Pesticidal 1-arylpyrazoles

A pestcidal composition comprising:

• (a) a compound of formula (I)
• 17
• 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, 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;
• and
• (b) an agriculturauly acceptable inert carrier therefor.

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)

• 18
• 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, pyrimdinyl, —C(═O)S-alkyl, —C(═O)S-aryl, —C(═O)S-alkylaryl, alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl, alkylsulfonylalkoxycarbonyl, arylthioalkoxycarbonyl, alkoxycarbonyl, aryloxycarbonyl and aryloxycarbonylalkycarbonyl;
• or alkyl or haloalkyl both of which are unsubstituted or substituted by alkoxy, alkoxycarbonyl, carboxy, cyano, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alklylthio, 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 diffrent, 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.

A compound of formula (I bis):

• 22
• wherein:
• A is —NR26—;
• Y1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, —S(O)aR28, —P(O)R29R30, —P(S)R29R30, —Si(R31)(R32)(R33), —C(O)R27, —C(S)R27, cyano or nitro;
• R19 is hydrogen, alkyl, haloalkyl, or —NR34R35;
• R20 is —S(O)bR36 or R37;
• R21 is hydrogen, halogen, —C(O)R38, —S(O)cR39, alkyl, haloalkyl, —OR40, —N═C(R41)(R42), alkenyl, —NR43R44, 1H-pyrrol-1-yl, 1H-pyrazol-1-yl, or —CH═NOH;
• R22, R23 and R25 are independently selected form hydrogen, halogen or alkyl;
• R24 is halogen, haloalkyl, haloalkoxy, —S(O)dR45 or SF5;
• R26 is hydrogen or substituted or unsubstituted alkyl;
• R27 is hydrogen, substituted or unsubstituted alkyl of C1 to C20, substituted or unsubstituted aryl, —OR46, —NR47R48, or —SR49;
• R28 is substituted or unsubstituted alkyl or substituted or unsubstituted aryl;
• R29 and R30 are independently selected from alkoxy and thioalkoxy;
• R31, R32 and R33 are independently selected from alkyl, haloalkyl and aryl;
• R34 and R35 are independently selected from hydrogen or substituted or unsubstituted alkyl;
• R36 is alkyl, alkenyl, alkynyl, or C3-C6 cycloalkyl each of which is optionally substituted by one or more halogens;
• R37 is alkyl or haloalkyl;
• R38 is hydrogen, alkyl, haloalkyl, alkoxy or thioalkoxy;
• R39 is alkyl haloalkyl or aryl;
• R40 and R41 are independently selected from hydrogen, alkyl and haloalkyl;
• R42 is alkyl haloalkyl, alkoxy or phenyl each of which is optionally substituted by one or more groups selected from hydroxy, halogen, alkoxy, —CN, alkyl, —S(O)ealkyl;
• R43 and R44 are independently selected from hydrogen, NH2, —S(O)fR50, —C(O)R51, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl and alkynyl;
• or R43 and R44 form together a divalent alkylene radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen, nitrogen and sulfur;
• R45 is haloalkyl;
• R46 and R49 are independently selected from substituted or unsubstituted alkyl and substituted or unsubstituted aryl;
• R47 and R48 are independently selected from hydrogen, substituted or unsubstituted alkyl and substituted or unsubstituted aryl;
• or R47 and R48 may form together a divalent alkylene radical which may be interrupted by one or more heteroatoms;
• R50 is substituted or unsubstituted alkyl;
• R51 is hydrogen, alkyl, haloalkyl, aryl, alkenyl, —OR52, —SR53, or —NR54R55;
• R52 and R53 are independently selected from alkyl and haloalkyl;
• R54 and R55 are independently selected from hydrogen, alkyl, haloalkyl and aryl;
• a, b, c, d, e and f independently represent zero, one or two;
• M1 is C-halo, C—CH3, C—CH2F, C—CH2Cl, C—NO2, or N;
• or a pesticidally acceptable salt thereof.

A pesticidal composition comprising:

• (a) a compound of formula (I bis)
• 23
• wherein:
• A is —NR26—;
• Y1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, —S(O)aR28, —P(O)R29R30, —P(S)R29R30, —Si(R31)(R32)(R33), —C(O)R27, —C(S)R27, cyano or nitro;
• R19 is hydrogen, alkyl, haloalkyl, or —NR34R35;
• R20 is —S(O)bR36 or R37;
• R21 is hydrogen, halogen, —C(O)R38, —S(O)cR39, alkyl, haloalkyl, —OR40, —N═C(R41)(R42), alkenyl, —NR43R44, 1H-pyrrol-1-yl, 1H-pyrazol-1-yl, or —CH═NOH;
• R22, R23 and R25 are independently selected from hydrogen, halogen or alkyl;
• R24 is halogen, haloalkyl, haloalkoxy, —S(O)dR45 or SF5;
• R26 is hydrogen or substituted or unsubstituted alkyl;
• R27 is hydrogen, substituted or unsubstituted alkyl of C1 to C20, substituted or unsubstituted aryl, —OR46, —NR47R48, or —SR49;
• R28 is substituted or unsubstituted alkyl or substituted or unsubstituted aryl;
• R29 and R30 are independently selected from alkoxy and thioalkoxy;
• R31, R32 and R33 are independently selected from alkyl, haloalkyl and aryl;
• R34 and R35 are independently selected from hydrogen or substituted or unsubstituted alkyl;
• R36 is alky, alkenyl, alkynyl, or C3-C6 cycloalkyl each of which is optionally substituted by one or more halogens;
• R37 is alkyl or haloalkyl;
• R38 is hydrogen, alkyl, haloalkyl, alkoxy or thioalkoxy;
• R39 is alkyl haloalkyl or aryl;
• R40 and R41 are independently selected from hydrogen, alkyl and haloalkyl;
• R42 is alkyl, haloalkyl, alkoxy or phenyl each of which is optionally substituted by one or more groups selected from hydroxy, halogen, alkoxy, —CN, alkyl, —S(O)ealkyl;
• R43 and R44 are independently selected from hydrogen, NH2, —S(O)fR50, —C(O)R51, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl and alkynyl;
• or R43 and R44 form together a divalent alkylene radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen, nitrogen and sulfur;
• R45 is haloalkyl;
• R46 and R49 are independently selected from substituted or unsubstituted alkyl and substituted or unsubstituted aryl;
• R47 and R48 are independently selected from hydrogen, substituted or unsubstituted alkyl and substituted or unsubstituted aryl;
• or R47 and R48 may form together a divalent alkylene radical which may be interrupted by one or more heteroatoms;
• R50 is substituted or unsubstituted alkyl;
• R51 is hydrogen, alkyl, haloalkyl, aryl, alkenyl, —OR52, —SR53, or —NR54R55;
• R52 and R53 are independently selected from alkyl and haloalkyl;
• R54 and R55 are independently selected from hydrogen, alkyl, haloalkyl and aryl;
• a, b, c, d, e and f independently represent zero, one or two;
• M1 is C-halo, C—CH3, C—CH2F, C—CH2Cl, C—NO2, or N;
• or a pesticidally acceptable salt thereof;
• and
• (b) an agriculturally acceptable carrier therefor.

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 bis):

• 24
• wherein:
• A is —NR26—;
• Y1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, —S(O)aR28, —P(O)R29R30, —P(S)R29R30, —Si(R31)(R32)(R33), —C(O)R27, —C(S)R27, cyano or nitro;
• R19 is hydrogen, alkyl, haloalkyl, or —NR34R35;
• R20 is —S(O)bR36 or R37;
• R21 is hydrogen, halogen, —C(O)R38, —S(O)cR39, alkyl, haloalkyl, —OR40, —N═C(R41)(R42), alkenyl, —NR43R44, 1H-pyrrol-1-yl, 1H-pyrazol-1-yl, or —CH═NOH;
• R22, R23 and R25 are independently selected from hydrogen, halogen or alkyl;
• R24 is halogen, haloalkyl, haloalkoxy, —S(O)dR45 or SF5;
• R26 is hydrogen or substituted or unsubstituted alkyl;
• R27 is hydrogen, substituted or unsubstituted alkyl of C1 to C20, substituted or unsubstituted aryl, —OR46, —NR47R48, or —SR49;
• R28 is substituted or unsubstituted alkyl or substituted or unsubstituted aryl;
• R29 and R30 are independently selected from alkoxy and thioalkoxy;
• R31, R32 and R33 are independently selected from alkyl, haloalkl and aryl;
• R34 and R35 are independently selected from hydrogen or substituted or unsubstituted alkyl;
• R36 is alkyl, alkenyl, alkynyl, or C3-C6 cycloalkyl each of which is optionally substituted by one or more halogens;
• R37 is alkyl or haloalkyl;
• R38 is hydrogen, alkyl, haloalkyl, alkoxy or thioalkoxy;
• R39 is alkyl haloalkyl or aryl;
• R40 and R41 are independently selected from hydrogen, alkyl and haloalkyl;
• R42 is alkyl, haloalkyl, alkoxy or phenyl each of which is optionally substituted by one or more groups selected from hydroxy, halogen, alkoxy, —CN, alkyl, —S(O)ealkyl;
• R43 and R44 are independently selected from hydrogen, NH2, —S(O)fR50, —C(O)R51, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl and alkynyl;
• or R43 and R44 form together a divalent alkylene radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen, nitrogen and sulfur;
• R45 is haloalkyl;
• R46 and R49 are independently selected from substituted or unsubstituted alkyl and substituted or unsubstituted aryl;
• R47 and R48 are independently selected from hydrogen, substituted or unsubstituted alkyl and substituted or unsubstituted aryl;
• or R47 and R48 may form together a divalent alkylene radical which may be interrupted by one or more heteroatoms;
• R50 is substituted or unsubstituted alkyl;
• R51 is hydrogen, alkyl, haloalkyl, aryl, alkenyl, —OR52, —SR53, or —NR54R55;
• R52 and R53 are independently selected from alkyl and haloalkyl;
• R54 and R55 are independently selected from hydrogen, alkyl, haloalkyl and aryl;
• a, b, c, d, e and f independently present zero, one or two;
• M1 is C-halo, C—CH3, C—CH2F, C—CH2Cl, C—NO2, or N;
• or a pesticidally acceptable salt thereof.