Biocidal esters of halo-4-alkenoic acids

A pesticide composition comprising an acceptable carrier and an insecticidally or miticidally effective amount of a compound of the formula:

• ##STR57## wherein:
• R.sub.1, R.sub.2, and R.sub.3 are independently H, a lower alkyl group having from 1 to 3 carbon atoms or halogen;
• R.sub.4 and R.sub.5 are independently H, a lower alkyl group having from 1 to 3 carbon atoms, polyhaloalkyl, haloalkyl, halogen, a lower alkenyl group having from 2 to 3 carbon atoms, a lower cycloalkyl group having from 3 to 5 carbon atoms, a lower cycloalkenyl group having from 3 to 5 carbon atoms, cyano, nitro, a lower alkoxy group having from 1 to 3 carbon atoms, arloxy, a lower alkylthio group having from 1 to 3 carbon atoms, arylthio, a lower alkylsulfinyl group having from 1 to 3 carbon atoms, arylsulfinyl, a lower alkylsulfonyl group having from 1 to 3 carbon atoms, arylsulfonyl, acylamido, or a lower dialkylamino group having from 1 to 3 carbon atoms;
• R.sub.6 is selected from the group consisting of:
• (1) cycloalkyl, alkenyl, branched alkenyl, or cycloalkenyl;
• or (2) a branched alkyl group having from 3 to 5 carbon atoms or an alkyl group having from 1 to 5 carbon atoms, with the proviso that R.sub.4 or R.sub.5 is other than hydrogen.
• R.sub.7 is a member selected from the group consisting of:
• ##STR58## wherein:
• X is hydrogen, cyano, ethynyl, thiamido, a lower alkyl group having from 1 to 3 carbon atoms, a lower cycloalkyl group having from 3 to 5 carbon atoms, a lower alkenyl group having from 2 to 5 carbon atoms, a low cycloalkenyl group having from 3 to 5 carbon atoms or polyhaloalkyl;
• Y is hydrogen, a lower alkyl group having from 1 to 3 carbon atoms, polyhaloalkyl, haloalkyl, halogen, cyano, nitro, a lower alkoxy group having from 1 to 3 carbon atoms, aryloxy, a lower alkylthio group having from 1 to 3 carbon atoms, arylthio, a lower alkylsulfinyl group having from 1-3 carbon atoms, arylsulfonyl, alkylsulfonyl, acylamido, or a lower dialkylamino group having from 1 to 3 carbon atoms;
• R.sub.8 is bromine or chlorine;
• and
• Z is oxygen, sulfur or its oxides, or methylene.

A method of controlling insects and mites which comprises subjecting them to a lethal amount of a composition of the formula:

• ##STR60## wherein R.sub.1, R.sub.2, and R.sub.3 are independently H, a lower alkyl group having from 1 to 3 carbon atoms or halogen;
• R.sub.4 and R.sub.5 are independently H, a lower alkyl group having from 1 to 3 carbon atoms, polyhaloalkyl, haloalkyl, halogen, a lower alkenyl group having from 2 to 3 carbon atoms, a lower cycloalkyl group having from 3 to 5 carbon atoms, a lower cycloalkenyl group having from 3 to 5 carbon atoms, cyano, nitro, a lower alkoxy group having from 1 to 3 carbon atoms, arloxy, a lower alkylthio group having from 1 to 3 carbon atoms, arylthio, a lower alkylsulfinyl group having from 1 to 3 carbon atoms, arylsulfinyl, a lower alkylsulfonyl group having from 1 to 3 carbon atoms, arylsulfonyl, acylamido, or a lower dialkylamino group having from 1 to 3 carbon atoms;
• R.sub.6 is selected from the group consisting of:
• (1) cycloalkyl, alkenyl, branched alkenyl, or cycloalkenyl;
• or (2) a branched alkyl group having from 3 to 5 carbon atoms or an alkyl group having from 1 to 5 carbon atoms, with the proviso that R.sub.4 or R.sub.5 is other than hydrogen;
• R.sub.7 is a member selected from the group consisting of:
• ##STR61## wherein:
• X is hydrogen, cyano, ethynyl, thiamido, a lower alkyl group having from 1 to 3 carbon atoms, a lower cycloalkyl group having from 3 to 5 carbon atoms, a lower alkenyl group having from 2 to 5 carbon atoms, a low cycloalkenyl group having from 3 to 5 carbon atoms or polyhaloalkyl;
• Y is hydrogen, a lower alkyl group having from 1 to 3 carbon atoms, polyhaloalkyl, haloalkyl, halogen, cyano, nitro, a lower alkoxy group having from 1 to 3 carbon atoms, aryloxy, a lower alkylthio group having from 1 to 3 carbon atoms, arylthio, a lower alkylsulfinyl group having from 1-3 carbon atoms, arylsulfonyl, alkylsulfonyl, acylamido, or a lower dialkylamio group having from 1 to 3 carbon atoms;
• R.sub.8 is bromine or chlorine;
• and
• Z is oxygen, sulfur or its oxides, or methylene.