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US 6,638,956 B2Granted
Pesticidal 1-arylpyrazoles
AssigneeRhone-Poulenc Inc.
InventorsTai-Teh Wu, Alain Chene, David Treadway Manning, Peter Wyatt Newsome, Nicholas Charles Ray, Jennifer Lantz Phillips, Patrick Doyle Lowder
Life of this patent
Estimating the term…
Abstract
The invention relates to novel 1-arylpyrazole oxime derivatives, of general formula (I) or (I bis) These compounds are found to be generally safe systemic insecticides for control of arthropod, nematode, helminth or protozoan pests including compositions and derivatives thereof.
Claims18
A compound having the formula:
- wherein:
- X is —S(O)mR6, or R7,
- Y is hydrogen, C-3 to C-6 alkenyl, alkynyl, formyl, alkylcarbonyl, cycloalkylcarbonyl, halocycloalkyl carbonyl, aroyl, arylalkylcarbonyl, alkylsulfonyl, arylsulfonyl, haloalkylcarbonyl, aminoalkylcarbonyl, alkylaminoalkylcarbonyl, dialkylaminoalkylcarbonyl, alkoxyalkylcarbonyl, aryloxyalkylcarbonyl, alkylthioalkylcarbonyl, alkylsulfonylalkylcarbonyl, arylthioalkylcarbonyl, N-alkylcarbamoyl, N-arylcarbamoyl, N-alkylthiocarbamoyl, N-arylthiocarbamoyl, alpha-hydroxyarylalkylcarbonyl, hydroxyalkylcarbonyl, carboxyalkylcarbonyl, alkoxycarbonylalkylcarbonyl, —P(═O)(O-Alkyl)2, —P(═S)(O-alkyl)2, —P(═O)(S-alkyl)2, —P(═S)(S-alkyl)2, trialkylsilyl, alkylcarbonylaminoalkylcarbonyl, alkylcarbonyloxyalkylcarbonyl, aryl, pyridinyl, pyrimidinyl, —C(═O)S-alkyl, —C(═O)S-aryl, —C(═O)S-alkylaryl, alkoxyalkoxycarbonyl, akylthioalkoxycarbonyl, alkylsulfonylalkoxycarbonyl, arylthioalkoxycarbonyl, alkoxycarbonyl, aryloxycarbonyl and aryloxycarbonylalkylcarbonyl;
- or alkyl or haloalkyl both of which are unsubstituted or substituted by alkoxy, alkoxycarbonyl, carboxy, cyano, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthio, nitro, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, amino, alkylamino, dialkylamino, hydroxy, alkylcarbonylamino or alkylcarbonyloxy;
- Z is hydrogen, halogen, —C(O)R7—, —S(O)nR8, —C(O)OR9, alkyl, haloalkyl, —OR9, —N═C(R10)(R11), alkenyl, hydrazino, alkylthiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl, —CHO, —CH═NOH, amino, R12NH— or R13R14N—;
- R1 is hydrogen, alkyl or —NR15R16;
- R2 is hydrogen or halogen;
- R3 and R5 are hydrogen, halogen or alkyl;
- R4 is halogen, haloalkyl, haloalkoxy, R17S(O)p— or SF5;
- R6 is alkyl or haloalkyl, alkenyl or haloalkenyl, alkynyl or haloalkynyl or cycloalkyl having 3 to 5 carbon atoms;
- R7 is alkyl or haloalkyl;
- R8 is R7 or phenyl;
- R9 and R10 are hydrogen, alkyl or haloalkyl:
- R11 is alkyl, haloalkyl, alkoxy, or a phenyl group which is unsubstituted or substituted by one or more groups selected from hydroxy, halogen, alkoxy, cyano, R7 or —S(O)qR7;
- R12, R13 and R14, which are identical or different, are R7S(O)r—, formyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl or aroyl;
- or alkyl, C-3 to C-6 alkenyl or —C(O)alkyl wherein the alkyl and alkenyl portions are unsubstituted or substituted by one or more R18;
- or
- R13 and R14 are joined so as together form a divalent radical having 4 to 6 atoms in the chain, this divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene;
- R15 and R16 are independently hydrogen or alkyl;
- R17 is haloalkyl;
- R18 is cyano, nitro, alkoxy, haloalkoxy, —C(O)R7, R8S(O)s—, —C(O)OR9, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- m, n, p, q, r and s are independent of one another zero, one or two;
- M is C-halo, C—CH3, C—CH2F, C—CH2Cl, C—NO2, or N;
- or a geometric isomer, tautomeric form or pesticidally active salt thereof.
21 more elements
A pesticidal composition comprising:
- (a) a compound of formula (I)
- wherein:
- X is —S(O)mR6 or R7,
- Y is hydrogen, C-3 to C-6 alkenyl, alkynyl, formyl, alkylcarbonyl, aroyl, arylalkylcarbonyl, alkylsulfonyl, arylsulfonyl, haloalkylcarbonyl, aminoalkylcarbonyl, alkylaminoalkylcarbonyl, dialkylaminoalkylcarbonyl, alkoxyalkylcarbonyl, aryloxyalkylcarbonyl, alkylthioalkylcarbonyl, alkylsulfonylalkylcarbonyl, arylthioalkylcarbonyl, N-alkylcarbamoyl, N-arylcarbamoyl, N-alkylthiocarbamoyl, N-arylthiocarbamoyl, alpha-hydroxyarylalkylcarbonyl, hydroxyalkylcarbonyl, carboxyalkylcarbonyl, alkoxycarbonylalkylcarbonyl, —P(═O)(O-Alkyl)2, —P(═S)(O-alkyl)2, —P(═O)(S-alkyl)2, —P(═S)(S-alkyl)2, trialkylsilyl, alkylcarbonylaminoalkylcarbonyl, alkylcarbonyloxyalkylcarbonyl, aryl, pyridinyl, pyrimidinyl, —C(═O)S-alkyl, —C(═O)S-aryl, —C(═O)S-alkylaryl, alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl, alkylsulfonylalkoxycarbonyl, arylthioalkoxycarbonyl, alkoxycarbonyl, aryloxycarbonyl and aryloxycarbonylalkylcarbonyl;
- or alkyl or haloalkyl both of which are unsubstituted or substituted by alkoxy, alkoxycarbonyl, carboxy, cyano, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthio, nitro, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, amino, alkylamino, dialkylamino, hydroxy, alkylcarbonylamino or alkylcarbonyloxy;
- Z is hydrogen, halogen, —C(O)R7—, —S(O)nR8, —C(O)OR9, alkyl, haloalkyl, —OR9, —N═C(R10)(R11), alkenyl, hydrazino, alkythiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl, —CHO, —CH═NOH, amino, R12NH— or R13R14N—;
- R1 is hydrogen, alkyl or —NR15R16;
- R2 is hydrogen or halogen;
- R3 and R5 are hydrogen, halogen or alkyl;
- R4 is halogen, haloalkyl, haloalkoxy, R17S(O)p— or SF5;
- R6 is alkyl or haloalkyl, alkenyl or haloalkenyl, alkynyl or haloalkynyl or cycloalkyl having 3 to 5 carbon atoms;
- R7 is alkyl or haloalkyl;
- R8 is R7 or phenyl;
- R9 and R10 are hydrogen, alkyl or haloalkyl;
- R11 is alkyl, haloalkyl, alkoxy, or a phenyl group which is unsubstituted or substituted by one or more groups selected from hydroxy, halogen, alkoxy, cyano, R7 or —S(O)qR7;
- R12, R13 and R14, which are identical or different, are R7S(O)r—, formyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl or aroyl;
- or alkyl, C-3 to C-6 alkenyl or —C(O)alkyl wherein the alkyl and alkenyl portions are unsubstituted or substituted by one or more R18;
- or
- R13 and R14 are joined so as together form a divalent radical having 4 to 6 atoms in the chain, this divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene;
- R15 and R16 are independently hydrogen or alkyl;
- R17 is haloalkyl;
- R18 is cyano, nitro, alkoxy, haloalkoxy, —C(O)R7, R8S(O)s—, —C(O)OR9, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- p1 m, n, p, q, r and s are independent of one another zero, one or two;
- M is C-halo, C—CH3, C—CH2F, C—CH2Cl, C—NO2, or N;
- or a geometric isomer, tautomeric form or pesticidally active salt thereof;
- and
- (b) an agriculturally acceptable inert carrier therefor.
24 more elements
Dependencies are inferred from the claim text.