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WO2013075977A1 - Adjuvant contenant un ester d'acide gras et un agent tensioactif à base de silicone - Google Patents

Adjuvant contenant un ester d'acide gras et un agent tensioactif à base de silicone Download PDF

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Publication number
WO2013075977A1
WO2013075977A1 PCT/EP2012/072495 EP2012072495W WO2013075977A1 WO 2013075977 A1 WO2013075977 A1 WO 2013075977A1 EP 2012072495 W EP2012072495 W EP 2012072495W WO 2013075977 A1 WO2013075977 A1 WO 2013075977A1
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WO
WIPO (PCT)
Prior art keywords
adjuvant
pesticide
surfactant
aliphatic
methyl
Prior art date
Application number
PCT/EP2012/072495
Other languages
English (en)
Inventor
Marco-Antonio Tavares-Rodrigues
Luiz Antonio Martins DA SILVA
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to BR112014005010A priority Critical patent/BR112014005010A2/pt
Publication of WO2013075977A1 publication Critical patent/WO2013075977A1/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
    • 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
    • A01N25/02—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 liquids as carriers, diluents or solvents
    • 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
    • A01N25/30—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 characterised by the surfactants

Definitions

  • Adjuvant containing fatty acid ester and silicone surfactant Adjuvant containing fatty acid ester and silicone surfactant
  • the present invention relates to an adjuvant comprising (a) at least 20 wt% of a C1-C4 alkyl ester of an aliphatic C14-C22 carboxylic acid; and (b) at least 5 wt% of a silicone surfactant.
  • US 5,238,604 discloses a crop oil concentrate comprising an anionic surfactant, a hydrocarbon, and either a lower alkanol ester of a fatty acid or a fatty acid.
  • US 201 1/0177949 discloses an adjuvant comprising a lower alkanol ester of a fatty acid, an anionic surfactant, a fatty acid, an aromatic solvent, and optionally an antifoam.
  • an adjuvant comprising at least 20 wt% of a C1-C4 alkyl ester of an aliphatic C14-C22 carboxylic acid; and at least 5 wt% of a silicone surfactant.
  • Adjuvants may be described as compositions, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of a pesticide on the target.
  • the adjuvant is a liquid.
  • the aliphatic C14-C22 carboxylic acid unit of the C1-C4 alkyl ester of an aliphatic C14-C22 carbox- ylic acid may be linear or branched, saturated or unsaturated.
  • the carboxylic acid unit contains 14 to 18 carbon atoms.
  • the C1-C4 alkyl ester unit of the C1-C4 alkyl ester of an aliphatic C14-C22 carboxylic may be selected from methyl, ethyl, propyl, or butyl, wherein, methyl and/or ethyl are preferred, and wherein methyl is especially preferred.
  • the Ci- C 4 alkyl ester of an aliphatic C14-C22 carboxylic acid contains preferably a C1-C2 alkyl ester of an aliphatic C14-C18 carboxylic acid.
  • Ci-C4-Alkyl esters of aliphatic Ci4-C22-carboxylic acids which have the inventive and preferred features are commercially available, for example under the name Edenor® ME Ti 05 (or Synative® ES ME Ti 05) from Cognis Germany.
  • the adjuvant comprises at least 20 wt%, preferably at least 24 wt%, and in particular at least 27 wt%, of the C1-C4 alkyl ester of an aliphatic C14-C22 carboxylic acid.
  • the adjuvant may comprise up to 95 wt%, preferably up to 85 wt%, and in particular up to 80 wt% of the C1-C4 alkyl ester of an aliphatic C14-C22 carboxylic acid.
  • Silicone surfactants are a known class of surfactants, which is for example reviewed by
  • silicone surfactants are free of ionic groups.
  • the silicone surfactants are usually derived from silicones.
  • Silicones also termed polyorga- nosiloxanes
  • silicones are polymers, in which silicon atoms are linked via oxygen atoms, each silicon atom bearing one or several organic groups. They are also known as silicones and reviewed by Moretto et al., Ullmann's Encyclopedia of Industrial Chemistry, 2000, Keyword "Silicones”. Silicone surfactants are commercially available, e.g. under the brand names Silwet® from Mo- mentive, Sylgard® from Dow Corning, or Break-Thru® from Evonik.
  • the organo groups of the polyorganosiloxane comprise alkyl, aryl and/or polymeric groups.
  • the polyorganosiloxane may be linear, cyclic (like trisiloxanes), branched or crosslinked.
  • the organo groups of the polyorganosiloxane comprise polymeric groups in addition to alkyl and/or aryl groups.
  • alkyl groups are C1-C12 alkyl, preferably methyl.
  • aryl groups are phenyl or substituted phenyl groups, preferably phenyl.
  • Pre- ferred polymeric groups are polyether. Such compounds are also known as polyorganosiloxane- polyether.
  • the silicone surfactant comprises a polyorganosiloxane-polyether.
  • the polyether contains poly(ethylene oxide), poly(propylene oxide), or poly(ethylene oxide - co - pro- pylene oxide), wherein the latter may be a statistical or block copolymer of the alkylene oxides.
  • the polyorganosiloxane-polyether may be present as linear, branched or comb type polymers.
  • the polymers may have a Si-O-C as well as Si-C linkages between the polysiloxane and the polyether segment.
  • polyorganosiloxane-polyether examples include Dow Corning® types Q4-3667 (ABA block polymer), 5103 Surfactant (graft polymer), Q2-521 1 Super- wetting Agent (trisiloxane), or from Evonik Break-thru® S 240 (trisiloxane), or Break-thru® OE (graft polymer).
  • the adjuvant comprises at least 5 wt%, preferably at least 8 wt%, and in particular at least 12 wt%, of the silicone surfactant (e.g. a polyorganosiloxane-polyether).
  • the adjuvant may comprise up to 60 wt%, preferably up to 40 wt%, and in particular up to 20 wt% of the silicone surfactant.
  • the adjuvant may further comprise an anionic surfactant.
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • Preferred anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, and mixtures thereof.
  • sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • an anionic surfactants comprises a silicone residue, it is not considered a anionic surfactant, but rather a silicone surfactant.
  • the adjuvant may comprise at least 0,5 wt%, preferably at least 1 ,0 wt%, and in particular at least 1 ,5 wt%, of the anionic surfactant.
  • the adjuvant may comprise up to 15 wt%, preferably up to 8 wt%, and in particular up to 5 wt% of the anionic surfactant.
  • the adjuvant may further comprise a nonionic surfactant.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as al- cohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • the nonionic surfactant contains at least one (preferably at least two) alkoxylate.
  • Nonionic surfactants which comprises a silicone residue are not considered a nonionic surfactant, but rather a silicone surfactant.
  • the adjuvant may comprise at least 0,5 wt%, preferably at least 1 ,0 wt%, and in particular at least 2,0 wt%, of the nonionic surfactant.
  • the adjuvant may comprise up to 25 wt%, preferably up to 15 wt%, and in particular up to 10 wt% of the nonionic surfactant.
  • the adjuvant may further comprise a hydrocarbon oil. Suitable hydrocarbon oils contain aliphatic, cycloaliphatic and aromatic hydrocarbons, e. g.
  • toluene paraffin, tetrahydronaphthalene, alkylated naphthalenes.
  • mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil.
  • alkyl-substituted aromatics such as toluene, the xylenes, ethylbenzenes and benzenes with relatively long-chain alkyl radicals, e.g. Cg-C-io-dialkyl- and trialkylbenzenes (e.g. available under the name Solvesso® 100 from Exxon Mobile Europe or Aromatic 100 from Exxon Mobile USA), Cio-Cn-alkylbenzenes (e.g.
  • the hydrocarbon oil contains at least 50 wt%, more preferably at least 85 wt%, and in particular at least 95 wt% aliphatic and/or cycloaliphatic hydrocarbons.
  • the hydrocarbon oil contains up to 10 wt%, preferably up to 5 wt%, and in particular up to 3 wt% aromatic hydrocarbons.
  • the adjuvant contains up to 5 wt%, preferably up to 2,5 wt%, and in particular up to 1 ,5 wt% aromatic hydrocarbons.
  • the adjuvant may comprise up to 75 wt%, preferably up to 65 wt%, and in particular up to 55 wt% of the hydrocarbon oil. In another preferred form, the adjuvant comprises at least 20 wt%, preferably at least 30 wt%, and in particular at least 40 wt%, of the hydrocarbon oil. In another preferred form, the adjuvant comprises up to 10 wt%, preferably up to 5 wt%, and in particular up to 1 wt% of the hydrocarbon oil.
  • the adjuvant may comprise further auxiliaries, such as solvents, liquid carriers, surfactants, dispersants, emulsifiers, wetters, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, bactericides, anti-freezing agents, colorants.
  • auxiliaries such as solvents, liquid carriers, surfactants, dispersants, emulsifiers, wetters, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, bactericides, anti-freezing agents, colorants.
  • Suitable sol- vents and liquid carriers are water and organic solvents, such alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbon
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazoli- nones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable colorants e.g.
  • the adjuvant may comprise up to 20 wt%, preferably up to 10 wt%, and in particular up to 5 wt% of the auxiliaries.
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the adjuvant comprises
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the anionic surfactant e.g. an alkali, alkaline earth or ammonium salt of a sulfonate, sulfate, or phosphate.
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the anionic surfactant e.g. an alkali, alkaline earth or ammonium salt of a sulfonate, sulfate, or phosphate
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • hydrocarbon oil which preferably contains at least 50 wt% aliphatic and/or cycloaliphatic hydrocarbons
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the anionic surfactant e.g. an alkali, alkaline earth or ammonium salt of a sulfonate, sulfate, or phosphate.
  • the adjuvant comprises
  • silicone surfactant e.g. a polyorganosiloxane-polyether
  • the anionic surfactant e.g. an alkali, alkaline earth or ammonium salt of a sulfonate, sulfate, or phosphate
  • nonionic surfactant e.g. an alkoxylate
  • the invention further relates to a method for preparing the adjuvant according to the invention by mixing the C1-C4 alkyl ester of an aliphatic C14-C22 carboxylic acid, the silicone surfactant, and optionally the anionic surfactant, the nonionic surfactant, and/or the hydrocarbon oil.
  • the mixing may be done by any suitable means to obtain a homogeneous mixture.
  • the mixing may be done at room temperature or elevated temperatures. Heating and cooling system can be eventually necessary to melt or/and reduce the viscosity of any raw material.
  • the adjuvant is mixed in a blending vessel suitable for liquid mixing.
  • the adjuvant may be mixed by adding the C1-C4 alkyl ester of an aliphatic C14-C22 carboxylic acid to the hydrocarbon oil (if present), then the silicone surfactant is added, followed by the nonionic surfactant (if present) and subsequently the anionic surfactant (if present).
  • the invention further relates to an agrochemical composition comprising a pesticide and the adjuvant according to the invention.
  • pesticide refers to at least one active substance selected from the group of the fungicides, insecticides, nematicides, herbicides, safeners and/or growth regulators.
  • Preferred pesticides are fungicides, insecticides, herbicides and growth regulators.
  • Especially preferred pesticides are herbicides.
  • Mixtures of pesticides of two or more of the abovementioned classes may also be used.
  • the skilled worker is familiar with such pesticides, which can be found, for exam- pie, in the Pesticide Manual, 15th Ed. (2009), The British Crop Protection Council, London.
  • the following list of pesticides is intended to illustrate the possible pesticide but does not limit them:
  • Inhibitors of complex III at Q 0 site e.g. strobilurins: azoxystrobin, coumethoxystrobin,
  • coumoxystrobin dimoxystrobin, enestroburin, fenaminstrobin, fenoxy- strobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-[2-(2,5- dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-di- chlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl- acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone;
  • - inhibitors of complex II e. g. carboxamides: benodanil, bixafen, boscalid, carboxin, fen- furam, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(2- (1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;
  • respiration inhibitors e.g. complex I, uncouplers: diflumetorim, (5,8-difluoroquinazolin- 4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine; nitrophenyl deri- vates: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin; and silthi- ofam;
  • complex I uncouplers
  • DMI fungicides triazoles: azaconazole, bitertanol, bromucona- zole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbu- conazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triti- conazole, uniconazole; imidazoles: imazalil, pefurazoate, prochloraz, triflum
  • Delta14-reductase inhibitors aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
  • phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl; - others: hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p- tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuber- idazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7-(4-methyl- piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine
  • cell division inhibitors diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, pyriofenone;
  • - methionine synthesis inhibitors anilino-pyrimidines: cyprodinil, mepanipyrim, pyrimethanil;
  • blasticidin-S blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
  • MAP / histidine kinase inhibitors fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
  • - Phospholipid biosynthesis inhibitors edifenphos, iprobenfos, pyrazophos, isoprothiolane;
  • lipid peroxidation dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
  • phospholipid biosynthesis and cell wall deposition dimethomorph, flumorph, mandipropa- mid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1 -(1 -(4-cyano-phenyl)- ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
  • organochlorine compounds e.g. phthalimides, sulfamides, chloronitriles: anilazine, chloro- thalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachloroben- zene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N- ethyl-4-methyl-benzenesulfonamide;
  • organochlorine compounds e.g. phthalimides, sulfamides, chloronitriles: anilazine, chloro- thalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachloroben- zene, pentachlorphenole and its salts, phthalide, toly
  • guanidine dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon;
  • glucan synthesis validamycin, polyoxin B; melanin synthesis inhibitors: pyroqui- lon, tricyclazole, carpropamid, dicyclomet, fenoxanil;
  • Antifungal biocontrol agents plant bioactivators: Ampelomyces quisqualis (e.g. AQ 10 ® from Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (e.g. AFLAGUARD ® from Syngenta, CH), Aureobasidium pullulans (e.g. BOTECTOR ® from bio-ferm GmbH, Germany), Bacillus pumilus (e.g. NRRL Accession No.
  • Ampelomyces quisqualis e.g. AQ 10 ® from Intrachem Bio GmbH & Co. KG, Germany
  • Aspergillus flavus e.g. AFLAGUARD ® from Syngenta, CH
  • Aureobasidium pullulans e.g. BOTECTOR ® from bio-ferm GmbH, Germany
  • Bacillus pumilus e.g. NRRL Accession No.
  • Bacillus subtilis e.g. isolate NRRL-Nr. B-21661 in RHAPSO- DY ® , SERENADE ® MAX and SERENADE ® ASO from AgraQuest Inc., USA
  • Bacillus subtilis var. amyloliquefaciens FZB24 e.g. TAEGRO ® from Novozyme Biologicals, Inc., USA
  • Candida oleophila I-82 e.g. ASPIRE ® from Ecogen Inc., USA
  • Candida saitoana e.g.
  • BIO- CURE ® in mixture with lysozyme
  • BIOCOAT ® from Micro Flo Company, USA (BASF SE) and Arysta
  • Chitosan e.g. ARMOUR-ZEN from BotriZen Ltd., NZ
  • Clonostachys rosea f. catenulata also named Gliocladium catenulatum (e.g. isolate J 1446: PRESTOP ® from Verdera, Finland), Coniothyrium minitans (e.g. CONTANS ® from Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM, France), Cryptococcus albi- dus (e.g.
  • YIELD PLUS ® from Anchor Bio-Technologies, South Africa Fusarium oxysporum (e.g. BIOFOX ® from S.I.A.P.A., Italy, FUSACLEAN ® from Natural Plant Protection, France), Metschnikowia fructicola (e.g. SHEMER ® from Agrogreen, Israel), Microdochium dimerum (e.g. ANTIBOT ® from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP ® from Verdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX ® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (e.g.
  • PLANTSHIELD ® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO ® from Mycontrol Ltd., Israel), T. harzianum J-39 (e.g. TRICHODEX ® and TRICHO- DERMA 2000 ® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. REMEDIER ® WP from Isagro Ricerca, Italy), T. polysporum and T. harzianum (e.g.
  • T. stromaticum e.g. TRICO- VAB ® from C.E.P.L.A.C., Brazil
  • T. virens GL-21 e.g. SOILGARD ® from Certis LLC, USA
  • T. viride e.g. TRIECO ® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE ® F from T. Stanes & Co. Ltd., Indien
  • T. v/ ' r/ ' c/e TV1 e.g. T. viride TV1 from Agribiotec srl, Italy
  • Ulo- cladium oudemansii ⁇ RU3 e.g. BOTRY-ZEN ® from Botry-Zen Ltd, NZ
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6- dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione- calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
  • acetochlor alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefe- nacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • EPTC esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thio- bencarb, triallate;
  • acifluorfen acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, ox- yfluorfen;
  • - hydroxybenzonitriles bomoxynil, dichlobenil, ioxynil; - imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
  • - phenoxy acetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlor- prop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
  • - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
  • - sulfonyl ureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfu- ron, triflusulfuron, trito
  • - triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
  • ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
  • acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrim- isulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyri- fos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethi- on, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phentho- ate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
  • - carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosul- fan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodi- carb, triazamate;
  • - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
  • - insect growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cy- ramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juve- noids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
  • - nicotinic receptor agonists/antagonists compounds clothianidin, dinotefuran, flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -2-chloro-thiazol-5- ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
  • - GABA antagonist compounds endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole,
  • - macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
  • oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • cryomazine cryomazine
  • the agrochemical composition comprises a pesticidal effective amount of the pesticide.
  • a pesticidal effective amount of the pesticide can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific pesticide used.
  • compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • suspensions e.g. SC, OD, FS
  • emulsifiable concentrates e.g. EC
  • emulsions e.g. EW, EO, ES, ME
  • capsules e.g. CS, ZC
  • pastes e.g. WP, SP, WS, DP, DS
  • pressings e.g. BR, TB, DT
  • granules e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • the agrochemical composition may comprise 0,05 to 10 wt%, preferably 0,1 to 5 wt% of the adjuvant.
  • the agrochemical compositions preferably comprises a formulation auxiliary.
  • suitable formulation auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dis- persants, emulsifiers, wetters, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutch- eon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • composition types and their preparation are:
  • a pesticide and 5-15 wt% wetting agent e.g. alcohol alkoxylates
  • a water-soluble solvent e.g. alcohols
  • a pesticide and 1 -10 wt% dispersant e. g. polyvinylpyrrolidone
  • a dispersant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aro- matic hydrocarbon
  • This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • a pesticide In an agitated ball mill, 20-60 wt% of a pesticide are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1 -2 wt% thickener e.g. xanthan gum
  • 50-80 wt% of a pesticide are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water- dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 50-80 wt% of a pesticide are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • 1 -5 wt% dispersants e.g. sodium lignosulfonate
  • 1 wt% wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a pesticide In an agitated ball mill, 5-25 wt% of a pesticide are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance,
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. carboxymethylcellulose
  • 5-20 wt% of a pesticide are added to 5-30 wt% organic solvent blend (e.g. fatty acid dime- thylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and ar- ylphenol ethoxylate), and water up to 100 %.
  • organic solvent blend e.g. fatty acid dime- thylamide and cyclohexanone
  • surfactant blend e.g. alkohol ethoxylate and ar- ylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
  • methylmethacrylate, methacrylic acid and a di- or triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e.g. polyvinyl alcohol
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylme- thene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a polyamine e.g. hexamethylenediamine
  • the monomers amount to 1 -10 wt%.
  • Dustable powders (DP, DS)
  • 1 -10 wt% of a pesticide are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • 0.5-30 wt% of a pesticide is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.
  • the user applies the agrochemical composition according to the invention usually from a pre- dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • the agrochemical composition is a ready-to-use spray liquor, which may contain from 0,01 to 1 wt%, preferably from 0,05 to 0,7 wt%, and in particular from 0,2 to 0,5 wt% of the adjuvant.
  • individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the agrochemical composition accord- ing to the invention or partially premixed components e. g. components comprising the pesticide and components comprising the adjuvant may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the agrochemical composition according to the invention or partially premixed components e. g. components comprising the pesticide and components comprising the adjuvant, can be applied jointly (e.g. after tank mix) or consecutively.
  • the invention further relates to a method for controlling phytopathogenic fungi and/or undesired plant growth and/or undesired attack by insects or mites and/or for regulating the growth of plants, where the adjuvant according to the invention and a pesticide is allowed to act together or separately, at the same time or in succession, on the particular pests, their habitat or the plants to be protected from the particular pest, the soil and/or on undesired plants and/or the useful plants and/or their habitat.
  • the invention further relates to an use of the adjuvant according to the invention for increasing the efficacy of a pesticide.
  • the present invention offers various advantages: the adjuvant has a high efficacy; the adjuvant reduces the wind drift for spray applications; the adjuvant reduces the evaporation of pesticide; the adjuvant allows a better distribution of pesticides on leaves (e.g. higher spreading), and/or in leaves (e.g. higher uptake); aromatic hydrocarbons may be avoided thus reducing the toxicology and/or the phytotoxicity of the adjuvant; the adjuvant also provides water and moisture reten- tion what consequently impacts in better drought tolerance.
  • Abacus® HC from BASF SE was an aqueous suspension concentrate, which contained 22,9 % pyraclostrobin and 14,4 % epoxiconazol.
  • the liquid Adjuvant C1 contained 90 wt% of a mixed methyl and ethyl esters of oleic, palmitoleic, linoleic or miristoleic acids, 3 wt% dodecybenzene sulfonate calcium salt, and 3 wt% ethoxylated aliphatic alcohol (hydroxy number 140-155 mg KOH/g).
  • the mixed methyl and ethyl esters of oleic, palmitoleic, linoleic or miristoleic acids was charged, and then the ethoxylated aliphatic alcohol, and the dodecybenzene sulfonate was added.
  • the liquid Adjuvant C2 contained 38 wt% of a methyl esters of oleic and palmitoleic acids, 23 wt% phosphate ester of polyether (Mw about 800 Da), 35 wt% aromatic hydrocarbons
  • the liquid Adjuvant A contained 76 wt% of a mixed methyl and ethyl esters of oleic, palmitoleic , linoleic or miristoleic acids, 15 wt% polyether-trisiloxane (liquid, surface tension about 21 -24 mN/m at 20 °C, 0,1 %), 3 wt% dodecybenzene sulfonate calcium salt, 3 wt% glycerol monoole- ate, and 3 wt% ethoxylated aliphatic alcohol (hydroxy number 140-155 mg KOH/g).
  • the polyether-trisiloxane was added and blended until a homogeneous mixture was obtained.
  • the Adjuvant A was a clear yellowish liquid, which was stable to light, air, pH, and temperature.
  • the Adjuvant A was emulsifiable in water and miscible in organic solvents. Flash point was about 180 °C.
  • the liquid Adjuvant B contained 31 wt% of a mixed methyl and ethyl esters of oleic, palmitoleic , linoleic or miristoleic acids, 15 wt% polyether-trisiloxane (liquid, surface tension about 21 -24 mN/m at 20 °C, 0,1 %), 2 wt% dodecybenzene sulfonate calcium salt, 3 wt% glycerol monooleate, and 1 wt% ethoxylated aliphatic alcohol (hydroxy number 140-155 mg KOH/g), and 46 wt% hydrocarbon oil (containing 66-73 wt% paraffins, 27-34 wt% cycloparaffins, and less than 3 wt% aromatic hyrocarbons; boiling point >220 °C at 10 mm Hg (50 %, ASTM D 1 160).
  • the hydrocarbon oil was charged, followed by the mixed methyl and ethyl esters of oleic, palmitoleic , linoleic or miristoleic acids, the polyether-trisiloxane, and finally a premix of the ethoxylated aliphatic alcohol, the molten glycerol monooleate and the dodecybenzene sulfonate.
  • the compo- nents were blended until a homogeneous mixture was obtained.
  • the Adjuvant B was a clear yellowish liquid, which was stable to light, air, pH, and temperature.
  • the Adjuvant B was emulsifiable in water and miscible in organic solvents. Flash point was about 180 °C.
  • a mixture of Abacus® HC and the respective adjuvant were used at an application rate of 100 L/ha (0,25 % Abacus + 0,3 % adjuvant).
  • the contact angle on wheat leaves was determined after 1 min.

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

Abstract

La présente invention concerne un adjuvant comprenant (a) au moins 20 % en poids d'un ester C1-C4-alkylique d'un acide C14-C22-carboxylique aliphatique ; et (b) au moins 5 % en poids d'un agent tensioactif à base de silicone. En outre, l'invention concerne un procédé de préparation dudit adjuvant ; une composition agrochimique comprenant un pesticide et ledit adjuvant ; un procédé pour lutter contre des champignons phytopathogènes et/ou une croissance de plantes non souhaitées et/ou une attaque non souhaitée par des insectes ou des acariens et/ou pour réguler la croissance des plantes, ledit adjuvant et un pesticide pouvant agir ensemble ou séparément, au même moment ou successivement, sur les organismes nuisibles particuliers, leur habitat ou les plantes à protéger des organismes nuisibles particuliers, le sol et/ou sur des plantes non souhaitées et/ou les plantes utiles et/ou leur habitat ; et enfin une utilisation dudit adjuvant pour augmenter l'efficacité d'un pesticide.
PCT/EP2012/072495 2011-11-23 2012-11-13 Adjuvant contenant un ester d'acide gras et un agent tensioactif à base de silicone WO2013075977A1 (fr)

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Cited By (4)

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WO2015103192A1 (fr) * 2013-12-30 2015-07-09 Rhodia Operations Compositions pesticides agricoles
CN110461154A (zh) * 2017-03-23 2019-11-15 花王株式会社 农药用效力增强剂组合物
EP3636733A1 (fr) 2018-10-12 2020-04-15 Wacker Metroark Chemicals Pvt. Ltd. Composition de silicone et son application comme additif dans la composition d'un détergent pour améliorer la production de mousse et l'effet de nettoyage
CN115397239A (zh) * 2020-04-10 2022-11-25 花王株式会社 植物处理剂用蒸发抑制剂

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015103192A1 (fr) * 2013-12-30 2015-07-09 Rhodia Operations Compositions pesticides agricoles
CN110461154A (zh) * 2017-03-23 2019-11-15 花王株式会社 农药用效力增强剂组合物
CN110461154B (zh) * 2017-03-23 2021-11-09 花王株式会社 农药用效力增强剂组合物
EP3636733A1 (fr) 2018-10-12 2020-04-15 Wacker Metroark Chemicals Pvt. Ltd. Composition de silicone et son application comme additif dans la composition d'un détergent pour améliorer la production de mousse et l'effet de nettoyage
WO2020074986A1 (fr) 2018-10-12 2020-04-16 Wacker Metroark Chemicals Pvt. Ltd. Composition de silicone et son application en tant qu'additif dans une composition de détergent pour améliorer le pouvoir moussant et l'effet de nettoyage
US11692154B2 (en) 2018-10-12 2023-07-04 Wacker Metroark Chemicals Pvt Ltd Dimethicone copolyol composition and its application as an additive in detergent composition to enhance foamability and cleaning effect
CN115397239A (zh) * 2020-04-10 2022-11-25 花王株式会社 植物处理剂用蒸发抑制剂
EP4133939A4 (fr) * 2020-04-10 2024-08-14 Kao Corporation Retardateur d'évaporation pour agent de traitement des plantes

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