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US 6,147,062 AGranted
Phosphoryl hydrazine insecticides
AssigneeRohm and Haas Company
InventorsRichard Martin Jacobson, Luong Tu Nguyen
Life of this patent
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Abstract
This invention relates to a new class of phosphoryl hydrazine compounds which are useful as insecticides, acaricides, anthelmintics, and nematocides, compositions containing the compounds, and methods for their use. This invention also relates to methods to produce such compounds.
Claims10
A compound of the formula:
- ##STR12## wherein:
- R1 is unsubstituted or substituted (C.sub.1 -C.sub.6) alkoxy wherein the substituents are independently one or more (C.sub.1 -C.sub.6) alkoxy, keto, carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- R2 is (C.sub.1 -C.sub.6) alkoxy, (C.sub.1 -C.sub.6) alkyl, or phenyl, each of which is unsubstituted or substituted with one or more (C.sub.1 -C.sub.6) alkoxy, keto, carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- G is (C.sub.3 -C.sub.6) secondary alkyl or (C.sub.4 -C.sub.6) tertiary alkyl, each of which is unsubstituted or substituted with one or more cyano, (C.sub.1 -C.sub.6) alkoxy, carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- B is (C.sub.1 -C.sub.6) haloalkyl;
- its enantiomers and stereoisomers;
- and agronomically acceptable salts thereof.
4 more elements
A method to prepare a compound of the formula:
- ##STR13## comprising the step of heating a compound of the formula:
- ##STR14## in the presence or absence of a solvent;
- wherein:
- X is O or S;
- R3 and R4 are independently (C.sub.1 -C.sub.6) alkoxy, phenyloxy;
- (C.sub.1 -C.sub.6) alkyl, phenyl;
- N-(C.sub.1 -C.sub.6)alkylamino;
- N,N-di(C.sub.1 -C.sub.6)alkylamino;
- N-phenylamino;
- N-phenyl-N-(C.sub.1 -C.sub.6)alkylamino;
- (C.sub.1 -C.sub.6)alkylthio;
- or phenylthio, each independently unsubstituted or substituted with one or more of (C.sub.1 -C.sub.6) alkoxy, halo, (C.sub.1 -C.sub.6)alkylthio, keto, carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- R5 is (C.sub.1 -C.sub.8) primary alkyl;
- (C.sub.3 -C.sub.8) secondary alkyl;
- or (C.sub.4 -C.sub.8) tertiary alkyl, each unsubstituted or substituted with one or more cyano, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio;
- halo;
- carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- and
- R6 is (C.sub.1 -C.sub.6)alkyl;
- phenyl;
- or (C.sub.1 -C.sub.6)alkoxy, each unsubstituted or substituted with one or more halo, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkylthio, nitro, cyano, or (C.sub.1 -C.sub.6)alkylcarbonyl.
18 more elements
A method to prepare a compound of the formula:
- ##STR15## comprising contacting a compound of the formula:
- ##STR16## with an acyl chloride of the formula:
- ##STR17## in the presence of a base;
- wherein:
- X is O or S;
- R3 and R4 are independently (C.sub.1 -C.sub.6) alkoxy, phenyloxy;
- (C.sub.1 -C.sub.6) alkyl, phenyl;
- N-(C.sub.1 -C.sub.6)alkylamino;
- N,N-di(C.sub.1 -C.sub.6)alkylamino;
- N-phenylamino;
- N-phenyl-N-(C.sub.1 -C.sub.6)alkylamino;
- (C.sub.1 -C.sub.6)alkylthio;
- or phenylthio, each independently unsubstituted or substituted with one or more (C.sub.1 -C.sub.6) alkoxy, halo, (C.sub.1 -C.sub.6)alkylthio, keto, carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- R5 is (C.sub.1 -C.sub.8) primary alkyl;
- (C.sub.3 -C.sub.8) secondary alkyl;
- or (C.sub.4 -C.sub.8) tertiary alkyl, each unsubstituted or substituted with one or more cyano, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio;
- halo;
- carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- and
- R6 is (C.sub.1 -C.sub.6)alkyl;
- phenyl;
- or (C.sub.1 -C.sub.6)alkoxy, each unsubstituted or substituted with one or more halo, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkylthio, nitro, cyano, or (C.sub.1 -C.sub.6)alkylcarbonyl.
19 more elements
A method to prepare a compound of the formula:
- ##STR18## comprising the steps of:
- a) contacting a compound of the formula:
- ##STR19## with an acyl chloride of the formula:
- ##STR20## in the presence of a base;
- to form a compound of the formula:
- ##STR21## and b) heating the compound of the formula:
- ##STR22## in the presence or absence of a solvent;
- wherein:
- X is O or S;
- R3 and R4 are independently (C.sub.1 -C.sub.6) alkoxy, phenyloxy;
- (C.sub.1 -C.sub.6) alkyl, phenyl;
- N-(C.sub.1 -C.sub.6)alkylamino;
- N,N-di(C.sub.1 -C.sub.6)alkylamino;
- N-phenylamino;
- N-phenyl-N-(C.sub.1 -C.sub.6)alkylamino;
- (C.sub.1 -C.sub.6)alkylthio;
- or phenylthio, each independently unsubstituted or substituted with one or more of (C.sub.1 -C.sub.6) alkoxy, halo, (C.sub.1 -C.sub.6)alkylthio, keto, carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- R5 is (C.sub.1 -C.sub.8) primary alkyl;
- (C.sub.3 -C.sub.8) secondary alkyl;
- or (C.sub.4 -C.sub.8) tertiary alkyl, each unsubstituted or substituted with one or more cyano, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio;
- halo;
- carbo(C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)acyl groups;
- and
- R6 is (C.sub.1 -C.sub.6)alkyl;
- phenyl;
- or (C.sub.1 -C.sub.6)alkoxy, each unsubstituted or substituted with one or more halo, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkylthio, nitro, cyano, or (C.sub.1 -C.sub.6)alkylcarbonyl.
23 more elements
Dependencies are inferred from the claim text.