Pesticidal 1-arylpyrazole-3-carboximidothioic acid esters

A compound having the formula:

• ##STR31## or an agriculturally acceptable salt thereof, wherein:
• R.sub.1 is H or halogen;
• R.sub.2 is H, halogen or lower alkyl;
• R.sub.3 is halogen, haloalkyl, haloalkoxy, R.sub.16 S(O).sub.n or SF.sub.5 ;
• R.sub.4 is H, halogen or lower alkyl;
• X is R.sub.6 or --S(O).sub.n --R.sub.5 ;
• n is 0, 1 or 2;
• R.sub.5 is a lower hydrocarbyl or halohydrocarbyl radical which is saturated or is ethylenically or acetylenically unsaturated, or a C.sub.3 -C.sub.5 cycloalkyl radical;
• R.sub.6 is one of the meanings given for R.sub.5, or R.sub.6 is thiocyanato, nitro, cyano or halogen;
• Z is hydrogen;
• halogen;
• a lower alkyl radical which is unsubstituted or is substituted by one or more substituents selected from the group consisting of halogen, hydroxy, alkoxy, alkenyl and cyano;
• R.sub.14 S(O).sub.n ;
• R.sub.16 S(O).sub.n alkyl;
• amino;
• R.sub.15 CO-- in which R.sub.15 is H or an alkyl radical which is unsubstituted or is substituted by one or more halogen, hydroxy or alkoxy;
• cyano;
• nitro;
• trialkylsilyl;
• trialkylsilymethyl;
• alkoxycarbonyl;
• alkylthiocarbonyl;
• hydrazino;
• --CH.dbd.NOH;
• --CH.dbd.NO-alkyl;
• C.sub.2 -C.sub.4 alkenyl;
• C.sub.2 -C.sub.4 alkynyl;
• alkoxy;
• alkylcarbonylthio;
• alkoxycarbonylthio;
• aroylthio;
• aryl-S(O).sub.n ;
• azido;
• arylalkyl-S(O).sub.n ;
• 1H-pyrrol-1-yl;
• 1H-pyrazol-1-yl;
• R.sub.7 NH--;
• or R.sub.8 R.sub.9 N--;
• each of R.sub.7, R.sub.8 and R.sub.9, which are identical or different, is lower alkyl, lower alkyl-S(O).sub.n, P(.dbd.O)(R.sub.5)(OR.sub.5), aroyl, aryloxycarbonyl, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl or alkylcarbonyl, the alkyl portion of which radicals is unsubstituted or is substituted by one or more R.sub.17 ;
• or R.sub.8 and R.sub.9 are joined so as together to form a divalent radical having 4 to 6 atoms in the chain, said divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene;
• Y is hydrogen or C.sub.3 -C.sub.7 cycloalkyl;
• or Y is an alkyl, alkenyl, alkynyl, arylalkyl, aroyl, alkoxycarbonyl, alkylcarbonyl or arylalkylcarbonyl radical, each of which is unsubstituted or is substituted by one or more R.sub.18 ;
• R.sub.10 is alkenyl, haloalkenyl, alkynyl or haloalkynyl, or R.sub.10 is alkyl optionally substituted by one or more R.sub.19, or R.sub.10 is aralkyl, aryl, pyridinyl, pyrimidinyl, trialkylsilyl or C.sub.3 -C.sub.7 cycloalkyl;
• R.sub.14 is lower alkyl, lower alkenyl or lower alkynyl, optionally substituted with halogen;
• R.sub.16 is lower alkyl or lower haloalkyl;
• R.sub.17 is hydrogen, nitro, cyano, alkoxy, haloalkoxy, R.sub.16 S(O).sub.n, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
• R.sub.18 is halogen, alkoxy, cyano, alkyl-S(O).sub.n or arylthio;
• R.sub.19 is alkoxy, alkoxycarbonyl, cyano, aminocarbonyl, hydroxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylamino, dialkylamino, amino, halogen, alkyl-S(O).sub.n, NO.sub.2, alkylcarbonyl, hydroxy, acylamino or acyloxy;
• and
• M is C-halo, C--CN, C--CH.sub.3, C--CH.sub.2 F, C--NO.sub.2, C--CH.sub.2 Cl or N, provided that when R.sub.1 is halogen, then M can also be CH.