WO2018024147A1 - Composition fongicide synergique et utilisation de celle-ci - Google Patents

Composition fongicide synergique et utilisation de celle-ci Download PDF

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Publication number
WO2018024147A1
WO2018024147A1 PCT/CN2017/094632 CN2017094632W WO2018024147A1 WO 2018024147 A1 WO2018024147 A1 WO 2018024147A1 CN 2017094632 W CN2017094632 W CN 2017094632W WO 2018024147 A1 WO2018024147 A1 WO 2018024147A1
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Prior art keywords
crystalline modification
boscalid
pyraclostrobin
range
composition
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PCT/CN2017/094632
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English (en)
Inventor
James Timothy BRISTOW
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Jiangsu Rotam Chemical Co Ltd
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Jiangsu Rotam Chemical Co Ltd
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Application filed by Jiangsu Rotam Chemical Co Ltd filed Critical Jiangsu Rotam Chemical Co Ltd
Priority to BR112017022487-9A priority Critical patent/BR112017022487B1/pt
Priority to CN201780047244.7A priority patent/CN109561686A/zh
Publication of WO2018024147A1 publication Critical patent/WO2018024147A1/fr
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    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

  • the present invention relates to a synergistic fungicidal composition.
  • the composition finds use in preventing and/or treating fungal infestations in plants and plant parts.
  • the present invention also relates to a method of preventing and/or treating fungal infestations in plants and plant parts.
  • Such formulations are, for example, granules, encapsulated granules, tablets, water-dispersible granules, water-dispersible tablets, water-dispersible powders or water dispersible powders for seed treatment, dust formulations, and formulations in which the active compound is present in dispersed form, such as, for example, suspension concentrates, oil-based suspension concentrates, suspoemulsions, or suspension concentrates for seed treatment. Hydration of the crystalline modification I of the anhydrate of boscalid is needed prior formulating into a suspension concentrate.
  • the compound methyl N- [2- [ [ [ [1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxy] methyl] phenyl] -N-methoxycarbamate, having the common name pyraclostrobin, is a known fungicide.
  • Formulations comprising pyraclostrobin for the treatment of fungal infestations in crops are known and are commercially available.
  • US 7,816,392 disclosed four different crystalline modifications, I to IV, of pyraclostrobin.
  • the present invention provides a fungicidal composition comprising:
  • composition of the present invention is of particular use for preventing and/or treating fungal infestations in plants and/or plant parts.
  • the present invention provides a method of preventing and/or treating fungal infestations in plants and/or plant parts comprising applying to the plants and/or plant parts:
  • the present invention provides the use in the prevention and/or treatment of fungal infestations in plants and/or plant parts of:
  • references to the crystalline modification II of boscalid as used herein refer to the crystalline modification of boscalid disclosed in US 7,501,384.
  • the references to the crystalline modifications I to IV of pyraclostrobin as used herein refer to the crystalline modifications of pyraclostrobin disclosed in US 7,816,392.
  • Plant refers to all plant and plant populations such as desired and undesired wild plants or crop plants.
  • Plant parts refers to all parts and organs of plants, such as shoot, leaves, needles, stalks, stems, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • Harvested materials, and vegetative and generative propagation materials for example, cutting, tubers, meristem tissue, rhizomes, offsets, seeds, single and multiple plant cells and any other plant tissues, are also included.
  • locus refers to the place on which the plants are growing, the place on which the plant propagation materials of the plants are sown or the place on which the plant propagation materials of the plants will be sown.
  • At least one designates a number of the respective compounds or components of 1, 2, 3, 4, 5, 6, 7, 8, 9 or more, preferably 1, 2, or 3.
  • the synergistic fungicidal composition, the method and use of the present invention are suitable for the treatment of plants of a wide range of crops, including: cereals, for example wheat, barley, rye, oats, corn, rice, sorghum, triticale and related crops; fruit, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, pistachio, almonds, cherries, and berries, for example grape, banana, strawberries, bushberry, caneberry, raspberries and blackberries; leguminous plants, for example beans, lentils, peas, and soybeans; oil plants, for example oilseed rape, mustard and sunflowers; cucurbitaceae, for example cantaloupe, marrows, cucumbers, melons, pumpkin, squash and watermelon; citrus fruit, such as oranges, lemons, grapefruit and mandarins; and vegetables, for example spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika,
  • compositions, method and use of the present invention are particularly advantageous when applied to cereals, fruit, leguminous plants, oil plants and vegetables.
  • composition, method and use of the present invention are of advantage when applied to wheat, barley, oats, rice, grape, banana, soybean, oilseed rape and vegetables.
  • composition, method and use of the present invention can be used in the agricultural sector and related fields of use for preventing and/or treating fungal infestations, including but not limited to:
  • Leaf rust (Puccinia coronate var. avenae) ;
  • Barley Stain-brown; common root rot (Bipolaris sorokiniana) ; spot-type net blotch, blotch (Drechslera/Pyrenophora teres) ; Leaf blotch (Rhynchosporium secalis) ; Ramularia leaf spot (Ramularia collo-cygni) ; Brown rust (Puccinia hordei) ; powdery mildew (Blumeria graminis) ;
  • tan spot helminthosporiosis (Pyrenophora tritici-repentis) ; leaf/brown rust (Puccinia triticina, Puccinia tritici-duri) ; Septoria tritici blotch, Septoria (Septoria tritici) ; glume blotch (stagonospora nodorum) ; Helminthosporiose; common root rot (Bipolaris sorokiniana) ; powdery mildew (Blumeria graminis) ; yellow rust (Puccinia strillformis) ;
  • Alternaria leaf spot and fruit rot Alternaria spp. ) ; Anthracnose (Colletotrichum spp., Elsinoe spp. ) ; Botrytis gray mold (Botrytis cinerea) ; Leaf spot and blotch (Mycosphaerella spp., Septoria spp., Mycosphaerella fijiensis) ; Monilinia blight and mummy berry (Monilinia spp. ) ; Phomopsis leaf spot, twig blight, and fruit rot (Phomopsis spp.
  • Powdery mildew (Sphaerotheca spp., Microsphaera spp., Oidium spp. ) ; Spur blight (Didymella spp., Phoma spp. ) ; Mal-de-Sigatoka, Sigatoka (Musicola Mycosphaerella) ;
  • Grapes Angular leaf spot (Mycosphaerella angulata) ; Anthracnose (Elsinoe ampelina) ; Black rot (Guignardia bidwellii) ; Downy mildew (Plasmopara viticola) ; Leaf blight (Pseudocercospora vitis) ; Phomopsis cane and leaf spot (Phomopsis viticola) ; Powdery mildew (Uncinula necator) ; Ripe rot (Colletotrichum gloeosporioides) ; Summer bunch rot (Sour rot) (Cladosporium spp. and Aspergillus spp. ) ; Botrytis gray mold (Botrytis cinerea) ;
  • Soybean Phakopsora pachyrhizi
  • Botrytis leaf blight Botrytis spp.
  • Botrytis neck rot Botrytis spp.
  • Purple blotch and leaf blight (Alternaria porri)
  • Stemphylium leaf blight and stalk rot (Stemphylium vesicarium)
  • Downy mildew Peronospora destructor) ;
  • Carrots Alternaria leaf spot (Alternaria spp. ) ; Cercospora leaf spot (Cercospora spp. ) ; Powdery mildew (Erysiphe spp. ) ; Southern root rot (Sclerotium rolfsii) ; yiuch;
  • Cucurbit Vegetables Downy mildew (Pseudoperonospora cubensis) ; Alternaria blight (Alternaria cucumerina) ; Cercospora leaf spot (Cercospora citrulina) ; Gummy stem blight (Didymella bryoniae) ; Powdery mildew (Sphaerotheca fuliginea, Erysiphe cichoracearum) ; Anthracnose (Colletotrichum orbiculare) ;
  • Hops Powdery mildew (Erysiphe cichoracearum, Sphaerotheca spp. ) ; Downy mildew (Pseudoperonospora humuli) ; Powdery mildew (Erysiphe cichoracearum, Sphaerotheca humuli, Sphaerotheca macularis, Sphaerotheca spp. ) ;
  • Pistachio Alternaria late blight (Alternaria spp. ) ; Botrytis blossom and shoot blight (Botrytis cinerea) ; Panicle and shoot blight (Botryosphaeria dothidea) ;
  • Pome Fruits Alternaria blotch (Alternaria mali) ; Apple scab (Venturia inaequalis) ; Bitter rot (Colletotrichum spp. ) ; Black rot/Frogeye leaf spot (Botryosphaeria obtusa) ; Blue mold (Penicillium spp. ) ; Brooks spot (Mycosphaerella pomi) ; Flyspeck (Zygophiala jamaicensis) ; Gray mold (Botrytis spp.
  • Pear scab (Venturia pirina) ; Powdery mildew (Podosphaera leucotricha) ; Sooty blotch (disease complex) ; White rot (Botryosphaeria dothidea) ; Cedar apple rust (Gymnosporangium juniperi-virginianae) ; Quince rust (Gymnosporangium clavipes) ;
  • Oilseed rape phoma (Leptosphaeria maculans) ; light leaf spot (Pyrenopeziza brassicae) ; Sclerotinia sclerotiorum;
  • Powdery mildew Podospheara leucotricha; Sphaerotheca pannosa
  • scab Vorenturia inaequalis
  • Stone Fruits Alternaria leaf spot (Alternaria spp. ) ; Anthracnose (Colletotrichum spp. ) ; Blossom blight (Monilinia spp. ) ; Brown rot (Monilinia spp. ) ; Leaf spot (Blumeriella jaapii) ; Powdery mildew (Sphaerotheca spp., Podosphaera spp. ) ; Ripe fruit rot (Monilinia fructicola, Monilinia laxa, Botrytis cinerea, Rhizopus spp. ) ; Rust (Tranzschelia discolor) ; Scab (Cladosporium carpophilum) ; Shothole (Wilsonomyces carpophilus) ;
  • Strawberries Anthracnose (Colletotrichum spp. ) ; Botrytis gray mold (Botrytis cinerea) ; Leaf spot (Mycosphaerella fragariae) ; Powdery mildew (Sphaerotheca macularis) ;
  • Tree Nuts Alternaria leaf spot (Alternaria spp. ) ; Anthracnose (Colletotrichum spp. ) ; Blossom blight (Monilinia spp. ) ; Eastern filbert blight (Anisogramma anomala) ; Leaf rust (Tranzschelia discolor) ; Scab (Cladosporium carpophilum, C. caryigenum) ; Green fruit rot (Botrytis cinerea) ; Shothole (Wilsonomyces carpophilus) ;
  • Vegetables Downy mildew (Plasmopara spp. ) ; Powdery mildew (Oidium spp. ) ; Botrytis gray mold (Botrytis cinerea) .
  • the fungicidal composition, method and use of the present invention exhibit surprisingly high effectiveness in treating and/or preventing fungal diseases caused by fungal pathogens, including:
  • blotch (Drechslera/Pyrenophora teres) ;
  • Leaf blotch (Rhynchosporium secalis) ;
  • Ramularia leaf spot (Ramularia collo-cygni) ;
  • Grapes Downy mildew (Plasmopara viticola) ; Powdery mildew (Uncinula necator) ; Botrytis gray mold (Botrytis cinerea) ;
  • Soybean Phakopsora pachyrhizi
  • Oilseed rape phoma (Leptosphaeria maculans) ; light leaf spot (Pyrenopeziza brassicae) ; Sclerotinia sclerotiorum;
  • Powdery mildew Podospheara leucotricha; Sphaerotheca pannosa
  • scab Vorenturia inaequalis
  • Vegetables Downy mildew (Plasmopara spp. ) ; Powdery mildew (Oidium spp. ) ; Botrytis gray mold (Botrytis cinerea) .
  • composition of the present invention comprises (A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N- (4’ chloro [1, 1’ biphenyl] -2-yl) (boscalid) ; and (B) the crystalline modification IV of methyl N- ⁇ 2- [1- (4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] phenyl ⁇ (N-methoxy) carbamate (pyraclostrobin) .
  • the crystalline modification II of boscalid may be present in the synergistic fungicidal composition of the present invention in any suitable amount, and is preferably present in an amount of up to 80%by weight, more preferably up to 70%by weight, still more preferably up to 60%by weight.
  • the crystalline modification II of boscalid may be present in an amount of from about 1%to about 80%by weight of the composition, preferably from about 1%to 70%by weight, more preferably from about 1%to about 60%by weight of the composition.
  • the crystalline modification IV of pyraclostrobin may be present in the synergistic fungicidal composition in any suitable amount, and is preferably present in an amount of up to 70%by weight, more preferably up to 60%by weight, still more preferably up to 50%by weight.
  • the crystalline modification IV of pyraclostrobin may be present in an amount of from about 1%to about 70%by weight of the composition, preferably from about 1%to about 60%by weight, more preferably from about 1%to about 50%by weight of the composition.
  • the components (A) and (B) may be employed in the composition, method or use of the present invention in any suitable weight ratio.
  • the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin in the composition may be in the range of from about 50: 1 to about 1: 50, preferably from about 25: 1 to about 1: 25, more preferably from about 20: 1 to about 1: 20, still more preferably from about 15:1 to about 1: 15, more preferably still from about 10: 1 to about 1: 10.
  • a preferred weight ratio for many embodiments is about 5: 1 to about 1: 5.
  • compositions of the present invention may be produced in a conventional manner, for example by mixing the crystalline modification II of boscalid with the crystalline modification IV of pyraclostrobin, together with auxiliaries appropriate for the form of the formulation.
  • auxiliaries which may be comprised in the composition according to the invention include all customary formulation adjuvants or components, such as extenders, carriers, solvents, surfactants, stabilizers, anti-foaming agents, anti-freezing agents, preservatives, antioxidants, colorants, thickeners, solid adherents and inert fillers.
  • auxiliaries are known in the art and are commercially available. Their use in the formulation of the compositions of the present invention will be apparent to the person skilled in the art.
  • composition of the present invention may be provided in a wide range of formulation types. Suitable formulations includes a water-soluble concentrate (SL) , an emulsifiable concentrate (EC) , an emulsion (EW) , a micro-emulsion (ME) , suspension concentrates (SC) , oil-based suspension concentrates (OD) , a flowable suspension (FS) , water-dispersible granules (WG) , water-soluble granules (SG) , a water-dispersible powder (WP) , a water soluble powder (SP) , granules (GR) , encapsulated granules (CG) , fine granules (FG) , macrogranules (GG) , a suspo-emulsion (SE) , a capsule suspension (CS) and microgranules (MG) .
  • SL water-soluble concentrate
  • EW emulsion
  • ME micro-emulsion
  • the synergistic fungicidal composition is formulated as a suspension concentrate (SC) , water-dispersible granules (WG) , a suspo-emulsion (SE) , a capsule suspension (CS) , an oil-based suspension concentrate (OD) , or water-soluble granules (SG) .
  • SC suspension concentrate
  • WG water-dispersible granules
  • SE suspo-emulsion
  • CS capsule suspension
  • OD oil-based suspension concentrate
  • SG water-soluble granules
  • the fungicidal composition may comprise one or more inert fillers.
  • inert fillers are known in the art and available commercially. Suitable fillers include, for example, natural ground minerals, such as kaolins, aluminas, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, or synthetic ground minerals, such as highly dispersed silicic acid, aluminum oxide, silicates, and calcium phosphates and calcium hydrogen phosphates.
  • Suitable inert fillers for granules include, for example, crushed and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, and dolomite, or synthetic granules of inorganic and organic ground materials, as well as granules of organic material, such as sawdust, coconut husks, corn cobs, and tobacco stalks.
  • the fungicidal composition optionally includes one or more surfactants which are preferably non-ionic, cationic and/or anionic in nature and surfactant mixtures which have good emulsifying, dispersing and wetting properties, depending on the nature of the active compound to be formulated.
  • surfactants are known in the art and are commercially available.
  • Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.
  • Soaps which may be used are the alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts of higher fatty acids (C 10 to C 22 ) , for example the sodium or potassium salt of oleic or stearic acid, or of natural fatty acid mixtures.
  • the surfactant can be an emulsifier, dispersant or wetting agent of ionic or nonionic type.
  • examples which may be used are salts of polyacrylic acids, salts of lignosulphonic acid, salts of phenylsulphonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols, especially alkylphenols, sulphosuccinic ester salts, taurine derivatives, especially alkyltaurates, or phosphoric esters of polyethoxylated phenols or alcohols.
  • the presence of at least one surfactant is generally required when the active compound and/or the inert carrier and/or auxiliary/adjuvant are insoluble in water and the vehicle for the final application of the composition to the plants or plant parts is water.
  • the fungicidal composition optionally further comprises one or more polymeric stabilizers.
  • the suitable polymeric stabilizers that may be used in the present invention include, but are not limited to, polypropylene, polyisobutylene, polyisoprene, copolymers of monoolefins and diolefins, polyacrylates, polystyrene, polyvinyl acetate, polyurethanes or polyamides. Suitable stabilizers are known in the art and commercially available.
  • surfactants and polymeric stabilizers mentioned above are generally believed to impart stability to the composition, in turn allowing the composition to be formulated, stored, transported and applied.
  • Suitable anti-foam agents include all substances which can normally be used for this purpose in agrochemical compositions. Suitable anti-foam agents are known in the art and are available commercially. Particularly preferred antifoam agents are mixtures of polydimethylsiloxanes and perfluroalkylphosphonic acids, such as the silicone anti-foam agents available from GE or Compton.
  • Suitable organic solvents may be selected from all customary organic solvents which thoroughly dissolve the active compounds employed. Again, suitable organic solvents for tebuconazole and chlorothalonil are known in the art. The following may be mentioned as being preferred: N-methyl pyrrolidone, N-octyl pyrrolidone, cyclohexyl-1-pyrrolidone; or SOLVESSO TM 200, a mixture of paraffinic, isoparaffinic, cycloparaffinic and aromatic hydrocarbons. Suitable solvents are commercially available.
  • Suitable preservatives include all substances which can normally be used for this purpose in agrochemical compositions of this type and again are well known in the art. Suitable examples that may be mentioned include (from Bayer AG) and (from Bayer AG) .
  • Suitable antioxidants are all substances which can normally be used for this purpose in agrochemical compositions, as is known in the art. Preference is given to butylated hydroxytoluene.
  • Suitable thickeners include all substances which can normally be used for this purpose in agrochemical compositions.
  • thickeners are known in the art and available commercially.
  • the fungicidal composition may further comprise one or more solid adherents.
  • adherents are known in the art and available commercially. They include organic adhesives, including tackifiers, such as celluloses of substituted celluloses, natural and synthetic polymers in the form of powders, granules, or lattices, and inorganic adhesives such as gypsum, silica, or cement.
  • composition according to the invention may also comprise water.
  • the formulated composition may for example be applied in spray form, for example employing appropriate dilutions using a diluent, such as water.
  • the rates of application (use) of the components (A) and (B) in the method and use of the present invention may vary, for example, according to type of use, soil type, season, climate, soil ecology, type of plants, but are such that the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin are both applied in an effective amount to provide the desired action.
  • the application rate of the components (A) and (B) for a given set of conditions can readily be determined by routine trials.
  • the application rate of the synergistic fungicidal composition of the present invention lies in the range of from about 1 to 3 liters or kg per ha.
  • the application rate of the total amount of component (A) , the crystalline modification II of boscalid, and component (B) , the crystalline modification IV of pyraclostrobin, in the method and use of the invention preferably lies in the range of from about 50 to 2000 gram per hectare, more preferably from about 100 to about 1000 gram per hectare.
  • formulations either straight (that is undiluted) or diluted with a suitable solvent, especially, water, plants, plant parts and/or the locus can be treated and protected against fungal infestations by techniques known in the art.
  • a suitable solvent especially, water, plants, plant parts and/or the locus
  • the formulations containing the active ingredients can be diluted with water.
  • the composition can be applied with the methods known in the art. These methods include coating, spraying, dipping, pouring, immersing, soaking, injection, irrigation and the like.
  • Components (A) and (B) can be applied to the plants, plant parts and/or locus where control is desired either simultaneously and/or in succession, preferably at short intervals, for example on the same day.
  • the components (A) and (B) may be applied to the plant, one or more parts thereof (such as leaves or seeds) , or the locus thereof in any order. Each component may be applied just once or a plurality of times. Preferably, each of the components (A) and (B) is applied a plurality of times, in particular from 1 to 6 times.
  • Components (A) and (B) may be applied in any suitable form, as described above.
  • the active components will be applied as formulations, that is compositions comprising one or more of the active components together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology.
  • components (A) and (B) are applied simultaneously in the present invention, they may be applied as a composition containing components (A) and (B) , in which case components (A) and (B) can be obtained from a separate formulation source and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry) , optionally with other pesticides, or components (A) and (B) can be obtained as a single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product) ) , and optionally mixed together with other pesticides.
  • a separate formulation source known as a tank-mix, ready-to-apply, spray broth, or slurry
  • components (A) and (B) can be obtained as a single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product) ) , and optionally mixed together with other pesticides.
  • the method and use of the present invention employ a composition according to the present invention.
  • compositions according to the invention are distinguished by the fact that they are especially well tolerated by plants being treated and are environmentally friendly.
  • a suspension concentrate (SC) comprising the crystalline II modification of boscalid was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 25.2% Propylene glycol 10% Tristyrylphenol ethoxylates 5%
  • a suspension concentrate (SC) comprising the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification IV pyraclostrobin 12.8% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • a suspension concentrate (SC) comprising the crystalline I modification of boscalid and the crystalline I modification of pyraclostrobin was prepared from the components set out in the following table.
  • a suspension concentrate (SC) comprising the crystalline I modification of boscalid and the crystalline II modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification I boscalid 25.2% Crystalline modification II pyraclostrobin 12.8% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • a suspension concentrate (SC) comprising the crystalline I modification of boscalid and the crystalline III modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification I boscalid 25.2% Crystalline modification III pyraclostrobin 12.8% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • a suspension concentrate (SC) comprising the crystalline I modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • a suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline I modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 25.2% Crystalline modification I pyraclostrobin 12.8% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • Example 8 -Crystalline modification II boscalid + crystalline modification II pyraclostrobin suspension concentrate (SC)
  • a suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline II modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 25.2% Crystalline modification II pyraclostrobin 12.8% Propylene glycol 10%
  • a suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline III modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 25.2% Crystalline modification III pyraclostrobin 12.8% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • a suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 25.2% Crystalline modification IV pyraclostrobin 12.8% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1%
  • a suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 16.67% Crystalline modification IV pyraclostrobin 10% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • Example 12 -Crystalline modification II boscalid + crystalline modification IV pyraclostrobin water dispersible granules (WG)
  • a water dispersible granule (WG) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • a capsule suspension (SC) comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Example 14 -Crystalline modification II boscalid + crystalline modification IV pyraclostrobin water dispersible granules (WG)
  • a water dispersible granule (WG) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • a water soluble granule (SG) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 25% Crystalline modification IV pyraclostrobin 15% Sodium lauryl sulfate 0.5% Sodium lignosulfonate 4.5% Lactose 55%
  • a flowable suspension (FS) comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 3% Crystalline modification IV pyraclostrobin 1.67% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • a suspo-emulsion (SE) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Example 18 -Crystalline modification II boscalid + crystalline modification IV pyraclostrobin oil-based suspension concentrate (OD)
  • An oil-based suspension concentrate (OD) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification II boscalid 40% Crystalline modification IV pyraclostrobin 20% Tristyrylphenol ethoxylates 7.5% Sodium lignosulfonate 1.5% Silicon dioxide 1.5% Silicone oil 1.5% Vegetable oil Balance to 100%
  • a water dispersible granule (WG) composition comprising the crystalline II modification of boscalid was prepared from the components set out in the following table.
  • a suspension concentrate (SC) composition comprising the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
  • Crystalline modification IV pyraclostrobin 30% Propylene glycol 10% Tristyrylphenol ethoxylates 5% Sodium lignosulfonate 1% Carboxymethylcellulose 1% Silicone oil (in the form of a 75%emulsion in water) 1% Water Balance to 1L
  • the expected activity for a given combination of two active compounds can be calculated by the so called “Colby equation” (see S.R. Colby, “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations” , Weeds 1967, 15, 20-22) :
  • A the activity percentage of compound A when active compound A is empolyed at an application rate of m g/ha;
  • E the percentage of estimated activity when compounds A and B are empolyed together at an application rate of m g/ha and n g/ha;
  • the severity of the fungal infestation is indicated in the following examples in terms of the percentage of the plant observed to be infested with the indicated fungus.
  • Grape plants were sprayed with a conidial suspension of Plasmopara viticola and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions of Formulations Examples 1 to 20 set out above. The treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which, the severity of the fungal infestation was assessed.
  • Grape plants were sprayed with a conidial suspension of Uncinula necator and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. Thereafter, the plants were sprayed with compositions of Formulations Examples 1 to 20 set out above. The treated plants were kept in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Grape plants were sprayed with a conidial suspension of Botrytis cinerea and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then were sprayed with compositions of the Formulations Examples 1 to 20 set out above. After treatment, the plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, following which the severity of the fungal infestation was assessed. The results are set out in the following table.
  • Barley plants were sprayed with a conidial suspension of Drechslera/Pyrenophora teres and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then were sprayed with compositions of Formulations Examples 1 to 20 set out above. After treatment, the plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days. The severity of the fungal infestation was then assessed.
  • Barley plants were sprayed with a conidial suspension of Rhynchosporium secalis and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions of Formulations Examples 1 to 20 set out above. The treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Barley plants were sprayed with a conidial suspension of Ramularia collo-cygni and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then were sprayed with compositions of Formulations Examples 1 to 20 set out above. The treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Wheat plants were sprayed with a conidial suspension of Septoria tritici and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Wheat plants were sprayed with a conidial suspension of stagonospora nodorum and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Banana plants were sprayed with a conidial suspension of Mycosphaerella fijiensis and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Soybean plants were sprayed with a conidial suspension of Phakopsora pachyrhizi and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Oilseed rape plants were sprayed with a conidial suspension of Leptosphaeria maculans and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Oilseed rape plants were sprayed with a conidial suspension of Pyrenopeziza brassicae and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Oilseed rape plants were sprayed with a conidial suspension of Sclerotinia sclerotiorum and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Apple plants were sprayed with a conidial suspension of Podosphaera leucotricha and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Peach plants were sprayed with a conidial suspension of Sphaerotheca pannosa and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Pear plants were sprayed with a conidial suspension of Venturia inaequalis and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Cabbage plants were sprayed with a conidial suspension of Plasmopara spp. and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Tomato plants were sprayed with a conidial suspension of Oidium spp. and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
  • Cucumber plants were sprayed with a conidial suspension of Botrytis cinerea and incubated at conditions of 20°C and 100%relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80%relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.

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  • Chemical & Material Sciences (AREA)
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Abstract

L'invention concerne une composition fongicide synergique comprenant : (A) la modification cristalline II de 3-pyridinecarboxamide, 2-chloro-N-(4'chloro[1,1'biphényl]-2-yl) (boscalide); et (B) la modification cristalline IV de N-{2-[1-(4-chlorophényl)-1H-pyrazol-3-yloxyméthyl] phényl}(N-méthoxy)carbamate de méthyle (pyraclostrobine). L'invention concerne également un procédé de traitement d'infestations fongiques chez des végétaux et des matières végétales.
PCT/CN2017/094632 2016-08-04 2017-07-27 Composition fongicide synergique et utilisation de celle-ci Ceased WO2018024147A1 (fr)

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CN102595879A (zh) * 2009-11-06 2012-07-18 巴斯夫欧洲公司 4-羟基苯甲酸和选定农药的结晶配合物

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GB2552694B (en) 2020-03-04
GB2552694A (en) 2018-02-07

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