WO2003007716A1 - Composition pesticide liquide contenant un inhibiteur de croissance cristalline - Google Patents

Composition pesticide liquide contenant un inhibiteur de croissance cristalline Download PDF

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Publication number
WO2003007716A1
WO2003007716A1 PCT/IL2001/000654 IL0100654W WO03007716A1 WO 2003007716 A1 WO2003007716 A1 WO 2003007716A1 IL 0100654 W IL0100654 W IL 0100654W WO 03007716 A1 WO03007716 A1 WO 03007716A1
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WO
WIPO (PCT)
Prior art keywords
pva
azole
composition
crystal growth
azole fungicide
Prior art date
Application number
PCT/IL2001/000654
Other languages
English (en)
Inventor
Ofer Toledano
Original Assignee
Makhteshim Chemical Works Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Makhteshim Chemical Works Ltd. filed Critical Makhteshim Chemical Works Ltd.
Priority to PCT/IL2001/000654 priority Critical patent/WO2003007716A1/fr
Priority to ARP020102669A priority patent/AR034800A1/es
Publication of WO2003007716A1 publication Critical patent/WO2003007716A1/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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to the field of pesticidal compositions, particularly to the use of polyvinyl alcohol as a crystal growth inhibitor in said compositions.
  • EP 637,202 describes a liquid pesticidal composition containing as a crystallization inhibitor benzene which contains two or three hydroxy groups and substituted by one or more lower alkyl groups.
  • crystallization inhibitors are organic substances which are essentially insoluble in an aqueous medium.
  • the current practice in pest control is to reduce the use of organic solvents.
  • WO 00/35284 describes an aqueous suspension concentrate of triazole fungicides which contains a tristyrylphenol-ethoxylate, phosphate or sulfate thereof, with a vinylpyrrolidon polymer or copolymer thereof, as a crystal growth inhibitor.
  • a mixture of crystallization inhibitors at least a binary mixture thereof.
  • crystal growth inhibitors disclosed in the prior publications do not offer a solution for all needs, practices and conditions employed in agriculture.
  • the crystal growth inhibitor may vary in accordance with the active ingredient.
  • a further purpose of the present invention is to present the new use of a compound as a crystal growth inhibitor.
  • the present invention provides a liquid pesticidal composition comprising one or more azole fungicides and polyvinyl alcohol (PVA) as a crystal growth inhibitor.
  • PVA polyvinyl alcohol
  • PNA polyvinyl alcohol
  • the present invention further provides a method for inhibiting crystal growth of azole fungicides which are present in liquid pesticidal compositions comprising of adding PVA, as a crystal growth inhibitor, to liquid azole-containing fungicidal compositions.
  • polyvinyl alcohol refers to a polymer of vinyl alcohol with an average molecular weight in the range of 200 to 200,000.
  • azole or “azole fungicide” also means mixtures thereof.
  • PNA polyvinyl alcohol
  • a liquid pesticidal composition comprising 1% to 60% of an azole fungicide selected from among a group consisting of epoxiconazole, tebuconazole, cyproconazole, prochloraz (Zn, Cu and Mn complexes), penconazole, definoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon, tetraconazole and imibenconazole; and 0.1% to 30% of PNA, wherein PVA is a crystal growth inhibitor.
  • the weight ratio between the azole fungicide and PVA is 50:1 to 1:10. According to a preferred embodiment of the invention, the weight ratio between the azole fungicide and PVA is 50:1 to
  • compositions of the present invention are aqueous compositions which contain more than about 10% water.
  • aqueous compositions which contain more than about 10% water.
  • ⁇ on-limiting examples of such compositions are: suspension concentrates (SC) and emulsion in water (EW) formulations.
  • Compositions of the present invention may further comprise an additional pesticide which is not an azole fungicide.
  • Said pesticide selected from among a group comprising of strobilurin analogues, e.g. kresoxim-methyl and pyraclostrobin; morpholines, e.g., fenpropidin and fenpropimorph; quinoxyfen, spiroxamine, chlorothalonil, maneb, mancozeb, ziram, thirarn and ⁇ -thiahalomethyl derivatives, e.g., captan and folpet.
  • strobilurin analogues e.g. kresoxim-methyl and pyraclostrobin
  • morpholines e.g., fenpropidin and fenpropimorph
  • quinoxyfen spiroxamine
  • chlorothalonil maneb, mancozeb, ziram
  • thirarn ⁇ -thiahal
  • compositions according to the present invention may further contain organic solvents, surfactant agents, thickeners, anti-foaming agents, dispersing agents and wetting agents.
  • organic solvents which may be employed in the present invention can be aromatic or aliphatic, polar or non-polar solvents which are customarily used in the preparation of pesticidal compositions.
  • Non-limiting examples of said solvents include amides such as dimethylformaide, N,N-dimethylacetamide; ketones such as cyclohexanone, methylisobutyl ketone; aromatics such as benzene, toluene, xylene, mineral oil, naphthalenes; aliphatic hydrocarbons such as hexane and cyclohexane; N-pyrrolidone derivatives; ethers; esters; fatty acid esters; alcohols; glycols; sulphoxides and plant oils.
  • the solvent is 0% to 50% of the composition.
  • 0% to 40% of the present composition may be surfactant agents wherein non-limiting examples of suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants will also be understood as comprising mixtures of surfactants.
  • Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.
  • Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C 10 -C 2 ), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, e.g. from coconut oil or tallow oil.
  • Further suitable surfactants are also the fatty acid methyltaurin salts as well as modified and unmodified phospholipids.
  • so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkali earth metal salts or unsubstituted or substituted ammonium salts and contain a C 8 -C 22 alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids.
  • acyl radicals e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids.
  • These compounds also comprise the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde condensation product.
  • corresponding phosphates e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide.
  • Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
  • non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • non-ionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.
  • Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C 8 -C 2 alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)emylammomum bromide, preferably 1% to 5%.
  • Suitable thickeners for the present invention are, e.g., xanthan gum, polysaccharides and ethoxylated dialkyl phenols which are present in the composition in 0.01% to 2%, preferably 0.1% to 1%.
  • Anti-foaming agents (AF) suitable for use in the present composition are those customarily employed in pesticidal compositions, wherein non-limiting examples of said agents are silicon oils or silicon oil emulsions in water commercially available as, e.g., Rhodorsil 432, Sag 470 and Dow Corning 1520, wherein 0% to 5% of anti-foaming agent are employed, preferably 0.1% to 1%.
  • the present composition may further comprise 0% to 10% of a wetting agent wherein said wetting agent may be selected from the non-limiting examples presented under the surface active agents. Preferably, 1% to 3% wetting agent is employed.
  • a fungicidal composition of epoxiconaole comprising 5% to 25% of epoxiconazole, 1% to 5% PVA, 0.1% to 1% anti-foaming agent, 10% to 50% aromatic solvent, 0.05% to 5% thickener and 10% to 90% water.
  • the present invention further relates to the use of PVA as a crystal growth inhibitor in pesticidal compositions which contain 1% to 60% of an azole fungicide selected from among a group consisting of epoxiconazole, tebuconazole, cyproconazole, prochloraz, penconazole, definoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon, tetraconazole and imibenconazole, wherein the crystal growth inl ibiting effect of PVA is achieved when said composition contains 0.1% to 30% of PVA.
  • an azole fungicide selected from among a group consisting of epoxiconazole, tebuconazole, cyprocon
  • Said effect can also be achieved by maintaining a weight ratio between the azole fungicide and PVA in the range of 50:1 to 1:10.
  • the weight ratio between the azole fungicide and PVA is 20: 1 to 1 : 1.
  • a method for preventing crystal growth of azole fungicides which are present in liquid pesticidal compositions comprising of adding PVA to liquid azole-containing fungicidal compositions.
  • PVA is added to a fungicidal azole-containing pesticidal composition so that the weight ratio between the azole fungicide and the PVA is in the range of 50: 1 to 1 : 10, preferably 20: 1 to 1 : 1.
  • the fungicidal azole suitable for the present method is selected from among a group consisting of epoxiconazole, tebuconazole, cyproconazole, prochloraz (Zn, Cu and Mn complexes), penconazole, definoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon, tetraconazole and imibenconazole.
  • the present method may further be employed by adding PVA to a liquid pesticidal composition which contains 1% to 60% of an azole fungicide selected from among a group consisting of epoxiconazole, tebuconazole, cyproconazole, prochloraz (Zn, Cu and Mn complexes), penconazole, definoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon, tetraconazole and imibenconazole; so that the pesticidal composition then contains 0.1% to 30% PVA.
  • an azole fungicide selected from among a group consisting of epoxiconazole, tebuconazole, cyproconazole, proch
  • Epoxiconazol (A.I.) 125 kg. (as 100%)
  • Solvesso 200 (Organic solvent) 1 400 kg.
  • Rhodopol MC thickener 2 0.75 kg. AF 10% emulsion J 1 kg. Water complete to 1000 liters
  • Rhodopol MC (thickener) 2.5 kg.
  • Triadiminol 150 kg. (as 100%) Poly vinyl alcohol (Crystal growth inhibitor) 12 kg.
  • the formation of crystals in spraying solutions is determined in various conditions in order to assure no crystal formation in various spraying conditions.
  • 10 liters of spraying solutions are prepared using hard water (CIPAC standard water D, 342 ppm) in 3 different concentrations: 0.5, 1, 2 times the recommended spraying concentration for each formulation.
  • Each sample is placed at 3 different temperatures: 2°C, 15°C and 30°C for 24 hours to allow crystal growth.
  • the solutions are sprayed using a personal spraying machine and using two filters ( ⁇ 8 gr. each): 100 and 50 mesh. After spraying the filters are dried and weighed. A weight difference of the filter before and after spraying of less than 0.05 gr. indicates essentially no crystal growth. Hence, there will not be filter blocking.

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

Abstract

La présente invention concerne un procédé d'inhibition de la croissance cristalline de fongicides azoles qui sont présents dans des compositions pesticides liquides. Ce procédé consiste à ajouter un alcool polyvinyle, comme inhibiteur de croissance cristalline, à des compositions fongicides contenant de l'azole liquide. L'invention concerne également une composition pesticide liquide contenant au moins un fongicide azole et un alcool polyvinyle (PVA) comme inhibiteur de croissance cristalline.
PCT/IL2001/000654 2001-07-17 2001-07-17 Composition pesticide liquide contenant un inhibiteur de croissance cristalline WO2003007716A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IL2001/000654 WO2003007716A1 (fr) 2001-07-17 2001-07-17 Composition pesticide liquide contenant un inhibiteur de croissance cristalline
ARP020102669A AR034800A1 (es) 2001-07-17 2002-07-16 Composicion plaguicida

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IL2001/000654 WO2003007716A1 (fr) 2001-07-17 2001-07-17 Composition pesticide liquide contenant un inhibiteur de croissance cristalline

Publications (1)

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WO2003007716A1 true WO2003007716A1 (fr) 2003-01-30

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PCT/IL2001/000654 WO2003007716A1 (fr) 2001-07-17 2001-07-17 Composition pesticide liquide contenant un inhibiteur de croissance cristalline

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WO (1) WO2003007716A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110053772A1 (en) * 2008-05-09 2011-03-03 Basf Se Process for the Production of Particles Comprising Active Agrochemical Ingredients in Amorphous Form
WO2011117868A1 (fr) * 2010-03-22 2011-09-29 Irvita Plant Protection N.V. Combinaison fongicide à effet synergique
CN101755808B (zh) * 2010-01-05 2012-11-07 陕西美邦农资贸易有限公司 一种含己唑醇与咪鲜胺锰盐的杀菌组合物
CN105875627A (zh) * 2014-10-17 2016-08-24 中国农科院植保所廊坊农药中试厂 一种咪鲜胺·氟环唑微乳剂的制备方法
CN107996590A (zh) * 2017-12-26 2018-05-08 广东广康生化科技股份有限公司 一种杀菌组合物及应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59112905A (ja) * 1982-12-20 1984-06-29 Sumitomo Chem Co Ltd 懸濁状殺菌組成物
US4475939A (en) * 1981-12-03 1984-10-09 Skw Trostberg Aktiengesellschaft Stabilized fertilizer solutions
JPS61126001A (ja) * 1984-11-22 1986-06-13 Kao Corp 水性懸濁状殺生剤組成物およびその製造法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4475939A (en) * 1981-12-03 1984-10-09 Skw Trostberg Aktiengesellschaft Stabilized fertilizer solutions
JPS59112905A (ja) * 1982-12-20 1984-06-29 Sumitomo Chem Co Ltd 懸濁状殺菌組成物
JPS61126001A (ja) * 1984-11-22 1986-06-13 Kao Corp 水性懸濁状殺生剤組成物およびその製造法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 198432, Derwent World Patents Index; Class A97, AN 1984-198101, XP002194281 *
PATENT ABSTRACTS OF JAPAN vol. 010, no. 314 (C - 380) 24 October 1986 (1986-10-24) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110053772A1 (en) * 2008-05-09 2011-03-03 Basf Se Process for the Production of Particles Comprising Active Agrochemical Ingredients in Amorphous Form
US8735321B2 (en) * 2008-05-09 2014-05-27 Basf Se Process for the production of particles comprising active agrochemical ingredients in amorphous form
CN101755808B (zh) * 2010-01-05 2012-11-07 陕西美邦农资贸易有限公司 一种含己唑醇与咪鲜胺锰盐的杀菌组合物
WO2011117868A1 (fr) * 2010-03-22 2011-09-29 Irvita Plant Protection N.V. Combinaison fongicide à effet synergique
CN105875627A (zh) * 2014-10-17 2016-08-24 中国农科院植保所廊坊农药中试厂 一种咪鲜胺·氟环唑微乳剂的制备方法
CN107996590A (zh) * 2017-12-26 2018-05-08 广东广康生化科技股份有限公司 一种杀菌组合物及应用

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Publication number Publication date
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