Claims
- 1. A soil application insecticidal compound of the formula: ##STR10## wherein R.sup.1 selected from the group consisting of (C.sub.1 -C.sub.4) alkyl which has no branching on the carbon adjacent to the oxygen, (C.sub.3 -C.sub.8) alkenyl or (C.sub.3 -C.sub.8) alkynyl wherein these substituents may be substituted with one or more halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (C.sub.1 -C.sub.6) alkoxy, carbo (C.sub.1 -C.sub.6) alkoxy, or (C.sub.1 -C.sub.6) acyl groups;
- Y is oxygen or sulfur; and
- X.sup.2, X.sup.3 and X.sup.4 are independently sulfur, or oxygen; and
- R.sup.2 and R.sup.3 are independently selected from the group consisting of (C.sub.1 -C.sub.10) alkyl, (C.sub.3 -C.sub.10) alkenyl, (C.sub.3 -C.sub.10) alkynyl, (C.sub.3 -C.sub.10) cycloalkyl, (C.sub.3 -C.sub.10) cycloalkyl (C.sub.1 -C.sub.6) alkyl, and (C.sub.1 -C.sub.4) phenalkyl wherein those substituents may be substituted with one or more (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) haloalkyl, halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (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
- R.sup.4 is unsubstituted (C.sub.4 -C.sub.10) branched chain alkyl or substituted (C.sub.4 -C.sub.10) branched chain alkyl wherein the substituents are independently selected from one or more (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) haloalkyl, halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (C.sub.1 -C.sub.6) alkoxy, carbo (C.sub.1 -C.sub.6) alkoxy, or (C.sub.1 -C.sub.6) acyl groups;
- with the proviso that only one of R.sup.2 and R.sup.3 may be a cycloalkyl group; and
- with the proviso that if Y is sulfur and
- R.sup.1 and R.sup.2 are identical, X.sup.2 is oxygen, X.sup.3 and X.sup.4 are identical, and R.sup.3 and R.sup.4 are identical; or
- X.sup.2 and X.sup.4 are identical, R.sup.2 and R.sup.4 are identical, X.sup.3 is oxygen and R.sup.1 and R.sup.3 are identical; or
- X.sup.4 is oxygen, R.sup.1 and R.sup.4 are identical, X.sup.2 and X.sup.3 are identical, and R.sup.1 and R.sup.3 are identical;
- then at lease one of R.sup.1, R.sup.2, R.sup.3 or R.sup.4 must be a group other than (C.sub.1 -C.sub.4) alkyl; and
- with the further proviso that the combination R.sup.1 and R.sup.2 is not identical to the combination R.sup.3 and R.sup.4.
- 2. The compound of claim 1 wherein R.sup.1 is selected from substituted or unsubstituted (C.sub.1 -C.sub.4) alkyl which has no branching at the carbon adjacent to the oxygen atom and wherein the alkyl group may be substituted with from one to six halogen atoms; Y is sulfur or oxygen; X.sup.2 and X.sup.3 are oxygen; X.sup.4 is oxygen or sulfur; R.sup.2, R.sup.3 and R.sup.4 are independently selected from optionally substituted (C.sub.1 -C.sub.6) alkyl or optionally substituted (C.sub.3 -C.sub.6) alkenyl wherein the substituent may be from one to six halogen atoms.
- 3. The compound of claim 1 wherein R.sup.1 is (C.sub.1 -C.sub.4) alkyl wherein said alkyl is not branched on the carbon adjacent to the oxygen atom; R.sup.2 is substituted or unsubstituted (C.sub.1 -C.sub.5) alkyl wherein the substituent may be from three to six fluorine atoms; R.sup.3 is (C.sub.1 -C.sub.5) alkyl; R.sup.4 is substituted or unsubstituted (C.sub.1 -C.sub.5) alkyl wherein the substituent may be from three to six fluorine atoms; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 4. The compound of claim 1 wherein R.sup.1 is (C.sub.1 -C.sub.3) unbranched alkyl; R.sup.2 is (C.sub.1 -C.sub.5) alkyl; R.sup.3 is (C.sub.2 -C.sub.5) alkyl; R.sup.4 is (C.sub.4 -C.sub.5) alkyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 5. The compound of claim 4 wherein R.sup.1, R.sup.2 and R.sup.3 are ethyl; R.sup.4 is isobutyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 6. The compound of claim 4 wherein R.sup.1 and R.sup.2 are propyl; R.sup.3 is ethyl; R.sup.4 is isobutyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 7. The compound of claim 4 wherein R.sup.1 and R.sup.2 are propyl; R.sup.3 is ethyl; R.sup.4 is secbutyl X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 8. The compound of claim 4 wherein R.sup.1, R.sup.2 and R.sup.3 are ethyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 9. The compound of claim 4 wherein R.sup.1 and R.sup.2 are propyl; R.sup.3 is ethyl and R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 10. The compound of claim 4 wherein R.sup.1 and R.sup.3 are ethyl; R.sup.2 is propyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 11. The compound of claim 4 wherein R.sup.1 and R.sup.3 are ethyl; R.sup.2 is isopropyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 12. The compound of claim 4 wherein R.sup.1 and R.sup.3 are ethyl; R.sup.2 is secbutyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen and Y is sulfur.
- 13. The compound of claim 3 wherein R.sup.1 is ethyl; R.sup.2, R.sup.3 and R.sup.4 are 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen and Y is sulfur.
- 14. A method of controlling corn rootworm, comprising applying to said corn rootworm soil habitat a pesticidally-effective amount of a compound of the formula ##STR11## wherein R.sup.1 is selected from the group consisting of (C.sub.1 -C.sub.4) alkyl which has no branching on the carbon adjacent to the oxygen atom, (C.sub.3 -C.sub.8) alkenyl or (C.sub.3 -C.sub.8) alkynyl wherein these substituents may be substituted with one or more halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (C.sub.1 -C.sub.6) alkoxy, carbo (C.sub.1 -C.sub.6) alkoxy, or (C.sub.1 -C.sub.6) acyl groups;
- Y, X.sup.2, X.sup.3 and X.sup.4 are independently sulfur or oxygen; and
- R.sup.2 and R.sup.3 are independently selected from the group consisting of (C.sub.1 -C.sub.10) alkyl, (C.sub.3 -C.sub.10) alkenyl, (C.sub.3 -C.sub.10) alkynyl, (C.sub.3 -C.sub.10) cycloalkyl, (C.sub.3 -C.sub.10) cycloalkyl (C.sub.1 -C.sub.6) alkyl, and (C.sub.1 -C.sub.4) phenalkyl wherein these substituents may be substituted by one or more (C.sub.1 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.6) alkyl, halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (C.sub.1 -C.sub.6) alkoxy, carbo (C.sub.1 -C.sub.6) alkoxy or (C.sub.1 -C.sub.6) acyl groups;
- R.sup.4 is unsubstituted (C.sub.4 -C.sub.10) branched chain alkyl or substituted (C.sub.4 -C.sub.10) branched chain alkyl wherein the substituents are independently selected from one or more (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) haloalkyl, halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (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
- with the proviso that only one of R.sup.2 and R.sup.3 may be cycloalkyl; and
- with the proviso that if Y is sulfur and
- R.sup.1 and R.sup.2 are identical, X.sup.2 is oxygen, X.sup.3 and X.sup.4 are identical and R.sup.3 and R.sup.4 are identical; or
- X.sup.2 and X.sup.4 are identical, X.sup.2 and X.sup.3 are identical, R.sup.2 is oxygen and R.sup.1 and R.sup.3 are identical; or
- X.sup.4 is oxygen; R.sup.1 and R.sup.4 are identical, X.sup.2 and X.sup.3 are identical, and R.sup.2 and R.sup.3 are identical;
- then at least one of R.sup.1, R.sup.2, R.sup.3 or R.sup.4 must be a group other than (C.sub.1 -C.sub.4) alkyl; and
- with the further proviso that the combination R.sup.1 and R.sup.2 is not identical to the combination R.sup.3 and R.sup.4.
- 15. The method of claim 14 wherein R.sup.1 is selected from substituted or unsubstituted (C.sub.1 -C.sub.4) alkyl which has no branching on the carbon adjacent to the oxygen atom and wherein the substituent may be from one to six halogen atoms; Y is sulfur or oxygen; X.sup.2 and X.sup.3 are oxygen; X.sup.4 is oxygen or sulfur; R.sup.2, R.sup.3 and R.sup.4 are independently selected from substituted or unsubstituted (C.sub.1 -C.sub.6) alkyl or (C.sub.3 -C.sub.6) alkenyl wherein the substituent may be from one to six halogen atoms.
- 16. The method of claim 14 wherein R.sup.1 is (C.sub.1 -C.sub.4) alkyl wherein said alkyl is unbranched at the carbon atom adjacent to the oxygen atom; R.sup.2 is substituted or unsubstituted (C.sub.1 -C.sub.5) alkyl wherein the substituent may be from three to six fluorine atoms; R.sup.3 is (C.sub.1 -C.sub.4) alkyl; R.sup.4 is substituted or unsubstituted (C.sub.1 -C.sub.5) alkyl wherein the substituent may be from three to six fluorine atoms; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 17. The method of claim 14 wherein R.sup.1 is (C.sub.1 -C.sub.3) unbranched alkyl; R.sup.2 is (C.sub.1 -C.sub.5) alkyl; R.sup.3 is (C.sub.2 -C.sub.5) alkyl; R.sup.4 is (C.sub.4 -C.sub.5) alkyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 18. The method of claim 14 wherein R.sup.1, R.sup.2 and R.sup.3 are ethyl; R.sup.4 is isobutyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 19. The method of claim 14 wherein R.sup.1 and R.sup.2 are propyl; R.sup.3 is ethyl; R.sup.4 is isobutyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 20. The method of claim 14 wherein R.sup.1 and R.sup.2 are propyl; R.sup.3 is ethyl; R.sup.4 is secbutyl X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 21. The method of claim 14 wherein R.sup.1, R.sup.2 and R.sup.3 are ethyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 22. The method of claim 14 wherein R.sup.1 and R.sup.2 are propyl; R.sup.3 is ethyl and R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 23. The method of claim 14 wherein R.sup.1 and R.sup.2 are ethyl; R.sup.3 is propyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 24. The method of claim 14 wherein R.sup.1 and R.sup.3 are ethyl; R.sup.2 is isopropyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen; and Y is sulfur.
- 25. The method of claim 14 wherein R.sup.1 and R.sup.3 are ethyl; R.sup.2 is secbutyl; R.sup.4 is 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen and Y is sulfur.
- 26. The method according to claim 14 wherein R.sup.1 is ethyl; R.sup.2, R.sup.3 and R.sup.4 are 2,2-dimethylpropyl; X.sup.2, X.sup.3 and X.sup.4 are oxygen and Y is sulfur.
- 27. A method of controlling soil insects, comprising applying to said insect habitat a pesticidally-effective amount of a compound of the formula ##STR12## wherein R.sup.1 is selected from the group consisting of (C.sub.1 -C.sub.4) alkyl which has no branching on the carbon adjacent to the oxygen atom, (C.sub.3 -C.sub.8) alkenyl or (C.sub.3 -C.sub.8) alkynyl wherein these substituents may be substituted with one or more halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (C.sub.1 -C.sub.6) alkoxy, carbo (C.sub.1 -C.sub.6) alkoxy, or (C.sub.1 -C.sub.6) acyl groups;
- Y, X.sup.2, X.sup.3 and X.sup.4 are independently sulfur or oxygen; and
- R.sup.2 and R.sup.3 are independently selected from the group consisting of (C.sub.1 -C.sub.10) alkyl, (C.sub.3 -C.sub.10) alkenyl, (C.sub.3 -C.sub.10) alkynyl, (C.sub.3 -C.sub.10) cycloalkyl, (C.sub.3 -C.sub.10) cycloalkyl (C.sub.1 -C.sub.6) alkyl, and (C.sub.1 -C.sub.4) phenalkyl wherein these substituents may be substituted by one or more (C.sub.1 -C.sub.6) alkyl, halo (C.sub.1 -C.sub.6) alkyl, halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (C.sub.1 -C.sub.6) alkoxy, carbo (C.sub.1 -C.sub.6) alkoxy or (C.sub.1 -C.sub.6) acyl groups;
- R.sup.4 is unsubstituted (C.sub.4 -C.sub.10) branched chain alkyl or substituted. (C.sub.4 -C.sub.10) branched chain alkyl wherein the substituents are independently selected from one or more (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) haloalkyl, halogen, cyano, (C.sub.1 -C.sub.6) alkoxy, halo (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
- with the proviso that only one of R.sup.2 and R.sup.3 may be cycloalkyl; and
- with the proviso that if Y is sulfur and
- R.sup.1 and R.sup.2 are identical), X.sup.2 is oxygen, X.sup.3 and X.sup.4 are identical, and R.sup.3 and R.sup.4 are identical; or
- X.sup.2 and X.sup.4 are identical, R.sup.2 and R.sup.4 are identical, X.sup.3 is oxygen and R.sup.1 and R.sup.3 are identical; or
- X.sup.4 is oxygen, R.sup.1 and R.sup.4 are identical, X.sup.2 and X.sup.3 are identical, and R.sup.2 and R.sup.3 are identical;
- then at least one of R.sup.1, R.sup.2, R.sup.3 or R.sup.4 must be a group other than (C.sub.1 -C.sub.4) alkyl; and
- with the further proviso that fire combination R.sup.1 and R.sup.2 is not identical to the combination R.sup.3 and R.sup.4.
Parent Case Info
This Application is a continuation of Ser. No. 07/866,084 filed Apr. 3, 1992, now abandoned which was a continuation of Ser. No. 07/463,746 filed Jan. 12, 1990, now abandoned.
US Referenced Citations (4)
Continuations (2)
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Number |
Date |
Country |
Parent |
866084 |
Apr 1992 |
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Parent |
463746 |
Jan 1990 |
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