EA045326B1 - COMPOSITIONS CONTAINING HALAUXIFEN AND OTHER HERBICIDES, AND RELATED METHODS - Google Patents

Abstract

A herbicidal composition comprising (a) a compound of formula (I): wherein X is CH or N, hal is F, Cl or Br, R is methyl or ethyl, and R' is H, methyl or ethyl, or an agriculturally acceptable salt or ester thereof, (b) a second herbicide comprising at least one organophosphorus herbicide, or agriculturally acceptable salts, esters and amides thereof, and/or (c) a third herbicide comprising at least one pyridine-based herbicide, or agriculturally acceptable salts, esters and amides thereof, providing control of undesirable vegetation, for example, in seed-in-the-ground, seed-in-water and transplanted rice, cereal crops, wheat, barley, oat species, rye, sorghum, corn or maize, sugarcane, sunflower, oilseed rapeseed, canola, sugar beet, soybean, cotton, pineapple, vegetable crops, pastures, meadows, rangelands, fallow land, turf grass, tree and vine orchards, aquatic environments, plantation crops, vegetable crops, industrial vegetation management (IVM) or right-of-way (ROW) sites.

Description

Cross reference to related applications

The invention is an international application that claims priority to U.S. Provisional Patent Application No. 62/755069, filed November 2, 2018, entitled Compositions Containing Halauxifen and Other Herbicides and Related Methods, the contents of which are incorporated herein in their entirety. volume by reference.

Field of technology to which the invention relates

Aspects of the present invention provide herbicidal compositions comprising at least one pyridine or pyrimidine carboxylic acid herbicide, a second herbicide and/or a third herbicide, or agriculturally acceptable salts, esters and amides thereof. Also provided herein are methods for controlling unwanted vegetation, including the use of compositions disclosed herein.

State of the art

Protecting crops from weeds and other vegetation that inhibit crop growth is an ongoing challenge in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have created a wide variety of chemicals and chemical compounds that are effective in controlling this unwanted growth. Many types of chemical herbicides are described in the literature, and a large number are used commercially. However, there remains a need for compositions and methods that are effective in controlling unwanted vegetation.

Short description

The first embodiment provided herein includes herbicidal compositions containing a herbicidal effective amount (a) of a compound of formula (I), ppm

wherein X is CH or N, hal is F, Cl or Br, R is methyl or ethyl, and R' is H, methyl or ethyl, or agriculturally acceptable salts, esters and amides thereof; (b) a second herbicide comprising at least one organophosphorus herbicide, or agriculturally acceptable salts, esters and amides thereof and/or (c) a third herbicide comprising at least one pyridine-based herbicide, or acceptable ones thereof from the agricultural point of view of salts, esters and amides.

The second embodiment includes a composition according to the first embodiment, wherein the compound of formula (I) is present in at least one of the following forms: carboxylic acid, carboxylate salt, aralkyl, alkyl ester, unsubstituted benzyl, substituted benzyl, C _{1 -4} alkyl and/or n-butyl ester.

The third embodiment includes a composition in accordance with the first or second embodiment, wherein the second herbicide (b) comprises at least one compound selected from the group consisting of glufosinate, amiprofos-methyl, anilofos, bensulide, bilanaphos, butamiphos, fosamine and piperophos or their agriculturally acceptable salts, esters and amides.

The fourth embodiment includes a composition according to any of the first to third embodiments, wherein the third herbicide (c) comprises at least one compound selected from the group consisting of fluroxypyr, aminopyralid, cliodinate, clopyralid, dithiopyr, haloxidin, pychloram and thiazopyr or their agriculturally acceptable salts, esters and amides.

A fifth embodiment includes a composition according to any of the first to fourth embodiments, wherein the second herbicide in the composition is glufosinate or agriculturally acceptable salts, esters and amides thereof, wherein the weight ratio of the compound of formula (I) to glufosinate is or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha (grams of acid equivalent per hectare) and g a. i./ha (grams of active ingredient per hectare) or g eq. k./ha and g eq. k./ha, ranges from approximately 1:1000 to approximately 1:1, from approximately 1:500 to approximately 1:1, from approximately 1:400 to approximately 1:1, from approximately 1:300 to approximately 1:1, from about 1:200 to about 1:1, from about 1:100 to about 1:1, from about 1:90 to about 1:1, from about 1:80 to about 1:1, from about 1:70 to about 1:1, about 1:60 to about 1:1, about 1:50 to about 1:1, about 1:40 to about 1:1, about 1:30 to about 1 045326 about 1 :1, from about 1:25 to about 1:1, from about 1:20 to about 1:1, from about 1:13 to about 1:1, from about 1:12.5 to about 1:1, from about 1:10 to about 1:1, about 1:9 to about 1:1, about 1:8 to about 1:1, about 1:7 to about 1:1, about 1:6 to about 1:1, from about 1:5 to about 1:1, from about 1:4 to about 1:1, from about 1:3 to about 1:1, from about 1:2 to about 1:1, from about 1:1 to approximately 1:1, approximately 1:1, approximately 1:2, approximately 1:4, approximately 1:5, approximately 1:10, approximately 1:12.5, approximately 1:25, approximately 1:50 , about 1:100, about 1:150, about 1:200, about 1:250, about 1:300, about 1:350, about 1:400, about 1:450, about 1:500, or any combination thereof .

A sixth embodiment includes a composition according to any of embodiments one through five, wherein the second herbicide in the composition is glufosinate or agriculturally acceptable salts, esters and amides thereof, wherein the weight ratio of the compound of formula (I) to glufosinate is or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha or g eq. k./ha, selected from a group of ratio ranges, the ratios being from about 1:400 to about 1:12.5, from about 1:400 to about 1:25, from about 1:400 to about 1:50, from about 1:400 to about 1:100, from about 1:400 to about 1:200, from about 1:200 to about 1:12.5, from about 1:200 to about 1:50, from about 1: 200 to about 1:100, from about 1:100 to about 1:12.5, from about 1:100 to about 1:50, from about 1:50 to about 1:12.5, from about 1:50 to about 1:25, about 1:25 to about 1:12.5, or any combination thereof.

The seventh embodiment includes a composition according to any of the first to sixth embodiments, wherein the third herbicide in the composition is fluroxypyr or agriculturally acceptable salts, esters and amides thereof, wherein the weight ratio of the compound of formula (I) to fluroxypyr or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha and g eq. k./ha, ranges from approximately 1:200 to approximately 1:1, from approximately 1:100 to approximately 1:1, from approximately 1:90 to approximately 1:1, from approximately 1:80 to approximately 1:1, from about 1:70 to about 1:1, from about 1:60 to about 1:1, from about 1:50 to about 1:1, from about 1:40 to about 1:1, from about 1:35 to about 1:1, about 1:30 to about 1:1, about 1:20 to about 1:1, about 1:10 to about 1:1, about 1:8.8 to about 1:1 , from about 1:8.75 to about 1:1, from about 1:5 to about 1:1, from about 1:4.5 to about 1:1, from about 1:4.4 to about 1:1 , from about 1:4.3 to about 1:1, from about 1:4 to about 1:1, from about 1:3 to about 1:1, from about 1:2.5 to about 1:1, from about 1:2.2 to about 1:1, about 1:2 to about 1:1, about 1:1 to about 1:1, about 1:70, about 1:35, about 1:17.5 , approximately 1:8.8, approximately 1:8.75, approximately 1:4.4, approximately 1:4.38, 1:4.3, approximately 1:2.5, approximately 1:2.2 or provides any combination of them.

The eighth embodiment includes a composition according to any of the first to seventh embodiments, wherein the third herbicide in the composition is fluroxypyr or agriculturally acceptable salts, esters and amides thereof, wherein the weight ratio of the compound of formula (I) to fluroxypyr is or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha and g eq. k./ha, ranges from approximately 1:70 to approximately 1:2.2, from approximately 1:70 to approximately 1:2.2, from approximately 1:70 to approximately 1:4.38, from approximately 1:70 to about 1:4.4, from about 1:70 to about 1:8.8, from about 1:70 to about 1:8.75, from about 1:70 to about 1:17.5, from about 1 :70 to about 1:35, from about 1:35 to about 1:2.2, from about 1:35 to about 1:4.38, from about 1:35 to about 1:4.4, from about 1 :35 to about 1:8.8, about 1:35 to about 1:8.75, about 1:35 to about 1:17.5, about 1:17.5 to about 1:2.2 , from about 1:17.5 to about 1:4.4, from about 1:17.5 to about 1:8.8, from about 1:17.5 to about 1:8.75, from about 1: 8.8 to about 1:2.2, about 1:8.8 to about 1:4.4, about 1:8.8 to about 1:8.75, or any combination thereof.

The ninth embodiment includes a composition according to any of the first to eighth embodiments, wherein the composition contains a compound of formula (I), a second herbicide and a third herbicide.

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The tenth embodiment includes a composition according to any of the first to ninth embodiments, wherein the second herbicide and the third herbicide in the composition are glufosinate or agriculturally acceptable salts, esters and amides thereof and fluroxypyr or agriculturally acceptable salts thereof. agricultural salts, esters and amides, wherein the weight ratio of the compound of formula (I) or its agriculturally acceptable salts, esters and amides, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha and g eq. k./ha, ranges from 1:1000:100 to approximately 1:1:1, from approximately 1:500:80 to approximately 1:1:1, from approximately 1:400:70 to approximately 1:1:1, from about 1:400:70 to about 1:12:2, from about 1:400:70 to about 1:12.5:2.2, from about 1:400:70 to about 1:25:4.4 , from about 1:400:70 to about 1:50:8.8, from about 1:300:70 to about 1:1:1, from about 1:200:70 to about 1:1:1, from about 1:100:70 to about 1:1:1, from about 1:90:70 to about 1:1:1, from about 1:80:70 to about 1:1:1, from about 1:70:70 to about 1:1:1, from about 1:60:70 to about 1:1:1, from about 1:50:70 to about 1:1:1, from about 1:40:70 to about 1:1 :1, from about 1:30:70 to about 1:1:1, from about 1:25:70 to about 1:1:1, from about 1:20:70 to about 1:1:1, from about 1:13:70 to about 1:1:1, from about 1:12,5:70 to about 1:1:1, from about 1:10:70 to about 1:1:1, from about 1:9 :70 to about 1:1:1, from about 1:8:70 to about 1:1:1, from about 1:7:70 to about 1:1:1, from about 1:6:70 to about 1 :1:1, from about 1:5:70 to about 1:1:1, from about 1:2:70 to about 1:1:1, from about 1:1:1 to about 1:1:1, approximately 1:1:1, approximately 1:2:70, approximately 1:4:70, approximately 1:5:70, approximately 1:10:70, approximately 1:12,5:70, approximately 1:25:70 , approximately 1:50:70, approximately 1:100:70, approximately 1:150:70, approximately 1:200:70, approximately 1:250:70, approximately 1:300:70, approximately 1:350:70, approximately 1:400:70, approximately 1:450:70, approximately 1:500:70, or any combination thereof.

The eleventh embodiment includes a composition according to any of the first to tenth embodiments, wherein the second herbicide and the third herbicide in the composition are glufosinate or agriculturally acceptable salts, esters and amides thereof and fluroxypyr or agriculturally acceptable salts thereof. agricultural salts, esters and amides, wherein the weight ratio of the compound of formula (I) or its agriculturally acceptable salts, esters and amides, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha or g eq. k./ha, ranges from 1:1000:35 to approximately 1:1:1, from approximately 1:500:35 to approximately 1:1:1, from approximately 1:400:35 to approximately 1:1:1, from about 1:300:35 to about 1:1:1, from about 1:200:35 to about 1:1:1, from about 1:100:35 to about 1:1:1, from about 1:90 :35 to about 1:1:1, from about 1:80:35 to about 1:1:1, from about 1:70:35 to about 1:1:1, from about 1:60:35 to about 1 :1:1, from about 1:50:35 to about 1:1:1, from about 1:40:35 to about 1:1:1, from about 1:30:35 to about 1:1:1, from about 1:25:35 to about 1:1:1, from about 1:20:35 to about 1:1:1, from about 1:13:35 to about 1:1:1, from about 1:12 .5:35 to about 1:1:1, from about 1:10:35 to about 1:1:1, from about 1:9:35 to about 1:1:1, from about 1:8:35 to about 1:1:1, about 1:7:35 to about 1:1:1, about 1:6:35 to about 1:1:1, about 1:5:35 to about 1:1: 1, from about 1:2:35 to about 1:1:1, about 1:2:35, about 1:4:35, about 1:5:35, about 1:10:35, about 1:12, 5:35, approximately 1:25:35, approximately 1:50:35, approximately 1:100:35, approximately 1:150:35, approximately 1:200:35, approximately 1:250:35, approximately 1:300 :35, approximately 1:350:35, approximately 1:400:35, approximately 1:450:35, approximately 1:500:35, or any combination thereof.

The twelfth embodiment includes a composition according to any of the first through eleventh embodiments, wherein the second herbicide and the third herbicide in the composition are glufosinate or agriculturally acceptable salts, esters and amides thereof and fluroxypyr or agriculturally acceptable salts thereof. agricultural salts, esters and amides, wherein the weight ratio of the compound of formula (I) or its agriculturally acceptable salts, esters and amides, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha and g eq. k./ha, ranges from 1:1000:17.5 to approximately 1:1:1, from approx.

- 3 045326 specifically 1:500:17.5 to approximately 1:1:1, from approximately 1:400:17.5 to approximately 1:1:1, from approximately 1:300:17.5 to approximately 1:1 :1, from about 1:200:17.5 to about 1:1:1, from about 1:100:17.5 to about 1:1:1, from about 1:90:17.5 to about 1: 1:1, from about 1:80:17.5 to about 1:1:1, from about 1:70:17.5 to about 1:1:1, from about 1:60:17.5 to about 1 :1:1, from about 1:50:17.5 to about 1:1:1, from about 1:40:17.5 to about 1:1:1, from about 1:30:17.5 to about 1:1:1, from about 1:25:17.5 to about 1:1:1, from about 1:20:17.5 to about 1:1:1, from about 1:13:17.5 to about 1:1:1, about 1:12.5:17.5 to about 1:1:1, about 1:10:17.5 to about 1:1:1, about 1:9:17 .5 to about 1:1:1, from about 1:8:17.5 to about 1:1:1, from about 1:7:17.5 to about 1:1:1, from about 1:6: 17.5 to about 1:1:1, from about 1:5:17.5 to about 1:1:1, from about 1:2:17.5 to about 1:1:1, about 1:2: 17.5, approximately 1:4:17.5, approximately 1:5:17.5, approximately 1:10:17.5, approximately 1:12.5:17.5, approximately 1:25:17.5 , approximately 1:50:17.5, approximately 1:100:17.5, approximately 1:150:17.5, approximately 1:200:17.5, approximately 1:250:17.5, approximately 1:300 :17.5, approximately 1:350:17.5, approximately 1:400:17.5, approximately 1:450:17.5, approximately 1:500:17.5, approximately 1:2:18, approximately 1 :4:18, approximately 1:5:18, approximately 1:10:18, approximately 1:12,5:18, approximately 1:25:18, approximately 1:50:18, approximately 1:100:18, approximately 1:150:18, approximately 1:200:18, approximately 1:250:18, approximately 1:300:18, approximately 1:350:18, approximately 1:400:18, approximately 1:450:18, approximately 1 :500:18 or provides for any combination thereof.

The thirteenth embodiment includes a composition according to any of the first through twelfth embodiments, wherein the second herbicide and the third herbicide in the composition are glufosinate or agriculturally acceptable salts, esters and amides thereof and fluroxypyr or agriculturally acceptable salts thereof. agricultural salts, esters and amides, wherein the weight ratio of the compound of formula (I) or its agriculturally acceptable salts, esters and amides, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha and g eq. k./ha, ranges from 1:1000:8.8 to approximately 1:1:1, from approximately 1:500:8.8 to approximately 1:1:1, from approximately 1:400:8.8 to approximately 1:1:1, from about 1:300:8.8 to about 1:1:1, from about 1:200:8.8 to about 1:1:1, from about 1:100:8.8 to about 1:1:1, about 1:90:8.8 to about 1:1:1, about 1:80:8.8 to about 1:1:1, about 1:70:8.8 to about 1:1:1, from about 1:60:8.8 to about 1:1:1, from about 1:50:8.8 to about 1:1:1, from about 1:40:8, 8 to about 1:1:1, from about 1:30:8.8 to about 1:1:1, from about 1:25:8.8 to about 1:1:1, from about 1:20:8 .8 to about 1:1:1, from about 1:13:8.8 to about 1:1:1, from about 1:12.5:8.8 to about 1:1:1, from about 1: 10:8.8 to approximately 1:1:1, approximately 1:9:8.8 to approximately 1:1 approximately 1:1 approximately 1:1

1, from about 1:8:8.8 to about 1:1:1, from about 1:7:8.8 to

1, from about 1:6:8.8 to about 1:1:1, from about 1:5:8.8 to

1, from about 1:2:8.8 to about 1:1:1, about 1:2:8.8, at about 1:4:8.8, about 1:5:8.8, about 1: 10:8.8, approximately 1:12.5:8.8, approximately 1:25:8.8, approximately 1:50:8.8, approximately 1:100:8.8, approximately 1:150:8 ,8, approximately 1:200:8.8, approximately 1:250:8.8, approximately 1:300:8.8, approximately 1:350:8.8, approximately 1:400:8.8, approximately 1 :450:8.8, approximately 1:500:8.8, approximately 1:2:9, approximately 1:4:9, approximately 1:5:9, approximately 1:10:9, approximately 1:12.5 :9, approximately 1:25:9, approximately 1:50:9, approximately 1:100:9, approximately 1:150:9, approximately 1:200:9, approximately 1:250:9, approximately 1:300: 9, approximately 1:350:9, approximately 1:400:9, approximately 1:450:9, approximately 1:500:9, or any combination thereof.

The fourteenth embodiment includes a composition according to any of the first to thirteenth embodiments, wherein the second herbicide and the third herbicide in the composition are glufosinate or agriculturally acceptable salts, esters and amides thereof, and fluroxypyr or agriculturally acceptable salts thereof. agricultural salts, esters and amides, wherein the weight ratio of the compound of formula (I) or its agriculturally acceptable salts, esters and amides, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha and g eq. k./ha, ranges from 1:1000:4.4 to approximately 1:1:1, from approximately 1:500:4.4 to approximately 1:1:1, from approximately 1:400:4.4 to approximately 1:1:1, from about 1:300:4.4 to about 1:1:1, from about 1:200:4.4 to about 1:1:1, from about 1:100:4.4 to approximately 1:1:1, approximately 1:90:4.4 to approximately 1:1:1, approximately

- 4 045326 approximately 1:80:4.4 to approximately 1:1:1, from approximately 1:70:4.4 to approximately 1:1:1, from approximately 1:60:4.4 to approximately 1:1 :1, from about 1:50:4.4 to about 1:1:1, from about 1:40:4.4 to about 1:1:1, from about 1:30:4.4 to about 1: 1:1, from about 1:25:4.4 to about 1:1:1, from about 1:20:4.4 to about 1:1:1, from about 1:13:4.4 to about 1 :1:1, from about 1:12.5:4.4 to about 1:1:1, from about 1:10:4.4 to about 1:1:1, from about 1:9:4.4 to about 1:1:1, from about 1:8:4.4 to about 1:1:1, from about 1:7:4.4 to about 1:1:1, from about 1:6:4, 4 to about 1:1:1, from about 1:5:4.4 to about 1:1:1, from about 1:2:4.4 to about 1:1:1, about 1:2:4, 4, approximately 1:4:4.4, approximately 1:5:4.4, approximately 1:10:4.4, approximately 1:12.5:4.4, approximately 1:25:4.4, approximately 1:50:4.4, approximately 1:100:4.4, approximately 1:150:4.4, approximately 1:200:4.4, approximately 1:250:4.4, approximately 1:300:4 ,4, approximately 1:350:4.4, approximately 1:400:4.4, approximately 1:450:4.4, approximately 1:500:4.4, approximately 1:2:5, approximately 1:4 :5, approximately 1:5:5, approximately 1:10:5, approximately 1:12.5:5, approximately 1:25:5, approximately 1:50:5, approximately 1:100:5, approximately 1: 150:5, approximately 1:200:5, approximately 1:250:5, approximately 1:300:5, approximately 1:350:5, approximately 1:400:5, approximately 1:450:5, approximately 1:500 :5 or any combination thereof.

The fifteenth embodiment includes a composition according to any of the first to fourteenth embodiments, wherein the second herbicide and the third herbicide in the composition are glufosinate or agriculturally acceptable salts, esters and amides thereof, and fluroxypyr or agriculturally acceptable salts thereof. agricultural salts, esters and amides, wherein the weight ratio of the compound of formula (I) or its agriculturally acceptable salts, esters and amides, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides, given in units of g eq. k./ha and g a. i./ha or g eq. k./ha and g eq. k./ha, ranges from 1:1000:2.2 to approximately 1:1:1, from approximately 1:500:2.2 to approximately 1:1:1, from approximately 1:400:2.2 to approximately 1:1:1, from about 1:300:2.2 to about 1:1:1, from about 1:200:2.2 to about 1:1:1, from about 1:100:2.2 to about 1:1:1, about 1:90:2.2 to about 1:1:1, about 1:80:2.2 to about 1:1:1, about 1:70:2.2 to about 1:1:1, from about 1:60:2.2 to about 1:1:1, from about 1:50:2.2 to about 1:1:1, from about 1:40:2, 2 to about 1:1:1, from about 1:30:2.2 to about 1:1:1, from about 1:25:2.2 to about 1:1:1, from about 1:20:2 ,2 to about 1:1:1, from about 1:13:2.2 to about 1:1:1, from about 1:12.5:2.2 to about 1:1:1, from about 1: 10:2.2 to about 1:1:1, from about 1:9:2.2 to about 1:1:1, from about 1:8:2.2 to about 1:1:1, from about 1 :7:2.2 to about 1:1:1, from about 1:6:2.2 to about 1:1:1, from about 1:5:2.2 to about 1:1:1, from about 1:2:2.2 to approximately 1:1:1, approximately 1:2:2.2, approximately 1:4:2.2, approximately 1:5:2.2, approximately 1:10:2.2 , approximately 1:12.5:2.2, approximately 1:25:2.2, approximately 1:50:2.2, approximately 1:100:2.2, approximately 1:150:2.2, approximately 1 :200:2.2, approximately 1:250:2.2, approximately 1:300:2.2, approximately 1:350:2.2, approximately 1:400:2.2, approximately 1:450:2, 2, approximately 1:500:2.2, approximately 1:2:2, approximately 1:4:2, approximately 1:5:2, approximately 1:10:2, approximately 1:12.5:2, approximately 1 :25:2, approximately 1:50:2, approximately 1:100:2, approximately 1:150:2, approximately 1:200:2, approximately 1:250:2, approximately 1:300:2, approximately 1: 350:2, approximately 1:400:2, approximately 1:450:2, approximately 1:500:2, or any combination thereof.

The sixteenth embodiment includes a composition according to any of the first to fifteenth embodiments, wherein the compound of formula (I) is halauxifene methyl, glufosinate or agriculturally acceptable salts thereof, esters and amides are glufosinate ammonium, and fluroxypyr or its agriculturally acceptable salts, esters and amides are fluroxypyr-meptyl.

The seventeenth embodiment includes a composition according to any of the first to sixteenth embodiments, wherein the composition further comprises at least one agriculturally acceptable excipient, carrier and/or antidote.

The eighteenth embodiment includes a composition in accordance with any of the first to seventeenth embodiments, wherein the composition further comprises at least one additional herbicide.

A nineteenth embodiment includes a method of controlling unwanted vegetation, comprising the step of applying to vegetation and/or soil and/or water or bringing them into contact by another method with a herbicidally effective amount of at least one composition in accordance with any embodiment with first to seventeenth.

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The twentieth embodiment includes the method in accordance with the nineteenth embodiment, where the method is applied to at least one representative from the group consisting of soil-sown rice, water-sown rice and/or seedling rice, cereal crops, wheat , barley, types of oats, rye, sorghum, corn/maize, sugar cane, sunflower, oilseed rape, canola, sugar beets, soybeans, cotton, pineapple, pastures, meadows, pastures, fallow land, lawn grass, tree and vineyards , aquatic environments, plantation crops, vegetable crops, industrial vegetation control (IVM) or right-of-way (ROW).

The twenty-first embodiment includes the method of the nineteenth and/or twentieth embodiments, wherein a herbicidally effective amount of the composition is applied either pre-emergence or post-emergence to at least one of a crop, a field, a ROW, or a rice crop. field.

The twenty-second embodiment includes the method of any embodiment nineteen through twenty-one, wherein control of unwanted vegetation can be achieved in crops tolerant to glyphosate, 5-enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitor, glufosinate, glutamine synthetase inhibitor, dicamba , phenoxyauxin, pyridyloxyauxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl-CoA carboxylase (ACCase) inhibitor, imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazole inone, an inhibitor of acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS), 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule assembly inhibitor, very long chain fatty acid biosynthesis inhibitor, fatty acid and lipid biosynthesis inhibitor, photosystem inhibitor I, photosystem II inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, triazine, or bromoxynil.

The twenty-third embodiment includes a method according to any of the nineteenth to twenty-second embodiments, wherein a plant that is resistant or tolerant to at least one herbicide is treated, and wherein the resistant or tolerant crop has multiple or stacked tolerance-conferring traits. to multiple herbicides or inhibitors with multiple mechanisms of action, and in some embodiments, the treated plant that exhibits resistance or tolerance to the herbicide is itself undesirable vegetation.

The twenty-fourth embodiment includes the method of any of embodiments nineteen through twenty-three, wherein the resistant or tolerant weed is a biotype that is resistant or tolerant to multiple herbicides, multiple classes of chemicals, inhibitors with multiple mechanisms of herbicidal action , or due to several resistance mechanisms.

The twenty-fifth embodiment includes a method according to any of the nineteenth to twenty-four embodiments, wherein the undesirable plant with resistance or tolerance is a biotype that is resistant or tolerant to at least one or more mechanisms of action provided by herbicides consisting of inhibitors acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl-CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvyl shikimate 3phosphate (EPSP) synthase inhibitors, assembly inhibitors microtubules, fatty acid and lipid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) biosynthesis inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, mitosis inhibitors , cellulose biosynthesis inhibitors, herbicides with several mechanisms of action, quinclorac, arylaminopropionic acids, difenzoquat, endothal or organoarsenic compounds.

The twenty-fifth embodiment includes a method for controlling unwanted vegetation, comprising the step of applying a herbicidal effective amount of at least one compound according to any of the first to eighteenth embodiments, wherein the amount of the composition applied at a rate expressed in ha. i./ha or g eq. k./ha of a compound of formula (I) or its agriculturally acceptable salts, esters and amides is approximately: 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10 g a. i./ha or g eq. k./ha or provides for any combination thereof.

The twenty-sixth embodiment includes the method according to the twenty-fifth embodiment, wherein the amount of the composition applied at a rate expressed in g a. i./ha or

- 6 045326 g eq. k/ha of glufosinate or its agriculturally acceptable salts, esters and amides is approximately: 1, 5, 10, 25, 50, 100, 150, 200, 250, 300, 350, 400, 450, 500 and 1000 g a.

i./ha or g eq. k./ha or provides for any combination thereof.

The twenty-sixth embodiment includes the method in accordance with the twenty-fifth and/or twenty-sixth embodiments, wherein the amount of the composition applied at a rate expressed in g a. i./ha or g eq. k/ha of fluroxypyr or its agriculturally acceptable salts, esters and amides is approximately: 1, 2, 2.2, 2.5, 4, 4.4, 4.5, 5, 8, 8 ,8, 9, 10, 17.5, 35, 70, 100 and 200 g a. i./ha or g eq. k./ha or provides for any combination thereof.

The twenty-seventh embodiment includes the method of any of the nineteenth to twenty-sixth embodiments, wherein the controlled plant is at least one plant comprising Abutilon theophrasti Medik (ABUTH), Amaranthus rudis Sauer, (AMATA) , Chenopodium album L. (pigweed, CHEAL), Polygonum convolvulus L. (convolvulus knotweed, POLCO), Sinapis arvensis L. (field mustard, SINAR) and/or at least one species of Conyza. In these embodiments, the at least one Conyza species includes, but is not limited to, Conyza sumatrensis (ERISU), Conyza canadensis (ERICA), Conyza bonariensis (ERIBO), or other related conyza spp. ERISS).

The twenty-eighth embodiment includes a method for controlling unwanted vegetation, which includes bringing the vegetation or its habitat into contact with the composition according to any of the first to eighteenth embodiment or applying it to soil or water to prevent the emergence or growth of vegetation.

The twenty-ninth embodiment includes the method according to any of the nineteenth to twenty-eighth embodiments where the unwanted vegetation is immature.

The thirtieth embodiment includes the method according to any nineteenth to twenty-ninth embodiment, wherein the composition according to any first to eighteenth embodiment is applied to water.

The thirty-first embodiment includes the method according to any embodiment nineteen to thirty, wherein the composition according to any embodiment one to eighteen is applied pre-emergence to the crop or growing zone.

The thirty-second embodiment includes the method according to any nineteenth to thirty-first embodiment, wherein the composition according to any first to eighteenth embodiment is applied post-emergence to the crop or growing zone.

The thirty-third embodiment includes the method of any of embodiments nineteen through thirty-two, wherein the hardy crop has multiple or stacked traits conferring tolerance to multiple herbicides or multiple modes of action.

Detailed description

Although the teachings of the present invention have been illustrated and described in detail in the figures and description herein, the teachings in the figures and description thereof are to be considered as illustrative and not limiting in nature; It is understood, however, that only illustrative embodiments are shown and described and that all changes and modifications that fall within the spirit of the disclosure are intended to be protected.

Definitions

Unless otherwise indicated, scientific and technological nomenclature have the same meaning as commonly understood by one skilled in the art pertaining to the present invention.

As used herein, unless expressly stated or otherwise implied, the expression approximately refers to a range of values plus or minus 10 percent, for example, approximately 1.0 covers values from 0.9 to 1.1.

The compound of formula (I) as used herein has the following structure:

where X is CH or N, hal is F, Cl or Br, R is methyl or ethyl, and R' is H, methyl or ethyl, or agriculturally acceptable salts thereof, complex esters and amides. Unless otherwise expressly stated or clearly implied, a compound of formula (I) may include, without limitation, halauxifen or halauxifen-methyl.

As used herein, halauxifene-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3methoxyphenyl)picolinate) has the following structure:

This compound is described in US Pat. No. 7,314,849 B2, which is incorporated herein by reference in its entirety. Exemplary uses of halauxifen-methyl include its use for the control of broadleaf weeds, such as in cereal crops. Galauxifen-methyl can be used in other forms, for example, halauxifen K+ (potassium 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl) picolinate), which has the following structure:

The pyridine or pyrimidine carboxylic acids of formula (I) as used herein may include derivatives of the pyridine or pyrimidine carboxylic acids of formula (I) as 4-amino-3chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine- 2-carboxylic acid and 6-amino-5-chloro-2-(4-chloro-2fluoro-3-methoxyphenyl)-pyrimidine-4-carboxylic acid. Exemplary uses of a compound of formula (I) include the control of undesirable vegetation, including, for example, grasses, broadleaf and sedge weeds, in non-crop and multi-rotation crops.

As used herein, glufosinate is 2-amino-4[hydroxy(methyl)phosphinoyl]butyric acid. An exemplary form of glufosinate is glufosinate ammonium, that is, the ammonium salt of glufosinate. It may be referred to as the monoammonium salt of 2-amino-4-(hydroxymethylphosphinyl)butanoic acid and has the following structure:

Other chemical forms of glufosinate (or phosphinothricin) include bialaphos, which is 2-amino-4-(methylphosphino)butyrylalanylalanine and has the following structure:

Bialaphos can also be used in salt form such as bialaphos sodium. Exemplary applications are described in Tomlin, C., and ed. A World Compendium The Pesticide Manual. 15th ed. Alton: BCPC Publications, 2009 (hereinafter referred to in this document as The Pesticide Manual, Fifteenth Edition, 2009). Exemplary uses include the use of the compound to control annual and perennial broadleaf weeds and grass weeds. Other chemical forms include glufosinate-P, i.e. S-2-amino-4-[hydrokCi(methyl)phosphinoyl]butyric acid.

Fluroxypyr as used herein is 2-[(4-amino-3,5-dichloro-6fluoro-2-pyridinyl)oxy]acetic acid and has the following structure:

- 8 045326

Exemplary uses of fluroxypyr are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fluroxypyr include its use for post-emergence foliar application to control broadleaf weeds, such as in small grain crops, to control Rumex spp. and Urtilca dioica in pastures and for the control of Trifolium repens in ornamental meadows. Other exemplary uses include the use of the compound for the control of herbaceous and woody broadleaf weeds, such as in gardens and plantations, and broadleaf shrubs, such as in coniferous forests. Exemplary chemical forms of fluroxypyr include, for example, fluroxypyr methylheptyl ester (also known as fluroxypyr-meptyl), which is 1-methylheptyl-2-[(4amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy] acetate and has the following structure:

As used herein, herbicide means a compound, such as an active ingredient, that kills, controls, or otherwise adversely modifies plant growth.

As used herein, a herbicidally effective amount or a sufficient amount to control vegetation is an amount of the active ingredient that causes an adverse modifying effect on vegetation, e.g., aberration, killing, control, moisture loss, growth retardation, etc. .P.

In the context of this document, control of undesirable vegetation means the prevention, weakening, destruction or other adverse modification of the development of plants and vegetation. This document describes methods for controlling unwanted vegetation through the use of certain combinations of herbicides or compositions based thereon. Applications include, but are not limited to, applications to vegetation or its habitat, such as application to an area adjacent to vegetation, as well as pre-emergent, post-emergent, foliar (broadcast, directed, band, hole, mechanized, aerial, or emergency) applications. and water applications (for fully or partially submerged vegetation, broadcast, in holes, mechanized, injected into water, broadcast for granules, in granule holes, by aerosol mixer or spray) using hand, backpack, machine, tractor or aviation (plane and helicopter) methods of application.

As used herein, plants and vegetation include, but are not limited to, germinating seeds, emerging seedlings, plants developing from vegetative cuttings, immature vegetation, and mature vegetation.

As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity or that are or can be converted in plants, water or soil into the herbicide mentioned. Exemplary agriculturally acceptable esters are those esters that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, for example, in plants, water, or soil, to the corresponding carboxylic acid, which Depending on pH, it can be in dissociated or undissociated form.

Exemplary salts include salts derived from alkali or alkaline earth metals, and salts derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium and ammonium cations according to the formula

R^R^Nb, where each R ¹ , R ² , R ³ and R ⁴ independently represents hydrogen or C ₁ -C ₁₂ -alkyl, C3 -C12 -alkenyl or C ₃ -C ₁₂ -alkynyl, each of which is optionally substituted with one or several hydroxy, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio or phenyl groups, provided that R ¹ , R ² , R ³ and R ⁴ are sterically compatible. In addition, any two of R ¹ , R ² , R ³ and R ⁴ together can represent

- 9 045326 an aliphatic bifunctional fragment containing from one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a metal hydroxide such as sodium hydroxide, an amine such as ammonia, trimethylamine, diethanolamine, 2methylthiopropylamine, bis-allylamine, 2-butoxyethylamine, morpholine, cyclododecylamine or benzylamine, or a tetraalkylammonium hydroxide such as tetramethylammonium hydroxide or choline hydroxide .

Exemplary esters include those derived from C1-C12alkyl-, C3- _C12 -alkenyl-, C3- _C12- alkynyl-, or _C7 - _C10 -aryl-substituted alkyl alcohols such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allylic alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with 1-3 substituents independently selected from halogen, C1- _C4 alkyl or C1- _C4 alkoxy. Esters can be prepared by combining acids with alcohol using any number of suitable activating agents, such as those used to form peptide bonds, such as dicyclohexylcarbodiimide (DCC) or carbonyldiimidazole (CDI); by reacting acids with alkylating agents such as alkyl halides or alkyl sulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the acid chloride of the corresponding acid with the corresponding alcohol; by reacting the acid chloride of the corresponding acid with the corresponding alcohol in the presence of an acid catalyst or by a transesterification reaction.

Compositions and methods

Provided herein are herbicidal compositions containing a herbicidal effective amount of (a) a compound of formula (I),

wherein X is CH or N, hal is F, Cl or Br, R is methyl or ethyl, and R' is H, methyl or ethyl, or an agriculturally acceptable salt or ester thereof; (b) a second herbicide comprising at least one organophosphorus herbicide, or agriculturally acceptable salts, esters and amides thereof and/or (c) a third herbicide comprising at least one pyridine-based herbicide, or acceptable ones thereof from the agricultural point of view of salts, esters and amides.

Also provided herein are methods for controlling unwanted vegetation, comprising contacting the vegetation or its habitat, i.e., an area adjacent to the vegetation, with or applying to soil or water to prevent the emergence or growth of vegetation, a herbicidal effective amount of a compound. formula (I) or an agriculturally acceptable salt or ester thereof, (b) a second herbicide comprising at least one organophosphorus herbicide, or an agriculturally acceptable salt, ester and amide thereof and/or (c ) a third herbicide comprising at least one herbicide, or agriculturally acceptable salts, esters and amides thereof. In certain embodiments, the methods employ the compositions described herein.

Additionally, in some embodiments, a combination of a compound of formula (I) or an agriculturally acceptable salt or ester thereof, a second herbicide comprising at least one organophosphorus herbicide, or an agriculturally acceptable salt, ester and amides and/or a third herbicide comprising at least one pyridine-based herbicide, or agriculturally acceptable salts, esters and amides thereof, is more effective than using them alone.

In certain embodiments of the compositions and methods described herein, a compound of formula (I), i.e., halauxifene-methyl, is used. In certain embodiments, the carboxylate salt of the compound of formula (I) is used. In certain embodiments, an aralkyl or alkyl ester is used. In certain embodiments, benzyl, substituted benzyl, or C1 is used. ₄ alkyl, for example n-butyl, esters. In certain embodiments, a benzyl ester is used.

In some embodiments, a compound of formula (I) or a salt or ester thereof, a second herbicide comprising at least one organophosphorus herbicide, or

- 10 045326 agriculturally acceptable salts, esters and amides and/or a third herbicide comprising at least one pyridine-based herbicide, or its agriculturally acceptable salts, esters and amides are formulated in one composition, a tank mixture is obtained from them, used simultaneously or used sequentially.

The compounds exhibit herbicidal activity when applied directly to the plant or to the plant's location at any stage of plant growth. The observed effect depends on the type of plant being controlled, the stage of growth of the plant, the application parameters, namely the dilution and droplet size of the liquid sprayed, the particle size of the solid components, the environmental conditions at the time of application, the specific compound used, the specific excipients and carriers used, the type soil, etc., as well as the amount of chemical used. These and other factors can be adjusted to provide non-selective or selective herbicidal action. In some embodiments, the compositions described herein are applied as post-emergence, pre-emergence, or water applications in flooded rice fields or bodies of water (e.g., ponds, lakes, and streams) against relatively immature unwanted vegetation to achieve maximum control weeds.

In some embodiments, the compositions and methods provided herein are used to control weeds in crops including, but not limited to, soil-seeded rice, water-seeded rice and/or seedling rice, cereals, wheat, barley, spp. oats, rye, sorghum, corn/maize, sugar cane, sunflower, oilseed rape, canola, sugar beets, soybeans, cotton, pineapple, in pastures, meadows, pastures, fallow land, lawn grass, tree and grape orchards, water environments, plantation crops, vegetable crops, industrial vegetation control (IVM) or right-of-way (ROW).

The compositions and methods described herein can be used to control unwanted vegetation in glyphosate-tolerant, 5-enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase inhibitor, dicamba tolerant, phenoxyauxin tolerant, pyridyloxyauxin tolerant, auxin tolerant, auxin tolerant, auxin transport inhibitor tolerant, aryloxyphenoxypropionate tolerant, auxin tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to acetyl-CoA carboxylase (ACCase) inhibitor, tolerant to imidazolinone, tolerant to sulfonylurea, tolerant to pyrimidinyl thiobenzoate, tolerant to thiazolpyrimidine, tolerant to to sulfonylaminocarbonyltriazolinone, tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor, tolerant to 4hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, tolerant to phytoene desaturase inhibitor, tolerant to carotenoid biosynthesis inhibitor, tolerant to protoporphyrinogen oxide inhibitor basics (PPO), cellulose inhibitor tolerant, mitosis inhibitor tolerant, microtubule assembly inhibitor tolerant, very long chain fatty acid biosynthesis inhibitor tolerant, fatty acid and lipid biosynthesis inhibitor tolerant , photosystem I inhibitor-tolerant, photosystem II inhibitor-tolerant, triazine-tolerant, and bromoxynil-tolerant crops (such as, but not limited to, soybeans, cotton, canola/oilseed rape, rice, cereals, corn , sorghum, sunflower, sugar beet, sugar cane, turfgrass, etc.), e.g. in combination with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates , cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors s, mitosis inhibitors, microtubule assembly inhibitors, fatty acid biosynthesis inhibitors very long chain acids, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines and bromoxynil. The compositions and methods can be used in the control of unwanted vegetation in crops having multiple or stacked traits that confer tolerance to multiple chemicals and/or inhibitors with multiple mechanisms of action. In some embodiments, a compound of formula (I), or a salt or ester thereof, and a complementary herbicide, or a salt or ester thereof, is used in combination with herbicides that are selective for the crop being treated and that complement the spectrum of weeds being controlled. with these compounds at the application rate used. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation, as a tank mix, or sequentially.

The compositions and methods can be used in the control of unwanted vegetation in crops having tolerance to agronomic stress (including, but not limited to, drought, cold, heat, salinity, water, nutrients, fertility, pH), tolerance to pests (including, but not limited to insects, fungi and pathogens) and crop improvement traits (including, but not limited to, yield; protein, carbohydrate or oil content; protein, carbohydrate or oil composition; plant structure and plant structure).

The compositions and methods presented herein are used to control unwanted vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in rice, grain crops, wheat, barley, oats, rye, pastures, meadows, pastures, fallow land, row crops (e.g., corn/maize, sugar cane, sunflowers , oilseed rape, canola, sugar beet, soybean, cotton), turfgrass, tree and vineyards, plantation crops, vegetable crops, ornamental species, aquatic environments or non-agricultural plantings (e.g. rights-of-way, vegetation control facilities in industrial areas) .

In some embodiments, the methods presented herein are used to control unwanted vegetation in rice. In certain embodiments, the unwanted vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf branch, BRAPP), Digitaria sanguinalis (L.) Scop. (blood red crabgrass, DIGSA), Echinochloa spp. (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (common barnyard grass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (peacock barnyard, ECHCV), Echinochloa colonum (L.) LINK (peacock barnyard, ECHPH), Echinochloa oryzoides (Ard.) Fritsch (rice barnyard, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (bearded barnyard, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice grass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (multiple wool, ECHPO), Ischaemum rugosum Salisb. (ischemum, ISCRU), Leptochloa chinensis (L.) Nees (LEFCH), Leptochloa fascicularis (Lam.) Gray (LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazonian weedgrass, LEFPA), Oryza spp. (red weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (split-flowered millet, PANDI), Paspalum dilatatum Poir. (expanded buckwheat, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (high rottbelia, ROOEX), Cyperus spp. (CYPSS), Cyperus difformis L. (heterogeneous orchard, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (edible cornwort, CYPES), Cyperus iria L. (round cornwort, CYPIR), Cyperus rotundus L. (round cornwort, CYPRO), Cyperus serotinus Rottb./C.B.Clarke (late cottonmouth, CYPSE) , Eleocharis spp. (ELOSS), Fimbristylis miliacea (L.) Vahl (fimbristylis, FIMMI), Schoenoplectus spp. (SCPSS), Schoenoplectus juncoides Roxb. (Japanese reed, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. (marine reed, SCPMA), Schoenoplectus mucronatus L. (SCPMU), Aeschynomene species (Virginian pennywort, AESSS), Alternanthera philoxeroides (Mart .) Griseb. (alternanthera phylloxeroides, ALRPH), Alisma plantago-aquatica L. (common chastocha, ALSPA), Amaranthus spp., (chenozematodes and amaranthaceae, AMASS), Ammannia coccinea Rottb. (Ammania benghalensis, AMMCO), Commelina benghalensis L. (COMBE), Eclipta alba (L.) Hassk. (eclipta alba, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (heteranthera muddy, HETLI), Heteranthera reniformis R. & P. (heteranthera reniform, HETRE), Ipomoea spp. (IPOSS), Ipomoea hederacea (L .) Jacque. (Ipomoea ivy, IPOHE), Lindernia dubia (L.) Pennell (LIDDU), Ludwigia spp. (LUDSS), Ludwigia linifolia Poir. (Ludwigia hyssopolis, LUDLI), Ludwigia octovalvis (Jacq.) Raven (Ludwigia octovalvis, LUDOC), Monochoria korsakowii Regel & Maack (monochory, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth (monochory, MOOVA) , Murdannia nudiflora (L.) Brenan (MUDNU), Polygonum pensylvanicum L. (Pennsylvanian knotweed, POLPY), Polygonum persicaria L. (POLPE), Polygonum hydropiperoides Michx. (POLHP), Rotala indica (Willd.) Koehne (ROTIN), Sagittaria spp. (SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (sesbania tall, SEBEX) or Sphenoclea zeylanica Gaertn. (Sphenoclea ceylonensis, SPDZE).

In some embodiments, the methods presented herein are used to control unwanted vegetation in crops. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. (foxtail mousetail, ALOMY), Apera spica-venti (L.) Beauv. (common broom, APESV), Avena fatua L. (empty oats, AVEFA), Bromus tectorum L. (brome, BROTE), Lolium multiflorum Lam. (multiflora tares, LOLMU), Phalaris minor Retz. (small canary grass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J.A. Schultes (low bristle grass, SETLU), Setaria viridis (L.) Beauv. (green bristles, SETVI), Amaranthus retroflexus (upturned amaranth,

- 12 045326

AMARE), Brassica spp. (BRSSS), Chenopodium album L. (pigweed, CHEAL), Cirsium arvense (L.) Scop. (field thistle, CIRAR), Galium aparine L. (grass bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple lily, LAMPU), Matricaria recutita L. (chamomile, MATCH), Matricaria matricarioides (Less.) Porter (fragrant chamomile, MATMT), Papaver rhoeas L. (samosa poppy, PAPRH), Polygonum convolvulus L. (convolvulus, POLCO), Salsola tragus L. (Russian solyanka, SASKR), Sinapis species (SINSS), Sinapis arvensis (field mustard, SINAR), Stellaria media (L.) Vill. (chickweed, STEME), Veronica persica Poir. (Veronica Persica, VERPE), Viola arvensis Murr. (field violet, VIOAR) or Viola tricolor L. (tricolor violet, VIOTR).

In some embodiments, the methods presented herein are used to control unwanted vegetation in pastures and pastures, fallow land, IVM and ROW. In certain embodiments, the unwanted vegetation is Ambrosia artemisiifolia L. (ambrosia ragweed, AMBEL), Cassia obtusifolia (senna obtusifolia, CASOB), Centaurea maculosa auct. non Lam. (spotted cornflower, CENMA), Cirsium arvense (L.) Scop. (field thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (spurge, EPHES), Lactuca serriola L./Torn. (wild lettuce, LACSE), Plantago lanceolata L. (plantain, PLALA), Rumex obtusifolius L. (sorrel, RUMOB), Sida spinosa L. (sedum, SIDSP), Sinapis arvensis L. (field mustard, SINAR) , Sonchus arvensis L. (Sow thistle, SONAR), Solidago spp. (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (common dandelion, TAROF), Trifolium repens L. (creeping clover, TRFRE) or Urtica dioica L. (nettle, URTDI).

In some embodiments, the methods presented herein are used to control unwanted vegetation that occurs in row crops, tree crops, vine crops, and perennial crops. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. (Mousetail foxtail, ALOMY), Avena fatua L. (Empty oats, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (branchwort, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (brachiaria palisade, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf branch, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (BRAPL), Cenchrus echinatus L. (CENEC), Digitaria horizontalis Willd. (horizontal crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (island crabgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (blood red crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (common barnyard grass, ECHCG), Echinochloa colonum (L.) Link (barnyard grass, ECHCO), Eleusine indica (L.) Gaertn. (Eleusina indica, ELEIN), Lolium multiflorum Lam. (multiflora tares, LOLMU), Panicum dichotomiflorum Michx. (forked millet, PANDI), Panicum miliaceum L. (common millet, PANMI), Setaria faberi Herrm. (Faber's bristleweed, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Aleppo sorghum, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (grass sorghum, SORVU), Cyperus esculentus L. (edible sorghum, CYPES), Cyperus rotundus L. (round sorghum, CYPRO), Abutilon theophrasti Medik. (Theophrastus's rope, ABUTH), Amaranthus spp. (Chenopodiaceae and amaranthaceae, AMASS), Ambrosia artemisiifolia L. (Ambrosia wormwood, AMBEL), Ambrosia psilostachya DC. (ragweed, AMBPS), Ambrosia trifida L. (ambrosia tripartite, AMBTR), Anoda cristata (L.) Schlecht. (anode comb, ANVCR), Asclepias syriaca L. (Syrian cottonweed, ASCSY), Bidens pilosa L. (hairy comb, BIDPI), Borreria spp. (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (boreria winged, BOILF), Spermacose latifolia (boreria winged, BOILF), Chenopodium album L. (white pigweed, CHEAL), Cirsium arvense (L.) Scop. (field thistle, CIRAR), Commelina benghalensis L. (COMBE), Datura stramonium L. (Datura stramonium, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (spurge, EPHHL) , Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (Spurge spurge, EPHHI), Euphorbia dentata Michx. (spurge spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (ERIBO), Erigeron sumatrensis or Conyza sumatrensis (ERISU), Erigeron canadensis L. or Conyza canadensis (ERICA) or other related species (Conyza spp, ERISS), Helianthus annuus L. (sunflower common, HELAN), Jacquemontia tamnifolia (L.) Griseb. (Jakemontia tamnifolia, IAQTA), Ipomoea hederacea (L.) Jacq. (Ipomoea ivy, IPOHE), Ipomoea lacunosa L. (Ipomoea pitta, IPOLA), Lactuca serriola L./Torn. (wild lettuce, LACSE), Portulaca oleracea L. (POROL), Richardia spp., RCHSS, Sida spp., SIDSS, Sida spinosa L. (SIDSP), Sinapis arvensis L. ( field mustard, SINAR), Solanum ptychanthum Dunal (SOLPT), Tridax procumbens L. (TRQPR) or Xanthium strumarium L. (XANST).

In some embodiments, the methods presented herein are used to control unwanted vegetation in turfgrass. In certain embodiments, the unwanted vegetation is Bellis perennis L. (BELPE), Cyperus esculentus L. (CYPES), Cyperus spp. (CYPSS), Digitaria sanguinalis (L.)

- 13 045326

Scop. (blood red crabgrass, DIGSA), Diodia virginiana L. (DIQVI), Euphorbia spp. (Euphorbia, EPHSS), Glechoma hederacea L. (GLEHE), Hydrocotyle umbellata L. (money, HYDUM), spp. Kyllinga (KYLSS), Lamium amplexicaule L. (LAMAM), Murdannia nudiflora (L.) Brenan (MUDNU), Oxalis species (Oxalis, OXASS), Plantago major L. (Plantain, PLAMA) , Plantago lanceolata L. (PLALA), Phyllanthus urinaria L. (PYLTE), Rumex obtusifolius L. (RUMOB), Stachys floridana Shuttlew. (Florida chickweed, STAFL), Stellaria media (L.) Vill. (Starweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (common dandelion, TAROF), Trifolium repens L. (creeping clover, TRFRE) or Viola spp. (tricolored violet, VIOSS).

In some embodiments, the compositions provided herein are used to control unwanted vegetation, including grasses, broadleaf and sedge weeds. In certain embodiments, the compositions and methods presented herein are used to control unwanted vegetation, including, but not limited to, Alopecurus, Avena, Centaurea, Cyperus, Digitaria, Echinochloa, Ipomoea, Leptochloa, and Sonchus.

In some embodiments, a combination of a compound of formula (I) or an agriculturally acceptable salt or ester thereof, a second herbicide comprising at least one organophosphorus herbicide, or an agriculturally acceptable salts, esters and amides thereof, and/ or a third herbicide comprising at least one pyridine-based herbicide, or agriculturally acceptable salts, esters and amides thereof, is used to control Abutilon theophrasti Medik. (Theophrastus's rope, ABUTH), Amaranthus rudis Sauer (tuberculous acorn, AMATA), Chenopodium album L. (white pigweed, CHEAL), Polygonum convolvulus L. (convolvulus, POLCO), Sinapis arvensis L. (field mustard, SINAR) and /or at least one of the Conyza species, including, but not limited to, Conyza sumatrensis (ERISU), Conyza canadensis (ERICA), Conyza bonariensis (ERIBO) or other related species (Conyza spp, ERISS) .

The compounds of formula (I) or an agriculturally acceptable salt or ester thereof can be used to control weeds with herbicide resistance or tolerance. Methods that use a combination of a compound of formula (I) or an agriculturally acceptable salt or ester thereof and the compositions described herein can also be used to control weeds with herbicide resistance or tolerance. Exemplary weeds with resistance or tolerance include, but are not limited to, biotypes with resistance or tolerance to acetolactate synthase (ALS) or acetohydroxyacid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, and sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., ilcarbamatam, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl-CoA carboxylase (ACCase) inhibitors (e.g. aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g. benzoic acids, phenoxycarboxylic acids , pyridinecarbonic acids, quinolinecarboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums), 5-enolpyruvylshikimate 3-phosphate synthase (EPSP) inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialaphos), microtubule assembly inhibitors (e.g. benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g. carbamates), very long chain fatty acid (VLCFA) biosynthesis inhibitors (e.g. acetamides, chloroacetamides, hydroxyacetamides, tetrazolinones ), fatty acid and lipid biosynthesis inhibitors (e.g. phosphorodithioates, thiocarbamates, benzofurans, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g. acifluorfen, acifluorfen sodium, azaphenidine, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone -ethyl , chlomethoxifen, cynidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycophen, fluoroglycophen-ethyl, flutiacet, flutiacet-methyl, fomesafen, halosafen, ipfencarbazone, varnish tofen, oxadiargyl, oxadiazone, oxyfluorfen, pentoxazone , profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, thiaphenacyl, trifludimoxazine, ethyl-[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4dioxo- 1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-( 2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5methyl-1H-pyrazole-1-carboxamide (CAS 45100-03-7) and 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro2H-benzo[1,4]oxazin-6-yl]-1,5 -dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione; b5) from the discoloration group

- 14 045326 herbicides), carotenoid biosynthesis inhibitors (for example, clomazone, amitrol, aclonifen), phytoene desaturase (PDS) inhibitors (for example, amides, anilidex, furanones, phenoxybutanamides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate dioxygenase inhibitors (HPPD) (e.g. callistemons, isoxazolams, pyrazolams, triketones), cellulose biosynthesis inhibitors (e.g. nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes of action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, diphenzoquat, endothal and organoarsenic compounds. Exemplary weeds with resistance or tolerance include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple classes of chemicals, biotypes with resistance or tolerance to multiple mechanisms of herbicidal action, and biotypes with multiple mechanisms resistance or endurance (for example, endurance towards the target site or metabolic resistance).

In certain embodiments of the compositions and methods described herein, a compound of formula (I) or a salt or ester thereof is used in combination with glufosinate or agriculturally acceptable salts, esters and amides thereof. In some embodiments, the weight ratio of the compound of formula (I) or a salt or ester thereof and glufosinate or agriculturally acceptable salts, esters and amides thereof ranges from about 1:500 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or a salt or ester thereof and glufosinate or agriculturally acceptable salts, esters and amides thereof ranges from about 1:400 to about 1:12.5. In certain embodiments, the weight ratio of the compound of formula (I) or a salt or ester thereof and glufosinate or agriculturally acceptable salts, esters and amides thereof ranges from about 1:200 to about 1:25. In certain embodiments, the compositions provided herein contain a compound of formula (I) or a salt or ester thereof and glufosinate or an ammonium salt thereof. In one embodiment, the composition contains a compound of formula (I) or a salt or ester thereof and glufosinate ammonium, wherein the weight ratio of the compound of formula (I) or a salt or ester thereof and glufosinate ammonium is from about 1:400 to about 1: 12.5 or from about 1:400 to about 1:25. In one embodiment, the composition contains a compound of formula (I) or a salt or ester thereof and glufosinate ammonium, wherein the weight ratio of benzyl ester of the compound of formula (I) or a salt or ester thereof and glufosinate ammonium is from about 1:200 to about 1:12.5 or about 1:200 to about 1:25.

With respect to methods, in certain embodiments, the methods include bringing the composition described herein into contact with or applying to undesirable vegetation or vegetation to soil or water to prevent the emergence or growth of vegetation. In some embodiments, the composition is applied at an application rate of from about 1 gram of acid equivalent per hectare (g eq/ha) to about 400 grams of active ingredient per hectare (g ai/ha) based on total active ingredients in composition. In certain embodiments, the composition is applied at an application rate of from about 4 grams acid equivalent per hectare (g eq/ha) to about 400 g eq. k./ha in terms of the total amount of active ingredients in the composition. In some embodiments, the methods include contacting the unwanted vegetation or site thereof with a compound of formula (I) or a salt or ester thereof and glufosinate, or agriculturally acceptable salts, esters and amides thereof, or a salt or ester thereof. ether or applying them to soil or water to prevent the emergence or growth of vegetation, for example, sequentially or simultaneously. In some embodiments, glufosinate or its agriculturally acceptable salts, esters and amides are used at a rate of about 50 g a. i./ha up to approximately 400 g a. i./ha, and the compound of formula (I) or its salt or ester is used at a rate of about 1 g eq. k./ha up to approximately 4 g eq. k./ha. In some embodiments, glufosinate or its agriculturally acceptable salts, esters and amides are used at rates of about 100 g a. i./ha up to approximately 400 g a. i./ha, and the compound of formula (I) or its salt or ester is used at a rate of about 1 g eq. k./ha up to approximately 4 g eq. k./ha. In some embodiments, glufosinate or its agriculturally acceptable salts, esters and amides are used at a rate of about 200 g a. i./ha up to approximately 400 g a. i./ha, and the compound of formula (I) or its salt or ester is used at a rate of about 1 g eq. k./ha up to approximately 4 g eq. k./ha. In one embodiment, the methods use a compound of formula (I) and glufosinate ammonium, wherein the compound of formula (I) is used at a rate of about 1 g eq. k./ha up to approximately 4 g eq. k./ha, and glufosinate is used at a rate of approximately 50 g a. i./ha up to approximately 400 g a.

- 15 045326

i./ha. In certain embodiments, methods and compositions that use a compound of formula (I) or a salt or ester thereof in combination with glufosinate or a salt or ester thereof are used to control Abutilon theophrasti Medik (ABUTH), Amaranthus rudis Sauer ( AMATA), Chenopodium album L. (CHEAL), Polygonum convolvulus L. (POLCO), Sinapis arvensis L. (SINAR) and/or at least one of the Conyza species, including without limitation Conyza sumatrensis (ERISU), Conyza canadensis (ERICA), Conyza bonariensis (ERIBO) or other related species (Conyza spp, ERISS).

In certain embodiments of the compositions and methods described herein, a compound of formula (I) or a salt or ester thereof is used in combination with fluroxypyr or agriculturally acceptable salts, esters and amides thereof. In some embodiments, the weight ratio of the compound of formula (I) or a salt or ester thereof and fluroxypyr or agriculturally acceptable salts, esters and amides thereof is in the range of from about 1:70 to about 1:1. In certain embodiments, the weight ratio of a compound of formula (I) or a salt or ester thereof and fluroxypyr or agriculturally acceptable salts, esters and amides thereof ranges from about 1:70 to about 1:2.2. In certain embodiments, the weight ratio of the compound of formula (I) or a salt or ester thereof and fluroxypyr or agriculturally acceptable salts, esters and amides thereof ranges from about 1:35 to about 1:8.8. In one embodiment, the composition contains a compound of formula (I) or a salt or ester thereof and fluroxypyrmeptyl, wherein the weight ratio of the compound of formula (I) or a salt or ester thereof and fluroxypyrmeptyl is from about 1:70 to about 1:1 or from about 1:70 to about 1:2.2. In one embodiment, the composition contains a compound of formula (I) or a salt or ester thereof and fluroxypyr-meptyl, wherein the weight ratio of the benzyl ester compound of formula (I) or a salt or ester thereof and fluroxypyr-meptyl is from about 1:35 to about 1:8.8 or about 1:35 to about 1:4.4.

With respect to methods, in certain embodiments, the methods include bringing the composition described herein into contact with or applying to undesirable vegetation or vegetation to soil or water to prevent the emergence or growth of vegetation. In some embodiments, the composition is applied at an application rate of from about 1 gram of acid equivalent per hectare (g eq/ha) to about 70 grams (g eq/ha) based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 4 grams acid equivalent per hectare (g eq/ha) to about 70 g eq. k./ha in terms of the total amount of active ingredients in the composition. In some embodiments, the methods include contacting the unwanted vegetation or site thereof with a compound of formula (I) or a salt or ester thereof and fluroxypyr, or agriculturally acceptable salts, esters and amides thereof, or a salt or ester thereof. ether or applying them to soil or water to prevent the emergence or growth of vegetation, for example, sequentially or simultaneously. In some embodiments, fluroxypyr or its agriculturally acceptable salts, esters and amides are used at a rate of about 8.8 g eq. k./ha up to approximately 70 g eq. k./ha, and the compound of formula (I) or its salt or ester is used at a rate of approximately 1 g eq. k./ha up to approximately 4 g eq. k./ha. In some embodiments, fluroxypyr or its agriculturally acceptable salts, esters and amides are used at a rate of from about 17.5 g eq. k./ha up to approximately 70 g eq. k./ha, and the compound of formula (I) or its salt or ester is used at a rate of approximately 1 g eq. k./ha up to approximately 4 g eq. k./ha. In some embodiments, fluroxypyr or its agriculturally acceptable salts, esters and amides are used at a rate of about 35 g eq. k./ha up to approximately 70 g eq. k./ha, and the compound of formula (I) or its salt or ester is used at a rate of approximately 1 g eq. k./ha up to approximately 4 g eq. k./ha. In one embodiment, the methods use a compound of formula (I) and fluroxypyr-meptyl, wherein the compound of formula (I) is used at a rate of about 1 g eq. k./ha up to approximately 4 g eq. k./ha, and fluroxypyrmeptil is used at a rate of approximately 8.8 g eq. k./ha up to approximately 70 g a. i./ha. In certain embodiments, methods and compositions that use a compound of formula (I) or a salt or ester thereof in combination with a fluoroxypyr or a salt or ester thereof are used to control Abutilon theophrasti Medik (ABUTH), Amaranthus rudis Sauer ( AMATA), Chenopodium album L. (CHEAL), Polygonum convolvulus L. (POLCO), Sinapis arvensis L. (SINAR) and/or at least one of the Conyza species, including without limitation Conyza sumatrensis (ERISU), Conyza canadensis (ERICA), Conyza bonariensis (ERIBO) or other related species (Conyza spp,

ERISS).

In certain embodiments of the compositions and methods described herein, a compound of formula (I) or a salt or ester thereof is used in combination with glufosinate or agriculturally acceptable salts, esters and amides thereof, and fluroxypyr or agriculturally acceptable salts thereof. from the point of view of agriculture with salts, esters and amides. In some embodiments, the weight ratio of a compound of formula (I) or a salt or ester thereof, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides range from about 1:400:70 to about 1:1:1. In certain embodiments, the weight ratio of a compound of formula (I) or a salt or ester thereof, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides range from about 1:400:70 to about 1:12.5:2.2. In certain embodiments, the weight ratio of a compound of formula (I) or a salt or ester thereof, and glufosinate or its agriculturally acceptable salts, esters and amides, and fluroxypyr or its agriculturally acceptable salts, esters and amides range from about 1:200:35 to about 1:25:8.8. In one embodiment, the composition contains a compound of formula (I) or a salt or ester thereof, and glufosinate ammonium, and fluroxypyrmeptyl, wherein the weight ratio of the compound of formula (I) or a salt or ester thereof, and glufosinate ammonium, and fluroxypyrmeptyl is from about 1:400:70 to about 1:1 or from about 1:400:70 to about 1:12.5:2.2. In one embodiment, the composition contains a compound of formula (I) or a salt or ester thereof, glufosinate ammonium and fluroxypyr meptyl, wherein the weight ratio is benzyl ester of the compound of formula (I) or a salt or ester thereof, and glufosinate ammonium, and fluroxypyr-meptyl is from about 1:200:35 to about 1:12.5:8.8 or from about 1:200:35 to about 1:25:4.4.

With respect to methods, in certain embodiments, the methods include bringing the composition described herein into contact with or applying to undesirable vegetation or vegetation to soil or water to prevent the emergence or growth of vegetation. In some embodiments, the composition is applied at an application rate of from about 1 gram of acid equivalent per hectare (g eq/ha) to about 400 g eq. k./ha in terms of the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 4 grams acid equivalent per hectare (g eq/ha) to about 400 g eq. k./ha in terms of the total amount of active ingredients in the composition. In some embodiments, the methods include contacting the unwanted vegetation or site thereof with a compound of formula (I) or a salt or ester thereof, glufosinate or agriculturally acceptable salts, esters and amides thereof, and fluroxypyr, or acceptable with from an agricultural point of view, salts, esters and amides, or a salt or ester thereof, or applying them to soil or water to prevent the emergence or growth of vegetation, for example, sequentially or simultaneously. In some embodiments, glufosinate or its agriculturally acceptable salts, esters and amides are used at a rate of about 50 g a. i./ha up to approximately 400 g a. i./ha, fluroxypyr or its agriculturally acceptable salts, esters and amides are used at a rate of approximately 8.8 g eq. k./ha up to approximately 70 g eq. k./ha, and the compound of formula (I) or its salt or ester is used at a rate of approximately 1 g eq. k./ha up to approximately 4 g eq. k./ha. In some embodiments, glufosinate or its agriculturally acceptable salts, esters and amides are used at rates of about 100 g eq. k./ha up to approximately 400 g eq. k./ha, fluroxypyr or its agriculturally acceptable salts, esters and amides are used at a rate of approximately 17.5 g eq. k./ha up to approximately 70 g eq. k./ha, and the compound of formula (I) or its salt or ester is used at a rate of approximately 1 g eq. k./ha up to approximately 4 g eq. k./ha. In some embodiments, glufosinate or its agriculturally acceptable salts, esters and amides are used at rates of about 200 g eq. k./ha up to approximately 400 g eq. k./ha, fluroxypyr or its agriculturally acceptable salts, esters and amides are used at a rate of approximately 35 g eq. k./ha up to approximately 70 g eq. k./ha, and the compound of formula (I) or its salt or ester is used at a rate of approximately 1 g eq. k./ha up to approximately 4 g eq. k./ha. In one embodiment, the methods use a compound of formula (I), glufosinate-ammonium and fluroxypyr-meptyl, wherein the compound of formula (I) is used at a rate of about 1 g eq. k./ha up to approximately 4 g eq. k./ha, ammonium glufosinate is used at a rate of approximately 50 g eq. k./ha up to approximately 400 g a. i./ha, and fluroxypyrmeptyl is used at a rate of approximately 8.8 g eq. k./ha up to approximately 70 g a. i./ha. In certain embodiments, methods and compositions that use a compound of formula (I) or a salt or ester thereof in combination with glufosinate or agriculturally acceptable salts, esters and amides thereof and fluroxypyr or a salt or ester thereof are used for control of Abutilon theophrasti Medik (Theophrastus's rope, ABUTH), Amaranthus rudis Sauer (tubercle acorn, AMATA), Chenopodium album L. (pigweed, CHEAL), Polygonum convolvulus L. (convolvulus, POLCO), Sinapis arvensis L. (mustard field, SINAR) and/or at least one of the species of Conyza, including, but not limited to, Conyza sumatrensis (ERISU), Conyza canadensis (ERICA), Conyza bonariensis (ERIBO) or other related species ( Conyza spp, ERISS).

The components of the compositions described herein can be used individually or as a component of a multicomponent herbicide system.

The compositions described herein can be used in combination with one or more additional herbicides to control a wider range of unwanted vegetation. When used in combination with other herbicides, the composition may be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides, or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be used in combination with the compositions and methods described herein include, but are not limited to, 4-CPA; 4-CPB; 4-CPP; 3,4-DA; 3,4-DB; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametrine, amibusin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrol, ammonium sulfamate, anilofos, anisuron, and sulam, atraton, atrazine, azaphenidine, azimsulfuron, aziprotrine, barban, BCPC, beflubutamide, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benthiocarb, bentazone sodium, benzadox, benzfendizone, benzipram, benzobicyclone, benzophenap, benzof luor, benzoylprop, benzthiazuron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispiribac sodium, borax, bromacil, bromobonil, bromobutide, bromophenoxime, bromoxynil, brompyrazone, butachlor, butafenacil, butamiphos, butenachlor, butidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrol , calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxifene, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazone, chlorimuron, chlornitrophen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamide, cinidone-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafoppropargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, k lopiralide, cloransulam- methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanathrine, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromide, daimuron, dalapon, dazomet, delachlor , desmedipham, desmetrin, diallate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, dietamquat, dietyl, diphenopentene, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, di metamethrin, dimethenamid , dimethenamid-P, dimexano, dimidazone, dinitramine, dinophenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamide, dipropetrin, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinasine, endothal, epronaz, EPTC, erbon , esprocarb, ethalfluralin, ethbenzamide, etamethsulfuron, etidimuron, etiolate, ethobenzamide, etobenzamide, etofumesate, ethoxyphene, ethoxysulfuron, etinophen, etnipromide, ethobenzanide, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+ isoxadifene -ethyl, fenoxasulfone, fenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flusetosulfuron, fluchloralin, flufenacet, flufenican, flufen pyr-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazin, flumipropin, fluometuron, fluorodifen, fluoroglycophene, fluoromidine, fluoronitrophen, fluotiuron, flupoxam, flupropacil, flupropanate, flupirsulfuron, fluridone, flurochloridone, fluroxypyr, fluroxypyr-m eptil, flurtamone, flutiacet, fomesafen, foramsulfuron, fosamine, flumiclorac, furyloxifene, glyphosate salts and esters, halosaphen, halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxidine, haloxyfop-methyl, haloxyfop-P-methyl, hexachloroacetone, hexaflurate, hexazinone, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprimidam, isocarbamide, isocyl, isomethiosine, isonoruron, isopoline, isopropalin, isoproturon, isouron, isoxaben, isoxachlortol, isoxaflutole, isoxapirifop, carbuti lat, ketospiradox, lactofen, Lenacil, Linuron, MAA, MAMA, complex broadcasts and amines of MCPA, MCPA-type, MCPB, Mekopropy, Mekoprop-P, Medinothel, Mephenacet, Metluidide, Mesoprazin, Mesusfuron, Mesotrion, Metamifop, Metamifer, Metazemlore, Metasusfuron, Metasusfuron, Metflurazon , metabenzthiazuron, metalpropalin, metazol, methiobencarb, methio

- 18 045326 zoline, methiuron, metometon, metoprothrin, methyl bromide, methyl isothiocyanate, methyl dimron, metobenzuron, metobromuron, metolachlor, methosulam, methoxuron, metribuzin, metsulfuron, metsulfuronmethyl, molinate, monalide, monisouron, monochlor acetic acid, monolinuron, monuron, morphamquat, MSMA, naproanilide, napropamide, napthalam, neburon, nicosulfuron, nipiraclofen, nitralin, nitrophen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazone, oxapyrazone, oxasulfuron, oxaziclomefone, oxyf luorfen, paraflufen-ethyl, parafluron, pebulate, pelargonic acid, pendimethalin, penoxulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, petoxamide, phenizofam, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercuracetate, pichloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazole, profluralin, profoxydim, proglinazine, prohexadione-calcium, promethone, prometrin, pronamide, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, pro sulfocarb, Susfuron, Prochsan, Prinlor, Pidanon, Pyxlonel, Pirathlufen-Etil, Pyraisufotol, Pirazogil, Pirazoline, Pirazusfuron-Etil, Pirazoxifen, Pyribenzoxim, Piributicarb, Pirichlor, Pyridaphol, Piritalid, Piriminobak-Meatyn. , pyridiobak-sodium, pyroxasassiphin, piroxulam, quinclorac, quinmerac, quinoclamine, quinonamide, quizalofop, quizalofop-P-ethyl, rodetanil, rimsulfuron, S-metolachlor, sebutylazine, sebumetone, sethoxydim, siduron, simazine, simeton, symetrine, SMA, sodium arsenite, sodium azide, sodium chlorate , sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapine, swep, SYN-523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumetone, terbutyl zine, terbutryn, tetrafluron, tenylchlor, thiazafluron, thiazopyr, tidiazimine, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiaphenacyl, thiocarbazyl, thioclorim, topramesone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tri benuron-methyl, tricamba, choline salt trichloropyr, trichloropyr esters and amines, tridifan, triethazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, triphopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, xylachlor and salts, esters, optically active isomers and mixtures thereof.

In some embodiments, the compositions described herein can be used in combination with one or more additional herbicides to control a broader range of unwanted vegetation. When used in combination with other herbicides, the composition may be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides, or applied sequentially with the other herbicide or herbicides. Some herbicides that may be used in combination with the compositions and methods described herein include, but are not limited to, acifluorfen, acifluorfen sodium, azaphenidine, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxifene, cynidone-ethyl, fluazolate , flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycophene, fluoroglycophene-ethyl, flutiacet, flutiacet-methyl, fomesafen, halosaphene, ipfencarbazone, lactofen, oxadiargyl, oxadiazone, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen -ethyl, saflufenacil, sulfentrazone, thidiazimine, thiaphenacyl, trifludimoxazine, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4 -tetrahydropyrimidin-3yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4trifluoromethylphenoxy)-5-methyl-1H-pyrazol- 1-Carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl 3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 915396-43-9), N -ethyl3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), Ntetrahydrofurfuryl-3-(2-chloro-6-fluoro- 4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 45100-03-7) and 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4- dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione; b5) from the group of bleaching herbicides.

The compositions and methods described herein may additionally be used in combination with glyphosate, 5-enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitors, glutamine synthetase inhibitors, dicamba, phenoxyauxins, pyridyloxyauxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones , phenylpyrazolines, acetyl-CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4hydroxyphenylpyruvate dioxygenase inhibitors (HPPD), phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule assembly inhibitors, very long chain fatty acid biosynthesis inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines and bromoxynil in relation to crops, tolerant to glyphosate, EPSP synthase inhibitor, glufosinate, glutamine synthetase inhibitor, dicamba, phenoxyauxin, pyridyloxyauxin, auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, ACCase,

- 19 045326 imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazolinone, ALS or AHAS, HPPD, phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, PPO, cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule assembly inhibitor, biosynthesis inhibitor for very long chain fatty acids, biosynthesis inhibitor fatty acids and lipids, photosystem I inhibitor, photosystem II inhibitor, triazine and bromoxynil, and for crops having multiple or stacked traits that confer tolerance to multiple chemicals and/or multiple mechanisms of action through single and/or several resistance mechanisms. In some embodiments, a compound of formula (I), or a salt or ester thereof, and a complementary herbicide, or a salt or ester thereof, is used in combination with herbicides that are selective for the crop being treated and that complement the spectrum of weeds controlled by the compounds when used. norm of use. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation, as a tank mix, or sequentially.

In some embodiments, the compositions described herein are used in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (Mexil), ciometrinil, cyprosulfamide, daimuron, dichlormide, dicyclonone, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaosi, mefenpyr-diethyl, mephenate, naphthalene anhydride (NA), oxabetrinil, R29148 and N-phenylsulfonylbenzoic amides acids to increase their selectivity. In some embodiments, the antidotes are applied to rice, cereal, corn, or maize crops. In some embodiments, the antidote is cloquintocet acid or an ester or salt thereof. In certain embodiments, cloquintoset is used to counteract the harmful effects that the compositions have on rice and grain crops. In some embodiments, the antidote is cloquintocet-mexil.

In some embodiments, the compositions described herein are used in combination with one or more plant growth regulators, such as 2,3,5-triiodobenzoic acid, IAA, IBA, naphthalene acetamide, α-naphthalene acetic acids, benzyladenine, 4-hydroxyphenethyl alcohol, kinetin , zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tribufos, aviglycine, ethephon, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, 2,3,5- tri-iodobenzoic acid, morphactins, dichloroflurenol, flurprimidol, mefluidide, paclobutrazol, tetsiklasis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, metasulfocarb, prohexadione, triapentenol and trinexapac.

In some embodiments, plant growth regulators are used on one or more crops or crops, such as rice, cereals, corn, maize, broadleaf crops, oilseed rape/canola, turfgrass, pineapple, sugarcane, sunflower, pasture, meadows, pastures, fallow land, tree and vineyards, plantation crops, vegetable crops and non-agricultural (ornamental) plantings. In some embodiments, a plant growth regulator is mixed with a compound of formula (I) or mixed with a compound of formula (I) and an imidazolinone to have a preferentially beneficial effect on plants.

In some embodiments, the compositions provided herein further comprise at least one agriculturally acceptable excipient or carrier. Suitable excipients or carriers should not be phytotoxic to valuable crops, in particular at the concentrations used when applying compositions for selective weed control in the presence of crops, and they should not react chemically with herbicidal components or other ingredients in composition composition. Such mixtures may be formulated for use directly on weeds or their habitats, or they may be concentrates or formulations that are typically diluted with additional carriers and excipients before use. They may be in the form of solids, such as, for example, dusts, granules, water-dispersible granules or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided in the form of a premix or tank mixture.

Agriculturally suitable excipients and carriers include, but are not limited to, crop aid oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; a mixture of petroleum hydrocarbon, alkyl esters, organic acid and anionic surfactant; C ₉ -C ₁₁ -alkylpolyglycoside; phosphoric acid alcohol ethoxylate; natural ethoxylate

- 20 045326 primary alcohol (C ₁₂ -C ₁₆ ); di-sec-butylphenol block copolymer EO-PO; methyl-terminated polysiloxane; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol ethoxylate (synthetic) (8 EO); Tall amine ethoxylate (15 EO) and PEG(400) dioleate-99.

Useful liquid carriers include water and organic solvents. Organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, canola oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc. .; esters of the above vegetable oils; esters of monoalcohols or dibasic, tribasic or other lower polyalcohols (containing 4-6 hydroxy), such as 2-ethylhexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, dioctyl succinate, dibutyl adipate, dioctyl phthalate and the like; esters of mono-, di- and polycarboxylic acids, etc. Specific organic solvents include, but are not limited to, toluene, xylene, ligroin, oil adjuvant, acetone, methyl ethyl ketone, cyclohexanone, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amine fishing alcohol, ethylene glycol, propylene glycol, glycerin, N-methyl-2-pyrrolidinone, N, N-dimethylalkylamides, dimethyl sulfoxide, liquid fertilizers, etc. In certain embodiments, water is the vehicle for diluting the concentrates.

Suitable solid carriers include, but are not limited to, talc, pyrophyllite clay, silica, attapulgite clay, kaolin clay, diatomaceous earth, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, nut shell flour, lignin, cellulose, etc.

In some embodiments, the compositions described herein further contain one or more surfactants. In some embodiments, such surfactants are used in both solid and liquid compositions, and in certain embodiments, those intended to be diluted with a carrier prior to use. Surfactants may be anionic, cationic or nonionic in nature and may be used as emulsifiers, wetting agents, suspending agents or other purposes. Surfactants that can also be used in the compositions of the present invention are described, among others, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey, 1998 and in Encyclopedia of Surfactants, Vol. I-III, Chemical Publishing Co., New York, 1980-81. Surfactants include, but are not limited to, alkyl sulfate salts such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts such as calcium dodecylbenzenesulfonate; addition products of alkylene oxides and alkylphenols, such as nonylphenol-O8 ethoxylate; addition products of alkylene oxides and alcohols, such as tridecyl alcohol-C16 ethoxylate; soaps such as sodium stearate; alkyl naphthalene sulfonate salts such as sodium dibutyl naphthalene sulfonate; dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitan oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol fatty acid esters such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkylphosphate esters; vegetable or seed oils such as soybean oil, canola/canola oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, flaxseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc.; and esters of the above vegetable oils, and in certain embodiments, methyl esters.

In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural excipient, as a liquid carrier, or as a surfactant.

Other exemplary additives for use in the compositions provided herein include, but are not limited to, compatibilizers, antifoams, binding agents, neutralizing agents and buffers, corrosion inhibitors, colorants, fragrances, distribution aids, penetration aids, adhesion aids. , dispersants, thickeners, freezing point depressants, antimicrobial agents, etc. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides and the like. and can be formulated with carriers based on liquid fertilizers or solid particulate fertilizers such as ammonium nitrate, urea and the like.

In some embodiments, the concentration of active ingredients in the compositions described herein ranges from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight. In compositions formulated for use as concentrates, the active ingredients are present in a concentration of from about 0.1 to 98 percent by weight, and in certain embodiments, from about 0.5 to 90 percent by weight. In certain embodiments, such embodiment compositions are diluted with an inert carrier, such as water, before use. The diluted compositions, which are typically applied to weeds or weed habitats, in certain embodiments contain the active ingredient in an amount of from about 0.0006 to 3.0 percent by weight and in certain embodiments in an amount from about 0.01 to 1 .0 percent by weight.

The compositions of the present invention can be applied to weeds or their habitats through the use of conventional ground or aerial sprayers, sprayers and granule spreaders, by addition to irrigation water or by other conventional means known to those skilled in the art.

The described embodiments and the following examples are for illustrative purposes only and are not intended to limit the scope of the claims. Other modifications, uses or combinations with respect to the compositions described herein will be apparent to one of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.

Examples

The results in the Examples section are from greenhouse tests.

Seeds or nuts of the desired test plant species were planted in a soil base prepared by mixing loam or sandy loam soil (for example, 28.6 percent loam, 18.8 percent clay, and 52.6 percent sand with a pH of approximately 5.8 and organic matter, approximately 1.8 percent) and calcareous sand bed in a ratio of 80 to 20. The soil base was placed in 1 quart plastic pots with a surface area of 83.6 cm ² . Fungicide and/or other chemical or physical treatments were applied when necessary to ensure good germination and healthy plants. Plants were grown for 8-22 days in a greenhouse with an approximately 14-hour photoperiod in which the temperature was maintained at approximately 29°C during the day and at 26°C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were used as a drench solution as needed and water was added regularly. If necessary, additional lighting was provided using ceiling-mounted 1000-watt metal halide lamps. Plants were used for testing when they reached the first to fourth true leaf stage.

The treatments contained acid or halauxifen methyl esters (methyl 4amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate), each formulated as an SC (suspension concentrate), and various herbicidal components individually and in combination. The form of the compound of formula I was used on an acid equivalent basis.

The test compound form of formula I included:

ci'l;

halauxifene-methyl

Treatment parameters were calculated based on the rates tested, the concentration of active ingredient or acid equivalent in the formulation for a volume of 12 ml, based on an application rate of 187 l/ha.

For treatments containing formulated compounds, measured amounts of the compounds can be added individually to 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® Crop Oil Concentrate to produce 12X the original solutions. If the test compound dissolved slowly, the mixture was heated and/or sonicated. Application solutions were prepared by adding the appropriate amount of each stock solution (e.g., 1 mL) and diluting to the appropriate final concentrations by adding 10 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.

For treatments containing technical compounds, weighed quantities can be added individually to 25 ml glass vials and diluted at a ratio of 97:3 v/v. acetone/DMSO mixtures to obtain 12X stock solutions. If the test compound is slowly dissolving

- 22 045326 elk, the mixture was heated and/or subjected to ultrasound. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluting to appropriate final concentrations by adding 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that The final spray solutions contained 1.25% (v/v) crop oil concentrate. When using technical materials, concentrated stock solutions can be added to spray solutions in such quantities that the final concentrations of acetone and DMSO in application solutions are 16.2% and 0.5%, respectively.

For treatments consisting of formulated and technical compounds, weighed quantities of technical materials were added individually into 25 ml glass vials and dissolved in a volume of 97:3 v/v. acetone/DMSO mixture to obtain a 12X stock solution, and measured amounts of the formulated compounds were added individually to 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain a 12X stock solution . If the test compound dissolved slowly, the mixture was heated and/or sonicated. Application solutions were prepared by adding the appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations by adding the appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final solutions for spraying contained 1.25% (v/v) crop oil concentrate. If necessary, additional water and/or 97:3 v/v were added to individual application solutions. acetone/DMSO mixtures, resulting in final concentrations of acetone and DMSO in the comparison application solutions of 8.1% and 0.25%, respectively.

Before use, all stock and application solutions were visually assessed for compound compatibility. Spray solutions were applied to the plant material using a Mandel down-jet sprayer equipped with an 8002E nozzle calibrated to deliver 187 L/ha to an application area of 0.503 m ² at a spray height of 18-20 inches (46-20 inches). 50 cm) above the average plant canopy. Control plants were sprayed in the same way using solvent blank.

Treated plants and control plants were placed in a greenhouse as described above and watered by subsurface irrigation to prevent leaching of test compounds. After approximately 7, 14 and 21 days, the condition of the test plants was visually determined in comparison to untreated plants and scored on a scale of 0 to 100 percent, with 0 indicating no damage or growth inhibition and 100 indicating complete killing.

The tested compounds, application rates used, test plant species and results are given in Table. 1-4.

Table 1 Weed control results for various broadleaf weeds using tank mixtures of halauxifen-methyl (chemical 1) + glufosinate-ammonium (chemical 2) + fluroxypyr-meptyl (chemical 3) at 7 DAA (day after application) , trial; WMGJH15738, apcd: A

Rad No. Weed code according to Bayer Inter in. est. processing Chem. substance 1 Application rate, g eq. sq./ha Chem. thing 1 Avg. % weed control Chem. thing 2 Application standard g a. i./ha Chem. thing 2 Wednesday. % weed control Chem. thing 3 Standard of application g eq. sq./ha Chem. thing 3 Avg. % weed control Observ. Wednesday. % weed control Predicted average, % weed control Number of Observed P>t 1 Ci i HAL 7 DAA 1 2 56.25 100 5 17.5 0 92.75 57.75 4 0.012 1 CHEAL 7 DAA 1 4 56.25 100 5 17.5 0 97.75 57.94 4 0.025 I CHEAL 7 DAA 1 4 56.25 200 31.25 17.5 0 96.5 71.31 4 0.008 I CHEAL 7 DAA 1 2 56.25 50 0 17.5 0 80 56.25 4 0.068 1 CHE AL 7 DAA 1 4 56.25 50 0 17.5 0 83 56.25 4 0.042 1 CHEAL 7 DAA 1 1 28.75 100 5 17.5 0 73 33.25 4 0.007 1 CHEAL 7 DAA 1 1 28.75 200 31.25 17.5 0 97.5 49.31 4 0.028 1 CHEAL 7 DAA 1 2 56.25 200 31.25 17.5 0 93.5 69.56 4 0.021 1 CHEAL 7 DAA 1 1 28.75 50 0 17.5 0 78.25 28.75 4 0.004 1 CHEAL 7 DAA 1 1 28.75 400 92.75 17.5 0 98.75 95.03 4 0.067 1 CHEAL 7 DAA 1 1 28.75 200 31.25 35 0 89.75 49.31 4 0.02 1 CHEAL 7 DAA 1 4 56.25 100 5 35 0 89.25 57.94 4 0.025 1 CHEAL 7 DAA 1 2 56.25 100 5 35 0 93 57.75 4 0.012 1 CHEAL 7 DAA 1 I 28.75 100 5 35 0 76.25 33.25 4 0.001 1 CHEAL 7 DAA 1 4 56.25 200 31.25 35 0 93.5 71.81 4 0.005 1 ...............................CHEAL...... ............... 7 DAA 1 2 56.25 200 31.25 35 ..... . 0 97 69.56 4 0.029 1 CHEAL 7 DAA 1 2 56.25 50 0 35 0 82.5 56.25 4 0.028 1 CHEAL 7 DAA 1 1 28.75 50 0 35 0 75 28.75 4 0.004 1 CHEAL 7DAA1 4 56.25 50 0 35 0 85.5 56.25 4 0.029 1 CHEAL 7DAA 1. 4 56.25 100 5 70 10 92 60.62 4 0.033 1 <H1 AL 7 DAA 1 1 28.75 200 31.25 70 10 80.5 56.67 4 0.022 1 CHEAL 7 DAA 1 4 56.25 200 31.25 70 10 97 74.06 4 0.019 1 CHEAL 7 DAA 1 4 56.25 50 0 70 10 87.25 59.25 4 0.048 1 CHEAL 7DAA1, 1 28.75 100 5 70 10 78 41.15 4 0 1 CHEAL 7 DAA 1 1 28.75 50 0 70 10 78.75 37.81 1 0 1 CHEAL 7 DAA 1 1 28.75 200 31.25 8.8 0 92.5 49.31 4 0.033 1 CHEAL 7 DAA 1 1 28.75 100 5 8.8 0 85.5 33.25 4 0 1 CHEAL 7 DAA 1 4 56.25 200 31.25 8.8 0 96.25 71.81 4 0.008 1 CHEAL 7 DAA 1 4 56.25 100 5 8.8 0 98.75 57.94 4 0.024 1 CHEAL 7 DAA 1 2 56.25 200 31.25 8.8 0 95.75 69.56 4 0.012

- 23 045326

1 CHEAL 7 DAA 1 2 56.25 100 5 8.8 0 90 57.75 4 0.018 1 CHE AL 7 DAA 1 1 28.75 50 0 8.8 0 77.5 28.75 4 0.003 1 CHEAL 7 DAA 1 2 56.25 50 0 8.8 0 78.75 56.25 4 0.044 1 CHEAL 7DAA1 4 56.25 50 () 8.8 0 92.75 56.25 4 0.011 4 POLCO 7 DAA 1 2 11.25 100 31.25 17.5 47.5 93.25 70.1 4 0.01 1 POLCO 7 DAA 1 4 28.75 50 2.5 17.5 47.5 89.75 63.81 4 0.054 4 POLCO 7 DAA I 1 2.5 100 31.25 17.5 47.5 85 68.35 4 0.053 4 POLCO 7DAA1 1 2.5 50 2.5 17.5 47.5 81.25 50.75 4 0.06'1 4 POLCO 7 DAA 1 1 2.5 100 31.25 8.8 52.5 87.5 67.94 4 0.073 4 POLCO 7 DAA 1 1 2.5 50 2.5 8.8 52.5 73.75 55 4 0.001 4 POLCO 7DAA1 2 11.25 50 2.5 8.8 52.5 84.25 58.5 4 0.017 5 AMATA 7 DAA 1 -I 73 50 15 17.5 3.75 93.25 78.16 1 0.001 5 AMATA 7DAA1 1 73 50 15 35 3.75 84.25 78.24 4 0.063 5 AMATA 7DAA1 E 70.5 100 63 8.8 0 97 89.04 4 0.019 AMATA 7DAA1 4 73 50 15 8.8 0 87.5 77.38 4 0.07 6 ABUTH 7 DAA 1 2 81.25 100 12.5 17.5 28.75 98.5 88.39 4 0 6 ABUTH 7 DAA I 4 84.5 100 12.5 17.5 28.75 98.75 90.73 4 0.061 6 ABUTH 7 DAA 1 2 81.25 50 1.25 17.5 28.75 98.5 86.92 4 0 6 ABUTH 7 DAA 1 4 84.5 50 1.25 17.5 28.75 97.75 89.53 4 0.038 6 ABUTH 7DAAI 2 81.25 100 12.5 35 67.5 98.25 94.71 4 0.001 6 ABUTH 7 DAA 1 1 81.25 50 1.25 35 67.5 97.5 93.93 4 0.021 b ABUTH 7 DAA 1 4 84.5 50 1.25 35 67.5 98.75 94.92 4 0.092 6 ABUTH 7DAA1 2 81.25 50 1.25 70 75.5 97.75 95.55 4 0.069 ft ABUTH 7 DAA 1 4 84.5 100 12.5 8.8 15 98.25 88.75 4 0.04 6 ABUTH 7 DAA 1 2 81.25 100 12.5 8.8 15 97 86.11 4 0.001 6 ABUTH 7 DAA 1 2 81.25 50 1.25 8.8 15 94.5 84.3 4 0.029 6 ABUTH 7 DAA 1 4 84.5 50 1.25 8.8 15 99 87.22 4 0.054

table 2

Weed control results for various broadleaf weeds using tank mixtures of halauxifen-methyl (chemical 1) + glufosinate-ammonium (chemical 2) + fluroxypyr-meptyl (chemical 3) at 14 DAA (day after application), test tanning: WMGJH15738. apcd: A

Rad No. Weed code according to Bayer Inter in. est. processing Chem. thing 1 Let us accept the norm, g ei. sq./ha Chem. thing 1 Wednesday. % weed control Chem. thing 2 Norm Prien. g a. i./ha Chem. thing 2 Wednesday. % weed control Chem. thing 3 Norm gfimen. g eq. sq./ha Chem. thing 3 Wednesday. % weed control Observ. Wednesday. % weed control Predicted Wednesday. % weed control Number of Observed RH 7 CHEAL 14 DAA 1 2 60 100 5 17.5 10 96 65.98 4 0.001 7 CHEAL 14 DAA 1 4 62.5 100 5 17.5 10 100 67.57 4 0.012 7 CHEAL 14 DAA 1 1 33.33 200 8.33 17.5 5 95 40.83 3 0.026 7 CHEAL 14 DAA 1 2 60 200 8.33 17.5 5 91.67 65.58 3 0.007 7 CHEAL 14 DAA 1 4 62.5 50 7.5 17.5 10 91.25 68.21 4 0.03 7 CHEAL 14 DAA 1 1 40 100 5 17.5 10 84.75 48.28 4 0.018 7 CHEAL 14 DAA 1 2 60 50 7.5 17.5 10 80 66.93 4 0.012 7 CHEAL 14 DAA 1 1 40 50 7.5 17.5 10 76.25 49.34 4 0.085 7 CHEAL 14 DAA 1 4 63.33 200 8.33 17.5 5 97 69 3 0.003 7 CHEAL 14 DAA 1 1 40 400 65 17.5 10 96.25 79.25 4 0.044 7 CHEAL 14 DAA 1 2 60 40) 65 17.5 10 95.5 86.99 4 0.068 7 CHEAL 14 DAA 1 4 63.33 200 8.33 35 5 95 69 3 0.013 7 CHEAL 14 DAA 1 1 40 50 7.5 35 3.75 70 48.12 4 0.026 7 CHEAL 14 DAA 1 4 62.5 100 5 35 3.75 100 64.96 4 0.011 7 CHEAL 14 DAA 1 2 60 100 5 35 3.75 91.25 62.99 4 0.005 7 CHEAL 14 DAA 1 60 200 8.33 35 5 99 65.08 3 0.02 7 CHEAL 14 DAA 1 1 40 100 5 35 3.75 82.25 46.87 4 0.006 7 CHEAL 14 DAA 1 2 60 50 7.5 35 3.75 80.75 64.12 4 0.009 7 CHEAL 14 DAA 1 2 60 400 65 35 3.75 96.5 86.4 4 0.059 7 CHEAL 14 DAA 1 4 62.5 50 7.5 35 3.75 85 65.71 4 0.059 7 CHEAL 14 DAA 1 1 33.33 200 8.33 35 5 96.67 42.83 3 0.006 7 CHEAL 14 DAA 1 4 62.5 50 7.5 70 31.25 93.5 75.28 4 0.027 7 CHEAL 14 DAA 1 4 63.33 200 8.33 70 35 100 78.75 3 0.014 7 CHEAL 14 DAA 1 4 62.5 40) 65 70 31.25 99.5 90.92 4 0.055 7 CHEAL 14 DAA 1 1 40 50 7.5 70 31.25 81 62.69 4 0.082 7 CHEAL 14 DAA 1 4 62.5 100 5 70 31.25 96.25 74.83 4 0.013 7 CHEAL 14 DAA 1 1 33.33 200 8.33 70 35 96.67 60 3 0.02 7 CHEAL 14 DAA 1 1 40 100 5 70 31.25 75 61.94 4 0.059 7 CHEAL 14 DAA 1 2 60 200 8.33 70 35 94.67 76.42 3 0.024 7 CHEAL 14 DAA 1 1 40 100 5 8.8 0 86.75 44 4 0.004 7 CHEAL 14 DAA 1 1 33.33 200 8.33 8.8 0 81.67 38.33 3 0.049 7 CHEAL 14 DAA 1 2 60 100 5 8.8 0 95.5 61.88 4 0 7 CHEAL 14 DAA 1 4 62.5 100 5 8.8 0 99.75 64 4 0.008 7 CHEAL 14 DAA 1 4 63.33 200 8.33 8.8 0 98 67.5 3 0 7 CHEAL 14 DAA 1 1 40 50 7.5 8.8 0 72.5 45.25 4 0.022 7 CHEAL 14 DAA 1 2 60 200 8.33 8.8 0 99 63.33 3 0.001 7 CHEAL 14 DAA 1 2 60 50 7.5 8.8 0 88.5 63 4 0.002 7 CHEAL 14 DAA 1 4 62.5 400 65 8.8 0 99.5 86.62 4 0.05 7 CHEAL 14 DAA 1 2 60 400 65 8.8 0 96.25 85.94 4 0.04 7 CHEAL 14 DAA 1 4 62.5 50 7.5 8.8 0 99.75 64.75 4 0.01 10 SINAR 14 DAA 1 4 0 200 52.5 35 6.3.75 94.25 83 4 0.087 eleven ABUTH 14 DAA 1 2 87.25 100 8.75 17.5 20 100 90.88 4 0.049 eleven ABUTH 14 DAA 1 2 87.25 50 5 17.5 20 100 91.1 4 0.048 eleven ABUTH 14 DAA 1 2 87.25 200 22.5 17.5 20 99.25 92.58 4 0.056 II ABUTH 14 DAA 1 2 87.25 100 8.75 35 67 100 95.95 4 0.055 eleven ABUTH 14 DAA 1 2 87.25 200 22.5 35 67 99 96.72 4 0.088 eleven ABUTH 14 DAA 1 2 87.25 50 5 35 67 100 96.04 4 0.056 eleven ABUTH 14 DAA 1 2 87.25 200 22.5 70 70 99.5 97.02 4 0.046 eleven ABUTH 14DAA 1 2 87.25 50 5 70 70 100 96.42 4 0.054 eleven ABUTH 14 DAA 1 2 87.25 100 8.75 70 70 100 96.33 4 0.054 eleven ABUTH 14 DAA 1 2 87.25 200 22.5 8.8 2.5 98 90.36 4 0.058 eleven ABUTH 14 DAA 1 2 87.25 100 8.75 8.8 2.5 99.75 88.11 4 0.059 eleven ABUTH 14 DAA 1 2 87.25 50 5 8.8 2.5 99.5 88.38 4 0.062 12 POLCO 14 DAA 1 uh 0 100 0 17.5 62.25 92 62.25 4 0.092 12 POLCO 14 DAA 1 2 0 100 0 8.8 12.5 76.25 12.5 4 0.016 12 POLCO 14 DAA 1 2 0 50 0 8.8 12.5 100 12.5 4 0.006 12 POLCO 14 DAA 1 4 20 50 0 8.8 12.5 91.25 26.25 4 0.017

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Claims (9)

Table 3 Weed control results for various broadleaf weeds using tank mixtures of halauxifen-methyl (chemical 1) + glufosinate-ammonium (chemical 2) + fluroxypyr-meptyl (chemical 3) at 17 DAA (day after application), test - title: WMGJH15738, apcd: A Row No. Weed code according to Bayer Inter in. est. processing Chem. thing 1 Gfimen norm. g eq. sq./ha Chem. thing 1 Avg. % weed control Chem. thing 2 Application standard ha.i./ha Chem. thing 2 Avg. % weed control Chem. thing 3 Application standard g eq. sq./ha Chem. thing 3 Avg. % weed control On dishes, avg. % weed control Propuzir. avg. % weed control Number of Observed P>1 13 CHEAL 17 DAA 1 2 53.75 100 6.25 17.5 8.75 95 60.25 4 0.004 13 CHEAL 17 DAA 1 4 62.5 100 6.25 17.5 8.75 100 67.88 4 0.004 13 CHEAL 17 DAA 1 4 62.5 200 20 17.5 8.75 97.5 72.85 4 0 13 CHEAL 17 DAA 1 2 53.75 50 12.5 17.5 8.75 78.25 63.62 4 0.025 13 CHEAL 17 DAA 1 4 62.5 50 12.5 17.5 8.75 90 70.12 4 0.027 13 CHEAL 17 DAA I 1 40 100 6.25 17.5 8.75 75 49.25 4 0.041 13 CHEAL 17 DAA 1 2 53.75 400 52.5 17.5 8.75 92 79.12 4 0.081 13 CHEAL 17 DAA 1 1 40 200 20 17.5 8.75 90 55.33 4 0.014 13 CHEAL 17 DAA 1 2 53.75 200 20 17.5 8.75 89.5 65.96 4 0.023 13 CHEAL 17 DAA 1 1 40 50 12.5 17.5 8.75 66.75 53.19 4 0.038 13 CHEAL 17 DAA 1 4 62.5 400 52.5 17.5 8.75 94 83.25 4 0.081 13 CHEAL 17 DAA 1 1 40 200 20 35 3.75 89.5 53.73 4 0.005 13 CHEAL 17 DAA 1 4 62.5 100 6.25 35 3.75 100 65.88 4 0.004 13 CHEAL 17 DAA 1 2 53.75 400 52.5 35 3.75 94 78.75 4 0.071 13 CHEAL 17 DAA 1 2 53.75 100 6.25 35 3.75 89.5 58.5 4 0.006 13 CHEAL 17 DAA 1 1 40 100 6.25 35 3.75 78.5 47 4 0.006 13 CHEAL 17 DAA 1 4 62.5 200 20 35 3.75 98.75 71.4 4 0 13 CHEAL 17 DAA 1 2 53.75 .200 20 35 3.75 100 64.72 4 0.001 13 CHEAL 17 DAA 1 2 53.75 50 12.5 35 3.75 89.5 61.69 4 0.007 13 CHEAL 17 DAA 1 1 40 50 12.5 35 3.75 69.5 50.72 4 0.006 13 CHEAL 17 DAA 1 4 62.5 50 12.5 35 3.75 87.5___ 68 4 0.069 13 CHEAL 17 DAA 1 4 62.5 400 52.5 35 3.75 96.5 82.75 4 0.027 13 CHEAL 17 DAA 1 4 62.5 100 6.25 70 38.75 96.25 77.69 4 0.013 13 CHEAL 17 DAA 1 4 (P.5 400 52.5 70 38.75 98.75 88.65 4 0.021 13 CHEAL 17 DAA 1 4 62.5 50 12.5 70 38.75 92 79.19 4 0.086 13 CHEAL 17 DAA 1 4 62.5 400 52.5 8.8 0 100 82 4 0.018 13 CHEAL 17 DAA 1 1 40 200 20 8.8 0 74.5 51.5 4 0.015 13 CHEAL 17 DAA 1 1 40 100 6.25 8.8 0 87 44.38 4 0.003 13 CHEAL 17 DAA 1 4 62.5 200 20 8.8 0 96.25 70.12 4 0.001 13 CHEAL 17 DAA 1 4 62.5 100 6.25 8.8 0 100 64.38 4 0.004 13 CHEAL 17 DAA 1 2 53.75 200 20 8.8 0 99.5 62.81 4 0.004 13 CHEAL 17 DAA 1 2 53.75 100 6.25 8.8 0 94.5 56.25 4 0.004 13 CHEAL 17 DAA 1 1 40 50 12.5 8.8 0 70 48.75 4 0.012 13 CHEAL 17 DAA 1 2 53.75 50 12.5 8.8 0 83.25 60 4 0.013 13 CHEAL 17 DAA 1 4 62.5 50 12.5 8.8 0 100 66.88 4 0.004 Table 4 Weed control results for various broadleaf weeds using tank mixtures of halauxifen-methyl (chemical 1) + glufosinate-ammonium (chemical 2) + fluroxypyr-meptyl (chemical 3) at 21 DAA (day after application), test .............: WMGJH15738, apcd: A ..... .......................... ............. Row No. Weed code according to Bayer Intern, est. processing Chem. thing 1 Application standard g eq. kUga Htl. thing 1 Avg. % weed control Hnm. thing 2 Let us accept the norm, g a. and Yeah Chem. thing 2 Avg. % weed control Chem. thing 3 We accept the norm, g eq. kUga Chem. thing 3 Avg. % weed control Observ. avg. % weed control Tsrogyasvir. Wednesday. % weed control Number of Observed P>1 14 POLCO 21 DAA 1 1 0 100 6.25 ABOUT 0 82.5 6.25 4 0.006 14 POLCO 21 DAA 1 2 6.25 100 6.25 8.8 0 67.5 12.5 4 0.04 14 POLCO 21 DAA 1 2 6.25 50 0 8.8 0 100 6.25 4 0.001 14 POLCO 21 DAA 1 4 17.5 50 0 8.8 0 90 17.5 4 0.003 15 SINAR 21 DAA 1 1 1.25 200 53.75 17.5 54.25 100 77.14 4 0.098 Although the new technology has been illustrated and described in detail in the graphics and in the foregoing description, it should be considered as illustrative and not limiting in nature, it being understood that only preferred embodiments have been shown and described and that all changes and modifications that correspond to the essence of the new technology are subject to protection. In addition, although the new technology has been illustrated using case studies, theoretical arguments, reports, and illustrations, these illustrations and the accompanying discussion should in no way be interpreted as a limitation of the technology. All patents, patent applications and references to texts, scientific papers, publications, etc., referenced in the present invention are hereby incorporated by reference in their entirety to the extent they do not conflict with the express teachings of this specification. CLAIM 1. A herbicidal composition containing a herbicidal effective amount of (a) halauxifen-methyl; (b) a second herbicide comprising glufosinate ammonium; And - 25 045326 (c) a third herbicide comprising fluroxypyr-meptyl; where the weight ratio of (a), (b) and (c) is from 1:400:70 to 1:12:2. 2. The composition according to claim 1, further containing an agriculturally acceptable excipient or carrier. 3. The composition according to claim 1 or 2, further containing at least one herbicide antidote. 4. A method of controlling unwanted vegetation, comprising the steps of contacting a plant, where the plant is the unwanted vegetation, or a habitat thereof, soil or water, where the soil or water supports the growth of the unwanted vegetation, with a herbicidal effective amount of a composition containing (a) halauxifen -methyl; (b) a second herbicide comprising glufosinate ammonium; and (c) a third herbicide comprising fluroxypyr-meptyl; where the weight ratio of (a), (b) and (c) is from 1:400:70 to 1:12:2. 5. The method according to claim 4, where control of unwanted vegetation is carried out in rice with sowing seeds in the ground, with sowing seeds in water and seedling rice, cereals, wheat, barley, types of oats, rye, sorghum, corn/maize, sugar cane , sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, meadows, pastures, fallow land, lawn grass, tree and vineyards, aquatic environments, industrial vegetation control (IVM) or right-of-way (ROW). 6. The method according to claim 4 or 5, where (a), (b) and (c) are applied before emergence to a weed or crop. 7. The method according to any one of claims 4-6, where the control of unwanted vegetation is carried out in crops tolerant to glyphosate, 5enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitor, glufosinate, glutamine synthetase inhibitor, dicamba, phenoxyauxin, pyridyloxyauxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl-CoA carboxylase (ACCase) inhibitor, imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazolinone, acetolactate synthase (ALS) inhibitors or acetohydroxyacid intase (AHAS), an inhibitor of 4-hydroxyphenylpyruvate dioxygenase ( HPPD), phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule assembly inhibitor, very long chain fatty acid biosynthesis inhibitor, fatty acid and lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor , triazine or bromoxynil. 8. The method of claim 7, wherein the hardy crop has multiple or stacked traits conferring tolerance to multiple herbicides or multiple mechanisms of action. 9. The method according to any one of claims 4 to 8, wherein the unwanted vegetation comprises a weed with resistance or tolerance to the herbicide. Eurasian Patent Organization, EAPO Russia, 109012, Moscow, Maly Cherkassky lane, 2