Claims
- 1. A compound of the formula ##STR32## wherein A is hydroxymethyl, chloromethyl, carboxy, carboxy salt, alkoxycarbonyl or alkylaminocarbonyl;
- D is nitrogen;
- n is 0 or 1;
- R is hydrogen, (C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkyl containing from one to nine halo atoms, or phenyl;
- R.sup.1 is hydrogen, (C.sub.1 -C.sub.2)alkyl or halo(C.sub.1 -C.sub.2)alkyl;
- R.sup.2 is hydrogen or (C.sub.1 -C.sub.2)alkyl;
- T is hydrogen or fluorine;
- X is hydrogen or halogen;
- Y is hydrogen, halo(C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)alkyl, cyano, nitro, halogen, phenoxy or phenylthio, provided when Y is hydrogen, R is trifluoromethyl, and R.sup.1 and R.sup.2 are hydrogen and Z is not hydrogen; and when Y is chlorine and Z is a substituent linked to the phenyl ring by oxygen, R is not hydrogen; and
- Z is hydrogen, hydroxy, halogen, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, carboxyalkoxy, carboxyalkylthio, alkoxycarbonylalkoxy, alkoxycarbonylalkylthio, cycloalkoxy, cycloalkylalkoxy, cycloalkylthio, cycloalkylalkylthio, formyl, alkanoyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkoxycarbonyl, alkyl, hydroxyalkyl, alkoxyalkyl, alkenyloxyalkyl, alkynyloxyalkyl, alkylthioalkyl, alkenylthioalkyl, alkynylthioalkyl, cycloalkoxyalkyl, cycloalkylalkoxyalkyl, cycloalkylthioalkyl, cycloalkylalkylthioalkyl, alkoxycarbonylalkoxyalkyl, phenoxyalkyl, phenylthioalkyl, alkylaminoalkyl, oximyl, alkyloximyl, alkenyloximyl, alkynyloximyl, alkoxycarbonylalkyloximyl, alkyl(alkyl)oximyl, alkenyl(alkyl)oximyl, alkynyl(alkyl)oximyl, alkoxycarbonylalkyl(alkyl)oximyl, alkylamino, monoalkenylamino, monoalkynylamino, or alkanoylamino.
- 2. A compound of claim 1 wherein
- A is CH.sub.2 OH, CH.sub.2 Cl, COOH, COO--M+ wherein M+ is an agronomically acceptable salt, (C.sub.1 -C.sub.6)alkoxycarbonyl, or (C.sub.1 -C.sub.6)alkylaminocarbonyl:
- n is 0;
- D is nitrogen;
- R is hydrogen, (C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkyl or phenyl;
- 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;
- T is hydrogen or fluorine;
- X is hydrogen or halogen, provided that when X and Z are each independently hydrogen or halogen, Y is halogen and R must be trifluoromethyl;
- Y is hydrogen, halogen, trifluoromethyl, phenoxy, cyano or nitro, provided when Y is hydrogen, R is trifluoromethyl and R.sup.1 and R.sup.2 are hydrogen and Z is not hydrogen; and when Y is chlorine and Z is a substituent linked to the phenyl ring by oxygen, R is not hydrogen; and
- Z is hydrogen, halogen, (C.sub.1 -C.sub.6)alkoxy, (C.sub.3 -C.sub.6)alkenyloxy, (C.sub.3 -C.sub.6)alkynyloxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.3 -C.sub.6)alkenylthio, (C.sub.3 -C.sub.6)alkynylthio, phenyl(C.sub.1 -C.sub.6)alkoxy, phenyl(C.sub.1 -C.sub.6)alkylthio, carboxy(C.sub.1 -C.sub.6)alkythio, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.6)alkanoyl, (C.sub.1 -C.sub.6)alkoxycarbonyl, (C.sub.3 -C.sub.6)cycloalkoxycarbonyl, (C.sub.1 -C.sub.6)(C.sub.1 -C.sub.6)alkanoyl, (C.sub.1 -C.sub.6)alkoxycarbonyl, (C.sub.3 -C.sub.6)cycloalkoxycarbonyl, (C.sub.3 -C.sub.6)cycloalkyl (C.sub.1 -C.sub.6)alkoxycarbonyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkoxycarbonyl, (C.sub.1 -C.sub.6)alkyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)alkenyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)alkynyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkythio(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6 )alkoxy(C.sub.1 -C.sub.6)alkyl, phenoxy(C.sub.1 -C.sub.6)alkyl, phenylthio(C.sub.1 -C.sub.6)alkyl, or di(C.sub.1 -C.sub.6)alkylamino(C.sub.1 -C.sub.6)alkyl.
- 3. The compound of claim 2 wherein
- A is CO.sub.2 H, (C.sub.1 -C.sub.6)alkoxycarbonyl or CO.sub.2 --M+;
- n is 0;
- R is (C.sub.1 -C.sub.4)alkyl or halo(C.sub.1 -C.sub.4)alkyl;
- R.sup.1 is hydrogen or (C.sub.1 -C.sub.2)alkyl;
- R.sup.2 is hydrogen;
- X is hydrogen or halogen;
- Y is hydrogen or halogen;
- T is hydrogen or fluorine;
- Z is hydrogen, (C.sub.1 -C.sub.6)alkoxy, (C.sub.3 -C.sub.6)alkenyloxy, (C.sub.3 -C.sub.6)alkynyloxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.3 -C.sub.6)alkenylthio, (C.sub.3 -C.sub.6)alkynylthio, phenyl(C.sub.1 -C.sub.6)alkoxy, phenyl(C.sub.1 -C.sub.6)alkylthio, carboxy(C.sub.1 -C.sub.6)alkylthio, or (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkylthio.
- 4. The compound of claim 3 wherein A is carboxy, (C.sub.1 -C.sub.6)alkoxycarbonyl or CO.sub.2 --M+; n is 0; R is CH.sub.3, CF.sub.3 or CF.sub.2 CF.sub.3 ; R.sup.1 is H; X is Cl or F; Y is Br, F, or Cl; T is H; and Z is (C.sub.1 -C.sub.6)alkoxy, (C.sub.3 -C.sub.6)alkenyloxy, or (C.sub.3 -C.sub.6)alkynyloxy.
- 5. The compound of claim 4 wherein A is carboxy, ethoxycarbonyl, methoxycarbonyl, isopropyloxycarbonyl, isopropylammonium carboxylate or potassium carboxylate; X is F; Y is Cl; and Z is propargyloxy, allyloxy, n-propyloxy, isopropyloxy, ethoxy or methoxy.
- 6. The compound of claim 5 wherein A is COOH; R is CF.sub.3 ; and Z is propargyloxy, isopropyloxy, n-propyloxy, ethoxy, methoxy or allyloxy.
- 7. The compound of claim 5 wherein R is CH.sub.3 ; A is COOH; and Z is propargyloxy.
- 8. The compound of claim 5 wherein R is CF.sub.2 CF.sub.3 ; A is COOH; and Z is propargyloxy.
- 9. The compound of claim 5 wherein R is CF.sub.3 ; Z is propargyloxy; and A is carboxy, ethoxycarbonyl, methoxycarbonyl, isopropyloxycarbonyl, isopropylammonium carboxylate or potassium carboxylate.
- 10. The compound of claim 5 wherein R is CF.sub.3 ; Z is isopropyloxy; and A is carboxy or methoxycarbonyl.
- 11. The compound of claim 2 wherein
- A is carboxy;
- n is 0;
- R is (C.sub.1 -C.sub.4)alkyl or halo(C.sub.1 -C.sub.4)alkyl;
- R.sup.1 is H or (C.sub.1 -C.sub.2)alkyl;
- R.sup.2 is H;
- X is H or halogen;
- Y is H or halogen;
- T is H or F; and
- Z is (C.sub.1 -C.sub.6)alkoxycarbonyl;
- or its agronomically acceptable salts.
- 12. The compound of claim 11 wherein A is COOH; R is CF.sub.3 ; R.sup.1 is hydrogen; X is Cl or F; Y is Br, F or Cl; T is hydrogen; and Z is (C.sub.1 -C.sub.6)alkoxycarbonyl.
- 13. The compound of claim 12 wherein X is F; Y is Cl; and Z is isopropyloxycarbonyl.
- 14. The compound of claim 2 wherein
- A is carboxy;
- n is 0;
- R is (C.sub.1 -C.sub.4)alkyl or halo(C.sub.1 -C.sub.4)alkyl;
- R.sup.1 is H or (C.sub.1 -C.sub.2)alkyl;
- R.sup.2 is H;
- X is H or halogen;
- Y is H or halogen;
- T is H or F; and
- Z is (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)alkenyloxy(C.sub.1 -C.sub.6)alkyl or (C.sub.3 -C.sub.6)alkynyloxy(C.sub.1 -C.sub.6)alkyl;
- or its agronomically acceptable salts.
- 15. The compound of claim 14 wherein A is carboxy; n is 0; R is CF.sub.3 ; R.sup.1 is hydrogen; X is Cl or F; Y is Br, F or Cl; T is hydrogen; and Z is (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)alkenyloxy(C.sub.1 -C.sub.6)alkyl or (C.sub.3 -C.sub.6)alkynyloxy(C.sub.1 -C.sub.6)alkyl.
- 16. The compound of claim 15 wherein X is F, Y is Cl, and Z is isopropyloxymethyl or 1-methylpropargyloxymethyl.
- 17. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 5.
- 18. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 6.
- 19. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 7.
- 20. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 8.
- 21. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 9.
- 22. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 10.
- 23. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 11.
- 24. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 12.
- 25. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 13.
- 26. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 14.
- 27. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 15.
- 28. A herbicidal composition comprising an agronomically acceptable carrier and a herbicidally effective amount of the compound of claim 16.
- 29. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 9.
- 30. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 10.
- 31. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 11.
- 32. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 12.
- 33. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 13.
- 34. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 14.
- 35. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 15.
- 36. A method for controlling unwanted plants which comprises applying to the plant or growth medium therefore the compound of claim 16.
- 37. The method of claim 29 wherein the compound is applied at a rate of from about 0.001 to about 12 pounds per acre.
- 38. The method of claim 37 wherein the compound is applied at a rate of from about 0.01 to about 5 pounds per acre.
Parent Case Info
This application is a continuation-in-part of application Ser. No. 401,268, filed Aug. 31, 1989, abandoned.
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4489010 |
Teach et al. |
Dec 1984 |
|
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Number |
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391847 |
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Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
401268 |
Aug 1989 |
|