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US 4,303,669 AGranted
Hybrid 1,3-dione-carbamate compounds
AssigneeUnion Carbide Corporation
InventorThemistocles D. J. D'Silva
Life of this patent
Estimating the term…
Abstract
Novel hybrid 1,3-dione-carbamate compounds which exhibit utility as insecticides and acaricides. Also included are insecticidal and acaricidal compositions containing these compounds and a method of controlling insects and acarids.
Claims48
Compounds of the formula:
- ##STR54## wherein:
- m=0 or 1;
- n=1 or 2;
- R, R.sub.1, R.sub.2, and R.sub.3 are individually hydrogen or alkyl groups of one to four carbon atoms;
- R.sub.4 is:
- (a) fluorocarbonyl or
- (b) a group of the formula:
- ##STR55## wherein R, R.sub.1, R.sub.2, R.sub.3 and m have the above indicated values;
- ##STR56## wherein R.sub.5 is:
- (1) a phenyl group which is unsubstituted or substituted with one or more C.sub.1 -C.sub.12 alkyl, chloro, fluoro, bromo, alkoxy, alkylthio, alkylthioalkyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, alkylsulfonylalkyl, alkynyloxy, dialkylamino, alkoxyamino, formamidino, cyano, dioxolanyl or dithiolanyl group in any combination;
- or
- (2) a naphthyl, tetrahydronaphthyl, dihydrobenzofuranyl, benzodioxalanyl, or benzothienyl group, all of which is unsubstituted or substituted with one or more alkyl groups;
- or
- (3) a group of the formula:
- ##STR57## wherein R.sub.6 is a chloro, alkyl, alkylthio, cyanoalkylthio, amidoalkylthio or cyano group;
- or R.sub.6 is hydrogen provided R.sub.7 is not hydrogen;
- R.sub.7 is an alkyl, alkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthioalkyl, cyanoalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxyalkyl, nitroalkyl, hydroxyalkyl, or phenyl group, said phenyl group is unsubstituted or substituted with one or more alkyl, chloro, or fluoro groups in any combination;
- or R.sub.7 is hydrogen, provided R.sub.6 is not hydrogen;
- or
- (4) cyclic oximes selected from the group consisting of 2-oximino-1,4-dithianes, 2-oximino-1,3-dithianes, 4-oximino-1,3-dithiolanes, 2-oximino-1,4-dioxanes, 2-oximino-tetrahydro-1,4-thiazine-3-ones, 2-oximino-1,3-dihiolanes, 2-imino-4-oximino-1,3-dithiolanes, 3-oximinothiophanes, 2-oximinothiophanes, 2-oximino-tetrahydro-1,4-oxazine-3-ones, 2-oximino-1,4-oxathianes, 4-oximino-1,3-oxathiolanes, 2-oximino-thiazolidin-3-ones, 2-oximino-1,3-thiazolidin-4-ones or 2-oximino-tetrahydro-1,4-thiazin-5-ones, each of which is unsubstituted or substituted with one to four alkyl groups and wherein sulfur can be in any of its oxidation states.
17 more elements
Compounds of the formula:
- ##STR58## wherein:
- n=1 or 2;
- R, R.sub.1 and R.sub.2 are individually hydrogen or alkyl groups of one to four carbon atoms;
- R.sub.3 is hydrogen;
- R.sub.4 is:
- (a) fluorocarbonyl or
- (b) a group of the formula:
- ##STR59## wherein R, R.sub.1, R.sub.2, and R.sub.3 have the above indicated values;
- ##STR60## wherein R.sub.5 is:
- (1) a phenyl group which is unsubstituted or substituted with one or more C.sub.1 -C.sub.12 alkyl, chloro, fluoro, bromo, alkoxy, alkylthio, alkylthioalkyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, alkylsulfonylalkyl, alkynyloxy, dialkylamino, alkoxyamino, formamidino, cyano, dioxolanyl or dithiolanyl group in any combination;
- or
- (2) a naphthyl, tetrahydronaphthyl, dihydrobenzofuranyl, benzodioxolanyl, or benzothienyl group, all of which is unsubstituted or substituted with one or more alkyl groups;
- or
- (3) a group of the formula:
- ##STR61## wherein R.sub.6 is a chloro, alkyl, alkylthio, cyanoalkylthio, amidoalkylthio or cyano group;
- or R.sub.6 is hydrogen provided R.sub.7 is not hydrogen;
- R.sub.7 is an alkyl, alkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthioalkyl, cyanoalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxyalkyl, nitroalkyl, hydroxyalkyl, or phenyl group, said phenyl group is unsubstituted or substituted with one or more alkyl, chloro, or fluoro groups in any combination;
- or R.sub.7 is hydrogen, provided R.sub.6 is not hydrogen;
- or
- (4) cyclic oximes selected from the group consisting of 2-oximino-1,4-dithianes, 2-oximino-1,3-dithianes, 4-oximino-1,3-dithiolanes, 2-oximino-1,4-dioxanes, 2-oximino-tetrahydro-1,4-thiazine-3-ones, 2-oximino-1,3-dithiolanes, 2-imino-4-oximino-1,3-dithiolanes, 3-oximinothiophanes, 2-oximinothiophanes, 2-oximinotetrahydro-1,4-oxazine-3-ones, 2-oximino-1,4-oxathianes, 4-oximino-1,3-oxathiolanes, 2-oximino-thiazolidin-3-ones, 2-oximino-1,3-thiazolidin-4-ones or 2-oximino-tetrahydro-1,4-thiazin-5-ones, each of which is unsubstituted or substituted with one to four groups and wherein sulfur can be in any of its oxidation states.
17 more elements
1-[N-Methyl-N-[N'-methyl-N'-fluorocarbonylaminosulfenyl] carbamoyloxy]-2-(2'-methylphenyl)-5,5-dimethyl-1-cyclohexene-3-one.
1-[N-Methyl-N-[N'-methyl-N'-fluorocarbonylaminosulfenyl]carbamoy loxy]-2-(2',4'-dimethylphenyl)-5,5-dimethyl-1-cyclohexene-3-one.
S-Methyl-N-[N'-[N"-methyl-N"-[1-(2-(2',4'-dimethylphenyl)-5, 5-dimethyl-1-cyclohexenyl-3-one) oxycarbonyl]aminosulfenyl]-N'-methylcarbamoyloxy] acetimidate.
1-[N-methyl-N-[N'-methyl-N'-[1-(2-(2'-methylphenyl)-5,5-dim ethyl-3-oxo-1-cyclohexenyl) oxycarbonyl] aminosulfenyl] carbamoyloxy] naphthalene.
7-[N-meth yl-N-[N'-methyl-N'-[1-(2-(2',4'-dimethylphenyl)-5,5-dimethyl-3-oxo-1-cycloh exenyl) oxycarbonyl] aminosulfenyl] carbamoyloxy]-2,2-dimethyl-2,3-dihydrobenzofuran.
4-[N-methyl-N-[N'-methyl-N'-[1-(2-(2',4'-dimet hylphenyl)-5,5-dimethyl-3-oxo-1-cyclohexenyl) oxycarbonyl] aminosulfenyl] carbamoyloxy]-2,2-dimethylbenzodioxolan.
S-Methyl-N-[N'-[N"-methyl-N"-[1-(2-(2 ',4'-dimethylphenyl)-5-isopropyl-1-cyclohexene-3-one) oxycarbonyl]aminosulfenyl]-N'-methylcarbamoyloxy] acetimidate.
An insecticidal and acaricidal composition comprising an acceptable carrier and as the active toxicant an insecticidally and acaricidally effective amount of a compound of the formula:
- ##STR62## wherein:
- m=0 or 1;
- n=1 or 2;
- R, R.sub.1, R.sub.2, and R.sub.3 are individually hydrogen or alkyl groups of one to four carbon atoms;
- R.sub.4 is:
- (a) fluorocarbonyl or
- (b) a group of the formula:
- ##STR63## wherein R, R.sub.1, R.sub.2, R.sub.3 and m have the above indicated values;
- ##STR64## wherein R.sub.5 is:
- (1) a phenyl group which is unsubstituted or substituted with one or more C.sub.1 -C.sub.12 alkyl, chloro, fluoro, bromo, alkoxy, alkylthio, alkylthioalkyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, alkylsulfonylalkyl, alkynyloxy, dialkylamino, alkoxyamino, formamidino, cyano, dioxolanyl or dithiolanyl group in any combination;
- or
- (2) a naphthyl, tetrahydronaphthyl, dihydrobenzofuranyl, benzodioxalanyl, or benzothienyl group, all of which is unsubstituted or substituted with one or more alkyl groups;
- or
- (3) a group of the formula:
- ##STR65## wherein R.sub.6 is a chloro, alkyl, alkylthio, cyanoalkylthio, amidoalkylthio or cyano group;
- or R.sub.6 is hydrogen provided R.sub.7 is not hydrogen;
- R.sub.7 is an alkyl, alkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthioalkyl, cyanoalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxyalkyl, nitroalkyl, hydroxyalkyl, or phenyl group, said phenyl group is unsubstituted or substituted with one or more alkyl, chloro, or fluoro groups in any combination;
- or R.sub.7 is hydrogen, provided R.sub.6 is not hydrogen;
- or
- (4) cyclic oximes selected from the group consisting of 2-oximino-1,4-dithianes, 2-oximino-1,3-dithianes, 4-oximino-1,3-dithiolanes, 2-oximino-1,4-dioxanes, 2-oximino-tetrahydro-1,4-thiazine-3-ones, 2-oximino-1,3-dithiolanes, 2-imino-4-oximino-1,3-dithiolanes, 3-oximinothiophanes, 2-oximinothiophanes, 2-oximinotetrahydro-1,4-oxazine-3-ones, 2-oximino-1,4-oxathianes, 4-oximino-1,3-oxathiolanes, 2-oximino-thiazolidin-3-ones, 2-oximino-1,3-thiazolidin-4-ones or 2-oximino-tetrahydro-1,4-thiazin-5-ones, each of which is unsubstituted or substituted with one to four alkyl groups and wherein sulfur can be in any of its oxidation states.
17 more elements
An insecticidal and acaricidal composition comprising an acceptable carrier and as the active toxicant an insecticidally and acaricidally effective amount of a compound of the formula:
- ##STR66## wherein:
- n=1 or 2;
- R, R.sub.1 and R.sub.2 are individually hydrogen or alkyl groups of one to four carbon atoms;
- R.sub.3 is hydrogen;
- R.sub.4 is:
- (a) fluorocarbonyl or
- (b) a group of the formula:
- ##STR67## wherein R, R.sub.1, R.sub.2, and R.sub.3 have the above indicated values:
- ##STR68## wherein R.sub.5 is:
- (1) a phenyl group which is unsubstituted or substituted with one or more C.sub.1 -C.sub.12 alkyl, chloro, fluoro, bromo, alkoxy, alkylthio, alkylthioalkyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, alkylsulfonylalkyl, alkynyloxy, dialkylamino, alkoxyamino, formamidino, cyano, dioxolanyl or dithiolanyl group in any combination;
- or
- (2) a naphthyl, tetrahydronaphthyl, dihydrobenzofuranyl, benzodioxalanyl, or benzothienyl group, all of which is unsubstituted or substituted with one or more alkyl groups;
- or
- (3) a group of the formula:
- ##STR69## wherein R.sub.6 is a chloro, alkyl, alkylthio, cyanoalkylthio, amidoalkylthio or cyano group;
- or R.sub.6 is hydrogen provided R.sub.7 is not hydrogen;
- R.sub.7 is an alkyl, alkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthioalkyl, cyanoalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxyalkyl, nitroalkyl, hydroxyalkyl, or phenyl group, said phenyl group is unsubstituted or substituted with one or more alkyl, chloro, or fluoro groups in any combination;
- or R.sub.7 is hydrogen, provided R.sub.6 is not hydrogen;
- or
- (4) cyclic oximes selected from the group consisting of 2-oximino-1,4-dithianes, 2-oximino-1,3-dithianes, 4-oximino-1,3-dithiolanes, 2-oximino-1,4-dioxanes, 2-oximino-tetrahydro-1,4-thiazine-3-ones, 2-oximino-1,3-dithiolanes, 2-imino-4-oximino-1,3-dithiolanes, 3-oximinothiophanes, 2-oximinothiophanes, 2-oximinotetrahydro-1,4-oxazine-3-ones, 2-oximino-1,4-oxathianes, 4-oximino-1,3-oxathiolanes, 2-oximino-thiazolidin-3-ones, 2-oximino-1,3-thiazolidin-4-ones or 2-oximino-tetrahydro-1,4-thiazin-5-ones, each of which is unsubstituted or substituted with one to four alkyl groups and wherein sulfur can be in any of its oxidation states.
17 more elements
A method of controlling insects and acarids which comprises subjecting them to an insecticidally and acaricidally effective amount of a compound of the formula:
- ##STR70## wherein:
- m=0 or 1;
- n=1 or 2;
- R, R.sub.1, R.sub.2, and R.sub.3 are individually hydrogen or alkyl groups of one to four carbon atoms;
- R.sub.4 is:
- (a) fluorocarbonyl or
- (b) a group of the formula:
- ##STR71## wherein R, R.sub.1, R.sub.2, R.sub.3 and m have the above indicated values;
- ##STR72## wherein R.sub.5 is:
- (1) a phenyl group which is unsubstituted or substituted with one or more C.sub.1 -C.sub.12 alkyl, chloro, fluoro, bromo, alkoxy, alkylthio, alkylthioalkyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, alkylsulfonylalkyl, alkynyloxy, dialkylamino, alkoxyamino, formamidino, cyano, dioxolanyl or dithiolanyl group in any combination;
- or
- (2) a naphthyl, tetrahydronaphthyl, dihydrobenzofuranyl, benzodioxalanyl, or benzothienyl group, all of which is unsubstituted or substituted with one or more alkyl groups;
- or
- (3) a group of the formula:
- ##STR73## wherein R.sub.6 is a chloro, alkyl, alkylthio, cyanoalkylthio, amidoalkylthio or cyano group;
- or R.sub.6 is hydrogen provided R.sub.7 is not hydrogen;
- R.sub.7 is an alkyl, alkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthioalkyl, cyanoalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxyalkyl, nitroalkyl, hydroxyalkyl, or phenyl group, said phenyl group is unsubstituted or substituted with one or more alkyl, chloro, or fluoro groups in any combination;
- or R.sub.7 is hydrogen, provided R.sub.6 is not hydrogen;
- or
- (4) cyclic oximes selected from the group consisting of 2-oximino-1,4-dithianes, 2-oximino-1,3-dithianes, 4-oximino-1,3-dithiolanes, 2-oximino-1,4-dioxanes, 2-oximino-tetrahydro-1,4-thiazine-3-ones, 2-oximino-1,3-dithiolanes, 2-imino-4-oximino-1,3-dithiolanes, 3-oximinothiophanes, 2-oximinothiophanes, 2-oximino-tetrahydro-1,4-oxazine-3-ones, 2-oximino-1,4-oxathianes, 4-oximino-1,3-oxathiolanes, 2-oximino-thiazolidin-3-ones, 2-oximino-1,3-thiazolidin-4-ones or 2-oximino-tetrahydro-1,4-thiazin-5-ones, each of which is unsubstituted or substituted with one to four alkyl groups and wherein sulfur can be in any of its oxidation states.
17 more elements
A method of controlling insects and acarids which comprises subjecting them to an insecticidally and acaricidally effective amount of a compound of the formula:
- ##STR74## wherein:
- n=1 or 2;
- R, R.sub.1 and R.sub.2 are individually hydrogen or alkyl groups of one to four carbon atoms;
- R.sub.3 is hydrogen;
- R.sub.4 is:
- (a) fluorocarbonyl or
- (b) a group of the formula:
- ##STR75## wherein R, R.sub.1, R.sub.2, and R.sub.3 have the above indicated values;
- ##STR76## wherein R.sub.5 is:
- (1) a phenyl group which is unsubstituted or substituted with one or more C.sub.1 -C.sub.12 alkyl, chloro, fluoro, bromo, alkoxy, alkylthio, alkylthioalkyl, alkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, alkylsulfonylalkyl, alkynyloxy, dialkylamino, alkoxyamino, formamidino, cyano, dioxolanyl or dithiolanyl group in any combination;
- or
- (2) a naphthyl, tetrahydronaphthyl, dihydrobenzofuranyl, benzodioxolanyl, or benzothienyl group, all of which is unsubstituted or substituted with one or more alkyl groups;
- or
- (3) a group of the formula:
- ##STR77## wherein R.sub.6 is a chloro, alkyl, alkylthio, cyanoalkylthio, amidoalkylthio or cyano group;
- or R.sub.6 is hydrogen provided R.sub.7 is not hydrogen;
- (3) R.sub.7 is an alkyl, alkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthioalkyl, cyanoalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxyalkyl, nitroalkyl, hydroxyalkyl, or phenyl group, said phenyl group is unsubstituted or substituted with one or more alkyl, chloro, or fluoro groups in any combination;
- or R.sub.7 is hydrogen, provided R.sub.6 is not hydrogen;
- or
- (4) cyclic oximes selected from the group consisting of 2-oximino-1,4-dithianes, 2-oximino-1,3-dithianes, 4-oximino-1,3-dithiolanes, 2-oximino-1,4-dioxanes, 2-oximino-tetrahydro-1,4-thiazine-3-ones, 2-oximino-1,3-dithiolanes, 2-imino-4-oximino-1,3-dithiolanes, 3-oximinothiophanes, 2-oximinothiophanes, 2-oximinotetrahydro-1,4-oxazine-3-ones, 2-oximino-1,4-oxathianes, 4-oximino-1,3-oxathiolanes, 2-oximino-thiazolidin-3-ones, 2-oximino-1,3-thiazolidin-4-ones or 2-oximino-tetrahydro-1,4-thiazin-5-ones, each of which is unsubstituted or substituted with one to four alkyl groups and wherein sulfur can be in any of its oxidation states.
17 more elements
Dependencies are inferred from the claim text.