WO2023172856A1

WO2023172856A1 - The use of aminopyralid herbicide compositions to control weeds in sugarcane

Info

Publication number: WO2023172856A1
Application number: PCT/US2023/063753
Authority: WO
Inventors: Felipe Ridolfo LUCIO; Gabriel Rohrer PEREIRA; Caio Vitagliano Santi ROSSI
Original assignee: Corteva Agriscience Llc
Priority date: 2022-03-09
Filing date: 2023-03-06
Publication date: 2023-09-14

Abstract

Methods of controlling weeds in sugarcane comprising applying a composition of aminopyralid plus diclosulam; or a composition of aminopyralid plus diclosulam plus tebuthiuron; or a composition of aminopyralid plus diclosulam plus clomazone; or a composition of aminopyralid plus sulfentrazone plus tebuthiuron are described.

Description

THE USE OF AMINOPYRALID HERBICIDE COMPOSITIONS TO CONTROL WEEDS IN SUGARCANE

CROSS-REFERENCE TO RELATED APPLICATIONS

This patent application claims the benefit of U.S. Provisional Application No. 63/269044 filed on March 9, 2022, which is incorporated herein by reference in its entirety.

Background

Sugarcane is an important crop because of its many uses including the production of molasses, brown sugar, sugar, ethanol, and alcoholic beverages. Sugarcane can be used for animal feed and sugar waste may be converted to fertilizer and fuel. Sugarcane is grown on approximately 10MM ha in Brazil, with the acreage likely to increase in the future. The 2020/2021 harvest in the South-Center region of Brazil was 603 million tons. A portion of the harvest was used to produce alcohol, with a total alcohol production of 29.7 billion liters. Other countries where large scale sugarcane production occurs include India, China, Mexico, Thailand, Pakistan, Colombia, Australia, Indonesia, and the United States.

Certain grass and broadleaf weeds are known to compete with sugarcane, lowering crop yields and causing problems for harvesting equipment. Currently, broadleaf and grass weeds such as Ipomoea spp., Merremia spp. , Miicuna spp. , Riccinus Communis, Brachiaria decumbens, and Panicum maximum, are problematic.

Pre-emergent herbicides can be used — and are sometimes preferred — to control weeds in sugarcane, and mixtures of active ingredients are frequently employed. In some mixtures, active ingredients having pre-emergence activity are combined with ingredients that possess postemergence activity. Herbicide mixtures used to control weeds in sugarcane may exhibit control for 90 days or longer. Effective long term weed control can eliminate the need for subsequent post-emergence herbicide treatments.

Because of the continued problem of weed pressure and the emergence of resistant weeds, there is an ongoing need for new herbicidal compositions and methods that provide both pre- and post- emergence control of weeds in sugarcane. Such compositions should provide long term control of weeds and have excellent sugarcane crop safety.

Detailed Description

It is well known in the agricultural chemical art that the interactions of agricultural chemicals are unpredictable. When two or more compounds are applied to plants they may display synergistic effects, additive effects, or antagonistic effects. Such effects cannot be predicted and experiments are required in order to discover which combinations of agricultural chemicals may be usefully combined to control weeds.

It has surprisingly been found that compositions of aminopyralid + diclosulam; aminopyralid + diclosulam + tebuthiuron; aminopyralid + diclosulam + clomazone; or aminopyralid + sulfentrazone + tebuthiuron show excellent control of weeds when applied pre-emergence to sugarcane.

As used herein, “aminopyralid” refers to any one or more of aminopyralid (4-amino-3,6- dichloropyridine-2-carboxylic acid, CAS 150114-71-9), aminopyralid-dimethylammonium (4- amino-3,6-di chloropicolinic acid - dimethylamine (1 :1)), aminopyralid potassium (potassium 4- amino-3,6-di chloropicolinate), aminopyralid tripromine (4-amino-3,6-di chloropicolinic acid - (2RS,2'RS,2"RS)-l,r,l"-nitrilotripropan-2-ol (1: 1)), aminopyralid choline, and any other agriculturally acceptable salts or esters. Aminopyralid is available as MILESTONE® from Corteva Agriscience.

As used herein “diclosulam” refers to diclosulam (2',6'-dichloro-5-ethoxy-7- fluoro[l,2,4]triazolo[l,5-c]pyrimidine-2-sulfonanilide, CAS 145701-21-9) and any agriculturally acceptable salts, esters, and other derivatives thereof. Diclosulam is available as Coact® from Dow AgroSciences Industrial Ltda.

As used herein “clomazone” refers to clomazone (2-(2-chlorobenzyl)-4,4-dimethyl-l,2- oxazolidin-3-one, 2-(2-chlorobenzyl)-4,4-dimethylisoxazolidin-3-one, CAS 81777-89-1) and any agriculturally acceptable salts, esters, and other derivatives thereof Clomazone is available as Gamit® CS from FMC QUIMICA DO BRASIL LTDA.)

As used herein “sulfentrazone” refers to sulfentrazone (N-{2,4-Dichloro-5-[4-(difluoromethyl)- 3-methyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-l-yl]phenyl}methanesulfonamide, CAS 122836- 35-5) and any agriculturally acceptable salts, esters, and other derivatives thereof Sulfentrazone is available as Boral® from FMC QUIMICA DO BRASIL LTDA.

As used herein “tebuthiuron” refers to tebuthiuron (l-(5-tert-butyl-l,3,4-thiadiazol-2-yl)-l,3- dimethylurea, CAS 34014-18-1) and any agriculturally acceptable salts, esters, and other derivatives thereof. Tebuthiuron is available as Combine® from Dow AgroSciences Industrial Ltda.

As used herein “ami carb azone” refers to amicarbazone (4-amino-N-tert-butyl-5-oxo-3-propan-2- yl-1, 2, 4-triazole-l -carboxamide, CAS 129909-90-6) and any agriculturally acceptable salts, esters, and other derivatives thereof. Amicarbazone is available as Dinamic® from UPL do Brasil Industria e Comercio de Insumos Agropecuarios S.A.

As used herein “sugarcane” refers to a tall perennial grass of the genus Saccharum that is used for sugar production. Sugarcane plants and crops may be species, and/or hybrids, and/or genetically modified.

As used herein, the terms “comprises,” “comprising,” or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.

As used herein “DAA” refers to Days After treatment Application.

As used herein “weed” or “weeds” refers to any unwanted vegetation that may interfere with the growth and/or harvesting of a desired crop. Weeds are known to compete for nutrients with crops such as sugarcane, lowering yields. In addition, weeds may interfere with mechanized harvesting machines, lowering harvesting efficiency. Weeds include, but are not limited to, the following: Jpomoea spp., Merremia spp., Mucuna spp., Riccinus Communis, Brachiaria decumbens, and Panicum maximum.

As used herein “mL cp/ha or g cp/ha” refers to the amount of herbicide formulation liquid (mL cp/ha) or herbicide formulation solid (g cp/ha) applied.

As used herein “g ai/ha” and “g ae/ha” refer to the amount of an active ingredient (ai) or the amount of an acid equivalent (ae) applied. As used herein, aminopyralid concentrations are expressed on an acid equivalent (ae) basis.

As used herein “dry season” refers to period around May to August in South-Center region of Brazil. In other regions of the world the dry season may occur during a different part of the calendar year.

As used herein “wet season” refers to period around September to March in South-Center region of Brazil. In other regions of the world the dry season may occur during a different part of the calendar year.

As used herein, a “herbicidally effective” or “vegetation controlling” or “weed controlling” amount is an amount of active ingredient(s) which causes an adversely modifying effect to the vegetation, such as a weed, causing deviations from natural development, killing, effecting regulation, causing desiccation, causing retardation, and the like.

As used herein, “controlling” undesirable vegetation or weeds means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation. Described herein are methods oof controlling undesirable vegetation through the application of certain herbicide combinations or compositions. Methods of application include, but are not limited to applications to the vegetation or locus thereof, e.g, application to the area adjacent to the vegetation, as well as pre-emergence, post-emergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), via hand, backpack, machine, tractor, oraerial (airplane and helicopter) application methods.

As used herein, “plants” and “vegetation” and “weeds” include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation and established vegetation. Tt has been surprisingly discovered that binary mixtures of aminopyralid and diclosulam are effective in controlling weeds in sugarcane. Aminopyralid may be used in a weight range from 50 - 200 g ai/ha and diclosulam may be used in a weight range from 60 - 100 g ai/ha.

Aminopyralid : diclosulam mixtures may be used in a weight ratio range from 1 :0.3 to 1 :2. The following exemplary mixtures (g ai/ha) of aminopyralid to diclosulam may be effective: 50:60, 50:65, 50:70, 50:75, 50:80, 50:85, 50:90, 50:95, 50: 100, 55:60, 55:65, 55:70, 55:75, 55:80,

55:85, 55:90, 55:95, 55:100, 65:60, 65:65, 65:70, 65:75, 65:80, 65:85, 65:90, 65:95, 65:100,

70:60, 70:65, 70:70, 70:75, 70:80, 70:85, 70:90, 70:95, 70:100, 75:60, 75:65, 75:70, 75:75,

75:80, 75:85, 75:90, 75:95, 75: 100, 80:60, 80:65, 80:70, 80:75, 80:80, 80:85, 80:90, 80:95,

80: 100, 85:60, 85:65, 85:70, 85:75, 85:80, 85:85, 85:90, 85:95, 85: 100, 90:60, 90:65, 90:70, 90:75, 90:80, 90:85, 90:90, 90:95, 90: 100, 95:60, 95:65, 95:70, 95:75, 95:80, 95:85, 95:90, 95:95, 95: 100, 100:60, 100:65, 100:70, 100:75, 100:80, 100:85, 100:90, 100:95, 100: 100, 105:60, 105:65, 105:70, 105:75, 105:80, 105:85, 105:90, 105:95, 105: 100, 110:60, 110:65, 110:70, 110:75, 110:80, 110:85, 110:90, 110:95, 110: 100, 115:60, 115:65, 115:70, 115:75, 115:80, 115:85, 115:90, 115:95, 115: 100, 120:60, 120:65, 120:70, 120:75, 120:80, 120:85,

120:90, 120:95, 120: 100, 125:60, 125:65, 125:70, 125:75, 125:80, 125:85, 125:90, 125:95,

125: 100, 130:60, 130:65, 130:70, 130:75, 130:80, 130:85, 130:90, 130:95, 130: 100, 135:60, 135:65, 135:70, 135:75, 135:80, 135:85, 135:90, 135:95, 135: 100, 140:60, 140:65, 140:70,

140:75, 140:80, 140:85, 140:90, 140:95, 140: 100, 145:60, 145:65, 145:70, 145:75, 145:80,

145:85, 145:90, 145:95, 145: 100, 150:60, 150:65, 150:70, 150:75, 150:80, 150:85, 150:90,

150:95, 150: 100, 155:60, 155:65, 155:70, 155:75, 155:80, 155:85, 155:90, 155:95, 155: 100,

160:60, 160:65, 160:70, 160:75, 160:80, 160:85, 160:90, 160:95, 160: 100, 165:60, 165:65,

165:70, 165:75, 165:80, 165:85, 165:90, 165:95, 165: 100, 170:60, 170:65, 170:70, 170:75,

170:80, 170:85, 170:90, 170:95, 170: 100, 175:60, 175:65, 175:70, 175:75, 175:80, 175:85,

175:90, 175:95, 175: 100, 180:60, 180:65, 180:70, 180:75, 180:80, 180:85, 180:90, 180:95,

180: 100, 185:60, 185:65, 185:70, 185:75, 185:80, 185:85, 185:90, 185:95, 185: 100, 190:60, 190:65, 190:70, 190:75, 190:80, 190:85, 190:90, 190:95, 190: 100, 195:60, 195:65, 195:70, 195:75, 195:80, 195:85, 195:90, 195:95, 195: 100, 200:60, 200:65, 200:70, 200:75, 200:80, 200:85, 200:90, 200:95, and 200:100.

It has surprisingly been discovered that certain ternary mixtures of herbicides are effective in controlling weeds in sugarcane. For example, mixtures of diclosulam plus tebuthiuron plus aminopyralid in a ratio of 105 : 1800 : 500 mL cp/ha or g cp/ha; diclosulam plus clomazone and aminopyralid in a ratio of 105 : 3000 : 800 mL cp/ha or g cp/ha; and sulfentrazone plus tebuthiuron plus aminopyralid in a ratio of 1600 : 3000 : 800 mL cp/ha are effective against weeds in sugarcane. These compositions may be prepared using the formulated products listed above, or with other formulations of the active ingredients, or with technical grade active ingredients, or in other ways that are known in the art. The active ingredient components of the compositions may be applied simultaneously or sequentially, preemergence or postemergence, wet season or dry season.

We have found that weeds in sugarcane may be controlled by: contacting the vegetation or the locus thereof with or applying to the soil to control the emergence or growth of weeds a herbicidally effective amount of (a) aminopyralid and (b) diclosulam to a crop of sugarcane in need of weed control; and wherein (a) is applied at a rate from 50 g ae/ha to 200 g ae/ha and (b) is applied at a rate from 60 g ai/ha to a 100g ai/ha. The aminopyralid may be in the form of aminopyralid acid, aminopyralid dimethylamine salt, aminopyralid potassium salt, aminopyralid choline salt, or aminopyralid tripromine salt. Preferably aminopyralid is applied at a rate from 70 g ae/ha to 126 g ae/ha. Preferably diclosulam is applied at a rate from 70 g ae/ha to a 90g ae/ha. Preferably the acid equivalent weight ratio of aminopyralid to diclosulam is from 1 :0.3 to 1:2. The compositions may be prepared using the formulated products listed above, or with other formulations of the active ingredients, or with technical grade active ingredients, or in other ways that are known in the art. The compositions may be applied pre-emergence or post-emergence to a sugarcane crop. The compositions may be applied during the dry season or the wet season. The active ingredient components of the composition (aminopyralid and diclosulam) may be applied simultaneously or sequentially.

It has been found that weeds in sugarcane may be controlled by: contacting the vegetation or the locus thereof with or applying to the soil to control the emergence or growth of weeds a herbicidally effective amount of diclosulam plus tebuthiuron plus aminopyralid in a ratio of 105 : 1800 : 500 mL cp/ha or g cp/ha; and wherein diclosulam is applied at a rate of 105 g cp/ha and tebuthiuron is applied at a rate of 1800 mL cp/ha and aminopyralid is applied at a rate from 500 mL cp/ha. The aminopyralid may be in the form of aminopyralid acid, aminopyralid dimethylamine salt, aminopyralid potassium salt, aminopyralid choline salt, or aminopyralid tripromine salt. Preferably diclosulam is applied at a rate of 105 g cp/ha. Preferably aminopyralid is applied at a rate of 500 mb cp/ha. Preferably tebuthiuron is applied at a rate of 1800 mb cp/ha. The composition may be prepared using the formulated products listed above, or with other formulations of the active ingredients, or with technical grade active ingredients, or in other ways that are known in the art. The composition may be applied pre-emergence or post-emergence to a sugarcane crop. The composition may be applied during the dry season or the wet season. The active ingredient components of the composition (tebuthiuron and aminopyralid and diclosulam) may be applied simultaneously or sequentially.

We have found that weeds in sugarcane may be controlled by: contacting the vegetation or the locus thereof with or applying to the soil to control the emergence or growth of weeds a herbicidally effective amount of diclosulam plus clomazone and aminopyralid in a ratio of 105 : 3000 : 800 mb cp/ha or g cp/ha; and wherein aminopyralid is applied at a rate from 800 mb cp/ha and diclosulam is applied at a rate of 105 g cp/ha and clomazone is applied at a rate of 3000 mL cp/ha. The aminopyralid may be in the form of aminopyralid acid, aminopyralid dimethylamine salt, aminopyralid potassium salt, aminopyralid choline salt, or aminopyralid tripromine salt. Preferably aminopyralid is applied at a rate of 800 mL cp/ha. Preferably clomazone is applied at a rate of 3000 mL cp/ha. Preferably diclosulam is applied at a rate from 105 g cp/ha. The composition may be prepared using the formulated products listed above, or with other formulations of the active ingredients, or with technical grade active ingredients, or in other ways that are known in the art. The composition may be applied pre-emergence or post-emergence to a sugarcane crop. The composition may be applied during the dry season or the wet season. The active ingredient components of the composition (aminopyralid and diclosulam and clomazone) may be applied simultaneously or sequentially.

We have found that weeds in sugarcane may be controlled by: contacting the vegetation or the locus thereof with or applying to the soil to control the emergence or growth of weeds a herbicidally effective amount of sulfentrazone plus tebuthiuron plus aminopyralid in a ratio of 1600 : 3000 : 800 mL cp/ha; and wherein sulfentrazone is applied at a rate of 1600 mL cp/ha and tebuthiuron is applied at a rate of 3000 mL cp/ha and aminopyralid is applied at a rate from 800 mL cp/ha. The aminopyralid may be in the form of aminopyralid acid, aminopyralid dimethylamine salt, aminopyralid potassium salt, aminopyralid choline salt, or aminopyralid tripromine salt. Preferably sulfentrazone is applied at a rate of 1600 mL cp/ha. Preferably aminopyralid is applied at a rate of 800 mL cp/ha. Preferably tebuthiuron is applied at a rate of 3000 mL cp/ha. The composition may be prepared using the formulated products listed above, or with other formulations of the active ingredients, or with technical grade active ingredients, or in other ways that are known in the art. The composition may be applied pre-emergence or post-emergence to a sugarcane crop. The composition may be applied during the dry season or the wet season. The active ingredient components of the composition (sulfentrazone and aminopyralid and tebuthiuron) may be applied simultaneously or sequentially.

Experimental Results

Field studies were performed to determine the efficacy of aminopyralid, alone or combined with other partners, in both pre- and post-emergence applications for weed control in sugarcane. Aminopyralid was tested pre- and post-emergence against weeds using formulation MILESTONE® at rates from 70 to 126 g ae/ha. The MILESTONE® aminopyralid formulation was used both alone and combined with other active ingredients. Combinations tested include mixtures of aminopyralid combined with diclosulam, aminopyralid combined with diclosulam and clomazone, aminopyralid combined with diclosulam and tebuthiuron, and aminopyralid combined with sulfentrazone and tebuthiuron. Test results were compared to results obtained with standard treatments.

All treatments were diluted in water and a single application for each study (backpack sprayer) was performed delivering 150 L of spray solution per ha. Weed control and sugarcane selectivity were assessed by visual percentage scale (0% is no effect and 100% is complete control). Preemergence tests were sprayed between 0 and 21 days after planting, typically at planting. Postemergence tests were sprayed after the emergence of sugarcane or weeds, typically between 21 and 150 days after planting. Significance of treatment effect was evaluated with F- approximate test (u=0.1) and least square means from different treatments were compared with Tukey’s test. Compounds and mixtures were tested using formulated active ingredients. The names and concentrations and amount of active ingredients in the compositions are listed in Table 1. Test results are shown in Tables 2-14.

Table 1 . Formulation Names and active ingredient concentrations

Table 2. Brachiaria decumbens (BRADC) percent control at 60, 90 and 120 DAA - preemergence.

Table 3. Brachiaria decumbens (BRADC) control at 90, 120 and 150 DAA - pre-emergence.

Tested on ratoon sugarcane during the dry period in Brazil.

Table 4. Panicum maximum (PANMA) control at 60, 120 and 150 DA A - pre-emergence.

Table 5. Brachiaria decumbens and Digitaria spp. (DIGSS) control at 45, 90 and 120 DAA - pre-emergence.

Table 6. Jpomoea grandifolia (TAQGR) control at 60, 120 and 150 DA A - pre-emergence.

Table 7. Ipomoea grandifolia (IAQGR) control at 60, 120 and 150 DAA - pre-emergence.

Table 8. Mucuna pruriens (MUCPR) control at 90, 150 and 180 DAA - pre-emergence. Tested on ratoon sugarcane during the dry period in Brazil.

Table 9. Ricinus communis (RIICO) control at 90, 150 and 180 DAA - pre-emergence . Tested on ratoon sugarcane during the dry period in Brazil.

Table 10. Jpomoea hederifolia (TPOHF) control at 45, 90 and 120 DAA - pre-emergence.

Table 11 . Mucuna pruriens (MUCPR) control at 45, 90 and 120 DAA - pre-emergence.

Table 12. Ricimus communis (RTTCO) control at 45, 90 and 120 DAA - pre-emergence.

Table 13. Merremia aegyptia (IPOPE) and Jpomoea spp. (IPOSS) control at 15 and 30 DA A - post-emergence.

Table 14. Ricimts communis (RTTCO) and Mucuna pruriens (MUCPR) control at 15 and 30 DA A

- post-emergence.

No significant crop injury was observed in any treatment.

As shown in the Tables above aminopyralid alone or mixed with other herbicides tested displayed efficacy against key weed species and selectivity for sugarcane. The following compositions, aminopyralid plus diclosulam; aminopyralid plus diclosulam plus tebuthiuron; aminopyralid plus diclosulam plus clomazone; aminopyralid plus sulfentrazone plus tebuthiuron all demonstrated effective pre-emergence and post-emergence performance from to 90 to 210 DAA against key weeds. The control of these weeds enhances the production of sugarcane by minimizing weed competition.

When harvesting sugarcane, time is of the essence. Once the canes are cut, they begin to deteriorate. Freshly cut canes need to be delivered quickly to a processing mill to maximize sugar production. The excellent herbicidal effects demonstrated above eliminate or minimize problems caused by late weed infestations that interfere with mechanized sugarcane harvesting Harvester efficiency is improved by minimizing the need to halt harvesting for machine cleaning (removing weed debris from harvesting machinery). As a result, overall costs are lowered, harvesting performance is increased, and sugar production is maximized.

Claims

Claims We claim:

1. A method of controlling weeds in sugarcane comprising: contacting the vegetation or the locus thereof with or applying to the soil to control the emergence or growth of weeds a herbicidally effective amount of (a) aminopyralid and (b) diclosulam to a crop of sugarcane in need of weed control; and wherein (a) is applied at a rate from 50 g ae/ha to 200 g ae/ha and (b) is applied at a rate from 60 g ai/ha to a 100g ai/ha.

2. The method of claim 1 wherein the aminopyralid is an agriculturally acceptable aminopyralid salt.

3. The method of claim 1 wherein the aminopyralid is aminopyralid acid, aminopyralid dimethylamine salt, aminopyralid potassium salt, aminopyralid choline salt, or aminopyralid tripromine salt.

4. The method of claim 1 wherein (a) is applied at a rate from 70 g ae/ha to 126 g ae/ha.

5. The method of claim 1 wherein (b) is applied at a rate from 70 g ai/ha to a 90g ai/ha.

6. The method of claim 1 wherein the acid equivalent weight ratio of (a) to (b) is from 1:0.3 to

1 :2.

7. The method of claim 1 wherein (a) and (b) are applied pre-emergence to a sugarcane crop.

8. The method of claim 1 wherein (a) and (b) are applied post-emergence to a sugarcane crop.

9. The method of claim 1 wherein (a) and (b) are applied during the dry season.

10. The method of claim 1 wherein (a) and (b) are applied during the wet season.

1 1 . The method of claim 1 wherein (a) and (b) are applied simultaneously.

12. The method of claim 1 wherein (a) and (b) are applied sequentially.