TH8565A - Different triazolinones with weed killing effects - Google Patents

Abstract

The herbicide compound is Q-substitute 1-phenyl-4,5-dihydro-1,2,4-triazole-5(1-H)-one, in which the substituent Q is bonded to the carbon atom of the ring at position 5 of the phenyl group and in which: Q is -CH(R2)C(R3)(R3)(R4) Q'' or -CH=C(R4) Q''; each independent R2 and R3 is H or halogen; R4 is H or low alkyl; Q'' is COOH, COOZ, COOR5, CON(R6)(R7), CN, CHO or C(O)R5; Z is the salt group; R5 is an alkyl, alkoxycarbonyl alkyl, cycloalkyl or ralkyl; Each independent group of R6 and R7 is an alkyl, cycloalkyl, alkynyl, alkynyl, alkoxy, phenyl, benzyl, or SO2R6, or any one of the aforementioned groups substituted with a halogen, alkyl, or cyanol; the compounds mentioned are those in which the various 5-methoxy analogs and the 5-pro-pargiloxy analogs of these compounds are herbicides.

Claims (16)

1. The herbicide compound with the formula R. R1 is a halogen or small alkyl, R1 is a haloalkyl, X is hydrogen, halogen, alkyl, haloalkyl, alkoxy or nitro, Y is hydrogen, halogen, alkyl, alkoxy, haloalkyl, small haloalkylsulfinyl or small haloalkoxy, Q is CH(R2) C(R3) (R4)Q' or CH=C(R4)Q', R2 is H or halogen, R3 is a halogen, R4 is H or small alkyl, Q' is CO2H, CO2R5, CON(R6)(R7), CN, CHO, or C(O)R5, R5 is an alkyl, alkoxycarbonyl alkyl, cycloalkyl, benzyl, chlorobenzyl, alkylbenzyl or haloalkylbenzyl, and each independent R6 and R7 is H. Or a radical, which is an alkylcycloalkyl, alkenil, alkinil, alkoxy, phenyl, benzyl, or SO2R6 (where R6 is something other than M), or one of the aforementioned radicals with a halogen, alkyl, or cyanol substituent group, or a base-assisted salt of a compound where Q' is CO2M; provided that the alkyl, alkenil, or alkinil group has fewer than 6 carbon atoms and the cycloalkyl group has 3 to 7 carbon atoms. 2. The compounds according to claim 1, where R is CH3, R1 is CHF2, X is F or C1, and Y is CI or Br. 3. The compound in claim 2, where Q is CH2CH(CI)COOR5 and R5 is a small alkyl. 4. The compounds as defined in claim 1, where R5 is ethyl, X is F, and Y is CI. 5. The compound according to claim 2, where Q is CH=CHQ'. 6. The compounds as defined in claim 3, where X is CI, Y is CI, and R5 is methyl. 7. The compound in claim 1, where Q is CH2CH(CI)Q'. 8. A herbicide mixture containing the effective herbicide concentrations of the compounds of claim 1 in a mixture with a suitable carrier. 9. A method for controlling unwanted plant growth consisting of the application of a mixture of the compounds under claim 10 in quantities effective in killing weeds at the desired control site. 10. A herbicide mixture containing the effective herbicide concentrations of the compounds of claim 5 in a mixture with a suitable vector. 11. A method for controlling unwanted plant growth, consisting of the application of a mixture of the compounds under Patent 10 in quantities effective in killing weeds at the desired control site. 12. A herbicide mixture containing the herbicide-effective quantities of the compounds of claim 7 in a mixture with a suitable carrier. 13. A method for controlling unwanted plant growth consisting of the application of a mixture of the compounds under claim 12 in quantities effective in killing weeds at the desired infestation points. 14. Ethyl 2-chloro-3-(2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl)-phenyl)propionate 15. A herbicide mixture containing the herbicide-effective quantities of the compounds of claim 14 in a mixture with a suitable carrier. 16. A method for controlling unwanted plant growth consisting of the application of a mixture of the compounds under Protection 14 in quantities effective in killing weeds at the desired infestation site (Protection 16, 3 pages, Figure).