WO2010072634A2 - Méthode de traitement post-récolte - Google Patents

Méthode de traitement post-récolte Download PDF

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Publication number
WO2010072634A2
WO2010072634A2 PCT/EP2009/067294 EP2009067294W WO2010072634A2 WO 2010072634 A2 WO2010072634 A2 WO 2010072634A2 EP 2009067294 W EP2009067294 W EP 2009067294W WO 2010072634 A2 WO2010072634 A2 WO 2010072634A2
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WIPO (PCT)
Prior art keywords
methyl
carboxamide
pyrazole
phenyl
difluoromethyl
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PCT/EP2009/067294
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English (en)
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WO2010072634A3 (fr
Inventor
Markus Gewehr
Christina Geiger
Andreas Haase
Ansgar Wille
Alexander Gerding
Thorsten Jabs
Kristin Klappach
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Basf Se
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Publication of WO2010072634A2 publication Critical patent/WO2010072634A2/fr
Publication of WO2010072634A3 publication Critical patent/WO2010072634A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00—Preservation or chemical ripening of fruit or vegetables
    • A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
    • A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
    • A23B7/154—Organic compounds; Microorganisms; Enzymes

Definitions

  • the present invention relates to post-harvest treatment method for the suppression of biological infestation in harvested produce comprising applying to the harvested produce a composition comprising a compound I selected from groups A) to F):
  • carboxamides - carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, car- boxin, fenfuram, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, sedaxane, sedaxane (cis-isomers), sedaxane (trans-isomers), tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl- indan-4-yl)-nicotinamide, N-(2',4'-difluorobipheny
  • triazoles triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difeno- conazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquin- conazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, met- conazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propicona- zole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1-(4-chloro-phenyl)-2-([1 ,2,4]triazol-1-yl)- cycloheptanol
  • D) heterocyclic compounds pyridines fluazinam, pyrifenox, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isox- azolidin-3-yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]- pyridine, 2,3,5,6-tetra-chloro-4-methanesulfonyl-pyridine, 3,4,5-trichloropyridine-
  • nitrophenyl derivates binapacryl, dinobuton, dinocap, nitrthal-isopropyl, tecnazen, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl; - organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide
  • the invention relates also to a use of the postharvest treatment methods defiend herein to lenghten the post-harvest shelf-life of the stored harvested produce.
  • Fungicides from the chemical class of benzimidazoles such as thiabenzadole or eenomyl are the most widely used chemicals for the post-harvest control of fungal infestation in several crops such as pears, apples or bananas (see e.g. D. Sugar and S. R. Basile, Timing and sequence of postharvest fungicide and biocontrol agent applications for control of per decay, Postharvest Biology and Technology 49, (2008), pp. 107-1 12).
  • Practical agricultural experience has shown that exclusive application of a limited number of active compounds from a limited number of compound classes in the control of harmful fungi leads in many cases to a rapid selection of those fungus strains which have developed natural or adapted resistance against the active compound in question, (see e.g. P.
  • a post-harvest treatment method for the suppression of biological infestation in harvested produce comprising applying to the harvested produce a composition comprising a compound I as defined herein and a solvent or solid carrier and a further active compound Il selected from groups A') to F'):
  • B') carboxamides carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, car- boxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, sedaxane, sedaxane (cis-isomers), sedaxane (trans-isomers), te- cloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide,
  • azoles triazoles triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difeno- conazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, flu- quinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propi- conazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadi- mefon, triadimenol, triticonazole, uniconazole, 1-(4-chloro-phenyl)-2- ([1 ,2,4]triazol-1 -yl)-cycloheptano
  • D') heterocyclic compounds pyridines fluazinam, pyrifenox, 3-[5-(4-chloro-phenyl)-2,3-dimethyl- isoxazolidin-3-yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3- yl]-pyridine, 2,3,5,6-tetra-chloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro- pyridine-2,6-di-carbonitrile, N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4- dichloronicotinamide, N-[(5-bromo-3-chloro-pyridin-2-yl)-methyl]-2,4-dichloro- nicotinamide; - pyrimidines: bupirimate, cyprodinil, diflume
  • guanidines guanidine, dodine, dodine free base, guazatine, guazatine- acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate); antibiotics: kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, polyoxine, validamycin A; - nitrophenyl derivates: binapacryl, dinobuton, dinocap, nitrthal-isopropyl, tecnazen, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane; - organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, phosphorous
  • the present invention furthermore relates to the use of the post-harvest treatment methods as defined to lenghten the post-harvest shelf-life of the stored harvested produce.
  • aldimorph "4-alkyl-2,5(or 2,6)-dimethylmorpholine", comprising 65-75% of 2,6- dimethylmorpholine and 25-35% of 2,5-dimethylmorpholine, comprising more than 85% of 4-dodecyl-2,5(or 2,6)-dimethylmorpholine, where "alkyl” also includes octyl, decyl, tetradecyl and hexadecyl, with a cis/trans ratio of 1 :1 [CAS RN 91315-15-0]; dodine, 1-dodecylguanidinium acetate (Plant Dis. Rep., Vol.
  • bitertanol ⁇ -([1 ,1 '-biphenyl]-4-yloxy)- ⁇ -(1 , 1 -dimethylethyl)-1 H-1 ,2,4-triazole-1 -ethanol
  • prothioconazole 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4- dihydro-[1 ,2,4]triazole-3-thione (WO 96/16048); simeconazole, ⁇ -(4-fluorophenyl)- ⁇ -[(trimethylsilyl)methyl]-1 H-1 ,2,4-triazole-1-ethanol [CAS RN 149508-90-7], tebuconazole, 1 -(4-chlorophenyl)-4,4-dimethyl-3-[1 ,2,4]triazol-1 -ylmethylpentan-3-ol
  • EP-A 40 345 tetraconazole, 1 -[2-(2,4-dichlorophenyl)-3-(1 , 1 ,2,2-tetrafluoroethoxy)propyl]-1 H-1 ,2,4- triazole (EP 234 242); triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1 H-1 ,2,4-triazol-1-yl)-2-butanone (BE
  • EP-A 152 031 EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-
  • the post-harvest treatment method comprises as compound I a compound of group A (strobilurins), preferably selected from pyraclostrobin, dimoxystrobin, kresoxim-methyl, azoxystrobin, trifloxystrobin, enestroburin and pyribencarb.
  • group A strobilurins
  • the post-harvest treatment method comprises as compound I pyraclostrobin, dimoxystrobin or kresoxim-methyl, more preferably pyra- clostrobin or kresoxim-methyl.
  • the post-harvest treatment method comprises as compound I a compound of group C (triazoles), preferably selected from epoxicona- zole, difenoconazole, flusilazole, tebuconazol, cyproconazole and prothioconazole, more preferably selected from epoxiconazole or difenoconazole.
  • triazoles preferably selected from epoxicona- zole, difenoconazole, flusilazole, tebuconazol, cyproconazole and prothioconazole, more preferably selected from epoxiconazole or difenoconazole.
  • the post-harvest treatment method comprises as compound I a compound of group B (carboxamides), preferably selected from bixafen, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, sedaxane, sedaxane (cis-isomers), sedaxane (trans-isomers), tecloftalam, thifluzamide, tiadinil, 2-amino-4- methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-(2',4'-difluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(2',4'-dichlorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1-methyl-1 H-pyr
  • the post-harvest treatment method comprises applying as compound I a compound selected from bixafen, isopyrazam, sedaxane, sedaxane (cis-isomers), sedaxane (trans-isomers), N-(3',4',5'-trifluorobiphenyl-2-yl)- 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, dimethomorph, flumorph and pyrimorph.
  • compound I a compound selected from bixafen, isopyrazam, sedaxane, sedaxane (cis-isomers), sedaxane (trans-isomers), N-(3',4',5'-trifluorobiphenyl-2-yl)- 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, dimethomorph, flumorph and pyrimorph.
  • the post-harvest treatment method comprises applying as compound I a compound of group D (heterocyclic compounds), preferably selected from fluazinam, pyrifenox, fenpropimorph, tridemorph and fenpropidin, in particular fenpropimorph.
  • group D heterocyclic compounds
  • the post-harvest treatment method comprises applying a further active compound Il selected from groups A') to F') as defined herein.
  • the post-harvest treatment method comprises applying as further active compound Il a compound selected from iprodione, dithianone or pyrimethanil.
  • the post-harvest treatment method comprises applying as compound I boscalid and as further active compound Il iprodione.
  • the post-harvest treatment method comprises applying as compound I epoxiconazole and as further active compound Il pyraclostrobin.
  • the post-harvest treatment method comprises applying as compound I pyraclostrobin and as further active compound Il boscalid. According to a further more preferred embodiment, the post-harvest treatment method comprises applying as compound I pyraclostrobin and no further active compound II.
  • the post-harvest treatment method comprises applying as compound I boscalid and as further active compound Il iprodione.
  • the post-harvest treatment method comprises applying as compound I pyrimethanil and as further active compound Il dithianon. According to a further more preferred embodiment, the post-harvest treatment method comprises applying as compound I fenpropimorph and as further active compound Il kresoxim-methyl.
  • the post-harvest treatment method wherein said harvested produce is a fruit, flower, nut or vegetable, is preferred.
  • the post-harvest treatment method wherein the harvested produce is a fruit or vegetable with inedible peel, preferably selected from avocados, bananas, plantains, lemons, grapefruits, melons, oranges, pineapples, kiwi fruits, guavas, mandarins, mangoes and pumpkin, is preferred, more preferarbly bananas, oranges, lemons and peaches, in particular bananas.
  • the post-harvest treatment method wherein the harvested produce is selected from avocadoes, bananas, plantains and citrus, is even more preferred.
  • the post-harvest treatment method wherein the harvested produce is a cut flower from ornamental plants, preferably selected from Alstroemeria, Carnation, Chrysanthemum, Freesia, Gerbera, Gladiolus, baby's breath (Gypsophila spec), Helianthus, Hydrangea, Lilium, Lisianthus, roses and summer flowers; in particular roses, is preferred.
  • ornamental plants preferably selected from Alstroemeria, Carnation, Chrysanthemum, Freesia, Gerbera, Gladiolus, baby's breath (Gypsophila spec), Helianthus, Hydrangea, Lilium, Lisianthus, roses and summer flowers; in particular roses, is preferred.
  • the post-harvest treatment according to the invention is important in the control of a multitude of fungi or molds on various harvested produce, such as fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; harvested produce from leguminous plants, such as lentils and peas; harvested produce from cucurbits, such as squashes, cucumber or melons; citrus fruits, such as oranges, lemons, grapefruits or mandarins; vegetables, such as asparagus, cabbages, onions, tomatoes, potatoes or paprika; harvested produce from lauraceous plants, such as avocados; bananas; table grapes; hop; turf.
  • fruits such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries
  • harvested produce from leguminous plants such as lentils and peas
  • the post-harvest treatment according to the invention is particularly important in the control of a multitude of fungi or molds on various harvested produce almonds, anise, apple, apricot, artichoke, arugula, asparagus, atemoya, avocado, baby corn, banana, beans, beet, bittermelon, black salsify, blackberry, blueberry, breadfruit, broccoli, Brussels sprout, cabbage, cactus fruit, caimito, calamondin, canistel, cantaloupe, carrot, cashew apple, cashew nuts, cauliflower, celeriac, celery, chard, chayote, cherimoya, cherry, chicory, Chinese cabbage, chive, Clementines, coconut, collard, corn, cranberry, cucumber, currant, custard apple, cut flowers, daikon, date, dewberry, dill, durian, eggplant, elderberry, endive, fennel, fig, flower bulbs, garlic, ginger, gooseberry, gran
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://www.bio.org/speeches/pubs/er/agrLproducts.asp).
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • the term "plant” refers to a cultivated plant.
  • the inventive post-harvest treatment methods are particularly suitable for controlling the following diseases in harvested produce: in pome fruits, such as apples and pears: blue mold, gray mold, anthracnose rot, lenticel spot, bitter rot, black rot, white rot, mucor rot, alternaria rot, cladosporium rot, pleospora rot, phomopsis rot, pink rot, side rot, sooty blotch, fly speck, brown rot, phy- tophthora rot; in stone fruits, such as apricot, cherry, nectarine, peach, plum and prune: brown rot, gray mold, rhizopus rot, mucor rot, blue mold, alternaria rot, cladosporium rot; in kiwifruit: botrytis rot, surface mold, alternaria rot, juice blotch, dothiorella rot, phom
  • the compounds I and compounds Il can be converted into customary types of agro- chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the composition type depends on the particular intended purpose; in each case, it should ensure a fine and uniform distribution of the compounds.
  • composition types are suspensions (SC, OD, FS), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which can be water-soluble or wettable, as well as gel formulations for the treatment of plant propagation materials such as seeds (GF).
  • composition types e. g. SC, OD, FS, WG, SG, WP, SP, SS, WS, GF
  • composition types such as DP, DS, GR, FG, GG and MG are usually used undiluted.
  • compositions are prepared in a known manner (cf. US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning: "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, S. 8-57 und ff. WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030, GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science (J.
  • compositions for post-harvest treatments may also comprise auxiliaries which are customary in agrochemical compositions.
  • auxiliaries are solvents, solid carriers, waxes, dispersants or emulsifiers (such as further solubilizers, protective colloids, surfactants and adhesion agents), organic and anorganic thickeners, bactericides, anti-freezing agents, anti- foaming agents, if appropriate colorants and tackifiers or binders (e. g. for seed treatment formulations).
  • Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e. g.
  • Solid carriers are mineral earths such as silicates, silica gels, talc, kaolins, limestone, lime, chalk, bole, loess, clays, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and prod- ucts of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silicates, silica gels, talc, kaolins, limestone, lime, chalk, bole, loess, clays, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulf
  • Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, such as ligninsoulfonic acid (Borresperse ® types, Borregard, Norway) phenolsulfonic acid, naphthalenesulfonic acid (Morwet ® types, Akzo Nobel, U.S.A.), dibutylnaphthalene- sulfonic acid (Nekal ® types, BASF, Germany), and fatty acids, alkylsulfonates, alkyl- arylsulfonates, alkyl sulfates, laurylether sulfates, fatty alcohol sulfates, and sulfated hexa-, hepta- and octadecanolates, sulfated fatty alcohol glycol ethers, further
  • methylcellulose g. methylcellulose
  • hydrophobically modified starches polyvinyl alcohols (Mowiol ® types, Clariant, Switzerland), polycarboxylates (Sokolan ® types, BASF, Germany), polyalkoxylates, polyvinyl- amines (Lupasol ® types, BASF, Germany), polyvinylpyrrolidone and the copolymers therof.
  • thickeners i. e. compounds that impart a modified flowability to compositions, i. e. high viscosity under static conditions and low viscosity during agitation
  • thickeners are polysaccharides and organic and anorganic clays such as Xanthan gum (Kelzan ® , CP Kelco, U.S.A.), Rhodopol ® 23 (Rhodia, France), Veegum ® (RT. Vanderbilt, U.S.A.) or Attaclay ® (Engelhard Corp., NJ, USA).
  • Bactericides may be added for preservation and stabilization of the composition.
  • suitable bactericides are those based on dichlorophene and benzyl- alcohol hemi formal (Proxel ® from ICI or Acticide ® RS from Thor Chemie and Kathon ® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide ® MBS from Thor Chemie).
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • anti-foaming agents examples include silicone emulsions (such as e. g. Silikon ® SRE, Wacker, Germany or Rhodorsil ® , Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, fluoroorganic compounds and mixtures thereof.
  • Suitable colorants are pigments of low water solubility and water-soluble dyes. Examples to be mentioned und the designations rhodamin B, C. I. pigment red 112, C. I. solvent red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols and cellulose ethers (Tylose ® , Shin-Etsu, Japan).
  • Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the compound I and compounds Il with at least one solid carrier.
  • Granules e. g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active substances to solid carriers.
  • solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e.
  • ammonium sulfate ammonium phosphate, ammonium nitrate, ureas
  • products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • composition types are: 1. Composition types for dilution with water i) Water-soluble concentrates (SL, LS)
  • Emulsions (EW, EO, ES)
  • compositions generally comprise between 0.001 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Methods for applying compositions on to harvested produce include dipping, immersing, spraying, coating, dusting and soaking application methods of the harvested produce.
  • the application forms and methods depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active compounds.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
  • the substances can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.
  • a wetter, tackifier, dispersant or emulsifier it is possible to prepare concentrates composed of active sub- stance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
  • the active substance concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.00001 to 10%, preferably from 0.001 to 1 % by weight of active substance.
  • the active substances may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply compositions comprising over 95% by weight of active substance, or even to apply the active substance without additives.
  • UUV ultra-low-volume process
  • the amounts applied are, depending on the kind of effect desired, between 0.01 g and 2.0 kg of active substance per ton of harvested produce.
  • oils, wetters, adjuvants, herbicides, bactericides, other fungicides and/or pesticides may be added to the active substances or the compositions comprising them, if appropriate not until immediately prior to use (tank mix).
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the post-harvest treatment methods according to the invention can also comprise applying other active substances, e. g. insecticides, bactericides or preservants or else, as pre-mix or, if appropriate, not until immeadiately prior to use (tank mix).
  • the weight ratio of compound I and compound Il generally depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 and particularly in the range of from 1 :10 to 10:1 , more particularly in the range of from 1 :5 to 5:1.
  • Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the compound I.
  • compositions comprising a compound I and a further active compound II
  • the compound I/compound Il ratio is advantageously chosen so as to produce a synergistic effect.
  • the term "synergstic effect" is understood to refer in particular to that defined by
  • compositions according to the invention can be shown by the tests described below.
  • Commercial products MENTOR BASF SE
  • OPERA BASF SE
  • BARDOS NEU SYNGENTA
  • CANTUS 50 WG BASF SE
  • BELLIS 38 WG BASF SE
  • MERTEC plus Imazalil for post harvest treatment were used as described below.
  • the concentrated products were diluted with water to be used at 1500 ppm (dilution factor 1 :667) or 2000 ppm (1 :500), and Latron B-1956 (0.25%) was added. Orange fruits were wounded before dipping into different treatments containing the active ingredients indicated below. After drying the fruits were inoculated with a spore suspension of Penicilium digitatum. The treated fruits were kept at 17 - 19°C. The disease incidences were evaluated 12 days after treatment. The dosages and the obtained results are shown below.
  • the concentrated products were diluted with water to be used at 1000 ppm (dilution factor 1 :1000), 1500 ppm (1 :667) or 2000 ppm (1 :500), and Latron B-1956 (0.25%) was added.
  • Peach fruits were wounded with needles before dipping into different treatments containing the active ingredients at the dose level indicated below. After drying the fruits were inoculated with a spore suspension of Monilinia fructicola. The treated fruits were kept 8 days in a cold room (5°C) for disease development. Then the fruits were moved out to room temperature, and all peaches were re-inoculated with Monilinia fructicola. The disease incidences were evaluated 15 days after treatment. The dosages and the obtained results are shown below.
  • Comparative example 5 Efficacy against post harvest disease complex crown rot on banana fruits caused by one or more of the following pathogens: Thielaviopsis para- doxa, Lasiodiplodia theobromae, Colletotrichum musae, Fusarium roseum and Deigh- toniella torulosa
  • the concentrated products were diluted with water to be used at the dose levels shown below and 12 g/L hydrated aluminium potassium sulfate (alum) was added.
  • 12 g/L hydrated aluminium potassium sulfate (alum) was added.
  • One Liter of this treatment solution containing the active ingredients at the dose level indicated below was used to treat 100 kg of banana.
  • the treated banana fruits were then kept in a humid chamber at 14 to 16°C and a relative humidity of about 90% for disease development caused by natural infection.
  • the disease incidences were evaluated up to 26 days after treatment.
  • the dosages and the obtained results are shown below.
  • the concentrated products were diluted with water to be used at the dose levels shown below and Silwet (0.015%) was added.
  • Rose flowers variety Orlando were cut in the field and afterwards dipped for 15 sec into 2 liters of different treatments (10 flowers per treatment) containing the active ingredients at the dose level indicated below.
  • the treated flowers were kept 7 days in a humid chamber at about 24°C and a relative humidity close to 100% for disease development caused by natural infection. After 7 days, the of fungal attack was visually assessed as % severity.
  • the dosages and the obtained results are shown below.

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  • Engineering & Computer Science (AREA)
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  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catching Or Destruction (AREA)
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Abstract

La présente invention concerne une méthode de traitement post-récolte pour la suppression d'une infestation biologique dans un produit récolté, ladite méthode comprenant l'application au produit récolté d'une composition comprenant un solvant ou un vecteur solide et un composé I conforme aux revendications et à la description.
PCT/EP2009/067294 2008-12-22 2009-12-16 Méthode de traitement post-récolte WO2010072634A2 (fr)

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WO2012022706A1 (fr) * 2010-08-17 2012-02-23 Bayer Cropscience Ag Utilisation de dérivés de n-phénylethylpyrazole carboxamide ou de sels de ceux-ci pour prolonger la durée de vie des fruits et des légumes
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CN102948421A (zh) * 2011-08-28 2013-03-06 深圳诺普信农化股份有限公司 一种含有氟啶胺的杀菌组合物
CN102986694A (zh) * 2012-12-28 2013-03-27 江苏龙灯化学有限公司 一种含有噻呋酰胺和克菌丹的杀菌组合物及其用途
CN103118539A (zh) * 2010-07-23 2013-05-22 石原产业株式会社 软腐病用防治剂及软腐病防治方法
CN103392719A (zh) * 2011-01-12 2013-11-20 陕西美邦农药有限公司 一种含有亚胺唑与甲氧基丙烯酸酯类化合物的杀菌组合物
CN103416411A (zh) * 2013-07-08 2013-12-04 中国中化股份有限公司 一种含有氟吗啉与有机铜的农药组合物
CN103461338A (zh) * 2012-06-07 2013-12-25 陕西美邦农药有限公司 一种含咪唑菌酮的杀菌组合物
CN103563916A (zh) * 2012-08-04 2014-02-12 南京华洲药业有限公司 一种含噻呋酰胺和噁唑菌酮的杀菌组合物及其应用
CN103918671A (zh) * 2014-04-15 2014-07-16 中国农业大学 一种含丁吡吗啉与氟环唑的杀菌组合物
CN103999867A (zh) * 2014-06-16 2014-08-27 江三涛 一种治疗黄瓜霜霉病与靶斑病混发的药物
CN104351211A (zh) * 2014-07-24 2015-02-18 安徽天舜生物科技有限公司 一种含有丁吡吗啉和肟菌酯的杀菌组合物
CN104604931A (zh) * 2015-01-21 2015-05-13 浙江泰达作物科技有限公司 一种联苯吡菌胺与异稻瘟净的杀菌组合物及其用途
CN104604881A (zh) * 2013-11-05 2015-05-13 南京华洲药业有限公司 一种含氟啶胺和丙硫菌唑的杀菌组合物及其应用
CN105325434A (zh) * 2014-08-11 2016-02-17 深圳诺普信农化股份有限公司 杀菌组合物
CN105707109A (zh) * 2014-12-01 2016-06-29 吕汰 一种马铃薯拌种剂
CN105766959A (zh) * 2016-04-26 2016-07-20 南京华洲药业有限公司 一种含吡唑萘菌胺和多菌灵的杀菌组合物及其应用
CN105851010A (zh) * 2016-04-26 2016-08-17 南京华洲药业有限公司 一种含吡唑萘菌胺和氟啶胺的杀菌组合物及其应用
CN106508931A (zh) * 2015-09-15 2017-03-22 南京华洲药业有限公司 一种含苯噻菌胺和噻呋酰胺的杀菌组合物及其应用
CN108029749A (zh) * 2017-12-06 2018-05-15 宁波市农业科学研究院 一种水蜜桃贮藏保鲜方法
WO2019147561A1 (fr) * 2018-01-23 2019-08-01 Arysta Lifescience Inc. Procédé de lutte contre l'anthracnose sur des plants de fruits tropicaux
CN110573016A (zh) * 2017-05-04 2019-12-13 江苏龙灯化学有限公司 杀真菌组合物及其用途

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