WO2010069763A2 - Mélanges fongicides synergiques - Google Patents

Mélanges fongicides synergiques Download PDF

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Publication number
WO2010069763A2
WO2010069763A2 PCT/EP2009/066190 EP2009066190W WO2010069763A2 WO 2010069763 A2 WO2010069763 A2 WO 2010069763A2 EP 2009066190 W EP2009066190 W EP 2009066190W WO 2010069763 A2 WO2010069763 A2 WO 2010069763A2
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WO
WIPO (PCT)
Prior art keywords
methyl
phenyl
chloro
pyrazole
carboxamide
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PCT/EP2009/066190
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English (en)
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WO2010069763A3 (fr
WO2010069763A9 (fr
Inventor
Markus Gewehr
Jochen Dietz
Thomas Grote
Thorsten Jabs
Egon Haden
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Basf Se
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Priority to CN2009801506037A priority Critical patent/CN102256492A/zh
Priority to EP09764503A priority patent/EP2378882A2/fr
Priority to BRPI0917760-4A priority patent/BRPI0917760A2/pt
Publication of WO2010069763A2 publication Critical patent/WO2010069763A2/fr
Publication of WO2010069763A3 publication Critical patent/WO2010069763A3/fr
Publication of WO2010069763A9 publication Critical patent/WO2010069763A9/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
    • 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

Definitions

  • the present invention relates to mixtures comprising, as active components
  • carboxamides 5 - carboxanilides benalaxyl, benalaxyl-M, benodanil, carboxin, fenfuram, fen- hexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, 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-pyr-
  • triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenocona- zole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, my- clobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothio- conazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triti— conazole, uniconazole, 1-(4-chloro-phenyl)-2-([1 ,2,4]triazol-1-yl)-cycloheptanol; imidazo
  • 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, S ⁇ -trichloropyridine ⁇ . ⁇ -di-carbo- nitrile, 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, diflumetorim, fenari
  • 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, iproben- fos, phosphorous acid and its salts,
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dike- gulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-
  • acetamides acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufen- acet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor; amino acid derivatives: bilanafos, glyphosate, glufosinate, sulfosate; - aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
  • Bipyridyls diquat, paraquat;
  • (thio)carbamates asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributi- carb, thiobencarb, triallate; cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim; - dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, triflu- ralin; diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen; hydroxybenzonitriles:
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methi- dathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimi- phos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazo- phos, trichlorfon; carbamates: alanycar
  • METI Il and III compounds acequinocyl, fluacyprim, hydramethylnon;
  • Uncouplers chlorfenapyr; oxidative phosphorylation inhibitors: cyhexatin, diafenthiuron, fenbutatin oxide, propargite; moulting disruptor compounds: cryomazine; mixed function oxidase inhibitors: piperonyl butoxide; - sodium channel blockers: indoxacarb, metaflumizone; others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr (HGW86), cyenopyrafen, flu- pyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, and pyrifluquinazon;
  • the invention relates also to a method for controlling phytopathogenic harmful fungi using mixtures of a compound I and at least one active compound Il and to the use of compound I and compounds Il for preparing such mixtures, and to com- positions and seed comprising these mixtures.
  • compositions which, at a reduced total amount of active compounds applied, have improved activity against the harmful fungi (synergistic mixtures) and a broadened activty spectrum, in particular for certain indications.
  • Compound I has a center of chirality and is present as pure (E)- or (Z)-isomer or as isomer mixtures. Both, the pure isomer and their mixtures are in mixture with at least one active compound Il subject matter of the present invention. Moreover, we have found that simultaneous, that is joint or separate, application of compound I and at least one compound Il or successive application of a compound I and of a compound Il allows better control of harmful fungi than is possible with the individual compounds alone (synergistic mixtures). Furthermore, synergistic effects in relation with the insecticidal and/or herbicidal action has been found with the inventive mixtures.
  • Compound I and/or the compounds Il of the inventive compositions can be present in different crystal modifications, which may differ in biological activity.
  • Compund I (3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1 -morpholin-4-yl-prope- none, also called pyrimorph) and its fungicidal activity has been described in CN 1939128.
  • 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 (DE 23 24 020), bromuconazole, 1 -[[4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl]methyl]-1 H-
  • 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
  • flubenthiavalicarb (benthiavalicarb), isopropyl ⁇ (S)-1-[(1 R)-1-(6-fluorobenzothiazol-2-yl)- ethylcarbamoyl]-2-methylpropyl ⁇ carbamate (JP-A 09/323 984); carpropamid, 2,2-dichloro-N-[1 -(4-chlorphenyl)ethyl]-1 -ethyl-3-methylcyclopropane- carboxamide [CAS RN 104030-54-8]; chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3 290 353); cyflufenamid, (Z)-N-[ ⁇ -(cyclopropylmethoxyimino ⁇ .S-difluoro- ⁇ - ⁇ rifluoromethylJben- zyl]-2-phenylacetamide (WO 96/19
  • orysastrobin (2E)-2-(methoxyimino)-2- ⁇ 2-[(3E,5E,6E)-5-(methoxyimino)-4,6-dimethyl- 2,8-dioxa-3,7-diazanona-3,6-dien-1 -yl]phenyl ⁇ -N-methylacetamide (WO 97/15552); picoxystrobin, methyl 3-methoxy-2-[2-(6-trifluoromethylpyridin-2-yloxymethyl)phenyl]- acrylate (EP 278 595); pyraclostrobin, methyl N- ⁇ 2-[1-(4-chlorophenyl)-1 H-pyrazol-3-yloxymethyl]phenyl ⁇ (N- methoxy)carbamate (WO 96/01256); trifloxystrobin, methyl (E)-methoxyimino- ⁇ (E)- ⁇ -[1-( ⁇ , ⁇ , ⁇
  • the mixtures comprise as compound Il a compound that is selected from the group A), C), D), E), F) and G).
  • mixtures comprise as compound Il a compound that is selected from the group H). According to a further embodiment, mixtures comprise as compound Il a compound that is selected from the group I).
  • mixtures comprise as compound Il a compound of group A (strobilurins), preferably selected from pyraclostrobin, kresoxim-methyl, azoxystrobin, trifloxystrobin, enestroburin and pyribencarb.
  • group B) of compounds Il is as follows:
  • - carboxanilides benalaxyl, benalaxyl-M, benodanil, carboxin, penthiopyrad, boscalid, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, , teclof- talam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro- N-(1,1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-[2-(1 ,1,2,3,3,3-hexafluoropropoxy)- phenyl]-3-difluoromethyl-1-methyl-1 H-pyrazole
  • - benzoic acid amides flumetover, fluopicolde, fluopyram, zoxamide, N-(3-ethyl- 3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide;
  • - other carboxamides carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
  • mixtures comprise as compound Il a compound of group B (carboxamides), preferably selected from fluopyram, mandiproamid, amisul- brom, flutolanil, metalaxyl, oxadixyl, benalaxyl, ofurace, dimethomorph, zoxamide and flumetover.
  • group B carboxyamides
  • mixtures comprise as compound Il a compound of group C (azoles), preferably selected from epoxiconazole, prochloraz, ethaboxam, benomyl, carbendazim, thiabendazole, difenoconazole, flusilazole, tebuconazol, cypro- conazole, prothioconazole and 1-(4-chloro-phenyl)-2-([1 ,2,4]triazol-1-yl)-cycloheptanol.
  • group C azoles
  • mixtures comprise as compound Il a compound of group D (heterocyclic compounds), preferably selected from famoxadone, fenami- done, folpet, captan and 5-amino-2-isopropyl-3-oxo-4-o-tolyl-2,3-dihydro-pyrazole-
  • mixtures comprise as compound Il a compound of group E (carbamates), preferably selected from mancozeb, maneb, metiram, thiram, zineb, propineb, ziram, phosphorous acid, fentin acetate, iprovalicarb, valiphenal, ben- thiavalicarb and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4- fluorophenyl.
  • group E carbamic acid-(4- fluorophenyl.
  • mixtures comprise as compound Il a compound of group F (other active substances), preferably selected from cymoxanil, thiophanate- methyl, fosetyl, chlorothalonil, copper, copper hydroxide and copper oxychloride.
  • group F other active substances
  • E3 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1 -mor- pholin-4-yl-propenone and trifloxystrobin.
  • E4) Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and enestroburin.
  • E5 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1 -mor- pholin-4-yl-propenone and pyribencarb.
  • E6 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1 -mor- pholin-4-yl-propenone and kresoxim-methyl.
  • E7) Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1 -mor- pholin-4-yl-propenone and fluoxastrobin.
  • E8) Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and famoxadone.
  • E1 1 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and 2-(ortho-((2,5-Dimethylphenyl-oxymethylen)phenyl)-3- methoxy-acrylsauremethylester.
  • E12 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and mancozeb.
  • E16 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and thiram.
  • E17 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and zineb.
  • E21 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and phosphorous acid.
  • E22 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and fosetyl-aluminium.
  • E30 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and thiophanate-methyl.
  • E31 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and carbendazim.
  • E35 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and difenoconazole.
  • E36 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and flusilazol.
  • E40 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and flutolanil.
  • E41 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and iprovalicarb.
  • E57 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and 1 -(4-chloro-phenyl)-1 -(propin-2-yl-oxy)-3-(4-(3,4-dimethoxy- phenyl)-isoxazol-5-yl)-propan-2-one.
  • E58 Synergistic mixtures of 3-(4-tert.-butyl-phenyl)-3-(2-chloro-pyridin-4-yl)-1-mor- pholin-4-yl-propenone and copper.
  • the mixtures and compositions according to the invention are suitable as fungi- cides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the mixtures and compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • cereals e. g. wheat, rye, barley, triticale, oats or rice
  • beet e. g. sugar beet or fodder beet
  • fruits such as pomes, stone fruits or soft fruits, e. g.
  • inventive mixtures and compositions are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • treatment of plant propagation materials with the inventive combination of compound I and compounds Il and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • 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.
  • HPPD hydroxyphenylpyruvate dioxygenase
  • ALS acetolactate synthase
  • WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imida- zolinones see e. g. US 6,222,100, WO 01/82685, WO 00/026390, WO 97/41218, WO 98/002526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/014357, WO 03/13225, WO 03/14356, WO 04/16073
  • EPSPS enolpyruvylshikimate-3-phosphate syn- thase
  • GS glutamine synthetase
  • GS glutamine synthetase
  • glufosinate see e.g. EP-A 242 236, EP-A 242 246) or oxynil herbicides (see e. g. US 5,559,024)
  • mutagenesis e.g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ - endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi) or Cry9c; vegetative insecticidal proteins (VIP), e. g. Vl P1 , Vl P2, Vl P3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • VIP vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomy- cetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibi- tors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as block
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the per- son skilled in the art and are described, e. g.
  • insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • YieldGard ® (com cultivars producing the CryiAb toxin), YieldGard ® Plus (corn cultivars producing CryiAb and Cry3Bb1 toxins), Starlink ® (corn cultivars producing the Cry9c toxin), Her- culex ® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphi- nothricin-N-Acetyltransferase [PAT]); NuCOTN ® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard ® I (cotton cultivars producing the CryiAc toxin), Bollgard ® Il (cotton cultivars producing CryiAc and Cry2Ab2 toxins); VIPCOT ® (cotton cultivars producing a VIP-toxin); NewLeaf ® (potato cultivars producing the Cry3A
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CryiAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or toler- ance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of syn- thesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lysozym e.
  • plants are also covered that are by the use of recombinant DNA tech- niques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
  • the inventive mixtures and compositions are particularly suitable for controlling the following plant diseases:
  • Albugo spp. white rust
  • vegetables e. g. A. Candida
  • sunflowers e. g. A. tragopogonis
  • Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassi- cae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alter- nata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables;
  • Ascochyta spp. on cereals and vegetables e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.) on com (e. g. D. maydis), cereals (e. g. B. sorokiniana: spot blotch), rice (e. g. B. oryzae) and turfs;
  • Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce;
  • Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn, rice, sugar beets (e. g. C. beti- cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice;
  • Cladosporium spp. on tomatoes e. g. C. fulvum: leaf mold
  • cereals e. g. C. herbarum (black ear) on wheat;
  • Colletotrichum teleomorph: Glomerella
  • spp. anthracnose
  • cotton e. g. C. gos- sypii
  • corn e. g. C. graminicola
  • soft fruits e. g. C. coccodes: black dot
  • beans e. g. C. lindemuthianum
  • soybeans e. g. C. truncatum or C. gloeo- sporioides
  • Corticium spp. e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nec- tria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals;
  • Cylindrocarpon spp. e. g. fruit tree canker or young vine decline, teleomorph: Nec- tria or Neonectria spp.
  • vines e. g. C. liriodendri, teleo
  • Dematophora teleomorph: Rosellinia necatrix (root and stem rot) on soybeans; Di- aporthe spp., e. g. D. phaseolorum (damping off) on soybeans;
  • Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F.
  • Phaeomoniella chlamydospora (earlier Phaeoacremonium chla- mydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa
  • Elsinoe spp. on pome fruits E. pyri
  • soft fruits E. veneta: anthracnose
  • vines E. ampe- lina: anthracnose
  • Entyloma oryzae leaf smut
  • Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. crucife- rarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods;
  • Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticil- lioides on corn;
  • Gaeumannomyces graminis take-all on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton;
  • Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice;
  • Hemileia spp. e. g. H. vastatrix (coffee leaf rust) on coffee; lsariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton;
  • Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley);
  • Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants;
  • M. graminicola anamorph: Septoria tritici, Septoria blotch
  • M. fijiensis black Sigatoka disease
  • Peronospora spp. downy mildew on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans;
  • Phialophora spp. e. g. on vines e. g. P. tracheiphila and P. tetraspora
  • soybeans e. g. P. gregata: stem rot
  • Phoma lingam root and stem rot
  • P. betae root rot, leaf spot and damping-off
  • sugar beets Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn;
  • Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death);
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • Podosphaera spp. powdery mildew on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples;
  • Polymyxa spp. e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases;
  • Pseudocercosporella herpotrichoides eyespot, teleomorph: Tapesia yallundae
  • cereals e. g. wheat or barley
  • Pseudoperonospora downy mildew
  • various plants e. g. P. cubensis on cucurbits or P. humili on hop;
  • Puccinia spp. rusts on various plants, e. g. P. triticina (brown or leaf rust), P. strii- formis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, and asparagus (e. g. P. asparagi);
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis tan spot
  • P. teres net blotch
  • Pyricularia spp. e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals;
  • Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphani- dermatum);
  • Ramularia spp. e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets;
  • Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley;
  • Rhizopus stolonifer black mold, soft rot on strawberries, carrots, cabbage, vines and tomatoes;
  • Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. scle- rotiorum);
  • Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals;
  • Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines;
  • Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf;
  • Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits;
  • Stagonospora spp. on cereals e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease);
  • Taphrina spp. e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums;
  • Thielaviopsis spp. black root rot
  • tobacco, pome fruits, vegetables, soybeans and cotton e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn.
  • Uromyces spp. rust on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), com (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
  • beans e. g. U. appendiculatus, syn. U. phaseoli
  • sugar beets e. g. U. betae
  • the inventive mixtures and compositions are also suitable for controlling harmful fungi in the protection of materials (e. g. wood, paper, paint dispersions, fiber or fabrics) and in the protection of stored products or for post harvest treatment of harvest.
  • materials e. g. wood, paper, paint dispersions, fiber or fabrics
  • harmful fungi Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Candida spp. and Saccharomyces cerevisae are noteworthy of note: Candida spp. and Saccharomyces cerevisae.
  • mixtures and compositions of the present invention are effective against plant pathogens in speciality crops such as vine, fruits, hop, vegetables and tabacco - see the above list.
  • Plant propagation materials may be treated with the mixtures and compositions of the invention prophylactically either at or before planting or transplanting.
  • the present invention also relates to a pesticidal agent comprising at least one solid or liquid carrier and a composition as described herein.
  • the compound I and compounds II, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspen- sions, dusts, powders, pastes and granules.
  • agrochemical compositions e. g. solutions, emulsions, suspen- sions, 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 compound according to the invention.
  • 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.
  • the compositions are prepared in a known manner (cf. US 3,060,084,
  • the agrochemical compositions may also comprise auxiliaries which are customary in agrochemical compositions.
  • auxiliaries depend on the particular application form and active substance, respectively.
  • auxiliaries are solvents, solid carriers, dispersants or emulsifi- ers (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 me- dium 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 products 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 sulfate, ammonium phosphat
  • 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,
  • aromatic sulfonic acids such as ligninsoulfonic acid (Borresperse
  • 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.
  • suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • anti-foaming agents are silicone emulsions (such as e. g. Silikon ®
  • 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 examples include polyvinylpyrrolidone, 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:
  • composition types for dilution with water i) Water-soluble concentrates (SL, LS)
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • the composition has an active sub- stance content of 25% by weight, v) Suspensions (SC, OD, FS)
  • Dilution with water gives a stable dispersion or solution of the active substance.
  • the composition has an active substance content of 50% by weight, vii) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of of active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • the active substance content of the composition is 75% by weight, viii) Gel (GF)
  • the agrochemical compositions generally comprise between 0.01 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).
  • Water-soluble concentrates (LS), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES) emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • These compositions can be applied to plant propagation materials, particularly seeds, diluted or undiluted.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before sowing.
  • Methods for applying or treating agrochemical compounds and compo- sitions thereof, respectively, on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting, dusting and soaking application methods of the propagation material.
  • the compounds or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • a suspension-type (FS) composition is used for seed treatment.
  • a FS composition may comprise 1-800 g/l of active substance, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • the active substances can be used as such or in the form of their compositions, e. g.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.
  • concentrates composed of active substance, 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 0.0001 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 proc- ess (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 proc- ess
  • the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active substance per ha.
  • active substance In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 1 to 1000 g, preferably from 5 to 100 g, per 100 kilogram of seed are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are, e. g., 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • 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.
  • Adjuvants which can be used are in particular organic modified polysiloxanes such as Break Thru S 240 ® ; alcohol alkoxylates such as Atplus 245 ® , Atplus MBA 1303 ® , Plurafac LF 300 ® and Lutensol ON 30 ® ; EO/PO block polymers, e. g. Pluronic RPE 2035 ® and Genapol B ® ; alcohol ethoxylates such as Lutensol XP 80 ® ; and dioctyl sulfo- succinate sodium such as Leophen RA ® .
  • organic modified polysiloxanes such as Break Thru S 240 ®
  • alcohol alkoxylates such as Atplus 245 ® , Atplus MBA 1303 ® , Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO/PO block polymers e. g. Pluronic RPE 2035 ® and Genapol B ®
  • compositions according to the invention can, in the use form as fungicides, also be present together with other active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immeadiately prior to use (tank mix).
  • active substances e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immeadiately prior to use (tank mix).
  • the harmful fungi to be controlled or their habitats such as infected plants, plant propagation materials, particularly seeds, surfaces, materials or the soil as well as plants, plant propagation materials, particularly seeds, soil, surfaces, materials or rooms to be protected from fungal attack) in an effective amount.
  • This can be obtained by applying compound I and compound Il simultaneously, either jointly (e. g. as tank-mix) or separately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s).
  • the order of application is not essential for working of the present invention.
  • the weight ratio of compound I and compound Il generally depends from the properties of the active sub- stances 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.
  • any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the compound I.
  • the compound I/compound Il ratio is advantageously chosen so as to produce a synergistic effect.
  • the components can be used individually or already partially or completely mixed with one another to prepare the composition according to the invention. It is also possible for them to be packaged and used further as combination composition such as a kit of parts.
  • kits may include one or more, including all, components that may be used to prepare a subject agrochemical composition.
  • kits may include one or more fungicide component(s) and/or an adjuvant component and/or a insecticide component and/or a growth regulator component and/or a her- bicde.
  • One or more of the components may already be combined together or pre- formulated.
  • the components may already be combined together and as such are packaged in a single container such as a vial, bottle, can, pouch, bag or canister.
  • two or more components of a kit may be packaged separately, i. e., not pre- formulated.
  • kits may include one or more separate containers such as vials, cans, bottles, pouches, bags or canisters, each container containing a separate component for an agrochemical composition.
  • a component of the kit may be applied separately from or together with the further components or as a component of a combination composition according to the invention for preparing the composition according to the invention.
  • the user applies the composition according to the invention usually from a predos- age device, a knapsack sprayer, a spray tank or a spray plane.
  • the agrochemical composition is made up with water and/or buffer to the desired application concentration, it being possible, if appropriate, to add further auxiliaries, and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 50 to 500 liters of the ready-to-use spray liquor are applied per hectare of agricultural useful area, preferably 100 to 400 liters.
  • individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate (tank mix).
  • either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate (tank mix).
  • either individual components of the composition according to the invention or partially premixed components can be applied jointly (e. .g. after tankmix) or consecutively.
  • compositions according to the invention can be shown by the tests described below.
  • the active compounds are prepared as a stock solution comprising 25 mg of active compound which is made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol ® EL (wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols) in a ratio by volume of solvent/emulsifier of 99:1.
  • the mixture is then made up to 100 ml with water.
  • This stock solution is diluted with the solvent/emulsifier/water mixture described to give the concentration of active compound stated below.
  • ⁇ corresponds to the fungicidal infection of the treated plants in % and ⁇ corresponds to the fungicidal infection of the untreated (control) plants in %
  • An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
  • the active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • the stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • MTP micro titer plate
  • a spore suspension of of the respective fungal pathogen in an aqueous biomalt solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
  • the measured parameters were compared to the growth of the active compound- free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies.
  • An efficacy of 0 means that the growth level of the pathogens corresponds to that of the untreated control; an efficacy of 100 means that the pathogens were not growing.
  • E expected efficacy expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b x efficacy, expressed in % of the untreated control, when using the active compound A at the concentration a y efficacy, expressed in % of the untreated control, when using the active compound B at the concentration b.
  • Use example 1 Activity against the grey mold Botrytis cinerea in the microtiterplate test A spore suspension of Botrytis cinerea was used.
  • Use example 2 Activity against rice blast Pyricularia oryzae in the microtiterplate test A spore suspension of Pyricularia oryzae was used.
  • Use example 3 Activity against rice blast Fusarium culmorum in the microtiterplate test A spore suspension of Fusarium culmorum was used.
  • Use example 4 Activity against rice blast Pyrenophora teres in the microtiterplate test A spore suspension of Pyrenophora teres was used.

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

Abstract

La présente invention porte sur un mélange, comprenant une 3-(4-tert.-butyl-phényl)-3-(2-chloro-pyridin-4-yl)-1-morpholin-4-yl-propénone et au moins un composé actif II choisi dans les groupes A) à I) comme défini dans la description dans une quantité efficace de façon synergétique, et sur des compositions comprenant ces mélanges.
PCT/EP2009/066190 2008-12-16 2009-12-02 Mélanges fongicides synergiques WO2010069763A2 (fr)

Priority Applications (3)

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CN2009801506037A CN102256492A (zh) 2008-12-16 2009-12-02 协同增效杀真菌混合物
EP09764503A EP2378882A2 (fr) 2008-12-16 2009-12-02 Mélanges fongicides synergiques
BRPI0917760-4A BRPI0917760A2 (pt) 2008-12-16 2009-12-02 Mistura, composição agroquímica, método para controlar fungos nocivos fitopatogênicos, semente e processo para preparar uma composição

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CN101946786A (zh) * 2010-10-27 2011-01-19 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101953349A (zh) * 2010-10-27 2011-01-26 陕西汤普森生物科技有限公司 一种含丁吡吗啉与氰霜唑的杀菌组合物
CN101961020A (zh) * 2010-10-27 2011-02-02 陕西汤普森生物科技有限公司 一种含丁吡吗啉与多抗霉素的杀菌组合物
CN101961024A (zh) * 2010-10-27 2011-02-02 陕西汤普森生物科技有限公司 一种含丁吡吗啉与异菌脲的杀菌组合物
CN101965845A (zh) * 2010-10-27 2011-02-09 陕西汤普森生物科技有限公司 一种含丁吡吗啉与霜脲氰的杀菌组合物
CN101965844A (zh) * 2010-10-27 2011-02-09 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101971826A (zh) * 2010-10-27 2011-02-16 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101971838A (zh) * 2010-10-27 2011-02-16 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101971827A (zh) * 2010-10-27 2011-02-16 陕西汤普森生物科技有限公司 一种含丁吡吗啉与双炔酰菌胺的杀菌组合物
CN102047887A (zh) * 2010-12-06 2011-05-11 潍坊先达化工有限公司 一种除草剂组合物
WO2012070961A3 (fr) * 2010-11-26 2012-08-02 Sapec-Agro, Sa Mélange fongicide
CN102919254A (zh) * 2010-12-08 2013-02-13 陕西美邦农药有限公司 一种含十三吗啉的杀菌组合物
CN103109825A (zh) * 2013-01-27 2013-05-22 成都科利隆生化有限公司 苯噻菌胺和嘧菌酯农药组合物
EP2608795A1 (fr) 2010-08-26 2013-07-03 Makhteshim Chemical Works Ltd. Composition fongicide synergétique
CN103478152A (zh) * 2012-06-14 2014-01-01 陕西美邦农药有限公司 一种含咪唑菌酮的杀菌组合物
CN103931628A (zh) * 2011-04-27 2014-07-23 陕西汤普森生物科技有限公司 一种含有啶氧菌酯与酰胺类的农药组合物
CN106259410A (zh) * 2016-08-08 2017-01-04 苏州莱奥生物技术有限公司 一种植物杀虫组合物
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests

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CN103300017A (zh) * 2012-03-14 2013-09-18 陕西汤普森生物科技有限公司 一种含有丁吡吗啉的杀菌组合物
CN103907605A (zh) * 2012-12-31 2014-07-09 江苏丰登农药有限公司 一种含啶酰菌胺和联苯吡菌胺的复合增效杀菌组合物及其应用
CN103360170A (zh) * 2013-07-25 2013-10-23 常熟市新靓文辅亚农艺发展有限公司 除草杀虫剂
CN103503886A (zh) * 2013-10-16 2014-01-15 赵邦斌 一种含丁吡吗啉的复配杀菌剂
CN104322549B (zh) * 2013-11-21 2015-12-30 海南正业中农高科股份有限公司 含有吡氟硫磷与多杀菌素的农药组合物
CN103918659B (zh) * 2014-04-11 2016-01-27 柳州市惠农化工有限公司 一种含唑虫酰胺和氟啶胺的农药组合物及其制备方法和用途
CN103918670B (zh) * 2014-04-15 2015-09-23 中国农业大学 一种含丁吡吗啉与啶酰菌胺的杀菌组合物
CN104304272B (zh) * 2014-09-25 2016-11-23 南京华洲药业有限公司 一种包括氯酯磺草胺与异恶草松的混合除草剂及制备方法
CN108013057A (zh) * 2017-12-15 2018-05-11 北京科发伟业农药技术中心 一种含唑啉草酯的除草组合物
CN109258653B (zh) * 2018-11-06 2021-11-09 赣南师范大学 一种丁吡吗啉与抑霉唑的杀菌复配组合物及其应用
CN111056603A (zh) * 2019-12-17 2020-04-24 宁波市川宁环保科技有限公司 一种循环水高效广谱杀菌剂
CN115530172B (zh) * 2022-09-08 2024-04-05 中国农业大学 一种含有丁吡吗啉的杀菌组合物

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EP2608795A1 (fr) 2010-08-26 2013-07-03 Makhteshim Chemical Works Ltd. Composition fongicide synergétique
MD4555B1 (ro) * 2010-08-26 2018-03-31 Adama Makhteshim Ltd. Compoziţie fungicidă şi procedeu de tratare a plantelor
CN101971826B (zh) * 2010-10-27 2013-08-14 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101946786A (zh) * 2010-10-27 2011-01-19 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101965845A (zh) * 2010-10-27 2011-02-09 陕西汤普森生物科技有限公司 一种含丁吡吗啉与霜脲氰的杀菌组合物
CN101965844A (zh) * 2010-10-27 2011-02-09 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101971826A (zh) * 2010-10-27 2011-02-16 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101971838A (zh) * 2010-10-27 2011-02-16 陕西汤普森生物科技有限公司 一种含丁吡吗啉的杀菌组合物
CN101971827A (zh) * 2010-10-27 2011-02-16 陕西汤普森生物科技有限公司 一种含丁吡吗啉与双炔酰菌胺的杀菌组合物
CN101953349A (zh) * 2010-10-27 2011-01-26 陕西汤普森生物科技有限公司 一种含丁吡吗啉与氰霜唑的杀菌组合物
CN101961024A (zh) * 2010-10-27 2011-02-02 陕西汤普森生物科技有限公司 一种含丁吡吗啉与异菌脲的杀菌组合物
CN101961020A (zh) * 2010-10-27 2011-02-02 陕西汤普森生物科技有限公司 一种含丁吡吗啉与多抗霉素的杀菌组合物
WO2012070961A3 (fr) * 2010-11-26 2012-08-02 Sapec-Agro, Sa Mélange fongicide
CN102047887B (zh) * 2010-12-06 2013-07-31 潍坊先达化工有限公司 一种除草剂组合物
CN102047887A (zh) * 2010-12-06 2011-05-11 潍坊先达化工有限公司 一种除草剂组合物
CN102919254A (zh) * 2010-12-08 2013-02-13 陕西美邦农药有限公司 一种含十三吗啉的杀菌组合物
CN103931628A (zh) * 2011-04-27 2014-07-23 陕西汤普森生物科技有限公司 一种含有啶氧菌酯与酰胺类的农药组合物
CN103478152A (zh) * 2012-06-14 2014-01-01 陕西美邦农药有限公司 一种含咪唑菌酮的杀菌组合物
CN103478152B (zh) * 2012-06-14 2017-02-15 陕西美邦农药有限公司 一种含咪唑菌酮的杀菌组合物
CN103109825A (zh) * 2013-01-27 2013-05-22 成都科利隆生化有限公司 苯噻菌胺和嘧菌酯农药组合物
CN106259410A (zh) * 2016-08-08 2017-01-04 苏州莱奥生物技术有限公司 一种植物杀虫组合物
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests

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WO2010069763A3 (fr) 2011-04-14
EP2378882A2 (fr) 2011-10-26
WO2010069763A9 (fr) 2011-06-16
CN102256492A (zh) 2011-11-23

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