-3-(4-tert-butylphenyl) (2-chloropyridin-4-yl)-1-(morpholin-4-yl)propan- -2-en-1-on.
[0172] (10) Inhibitors of lipid and membrane synthesis, for example, (10.001) propamocarb, ( 10.002) Propamocarb hydrochloride, (10.003) Tolclofos-methyl.
[0173] (11) Inhibitors of melanin biosynthesis, for example, (11.001) tricyclazole, ( 11.002) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl) (zoyl)amino]butan-2-yl}carbamate.
[0174] (12) Inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.00 2) Benalaxyl-M (chiralaxyl), (12.003) Metalaxyl, (12.00 4) Metalaxyl-M (mefenoxam).
[0175] (13) Signal transduction inhibitors, for example, (13.001) fludioxonil, (1 3.002) Iprodione, (13.003) Procymidone, (13.004) Proquina Zide, (13.005) quinoxyfen, (13.006) vinclozolin.
[0176] (14) Compounds that can act as uncouplers, e.g., (14.001) fluazinam , (14.002) Meptylzinocap.
[0177] (15) Further compounds, for example (15.001) abscisic acid, (15.002 ) Benthazole, (15.003) Bethoxadin, (15.004) Capsimycin ( capsimycin), (15.005) carvone, (15.006) chinomethionine thiamin, (15.007) khuraneb, (15.008) cyflufenamid, (15.009 ) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil , (15.012) fosetyl-aluminum, (15.013) fosetyl-calcium, (15.014) Fosetyl sodium, (15.015) Methyl isothiocyanate, ( 15.016) Metrafenone, (15.017) Mildiomycin, (15.018) ) Natamycin, (15.019) Nickel dimethyldithiocarbamate, (15.02 0) Nitroisopropyl nitrite, (15.021) Oxamocarb ), (15.022) oxathiapiproline, (15.023) oxyfenthiin (o xyfenthiin), (15.024) Pentachlorophenol and salts, (15.0 25) Phosphorous acid and its salts, (15.026) Propamocarb-fosetylate (prop amocarb-fosetylate), (15.027) pyriophenone (Kurazaf chlazafenone), (15.028) tebufloquine, (15.02 9) Tecloftalam, (15.030) Tornifanide, (15.031) 1-(4-{ 4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-o thiazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2 -[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone , (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H- pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridine-2- 1H,5H-[1,4]dithiyl)quinazoline, (15.034) 2,6-dimethyl-1H,5H-[1,4]dithiyl No[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone , (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazole-1- yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl ]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazole-2- yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl) (4-{5-[2-chloro- 6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-o {1,3-thiazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanoate Non, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazole- 1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yl (phenyl)-4,5-dihydro-1,2-oxazol-3-yl}-1,3 -thiazol-2-yl)piperidin-1-yl]ethanone, (15.038)2-[6 -(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolidinyl (15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoro) Methyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3- Thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3- Chlorophenyl methanesulfonate, (15.040)2-{(5S)-3-[2-( 1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl} Piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2 -oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.04 1) 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6 -fluorophenyl}propan-2-ol, (15.042) 2-{2-fluoro-6 -[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propane-2 -ol, (15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl (1H-pyrazol-1-yl)acetyl}piperidin-4-yl)-1,3-thia 4,5-dihydro-1,2-oxazol-5-yl}-3-chloro phenyl methanesulfonate, (15.044)2-{3-[2-(1-{[3,5 -bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidine-4 -yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazole -5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4 -dihydroisoquinolin-1-yl)quinoline, (15.047)3-(4,4-difluoroisoquinolin-1-yl)quinoline, Oro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15 .048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino 4-oxo-4- [(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4 -Thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N' -(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide, (15.05 2) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-Fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4 -amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl) (15.055) buta-3-yl)-2,3-dihydro-1,4-benzoxazepine, 1-methyl-1H-tetrazol-5-yl(6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)( phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, ( 15.056) Ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, ( 15.057) Phenazine-1-carboxylic acid, (15.058) 3,4,5-trihydro Propyl hydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinoline Phosphorus-8-ol sulfate (2:1), (15.061){6-[({[(1-methyl (phenyl)methylene]amino}oxy)methyl] tert-Butyl pyridin-2-yl}carbamate, (15.062) 5-fluoro- 4-Imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydriodide lopyrimidin-2(1H)-one.
[0178] Biological pesticides as mixture components The compounds of formula (I) may be combined with a biological pesticide.
[0179] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and microbial pesticides. The term "enzyme" includes products (e.g., proteins and secondary metabolites) formed by the enzyme.
[0180] Biological pesticides include bacteria, e.g., spore-forming bacteria, root-colonizing bacteria, and These include bacteria that act as pesticides, fungicides or nematicides, and bacteria that act as biological insecticides, fungicides or nematicides.
[0181] The above-mentioned bacteria are used or can be used as biological pesticides. An example is the following: Bacillus amyloliquefaciens iens strain FZB42 (DSM 231179) or Bacillus cereus (Bac Bacillus cereus), especially B. cereus strain CN CM I-1562, or Bacillus firmus strain I-1582 (accession number CNCM I-1582), or Bacillus pumilus (B Acillus pumilus), in particular strain GB34 (accession number ATCC 7008 14) and strain QST2808 (accession number NRRL B-30087), or Bacillus Bacillus subtilis, in particular strain GB03 (accession number ATCC SD-1397) or Bacillus subtilis tilis strain QST713 (accession number NRRL B-21661), or Bacillus Bacillus subtilis strain OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis (Bacillus thuringiensis uringiensis), especially Bacillus thuringiensis subsp. israerensis B. thuringiensis subspecies israelensi s) (antigenic type H-14) strain AM65-52 (accession number ATCC 1276), or Bacillus thuringiensis subspecies Aizawai (B. thuringiensis subsp. aizawai), in particular strain ABTS-1857 (SD-1372), Bacillus thuringiensis subsp. kurstaki (B. thuringiensis s subsp. kurstaki) strain HD-1, or Bacillus thuringiensis Subspecies tenebrionis (B. thuringiensis subsp. tene brionis strain NB 176 (SD-5428), Pasteuria penetrans (P asteuria penetrans), Pasteuria species (Pasteuria s pp.) (Rotylenchulus reniformis (Rotylenchulus reniformis rmis)-PR3 (accession number ATCC SD-5834), Streptomyces Streptomyces microflavus strain AQ612 1 (= QRD 31.013, NRRL B-50550), Streptomyces galli Streptomyces galbus strain AQ 6047 (accession number NRR L 30232).
[0182] Fungi and yeasts that are or can be used as biological pesticides Examples of classes are: Beauveria bassiana, specifically strain ATCC 74040, Coniothyrium minitans (Coniothyrium minita ns), in particular, strain CON / M / 91-8 (accession number DSM-9660), Lecanisiriu Lecanicillium spp., in particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Known as Verticillium lecanii In particular, strain KV01, Metarhizium anisopliae (Metarhizium anisopliae), in particular strain F52 (DSM3884 / ATCC 90448) , Metschnikowia fructico la), in particular, strain NRRL Y-30752, Paecilomyces fumosoroseus (Pae cilomyces fumosoroseus) (Current: Isaria fumosorosea (I saria fumosorosea), in particular the strain IFPC 200613 or the strain Ap opka 97 (accession number ATCC 20874), Paecilomyces lilacinus (P aecilomyces lilacinus), especially Paecilomyces lilacinus ( P. lilacinus) strain 251 (AGAL 89 / 030550), Talaromyces Talaromyces flavus, especially strain V117b, Trichoderma Trichoderma atroviride, especially strain SC 1 (Accession number CBS 122089), Trichoderma harzianum (Trichod erma harzianum), especially Trichoderma harzianum riffai (T. harzianum rifai)T39 (accession number CNCM I-952).
[0183] Viruses that are or can be used as biological pesticides An example is the following: Smaller apple tortrix (Adoxophyes orana) granulosis virus (GV) , codling moth (Cydia pomonella) granulosis virus (GV), tobacco Helicoverpa armigera nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera exigua (Spodoptera frugiperda)mNPV, Egyptian armyworm (Afri) can cotton leafworm)(Spodoptera littoral is) NPV.
[0184] added as an "inoculum" to a plant or plant part or plant organ, Bacteria and fungi that promote plant growth and plant health through certain properties are also included. Examples that can be given are: Agrobacterium spp., Azorhizobium Azorhizobium caulinodans, Azospirill Azospirillum spp., Azotobacter spp. cter spp.), Bradyrhizobium spp. .), Burkholderia spp., especially Burkholderia Burkholderia cepacia (formerly known as Pseudomonas cepacia) Monas cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum (Gi gaspora monosporum), Glomus spp., Laccaria spp., Lactobacillus buchneri obacillus buchneri, Paraglomus species spp.), Pisolithus tinctorus , Pseudomonas spp., Rhizobium spp. zobium spp.), especially Rhizobium trifolii (Rhizobium tr ifolii), Rhizopogon spp., Scleroderma Scleroderma spp., Suillus spp. ), Streptomyces spp.
[0185] Plant extracts that are or can be used as biological pesticides and products formed by microorganisms (which include proteins and secondary metabolites) ) is the following: Garlic (Allium sativum), Wormwood (Artemisia absinthium) inthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus Celastrus angulatus, American antler plant (C henopodium anthelminticum), chitin, Armour-Ze n, Dryopteris filix-mas, Horsetail (Equi setum arvense), Fortune Aza, Fungastop, Hea ds Up (Quinopodium quinoa saponin extract), insect repellent Chrysanthemum (Pyrethrum / Pyrethrins), Surinam bittersweet (Quassia amara), Quercus, Quillaja, Rega lia, ("Requiem TM Insecticide), rotenone, riania / Ryanodine, Symphytum officinale, Artemisia (Tanacetum vulgare), Thymol, Triact 70, TriCo n, nasturtium (Tropaeulum majus), nettle (Urtic a dioica), Veratrin, European mistletoe (Viscum album ), Brassicaceae extracts, especially rapeseed flour or mustard flour End.
[0186] Safeners as blend components The compounds of formula (I) can be used as safeners, e.g., benoxacor, cloquintocet, (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlor (-ethyl), fenclorim, flurazole, fluxofenim, furilazole , Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Xabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl (phenyl)sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroaza Cetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07- 3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine ( It can be combined with other compounds such as CAS 52836-31-4.
[0187] Plants and plant parts All plants and plant parts can be treated according to the invention, where the plants are desirable and undesirable wild or crop plants (including naturally occurring crop plants) All plants and plant parts such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar Squid, tomato, pepper, cucumber, melon, carrot, watermelon, onion, lettuce, Spinach, leeks, kidney beans, Brassica oleracea) (e.g., cabbage) and other vegetable species, cotton, tobacco, rapeseed, etc. and, in addition, fruit plants (fruit-bearing plants, apples, pears, citrus fruits and grapevines). ) etc. Crop plants are those obtained by conventional breeding and optimization methods. The plant may be a plant capable of producing the desired product or may be obtained by biotechnological and genetic engineering methods. or a plant obtainable by a combination of the above methods. Such crop plants also include transgenic plants, It also includes plant varieties that may or may not be protected by variety ownership rights. Plants include all stages of development, such as seeds, seedlings, and young plants (immature plants). The term should be understood to mean the mature plant. Plant parts include shoots, leaves, flowers, etc. is understood to mean all parts and organs of the plant, both above-ground and below-ground, such as the roots and Examples that may be mentioned include leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds, as well as and further including tubers, roots and rhizomes. Harvested plants or harvested plant parts, and vegetative propagation organs al) and reproductive organs (generative propagation mater ial), such as seedlings, tubers, rhizomes, cuttings and seeds, also include plant parts. is included in the part.
[0188] The treatment according to the invention of plants and plant parts with compounds of formula (I) can be carried out in the conventional manner. By various treatment methods, for example, immersion, spraying, vaporization, fogging, scattering, The compounds may be applied directly to the plant or plant parts by application, injection, etc., or by injecting the compounds into the surrounding area of the plant or plant parts. , by acting on the environment or storage space, Also, in the case of propagation material, especially seeds, may also be achieved by applying one or more coatings.
[0189] As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or hybrids or progeny, can be used. Plant species and plant cultivars obtained by conventional biological breeding methods such as rotoplast fusion, In yet another preferred embodiment, the portions are further processed. Transgenics obtained by genetic engineering methods, sometimes in combination with conventional methods. Plants and plant cultivars (genetically modified organisms) and their parts are treated. rts) or "parts of plants" or "parts of plants" The invention is particularly preferably are treated with plants of conventional varieties that are commercially available or in use, respectively. Plant varieties are developed by conventional breeding or by mutagenesis or recombinant DNA techniques. is understood to mean a plant with new properties ("traits") obtained by artifical means. They can be cultivars, varieties, biotypes or genotypes.
[0190] Transgenic plants, seed treatments and integration events events) Receiving genetic material through genetic modification that confers particularly advantageous and beneficial characteristics ("traits") to a plant All plants collected are transgenic or vegetative plants which are preferably treated according to the invention. Examples of such traits are plant varieties (obtained by genetic engineering). Improved growth of plants, improved tolerance to high or low temperatures, drought or in water or soil Improved tolerance to salinity levels, increased flowering ability, improved ease of harvesting Enhanced maturity, increased yield, improved quality and / or quality of the harvested product such as increased nutritional value, improved shelf life and / or improved processability of the harvested product. Yet another particularly important example of such a property is the ability to inhibit pests and harmful microorganisms (e.g., insects). Plant enhancement against insects (e.g., spiders, arachnids, nematodes, mites, slugs and snails) resistance, e.g., to toxins formed in the plant, especially Bacillus thuringiensis Genetic material derived from Bacillus thuringiensis, e.g. Genes CryIA(a), CryIA(b), CryIA(c), CryIIA, Cry IIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and combinations thereof] toxins formed in plants, causing pests and harmful microorganisms (e.g. insects, arachnids, nematodes, mites, slugs and snails) Improved resistance of plants to plant pathogenic fungi, bacteria and / or viruses. Improved plant resistance to, e.g., systemic acquired resistance (SAR), systemin (sys temin), phytoalexins, inducers, and further resistance genes and their expression against plant pathogenic fungi, bacteria and / or viruses by proteins and toxins produced by and, furthermore, the improved resistance of plants to certain herbicidally active compounds (e.g., imidazoline). Plant Improvement to Non-Glycerol, Sulfonylurea, Glyphosate, or Phosphinothricin The gene that confers the desired trait is a resistance to the genotype (e.g., the "PAT" gene). They may also be present in combination with one another in a transgenic plant. Examples of transgenic plants that can be produced include important crop plants, such as cereals (wheat, , rice, triticale, barley, rye, oats), corn, soybean, potato Potatoes, sugar beets, sugarcane, tomatoes, peas and other types of vegetables, cotton, tobacco , rapeseed, and further, fruit plants (those bearing fruit, apples, pears, citrus fruits and Examples include corn, soybeans, wheat, rice, and potatoes. , cotton, sugarcane, tobacco and rapeseed are of particular importance. Traits of particular importance are insects, Improved resistance of plants to arachnids, nematodes, and slugs and snails is.
[0191] Crop protection - types of treatment The treatment of plants and plant parts with compounds of formula (I) can be carried out in the same manner as conventional treatment methods. For example, by immersion, spraying, atomizing, irrigating, vaporizing, dusting, fogging, scattering, foaming, painting, etc. , spreading-on, injection, irrigation (drenching), point The compounds may be applied directly to the plants, such as by drip irrigation, or by applying the compounds to the surrounding areas of the plants and plant parts. , habitat or storage space, and also by injecting the reproductive organs (pro In the case of pesticides, especially seeds, dry seed treatment is also required. as a powder for seed treatment, a solution for liquid seed treatment, a water-soluble powder for slurry treatment, and as a coating. Furthermore, the compound represented by formula (I) may be treated by coating with one or more films. The compound is applied by ultra-low volume method. Alternatively, the application form or the compound represented by formula (I) itself may be applied to the soil. It is also possible to inject it into
[0192] A preferred direct treatment of plants is by foliar application (i.e., application of a compound of formula (I) to the foliage). In this case, the frequency of treatment and the amount of application shall be determined according to the level of occurrence of the pest. should be adapted according to the rules.
[0193] In the case of systemically active compounds, the compounds of formula (I) can also be transported via the root system. In this case, the plant will reach the plant even if the plant is exposed to the compound of formula (I) in relation to its habitat. This is done by applying a compound that has a specific function, for example, by irrigation. g) or by mixing into the soil or nutrient solution (i.e., in the place where the plants grow ( impregnating a liquid form of a compound of formula (I) into a soil or a hydroponic system, for example; or by soil application [i.e., by administering the compound of formula (I) according to the invention in solid form by applying the agent to the locus of the plants (for example in granular form) or by drip application ( Often referred to as "chemigation" (i.e., plant At a defined position in the vicinity of the compound of formula (I) according to the present invention, a compound of formula (I) containing varying amounts of water is added. Together, liquid applications over a specific period of time from the surface or underground drip line. In the case of rice crops, this can be achieved by applying the fertilizer in a solid form. A compound of formula (I) (e.g., as a granule) is metered into a flooded rice paddy. It can also be implemented by
[0194] Seed treatment Control of pests by treating plant seeds has been known for a long time and is continually being improved. However, seed treatment has not always been satisfactorily resolved. Thus, during storage of the plants, after sowing or Eliminate or at least significantly reduce the need for additional post-emergence pesticide applications. It is desirable to develop methods for protecting seeds and germinating plants so that The active compounds used protect the plant from pest attacks without causing any damage to the plant itself. Optimize the amount of active compound used to ensure optimal protection of seeds and germinating plants In particular, seed treatment methods that use minimal amounts of pesticide to treat the seeds are also desirable. In order to achieve optimal protection of the plants and also of the germinating plants, Intrinsic insecticidal properties of insect-resistant or pest-tolerant transgenic plants Sexual or nematicidal properties should also be taken into consideration.
[0195] The present invention therefore relates in particular to a method for protecting seeds and germinating plants from attack by pests. The method also relates to a method for treating seeds with one of the compounds of formula (I): The method of the present invention for protecting seeds and germinating plants from attack by pests The method further comprises treating the seeds with a compound of formula (I) and a mixture of ingredients in one operation. The method also includes treating the seeds simultaneously or sequentially. It also includes a method in which the compound represented by I) and the mixed component are treated at different times. .
[0196] The present invention further provides a method for protecting seeds and the resulting plants from pests. It also relates to the use of a compound of formula (I) for treating children.
[0197] Furthermore, the present invention provides a compound of formula (I) according to the present invention, which is protected against pests. The present invention also relates to seeds treated with the compound. The present invention also relates to seeds treated simultaneously with the synthetic components. The present invention also relates to seeds treated at different times with the compound and the mixture components of formula (I). In the case of seeds treated at different times with different compounds and mixture components, the individual substances In this case, the compound of formula (I) may be present in a different layer on the surface of the polymer. The layers containing the components can optionally be separated by intermediate layers. Furthermore, the compound represented by formula (I) and the mixed component are used as a component of the coating or in addition to the coating. The present invention also relates to seeds to which the composition has been applied as a further layer or layers.
[0198] Furthermore, the present invention provides a method for reducing the abrasion of seeds by dust after treatment with a compound of formula (I). The present invention also relates to seeds that are subjected to a film coating process to prevent this.
[0199] One advantage of the systemically acting compounds of formula (I) is that they can be used to treat seeds. By treating the seeds, not only are the seeds themselves protected from pests, The fact is that the plants resulting from this treatment are also protected after emergence. This avoids the need to treat the crop directly shortly after sowing.
[0200] Treating seeds with a compound of formula (I) improves germination and The fact that sprouting may be enhanced should also be seen as a further advantage.
[0201] The use of the compounds of formula (I) is also particularly relevant to transgenic seeds. It is also considered advantageous that
[0202] Additionally, compounds of formula (I) may be used in combination with signal transduction techniques or compositions. It is also possible to use symbiotic organisms (e.g., rhizobia, mycorrhizal fungi and / or colonization by bacteria or endophytic bacteria or fungi) and / or nitrogen The immobilization is optimized.
[0203] The compounds of formula (I) are used in agriculture, in greenhouses, in forestry or in horticulture. It is particularly suitable for protecting the seeds of cereals (e.g. wheat, barley, rye, foxtail millet and oats), corn, cotton, soybean, rice , potato, sunflower, coffee, tobacco, canola, rapeseed, beet (e.g., lentils) and fodder beet), groundnut, vegetables (e.g., tomatoes, cucumbers, kidney beans ( beans), cruciferous vegetables, onions and lettuce, fruit plants, turf and ornamental seeds Cereals (e.g., wheat, barley, rye, and oats), corn, Treating the seeds of soybeans, cotton, canola, rapeseed, vegetables and rice is particularly important. do.
[0204] As already mentioned above, transgenic seeds with compounds of formula (I) The treatment of insecticides and / or nematicidal properties is also of particular importance. Plant seeds generally containing at least one heterologous gene that controls the expression of a peptide. These heterologous genes in the transgenic seeds are expressed in Bacillus s species, Rhizobium species, Pseudomonas s) species, Serratia species, Trichoderma species , Clavibacter species, Glomus species or Gli The present invention relates to the preparation of basil, which may be derived from a microorganism such as Gliocladium species. containing at least one heterologous gene derived from Bacillus sp. It is particularly suitable for treating transgenic seeds that are , derived from Bacillus thuringiensis It is a heterologous gene.
[0205] In the context of the present invention, the compounds of formula (I) are applied to the seeds. The seeds are treated in a state that is stable enough to avoid damage during treatment. The treatment can be carried out at any time between harvest and sowing. separated from the product and free of cobs, husks, petioles, husks, hairs or pulp, e.g. Seeds that have been harvested, purified, and dried to a moisture content that allows for storage Alternatively, after drying it can be treated with, for example, water and then dried again. In the case of rice seeds, rice embryos can be used. Use seeds that have been soaked, for example in water, until they reach a certain stage (pigeon breast stage). It is also possible to increase the concentration of the seeds, which stimulates germination and makes it more uniform.
[0206] When treating seeds, care should be taken to ensure that seed germination is not adversely affected or that the resulting plants are not damaged. The amount of compound of formula (I) applied to the seeds and / or further additives may be adjusted so as not to cause In general, care must be taken in selecting the amount of additive. This must be ensured, especially in the case of active compounds that may have phytotoxic effects at certain application rates. Not possible.
[0207] Generally, the compounds of formula (I) are applied to the seeds in a suitable formulation. Suitable formulations and methods for processing are known to those skilled in the art.
[0208] The compounds of formula (I) can be used in conventional seed dressing formulations, e.g. solutions, emulsions, and the like, such as a coating, suspension, powder, foam, slurry or other coating composition for seeds. It can be converted into a UV formulation and further converted into an ULV formulation.
[0209] These formulations can be prepared in known manner by incorporating the compounds of formula (I) in conventional excipients, e.g. , customary extenders, and further solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, Mixing with an antifoaming agent, a preservative, a second thickener, an adhesive, gibberellins, etc., and further Prepare by mixing with water.
[0210] Colors that may be present in seed dressing formulations that can be used in accordance with the present invention The coloring agents are all coloring agents customary for such purposes. Dyes that dissolve in pigments or water can be used. n B," "CI Pigment Red 112" and "CI Solvent Examples of colorants include those known as "Red 1."
[0211] Useful compounds that may be present in seed dressing formulations that can be used in accordance with the present invention include: Suitable wetting agents include all wetting-promoting agents customarily used in the formulation of pesticidal active compounds. Preferably, alkyl naphthalene sulfonates, such as diisopropyl Naphthalene sulfonate or diisobutyl naphthalene sulfonate, etc., are used.
[0212] Useful compounds that may be present in seed dressing formulations that can be used in accordance with the present invention include: Suitable dispersing and / or emulsifying agents are non-ionic surfactants customarily used in the formulation of pesticide active ingredients. All dispersants are of the ionic, anionic and cationic types. Preferably, they are nonionic or Anionic dispersants or mixtures of nonionic and anionic dispersants are used. The nonionic dispersants that are used are, in particular, ethylene oxide / propylene oxide bromine. polymers, alkylphenol polyglycol ethers and tristyrylphenols tristryrylphenol polyglycol ethers and their Suitable anionic dispersants include, in particular, the phosphorylated or sulfated derivatives of Lignosulfonates, polyacrylates and arylsulfonates / formaldehyde It is a condensation product.
[0213] Antifoaming agents that may be present in seed dressing formulations that may be used in accordance with the present invention The foam-inhibiting agents are all foam-inhibiting substances customarily used for the formulation of pesticide active ingredients. For example, silicone antifoaming agents and magnesium stearate are used.
[0214] Preservatives that may be present in seed dressing formulations that can be used in accordance with the present invention An agent is any substance that can be used for that purpose in an agrochemical composition. Examples include dichlorophene and benzyl alcohol hemiformal.
[0215] A second agent that may be present in a seed dressing formulation that may be used in accordance with the present invention. The thickening agents are all substances which can be used for this purpose in agrochemical compositions. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clay and finely divided silica are preferred. It's nice.
[0216] Adhesives that may be present in seed dressing formulations that can be used in accordance with the present invention The binders are all customary binders that can be used in seed dressing products. , polyvinyl acetate, polyvinyl alcohol and tylose are preferred. can be done.
[0217] Zybele spp. which may be present in seed dressing formulations which may be used in accordance with the present invention. The gibberellins are preferably gibberellin A1, gibberellin A3 (=gibberellic acid), gibberellin A4 (=gibberellic acid), gibberellin A5 (=gibberellic acid), gibberellin A6 (=gibberellic acid), gibberellin A7 (=gibberellic acid), gibberellin A8 (=gibberellic acid), gibberellin A Gibberellin A4 and gibberellin A7 are particularly preferred; gibberellic acid is particularly preferred. Phosphorus is known (cf. R. Wegler "Chemie der Pfl anzenschutz- and Schadlingsbekampfungsmi ttel”, vol.2, Springer Verlag, 1970, pp. 401-412).
[0218] Seed dressing formulations that can be used in accordance with the present invention are suitable for a wide variety of seed types. It can be used directly or after prior dilution with water to treat the It can be used, for example, as a concentrate or diluted with water. The preparations that can be obtained from concentrated formulations by the process are those derived from cereals, e.g. wheat, barley, It can be used to dress seeds such as rye, oats and triticale. and also corn, rice, rapeseed, peas, beans, cotton , can also be used to dress sunflower, soybean and beet seeds, or It can be used to dress a wide variety of vegetable seeds. Seed dressing formulations that can be used in this way or their diluted application forms are It can also be used to dress the seeds of phenothiazines.
[0219] Seed dressing formulations that can be used according to the present invention or seed dressing formulations to which water has been added When treating seeds with a use form prepared by Any conventional mixing equipment is useful. Specifically, the procedure for seed dressing is as follows: The seeds are placed in a mixer, which may be operated batchwise or continuously. The specified amount of seed dressing formulation is added as is or after pre-dilution with water. and mix everything until the formulation is evenly distributed on the surface of the seeds. If appropriate, this is followed by a drying step.
[0220] The application rates of the seed dressing formulations that can be used according to the invention can vary within a relatively wide range. It can be considered that the specific content of the compound of formula (I) in the preparation and The application rate of the compound of formula (I) is generally 100 mg / kg of seeds. The amount is 0.001 to 50 g per kg of seeds, and preferably 0.01 to 15 g per kg of seeds.
[0221] animal health In the field of animal health, i.e. veterinary medicine, the compounds of formula (I) are It is active against parasites, especially against ectoparasites or endoparasites. "Endoparasites" include, inter alia, helminths and protozoa (e.g., coccidia). The parasite is typically and preferably an arthropod, in particular an insect or acarid. do.
[0222] In the field of veterinary medicine, compounds of formula (I) having a favorable degree of toxicity to warm-blooded animals are preferred. The compounds are used in animal breeding and livestock production in domestic animals, breeding animals, zoo animals, and research animals. Occurring in laboratory, experimental and domestic animals They are suitable for controlling all developmental stages or specific parasites of the parasite. It is active against the developmental stages of
[0223] Agricultural livestock can include, for example: mammals, e.g. Sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer, and , especially cattle and pigs; or poultry, such as turkeys, ducks, geese, and and, in particular, chickens; or fish or crustaceans, for example fish in aquaculture. or crustaceans; or optionally insects, such as bees.
[0224] Domestic animals can include, for example: mammals, e.g. Hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially Wild animals, cats; caged birds; reptiles; amphibians, or fish in an aquarium.
[0225] In certain embodiments, a compound of Formula (I) is administered to a mammal.
[0226] In another particular embodiment, the compounds of formula (I) are effective against birds, i.e., caged birds. , or, in particular, to poultry.
[0227] By using the compounds of formula (I) to control animal parasites, To reduce or prevent illness and mortality in animals and to improve performance e) To reduce or prevent the deterioration of (meat, milk, wool, leather, eggs, honey, etc.) It is intended that this will result in more economical and easier animal care and better A healthy animal state can be achieved.
[0228] The term "control" or "controlling" means As used herein in connection with the field of animal health, compounds of formula (I) and reducing the occurrence of individual parasites in infected animals to harmless levels. More specifically, "control" means being effective in reducing the When used in the present invention, the compounds of formula (I) kill individual parasites. and is effective in inhibiting its growth or inhibiting its proliferation. do.
[0229] Representative arthropods include, but are not limited to: R: From the order Anoplurida, for example, Haematopinus species atopinus spp.), Linognathus spp. ), Pediculus spp., Phtirus spp. spp.), Solenopotes spp.; Order Mallophagida and suborder Amblycelina cerina and the suborder Ischnocerina, e.g., Bobi Bovicola spp., Damalina spp. ), Felicola spp.; Lepik entron spp.), Menopon spp., Trichodectes Trichodectes spp., Trimenopon spp. on spp.), Trinoton spp., Wernechiella spp. species (Werneckiella spp.); Diptera and Nematocerina From the suborder Brachycerina, for example, Aedes species spp.), Anopheles spp., Achilotus spp. Atylotus spp., Braula spp., Calliphora spp. Calliphora spp., Chrysomyia spp. pp.), Chrysops spp., Culex spp. spp.), Culicoides spp., Eucimurium Eusimulium spp., Fannia spp. , Gasterophilus spp., Glossina spp. lossina spp.), Haematobia spp., Haematopota spp., Hippo bosca spp.), Hybomitra spp., Hydrota Hydrotaea spp., Hypoderma spp. pp.), Lipoptena spp., Lucilia spp. lia spp.), Lutzomyia spp., Merophaga Melophagus spp., Morellia spp. .), Musca spp., Odagmia spp. .), Oestrus spp., Phillipomia spp. ipomyia spp., Phlebotomus spp. , Rhinoestrus spp., Sarcophaga spp. rcophaga spp.), Simulium spp., Stomoxys spp., Tabanus spp. ), Tipula spp., Wilhelmia spp. spp.), Wohlfahrtia spp.; From the order Siphonapterida, for example, Ceratophilus species tophyllus spp.), Ctenocephalides spp. des spp.), Pulex spp., Tunga spp. spp.), Xenopsylla spp.; From the order Heteropterida, for example, Cim ex spp.), Panstrongylus spp. , Rhodnius spp., Triatoma spp. spp.); and harmful and sanitary pests of the order Blattaria (Blattarida).
[0230] Additionally, among arthropods, examples include, but are not limited to, the following mites: You can: Acari (Acarina) and Metastigmatidae mata), for example, Argasidae, for example, Argus species ( Argas spp., Ornithodorus spp. , Otobius spp., Ixodidae, e.g. For example, Amblyomma spp., Dermacentor spp. ermacentor spp.), Haemaphysalis spp. s spp.), Hyalomma spp., Ixodes spp. xodes spp.), Rhipicephalus (Boophilus) spp. lus(Boophilus) spp.), Rhipicephalus spp. alus spp. (the original genus of multihost mites); Mesostigmatidae ta), for example, Dermanyssus spp., Ornithoptera Ornithonyssus spp., Pneumonisus spp. monyssus spp.), Raillietia spp. , Sternostoma spp., Tropilaelapus spp. Tropilaelaps spp., Varroa spp.; Actinedida (Prostigmata), e.g., Acara Acarapis spp., Cheyletiell spp. a spp.), Demodex spp., Listrophorus spp. Listrophorus spp., Myobia spp., Ne Neotrombicula spp., Ornithocheirretia spp. species (Ornithocheyletia spp.), Psore rgates spp.), Trombicula spp.; and Acaridida (Astigmata), e.g., Acarus Acarus spp., Caloglyphus spp. .), Chorioptes spp., Cyt odites spp.), Hypodectes spp., Knemidocoptes spp., Laminosioptes spp. (Laminosioptes spp.), Notoedres spp. spp.), Otodectes spp., Psoroptes spp. Psoroptes spp., Pterolichus spp. .), Sarcoptes spp., Trixacarus spp. ixacarus spp., Tyrophagus spp. .
[0231] Representative parasitic protozoa include, but are not limited to, the following: You can: Subphylum Mastigophora (Flagellata), e.g. For example: Metamonada: Diplomonadida da), for example, Giardia spp., Spironucleus spp. species (Spironucleus spp.); Parabasala: Trichomonadida da), for example, Histomonas spp., Pentatric Pentatrichomonas spp., Tetratrichomonas spp. species (Tetratrichomonas spp.), Trichomonas species (Tricho monas spp.), Tritrichomonas sp. p); Euglenozoa: Order Trypanosomatida matida), for example, Leishmania spp., Trypanosoma spp.; Sarcomastigophora (Rhizopodia) da)), for example, Entamoebidae, for example, Entamoebidae Entamoeba spp., Centramo ebidae), e.g., Acanthamoeba sp., Euamoebidae, e.g., Hartmanella species nella sp.); Alveolata, e.g., Apicomplexa mplexa) (Sporozoa), e.g., Cryptosporidium spp. (Cryptosporidium spp.); Eimeriida ), for example, Besnoitia spp., Cystoisospora Cystoisospora spp., Eimeria spp. pp.), Hammondia spp., Isospora spp. spora spp.), Neospora spp., Sarcosis Sarcocystis spp., Toxoplasma spp. sma spp.); Adeleida, e.g., Hepatozoon spp. species (Hepatozoon spp.), Klossiella sp. p.); Haemosporida, e.g., Leucocytozoa Leucocytozoon spp., Plasmodium spp. dium spp.); of the order Piroplasmida, e.g. Babesia spp., Ciliophora spp. spp.), Echinozoon spp., Theileria spp. Theileria spp.; Vesibuliferidae a) for example, Balantidium spp., Bukist Nella species (Buxtonella spp.); Microspora, e.g., Encephalitzoon species ephalitozoon spp.), Enterocytozoon spp. ozoon spp.), Globidium spp., Nosema Nosema spp. and also, for example, Myxozoa spp. oa spp.).
[0232] Helminths that are pathogenic to humans or animals include, for example, Acanthopanax hocephala), Nematoda, Pentastoma and Platyhelminthes (platyhelmintha) [e.g., monogenea, cestodes ( cestodes and trematodes.
[0233] Representative helminths include, but are not limited to: : Monogenea: e.g., Dactylogyrus species rus spp.), Gyrodactylus spp., Mi Microbothrium spp., Po lystoma spp.), Troglocephalus spp. spp.); Cestodes: Order Pseudophyllid ea), for example: Bothridium spp., Diphyllo Diphyllobothrium spp., Diphlogonoporus spp. species (Diplogonoporus spp.), Ichthyobothrium spp. yobothrium spp.), Ligula spp., Cystose Schistocephalus spp., Spirometra spp. irometra spp.); From the order Cyclophyllida, for example: Andira spp. (Andyra spp.), Anoplocephala spp. pp.), Avitellina spp., Be rtiella spp.), Cittotaenia spp. , Davainea spp., Diorchis spp. spp.), Diplopylidium spp., Dipi Dipylidium spp., Echinococcus spp. coccus spp., Echinocotyle spp. , Echinolepis spp., Hyda tigera spp.), Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp. (Mesocestoides spp.), Moniezia sp. p.), Paranoplocephala spp., La Raillietina spp., Stiles spp. ia spp.), Taenia spp., Th ysaniezia spp.), Thysanosoma spp. ); Trematodes: of the subclass Digenea, for example: Austrobilharzia spp., Brachyraima Brachylaima spp., Calicophoron spp. on spp.), Catatropis spp., Chronorchis Clonorchis spp., Collyriclu m spp.), Cotylophoron spp., Cyclococcus Elm species (Cyclocoelum spp.), Dicro coelium spp.), Diplostomum spp. ), Echinochasmus spp., Echinochasmus spp. Echinoparyphium spp., Echinostoma spp. ostoma spp.), Eurytrema spp., Fa Fasciola spp., Fascioli spp. des spp.), Fasciolopsis spp., Fischoederius spp., Gastrothyrax Gastrothylacus spp., Gigantobilharzia spp. antobilharzia spp.), Gigantocot yle spp.), Heterophyes spp., Hypo Hypoderaeum spp., Leucochloridium spp. ucochloridium spp.), Metagonimus spp. spp.), Metorchis spp., Nanophyetus spp. (Nanophyetus spp.), Notocotylus spp. spp.), Opisthorchis spp., Ornithobia Ornithobilharzia spp., Paragonimus spp. Paragonimus spp., Paramphist omum spp.), Plagiorchis spp., Po Posthodiplostomum spp., Prost Prosthogonimus spp., Schistosoma spp. stosoma spp.), Trichobilharzi spp. a spp.), Troglotrema spp., Typhloco Elm species (Typhlocoelum spp.); Nematodes: of the order Trichinellida For example: Capillaria spp., Eucoleus spp. ucoleus spp.), Paracapillaria spp. pp.), Trichinella spp., Trichomosoides spp. Species (Trichomosoides spp.), Trichuris sp. spp.); From the order Tylenchida, for example: Micronema species onema spp.), Parastrongyloi spp. des spp.), Strongyloides spp. ); Order Rhabditina, for example: Aerulostrongylus Aelurostrongylus spp., Amido stomum spp.), Ancylostoma spp. , Angiostrongylus spp., Bronchus Bronchonema spp., Bunostomum spp. mum spp.), Chabertia spp., Cooperia spp. Cooperia spp., Cooperioides spp. spp.), Crenosoma spp., Cyatostomum spp. (Cyathostomum spp.), Cyclococcus spp. rcus spp.), Cyclodontostomum spp. spp.), Cyclocercus spp., Silico Stephanus spp. (Cylicostephanus spp.), Cylindrophallin Cylindropharynx spp., Cys tocaulus spp.), Dictyocaulus spp. pp.), Elaphostrongylus spp. , Filaroides spp., Globocephalus spp. lobocephalus spp.), Graphidium spp. spp.), Gyalocephalus spp., fly fly Haemonchus spp., Heligmosomoides spp. mosomoides spp.), Hyostrongylus spp. us spp.), Marshallagia spp., Meta Strongylus spp. (Metastrongylus spp.), Muellerius spp. ( Muellerius spp., Necator spp., Nema Nematodirus spp., Neostrongylus spp. strongylus spp.), Nippostron gylus spp.), Obeliscoides spp. ), Oesophagodontus spp., Oeso Oesophagostomum spp., Orlanus spp. Ollulanus spp.; Ornithostrongylus spp. ongylus spp.), Oslerus spp., Oslerus Ostertagia spp., Paracooperia spp. peria spp.), Paraclenosoma spp. ), Parafilaroides spp., Parelaphos Parelaphostrongylus spp., Pneumoca Pneumocaulus spp., Pneumostrongylus spp. neumostrongylus spp.), Poteriostomum spp. stomum spp.), Protostrongylu s spp.), Spicocaulus spp., Stepha Stephanurus spp., Strongylus spp. ylus spp.), Syngamus spp., Terador's heron Teladorsagia spp., Trichonema spp. a spp.), Trichostrongylus sp. p.), Triodontophorus spp., Toro Troglostrongylus spp., Unshinari Uncinaria spp.; In the order Spirurida, for example: Acanthocheironema spp. Acanthocheilonema spp.), Anisakis spp. spp.), Ascaridia spp.; Ascaris spp. Ascaris spp.), Ascarops spp., Ascarops Aspiculuris spp., Baylisascaris spp. lisascaris spp.), Brugia spp., Serco Cercopithifilaria spp., Crassicauda Crassicauda spp., Dipetalonema spp. ma spp.), Dirofilaria spp., Drac Dracunculus spp.; Draschia spp. a spp.), Enterobius spp., filariasis Filaria spp., Gnathostoma sp. p.), Gongylonema spp., Habronema spp. abronema spp.), Heterakis spp.; Litomosoides spp., Loa spp. .), Onchocerca spp., Oxyuris spp. yuris spp.), Parabronema spp., Parafilaria spp., Parascaris spp. scaris spp.), Passalurus spp., Physaloptera spp., Probstomaillia spp. robstmayria spp., Pseudofilaria spp. ria spp.), Setaria spp., Scutella spp. Skjrabinema spp., Spirocerca spp. spp.), Stephanofilaria spp. , Strongyluris spp., Syphasia spp. hacia spp.), Thelazia spp., Toxaskari Toxascaris spp., Toxocara sp. p.), Wuchereria spp.; Phylum Acantocephala: Order Oligocene anthorhynchida, for example: Macra canthorhynchus spp.), Prosthen orchis spp.; Moniliformida ), for example: Moniliformis spp.; From the order Polymorphida, for example: Filicoris species licollis spp.); Coleoptera (Echinorhynchida) ), for example, Acanthocephalus spp. , Echinorhynchus spp., Leptorhynchoides Leptorhynchoides spp.; Phylum Pentastoma: Order Porocephali da), for example, Linguatula spp.
[0234] In the field of veterinary medicine and in animal husbandry, the administration of compounds of formula (I) , by methods commonly known in the art, e.g., in the form of a suitable preparation. The administration is carried out enterally, parenterally, transdermally or intranasally. Can be administered methaphylactically or therapeutically .
[0235] Thus, one embodiment of the present invention provides a compound of formula (I) for use as a medicament. Pertaining to things.
[0236] Another embodiment is an antiendoparasitic agent. t) a compound of formula (I) for use as a
[0237] Another particular embodiment is for use as an antihelmintic agent. and more particularly nematicides, flatwormicides, cidal agent, acanthocephalic agent as a pentastomicidal agent The present invention relates to a compound of formula (I) for use in
[0238] Another particular embodiment is as an antiprotozoal agent The present invention relates to a compound of formula (I) for use in
[0239] Another embodiment is an antiectoparasitic agent. In particular, for use as arthropodicides and more particularly for use as insecticides or acaricides. The present invention relates to a compound represented by formula (I) for use in the treatment of a pulmonary arthritis.
[0240] A further aspect of the present invention is a method for treating a stomach ulcer by administering to a subject a composition comprising an effective amount of at least one compound of formula (I) and A veterinary preparation containing at least one of the following: and excipients (e.g., solid or liquid diluents), pharmaceutically acceptable adjuvants (e.g., surfactants), especially pharmaceutically acceptable surfactants customarily used in veterinary formulations. excipients that may be used and / or pharmaceutically acceptable excipients customarily used in veterinary formulations. Aids in obtaining.
[0241] A related aspect of the invention is a method for preparing the veterinary formulations described herein. wherein the method comprises administering at least one compound of formula (I) to a pharmaceutically acceptable carrier. acceptable excipients and / or adjuvants (especially pharmaceuticals customarily used in veterinary preparations) and / or veterinary formulations. The method includes mixing the composition with a pharmaceutical composition containing the compound (a pharmaceutical composition containing the compound and a ...).
[0242] Another particular embodiment of the present invention is an ectoparasiticide formulation according to the above embodiment. siticidal formulations and endoparasiticide formulations Veterinary formulations selected from the group consisting of parasiticidal formulations Preparations, more particularly anthelmintic preparations, antiprotozoal preparations formulations and arthropodicides Veterinary formulations selected from the group of , nematicide preparations, flatworm-killing preparations (platyhelminthicidal for mulations), acanthocephalic veterinary drug preparations (acanthocephalicidal formulations, pentastomicidal formulations (pentastomicidal f Veterinary preparations selected from the group consisting of insecticide formulations and acaricide formulations. and methods for preparing them.
[0243] Another aspect is directed to parasitic infections, particularly the ectoparasites and endoparasites described herein. a method for treating an infection by a parasite selected from the group of organisms, said method comprising: and administering to an animal (particularly a non-human animal) in need of such treatment an effective amount of a compound of formula (I) By applying the compound.
[0244] Another aspect is directed to parasitic infections, particularly the ectoparasites and endoparasites described herein. a method for treating an infection by a parasite selected from the group of organisms, said method comprising: , as defined herein, in animals (particularly non-human animals) in need of such treatment. By applying veterinary preparations.
[0245] Another aspect relates to parasitic infections in animals (particularly non-human animals), particularly those described herein. Treatment of infections caused by parasites selected from the group of ectoparasites and endoparasites described The present invention relates to the use of a compound of formula (I) in
[0246] In the context of the field of animal health or veterinary medicine, the term "treatment" refers to prophylaxis. This includes preventative, metaphylactic or therapeutic treatment.
[0247] In a particular embodiment, for the field of veterinary medicine, at least one compound of formula (I) Mixtures of compounds with other active ingredients (especially endoparasiticides and ectoparasiticides) is provided.
[0248] In the field of animal health, a "mixture" is a mixture of two (or more) different active ingredients. It does not merely mean that the active ingredients are formulated into a common formulation and thereby applied together. It also refers to a product that does not contain a single active compound but contains a separate formulation for each active compound. If more than two active compounds are applied, all active compounds should be formulated in a common formulation. Alternatively, all active compounds can be formulated in separate formulations; In other words, some of the active compounds are formulated together and some of the active compounds are formulated separately. In separate formulations, the active compounds are applied separately. The application can be either sequential or sequential.
[0249] The active compounds identified herein by "common name" are known and For example, as described in the "Pesticide Manual" (see above). or can be found on the internet (e.g., http: / / www.alanwood.net / pesticides).
[0250] Representative active ingredients selected from the group of ectoparasiticides as mixing partners include: including, but not limited to, the insecticides and acaricides detailed above. Further active ingredients that may be used are listed in the current IRA C Mode of Action Classification Scheme” According to the above classification based on: (1) acetylcholinesterase (AC) hE) inhibitors; (2) GABA-regulated chloride channel blockers; (3) sodium channel (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators (5) Nicotinic acetylcholine receptor (nAChR) allosteric (6) Glutamate-regulated chloride channel (GluCl) allosterol (7) Juvenile hormone mimetics; (8) Various unspecified (multiple) (9) Chordotonal organ modulators; (10) Mite growth inhibitors; (12) Mites Inhibitors of mitochondrial ATP synthase, e.g., ATP disruptors; (13) protease inhibitors; Uncoupler of oxidative phosphorylation by disrupting the ATP gradient; (14) Nicotinic acetate Chiral receptor channel blockers; (15) Chitin biosynthesis inhibitors (type 0); (1 6) Chitin biosynthesis inhibitors (type 1); (17) Molting disruptors (especially Diptera ( (i.e., against Diptera); (18) Ecdysone receptor agonists; (19) Octopamine receptor agonists (21) Mitochondrial complex I electron transport inhibitors; (25) Mitochondrial Complex II electron transport inhibitors; (20) Mitochondrial complex III electron transport inhibitors; (2 2) Voltage-dependent sodium channel blockers; (23) Acetyl-CoA carboxylase inhibitors;(28) ryanodine receptor modulators; Active compounds with unknown or unspecified mechanisms of action, e.g., fentrif phenanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, Rubendimine, dicyclanil, amidoflumet, chinomethionate, triatene, clo Thiazoben, tetrasulfur, potassium oleate, petroleum, methoxadiazone, gossypurule, Flutensin, bromopropylate, cryolite; Another class of compounds, e.g., butacarb, dimethylane, cloethocarb, phosphocarb Bu, Pirimiphos (-ethyl), Parathion (-ethyl), Methacrifos, o-Salicylic Acid Isopropyl, trichlorfon, tigolaner, sulprofos, Ropafos, Cebufos, Pyridathione, Protoate, Diclofenthion, Demeton-S -Methyl sulfone, isazofos, cyanofenphos, dialifos, carbophenothion, Altatiophos, Allomfenvinphos (-methyl), Azinphos (-ethyl), Chlor Pyriphos (-ethyl), phosmetiran, iodofenphos, dioxabenzophos, hormon Thione, fonofos, flupyrazophos, fensulfothion, etrimphos; Organochlorine compounds, such as camphechlor, lindane, heptachlor; or phenyl Pyrazoles, such as acetoprole, pyrafluprole, pyriprole, vaniliprole or isoxazolines, such as sarolaner, afoxolane Le, lotilaner, fluralaner; Pyrethroids, such as (cis-, trans-) metofluthrin, profluthrin, Flufenprox, flubrocythrinate, fubufenprox, fenflutri Protrifenbut, Pyresmethrin, RU15525, Teralethrin, Cis-less Methrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyritri cis-cypermethrin, cis-permethrin, clocithrin, cyhalothrin (lambda -), clovaporthrin, or halogenated hydrocarbons (HCHs); Neonicotinoids, for example, nithiazine; Dichloromezotiaz, triflumezopyrim; Macrocyclic lactones, such as nemadectin, ivermectin, latidectin, moxide Cutin, Selamectin, Eprinomectin, Doramectin, Emamectin Benzoate; rubemycin oxime; Triplene, epofenonane, diofenolan; Biological agents, hormones, or pheromones, e.g., natural products, e.g., tree thuringiensin, codlemone, or neem components; Dinitrophenols, such as dinocap, dinobuton, binapacryl; Benzoylureas, for example, fluazuron, penfluron; Amidine derivatives such as chlormebuform, cymia Zoll, Demiditraz; Bee hive varroa acaricide icides), for example, organic acids, e.g., formic acid, oxalic acid.
[0251] Representative active ingredients selected from the group of endoparasiticides as mixing partners include: These include, but are not limited to, antiparasitic and antiprotozoal compounds. can.
[0252] The anthelmintic active compound includes, but is not limited to, the following nematicidal active compounds, suction-killing compounds, Mention may be made of insecticidal and / or cestocidal compounds, such as: From the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Mil Bemectin, ivermectin, emamectin, milbemycin; From the class of the benzimidazoles and probenzimidazoles, for example: Oxyben oxibendazole, mebendazole, triclabendazole Iclabendazole, thiophanate, parbene parbendazole, oxfendazol e), netobimin, fenbendazole, febantel, thiabe thiabendazole, cyclobendazole, cambendazole, Albendazole-sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably from the class of cyclic depsipeptides, in particular The class of 24-membered cyclic depsipeptides, for example: emodepsid e), PF1022A; From the class of the tetrahydropyrimidines, for example: morantel, pyrantel, oxanthine Le; From the class of the imidazothiazoles, for example: butamisole, levamisole, tetramiso Rule; From the class of aminophenylamidines, for example: amidantel, deacylated amidantel le (dAMD), tribendimidine; From the class of aminoacetonitriles, for example: monepantel ; From the class of the paraherquamides, for example: paraherquamide, delquantel; From the class of salicylanilides, for example: tribromosalan, bromoxanide, bromine Anide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxa Nido; From the class of substituted phenols, for example: nitroxynil, bithionol, diisophenone hexachlorophene, niclofolan, meniclofolan ); From the class of organophosphates, for example: trichlorfon, naphthalophos (naph thalofos), dichlorvos / DDVP, crufomate, coumaphos, haloxone; From the class of piperazinones / quinolines, for example: praziquantel antel), epsiprantel; From the class of piperazines, for example: piperazine, hydroxyzine; From the class of tetracyclines, for example: tetracycline, chlorotetracycline , doxycycline, oxytetracycline, rolitetracycline; Various other classes, for example: bunamidine, niridazole, resolantel, omuf Arothrin, Oltipraz, Nitroscanate, Nitroxynil, Oxamniquine, Mirasa Mirasan, miracil, lucanton, hycanton, hetri Hetolin, emetine, diethylcarbamazine, dichlorophen, diamphen Netide, clonazepam, bephenium, amoscanate, clo Ruslon.
[0253] Antiprotozoan active compounds include, but are not limited to, the following active compounds: Can: From the class of triazines, for example: diclazuril, ponazuril, letrazuril, tort Razuril; From the class of polyether ionophores, for example: monensin, salinomycin, madu Ramycin, Narasin; From the class of macrocyclic lactones, for example: milbemycin, erythromycin; From the class of quinolones, for example: enrofloxacin, pradofloxacin; From the class of quinines, for example: chloroquine; From the class of pyrimidines, for example: pyrimethamine; From the class of sulfonamides, for example: sulfaquinoxaline, trimethoprim, sulfonamides phaclozin; From the class of thiamines, for example: amprolium; From the class of lincosamides, for example: clindamycin; From the class of carbanilides, for example: imidocarb; From the class of nitrofurans, for example: nifurtimox; From the class of quinazolinone alkaloids, for example: halofuginone; Of various different classes, for example: oxamniquine, paromomycin; Classes of vaccines or microbial antigens, such as: Babesia canis rossi sia canis rossi), Eimeria tenela la), Eimeria praecox, Eimeria Necatrix (Eimeria necatrix), Eimeria mitis (Eimer ia mitis), Eimeria maxima, Eimeria Eimeria brunetti, Eimeria acervulina Eimeria acervulina, Babesia canis bogerii canis vogeli), Leishmania infantum (Leishmania a infantum), Babesia canis canis (Babesia canis c anis, Dictyocaulus vivipa rus).
[0254] All named mixing partners are, where possible, compatible with their functional groups. In some cases, salts can be formed with appropriate bases or acids.
[0255] Vector control The compounds of formula (I) may be used in the control of vectors. For the purposes of the present invention, vectors are animals that carry pathogens (e.g., viruses, helminths, worms, single-celled organisms and bacteria) as reservoirs (plants, animals, humans, etc.) The pathogen is an arthropod (especially an insect or arachnid) that can carry the pathogen from the host. The body may be mechanically carried to the host (e.g., trachoma by non-biting flies) or may be host-borne. They can be delivered by injection into the body (eg, malaria parasites by mosquitoes).
[0256] Examples of vectors and the diseases or pathogens they carry are: (1) Mosquitoes Anopheles mosquitoes: malaria, filariasis; Culex: Japanese encephalitis, other viral diseases, filariasis, other carriage of helminths; Aedes mosquitoes: Yellow fever, dengue fever, other viral diseases, filariasis ; Black flies (Simuliidae): helminths (especially Onchocer ca volvulus)) conveyance; · House flies (Psychodidae): transmission of leishmaniasis; (2) Lice: skin infections, epidemic typhus; (3) Fleas: contagious diseases, typhus, tapeworms; (4) Flies: sleeping sickness (trypanosomiasis); cholera, another bacterial disease; (5) Mites: Acariosis, epidemic typhus, rickettsial pox, Tularemia, St. Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo hemorrhagic fever, Borreli borreliosis; (6) Ixodes: Borreliosis (borellioses), e.g., Lyme disease Borrelia (Borrelia burgdorferi sensu lato), Dutton regression Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiel la burnetii), babesiosis (Babesia c anis canis, ehrlichiosis.
[0257] In the sense of the present invention, examples of vectors are insects capable of transmitting plant viruses to plants. insects, such as aphids, flies, leafhoppers or thrips. Other vectors that can transmit the virus are spider mites, lice, beetles and nematodes. .
[0258] Further examples of vectors in the sense of the present invention are those that carry pathogens to animals and / or humans. insects and arachnids capable of killing insects, such as mosquitoes (especially Aedes species) Mosquitoes, Anopheles mosquitoes, e.g., A. gambiae mbiae), Anopheles arabiensis (A.arabiensis), Anopheles A. funestus, A. dirus (malaria) and Culex mosquitoes, psychodactyls ids), e.g., Phlebotomus, Lutz omyia), lice, fleas, flies, mites and ticks.
[0259] The compounds of formula (I) break down resistance ng), vector control is also possible.
[0260] The compounds of formula (I) are useful in the prevention of disease and / or vector-borne pathogens. Thus, a further aspect of the invention is a method for the prevention of, for example: In agriculture, horticulture, gardens and leisure facilities, and also in materials and Use of compounds of formula (I) for controlling vectors in the protection of stored products is.
[0261] Protection of industrial materials The compounds of formula (I) can be used to treat insects (e.g., Coleoptera ), Hymenoptera, Isoptera, Lepidoptera Lepidoptera, Psocoptera and Zygoptera Suitable for protecting industrial materials against attack or destruction by insects of the genus Gentoma There are.
[0262] In the context of the present invention, industrial materials are non-biological materials, such as, preferably, plastics, adhesives, etc. It is understood to mean adhesives, sizes, paper and cardboard, leather, wood, engineered wood products, and paints. It is understood that the present invention is particularly preferably used to protect wood.
[0263] In a further embodiment, the compound of formula (I) is Use in conjunction with an insecticide and / or at least one fungicide.
[0264] In a further embodiment, the compound of formula (I) is a ready-to-use They exist as (to-use) pesticides, i.e., they can be used without further modification. Suitable further insecticides or fungicides may be applied to the material without further application. , in particular those listed above.
[0265] Surprisingly, the compounds of formula (I) are useful in treating conditions that come into contact with seawater or freshwater, especially hulls, screens, nets, structures, mooring equipment and signalling systems from fouling. Similarly, it has been found that the compound represented by formula (I) The product can be used as a stain repellent either alone or in combination with another active compound.
[0266] Pest control in the sanitation sector The compounds of formula (I) are suitable for controlling pests in the hygiene sector, in particular The invention is applicable in the domestic sector, in the hygiene sector and in the protection of stored products. , especially in enclosed spaces (e.g., dwellings, factory corridors, offices, vehicle passenger compartments, livestock farms) To control insects, arachnids, ticks and mites encountered in the field. To control pests, the compounds of formula (I) can be used alone or in combination. are used in combination with other active compounds and / or auxiliaries. They are preferably The compounds of formula (I) are used in household insecticide products to treat susceptible and resistant species. It is effective against both sexes and all stages of development.
[0267] These pests include, for example, Scorpions of the Arachnida class. piones), Araneae and Opiliones Insect pests, Chilopoda and Diplopoda pests, insect pests Class Insecta, Order Blattodea, Order Coleoptera optera), Dermaptera, Diptera, Heteroptera, Hymenoptera, White-spotted stink bugs Isoptera, Lepidoptera, Phth iraptera), Psocoptera, Salta toria or Orthoptera), Siphonaptera and Pests of the order Zygentoma and Malacostraca Examples include pests of the order Isopoda.
[0268] They include, for example, aerosols, non-pressurized spray products, such as pump sprays and spray nozzles. Fog spray, automatic fogging system , fogger, foam, gel, cellulose or plastic evaporator - Evaporator products with tablets, liquid evaporators, gel and membrane evaporators, Propeller-driven evaporators, energy-free evaporation systems or passive evaporation systems , moth papers, moth bags and moth gels Use in moth gels or as granules or dusts for broadcast use. Use in bait for fishing or in bait stations. [Table 4] TIFF0007812478000022.tif221132
[0269] Description of preparation methods and intermediates The compound represented by formula (I') can be prepared as illustrated in Scheme 1 below. where R 1 , R 2 , R 3a , R 3b , R 4 , Q 1 , Q 2 and Y is as previously defined, and X represents OH or Cl.
[0270] Scheme 1 [ka]
[0271] X=OH The azole compound represented by formula (a) is reacted with a compound represented by formula (b) (X=OH). The compound of formula (I') is produced by reacting the compound with a carboxylic acid in a suitable solvent. (e.g., ethyl acetate or DMF) with an azole of formula (a) and a compound of formula (b) (X= OH) with a suitable coupling reagent (e.g., T3P®, HATU, DCC or HOBt) and a suitable base (e.g., triethylamine or DIPE A) is mixed at a temperature in the range of about 0 to 100°C to form a compound represented by formula (I'). This compound can then be isolated and, if desired, Purification can be achieved using techniques well known in the art, such as chromatography. Cut.
[0272] X=Cl The azole compound represented by formula (a) is reacted with a compound represented by formula (b) (X=Cl). and a carboxylic acid chloride to produce a compound of formula (I'). In a suitable solvent (e.g., dichloromethane or THF), an azole of formula (a) and an azole of formula (b) are reacted with each other. b) A carboxylic acid chloride (X = Cl) and a suitable base (e.g., triethylamine) or DIPEA) at a temperature in the range of 0 to 100°C, to form a compound represented by formula (I'). This compound can then be isolated and used as needed. Depending on the nature of the product, the product may be purified using techniques well known in the art, such as chromatography. It is possible.
[0273] Carboxylic acid represented by formula (b) (X=OH) and carboxylic acid represented by formula (b) (X=Cl) The carboxylic acid chlorides can be obtained commercially or by methods known to those skilled in the art. It can be synthesized by
[0274] For example, the carboxylic acid used to synthesize Examples I-048 and I-049 are WO2016198507, WO2015084936, and WO2015148354. In the same manner as in WO2015148373, copper iodide (I) and (E,E)-N,N'-silyl iodide were prepared. Cyclohexane-1,2-diylbis[1-(pyridin-2-yl)methanimine] (the latter (See US20030236413 for details) The synthesis can be carried out using a catalyst system similar to that described in the literature.
[0275] The requisite azole compounds of formula (a) are illustrated in Scheme 2 below. where R 1 , R 3a , R 3b , R 4 , Q 1 , Q 2 and Y are as previously described, and LG is a suitable leaving group (also See WO2017192385).
[0276] Scheme 2 [ka]
[0277] Reacting an amine of formula (c) with a substituted azole of formula (d) The compound represented by formula (a) is produced. an azole of formula (d) and an amine of formula (c) in dichloromethane or DMF and an appropriate A mixture of base (e.g., K2CO3, NaH, or DIPEA) is heated to a temperature in the range of about 20 to 120°C. The compound represented by formula (a) is then produced by mixing at a temperature within the range of , can be isolated and, if necessary, can be prepared by techniques known in the art, such as chromatography. Purification can be achieved using well known techniques.
[0278] Alternatively, a substituted azole of formula (d) can be reacted with ammonia to form a compound of formula For example, ammonia is reacted with a suitable solvent (e.g., methacrylonitrile). A solution of the substituted azole of formula (d) in ethanol was placed in a sealed container. The mixture is mixed in a tube at a temperature in the range of about 0 to 25°C to produce a compound represented by formula (e). The compound can then be isolated and, if necessary, triturated or the like. The product can be purified using ...
Claims
[Claim 1] Formula (b) * ) 【Chemistry 4】 [During the ceremony, E is hydrogen or C 1 -C 6 is alkyl; A is —CN, chlorine or fluorine; L is S, SO or SO 2 is] A compound represented by the formula:
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