Biocidal esters of alkynoic acids
AssigneeUnion Carbide Corporation
InventorThomas N. Wheeler
Life of this patent
Estimating the term…
Abstract
This invention relates to novel ester compounds derived from alkynoic acids and to their preparation. This invention is also directed to insecticidal and miticidal compositions comprising an acceptable carrier and an insecticidally or miticidally effective amount of a novel ester compound of this invention as well as a method of controlling pests by subjecting them to an insecticidally or miticidally effective amount of a novel ester compound of this invention.
Claims27
A compound of the formula:
- ##STR16## wherein:
- R.sub.1 is:
- an alkyl or alkenyl group having no more than five carbon atoms, or
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms;
- R.sub.2 and R.sub.3 are independently:
- hydrogen, or
- an alkyl group having no more than three carbon atoms;
- R.sub.4 is:
- hydrogen,
- an alkyl or alkenyl group having no more than ten carbon atoms, or
- phenyl or phenyl substituted with alkyl, halogen, cyano, nitro, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or dialkylamino groups;
- and
- R.sub.5 is:
- hydrogen, or
- a member selected from the group consisting of:
- ##STR17## wherein:
- Z is:
- hydrogen,
- cyano,
- thioamido,
- an alkyl or haloalkyl group having no more than three carbon atoms,
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms, or
- an alkenyl, haloalkenyl, or alkynyl group having no more than five carbon atoms;
- Q and T are independently:
- hydrogen,
- cyano,
- nitro,
- halogen,
- alkyl,
- haloalkyl,
- alkylthio,
- alkylsulfinyl,
- alkylsulfonyl,
- dialkylamino,
- acylamido,
- alkoxy,
- aryloxy,
- arylthio,
- arylsulfinyl, or
- arylsulfonyl,
- provided that neither Q or T includes more than three aliphatic carbon atoms or more than six aromatic carbon atoms;
- W is:
- oxygen,
- sulfur or its oxides, or
- methylene;
- and
- Y is:
- bromine, or
- chlorine.
A compound of the formula:
- ##STR18## wherein:
- R.sub.1 is:
- ethyl, isopropyl or cyclopropyl;
- R.sub.2 and R.sub.3 are hydrogen or when either R.sub.2 or R.sub.3 is hydrogen then the other member of this pair is methyl;
- R.sub.4 is:
- hydrogen and
- R.sub.5 is:
- a member selected from the group consisting of:
- ##STR19## wherein:
- Z is:
- hydrogen,
- cyano,
- thioamido,
- an alkyl or haloalkyl group having no more than three carbon atoms,
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms, or
- an alkenyl, haloalkenyl, or alkynyl group having no more than five carbon atoms;
- Q and T are independently:
- hydrogen,
- cyano,
- nitro,
- halogen,
- alkyl,
- haloalkyl,
- alkylthio,
- alkylsulfinyl,
- alkylsulfonyl,
- dialkylamino,
- acylamido,
- alkoxy,
- aryloxy,
- arylthio,
- arylsulfinyl, or
- arylsulfonyl,
- provided that neither Q or T includes more than three aliphatic carbon atoms or more than six aromatic carbon atoms;
- W is:
- oxygen,
- sulfur or its oxides, or
- methylene;
- and
- Y is:
- bromine, or
- chlorine.
A compound of the formula:
- ##STR21## wherein:
- R.sub.1 is ethyl, isopropyl or cyclopropyl,
- R.sub.2 and R.sub.3 are independently hydrogen or methyl,
- R.sub.4 is hydrogen, and
- R.sub.5 is hydrogen.
A compound of the formula:
- ##STR22## wherein:
- R.sub.1 is ethyl, isopropyl or cyclopropyl,
- R.sub.2 and R.sub.3 are independently hydrogen or methyl,
- R.sub.4 is hydrogen, and
- R.sub.5 is ##STR23## wherein:
- Z is cyano,
- Q and T are hydrogen, and
- W is oxygen.
(.alpha.-Cyano-m-phenoxybenzyl) 2-isopropyl-4-pentynoate.
(.alpha.-Cyano-m-phenoxybenzyl) 2-isopropyl-3-methyl-4-pentynoate.
2-Isopropyl-4-pentynoic acid.
2-Isopropyl-3-methyl-4-pentynoic acid.
An insecticidal and miticidal composition comprising an acceptable carrier and as the active toxicant an insecticidally or miticidally effective amount of a compound of the formula:
- ##STR24## wherein:
- R.sub.1 is:
- an alkyl or alkenyl group having no more than five carbon atoms, or
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms;
- R.sub.2 and R.sub.3 are independently:
- hydrogen, or
- an alkyl group having no more than three carbon atoms;
- R.sub.4 is:
- hydrogen,
- an alkyl or alkenyl group having no more than ten carbon atoms, or
- phenyl or phenyl substituted with alkyl, halogen, cyano, nitro, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or dialkylamino groups;
- and
- R.sub.5 is a member selected from the group consisting of:
- ##STR25## wherein:
- Z is:
- hydrogen,
- cyano,
- thioamido,
- an alkyl or haloalkyl group having no more than three carbon atoms,
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms, or
- an alkenyl, haloalkenyl, or alkynyl group having no more than five carbon atoms;
- Q and T are independently:
- hydrogen,
- cyano,
- nitro,
- halogen
- alkyl,
- haloalkyl,
- alkylthio,
- alkylsulfinyl,
- alkylsulfonyl,
- dialkylamino,
- acylamido,
- alkoxy,
- aryloxy,
- arylthio,
- arylsulfinyl, or
- arylsulfonyl,
- provided that neither Q or T includes more than three aliphatic carbon atoms or more than six aromatic carbon atoms;
- W is:
- oxygen,
- sulfur or its oxides, or
- methylene;
- and
- Y is:
- bromine or
- chlorine.
An insecticidal and miticidal composition comprising an acceptable carrier and as an active toxicant an insecticidally or miticidally effective amount of a compound of the formula:
- ##STR26## wherein:
- R.sub.1 is:
- ethyl, isopropyl or cyclopropyl;
- R.sub.2 and R.sub.3 are hydrogen or when
- either R.sub.2 or R.sub.3 is hydrogen then the other
- member of this pair is methyl;
- R.sub.4 is:
- hydrogen, and
- R.sub.5 is a member selected from the group consisting of:
- ##STR27## wherein:
- Z is:
- hydrogen,
- cyano,
- thioamido
- an alkyl or haloalkyl group having no more than three carbon atoms,
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms, or an alkenyl, haloalkenyl, or alkynyl group having no more than five carbona toms:
- Q and T are independently:
- hydrogen,
- cyano,
- nitro,
- halogen,
- alkyl,
- haloalkyl,
- alkylthio,
- alkylsulfinyl,
- alkylsulfonyl,
- dialkylamino,
- acylamido,
- alkoxy,
- aryloxy,
- arylthio,
- arylsulfinyl, or
- arylsulfonyl,
- provided that neither Q or T includes more than three aliphatic carbon atoms or more than six aromatic carbon atoms;
- W is:
- oxygen,
- sulfur or its oxides, or
- methylene;
- and
- Y is:
- bromine or
- chlorine.
An insecticidal and miticidal composition comprising an acceptable carrier and as the active toxicant an insecticidally or miticidally effective amount of a compound of the formula:
- ##STR29## wherein:
- R.sub.1 is ethyl, isopropyl or cyclopropyl,
- R.sub.2 and R.sub.3 are independently hydrogen or methyl,
- R.sub.4 is hydrogen, and
- R.sub.5 is ##STR30## wherein:
- Z is cyano,
- Q and T are hydrogen, and
- W is oxygen.
A method of controlling insects and mites which comprises subjecting them to an insecticidally or miticidally effective amount of a compound of the formula:
- ##STR31## wherein:
- R.sub.1 is:
- an alkyl or alkenyl group having no more than five carbon atoms, or
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms;
- R.sub.2 and R.sub.3 are independently:
- hydrogen, or
- an alkyl group having no more than three carbon atoms;
- R.sub.4 is:
- hydrogen,
- an alkyl or alkenyl group having no more than ten carbon atoms, or
- phenyl or phenyl substituted with alkyl, halogen, cyano, nitro, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or dialkylamino groups;
- and
- R.sub.5 is a member of the group consisting of:
- ##STR32## wherein:
- Z is:
- hydrogen,
- cyano,
- thioamido,
- an alkyl or haloalkyl group having no more than three carbon atoms,
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms, or
- an alkenyl, haloalkenyl, or alkynyl group having no more than five carbon atoms;
- Q and T are independently:
- hydrogen,
- cyano,
- nitro,
- halogen,
- alkyl,
- haloalkyl,
- alkylthio,
- alkylsulfinyl
- alkylsulfonyl
- dialkylamino,
- acylamido,
- alkoxy,
- aryloxy,
- arylthio,
- arylsulfinyl, or
- arylsulfonyl,
- provided that neither Q or T includes more than three aliphatic carbon atoms or more than six aromatic carbon atoms;
- W is:
- oxygen,
- sulfur or its oxides, or
- methylene;
- and
- Y is:
- bromine or
- chlorine,
A method of controlling insects and mites which comprises subjecting them to an insecticidally or miticidally effective amount of a compound of the formula:
- ##STR33## wherein:
- R.sub.1 is:
- ethyl, isopropyl or cyclopropyl;
- R.sub.2 and R.sub.3 are hydrogen or when
- either R.sub.2 or R.sub.3 is hydrogen then the other member of this pair is methyl;
- R.sub.4 is:
- hydrogen;
- and
- R.sub.5 is a member of the group consisting of:
- ##STR34## wherein:
- Z is:
- hydrogen,
- cyano,
- thioamido,
- an alkyl or haloalkyl group having no more than three carbon atoms,
- a cycloalkyl or cycloalkenyl group having no more than six carbon atoms, or
- an alkenyl, haloalkenyl, or alkynyl group having no more than five carbon atoms;
- Q and T are independently:
- hydrogen,
- cyano,
- nitro,
- halogen,
- alkyl,
- haloalkyl,
- alkylthio,
- alkylsulfinyl
- alkylsulfonyl
- dialkylamino,
- acylamido,
- alkoxy,
- aryloxy,
- arylthio,
- arylsulfinyl, or
- arylsulfonyl,
- provided that neither Q or T includes more than three aliphatic carbon atoms or more than six aromatic carbon atoms;
- W is:
- oxygen,
- sulfur or its oxides, or
- methylene;
- and
- Y is:
- bromine or chlorine.
A method of controlling insects and mites which comprises subjecting them to an insecticidally or miticidally effective amount of a compound of the formula:
- ##STR36## wherein:
- R.sub.1 is ethyl, isopropyl or cyclopropyl,
- R.sub.2 and R.sub.3 are independently hydrogen or methyl,
- R.sub.4 is hydrogen, and
- R.sub.5 is ##STR37## wherein:
- Z is cyano,
- Q and T are hydrogen, and
- W is oxygen.
Dependencies are inferred from the claim text.