Claims
- 1. A compound represented by the formula ##STR4## wherein: R.sub.3 is selected from the group consisting of [4,5-dihydro-2-oxazolyl; 2-oxazolyl; 2-thiazolyl; 4,5-dihydro-2-thiazolyl; 5,6-dihydro-4H-1,3-oxazin-2-yl; 5,6-dihydro-4H-1,3-thiazin-2-yl;] 4,5-dihydro-1H-imidazol-2-yl; 2-oxazolidinyl; 1,3,4-oxadiazol-2-yl; 4,5-dihydro-1,3,4-oxadiazol-2-yl; 1,3-dithiolan-2-yl; 1,3-dithian-2-yl; 2-thiazolidinyl; 1,3-dioxolan-2-yl; 1,3-dioxan-2-yl; 1,3-oxathiolan-2-yl; 5-tetrazolyl; 5-oxazolyl; and the above mentioned heterocycles substituted with one or more substituents selected from C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.7 alkoxy and trifluoroacetyl; and 1-amino-4,5-dihydro-1H-imidazolyl;
- R.sub.4 is selected from C.sub.1 -C.sub.4 straight or branched chain alkyl, C.sub.3 -C.sub.4 cycloalkyl; C.sub.1 -C.sub.4 alkyl substituted with a C.sub.3 -C.sub.6 Cycloalkyl; C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl; and bis(C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl;
- R.sub.5 is the same as R.sub.3 or is ##STR5## or --C.tbd.N where Z.sub.1 is O, S, or NR.sub.7 where R.sub.7 is lower alkyl, and Z.sub.2 is selected from C.sub.1 -C.sub.7 alkoxy, C.sub.3 -C.sub.7 alkenoxy, C.sub.3 -C.sub.7 alkynoxy, C.sub.1 -C.sub.7 alkylthio, pyrazolyl, halo C.sub.1 -C.sub.7 alkoxy cyano C.sub.1 -C.sub.7 alkoxy, chloro, and --NHR.sub.8 where R.sub.8 is lower alkyl;
- R.sub.2 and R.sub.6 are independently selected from fluorinated methyl, chlorofluorinated methyl, chlorinated methyl, and lower alkyl, provided that one of R.sub.2 and R.sub.6 must be fluorinated or chlorofluorinated methyl;
- provided that R.sub.3 is not 4,5-dihydro-1-methyl-1H-imidazol-2-yl when R.sub.5 is methylthiocarbonyl, and R.sub.3 is not an unsubstituted 4,5-dihydro-1H-imidazol-2-yl when R.sub.5 is methoxycarbonyl.
- 2. A compound according to claim 1 wherein one of R.sub.2 and R.sub.6 is CF.sub.3 and the other is CF.sub.2 H.
- 3. A compound according to claim 2 wherein R.sub.4 is selected from C.sub.3 -C.sub.4 branched chain alkyl.
- 4. A compound according to claim 2 wherein R.sub.4 is selected from cyclobutyl and cyclopropylmethyl.
- 5. A compound according to claim 3 wherein R.sub.5 is methoxycarbonyl.
- 6. A compound according to claim 3 wherein R.sub.5 is methylthiocarbonyl.
- 7. A method of controlling undesirable vegetation comprising applying thereto a compound represented by the formula ##STR6## wherein: R.sub.3 is selected from the group consisting of 4,5-dihydro-1H-imidazol-2-yl; 2-oxazolidinyl; 1,3,4-oxadiazol-2-yl; 4,5-dihydro-1,3,4-oxadiazol-2-yl; 1,3-dithiolan-2-yl; 1,3-dithian-2-yl; 2-thiazolidinyl; 1,3-dioxolan-2-yl; 2 1,3-dioxan-2-yl; 1,3-oxathiolan-2-yl; 2 5-tetrazolyl; 5oxazolyl; and the above mentioned heterocycles substituted with one or more substituents selected from C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.7 alkoxy and trifluoroacetyl; and 1-amino-4,5-dihydro-1H-imidazolyl;
- R.sub.4 is selected from C.sub.1 -C.sub.4 straight or branched chain alkyl, C.sub.3 -C.sub.4 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted with a C.sub.3 -C.sub.6 cycloalkyl; C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl; and bis (C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl;
- R.sub.5 is the same as R.sub.3 is ##STR7## or --C.tbd.N where Z.sub.1 is O, S, or NR.sub.7 where R.sub.7 is lower alkyl, and Z.sub.2 is selected from C.sub.1 -C.sub.7 alkoxy, C.sub.3 -C.sub.7 alkenoxy, C.sub.3 -C.sub.7 alkynoxy, C.sub.1 -C.sub.7 alkylthio, pyrazolyl, halo C.sub.1 -C.sub.7 alkoxy, cyano C.sub.1 -C.sub.7 alkoxy chloro, and --NHR.sub.8 where R.sub.8 is lower alkyl;
- R.sub.2 and R.sub.6 are independently selected from fluorinated methyl, chlorofluorinated methyl, chlorinated methyl, and lower alkyl, provided that one of R.sub.2 and R.sub.6 must be fluorinated or chlorofluorinated methyl;
- provided that R.sub.3 is not 4,5-dihydro-1-methyl-1H-imidazol-2-yl when R.sub.5 is methylthiocarbonyl, and R.sub.3 is not an unsubstituted 4,5-dihydro-1H-imidazol-2-yl when R.sub.5 is methoxycarbonyl.
- 8. A method according to claim 7 wherein one of R.sub.2 and R.sub.6 is CF.sub.3 and the other is CF.sub.2 H.
- 9. A method according to claim 8 wherein R.sub.4 is selected from C.sub.3 -C.sub.4 branched chain alkyl.
- 10. A method according to claim 8 wherein R.sub.4 s selected from cyclobutyl and cyclopropylmethyl.
- 11. A method according to claim 9 wherein R.sub.5 is methylthiocarbonyl.
- 12. A method according to claim 9 wherein R.sub.5 is methylthiocarbonyl.
- 13. A herbicidal composition comprising an adjuvant and a compound represented by the formula
- ______________________________________Elemental Analysis: C H N______________________________________Calculated 52.45 4.14 10.79Found 52.50 4.18 10.77______________________________________
- wherein:
- R.sub.3 is selected from the group consisting of 4,5-dihydro-1H-imidazol-2-yl; 2-oxazolidinyl; 1,3,4-oxadiazol-2-yl; 4,5-dihydro-1,3,4-oxadiazol-2-yl; 1,3-dithiolan-2-yl; 1,3-dithian-2-yl; 2-thiazolidinyl; 1,3-dioxolan-2-yl; 1,3-dioxan-2-yl; 1,3-oxathiolan-2-yl; 5-tetrazolyl; 2 5-oxazolyl; and the above mentioned heterocycles substituted with one or more substituents selected from C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.7 alkoxy and trifluoroacetyl; and 1-amino-4,5-dihydro-1H-imidazolyl;
- R.sub.4 is selected from C.sub.1 -C.sub.4 straight or branched chain alkyl, C.sub.3 -C.sub.4 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted with a C.sub.3 -C.sub.6 cycloalkyl; C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl; and bis(C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl;
- R.sub.5 is the same as R.sub.3 or is ##STR8## or --C.tbd.N where Z.sub.1 is O, S, or NR.sub.7 where R.sub.7 is lower alkyl, and Z.sub.2 is selected from C.sub.1 -C.sub.7 alkoxy, C.sub.3 -C.sub.7 alkenoxy, C.sub.3 -C.sub.7 alkynoxy, C.sub.1 -C.sub.7 alkylthio, pyrazolyl, halo C.sub.1 -C.sub.7 alkoxy cyano C.sub.1 -C.sub.7 alkoxy chloro, and --NHR.sub.8 where R.sub.8 is lower alkyl;
- R.sub.2 and R.sub.6 are independently selected from fluorinated methyl, chlorofluorinated methyl, chlorinated methyl, and lower alkyl, provided that one of R.sub.2 and R.sub.6 must be fluorinated or chlorofluorinated methyl;
- provided that R.sub.3 is not 4,5-dihydro-1-methyl-1H-imidazol-2-yl when R.sub.5 is methylthiocarbonyl, and R.sub.3 is not an unsubstituted 4,5-dihydro-1H-imidazol-2-yl when R.sub.5 is methoxycarbonyl.
- 14. A composition according to claim 13 wherein one of R.sub.2 and R.sub.6 is CF.sub.3 and the other is CF.sub.2 H.
- 15. A composition according to claim 14 wherein R.sub.4 is selected from C.sub.3 -C.sub.4 branched chain alkyl.
- 16. A composition according to claim 14 wherein R.sub.4 is selected from cyclobutyl and cyclopropylmethyl.
- 17. A composition according to claim 15 wherein R.sub.5 is methoxycarbonyl.
- 18. A composition according to claim 15 wherein R.sub.5 is methylthiocarbonyl.
Parent Case Info
This is a division of Application Ser. No. 07/779,783, filed Oct. 21, 1991, now U.S. Pat. No. 5,219,824, which is a division of Application Ser. No. 07/611,809 filed Nov. 13, 1990, now U.S. Pat. No. 5,100,461, which is a division of Application Ser. No. 07/134,231, filed Dec. 24, 1987, now U.S. Pat. No. 4,988,384, which is a continuation-in-part of Application Ser. No. 07/012,930, filed Feb. 9, 1987, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5100461 |
Sing et al. |
Mar 1992 |
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Divisions (3)
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Number |
Date |
Country |
Parent |
779783 |
Oct 1991 |
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Parent |
611809 |
Nov 1990 |
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Parent |
134231 |
Dec 1987 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
12930 |
Feb 1987 |
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