Claims
- 1. 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.
- 2. The compound of claim 1 wherein R1 and R2 are independently (C.sub.1 -C.sub.2)alkoxy; G is (C.sub.4 -C.sub.6)tertiary alkyl, and B is halo(C.sub.1)alkyl.
- 3. The compound of claim 1 wherein R1 and R2 are identical and selected from methoxy and ethoxy, G is tertiary butyl, and B is dichloromethyl or trichloromethyl.
- 4. A composition comprising an insecticidally, acaricidally, or nematocidally effective amount of one or more compounds of claim 1 and an agronomically acceptable carrier or an anthelmintically effectively amount of one or more compounds of claim 1 and a pharmaceutically acceptable carrier.
- 5. A method for controlling a pest comprising applying to the pest or to the soil or to the foliage of plants to be freed from infestation by the pest, a pesticidally effective amount of one or more compounds of claim 1 and wherein the pest is selected from insects, acarids, and nematodes.
- 6. A method for controlling a helminth, comprising contacting the helminth with an effective amount of a compound of claim 1.
- 7. 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.
- 8. 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.
- 9. 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.
- 10. The method of claim 7, 8, or 9 wherein:
- X is S;
- R3 and R4 are independently (C.sub.1 -C.sub.6) alkoxy; (C.sub.1 -C.sub.6) alkyl, or phenyl, each independently 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;
- R5 is (C.sub.3 -C.sub.6) secondary alkyl or (C.sub.4 -C.sub.6) tertiary alkyl, each 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; and
- R6 is (C.sub.1 -C.sub.6) haloalkyl.
Parent Case Info
This application claims the benefit of U.S. Provisional Application No. 60/109,647, which was filed on Nov. 24, 1998.
US Referenced Citations (4)