WO2013136275A1 - Compositions synergiques à activité fongicide et leur utilisation - Google Patents

Compositions synergiques à activité fongicide et leur utilisation Download PDF

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Publication number
WO2013136275A1
WO2013136275A1 PCT/IB2013/051978 IB2013051978W WO2013136275A1 WO 2013136275 A1 WO2013136275 A1 WO 2013136275A1 IB 2013051978 W IB2013051978 W IB 2013051978W WO 2013136275 A1 WO2013136275 A1 WO 2013136275A1
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compound
spp
methyl
compositions according
azoxystrobin
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PCT/IB2013/051978
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English (en)
Inventor
Matteo Santino Vazzola
Franco Pellacini
Original Assignee
Isagro S.P.A.
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Application filed by Isagro S.P.A. filed Critical Isagro S.P.A.
Publication of WO2013136275A1 publication Critical patent/WO2013136275A1/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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines

Definitions

  • the present invention relates to compositions of products having a fungicidal activity and their use for the control of phytopathogenic fungi of important agricultural crops.
  • the object of the present invention relates to new synergistic fungicidal compositions containing phenylamidines substituted by specific groups and one or more products having a fungicidal activity.
  • Phenylamidines having a fungicidal activity are described in international patent applications WO 2000/46184, WO 2003/093224, WO 2007/031508, WO 2007/031512, WO 2007/031513, WO 2007/031523, WO 2007/031524, WO 2008/110279 and in WO 2012/025450.
  • a first object of the present invention therefore relates to synergistic fungicidal compositions comprising :
  • - R represents a C 2 -C 6 haloalkyl
  • - Y represents an oxygen atom or a sulfur atom
  • Rx represents a halogen atom, a C 1 -C6 alkyl, a C 1 -C6 haloalkyl
  • Z represents an oxygen atom, a sulfur atom, a SO group, a SO2 group
  • Ri represents a C 2 -C 6 alkyl
  • R2 represents a C 1 -C6 alkyl
  • R3 and R 4 equal to or different from each other, represent a hydrogen atom, a halogen atom, a C 1 -C6 alkyl, a C 1 -C6 alkoxyl, a C 1 -C6 haloalkoxyl, a CF 3 group, a CF 2 H group, a CFH 2 group, a cyano group; [B] at least one compound having a fungicidal activity selected from one of the following groups: a) azoles;
  • SAR systemic acquired resistance inductors
  • Preferred compounds having general formula (I) in the compositions object of the present invention are: compound 1: N-ethyl-N-methyl-N '- ⁇ 4- [ 3- ( 1 , 1 , 2 , 2-tetra- fluoroethoxy) -phenylthio ] -2, 5-xylyl ⁇ formamidine ;
  • compound 4 N-ethyl-N-methyl-N '- ⁇ 4- [4-chloro-3- (1,1,2,2- tetrafluoroethoxy) phenylthio ] -2, 5-xylyl ⁇ formamidine ;
  • compound 6 N-ethyl-N-methyl-N '- ⁇ 4- [4-fluoro-3- (1,1,2,2- tetrafluoroethoxy) phenylthio ] -2, 5-xylyl ⁇ formamidine .
  • compositions can be selected with the international ISO name; the chemical structures, physico-chemical data and biological characteristics of these compounds are mainly indicated in "Pesticide Manual", C.D.S. Tomlin, 15 a Edition, 2009, British Crop Production Council Editor.
  • Preferred components [B] of the compositions object of the present invention are:
  • azoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxyconazole, fen- buconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, ipconazole, metconazole, myclobutanil , penconazole, propiconazole, prochloraz, prothioconazole, simeconazole, tebuconazole, tetra- conazole, triadimefon, triadimenol, triflumizole, triticonazole;
  • amino-derivatives aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine , spiroxamine, tridemorph;
  • succinate-dehydrogenase inhibitors bixafen, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, oxycarboxin, penflufen, penthiopyrad, sedaxane, thifluzamide;
  • strobilurins azoxystrobin, dimoxystrobin, fluoxa- strobin, kresoxim-methyl , metominostrobin, orysa- strobin, picoxystrobin, pyraclostrobin, pyrameto- strobin, pyraoxostrobin, trifloxystrobin;
  • e) specific antioidic compounds cyflufenamid, flutianil, metrafenone, proquinazid, pyriofenone, quinoxyfen ;
  • aniline-pyrimidines pyrimethanil , mepanipyrim, cyprodinil ;
  • benzimidazoles and analogues carbendazim, benomyl, thiabendazole, thiophanate-methyl ;
  • dicarboxyimides iprodione, procymidone ;
  • SAR inductors acibenzolar, probenazole, isotianil, tiadinil;
  • phenylpyrroles fenpiclonil, fludioxonil ;
  • acylalanines benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M;
  • antiperonosporic compunds ametoctradin, amisulbrom, benthiavalicarb, cyazofamid, cymoxanil, dimethomorph, ethaboxam, famoxadone, fenamidone, flumetover, flumorph, fluopicolide, iprovalicarb, mandipropamid, valifenalate ;
  • dithiocarbamates maneb, mancozeb, propineb, zineb.
  • cyproconazole difenoconazole, epoxyconazole, flutriafol, penconazole, prochloraz, prothioconazole, tebuconazole, tetraconazole ;
  • azoxystrobin fluoxastrobin, kresoxim-methyl , picoxystrobin, pyraclostrobin, trifloxystrobin;
  • compositions consisting of:
  • the compounds having general formula (I) wherein Z represents a sulfur atom are prepared as described in WO 2012/025450; products wherein Z represents SO and SO 2 by oxidation of the S atom with an oxidizing agent, such as, for example, metha-chloroperbenzoic acid, can be produced from these compounds; compounds wherein Z represents an oxygen atom, can be prepared analogously to the methods described in WO 2012/025450 for 4- phenylthio-phenylamidines , starting from the corresponding 4-phenoxy derivatives.
  • an oxidizing agent such as, for example, metha-chloroperbenzoic acid
  • the fungicidal compositions object of the present invention have a strong synergistic effect, which can be evaluated by applying the Colby formula ("Weeds", 1967, page 15, pages 20- 22) :
  • E t E A +E B -(E A -E B /100) wherein E t is the expected efficacy percentage for the composition containing compounds A and B at dosages d A +d B , E A is the efficacy percentage observed for component A at the dosage d A , E B is the efficacy percentage observed for component B at the dosage d B .
  • E t ⁇ ⁇ + ⁇ ⁇ 1 + ⁇ ⁇ 2 -( ⁇ ⁇ ⁇ ⁇ 1 + ⁇ ⁇ ⁇ ⁇ 2 + ⁇ ⁇ 1 ⁇ ⁇ 2 /100) + ( ⁇ ⁇ ⁇ ⁇ 1 ⁇ ⁇ 2 /10000)
  • E A is the efficacy percentage observed for component A at the dosage d A
  • E B1 is the efficacy percentage observed for component Bl at the dosage d B i
  • E B2 is the efficacy percentage observed for component B2 at the dosage d B 2.
  • compositions object of the present invention show an extremely high fungicidal activity, which is exerted with respect to numerous phytopathogenic fungi attacking important agricultural crops.
  • phytopathogenic fungi that can be effectively fought with the compositions of the present invention, are those belonging to the groups of Basidiomycetes , Ascomycetes, Deuteromycetes or imperfect fungi, Oomycetes: Puccinia spp . , Ustilago spp .
  • Tilletia spp. Uromyces spp., Phakopsora spp., Rhizoctonia spp., Erysiphe spp., Sphaerotheca spp., Podosphaera spp., Uncinula spp., Helminthosporium spp., Rhynchosporium spp., Pyrenophora spp., Monilinia spp., Sclerotinia spp., Septoria spp.
  • ⁇ Mycosphaerella spp. Venturia spp., Botrytis spp., Alternaria spp., Fusarium spp., Cercospora spp., Cercosporella herpotrichoides, Colletotrichum spp., Pyricularia oryzae, Sclerotium spp., Phytophtora spp., Pythium spp., Plasmopara viticola, Peronospora spp., Pseudoperonospora cubensis, Bremia lactucae .
  • the main crops that can be protected with the compositions according to the present invention comprise cereals (wheat, barley, rye, oats, rice, maize, sorghum, etc.), fruit trees (apples, pears, plums, peaches, almonds, cherries, bananas, grapes, strawberries, raspberries, blackberries, etc.), citrus trees (oranges, lemons, mandarins, grapefruit, etc.), legumes (beans, peas, lentils, soybean, etc.), vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, eggplants, peppers, etc.), cucurbitaceae (pumpkins, zucchini, cucumbers, melons, watermelons, etc.), oleaginous plants (sunflower, rape, peanut, castor, coconut, etc.), tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton.
  • cereals wheat, barley, rye, oats, rice, maize, sorg
  • compositions of the present invention have proved to be particularly effective in the control of Plasmopara viticola on vines, Phytophtora infestans and Botrytis Cinerea on tomatoes, Puccinia recondita, Erysiphae graminis,
  • compositions of the present invention are also effective in the control of phytopathogenic bacteria and viruses, such as, for example, Xanthomonas spp., Pseudomonas spp., Erwinia amylovora, the tobacco mosaic virus.
  • the compositions object of the present invention are capable of exerting a fungicidal action of a curative, preventive or eradicating nature, and generally have a very low or null phytotoxicity on the crops treated.
  • a further object of the present invention therefore relates to the use of the synergistic fungicidal compositions described above for the control of phytopathogenic fungi in agricultural crops.
  • the fungicidal compositions for practical use in agriculture, it is often preferable to use the fungicidal compositions, according to the present invention, in the form of suitable formulations.
  • the compounds having general formula (I) and the fungicidal compounds which form components [B] of the composition can be formulated separately and mixed in the preselected diluent (for example water) at the moment of treatment, or combined together in a single formulation before treatment.
  • the formulations can be in the form of dry powders, wettable powders, emulsifiable concentrates, emulsions, micro-emulsions, pastes, granules, water-dispersible granules, solutions, suspensions, etc.: the selection of the type of formulation depends on the characteristics of components A and B and on the specific use.
  • the fungicidal compositions are prepared with known methods, for example by dilution of the active substances with a solid or liquid diluent, possibly in the presence of surfactants, dispersers, suspending agents, stabilizers, adjuvants, etc..
  • silica silica, kaolin, bentonite, talc, diatomaceous earth, dolomite, calcium carbonate, magnesia, gypsum, clays, synthetic silicates, attapulgite, seppiolites.
  • solvents or liquid diluents in addition to water, aromatic organic solvents (xyloles or alkylbenzole mixtures, chlorobenzene, etc.), paraffins (oil cuts), alcohols (methanol, propanol, butanol, octanol, glycerol, etc.), esters (ethyl acetate, isobutyl acetate, alkyl carbonates, alkyl esters of adipic acid, alkyl esters of glutaric acid, alkyl esters of succinic acid, alkyl esters of lactic acid, etc.), vegetable oils (rapeseed oil, sunflower oil, soybean oil, castor oil, corn oil, peanut oil, and their alkyl esters), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethyl amyl ketone, etc.), amides (N, N- dimethylformamide,
  • Surfactants that can be used are sodium salts, calcium salts, potassium salts, triethylamine or triethanolamine of alkylnaphthalensulfonates , polynaphthalenesulfonates , alkylsulfonates, arylsulfonates , alkylarylsulfonates , polycarboxylates , sulfosuccinates , alkylsulfosuccinates , lignin sulfonates, alkyl sulfates; and again polyethoxylated fatty alcohols, polyethoxylated alkyl phenols, polyethoxylated esters of sorbitol, polyethoxylated polypropoxy (block copolymers), can be used.
  • the fungicidal compositions can also contain special additives for particular purposes, for example antifreeze agents such as propylene glycol, or adhesives such as Arabic gum, polyvinyl alcohol, polyvinylpyr
  • fungicidal compositions containing compounds having general formula (I) and components [B] can be added to the fungicidal compositions containing compounds having general formula (I) and components [B] , such as, for example, fungicides other than components [A] an [B] described above, insecticides, phytoregulators , antibiotics, herbicides, fertilizers and/or mixtures thereof.
  • fungicides other than components [A] and [B] that can be included in the fungicidal compositions object of the present invention are listed hereunder with their international ISO name: ampropylfos, anilazine, blasticidin-S , bupirimate, buthiobate, chinomethionat , chloroneb, chlozolinate , debacarb, dichlofluanid, dichlone, diclobutrazol , diclomezine, dicloran, diclocymet, diethofencarb, diflumetorim, dimethirimol , diniconazole, dinocap, dipyrithione, ditalimfos, dithianon, edifenphos, etaconazole, ethirimol, ethoxyquin, etridiazole, fenaminosulf , fenapanil, fenarimol, fenfuram, f
  • weight ratios of components [A] and [B] in the above compositions vary depending on the compounds selected and can normally range from 1:100 to 100:1, preferably from 1:10 to 10:1.
  • the total concentration of components [A] and [B] in the above compositions can vary within a wide range; it generally ranges from 1% to 99% by weight with respect to the total weight of the composition, preferably from 5% to 90% by weight with respect to the total weight of the composition.
  • compositions, object of the present invention can be applied to any part of the plant, for example on the leaves, stems, branches or roots, or on the seeds themselves before sowing, or on the ground in which the plant grows .
  • a further object of the present invention therefore relates to a method for the control of phytopathogenic fungi in agricultural crops, which comprises applying at least one effective and non- phytotoxic dose of at least one synergistic fungicidal composition of the type described above on any part of the plant to be protected or on the ground in which the plant grows .
  • the total quantity of components [A] and [B] to be applied in order to obtain the desired effect can vary according to different factors such as, for example, the compounds used, the crop to be preserved, the type of pathogen, the degree of infection, the climatic conditions, the application method, the formulation used.
  • the treated plants and some untreated plants, used as control were sprayed on both sides of the leaves, with an aqueous solution of conidia of Puccinia recondita (2 mg of inoculum per 1 ml of solution for infection) .
  • an aqueous solution of conidia of Puccinia recondita (2 mg of inoculum per 1 ml of solution for infection) .
  • the plants were kept in a humidity-saturated environment, at a temperature ranging from 18 to 24°C for the incubation period of the fungus (1 day) .
  • the plants were placed in a greenhouse having a Relative Humidity of 70% and a temperature of 18-24 °C for a period of 14 days.
  • the fungicidal activity was expressed as a percentage of the leaf area not affected with respect to the control plants: the value 100 (healthy plant) and the value 0 (plant completely infected) are the extremes considered.
  • the synergy of the compositions was evaluated by means of the Colby formula :
  • E T E A +E B - ( ⁇ ⁇ ⁇ ⁇ /100) wherein E t is the efficacy percentage expected for the composition containing compounds A and B at dosages d A + d B , E A is the efficacy percentage observed for component A at the dosage d A , E B is the efficacy percentage observed for component B at the dosage d B .
  • composition A + B (E A+B ) is higher than the efficacy expected according to the Colby formula (E A+B /E t > 1), the composition is synergistic .
  • Components A and B tested were: compounds 1, 3 (page 5), tetraconazole, epoxyconazole, prothioconazole, bixafen, boscalid, azoxystrobin, pyraclostrobin and chlorothalonil ; compositions tested were CI, C5, C8, C12, C13, C20, C24, C34 and C68 (pages 8-10) .
  • SC suspension concentrate .

Abstract

La présente invention concerne des compositions fongicides synergiques comprenant : [A] au moins une phénylamidine de formule générale (I) ; [B] au moins un second composé à activité fongicide ; et leur utilisation pour la lutte contre les champignons phytopathogènes dans les cultures agricoles.
PCT/IB2013/051978 2012-03-15 2013-03-13 Compositions synergiques à activité fongicide et leur utilisation WO2013136275A1 (fr)

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ITMI2012A000405 2012-03-15
IT000405A ITMI20120405A1 (it) 2012-03-15 2012-03-15 "composizioni sinergiche ad attivita' fungicida e relativo uso"

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Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015121802A1 (fr) * 2014-02-12 2015-08-20 Isagro S.P.A. Benzoylphényl-formamidines ayant une activité fongicide, leurs compositions agronomiques et leur utilisation
EP3011832A1 (fr) 2015-06-15 2016-04-27 Bayer CropScience AG Combinaison fongicide contenant du phenoxyphenylamidine et un l'autre fongicide
CN105766930A (zh) * 2016-04-26 2016-07-20 南京华洲药业有限公司 一种含氟唑菌酰胺和环氟菌胺的杀菌组合物及其应用
WO2016202688A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
US20180160684A1 (en) * 2015-06-01 2018-06-14 Ishihara Sangyo Kaisha, Ltd. Fungicide composition and plant disease control method
EP3335559A1 (fr) 2016-12-14 2018-06-20 Bayer CropScience Aktiengesellschaft Combinaisons de composés actifs
WO2018108998A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénylamidines et leur utilisation en tant que fongicides
WO2018108992A2 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines et leur utilisation en tant que fongicides
WO2018109002A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
WO2018193385A1 (fr) 2017-04-20 2018-10-25 Pi Industries Ltd. Nouveaux composés de phénylamine
WO2018211442A1 (fr) 2017-05-18 2018-11-22 Pi Industries Ltd. Composés de formimidamidine utiles contre des micro-organismes phytopathogènes
US10588318B2 (en) 2014-12-30 2020-03-17 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
EP3708565A1 (fr) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphénylamidines et leur utilisation comme fongicides
US10912297B2 (en) 2015-07-08 2021-02-09 Bayer Cropscience Aktiengesellschaft Phenoxyhalogenphenylamidines and the use thereof as fungicides
US11155520B2 (en) 2018-03-08 2021-10-26 Dow Agrosciences Llc Picolinamides as fungicides
EP3915971A1 (fr) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phényl-s(o)n-phénylamidines et leur utilisation comme fongicides
US11191269B2 (en) 2017-05-02 2021-12-07 Dow Agrosciences Llc Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses
US11206828B2 (en) 2017-05-02 2021-12-28 Corteva Agriscience Llc Synergistic mixtures for fungal controls in cereals
US11639334B2 (en) 2018-10-15 2023-05-02 Corteva Agriscience Llc Methods for synthesis of oxypicolinamides
CN116349684A (zh) * 2021-12-27 2023-06-30 沈阳中化农药化工研发有限公司 一种含固醇生物合成抑制剂类杀菌剂的杀真菌组合物及其应用
US11771085B2 (en) 2017-05-02 2023-10-03 Corteva Agriscience Llc Synergistic mixtures for fungal control in cereals

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000046184A1 (fr) 1999-02-06 2000-08-10 Aventis Cropscience Gmbh Derive n2-phenylamidine
WO2003024219A1 (fr) 2001-09-10 2003-03-27 Bayer Cropscience S.A. Melange fongicide contenant des derives d'arylamidine
WO2003093224A1 (fr) 2002-05-03 2003-11-13 E.I. Du Pont De Nemours And Company Composes amidinylphenyle et utilisations de ceux-ci comme fongicides
WO2005089547A1 (fr) * 2004-03-05 2005-09-29 Bayer Cropscience Sa Composition fongicide comprenant un derive arylamidine et des composes fongicides connus
WO2005094582A1 (fr) * 2004-03-22 2005-10-13 Basf Aktiengesellschaft Melanges fongicides
WO2007031523A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives fongicides pyridinyloxy substitues phenylamidine
WO2007031513A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives de phenylamidine pesticides thiazolyloxy substitues
WO2007031512A2 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives de biphenylamidine pesticides
WO2007031507A1 (fr) * 2005-09-13 2007-03-22 Bayer Cropscience Ag Préparation fongicide comprenant un dérivé d'arylamidine et deux composés fongicides connus
WO2007031508A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives pesticides phenyloxy substitues phenylamidine
WO2007031524A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives de phenylamidine pesticides pyrimidinyloxy substitues
WO2008110279A1 (fr) 2007-03-12 2008-09-18 Bayer Cropscience Ag Dihalogénophénoxyphénylamidines et leur utilisation comme fongicides
WO2012025450A1 (fr) 2010-08-23 2012-03-01 Isagro Ricerca S.R.L. Phénylamidines ayant une activité fongicide élevée et leur utilisation

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000046184A1 (fr) 1999-02-06 2000-08-10 Aventis Cropscience Gmbh Derive n2-phenylamidine
WO2003024219A1 (fr) 2001-09-10 2003-03-27 Bayer Cropscience S.A. Melange fongicide contenant des derives d'arylamidine
WO2003093224A1 (fr) 2002-05-03 2003-11-13 E.I. Du Pont De Nemours And Company Composes amidinylphenyle et utilisations de ceux-ci comme fongicides
WO2005089547A1 (fr) * 2004-03-05 2005-09-29 Bayer Cropscience Sa Composition fongicide comprenant un derive arylamidine et des composes fongicides connus
WO2005094582A1 (fr) * 2004-03-22 2005-10-13 Basf Aktiengesellschaft Melanges fongicides
WO2007031523A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives fongicides pyridinyloxy substitues phenylamidine
WO2007031513A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives de phenylamidine pesticides thiazolyloxy substitues
WO2007031512A2 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives de biphenylamidine pesticides
WO2007031507A1 (fr) * 2005-09-13 2007-03-22 Bayer Cropscience Ag Préparation fongicide comprenant un dérivé d'arylamidine et deux composés fongicides connus
WO2007031508A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives pesticides phenyloxy substitues phenylamidine
WO2007031524A1 (fr) 2005-09-13 2007-03-22 Bayer Cropscience Ag Derives de phenylamidine pesticides pyrimidinyloxy substitues
WO2008110279A1 (fr) 2007-03-12 2008-09-18 Bayer Cropscience Ag Dihalogénophénoxyphénylamidines et leur utilisation comme fongicides
WO2012025450A1 (fr) 2010-08-23 2012-03-01 Isagro Ricerca S.R.L. Phénylamidines ayant une activité fongicide élevée et leur utilisation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C.D.S. TOMLIN: "Pesticide Manual", 2009, BRITISH CROP PRODUCTION COUNCIL EDITOR
WEEDS, 1967, pages 15,20 - 22

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015121802A1 (fr) * 2014-02-12 2015-08-20 Isagro S.P.A. Benzoylphényl-formamidines ayant une activité fongicide, leurs compositions agronomiques et leur utilisation
US11751568B2 (en) 2014-12-30 2023-09-12 Corteva Agriscience Llc Picolinamide compounds with fungicidal activity
US10595531B2 (en) 2014-12-30 2020-03-24 Dow Agrosciences Llc Use of picolinamide compounds as fungicides
US10588318B2 (en) 2014-12-30 2020-03-17 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US20180160684A1 (en) * 2015-06-01 2018-06-14 Ishihara Sangyo Kaisha, Ltd. Fungicide composition and plant disease control method
US10252977B2 (en) 2015-06-15 2019-04-09 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
EP3011832A1 (fr) 2015-06-15 2016-04-27 Bayer CropScience AG Combinaison fongicide contenant du phenoxyphenylamidine et un l'autre fongicide
WO2016202688A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
US10506807B2 (en) 2015-06-15 2019-12-17 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
US10912297B2 (en) 2015-07-08 2021-02-09 Bayer Cropscience Aktiengesellschaft Phenoxyhalogenphenylamidines and the use thereof as fungicides
CN105766930A (zh) * 2016-04-26 2016-07-20 南京华洲药业有限公司 一种含氟唑菌酰胺和环氟菌胺的杀菌组合物及其应用
WO2018108998A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénylamidines et leur utilisation en tant que fongicides
WO2018108992A2 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines et leur utilisation en tant que fongicides
EP3335559A1 (fr) 2016-12-14 2018-06-20 Bayer CropScience Aktiengesellschaft Combinaisons de composés actifs
CN110213965A (zh) * 2016-12-14 2019-09-06 拜耳作物科学股份公司 苯氧基苯基脒及其作为杀真菌剂的用途
WO2018108992A3 (fr) * 2016-12-14 2018-08-02 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines et leur utilisation en tant que fongicides
WO2018108977A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
WO2018109002A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
US11524934B2 (en) 2017-04-20 2022-12-13 Pi Industries Ltd Phenylamine compounds
WO2018193385A1 (fr) 2017-04-20 2018-10-25 Pi Industries Ltd. Nouveaux composés de phénylamine
US11191269B2 (en) 2017-05-02 2021-12-07 Dow Agrosciences Llc Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses
US11206828B2 (en) 2017-05-02 2021-12-28 Corteva Agriscience Llc Synergistic mixtures for fungal controls in cereals
US11771085B2 (en) 2017-05-02 2023-10-03 Corteva Agriscience Llc Synergistic mixtures for fungal control in cereals
WO2018211442A1 (fr) 2017-05-18 2018-11-22 Pi Industries Ltd. Composés de formimidamidine utiles contre des micro-organismes phytopathogènes
US11155520B2 (en) 2018-03-08 2021-10-26 Dow Agrosciences Llc Picolinamides as fungicides
US11639334B2 (en) 2018-10-15 2023-05-02 Corteva Agriscience Llc Methods for synthesis of oxypicolinamides
EP3708565A1 (fr) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphénylamidines et leur utilisation comme fongicides
EP3915971A1 (fr) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phényl-s(o)n-phénylamidines et leur utilisation comme fongicides
CN116349684A (zh) * 2021-12-27 2023-06-30 沈阳中化农药化工研发有限公司 一种含固醇生物合成抑制剂类杀菌剂的杀真菌组合物及其应用

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