2-Oximino-tetrahydro-1,4-thiazin-5-one compounds and pesticidal carbamate derivatives
AssigneeUnion Carbide Corporation
InventorJohn Apling Durden, Jr.
Life of this patent
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Abstract
2-Oximino-tetrahydro-1,4-thiazin-5-one compounds are useful as intermediates in the preparation of 2-carbamoyloximino-tetrahydro-1,4-thiazin-5-one carbamate compounds that exhibit outstanding pesticidal activity.
Claims46
A compound of the formula:
- ##STR8## wherein:
- R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are individually hydrogen or alkyl
- Z is hydrogen or ##STR9## wherein:
- R.sub.6 and R.sub.7 are individually hydrogen, alkenyl, alkynyl, phenylalkyl or either substituted or unsubstituted alkyl or phenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, nitro, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkysulfonyl, carbamonyl, alkylcarboamoyl, or dialkylcarbamoyl substitutes;
- or when R.sub.6 is other than hydrogen R.sub.7 may also be alkanoyl, trihalomethanesulfenyl, dialkylaminosulfenyl, morpholinosulfenyl, pyrrolidylsulfenyl, piperidylsulfenyl or either substituted or unsubstituted phenylsulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, nitro, cyano, alkoxy, alkyl, trihalomethyl, alkylthio, alkylsulfinyl or alkylsulfonyl substituents in any combinations;
- with the proviso that R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 substituents individually may not include more than eight aliphatic carbon atoms and R.sub.6 and R.sub.7 substituents individually may not include more than 18 carbon atoms.
2-[-O-(Methylcarbamoyl) oximino]-3,4-dimethyltetrahydro-1,4-thiazin-5-one.
2-[0-(N-Dimethylaminosulfenyl-N-methylcarbamoyl) oximinol)-3,3]-dimethyltetrahydro-1,4-thiazin-5-one.
2-[0-[N-(4'-Morpholinosulfenyl)-N-methylcarbamoyl ]oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-one.
2-[O-(Dimethylcarbamoyl) oximino]-3,3-dimethyltetrahydro-1,4-thiazin-5-one.
2-[0-(Methylcarbamoyl) oximino]-3-methyl tetrahydro-1,4-thiazin-5-one.
2-Oximino-3-methyltetrahydro-1,4-thiazin-5-one.
2-Oximino-3,3-dimethyltetrahydro-1,4-thiazin-5-one.
2-Oximino-3,4-dimethyltetrahydro-1,4-thiazin-5-one.
A miticidal and insecticidal composition comprising an acceptable carrier and as active toxicant a compound of the formula ##STR11## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are individually hydrogen or alkyl;
- R.sub.6 and R.sub.7 are individually hydrogen, alkenyl, alkynyl, phenylalkyl or either substituted or unsubstituted alkyl or phenyl wherein the permissible substitutents are one or more fluoro, chloro, bromo, nitro, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, carbamoyl, alkylcarbamoyl, or dialkylcarbamoyl substituents in any combination;
- or when R.sub.6 is other than hydrogen R.sub.7 may also be alkanoyl, trihalomethanesulfenyl, dialkylaminosulfenyl, morpholinosulfenyl, pyrrolidylsulfenyl, piperidylsulfenyl or either substituted or unsubstituted phenylsulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, nitro, cyano, alkoxy, alkyl, trihalomethyl, alkylthio, alkylsulfinyl or alkylsulfonyl substituents in any combination;
- with the proviso the R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 substituents individually may not include more than eigth aliphatic carbons atoms and R.sub.6 and R.sub.7 substituents individually may not include more than 18 carbon atoms.
A method of controlling insects and mites which comprises subjecting them to an insecticidally or miticidally effective amount of a compound of the formula:
- ##STR12## wherein:
- R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are individually hydrogen or alkyl;
- R.sub.6 and R.sub.7 are individually hydrogen, alkenyl, alkynyl, phenylalkyl or either substituted or unsubstituted alkyl or phenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, nitro, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, carbamoyl, alkylcarbamoyl, or dialkylcarbamoyl substituents in any combination ;
- or when R.sub.6 is other than hydrogen R.sub.7 may also be alkanoyl, trihalomethanesulfenyl, dialkylaminosulfenyl, morpholinosulfenyl, pyrrolidylsulfenyl, piperidylsulfenyl, or either substituted or unsubstituted phenylsulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, nitro, cyano, alkoxy, alkyl trihalomethyl, alkylthio, alkylsulfinyl or alkylsulfonyl substituents in any combination;
- with the proviso that R.sub.1, R.sub.2, R.sub.3 R.sub.4 and R.sub.5 substituents individually may not include more than eight aliphatic carbon atoms and R.sub.6 and R.sub.7 substituents individually may not include more than eighteen carbon atoms.
A method of preparing a compound of the formula ##STR13## which comprises reacting a compound of the formula:
- ##STR14## with a compound of the formula ##STR15## in the presence of an acid acceptor wherein:
- X is chlorine or fluorine;
- R.sub.1, r.sub.2, r.sub.3, r.sub.4 and R.sub.5 are individually hydrogen or alkyl;
- R.sub.6 and R.sub.7 are individually hydrogen alkenyl, alkynyl, phenylalkyl or either substituted or unsubstituted alkyl or phenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, nitro, cyano, alkyl, alkylthio, alkylsufinyl, alkylsulfonyl, carbamoyl, alkylcarbamoyl, or dialkylcarbamoyl substituents, or when R.sub.6 is other than hydrogen R.sub.7 may also be alkanoyl, trihalomethanesulfenyl, dialkylaminosulfenyl, morpholinosulfenyl, pyrrolidylsulfenyl, piperidylsulfenyl, or either substituted or unsubstituted phenylsulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, nitro, cyano, alkoxy, alkyl, trihalomethyl, alkylthio, alkylsulfinyl or alkylsulfonyl substituents in any combination;
- with the proviso that R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 substituents individually may not include more than eight aliphatic carbon atoms and R.sub.6 and R.sub.7 substituents individually may not include more than eighteen carbon atoms.
A method of preparing a compound of the formula:
- ##STR16## which compound of the formula:
- ##STR17## with an appropriately substituted amine compound of the formula:
- H.sub.2 NR.sub.1
- wherein:
- Y is nitro, methylsulfonyl or any other appropriate leaving group;
- R.sub.1, r.sub.2, r.sub.3, r.sub.4 and R.sub.5 are individually hydrogen or alkyl;
- R.sub.8 is alkyl;
- with the proviso that R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.8 substituents individually may not include more than light aliphatic carbon atoms.
Dependencies are inferred from the claim text.