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US 5,965,491 AGranted
Pesticidal 1-aryl-3-iminopyrazoles
AssigneeRhone-Poulenc Inc.
InventorsTai-Teh Wu, David Treadway Manning
Life of this patent
Estimating the term…
Abstract
1-Aryl-3-iminopyrazoles of the formula: ##STR1## wherein R.sub.31, R.sub.32, R.sub.33, R.sub.4, R.sub.5, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and Z are as defined in the specification, are useful as pesticides or as intermediates to other pesticides. Compositions comprising the compounds of formula (I) and methods for their use, particularly in agriculture or for animal protection, as pesticides, especially for controlling arthropods, are described.
Claims44
A compound having the formula:
- ##STR47## or a pesticidally acceptable salt thereof, wherein:
- R.sub.31 is H, CN, NO.sub.2, NO, SH, C.sub.1 -C.sub.6 alkylthio, NH.sub.2, P(O)(OR.sub.8)(OR.sub.9) or R.sub.38 ;
- or R.sub.31 is mono(C.sub.1 -C.sub.6 alkyl)amino, di(C.sub.1 -C.sub.6 alkyl)amino, formyl(C.sub.1 -C.sub.6 alkyl), C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.8 (cycloalkyl)alkyl, each of which alkyl is optionally substituted by one or more R.sub.35 ;
- or R.sub.31 is naphthyl or phenyl, each of which is optionally substituted by one or more R.sub.36 or R.sub.37 ;
- or R.sub.31 is NH--CO--NH--N.dbd.CR.sub.8 R.sub.9, NH--CS--NH--N.dbd.CR.sub.8 R.sub.9, NH--CO--NR.sub.8 R.sub.9, NH--CS--NR.sub.8 R.sub.9, NH--CO--OR.sub.8, NH--CS--OR.sub.8 or NH--CO--NH--NH.sub.2 ;
- R.sub.32 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.4 -C.sub.8 cycloalkylalkyl, each of which alkyl is optionally substituted by one or more R.sub.35 ;
- or R.sub.32 is phenyl, optionally substituted by one or more R.sub.36 or R.sub.37 ;
- or R.sub.32 is R.sub.38 ;
- R.sub.33 is a lone pair of electrons;
- or R.sub.33 is an oxygen or sulfur atom, linked to the nitrogen atom by a covalent bond or a bond which is partially covalent and partially ionic;
- or R.sub.33 is C.sub.1 -C.sub.6 alkyl, the nitrogen atom to which R.sub.33 is linked then being in the cationic form N.sup.+ ;
- or R.sub.31 and R.sub.33 together form C.sub.2 -C.sub.6 alkylene, wherein one or two of the carbon atoms is each optionally replaced by a heteroatom selected from the group consisting of O, S and N, the nitrogen atom to which R.sub.31, and R.sub.33 are linked then being in the cationic form N.sup.+ ;
- R.sub.35 is halogen, amino, C.sub.1 -C.sub.6 alkylamino, di(C.sub.1 -C.sub.6 alkyl)amino, NO.sub.2, CN, C.sub.1 -C.sub.6 alkoxy, (C.sub.1 -C.sub.6 alkoxy)carbonyl, hydroxycarbonyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, methylene, methylidyne, acetenyl or acetenyl(C.sub.1 -C.sub.6 alkyl);
- or R.sub.35 is phenyl, optionally substituted by one or more R.sub.36 ;
- or R.sub.35 is a heterocyclic ring having a total of 3 to 7 ring atoms of which 1 to 4 are heteroatoms selected from the group consisting of O, S and N, said heterocyclic ring being saturated or unsaturated and being optionally substituted by one or more R.sub.36 ;
- or R.sub.35 is OH, SH, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, aminocarbonyl, (C.sub.1 -C.sub.6)alkylaminocarbonyl, di(C.sub.1 -C.sub.6 alkyl)aminocarbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl or P(O)(OR.sub.8)(OR.sub.9);
- R.sub.36 is SF.sub.5, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, NO.sub.2, CN, amino, C.sub.1 -C.sub.6 alkylamino, di(C.sub.1 -C.sub.6 alkyl)amino, di(C.sub.1 -C.sub.6 alkyl)aminocarbonylamino, (C.sub.1 -C.sub.6 alkyl)aminocarbonylamino, aminocarbonylamino, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, (C.sub.1 -C.sub.6 alkyl)carbonylamino, (C.sub.1 -C.sub.6 alkoxy)carbonylamino, aminocarbonyl, di(C.sub.1 -C.sub.6 alkyl)aminocarbonyl, (C.sub.1 -C.sub.6 alkyl)aminocarbonyl, hydroxycarbonyl, aminocarbonyloxy, (C.sub.1 -C.sub.6 alkyl)aminocarbonyloxy, di(C.sub.1 -C.sub.6 alkyl)aminocarbonyloxy, hydroxy, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfonyl, P(O)(OR.sub.8)(OR.sub.9), (C.sub.1 -C.sub.6 alkyl)[(C.sub.1 -C.sub.6 alkyl)carbonyl]amino or phenylamino(C.sub.1 -C.sub.6 alkyl);
- R.sub.37 is R.sub.36, phenyl optionally substituted by one or more R.sub.36, phenoxy optionally substituted by one or more R.sub.36, or benzyl optionally substituted by one or more R.sub.36 ;
- R.sub.38 is a heterocyclic radical derived from a single heterocyclic ring or from a two ring fused heterocyclic system at least one ring of which is heterocyclic, each ring having 3 to 7 ring atoms, each heterocyclic ring having 1 to 4 hetero ring atoms selected from the group consisting of O, S and N, each ring being saturated or unsaturated and optionally having one or more substituents selected from the group consisting of R.sub.36 and phenyl optionally substituted by one or more R.sub.36 ;
- R.sub.8 and R.sub.9, which are the same or different, are each H or C.sub.1 -C.sub.6 alkyl optionally having one or more substituents selected from the group consisting of halogen, NO.sub.2, CN, CHO, OH, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, hydroxycarbonyl and carbamoyl;
- R.sub.4 is R.sub.11 or S(O).sub.n R.sub.11 ;
- R.sub.11 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.8 (cycloalkyl)alkyl, each of which is optionally substituted by one or more halogen;
- n is 0, 1 or 2;
- R.sub.5 is H, halogen, CN, S(O).sub.n R.sub.8, OR.sub.8, NR.sub.8 R.sub.9, N(R.sub.8)CON(R.sub.9)(R.sub.8), azido or --N.dbd.C(R.sub.10)(OR.sub.9);
- R.sub.10 has one of the meanings defined by R.sub.8 above, or R.sub.10 is benzyl or phenyl, each of which is optionally substituted by one or more R.sub.36 ;
- Z is N or C--R.sub.16 ;
- and
- R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16, which are the same or different, are each halogen, R.sub.8, OR.sub.8, SF.sub.5, S(O).sub.n R.sub.8, CN, NO.sub.2, CHO, C(O)R.sub.8 or COOR.sub.8.
25 more elements
Dependencies are inferred from the claim text.