Claims
- 1. An imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound of the formula ##STR36## wherein X and Z each, independently represents R, OR.sup.3, SR.sup.3, NR.sup.1 R.sup.2, F, Cl, Br, or CN;
- Y represents R, OR.sup.3, F, Cl, Br, or CN;
- W represents R, OR, SO.sub.n R.sup.3, NR.sup.1 R.sup.2, F, Cl, Br, NO.sub.2, CN, C(O)E, phenyl, phenoxy, or phenylthio, each phenyl, phenoxy and phenylthio optionally possessing 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- A represents F, Cl, Br, C(O)E, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, SOR.sup.3, or SO.sub.2 R.sup.3 ;
- B represents F, Cl, Br, CN, R, OR.sup.3, SR.sup.3, NR.sup.1 R.sup.2, phenyl, phenoxy, or phenylthio, each phenyl, phenoxy and phenylthio optionally possessing 1 to 3 substituents selected from the group consisting of F, Cl, Br, CN, CF.sub.3, NO.sub.2, and CH.sub.3 ;
- J and D each, independently represents R, F, Cl, Br, or C(O)E;
- R represents H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;
- R.sup.1 and R.sup.2 each, independently represents H or C.sub.1 -C.sub.4 alkyl;
- R.sup.3 represents C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;
- E represents R, OR, SR, NR.sup.1 R.sup.2, or phenyl;
- V represents H, C(O)R.sup.3, or benzyl;
- n represents an integer of 0, 1 or 2; and
- when V represents H, the agriculturally acceptable salts thereof.
- 2. A compound according to claim 1 wherein V represents H and agriculturally acceptable salts thereof.
- 3. A compound according to claim 1 wherein V represents benzyl.
- 4. A compound according to claim 1 wherein X and Z each, independently represents H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio.
- 5. A compound according to claim 1 wherein Y represents H, chloro, or C.sub.1 -C.sub.4 alkyl.
- 6. A compound according to claim 1 wherein W represents R, F, Cl, Br, NO.sub.2, CN, C(O) C.sub.1 -C.sub.4 alkyl, or CO.sub.2 C.sub.1 -C.sub.4 alkyl.
- 7. A compound according to claim 1 wherein A represents F, Cl, Br, NO.sub.2, C(O)E, or C.sub.1 -C.sub.4 haloalkyl.
- 8. A compound according to claim 1 wherein B represents F, Cl, Br, R, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio.
- 9. A compound according to claim 1 wherein J and D each, independently represents H or C.sub.1 -C.sub.4 alkyl.
- 10. A compound according to claim 2 wherein X and Z each, independently represents H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio;
- Y represents H, chloro, or C.sub.1 -C.sub.4 alkyl;
- W represents R, F, Cl, Br, NO.sub.2, CN, C(O) C.sub.1 -C.sub.4 alkyl, or CO.sub.2 C.sub.1 -C.sub.4 alkyl;
- A represents F, Cl, Br, NO.sub.2, C(O)E, or C.sub.1 -C.sub.4 haloalkyl;
- B represents F, Cl, Br, R, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio; and
- J and D each, independently represents H or C.sub.1 -C.sub.4 alkyl.
- 11. A compound according to claim 10 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; A and B each represents Cl; and J and D each represents H.
- 12. A compound according to claim 10 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Br; A and B each represents F; and J and D each represents H.
- 13. A compound according to claim 10 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents CN; A and B each represents F; and J and D each represents H.
- 14. A compound according to claim 10 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; A and B each represents F; and J and D each represents H.
- 15. A compound according to claim 10 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; A represents CF.sub.3 ; and B, J, and D each represents H.
- 16. A compound according to claim 10 wherein X represents OCH.sub.3 ; Y represents H; Z represents CH.sub.3 ; W represents Br; A and B each represents F; and J and D each represents H.
- 17. A compound according to claim 10 wherein X and Z each represents CH.sub.3 ; Y, W, J, and D each represents H; and A and B each represent F or Cl.
- 18. A composition useful as a herbicide comprising an imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound according to claim 2 and an agriculturally acceptable adjuvant or carrier.
- 19. A composition according to claim 18 wherein X and Z each, independently represents H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio.
- 20. A composition according to claim 18 wherein Y represents H, chloro, or C.sub.1 -C.sub.4 alkyl.
- 21. A composition according to claim 18 wherein W represents R.sup.3, F, Cl, Br, NO.sub.2, CN, C(O) C.sub.1 -C.sub.4 alkyl, or CO.sub.2 C.sub.1 -C.sub.4 alkyl.
- 22. A composition according to claim 18 wherein A represents F, Cl, Br, NO.sub.2, C(O)E, or C.sub.1 -C.sub.4 haloalkyl.
- 23. A composition according to claim 18 wherein B represents F, Cl, Br, R, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio.
- 24. A composition according to claim 18 wherein J and D each, independently represents H or C.sub.1 -C.sub.4 alkyl.
- 25. A composition according to claim 18 wherein
- X and Z each, independently represents H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio;
- Y represents H, chloro, or C.sub.1 -C.sub.4 alkyl;
- W represents R.sup.3, F, Cl, Br, NO.sub.2, CN, C(O) C.sub.1 -C.sub.4 alkyl, or CO.sub.2 C.sub.1 -C.sub.4 alkyl;
- A represents F, Cl, Br, NO.sub.2, C(O)E, or C.sub.1 -C.sub.4 haloalkyl;
- B represents F, Cl, Br, R, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio; and
- J and D each, independently represents H or C.sub.1 -C.sub.4 alkyl.
- 26. A composition according to claim 25 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; and A and B each represents Cl; and J and D each represents H.
- 27. A composition according to claim 25 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Br; A and B each represents F; and J and D each represents H.
- 28. A composition according to claim 25 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents CN; A and B each represents F; and J and D each represents H.
- 29. A composition according to claim 19 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; A and B each represents F; and J and D each represents H.
- 30. A composition according to claim 25 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; A represents CF.sub.3 ; and B, J, and D each represents H.
- 31. A composition according to claim 25 wherein X represents OCH.sub.3 ; Y represents H; Z represents CH.sub.3 ; W represents Br; A and B each represents F; and J and D each represents H.
- 32. A composition according to claim 18 comprising about 5 to about 98 percent of the imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound.
- 33. A composition according to claim 18 comprising about 0.001 to about 5 percent of the imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound.
- 34. A method of controlling unwanted vegetation which comprises applying to the vegetation or to the locus of the vegetation an herbicidally effective amount of an imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound according to claim 2.
- 35. A method according to claim 34 wherein the imidazolo[b 1,2-a]pyrimidine-2-sulfonanilide compound is applied post-emergence.
- 36. A method according to claim 34 wherein the imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound is applied pre-emergence.
- 37. A method according to claim 34 wherein X and Z each, independently represents H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio.
- 38. A method according to claim 34 wherein Y represents H, chloro, or C.sub.1 -C.sub.4 alkyl.
- 39. A method according to claim 34 wherein W represents R.sup.3, F, Cl, Br, NO.sub.2, CN, C(O) C.sub.1 -C.sub.4 alkyl, or CO.sub.2 C.sub.1 -C.sub.4 alkyl.
- 40. A method according to claim 34 wherein A represents F, Cl, Br, NO.sub.2, C(O)E, or C.sub.1 -C.sub.4 haloalkyl.
- 41. A method according to claim 34 wherein B represents F, Cl, Br, R, C.sub.1 -C.sub.4 alkylthio.
- 42. A method according to claim 34 wherein J and D each, independently represents H or C.sub.1 -C.sub.4 alkyl.
- 43. A method according to claim 34 wherein
- X and Z each, independently represents H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkylthio;
- Y represents H, chloro, or C.sub.1 -C.sub.4 alkyl;
- W represents R.sup.3, F, Cl, Br, NO.sub.2, CN, C(O) C.sub.1 -C.sub.4 alkyl, or CO.sub.2 C.sub.1 -C.sub.4 alkyl;
- A represents F, Cl, Br, NO.sub.2, C(O)E, or C.sub.1 -C.sub.4 haloalkyl;
- B represents F, Cl, Br, R, C.sub.1 -C.sub.4 alkoxy, or C.sub.1 -C.sub.4 alkythio; and
- J and D each, independently represents H or C.sub.1 -C.sub.4 alkyl.
- 44. A method according to claim 43 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; and A and B each represents Cl; and J and D each represents H.
- 45. A method according to claim 43 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Br; A and B each represents F; and J and D each represents H.
- 46. A method according to claim 43 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents CN; A and B each represents F; and J and D each represents H.
- 47. A method according to claim 43 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; A and B each represents F; and J and D each represents H.
- 48. A method according to claim 43 wherein X and Z each represents CH.sub.3 ; Y represents H; W represents Cl; A represents CF.sub.3 ; and B, J, and D each represents H.
- 49. A method according to claim 43 wherein X represents OCH.sub.3 ; Y represents H; Z represents CH.sub.3 ; W represents Br; A and B each represents F; and J and D each represents H.
- 50. A method of controlling unwanted vegetation in grassy crops which comprises applying to the vegetation or to the locus of the vegetation an herbicidally effective amount of a selectively herbicidal imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound of claim 2.
- 51. A method according to claim 50 wherein the grassy crop is wheat.
- 52. A method of controlling unwanted vegetation in grassy crops which comprises applying to the vegetation or to the locus of the vegetation an herbicidally effective amount of a selectively herbicidal imidazolo[1,2-a]pyrimidine-2-sulfonanilide compound of claim 10.
- 53. A method according to claim 52 wherein the grassy crop is wheat.
CROSS-REFERENCE TO RELATED APPLICATION
This is a divisional of application Ser. No. 45,908, filed May 1, 1987 now U.S. Pat. No. 4,731,446.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4349378 |
Cliff et al. |
Sep 1982 |
|
4605433 |
Pearson et al. |
Aug 1986 |
|
4755212 |
Kleschick et al. |
Jul 1988 |
|
Foreign Referenced Citations (3)
Number |
Date |
Country |
215382 |
Mar 1987 |
EPX |
951652 |
Mar 1964 |
GBX |
2149792 |
Jun 1985 |
GBX |
Non-Patent Literature Citations (4)
Entry |
Hunt, Chemical Abstracts, vol. 108, No. 112483 g (1988). |
Ekeley et al., J. Org. Chem. 52, pp. 2026-2028 (1930). |
Fajgelj et al., Heterocycles 24, pp. 379-386 (1986). |
Broadbent et al., J. Chem. Soc., pp. 3369-3372 (1965). |
Divisions (1)
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Number |
Date |
Country |
Parent |
45908 |
May 1987 |
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