Claims
- 1. Agriculturally suitable compositions for controlling the growth of undesired vegetation in a crop comprising an effective amount of a compound of Formula I ##STR193## wherein R.sup.1 is Cl, Br, I, OCH.sub.3, OCHF.sub.2 or OCF.sub.3 ;
- R.sup.2 is CN, CO.sub.2 R.sup.4, CHO, C(X)NR.sup.17 R.sup.18, C(S)OR.sup.6, C.tbd.CH, CHR.sup.19 OR.sup.20, CH.dbd.NOR.sup.7 or CH.dbd.CR.sup.21 R.sup.22 ;
- R.sup.3 is n-propyl; C.sub.4 -C.sub.10 alkyl; n-propyl or C.sub.4 -C.sub.7 alkyl substituted with one or more halogen, OR.sup.8, SR.sup.9 or NR.sup.10 R.sup.11 ; C.sub.1 -C.sub.3 alkyl substituted with OR.sup.16, CO.sub.2 (C.sub.1 -C.sub.2 alkyl) or phenyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen; C.sub.3 -C.sub.6 cycloalkyl; CH.sub.2 (C.sub.3 -C.sub.6 cycloalkyl); phenyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen; C.sub.2 -C.sub.6 alkenyl optionally substituted with one or more halogen or CO.sub.2 (C.sub.1 -C.sub.2 alkyl); OR.sup.12 ; SR.sup.13 ; or NR.sup.14 R.sup.15 ;
- R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, ##STR194## R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently H or C.sub.1 -C.sub.2 alkyl;
- R.sup.12 and R.sup.13 are independently C.sub.2 -C.sub.10 alkyl optionally substituted with one or more halogen, OR.sup.8, SR.sup.9 or NR.sup.10 R.sup.11 ; phenyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen; or benzyl;
- R.sup.14 and R.sup.15 are independently H or C.sub.1 -C.sub.2 alkyl, or may be taken together as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)--;
- R.sup.16 is H, C.sub.1 -C.sub.8 alkyl; benzyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen; or phenyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen;
- R.sup.17 is H, C.sub.1 -C.sub.2 alkyl or phenyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen;
- R.sup.18 is H, C.sub.1 -C.sub.2 alkyl, C.sub.3 -C.sub.6 cycloalkyl, CH.sub.2 (C.sub.3 -C.sub.6 cycloalkyl), O(C.sub.1 -C.sub.4 alkyl), O-allyl or may be taken together with R.sup.17 as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)--;
- R.sup.19 is H or C.sub.1 -C.sub.2 alkyl;
- R.sup.20 is H or C(O)CH.sub.3 ;
- R.sup.21 and R.sup.22 are independently H, CN, CO.sub.2 R.sup.4, C(X)NR.sup.17 R.sup.18 or halogen;
- X is O or S;
- or their N-oxides or agriculturally suitable salts thereof provided that when R.sup.1 is Cl, Br or I, and R.sup.2 is CN, CO.sub.2 R.sup.4 or C(O)NR.sup.17 R.sup.18, then R.sup.3 is other than optionally substituted 5-phenyl and at least one of the following: surfactant, solid, or liquid diluent.
- 2. The compositions of claim 1 wherein
- R.sup.1 is Cl, Br, I or OCH.sub.3 ;
- R.sup.2 is CN, CO.sub.2 R.sup.4, CHO, C(X)NH.sub.2, C(X)NH(C.sub.1 -C.sub.2 alkyl), C(X)N(C.sub.1 -C.sub.2 alkyl).sub.2, C(S)OR.sup.6 or C.tbd.CH;
- R.sup.3 is n-propyl, C.sub.4 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or phenyl;
- R.sup.4 is H or C.sub.1 -C.sub.2 alkyl; and
- R.sup.6 is C.sub.1 -C.sub.2 alkyl.
- 3. The compositions of claim 1 wherein
- R.sup.1 is Cl, Br or I;
- R.sup.2 is CN, CO.sub.2 H, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, CHO, C(O)NH.sub.2, C(O)NHCH.sub.3, C(O)N(CH.sub.3).sub.2, CH.sub.2 OH or CH.dbd.NOR.sup.7 ;
- R.sup.3 is n-propyl; C.sub.4 -C.sub.7 alkyl; C.sub.2 alkyl substituted with phenyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen; CH.sub.2 (C.sub.3 -C.sub.6 cycloalkyl); or phenyl optionally substituted with one or more CH.sub.3, CF.sub.3, OCH.sub.3, SCH.sub.3 or halogen.
- 4. The compositions of claim 3 wherein
- R.sup.1 is Cl or Br;
- R.sup.2 is CN, CO.sub.2 H or C(O)NH.sub.2 ;
- R.sup.3 is C.sub.4 -C.sub.7 alkyl or CH.sub.2 (C.sub.3 -C.sub.6 cycloalkyl).
- 5. The compositions of of claim 4 wherein R.sup.3 is substituted at the 6-pyridine position.
- 6. The composition of claim 5 wherein the compounds are 2-bromo-6-(3-methylbutyl)-3-pyridinecarboxamide or 2-chloro-6-(3-methylbutyl)-3-pyridinecarboxamide.
- 7. A method for controlling the growth of barnyardgrass or California watergrass in a crop by applying to the locus of the crop to be protected an effective amount of a composition of any one of claims 1-6.
- 8. The compositions of claim 1 wherein there is in combination with the compound of Formula I when R.sup.1 is Br or Cl, R.sup.2 is C(O)NH.sub.2 and R.sup.3 is CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2, one or more herbicidal compound selected from the group consisting of bensulfuron methyl; mefenacet; metsulfuron methyl; pyrazosulfuron ethyl; butachlor; N-[2-(2-methoxyethoxyphenylsulfonyl]-N.sup.1 -4,6-dimethoxy-1,3,5-triazin-2-yl urea; N-[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide; S,S-dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinecarbothiate; and 3-chloro-N[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]imidazo[1,2-a]pyridine-3-sulfonamide.
- 9. The composition of claim 8 wherein the herbicidal compound is selected from butachlor and 3-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]imidazo-[1,2-a]pyridine-3-sulfonamide.
- 10. The composition of claim 8 wherein R.sup.1 is Br and the herbicidal compound is mefenacet.
Parent Case Info
This application is a continuation filed under 35 USC 371 of PCT/US92/04644, which is a continuation-in-part of Ser. No. 07/713,909, filed Jun. 12, 1991, now abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US92/04644 |
6/9/1992 |
|
|
12/9/1993 |
12/9/1993 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO92/22203 |
12/23/1992 |
|
|
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3495969 |
Driscoll |
Feb 1970 |
|
4473395 |
Hawkins et al. |
Sep 1984 |
|
4715888 |
Marzolph et al. |
Dec 1987 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
3939233 |
Mar 1991 |
DEX |
Non-Patent Literature Citations (3)
Entry |
Bird et al. "Herbicidal 5-pyridylcyclohexane-1,3-dione derivatives" EP 104,876. Abstract CA 101:110737g. 1984. |
Rynbrandt et al. J. Med. Chem. 1979,22(5),525-528. |
Shramm et al. Khim-Geterotsikl Soedin, 1984(3),372-375. (Translation). |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
713909 |
Jun 1991 |
|