Claims
- 1. A herbicidal compound of the formula ##STR60## wherein A is carbonyl, thiocarbonyl or methylene;
- A.sup.1 is carbonyl or methylene;
- Q is (CH.sub.2).sub.n, where n is 0 or 1, or oxygen;
- R is (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl containing from one to nine halo atoms, or phenyl;
- R.sup.1 is hydrogen or (C.sub.1 -C.sub.2)alkyl;
- R.sup.2 is hydrogen; or
- R, R.sup.1 and R.sup.2 taken together form a fused phenyl ring;
- X is hydrogen, cyano or halogen;
- T is hydrogen or fluorine; and
- Z and Y together form a 6-membered heterocyclic ring fused to the phenyl ring structure to form a bicyclic moiety having the structure ##STR61## wherein L is oxygen
- R.sup.3 is hydrogen or alkyl;
- R.sup.4 is hydrogen; alkyl; alkenyl; alkynyl; alkoxyalkyl; alkenyloxyalkyl; alkynyloxyalkyl; alkoxycarbonylalkyl; cycloalkyl; cycloalkylalkyl; alkylaminoalkyl; alkylaminocarbonylalkyl; heterocyclyl or heterocyclyl(C.sub.1 -C.sub.6)alkyl wherein the heterocyclyl group is a three to six membered heterocyclic ring containing one, two or three hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur: alkoxycarbonylalkyl, phenylalkyl; alkylthioalkyl; alkenylthioalkyl; alkynylthioalkyl; alkoxycarbonyl; or alkanoyl;
- and the agronomically acceptable salts thereof.
- 2. The compound of claim 1 wherein
- A is C.dbd.O, C.dbd.S or CH.sub.2 ;
- A.sup.1 is C.dbd.O or CH.sub.2 ;
- Q is (CH.sub.2).sub.n, where n is 0 or 1, or oxygen;
- R is (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl or phenyl;
- R.sup.1 is H or (C.sub.1 -C.sub.2)alkyl;
- R.sup.2 is H or, together with R and R.sup.1, fused phenyl;
- X is H, Cl, Br, CN or F;
- T is H or F;
- Z and Y together form a 6-membered heterocyclic ring fused to the phenyl ring structure to form a bicyclic moiety having the structure ##STR62## wherein R.sup.3 is hydrogen or (C.sub.1 -C.sub.3)alkyl; and R.sup.4 is hydrogen; (C.sub.1 -C.sub.8)alkyl; (C.sub.3 -C.sub.6)alkenyl; (C.sub.3 -C.sub.6)alkynyl;
- (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl; (C.sub.1 -C.sub.6)alkylthio(C.sub.1 -C.sub.6)alkyl; (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.6)alkyl; heterocyclyl or heterocyclyl(C.sub.1 -C.sub.6)alkyl wherein the heterocyclyl group is a three to six membered heterocyclic ring containing one, two or three hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur: di(C.sub.1 -C.sub.6)alkylamino(C.sub.1 -C.sub.6)alkyl; di(C.sub.1 -C.sub.6)alkylaminocarbonyl(C.sub.1 -C.sub.6)alkyl; phenyl(C.sub.1 -C.sub.6)alkyl; cyano(C.sub.1 -C.sub.6)alkyl; (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkyl; (C.sub.1 -C.sub.6)alkoxycarbonyl; or (C.sub.1 -C.sub.6)alkanoyl; and
- the agronomically acceptable salts thereof.
- 3. The compound of claim 2 wherein Z and Y together form a 6-membered heterocyclic ring fused to the phenyl ring structure to form a bicyclic moiety having the structure ##STR63## wherein A and A.sup.1 are C.dbd.O;
- Q is (CH.sub.2).sub.n, where n is 0;
- L is O;
- X is H or F:
- R is (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl or phenyl;
- R.sup.1 is H or (C.sub.1 -C.sub.2)alkyl;
- R.sup.2 is H or, together with R and R.sup.1, fused phenyl;
- R.sup.3 is H or (C.sub.1 -C.sub.3)alkyl; and
- R.sup.4 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.3 -C.sub.6)alkenyl, (C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkylthio(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, cyano(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkyl; alkylaminocarbonylalkyl; heterocyclyl or heterocyclyl(C.sub.1 -C.sub.6)alkyl wherein the heterocyclyl group is a three to six membered heterocyclic ring containing one, two or three hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur; alkoxycarbonylalkyl; alkylaminoalkyl; (C.sub.1 -C.sub.6)alkoxycarbonyl or (C.sub.1 -C.sub.6)alkanoyl; and the agronomically acceptable salts thereof.
- 4. The compound of claim 3 of the formula ##STR64## wherein L is 0;
- X is H or F;
- R is CH.sub.3, CHF.sub.2, CFH.sub.2 or CF.sub.3 ;
- R.sup.3 is H or (C.sub.1 -C.sub.3)alkyl; and
- R.sup.4 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.3 -C.sub.6)alkenyl, (C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxymethyl, (C.sub.1 -C.sub.6)alkylthiomethyl, halo(C.sub.3 -C.sub.6)alkenyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.6)alkyl, heterocyclyl or heterocyclyl(C.sub.1 -C.sub.6)alkyl wherein the heterocyclyl group is a three to six membered heterocyclic ring containing one, two or three hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur; di(C.sub.1 -C.sub.6)alkylamino(C.sub.1 -C.sub.6)alkyl, di(C.sub.1 -C.sub.6)alkylaminocarbonyl(C.sub.1 -C.sub.6)alkyl or cyano(C.sub.1 -C.sub.6)alkyl.
- 5. The compound of claim 4 wherein X is H or F, R is CH.sub.3, CHF.sub.2 or CF.sub.3, R.sup.3 is H, CH.sub.3 or CH.sub.2 CH.sub.3, and R.sup.4 is propargyl, allyl, ethoxymethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, 1-ethylpropyl, 2-methoxyethyl, methoxymethyl, methylthiomethyl, 1-cyanoethyl, 1-methylpropargyl, 2-methylallyl, cyanomethyl, cyclopropylmethyl, cyclopentyl, dimethylaminocarbonylmethyl, 2-tetrahydrofuranylmethyl, 3-tetrahydrofuranyl, 2-chloroallyl, or 3,3-dichloroallyl.
- 6. The compound of claim 5 wherein L is oxygen, R is CH.sub.3, R.sup.3 is H, R.sup.4 is propargyl and X is F.
- 7. The compound of claim 5 wherein R is CF.sub.3, R.sup.3 is CH.sub.3, R.sup.4 is propargyl, L is oxygen and X is H or F.
- 8. The compound of claim 5 wherein R is CF.sub.3, R.sup.3 and X are H, L is oxygen and R.sup.4 is propargyl, n-propyl, 1-methylpropargyl, allyl, s-butyl, methoxymethyl or 2-methoxyethyl.
- 9. The compound of claim 5 wherein R is CF.sub.3, R.sup.3 is H, X is F, L is oxygen and R.sup.4 is propargyl, cyanomethyl, allyl, methoxymethyl, ethoxymethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, 1-cyanoethyl, 2-methylallyl, methylthiomethyl, 2-ethylpropyl, cyclopropylmethyl, cydopentyl, dimethylaminocarbonylmethyl, 2-tetrahydrofuranylmethyl, 3-tetrahydrofuranyl, 2-chloroallyl, 3,3-dichloroallyl or ethyl.
- 10. The compound of claim 5 wherein R is CHF.sub.2, R.sup.3 is H, L is oxygen, X is F and R.sup.4 is allyl.
- 11. The compound of claim 5 wherein R is CF.sub.3, R.sup.3 is CH.sub.2 CH.sub.3, L is oxygen, X is F, and R.sup.4 is propargyl.
- 12. The compound of claim 5 wherein R is CF.sub.3, R.sup.3 is H, L is sulfur, X is F and R.sup.4 is propargyl.
- 13. The compound of claim 1 which is 7-fluoro-4-methoxymethyl-6-(N-(3-(trifluoromethyl)-glutarimido))-2H- 1,4-benzoazin-3-(4H)one.
- 14. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 1.
- 15. A herbiddal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 2.
- 16. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 1.
- 17. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 2.
- 18. The method of claim 16 wherein the compound is applied preemergence.
- 19. The method of claim 16 wherein the compound is applied postemergence.
- 20. A method for controlling unwanted plants which comprises applying to the the plant or growth medium the compound of claim 13.
Parent Case Info
This is a divisional of application Ser. No. 129,483, filed Sep. 30, 1993, now U.S. Pat. No. 5,393,735, which is a continuation of U.S. Ser. No. 563,780 filed Aug. 9, 1990 abandoned; which is a continuation-in-part of U.S. Ser. No. 401,329 filed Aug. 31, 1989 abandoned.
US Referenced Citations (15)
Foreign Referenced Citations (4)
Number |
Date |
Country |
391847 |
Oct 1990 |
EPX |
253084 |
Oct 1988 |
JPX |
1237 |
Jan 1990 |
CHX |
3869 |
Jan 1990 |
CHX |
Non-Patent Literature Citations (4)
Entry |
Satow et al. "Preparation of N-phenylglutarimides as herbicides" CA 116:59224t (1992). |
Modena et al., 2 (Arylamino)Carbonyl!benzeneacetic . . . , Farmaco 44, pp. 721-729 (1989). |
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Divisions (1)
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Number |
Date |
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Parent |
129483 |
Sep 1993 |
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Continuations (1)
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Date |
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Parent |
563780 |
Aug 1990 |
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Continuation in Parts (1)
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Number |
Date |
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Parent |
401329 |
Aug 1989 |
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