Patent EA-003186-B1 (EA)
Title: Pesticidal 1-arylpyrazoles
Inventor: CHENE ALAIN
IPC: C07D/
Filed: 1997-12-18
Abstract: 1. A compound having the formula: wherein: X is -S(O)mR6 or R7, Y is hydrogen, C1-C4alkyl or cycloalkyl, comprising up to 4 carbon atoms, each of which is substituted with aminocarbonyl, C1-C6alkylsulfonyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, cyano or nitro; C3-C4alkenyl; C3-C5alkynyl; C1-C6alkylcarbonyl; substituted or unsubstituted C4-C8aroyl; C4-C8arylC1-C6alkylcarbonyl; C1-C6alkylsulfonyl; C1-C6alkoxycarbonylC1-C6alkylcarbonyl; haloC1-C6alkylcarbonyl; N-C1-C6alkylcarbamoul; C1-C6alkoxycarbonyl; C4-C8aryloxycarbonyl; C1-C6alkoxyC1-C6 alkylcarbonyl; alphahydroxyC4-C8arylC1-C6alkylcarbonyl; hydroxyC1-C6alkylcarbonyl; aminoC1-C6alkylcarbonyl; C(=O)S-C1-C6alkyl and triC1-C6alkylsilyl, wherein Z is C1-C6alkyl, halogen, amino, R12NH- or R13R14N-; R1 is hydrogen, C1-C6alkyl or -NR15R16; R2 hydrogen and halogen, R3 and R5 are hydrogen; R4 is halogen, halogen C1-C6 alkyl, halogen C1-C6 alkoxy; R6 is C1-C6alkyl or halogen C1-C6alkyl R7 is C1-C6alkyl or halogen C1-C6alkyl R12, R13, R14 are similar or different, and are R7S(O)r, C3-C6alkynyl or C1-C4alkoxycarbonyl; or C1-C6alkyl, C3-C6alkenyl, or -C(O)C1-C6alkyl, wherein the alkyl and alkenyl portions are optionally substituted by one or more R18; R15 and R16 are independently hydrogen or alkyl; R18 is cyano, nitro, alkoxy, haloalkoxy, -C(O)R7, R8S(O)s-, -C(O)OR9. aminocarbonyl, alkylaminocarbonyl, diC1-C6alkylaminocarbonyl, halogen, hydroxy, aminosulfonyl, C1-C6alkylaminosulfonyl or diC1-C6alkylaminosulfonyl; m, r, s are equal zero, one or two; M is C-halo, or N; or a geometric isomer, tautomeric form or pesticidally active salt thereof. 2. The compound of formula (I) according to Claim 1, which is: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-ethylamino-4-methylsulfinyl 1H-pyrazole-3-carboxaldehyde oxime: 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-methylamino-4-methylsulfinyl 1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio 1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-difluoromethylthio-1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio-1H-pyrazole-3-carboxaldehyde O-(methyl)oxime; 5-Amino-1 -[2 6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-l H-pyrazole-3-carboxaldehyde O-(acetyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(2-methylbenzoyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methoxycarbonyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-[2-(ethoxycarbonyl)propionyl]oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole-3-carboxaldehyde O-(acetyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole-3-carboxaldehyde O-(methoxycarbonyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(N-methylcarbamoyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(carboxymethyl)oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(tert-butyldimethylsilyl)oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-formyl-N-hydroxy-4-trifluoromethylthio-1H-pyrazole-3-carboximidamide; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-5-hydroxyiminomethyl-4-trifluoromethylthio-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(isopropyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(ethoxycarbonylmethyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(aminocarbonylmethyl)oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-[2-(ethylsulfonyl)ethyl]oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(2-cyanoethyl)oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylthio-1H-pyrazole-3-carboxaldehyde oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-5-methyl-1H-pyrazole-3-carboxaldehyde oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-5-methyl-1H-pyrazole-3-carboxaldehyde oxime; 1-[2-Chloro-4-(trifluoromethyl)phenyl]-5-[2-(ethylsulfonyl)ethylamino]-4methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-dimethylamino-4-methylthio1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-ethylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethyl-1H-pyrazole-3-carboxaldehyde oxime; 3-Acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole oxime; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-trifluoromethylsulfinyl-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-methoxy-4-trifluoromethylsulfinyl-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-ethylsulfinyl-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-ethylthio 1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methylsulfinyl-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-N-hydroxy-4-methylsulfinyl-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methyl sulfonyl-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methyl thio-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-ethylsulfonyl-1H-pyrazole-3-carboximidamide: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-methoxy-4methylsulfinyl-1H-pyrazole-3-carboximidamidel; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-methoxy-N-methyl4-methylsulfinyl-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4 [2-(fluoroethyl)sulfinyl]-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4 [2-(fluoroethyl)sulfonyl]-1H-pyrazole-3-carboximidamide; 5-Amino-1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-ethylsulfinyl-N-hydroxy-1H-pyrazole-3-carboximidamide; 5-Amino-1-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-methylsulfinyl-N-hydroxy-1H-pyrazole-3-carboximidamide; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-5-methylamino-4methylsulfinyl-1H-pyrazole-3-carboximidamide; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-ethylamino-N-hydroxy-4methylsulfinyl-1H-pyrazole-3-carboximidamide; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[2-(ethylsulfonyl)ethylamino]-N-hydroxy-4-methylsulfinyl-1H-pyrazole-3-carboximidamide; 5-[2-(Cyano)ethylamino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methylsulfinyl-1H-pyrazole-3-carboximidamide; 5-(Aminocarbonylmethylamino)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-methylsulfinyl-1H-pyrazole-3-carboximidamide; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-5-[2 (phenylsulfonyl)ethylamino]-N-hydroxy-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2,6-dibromo-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-hydroxy-1H-pyrazole-3-carboximidamide; 1-[2-Bromo-6-chloro-4-(trifluoromethyl)phenyl-5-ethylamino-4-methylsulfinyl-N-hydroxy-1H-pyrazole-3-carboximidamide; 5-Amino-1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboximidamide; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-5-[2 (methylsulfinyl)ethylamino]-N-hydroxy-1-H-pyrazole-3-carboximidamide: 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-5-[2 (methylsulfinyl)ethylamino]-N-hydroxy-1H-pyrazole-3-carboximidamide: 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-5-[2- (ethylsulfinyl)ethylamino]-N-hydroxy-1H-pyrazole-3-carboximidamide; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-5-[(prop-2-ynyl)amino]-N-hydroxy-1H-pyrazole-3-carboximidamide; and 5-Amino-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-N-hydroxy- 1H-pyrazole-3-carboximidamide. 3. A pesticidal composition comprising a compound of formula (I), as defined in claim 1, or a geometric isomer tautomeric form or pesticidally active salt thereof: and an agriculturally acceptable inert carrier therefor. 4. A method for the control of pests at a locus comprising applying to said locus a pesticidally effective amount of a compound of formula (I) defined in claim 1 or a geometric isomer tautomeric form or pesticidally active salt thereof. 5. A process for preparing a compound of formula (I) as defi