Claims
- 1. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound having the formula ##STR13## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m -- wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;
- R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl;
- R.sup.2 is hydrogen or C.sub.1 -C.sub.2 alkyl; and
- R.sup.3 and R.sup.4 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined and their salts.
- 2. The method of claim 1 wherein R is chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl, or methylsulfonyl; R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; R.sup.3 and R.sup.4 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; or (13) --N--(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined.
- 3. The method of claim 1 wherein R.sup.3 and R.sup.4 are independently are hydrogen; chlorine; fluorine; bromine; methyl; C.sub.1 -C.sub.4 alkoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R.sup.b SO.sub.n -- wherein n is the integer 0 or 2 and R.sup.b is methyl, chloromethyl, trifluoromethyl, ethyl, or n-propyl; R.sup.e C(O)-- where R.sup.e is C.sub.1 -C.sub.4 alkyl; or SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined and R.sup.3 is in the 3-position and R.sup.4 is in the 4-position.
- 4. The method of claim 2 wherein R.sup.3 is hydrogen and R.sup.4 is hydrogen, chlorine, bromine, fluorine, cyano, trifluoromethyl or R.sup.b SO.sub.2 wherein R.sup.b is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.
- 5. The methodof claim 2 wherein R is chlorine; R.sup.1 is methyl; R.sup.2 is methyl; R.sup.3 is 3-n-C.sub.3 H.sub.7 O; and R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2.
- 6. The method of claim 2 wherein R is chlorine; R.sup.1 is methyl; R.sup.2 is methyl; R.sup.3 is 3-C.sub.2 H.sub.5 S; and R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2.
- 7. The method of claim 1 wherein R.sup.3 is hydrogen.
- 8. The method of claim 3 wherein R.sup.3 is hydrogen.
- 9. An herbicidal composition comprising a 5-(2-substituted benzoyl)-barbituric acid compound of the formula ##STR14## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m -- wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;
- R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl;
- R.sup.2 is hydrogen or C.sub.1 -C.sub.2 alkyl; and
- R.sup.3 and R.sup.4 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined or a salt thereof and an inert carrier therefor with the proviso that when R is chlorine, R1 is methyl and R2 is methyl then R3 and R4 can not both be hydrogen.
- 10. The composition of claim 9 wherein R is chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl or methylsulfonyl; R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; and R.sup.3 and R.sup.4 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)-- wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; or (13) --N--(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.d are as defined.
- 11. The composition of claim 9 wherein R.sup.3 and R.sup.4 are independently are hydrogen; chlorine; fluorine; bromine; methyl; C.sub.1 -C.sub.4 methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R.sup.b SO.sub.n -- wherein n is the integer 0 or 2 and R.sup.b is methyl, chloromethyl, trifluoromethyl, ethyl, or n-propyl; R.sup.e C(O)-- where R.sup.e is C.sub.1 -C.sub.4 alkyl; or SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined and R.sup.3 is in the 3-position and R.sup.4 is in the 4-position.
- 12. The composition of claim 9 wherein R.sup.3 is hydrogen and R.sup.4 is hydrogen, chlorine, bromine, fluorine, cyano, trifluoromethyl or R.sup.b SO.sub.2 wherein R.sup.b is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.
- 13. The composition of claim 9 wherein R is chlorine; R.sup.1 is methyl; R.sup.2 is methyl; R.sup.3 is 3-n-C.sub.3 H.sub.7 O; and R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2.
- 14. The composition of claim 9 wherein R is chlorine; R.sup.1 is methyl; R.sup.2 is methyl; R.sup.3 is 3-C.sub.2 H.sub.5 S; and R.sup.4 is 4-C.sub.2 H.sub.5 SO.sub.2.
- 15. The composition of claim 9 wherein R.sup.3 is hydrogen.
- 16. The composition of claim 10 wherein R.sup.3 is hydrogen.
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of application Ser. No. 872,068, filed June 9, 1986 now abandoned.
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3828043 |
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3999974 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
872068 |
Jun 1986 |
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