US-12616203-B2 - Use of 3-isoxazolidinones compounds as selective herbicides

US12616203B2US 12616203 B2US12616203 B2US 12616203B2US-12616203-B2

Abstract

Herbicidal compositions are described containing either 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (2,4-DC) or 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (2,5-DC). Compositions containing 2,4-DC or 2,5-DC and a second herbicide are also disclosed, where the combination does not contain both 2,4-DC and 2,5-DC. Methods of using the same compositions are also described.

Inventors

James Walter
Paul Nicholson
Alison Burnett
James LAPPIN
Gurinderbir S. Chahal
Sandra L. Shinn
Frank J. D'AMICO, JR.

Assignees

FMC CORPORATION

Dates

Publication Date: 20260505
Application Date: 20150220

Claims (13)

1 . A method of controlling undesired vegetation in a wheat crop comprising applying to the locus of said vegetation an herbicidally-effective amount of a composition comprising a first herbicide 2-(2,4-dichlorophenyl) methyl-4,4-dimethyl-3-isoxazolidinone (“2,4-DC”) and optionally at least a second herbicide, and agriculturally acceptable salts or esters thereof, the second herbicide being selected from the group consisting of: bromoxynil, diflufenican, metsulfuron-methyl, napropamide, pyroxasulfone, thifensulfuron-methyl, sulfentrazone; and mixtures of the two or more said second herbicide; wherein the first herbicide is applied at a rate of at least 50 g ai/ha and there is no observed phytotoxicity of greater than 10% to the wheat crop 7 to 28 days after treatment (DAT).
2 . The method of claim 1 , wherein said undesired vegetation is selected from the group consisting of annual blue grass, Benghal dayflower, black grass, black night shade, broadleaf signal grass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), common ragweed, corn poppies, field violet, giant foxtail, goose grass, green fox tail, guinea grass, hairy beggarticks, herbicide-resistant black grass, horseweed, Italian rye grass, jimsonweed, johnsongrass (Sorghum halepense), large crabgrass, little seed canary grass, morning glory, Pennsylvania smartweed, pitted morningglory, prickly sida, quack grass, redroot pigweed, shatter cane, sheppard's purse, silky windgrass, sunflower (as weed in potato), wild buckwheat (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), wild pointsettia, yellow foxtail, and yellow nutsedge (Cyperus esculentus).
3 . The method of claim 1 , wherein said optional second herbicide is present in the composition.
4 . The method of claim 3 , wherein said second herbicide, are agriculturally acceptable salts or esters thereof, and is selected from the group consisting of: bromoxynil, diflufenican, metsulfuron-methyl, napropamide, thifensulfuron-methyl and sulfentrazone and mixtures of the two or more said second herbicide.
5 . The method of claim 4 , wherein said second herbicide are agriculturally acceptable salts or esters thereof, and is selected from the group consisting of: napropamide, diflufenican, sulfentrazone, metsulfuron-methyl and thifensulfuron-methyl; and mixtures of the two or more said second herbicide.
6 . The method of claim 4 , wherein said optional second herbicide is absent from the composition.
7 . The method of claim 3 , wherein said second herbicide, are agriculturally acceptable salts or esters thereof, and is selected from the group consisting of: diflufenican, pyroxasulfone and sulfentrazone and mixtures of the two or more said second herbicide.
8 . The method of claim 7 , wherein said second herbicide, are agriculturally acceptable salts or esters thereof, is selected from the group consisting of: pyroxasulfone and sulfentrazone and mixtures of the two said second herbicide.
9 . The method of claim 8 , wherein said second herbicide, are agriculturally acceptable salts or esters thereof, is pyroxasulfone.
10 . A method of controlling undesired vegetation in a wheat crop comprising applying to the locus of said vegetation an herbicidally-effective amount of a composition comprising a first herbicide 2-(2,4-dichlorophenyl) methyl-4,4-dimethyl-3-isoxazolidinone (“2,4-DC”) and at least a second herbicide, and agriculturally acceptable salts or esters thereof, the second herbicide being selected from the group consisting of: diflufenican, napropamide, pyroxasulfone, and sulfentrazone; and mixtures of two or more thereof, wherein there is no observed phytotoxicity of greater than 10% to the wheat crop 7 to 28 days after treatment (DAT).
11 . The method of claim 10 wherein the second herbicide being selected from the group consisting of: diflufenican, pyroxasulfone, and sulfentrazone; and a mixture of the two or more said second herbicide.
12 . The method of claim 11 wherein the second herbicide being selected from the group consisting of: diflufenican and sulfentrazone; and a mixture of the two second herbicide.
13 . The method of claim 11 wherein the second herbicide is pyroxasulfone.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application is a 371 U.S. national phase filing of International Patent Application No. PCT/US 15/16892 filed Feb. 20, 2015, which application claims the benefit of priority of U.S. Provisional Applications No. 61/943,437 filed on Feb. 23, 2014, and 61/951,269 filed on Mar. 11, 2014, the disclosures of all of which are incorporated herein by reference in their entireties. TECHNICAL FIELD The present invention is directed to compositions and uses of at least one 3-isoxazolidinone analog herbicide selected from 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (“2,4-DC”) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (“2,5-DC”), including combinations with a second herbicide. BACKGROUND The protection of crops from undesirable plants known as weeds which can interfere with crop growth and can reduce crop yield has long been a goal in agriculture. One approach which has been taken to achieve this goal is the development of selective herbicides which can control weeds without exhibiting unacceptable phytotoxicity to the crops sought to be protected. More recently, crops have been protected from weeds by genetically modifying the crop to be tolerant to a non-selective herbicide (such as glyphosate or glufosinate) and applying such herbicide over the top of such crops. Unfortunately, this latter approach has led to the evolution of herbicide-ressitant weeds, with the result that there is still a need for a means of selectively controlling undesirable vegetation in crops. U.S. Pat. No. 4,405,357 discloses certain 3-isoxazolidinones which exhibit desirable selective herbicidal activity. Specifically, such compounds are shown to be effective in controlling grassy and broadleaf weed species while leaving legumes, particularly soybeans, unaffected. Among the compounds specifically disclosed in this patent are 2-(2,4-dichlorophenyl) methyl-4,4-dimethyl-3-isoxazolidinone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone. Both such compounds are effective against a number of weeds. However, there is still a need for effective combinations of herbicides to reduce or nullify the injury of the crop plants by using selective formulations while not affecting the herbicidal action on the weeds to be controlled. SUMMARY OF THE INVENTION The present invention addresses such need. The present invention discloses novel compositions for protecting crops from undesirable vegetation. One aspect of the invention is directed to a composition containing a first herbicide selected from the group consisting of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (“2,4-DC”) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (“2,5-DC”); and at least one second herbicide and use thereof in controlling undesirable vegetation which interfere with crop growth. Another aspect of the invention is directed to a composition comprising a herbicide selected from the group consisting of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (“2,4-DC”) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (“2,5-DC”); at least one formulation component selected from the group consisting of adjuvants for an EC formulation, adjuvants for an SC formulation, and adjuvants for a CS formulation; and optionally, one or more additional active ingredients. In at least one aspect of the present invention, the disclosed composition contains either 2,4-DC or 2,5-DC and the second herbicide that is different from the first herbicide, wherein when the first herbicide is 2,4-DC, the second herbicide is not 2,5-DC, and when the first herbicide is 2,5-DC, the second herbicide is not 2,4-DC. In one embodiment, the first herbicide is 2,4-DC. In another embodiment, the first herbicide is 2,5-DC. In another embodiment, the second herbicide is selected from the group consisting of dimethenamid-P, diphenamid, napropamide, napropamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, metolachlor, dimethachlor, S-metolachlor, pretilachlor, benzofluor, cambendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tembotrione, benfuresate, asulam, barban, alloxydim isoxaflutole, dinitramine, dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, fluoronitrofen, fomesafen, imazamethabenz, bromobonil, bromoxynil, methiozolin, monisouron, pyroxasulfone, topramezone, bromofenoxim, clomeprop, 2,4-DEB, etnipromid, clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB, cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, clofop, cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fluazolate, brompyrazon, clopyralid, diflufenican, atrazine, chlorazine, cyanazine, cyprazine, trietazine, indaziflam, ametryn, methoprotryne, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl, sulfentrazone, thi