Pesticide substituted diketonitriles

Abstract

The invention relates to diketontrile derivatives which have been discovered useful against arthropods, plant nematodes, helminth protozoan pests or as intermediates for such useful compounds which have general formula: ##STR1##

What is claimed is: 
     
       1. A method of controlling insects, aphids, mites, or nematodes at a locus which comprises treatment of the locus with an effective amount of a compound of the formula: ##STR27## wherein: R is: cyclopropyl, which is unsubstituted or is substituted by one or more substituents selected from the group consisting of R 6 , halogen, --CO 2  R 7 , --SR 71  and --OR 71  ;   R 1  is: hydrogen, chlorine, bromine, fluorine, methyl or methoxy;     R 2  is: a) hydrogen;   b) a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen, with the proviso that when R 2  is trifluromethyl, R 1 , R 3  and R 5  are hydrogen, and R 4  is S(O) n  R 83 , then n is 0;   c) a straight- or branched-chain alkyl radical having up to six carbon atoms, substituted by an --OR 6  group;   d) halogen;   e) cyano,--CO 2  R 6  --COR 7 , --NR 12  S(O) 2  R 8 , --(CR 13  R 14 ) t  S(O) q  R 8 , --SR 9 , --S(O) u  S(O) q  R 8 , --O(CH 2 ) m  OR 6 , --NR 10  R 11 , --CONR 10  R 15  or --OR 61  ; or   f) cycloalkyl having from three to six carbon atoms;     R 6  is: a) a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen; or   b) cycloalkyl having from three to six carbon atoms;     R 61  is: a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;     R 7  is: a) a straight- or branched-chain alkyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen; or   b) cycloalkyl having from three to six carbon atoms;     R 71  is: straight- or branched-chain alkyl having up to three carbon atoms;     R 8  is: a) a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   b) cycloalkyl having from three to six carbon atoms;   c) phenyl, which is unsubstituted or is substituted by from one to five     R 21  groups, which can be the same or different; or d) --CH 2  CN,--CH 2  CO 2  R 6  or --NR 10  R 11  ;     R 9  is: a straight- or branched-chain alkyl, alkenyl or alkynyl radical having three to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   with the proviso that when R 9  is sec-butyl, and R 1 , R 3  and R 5  are hydrogen, then R 4  is not trifluoromethyl;   b) C 1  -C 2  alkyl substituted with one or more halogen; or   c) --CH 2  CN or--CH 2  CO 2  R 6  ;     R 10  is: a) hydrogen;   b) a straight- or branched-chain alkyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen; or   c) cycloalkyl having from three to six carbon atoms;   provided that when R 7  and R 10  are part of a group --CONR 7  R 10  they can, together with the nitrogen to which they are attached, form a five or six membered ring optionally having one additional hetero ring atom which is oxygen or nitrogen, said ring being unsubstituted or being substituted by one or more alkyl, each having up to three carbon atoms;     R 11  is: a) a straight- or branched-chain alkyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   b) cycloalkyl having from three to six carbon atoms; or   c) --COR 7 , --CO 2  R 7  or--CONR 7  R 10  ;   provided that when R 10  and R 11  are part of a group --NR 10  R 11  they can, together with the nitrogen to which they are attached, form a five or six membered ring optionally having one additional hetero ring atom which is oxygen or nitrogen, said ring being unsubstituted or being substituted by one or more alkyl, each having up to three carbon atoms;     R 12  is: a) hydrogen;   b) a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   c) cycloalkyl having from three to six carbon atoms;   d) phenyl, which is unsubstituted or is substituted by from one to five     R 21  groups, which can be the same or different; or e) --COR 7 , --CO 2  R 7 , --CONR 7  R 10 , --OR 17  or --SO 2  R 7  ;   each of R 13  and R 14 , which can be the same or different, is:   a) hydrogen; or   b) a straight- or branched-chain alkyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;     R 15  is: R 7  or --OR 17  ;   provided that when R 10  and R 15  are part of a group --CONR 10  R 15  they can, together with the nitrogen to which they are attached, form a five or six membered ring optionally having one additional hetero ring atom which is oxygen or nitrogen, said ring being unsubstituted or being substituted by one or more alkyl, each having up to three carbon atoms;     R 17  is: straight- or branched-chain alkyl having up to six carbon atoms;     R 21  is: halogen, R 7 , nitro, cyano, --CO 2  R 7 , --S(O) n  R 7 , --NR 10  R 11  or --OR 7  ;   m is one, two or three;   n is zero, one or two;   q is zero, one or two; provided when R 2  is --S(O) u  S(O) q  R 8  then q is zero or two;   t is an integer from one to four, provided that when t is greater than one, the groups -(CR 13  R 14 )- can be the same or different;   u is zero or two;     R 3 , R 4  and R 5 , each being the same or different, are: a) hydrogen;   b) a straight- or branched-chain-alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   c) straight- or branched-chain alkyl having up to six carbon atoms, substituted by an --OR 6  group;   d) halogen;   e) nitro, cyano,--CO 2  R 6 , --COR 7 , --NR 12  SO2R 82 , --(CR 13  R 14 ) t  S(O) q  R 82  --S(O) u  S(O) q  R 82  --S(O) n  R 83  --O(CH 2 ) m  OR 6 , --NR 10  R 11 , --CONR 10  R 15  or --OR 81  ;   f) phenyl, which is unsubstituted or is substituted by from one to five     R 21  groups, which can be the same or different; or g) cycloalkyl having from three to six carbon atoms;     R 81  is: a) a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   b) phenyl, which is unsubstituted or is substituted by one to five R 21  groups, which can be the same or different; or   c) cycloalkyl having from three to six carbon atoms;     R 82  is: a) a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   b) cycloalkyl having from three to six carbon atoms;   c) phenyl, which is unsubstituted or is substituted by from one to five     R 21  groups, which can be the same or different; or d) --CH 2  CN,--CH 2  CO 2  R 6  or--NR 10  R 11  ; and     R 83  is: a) a straight- or branched-chain alkyl, alkenyl or alkynyl radical having up to six carbon atoms, said radical being unsubstituted or being substituted by one or more halogen;   b) cycloalkyl having from three to six carbon atoms;   c) phenyl, which is unsubstituted or is substituted by from one to five     R 21  groups, which can be the same or different; or d) --CH 2  CN,--CH 2  CO 2  R 6  or--NR 10  R 11  ;   provided that when R 3 , R 4  or R 5  is --S(O) u  S(O) q  R 82  then q is 0 or 2;   with the proviso that when R 2  is chlorine, R is cyclopropyl, R 1 , R 3 , R 5  are hydrogen, R 4  is --S(O) n  R 83 , and n is 2, then R 83  is other than ethyl or dimethylamino;   with the proviso that when R 2  is fluorine, R 1 , R 3  and R 5  are each hydrogen, R 4  is --S(O) n  R 83 , n is 2, and R is cyclopropyl, then R 83  is not methyl;   with the proviso that when R 2  is chlorine, R is cyclopropyl, R 1 , R 3 , R 5  are each hydrogen, R 4  is --NR 12  SO 2  R 82  and R 12  is hydrogen or methyl, then R 82  is other than methyl;   with the proviso that when R 2  is --NR 12  SO 2  R 8 , R is cyclopropyl, R 1 , R 3  and R 5  are each hydrogen, and R 8  and R 12  are methyl, then R 4  is other than methyl or nitro; and   with the proviso that when R 2  is bromine, R is cyclopropyl or 1-methylcyclopropyl, R 1 , R 3  and R 5  are all hydrogen, and R 4  is S(O) n  R 83 , then n is 0 or 1;   or an agriculturally acceptable salt, metal complex or enolic tautomeric form thereof.