Claims
- 1. A method for controlling the growth of undesired vegetation in plantation crops which comprises applying to the locus of the crop an herbicidally effective amount of a compound of Formula I ##STR24## wherein ##STR25## A is O or S; R.sup.1 is C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen, OR.sup.5, SR.sup.6 or CN; C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl, each optionally substituted with 1-3 halogen atoms; formyl; or C.sub.2 -C.sub.6 alkanoyl;
- R.sup.2 is H, allyl, propargyl, CH(CH.sub.3)C.tbd.CH, benzyl, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
- R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or N(CH.sub.3).sub.2 ;
- R.sup.5 and R.sup.6 are independently H or C.sub.1 -C.sub.3 alkyl;
- R.sup.7 and R.sup.8 are independently C.sub.1 -C.sub.2 alkyl;
- X is Cl or Br;
- Y is F or Cl;
- Z is H or may be taken together with R.sup.2 as --CH.sub.2 CHR.sup.9 such that the linking A atom is attached to the methine carbon;
- R.sup.9 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, vinyl, C.sub.2 alkynyl, CN, C(O)R.sup.10, CO.sub.2 R.sup.10, CONR.sup.10 R.sup.11, CR.sup.12 R.sup.13 C(O)R.sup.10, CR.sup.12 R.sup.13 CO.sub.2 R.sup.10, CR.sup.12 R.sup.13 CONR.sup.10 R.sup.11, CHR.sup.12 OH, CHR.sup.12 C(O)R.sup.10 or CHR.sup.12 OC(O)NR.sup.10 R.sup.11 ; and
- R.sup.10, R.sup.11, R.sup.12 and R.sup.13 are independently H or C.sub.1 -C.sub.3 alkyl.
- 2. The method of claim 1,
- wherein
- R.sup.1 is C.sub.1 -C.sub.3 alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C.sub.1 -C.sub.2 alkyl), S(C.sub.1 -C.sub.2 alkyl) or CN; C.sub.3 -C.sub.4 alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C.sub.3 -C.sub.4 alkynyl; or C.sub.2 -C.sub.3 alkanoyl;
- R.sup.2 is H, allyl, propargyl, CH(CH.sub.3)C.tbd.CH, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
- R.sup.3 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl or N(CH.sub.3).sub.2 ; and
- X is Cl.
- 3. The method of claim 2, wherein
- R.sup.1 is CH.sub.3 optionally substituted with 1 to 3 F atoms or Cl atoms; CH.sub.2 CN; allyl; or propargyl; and
- R.sup.3 is CF.sub.3.
- 4. The method of claim 2, wherein the compound of Formula I is
- 3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]-phenyl]-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H, 3H)-dione.
- 5. The method of claim 2, wherein the compound of Formula I is 3-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione.
- 6. The method of claim 1, wherein the compound of Formula I is applied in combination with at least one of the following: surfactant, solid or liquid diluent.
- 7. The method of claim 1 wherein the plantation crop is citrus.
- 8. A compound of Formula III ##STR26## wherein A is O or S;
- R.sup.1 is C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen, OR.sup.5, SR.sup.6 or CN; C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl, each optionally substituted with 1-3 halogen atoms; formyl; or C.sub.2 -C.sub.6 alkanoyl;
- R.sup.2 is H, allyl, propargyl, CH(CH.sub.3)C.tbd.CH, benzyl, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
- R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or N(CH.sub.3).sub.2 ;
- R.sup.5 and R.sup.6 are independently H or C.sub.1 -.sub.3 alkyl;
- R.sup.7 and R.sup.8 are independently C.sub.1 -C.sub.2 alkyl;
- X is Cl or Br;
- Y is F or Cl;
- Z is H or may be taken together with R.sup.2 as --CH.sub.2 CHR.sup.9 such that the linking A atom is attached to the methine carbon;
- R.sup.9 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, vinyl, C.sub.2 alkynyl, CN, C(O)R.sup.10, CO.sub.2 R.sup.10, CONR.sup.10 R.sup.11, CR.sup.12 R.sup.13 C(O)R.sup.10, CR.sup.12 R.sup.13 CO.sub.2 R.sup.10, CR.sup.12 R.sup.13 CONR.sup.10 R.sup.11, CHR.sup.12 OH, CHR.sup.12 OC(O)R.sup.10 or CHR.sup.12 OC(O)NR.sup.10 R.sup.11 ; and
- R.sup.10, R.sup.11, R.sup.12 and R.sup. 13 are independently H or C.sub.1 -C.sub.3 alkyl;
- provided that in compounds of Formula III, when R.sup.1 is C.sub.1 -C.sub.4 alkyl and R.sup.3 is CH.sub.3 or CF.sub.3 then R.sup.2 is benzyl or taken together with Z.
- 9. A compound of claim 8 wherein
- R.sup.1 is C.sub.1 -C.sub.3 alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C.sub.1 -C.sub.2 alkyl), S(C.sub.1 -C.sub.2 alkyl) or CN; C.sub.3 -C.sub.4 alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C.sub.3 -C.sub.4 alkynyl; or C.sub.2 -C.sub.3 alkanoyl;
- R.sup.2 is H, allyl, propargyl, CH(CH.sub.3)C.tbd.CH, CHR.sup.7 CO.sub.2 R.sup.8 or may be taken together with Z;
- R.sup.3 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl or N(CH.sub.3).sub.2 ; and
- X is Cl.
- 10. A compound of claim 9 wherein
- R.sup.1 is CH.sub.3 optionally substituted with 1 to 3 F atoms or Cl atoms; CH.sub.2 CN; allyl; or propargyl; and
- R.sup.3 is CF.sub.3.
- 11. A compound of claim 8 wherein the compound is
- 3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione; or
- 3-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4 (1H,3H)-dione.
- 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 8, 9 or 10, and at least one of the following: surfactant, solid or liquid diluent.
- 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 11, and at least one of the following: surfactant, solid or liquid diluent.
- 14. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a compound of claim 8, 9, or 10.
- 15. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a compound of claim 11.
- 16. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a composition of claim 12.
- 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a composition of claim 13.
CROSS-REFERENCE TO RELATED APPLICATION
This is a division of application Ser. No. 08/256,339, filed Jul. 13, 1994, which is a 371 of PCT/US92/11330, filed Dec. 30, 1992 and a continuation-in-part of application Ser. No. 07/821,118, filed Jan. 15, 1992, now abandoned.
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Divisions (1)
|
Number |
Date |
Country |
Parent |
256339 |
Jul 1994 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
821118 |
Jan 1992 |
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