WO2000049869A1 - Adjuvants destines a des compositions herbicides - Google Patents

Adjuvants destines a des compositions herbicides Download PDF

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Publication number
WO2000049869A1
WO2000049869A1 PCT/US2000/004686 US0004686W WO0049869A1 WO 2000049869 A1 WO2000049869 A1 WO 2000049869A1 US 0004686 W US0004686 W US 0004686W WO 0049869 A1 WO0049869 A1 WO 0049869A1
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WIPO (PCT)
Prior art keywords
adjuvant
adjuvant composition
composition
composition according
spray
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Application number
PCT/US2000/004686
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English (en)
Inventor
John D. Nalewaja
Robert Matsiak
Zenon Woznica
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Ndsu Research Foundation
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Publication date
Application filed by Ndsu Research Foundation filed Critical Ndsu Research Foundation
Priority to AU36040/00A priority Critical patent/AU3604000A/en
Publication of WO2000049869A1 publication Critical patent/WO2000049869A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds

Definitions

  • This invention relates to two component water soluble adjuvant compositions for use in spray carriers containing postemergence herbicides, which are used to control weeds or other undesired vegetation.
  • Herbicides used in controlling weeds or undesired vegetation in agriculture are customarily applied by postemergence spraying of a herbicide on the crop.
  • the spray carrier for the herbicide is usually a water based solution containing an effective amount of known herbicide.
  • Adjuvants are commonly added to herbicidal spray solutions to enhance postemergence weed control and/or to reduce spray drift during herbicide applications.
  • Postemergence weed control requires that the spray containing the herbicide be retained on the weed surface for that purpose.
  • many "sticker" compositions or agents including methylated vegetable oils or mineral based oils and wetting (surface/active) agents are marketed for spray solution adherence of the herbicide by the weeds and in addition help retain droplets of the spray solution on the plant and to penetrate into the plant.
  • adjuvants differ greatly in herbicide enhancement depending on the specific surfactant and the herbicide used in some cases resulting in decreased performance. Halloway, 4th International Symposium on Adjuvants for Agrochemicals . 1995, FR. & Bulletin, No. 193) .
  • Adjuvants which are a three component system including an alkaline amine pH regulator, a non- ionic surfactant, and a neutral ammonium such as ammonium nitrate, ammonium chloride, and ammonium sulfate are described in U.S. Patent No. 5,658,855. All three components were required to provide the desired phytotoxicity.
  • the present invention relates to adjuvant compositions for use in the spray carrier of postemergence herbicides applied as an aqueous spray solution to areas infested with undesired weeds or plants to control the same.
  • the adjuvant composition is substantially free of neutral ammonium salts which act as a fertilizer and or herbicidal enhancer.
  • the present invention does not require neutral ammonium salts, such as ammonium nitrate, ammonium chloride and ammonium sulfate, to provide an enhancement of herbicidal activity.
  • the adjuvant composition of the invention is a two component composition that includes an amine or ammonia compound which is a base for adjusting the pH to the alkaline range, and a non- ionic surface active agent with a high Hydrophilic-Lipophilic Balance (HLB) , which functions as a spreader or sticker and penetrant for use with postemergence herbicides.
  • the basic or alkaline amine pH regulator of the invention is effective for providing an alkaline pH of above about 7 up to about 9 to the final spray solution that is applied to the plants.
  • Alkaline compounds effective for providing a basic spray solution may include various amine or ammonium compounds which are employed in amounts of up to about 30% by weight of the adjuvant composition.
  • Amine type compounds useful in the present invention include ammonium hydroxide, and water soluble amines such as monoethanolamine, diethanolamine, triethanolamine and 2-amino-2 -ethyl-1, 3-propanediol .
  • the second component of the adjuvant composition of the present invention is a non- ionic surfactant.
  • the non-ionic surfactants have a high HLB (Hydrophilic-Lipophilic Balance) above about 12 to about 18.
  • HLB Hydrophilic-Lipophilic Balance
  • the non- ionic surfactant component ranges from about 25 to about 95 percent by weight of the adjuvant composition.
  • the adjuvant compositions of the present invention are diluted with water and blended with a herbicide in herbicidally effective amounts and applied for weed control purposes.
  • the herbicide is customarily added to the adjuvant/water solution at the recommended label amount, for example, in an amount effective for providing an application rate of broadly from about 0.12 to about 2 ounces per acre of the active herbicide ingredient.
  • the adjuvant composition and herbicidal spray composition of the invention is substantially free of a neutral ammonium salt composition and still remains as effective as a herbicidal adjuvant with three components that includes an ammonium salt.
  • Neutral ammonium salt compositions include nitrogen fertilizers such as ammonium nitrate, ammonium chloride, ammonium nitrate-urea fertilizer solutions, and ammonium sulfate.
  • less than effective amount of neutral ammonium salt composition means less than about 1% by weight based on the weight of the adjuvant composition and less than about 0.1% by weight based on the weight of the herbicidal spray composition.
  • the adjuvant of the present invention is a two component mixture including an alkaline amine pH regulator and a non-ionic surfactant, the adjuvant being substantially free of neutral ammonium salts.
  • the two component adjuvant composition of the present invention increases the efficacy of certain herbicides.
  • a third ammonium salt component for example a ammonium fertilizer, allows for the production of a more concentrated product that can be used at lower percentages.
  • the two component adjuvant of the invention is as effective as the three component adjuvant described in U.S. Patent No. 5,658,855 for increasing the herbicidal activity of the same herbicide at the same concentrations of adjuvant and herbicide.
  • Substantially free of neutral ammonium salts having a fertilizer enhancing action means that the adjuvants of the invention do not have amounts of these salts which are effective for fertilizer or herbicidal enhancing activity, such as less than about 1 wt % of the adjuvant, when the adjuvant is applied in an effective amount as a part of a herbicidal spray.
  • Alkaline Amine pH Regulator
  • high pH in combination with surfactants increased phytotoxicity of herbicides and resulted in a fresh weight reduction of weeds.
  • the combination of high pH and surfactant resulted in increased phytotoxicity to weeds by at least 12% at low spray volumes of about 80 L/ha.
  • the alkaline amine pH regulator of the invention provides an alkaline pH of the final spray solution of above about 7 up to about 9.
  • the upper limit of pH chosen should not be so high as to result in hydrolysis of the herbicidal use.
  • the lower pH limit should be slightly above 7 in the alkaline range, for example, 7.25.
  • the alkaline component is free of calcium or sodium cations. As used herein, “free of calcium or sodium cations" or “substantially free of herbicidally antagonistic amounts of calcium or sodium cations” means that the alkaline component has less than about 0.01 percent by weight calcium or sodium cations.
  • Alkaline components which contain calcium or sodium cations should be avoided since these are considered antagonistic to many herbicides.
  • Alkaline compounds which include nitrogen are especially important in the present invention.
  • Preferred alkaline compounds used to provide an alkaline spray solution are various amine or ammonium compounds which are employed in amounts of up to about 30% by weight of the adjuvant composition.
  • Useful amine type compounds are ammonium hydroxide, and water soluble amines.
  • Amines such as monoethanolamine, diethanolamine, triethanolamine and 2-amino-2-ethyl-1,3 -propanediol are examples of preferred pH regulators.
  • the second component of the adjuvant composition is a non- ionic surfactant preferably secondary or linear (primary) alcohols or other non- ionic surfactants having a high HLB (Hydrophilic-Lipophilic Balance) broadly above about 12 to about 18; preferably between 13 and 17.
  • HLB Hydrophilic-Lipophilic Balance
  • the non- ionic surfactant may also be block copolymers of various HLB's.
  • High HLB indicates that a surfactant molecule is relatively more water than oil soluble.
  • One system of obtaining HLB is by dividing the water soluble portion of the surfactant molecule by 5.
  • HLB values for surfactants are usually provided by the surfactant supplier and are also available from McCutcheon's Emulsifiers & Detergents, McCutcheon Division, McCutcheon Publishing Co., 175 Rock Road, Glen Rock, NJ 07452).
  • High HLB's of the present invention are considered hydrophilic.
  • water soluble herbicides are enhanced more by high than low HLB surfactants .
  • Suitable non- ionic surfactants having a high HLB are ethoxylated alkylphenols, Triton X-100 (HLB 13.5), Triton X-102 (HLB 14.6), Triton X-165 (HLB 15.8), Triton X-305 (HLB 17.3) from Union Carbide Corporation, Igepal CO-610 (HLB 12.2), CO-660 (HLB 13.2), CO-720 (HLB 14.2), CO-730 (HLB 15), CO-887 (HLB 17.2) from R one- Poulenc, GENAPOL 24-L-75, an ethoxylated alcohol, product of Hoechst Celanese Corp., (HLB 10.9); Pluronics, block copolymers of propylene oxide and ethylene oxide, products of BASF Corp., (P103, HLB up to 12; P104, HLB 12-18) ; Tween 20, polyoxethylene (20) sorbitan monolaurate, product of ICI Surfactants, (HL
  • the adjuvant is customarily formulated and sold in two and one half [2 ) gallon or larger batches which are used to make up the spray mixture which includes spray water (about 99%) and a herbicidally effective amount of a postemergence herbicide.
  • the adjuvant of the present invention is effective for use with herbicides whose solubility is increased by high pH, which includes sulfonylureas and weak acid herbicides.
  • the surfactant of the present invention acts to help spray retention and absorption by plants and the high pH maintains the herbicide in a more efficacious chemical form for absorption.
  • the herbicides employed in this invention are selected from the group consisting of:
  • Nicosulfuron (sold under the tradename Accent) which is the compound [ [ [ [ [ (4, 6-demethoxy-2- ⁇ yrimidinyl) amino] carbonyl] amino] sulfonyl-N,N-dimethyl-3-pyridine carboxy amide;
  • Sulfsulfuron (sold under the tradename Maverick) which is the compound 1- (2-ethylsulfonylimidazo (1, 2- a) pyridin-3-ylsulfonyl ) -3 ( 4 , 6-dimethoxypyrimidin-2- yl)urea; and
  • Quinchlorac (sold under the tradename Facet) which is the compound 3, 7-dichloro-8-quinolinecarboxylic acid.
  • Sulfonylurea and i idazolinone herbicides such as rimsulfuron (Matrix), N( (4, 6-dimethoxypyrimidin- 2yl) aminocarbonylO-3- (ethysulfonly) -2- pyridinesulfonamide; trisulfuorn (UpBeet) , methyl-2- [ [ [[ [4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-l,3,5- triazin-2-yl] amino] carbonyl] amino] sulfonyl) -3- methylbenzoate; imazethapyr (Pursuit), imazamox, ( ⁇ )-2- [4, 5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-
  • A an amino alkaline pH regulator compound selected from the group consisting of ammonium hydroxide; monoethanolamine, diethanolamine, triethanolamine, and 2- amino- 2-ethyl -1, 3 -propanediol and mixtures thereof in sufficient amount to provide a pH of from about 7.25 to about 9 in the final diluted aqueous composition;
  • B a non- ionic surface active agent having an HLB of from about 12 to about 18 in an amount from about 25% to about 95% by weight of said adjuvant composition;
  • the post emergence herbicidal aqueous spray composition utilizing the adjuvant compositions of this invention comprise from about 0.15 to 0.8% and preferably 0.2 to 0.5% of a non- ionic surfactant having a high Hydrophylic-Lipophylic Balance (HLB) ; an alkaline amine type pH regulator selected from the group consisting of ammonium hydroxide, monoethanol amine, diethanolamine, triethanolamine and 2 -amino-2 -ethyl -1,3 -propanediol in an amount to provide a pH of from about 7.25 to about 9 in the final aqueous solution.
  • HLB Hydrophylic-Lipophylic Balance
  • Example 1 The effect of surfactant, pH and spray volume on weight reduction of crabgrass was tested as shown in Table 1. High pH in combination with Tergitol 15-S-, Igepol CO, and Triton X surfactants was positive to increasing nicosulfuron phytotoxicity to large crabgrass as measured by fresh weight reduction (Table l) . Both the high pH and the surfactant enhanced the efficacy of nicosulfuron regardless of spray volume. At the low spray volume of 80 L/ha increasing the pH from 4 to 9 with ammonium hydroxide increased the effectiveness of all three types of surfactants regardless of surfactant HLB. At the high spray volume of 240 L/ha the benefit from high pH was limited to the less effective surfactants.
  • Igepal CO 720 14.2 49 95 93 94 Igepal CO 730 15.0 53 9 95 96 Igepal CO 887 17.2 27 89 88 91 Igepal CO 997 19.0 9 69 75 82 LSD 5% 19.0 9 69 75 82 -- 6 --
  • Triton ® X-45 10.4 0 21 1 11 Triton ® X-114 12.4 13 54 49 60 Triton ® X-100 13.5 7 71 68 84 Triton ® X-102 14.6 9 76 80 85 Triton ® X-165 15.8 3 85 76 84 Triton ® X-305 17.3 -5 72 70 79 Triton ® X-405 17.9 -11 58 48 65 LSD 5% -- 9 --
  • Igepal Surfactants are from Rhone-Poulenc, Cranberry, NJ, Tergitol ® products and Triton ® X from Union Carbide, Danbury CT.
  • b pH4 was hydrochloric acid and 9 by ammonium hydroxide.
  • C HLB is the surfactant hydrophilic-lipophilic-balance value .
  • d LSD is Least Significant Difference.
  • Table 2 show that the addition of ammonium nitrate to the adjuvant composition did not further enhance nicosulfuron efficacy with Tergitols in a distilled water carrier.
  • b HLB is the surfactant hydrophilic-lipophilic-balance value .
  • Table 3 demonstrates the effect of different surfactants and material used to increase pH on % weight reduction of crabgrass.
  • Table 3 Large crabgrass control from Nicosulfuron at 15 g/ha with pH material.
  • Table 4 shows the effect of high pH from various ammonium compounds. Ammonium hydroxide, dibasic phosphate, and tribasic citrate were most effective in the enhancement of nicosulfuron with either X-77 or Tween 20 surfactants.
  • Table 5 shows the effect of pH, fertilizer and surfactant on the efficacy of sulfsulfuron herbicide.
  • LAE linear alcohol ethoxylates.
  • AMN ammonium nitrate fertilizer.
  • Table 6 shows the effect of pH, and surfactant on the efficacy of quinchlorac herbicide.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition d'adjuvant destinée à être utilisée dans des compositions herbicides. L'adjuvant comprend un composé d'amine alcaline et un agent tensioactif non-ionique, et ne contient pratiquement pas de composition de sel d'ammonium neutre.
PCT/US2000/004686 1999-02-24 2000-02-24 Adjuvants destines a des compositions herbicides WO2000049869A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU36040/00A AU3604000A (en) 1999-02-24 2000-02-24 Adjuvants for herbicidal compositions

Applications Claiming Priority (2)

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US25715299A 1999-02-24 1999-02-24
US09/257,152 1999-02-24

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WO2000049869A1 true WO2000049869A1 (fr) 2000-08-31

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8071508B2 (en) 2002-09-12 2011-12-06 E. I. Du Pont De Nemours And Company Process for preparing paste-extruded sulfonamide compositions
GB2503416A (en) * 2012-04-20 2014-01-01 Rotam Agrochem Int Co Ltd Sulfonylurea composition for spray tank cleanout
WO2018057684A1 (fr) * 2016-09-26 2018-03-29 Monsanto Technology Llc Compositions herbicides à symptôme rapide contenant un herbicide organophosphoré, du bipyridilium et un agent tensioactif alcoolique alcoxylé

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3964896A (en) * 1971-08-09 1976-06-22 Uniroyal, Inc. Oxadiazole benzoic acid derivatives as herbicides
US5658855A (en) * 1996-09-26 1997-08-19 North Dakota State University Adjuvants for herbicidal compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3964896A (en) * 1971-08-09 1976-06-22 Uniroyal, Inc. Oxadiazole benzoic acid derivatives as herbicides
US5658855A (en) * 1996-09-26 1997-08-19 North Dakota State University Adjuvants for herbicidal compositions

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GREEN ET. AL.: "Surfactant Structure and Concentration Strongly Affect Rimsulfuron Actitvity", WEED TECHNOLOGY, vol. 7, 1993, pages 633 - 640, XP002929374 *
NALEWAJA ET. AL.: "Salts and Surfactants Influence Nicosulfuron Activity", WEED TECHNOLOGY, vol. 9, 1995, pages 587 - 593, XP002929373 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8071508B2 (en) 2002-09-12 2011-12-06 E. I. Du Pont De Nemours And Company Process for preparing paste-extruded sulfonamide compositions
GB2503416A (en) * 2012-04-20 2014-01-01 Rotam Agrochem Int Co Ltd Sulfonylurea composition for spray tank cleanout
US9681663B2 (en) 2012-04-20 2017-06-20 Rotam Agrochem International Company Limited Method for spray tank cleanout
GB2503416B (en) * 2012-04-20 2017-07-19 Rotam Agrochem Int Co Ltd Method for spray tank cleanout
US10051865B2 (en) 2012-04-20 2018-08-21 Rotam Agrochem International Company Limited Method for spray tank cleanout
WO2018057684A1 (fr) * 2016-09-26 2018-03-29 Monsanto Technology Llc Compositions herbicides à symptôme rapide contenant un herbicide organophosphoré, du bipyridilium et un agent tensioactif alcoolique alcoxylé

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Publication number Publication date
AU3604000A (en) 2000-09-14

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