Hydroxyarylalkyleneaminoaryl carbamates and derivatives thereof useful as insecticidal compositions
AssigneeUnion Carbide Corporation
InventorCharles A. Wilson, II
Life of this patent
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Abstract
This invention relates to novel hydroxyarylalkyleneaminoaryl carbamate compounds and derivatives thereof and to their preparation. This invention is also directed to insecticidal compositions comprising an acceptable carrier and an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention as well as to a method of controlling insects by subjecting them to an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention.
Claims90
A compound of the formula:
- ##STR31## wherein R and R.sup.1 are individually hydrogen or alkyl;
- R.sup.2 is hydrogen, halo, alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy provided that when R.sup.1 and R.sup.2 are individually alkyl or alkoxy and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic;
- R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio provided that when R.sup.3 and R.sup.4 are individually alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl and provided further than when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic;
- and R.sup.5 and R.sup.6 are individually hydrogen or alkyl provided that when R.sup.5 is alkyl, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl hydroxyarylalkyleneaminoaryloxycarbonylaminosulphenyl, hydroxy arylalklyleneamino-aryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination;
- and metal salts thereof.
4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate.
4-(2-Hydroxy-5-methoxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate.
4-(2-Hydroxybenzylideneamino)-3-isopropylphenyl methylcarbamate.
4-(3,5-Dibromo-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate.
4-(5-Chloro-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate.
4-(2-Hydroxy-5-nitrobenzylideneamino)-3,5-dimethylphenyl methylcarbamate.
Di[4-(2-hydro xybenzylideneamino)-3,5-dimethylphenyl]thiobis(methylcarbamate).
2,3-Dihydro-2,2-dimethyl-4-(2-hydroxybenzylideneamino)benzofuran-7-yl methylcarbamate.
4-[2-Hydroxy-4-(methylcarbamoyloxy)benzylideneamino]-3,5-dimethylphenyl methylcarbamate.
4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl N-(4-tert-butylphenylsulfenyl)-N-methylcarbamate.
4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate.
4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate, copper (II) salt.
An insecticidal composition comprising an acceptable carrier and as the active toxicant an insecticidally effective amount of a compound of the formula:
- ##STR32## wherein R and R.sup.1 are individually hydrogen or alkyl;
- R.sup.2 is hydrogen, halo, alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy provided that when R.sup.1 and R.sup.2 are individually alkyl or alkoxy and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five-membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic;
- R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio provided that when R.sup.3 and R.sup.4 are individually alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic;
- and R.sup.5 and R.sup.6 are individually hydrogen or alkyl provided that when R.sup.5 is alkyl, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination;
- and metal salts thereof.
A method of controlling insects which comprises subjecting them to an insecticidally effective amount of a compound of the formula:
- ##STR33## wherein R and R.sup.1 are individually hydrogen or alkyl;
- R.sup.2 is hydrogen, halo, alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy provided that when R.sup.1 and R.sup.2 are individually alkyl or alkoxy and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five-membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that then the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic;
- R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio provided that when R.sup.3 and R.sup.4 are individually alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five-membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic;
- and R.sup.5 and R.sup.6 are individually hydrogen or alkyl provided that when R.sup.5 is alkyl, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, cholor, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination;
- and metal salts thereof.
Dependencies are inferred from the claim text.