Claims
- 1. A method for the control of monocotyledonous, or dicotyledonous annual or perennial plant species comprising: applying to the foliage of said plant or to soil or water containing seeds or other propagating organs thereof, a herbicidally effective amount of a compound having a structure: ##STR51## wherein A in both formula (I) and (II) is hydrogen;
- straight or branched C.sub.1 -C.sub.4 alkyl, optionally substituted with one to three halogens, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, carboalkoxy, phenyl, or oxo;
- straight or branched C.sub.2 -C.sub.4 alkenyl, optionally substituted with one to three halogens or phenyl;
- C.sub.2 -C.sub.4 alkynyl, optionally substituted with one to three halogens;
- and additionally in formula (II) A is amino, optionally substituted with straight or branched C.sub.2 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 haloalkyl, straight or branched C.sub.2 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 cycloalkenyl, phenyl, benzyl, (di)alkylamino, or C.sub.1 -C.sub.4 alkoxy;
- C.sub.1 -C.sub.4 alkoxy; or
- C.sub.1 -C.sub.4 alkylthio;
- R.sub.1 is C.sub.1 -C.sub.4 alkyl;
- R.sub.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl; and when R.sub.1 and R.sub.2 are taken together with the carbon to which they are attached, they may be C.sub.3 -C.sub.6 cycloalkyl optionally substituted with methyl;
- and when R.sub.1 and R.sub.2 are not the same, thus creating an asymmetric center, an optical isomer thereof;
- Q is represented by formula (III) ##STR52## wherein R.sub.3 -R.sub.7 are each hydrogen; halogen; nitro; cyano; straight or branched C.sub.1 -C.sub.4 alkyl, optionally substituted with one or more halogens or phenyl;
- straight or branched C.sub.2 -C.sub.4 alkenyl, optionally substituted with one to three halogens;
- OR.sub.8 where R.sub.8 is hydrogen; C.sub.1 -C.sub.4 alkyl, optionally substituted with halogen(s), C.sub.1 -C.sub.4 alkoxy, or phenyl; or
- C.sub.2 -C.sub.4 alkenyl optionally substituted with one to three halogens or phenyl;
- phenyl, optionally substituted with one to three halogens, one to three C.sub.1 -C.sub.4 alkyl, one to three C.sub.1 -C.sub.4 alkoxy, or one to two nitro;
- C.sub.1 -C.sub.4 alkylcarbonyl, optionally substituted with halogen(s);
- C.sub.1 -C.sub.4 alkylthio, optionally substituted with halogen(s);
- C.sub.1 -C.sub.4 alkylsulfinyl, optionally substituted with halogen(s);
- C.sub.1 -C.sub.4 alkylsulfonyl, optionally substituted with halogen(s);
- amino, optionally substituted with C.sub.1 -C.sub.4 alkyl;
- CO.sub.2 R.sub.9 where R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl, optionally substituted with one to three halogens; or
- R.sub.3 -R.sub.4, R.sub.4 -R.sub.5, R.sub.5 -R.sub.6 and R.sub.6 -R.sub.7 may also be --(CH.dbd.CH--CH.dbd.CH)--, optionally substituted with up to three of the substituents described for R.sub.3 -R.sub.7 above;
- with the proviso that no more than three of R.sub.3 -R.sub.7 can be: cyano, nitro, (substituted)phenyl, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, amino or CO.sub.2 R.sub.9 ;
- W is O or S; and
- Y is hydrogen, or a salt thereof, wherein Y is a cation.
- 2. The method according to claim 1 wherein
- A is hydrogen or methyl;
- R.sub.1 is methyl;
- R.sub.2 is isopropyl;
- R.sub.3 -R.sub.7 are each hydrogen halogen(s) or C.sub.1 -C.sub.4 alkyl(s), optionally substituted with halogen; and
- Y is hydrogen, or a cation of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium, or organic ammonium.
- 3. The method according to claim 1 wherein
- A is methyl;
- R.sub.1 is methyl;
- R.sub.2 is isopropyl;
- R.sub.3 is hydrogen, halogen or methyl;
- R.sub.5 is halogen or methyl, and
- W is oxygen.
- 4. The method according to claim 3, wherein the compound is 4-isopropyl-2,4-dimethyl-1-(p-tolylsulfonyl)-2-imidazolin-5-one.
- 5. The method according to claim 3, wherein the compound is 1-[(p-chlorophenyl)sulfonyl]-4-isopropyl-2,4-dimethyl-2-imidazolin-5-one.
- 6. The method according to claim 3, wherein the compound is 1-[(4-chloro-o-tolyl)sulfonyl]-4-isopropyl-2,4-dimethyl-2-imidazolin-5-one
- 7. The method according to claim 3, wherein the compound is (S)-(-)-1-[(4-chloro-o-tolyl)sulfonyl]-4-isopropyl-2,4-dimethyl-2-imidazolin-5-one.
- 8. The method according to claim 3, wherein the compound is 2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide.
- 9. The method according to claim 3, wherein the compound is 2-acetamido-N-[(p-chlorophenyl)sulfonyl]-2,3-dimethylbutyramide.
- 10. The method according to claim 3, wherein the compound is 2-acetamido-N-[(4-chlorophenyl-o-tolyl)sulfonyl]-2,3-dimethylbutyramide.
- 11. The method according to claim 3, wherein the compound is (S)-(+)-2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide.
- 12. The method according to claim 3, wherein the compound is (S)-(+)-2-acetamido-N-[(p-chlorophenyl)sulfonyl]-2,3-dimethylbutyramide.
- 13. The method according to claim 3, wherein the compound is 2-acetamido-N-[(2,4-dichlorophenyl)sulfonyl]-2,3-dimethylbutyramide.
Parent Case Info
This application is a division of application Ser. No. 07/611,626, filed Nov. 13, 1990, now U.S. Pat. No. 5,120,854, issued Jun. 9, 1992 which is a division of application Ser. No. 07/417,400, filed Oct. 5, 1989, now U.S. Pat. No. 4,992,094, issued Feb. 12, 1991, which is a division of application Ser. No. 07/214,507, filed Jul. 7, 1988, now U.S. Pat. No. 4,883,914, issued Nov. 28, 1989, which, in turn, is a continuation-in-part of application Ser. No. 07/086,416, filed Aug. 17, 1987, abandoned.
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Number |
Name |
Date |
Kind |
3432507 |
Paquette |
Mar 1969 |
|
4132786 |
Moreau et al. |
Jan 1979 |
|
4218238 |
Taylor et al. |
Aug 1980 |
|
4404012 |
Orwick et al. |
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Entry |
Chemical Abstracts, vol. 53, No. 9, Abstract 9115(b-d), May 10, 1959. |
Chemical Abstracts, vol. 54, No. 17, Abstract 18378-79,Sep. 10, 1960. |
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Divisions (3)
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Number |
Date |
Country |
Parent |
611626 |
Nov 1990 |
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Parent |
417400 |
Oct 1989 |
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Parent |
214507 |
Jul 1988 |
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Continuation in Parts (1)
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Number |
Date |
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Parent |
86416 |
Aug 1987 |
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