WO2020121344A1 - Concentré émulsionnable contenant du fluindapyr et son utilisation comme fongicide dans des plantes cultivées - Google Patents

Concentré émulsionnable contenant du fluindapyr et son utilisation comme fongicide dans des plantes cultivées Download PDF

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Publication number
WO2020121344A1
WO2020121344A1 PCT/IT2018/000160 IT2018000160W WO2020121344A1 WO 2020121344 A1 WO2020121344 A1 WO 2020121344A1 IT 2018000160 W IT2018000160 W IT 2018000160W WO 2020121344 A1 WO2020121344 A1 WO 2020121344A1
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WO
WIPO (PCT)
Prior art keywords
emulsifiable concentrate
weight
acid
fluindapyr
concentrate according
Prior art date
Application number
PCT/IT2018/000160
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English (en)
Inventor
Elisa GALIMBERTI
Claudio DACARRO
Paolo Bellandi
Original Assignee
Isagro S.P.A.
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 Isagro S.P.A. filed Critical Isagro S.P.A.
Priority to PCT/IT2018/000160 priority Critical patent/WO2020121344A1/fr
Priority to ARP190103657A priority patent/AR117326A1/es
Publication of WO2020121344A1 publication Critical patent/WO2020121344A1/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
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to an emulsifiable concentrate containing fluindapyr and its use as a fungicide in crop plants.
  • Fluindapyr is a succinate dehydrogenase inhibitor (SDHI) , an enzyme linked to the inner mitochondrial membrane that participates in the cellular respiration process .
  • SDHI succinate dehydrogenase inhibitor
  • Inhibitors of this enzyme are used as fungicides in the agricultural field and are known for their high level of biological activity and broad spectrum of action.
  • fluindapyr belongs to the class of N-indanyl-pyrazolcarboxamides and is represented by the formula (I) , shown below:
  • formulations containing succinate dehydrogenase inhibitors are known in the art for use in the agrochemical field. Such formulations can be in the form of solid or liquid preparations, or in the form of solid suspensions in liquids.
  • the formulations In order to be correctly used, the formulations have to be able to solubilize or disperse, or they have to give rise to stable emulsions when diluted in specific volumes of water.
  • the formulations with the addition of water are in turn applied to crops or soils in which a crop is grown, before or after sowing or germination.
  • emulsifiable concentrates a specific type of liquid agronomic formulation wherein the active ingredient is dissolved in a solvent which is substantially immiscible with water with the addition of surfactants, such as emulsifiers, wetting agents, anti-foaming agents, antifreezes and biological activators, which make it more suitable for use in agriculture.
  • surfactants such as emulsifiers, wetting agents, anti-foaming agents, antifreezes and biological activators, which make it more suitable for use in agriculture.
  • the emulsifiable concentrate forms an oil-in-water emulsion.
  • patent application WO 2018/141575 describes an emulsifiable concentrate consisting of an agropharmaceutical , an amide solvent, a nonionic surfactant and a specific stabilizer, i.e. 1,2- cyclohexane dicarboxylic acid diisononyl ester.
  • WO 2012/69514 describes emulsifiable concentrates comprising an insoluble pesticide in water, a nonionic surfactant, an acrylate copolymer and at least one organic solvent, which may include among others 1,2- cyclohexane dicarboxylic acid diisononyl ester.
  • Emulsifiable concentrates have numerous advantages, such as excellent biological activity and high formulation stability in the absence of crystallization phenomena.
  • the Applicant has surprisingly found that the emulsifiable concentrates containing fluindapyr in combination with the aforementioned N,N- dimethylamide solvents have high stability even in the absence of the 1, 2 -cyclohexane dicarboxylic acid diisononyl stabilizing ester described in the prior art .
  • a first object of the present invention is an emulsifiable concentrate comprising: a) fluindapyr;
  • Fluindapyr is the ISO name of the molecule having chemical formula 3-difluoromethyl-N- (7-fluoro-l, 1, 3- trimethyl -4 - indanyl ) - 1 -methyl-4 -pyrazolcarboxamide .
  • the fluindapyr is present in the emulsifiable concentrate in an amount within the range from 0.5% to 40% by weight, more preferably from 5% to 20% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrate according to the present invention in addition to fluindapyr, may comprise at least one further active agrochemical ingredient, or a mixture of two or more further active agrochemical ingredients other than fluindapyr.
  • the active agrochemical ingredients are selected from: fungicides, insecticides, nematocides, herbicides, phytoprotectors and/or growth regulators. Fungicides are particularly preferred agrochemical compounds .
  • the additional active ingredients can be, for example, fungicides selected from the following classes of compounds :
  • active agrochemical ingredient or "agrochemical compound” is intended as an active substance which produces a protective effect against harmful organisms, a conservation effect and/or a control effect of a crop; the active agrochemical ingredient is selected, for example, from: fungicides, insecticides, nematocides, herbicides, phytoprotectors and/or growth regulators. Fungicides are particularly preferred agrochemical compounds .
  • fungicidal compounds belonging to the class of triazoles that can be present in the emulsifiable concentrate are: azaconazole, bitertanol, bromuconazole , cyproconazole , diphenoconazole , epoxiconazole , fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole , imazalil, ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole, myclobutanil , penconazole, propiconazole, prothioconazole, simeconazole , tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole .
  • the emulsifiable concentrate contains fluindapyr and prothioconazole as the only further active agrochemical ingredient other than fluindapyr .
  • the emulsifiable concentrate contains fluindapyr and at least prothioconazole as a further active agrochemical ingredient other than fluindapyr.
  • the emulsifiable concentrate contains fluindapyr and tetraconazole as the only further active agrochemical ingredient other than fluindapyr .
  • the emulsifiable concentrate contains fluindapyr and at least tetraconazole as a further active agrochemical ingredient other than fluindapyr .
  • fungicidal compounds belonging to the class of strobilurins that can be present in the emulsifiable concentrate are: azoxystrobin, dimoxystrobin, fluoxastrobine , kresoxim-methyl, methominostrobin, orysastrobine, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxostrobin, trifloxystrobin.
  • fungicidal compounds belonging to the class of amidines which can be present in the emulsifiable concentrate are: N-ethyl-N-methyl-N 1 -5 bromo-2-methyl -6- ⁇ [3-
  • fungicidal compounds belonging to the class of chloronitriles that can be present in the emulsifiable concentrate is chlorothalonil .
  • fungicidal compounds belonging to the class of picolinamides which can be present in the emulsifiable concentrate are fenpicoxamid and florylpicoxamid.
  • fungicidal compounds belonging to the class of salicylamides which can be present in the emulsifiable concentrate is 3-formylamino-2- [ (2-methyl- propanoyl-oxy) methoxy] -N- (3 , 3 , 5 , 5- tetramethylcyclohexyl) benzamide .
  • the emulsifiable concentrate contains one or more further active agrochemical ingredients other than fluindapyr
  • their total concentration is preferably in the range of 3% to 20% by weight, more preferably 4% to 16% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrate contains prothioconazole in a concentration in the range of 14% to 15% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrate contains fluindapyr in a concentration in the range of 14% to 15% by weight, and prothioconazole in a concentration of 14% to 15% by weight, preferably 14% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrate contains fluindapyr in a concentration in the range of 8% to 9% by weight, and prothioconazole in a concentration from 14% to 15% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrate contains tetraconazole in a concentration in the range of 10% to 11% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrate contains fluindapyr in a concentration in the range of 10% to 11% by weight, and tetraconazole in a concentration in the range of 10% to 11% by weight, with respect to the weight of said emulsifiable concentrate .
  • emulsifiable concentrates are prepared by dissolving the active agrochemical ingredient in a mixture of at least one solvent and at least one surfactant.
  • N,N- dimethylamide derivatives of fatty acids C 6 -Ci 6 are particularly suitable as solvents for the preparation of emulsifiable concentrates containing fluindapyr, as these solvents have a low eco-toxicological profile, as well as provide a very stable and pourable formulation, without crystallization phenomena.
  • the emulsifiable concentrates according to the invention are also sufficiently stable even in the absence of the stabilizer 1, 2-cyclohexane dicarboxylic acid diisononyl ester which, in some cases, may even reduce its stability.
  • the emulsifiable concentrates according to the invention do not contain stabilizers belonging to the dibasic acid ester family.
  • the hydrocarbon chain of the fatty acid is made up of a number of carbon atoms from 8 to 12 (C 8 -C 12) .
  • the fatty acid C 6 -C 16 is a mono- unsaturated carboxylic acid.
  • N, N-dimethylamides of fatty acids C 6 - Ci 6 solvents that can be used for the purposes of the present invention are: N, N-dimethyloctanamide, N,N- dimethyldecanamide, N,N-dimethyldodecanamide, N,N- dimethyldecenamide or mixtures thereof .
  • the solvent is N,N- dimethyldecanamide .
  • the above solvent (hereinafter also referred to as "primary solvent”) is preferably present in an amount in the range of 10% to 60% by weight, more preferably in the range of 15% to 50% by weight, with respect to the weight of said emulsifiable concentrate.
  • the primary solvent can also be used in mixtures with at least one second solvent (co-solvent) .
  • the co- solvent is selected from: glycerine, monopropylene glycol, alkyl esters Ci-C 4 of fatty acids C 12 -C 22 or water.
  • the alkyl ester is a methyl ester.
  • alkyl esters C 1 -C 4 of fatty acids C 12 - C22 that can be used as co- solvents for the purposes of the present invention are alkyl esters, in particular methyl esters, of the following fatty acids: oleic acid, linoleic acid, a-linolenic acid, palmitic acid, stearic acid, erucic acid, arachidic acid.
  • the ratio of the total weight of the at least one primary solvent and the total weight of the at least one co-solvent is preferably within the range from 1:4 to 4:1.
  • the co-solvent is present in the emulsifiable concentrate in an amount within the range of from 1% to 45% by weight, more preferably within the range of from 5% to 40% by weight, relative to the weight of said emulsifiable concentrate.
  • no co-solvent is present in the emulsifiable concentrate, but one or more primary solvents are present, more preferably only N, N-dimethyldecanamide .
  • the at least one nonionic surfactant used in the emulsifiable concentrate has the function of emulsifier (surfactant emulsifier) .
  • said nonionic surfactant is selected from: etho- propoxylated block copolymers, acrylic polymers, ethoxylated tristyrylphenols , etho-propoxylated tristyrilphenols , ethoxylated tristyrylphenol phospates (acid form) , ethoxylated tristyrylphenol sulphates (acid form) , alkyl polyglucosides , ethoxylated vegetable oil, ethoxylated sorbitan monolaurate ; ethoxylated fatty alcohols, modified polyether polysiloxanes and mixtures thereof.
  • the nonionic surfactant emulsifier is present in the emulsifiable concentrate in an overall amount within the range from 5% to 40% by weight, more preferably from 7% to 20% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrate in addition to the at least one nonionic surfactant, can comprise one or more additional surfactants other than nonionic surfactants, such as for example anionic surfactants .
  • said anionic surfactants are selected from: tristyrylphenol phosphate ethoxylates (salt form) , dodecyl benzene sulphonates, sulphosuccinates and mixtures thereof. More preferably said anionic surfactant is an alkaline or alkaline-earth salt of dodecyl benzene sulphonate .
  • the additional surfactants other than nonionic surfactants are present in the emulsifiable concentrate preferably in an overall amount comprised in the range from 1% to 15% by weight, more preferably in the range from 2% to 10% by weight, with respect to the weight of said emulsifiable concentrate.
  • the emulsifiable concentrates according to the present invention can also comprise further coformulating additives, such as anti-foaming agents.
  • further compounds can also be added to improve their biological activity, such as anti-drift agents, penetrating agents, wetting agents and spreaders .
  • the preparation of the emulsifiable concentrates according to the present invention can be carried out according to known methods, for example by mixing the components in the desired ratios, without particular limitations in the order in which the components are mixed.
  • the active ingredient fluindapyr in a first step can be dissolved in the primary solvent; in a second step, at least one nonionic surfactant is added to the solution obtained in the first step.
  • fluindapyr is added to the mixture of the primary solvent and the nonionic surfactant.
  • the emulsifiable concentrates according to the present invention exhibit a high level of fungicidal activity and do not show any substantial phytotoxicity towards the crops to which they are applied.
  • a further object of the present invention is the use of the above emulsifiable concentrates for the control of phytopathogenic fungi in a crop plant .
  • a further object of the present invention is a method for controlling phytopathogenic fungi in a crop plant which comprises applying at least one effective dose of one of the above described emulsifiable concentrates to a crop plant .
  • crops of interest are: fruit trees, vegetables and extensive crops, such as rice, wheat and soy.
  • emulsifiable concentrates according to the present invention can be applied, as such or in diluted form, on any part of the plant, for example on leaves, stems, branches and roots, or on the seeds themselves before sowing, or on the soil where the plant will grow.
  • the emulsifiable concentrates according to the present invention are preferably applied to a crop plant in diluted form with water to form an oil-in- water emulsion.
  • the emulsifiable concentrate according to the present invention can be used to prepare an oil- in water emulsion, combining said concentrate with water, optionally in the presence of other ingredients, such as wetting agents, emulsifying agents, etc..
  • the additional ingredients can also be present, or present only, in the water used to dilute the emulsifiable concentrate .
  • a further object of the present invention is therefore a process for preparing an agronomic formulation in the form of an oil-in-water emulsion comprising :
  • Water is added in the amount necessary to achieve the required oil-in-water emulsion volume.
  • the quantity of emulsifiable concentrate or the relative emulsion to be applied to a crop plant to obtain the desired agrochemical effect may vary depending on various factors such as, for example, the crop, climatic conditions, soil characteristics, the method of application.
  • Emulsifiable concentrates containing fluindapyr The emulsifiable concentrates n. ECl - ECU were prepared according to the present invention, having the compositions shown in Table 1 (concentrates containing fluindapyr as the only active agrochemical ingredient) and in Table 2 (concentrates containing fluindapyr in admixture with other active agrochemical ingredients) .
  • Rhodiasolv ADMA 810 mixture of N,N- dimethyloctanamide and N, N-dimethyldecanamide ;
  • Rhodiasolv ADMA 10 N, N-dimethyldecanamide ;
  • - Hallcomid 1025 N,N-dimethyl 9-decenamide
  • - Agnique AMD 12 N, N-dimethyldodecanamide ;
  • Soprophor TSP/724 etho-propoxylated tristyrylphenol
  • Antarox PLG/254 etho-propoxylated block copolymer
  • Rhodacal 60/BE benzene sulphonic acid calcium salt ;
  • Soprophor 796/P etho-propoxylated tristyrylphneol ;
  • the emulsifiable concentrates n. ECl - ECU were subjected to the accelerated stability test (according to Cipac MT 46.1) which aims at accelerating the ageing of the product through heating. This test allows to simulate the stability of a formulation after two years of storage at room temperature.
  • a certain amount of formulation for example 500 mL was placed in a hermetically sealed container and left in an oven at 54 °C for 14 days. After this time, the container was removed from the oven and left to return to room temperature. It was therefore verified that the formulation did not show any phase separation or other phenomena of physical instability, such as flocculation, aggregation or crystalline growth.
  • the chemical stability of the active agrochemical ingredient is also verified, as well as the quality of the emulsion subjected to accelerated stability tests, after dilution in water.
  • the plants were kept in an environment saturated with humidity and a temperature comprised between 18 and 24 °C for the incubation period of the fungus (1 day) .
  • the emulsifiable concentrate ECl exhibited excellent control of the disease. Furthermore, productivity at the time of collection was also evaluated.
  • Table 3 shows the results obtained by carrying out the test described with the above emulsifiable concentrate in comparison with a commercial product, PROLINE ® (emulsifiable concentrate containing prothioconazole 27.5% weight/weight and N, -dimethyldecanamide) :
  • the emulsifiable concentrate according to the invention effectively controlled the disease even at low doses, despite the high level of infection.
  • the application of the emulsifiable concentrate also allowed to increase the production of wheat by about a third compared to the commercial product.
  • both sides of the plants' leaves were sprayed with an aqueous suspension of spores of Septoria nodorum (1,000,000 spores/cc) .
  • the plants were kept in an environment saturated with humidity and a temperature comprised between 18 and 24 °C for the incubation period of the fungus (2 days) .
  • the emulsifiable concentrate EC7 exhibited excellent control of the disease.
  • Table 4 shows the results obtained by carrying out the test described with the above emulsifiable concentrate in comparison with the commercial product AVIATOR XPRO ® (emulsifiable concentrate containing bixafen 7.45% weight/weight , prothioconazole 14.90% w/w and N,N- dimethyldecanamide) .
  • the emulsifiable concentrate EC7 also demonstrated high efficacy against Septoria nodorum, providing control similar to that of the commercial standard for that disease.
  • emulsifiable concentrates n. EC2 and EC5 were subjected to a further stability test (according to Cipac MT 36) which aimed to evaluate the stability of an emulsion after 24 hours.
  • Some emulsifiable concentrates were also prepared for comparison according to that which is described in the patent application WO2018/141575 (REC1 - REC6 ) , which were subsequently subjected to the same stability test.
  • compositions of the prepared and tested emulsifiable concentrates are shown in Tables 5 and 6.
  • Nonionic surfactant used in the examples of
  • the emulsifiable concentrates were poured at a concentration of 5% v/v in standard D Cipac water (hardness 342 ppm), as per the test MT 36.
  • the following procedure was used: a 100ml graduated glass cylinder is filled with 95ml of standard Cipac D water, 5ml of EC formulate are added and the cylinder is closed with a glass stopper. The cylinder is inverted 30 times and left undisturbed at 30°C, observing the stability of the emulsion formed, after 30 minutes, 2 hours and 24 hours.
  • the observations regarding the stability of these emulsifiable concentrates after 30 minutes, 2 hours and 24 hours are reported in Tables 7 and 8.
  • stable means that no separation of oil or non-homogeneity is detected in the emulsion.
  • the emulsifiable concentrates EC2 and EC5 according to the invention are stable even after 24 hours, whereas the comparative ones are unstable already after 2 hours.
  • the results show that the 1,2-cyclohexane dicarboxylic acid diisononyl ester compound described in WO2018/141575 does not produce any stabilizing effect in the case of emulsifiable concentrates containing fluindapyr. On the contrary, with the other conditions remaining the same, it negatively affects stability (see REC3 , REC6) .

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

Abstract

La présente invention concerne un concentré émulsionnable comprenant : du fluindapyr, au moins un solvant N, N-diméthylamide d'un acide gras ayant de 6 à 16 atomes de carbone, au moins un tensioactif non ionique ; en l'absence de 1, 2-cyclohexane-acide dicarboxylique diisononyle ester. La présente invention concerne également l'utilisation du concentré émulsionnable ci-dessus comme fongicide dans des cultures agricoles.
PCT/IT2018/000160 2018-12-14 2018-12-14 Concentré émulsionnable contenant du fluindapyr et son utilisation comme fongicide dans des plantes cultivées WO2020121344A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IT2018/000160 WO2020121344A1 (fr) 2018-12-14 2018-12-14 Concentré émulsionnable contenant du fluindapyr et son utilisation comme fongicide dans des plantes cultivées
ARP190103657A AR117326A1 (es) 2018-12-14 2019-12-13 Concentrado emulsificable que contiene fluindapir y su uso como fungicida en plantas de cultivo

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Application Number Priority Date Filing Date Title
PCT/IT2018/000160 WO2020121344A1 (fr) 2018-12-14 2018-12-14 Concentré émulsionnable contenant du fluindapyr et son utilisation comme fongicide dans des plantes cultivées

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WO2020121344A1 true WO2020121344A1 (fr) 2020-06-18

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114403136A (zh) * 2021-11-18 2022-04-29 祺农化工科技(上海)有限公司 一种以n,n-二甲基己酰胺为主的混合溶剂及制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018141575A1 (fr) * 2017-02-01 2018-08-09 Basf Se Concentré émulsifiable
WO2018204437A1 (fr) * 2017-05-02 2018-11-08 Dow Agrosciences Llc Mélanges synergiques pour la lutte contre des champignons dans des légumes
EP3412150A1 (fr) * 2017-06-06 2018-12-12 Basf Se Mélanges de meptyldinocap avec fongicides sdhi

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018141575A1 (fr) * 2017-02-01 2018-08-09 Basf Se Concentré émulsifiable
WO2018204437A1 (fr) * 2017-05-02 2018-11-08 Dow Agrosciences Llc Mélanges synergiques pour la lutte contre des champignons dans des légumes
EP3412150A1 (fr) * 2017-06-06 2018-12-12 Basf Se Mélanges de meptyldinocap avec fongicides sdhi

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114403136A (zh) * 2021-11-18 2022-04-29 祺农化工科技(上海)有限公司 一种以n,n-二甲基己酰胺为主的混合溶剂及制备方法和应用
CN114403136B (zh) * 2021-11-18 2023-03-14 祺农化工科技(上海)有限公司 一种以n,n-二甲基己酰胺为主的混合溶剂及制备方法和应用

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