WO2011026796A1 - Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi - Google Patents

Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi Download PDF

Info

Publication number
WO2011026796A1
WO2011026796A1 PCT/EP2010/062565 EP2010062565W WO2011026796A1 WO 2011026796 A1 WO2011026796 A1 WO 2011026796A1 EP 2010062565 W EP2010062565 W EP 2010062565W WO 2011026796 A1 WO2011026796 A1 WO 2011026796A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
yl
chloro
phenyl
acid
Prior art date
Application number
PCT/EP2010/062565
Other languages
French (fr)
Inventor
Markus Frank
Thorsten Jabs
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP09169127.9 priority Critical
Priority to EP09169127 priority
Application filed by Basf Se filed Critical Basf Se
Publication of WO2011026796A1 publication Critical patent/WO2011026796A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, 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
    • A01N37/36Biocides, 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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids

Abstract

The present invention relates to mixtures comprising compounds I and compounds II as defined in the description and methods, use and compositions for combating phytopathogenic fungi in plants using these mixtures.

Description

Synergistic fungicidal mixtures comprising lactylates and method for combating phyto- pathogenic fungi

Description

The present invention relates to a mixture, comprising as active compounds

1 ) at least one compound of formula I

Figure imgf000002_0001

wherein

Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms, wherein the carbon chain is branched or unbranched,

X is H or CHs; n is an integer with a value of 1 to 10;

A is, if n > 1 , -CO-, or,

A is, if n = 1 , -CO- or a direct bond; or an agrochemically acceptable salt thereof,

and

2) at least one active compound II selected from groups A) to I): A) strobilurins

azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, me- tominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-(2-(6-(3-chloro-2-methyl-phen- oxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methyl-acetamide, 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane-carboximidoyl- sulfanylmethyl)-phenyl)-acrylic acid methyl ester, methyl (2-chloro-5-[1 -(3- methylbenzyloxyimino)ethyl]benzyl)carbamate and 2-(2-(3-(2,6-di- chlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino- N-methyl-acetamide;

B) carboxamides

- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino- 4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)- nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H- pyrazole-4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)- 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3- trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;

- carboxylic morpholides: dimethomorph, flumorph, pyrimorph;

- benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N-(3- Ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide;

- other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;

C) azoles

- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenocona- zole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquin- conazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -(4-chloro-phenyl)-2- ([1 ,2,4]triazol-1 -yl)-cycloheptanol;

- imidazoles: cyazofamid, imazalil, pefurazoate, prochloraz, triflumizol;

- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

- others: ethaboxam, etridiazole, hymexazole and 2-(4-chloro-phenyl)-N-[4-(3,4- dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;

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, diflumetorim, fenarimol, ferimzone, mepani- pyrim, nitrapyrin, nuarimol, pyrimethanil;

- piperazines: triforine;

- pyrroles: fenpiclonil, fludioxonil;

- morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;

- piperidines: fenpropidin;

- dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;

- non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro- pyrazole-1 -carbothioic acid S-allyl ester; - others: acibenzolar-S-methyl, ametoctradin, amisulbrom, anilazin, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzo- quat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, pro- quinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3- propylchromen-4-one, 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H- benzoimidazole and 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6- trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine;

E) carbamates

- thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulpho- carb, metiram, propineb, thiram, zineb, ziram;

- carbamates: benthiavalicarb, diethofencarb, iprovalicarb, propamocarb,

propamocarb hydrochlorid, valifenalate and N-(1 -(1 -(4-cyano-phenyl)- ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;

F) other active substances

- 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, ipro- benfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;

- organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusul- famide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfonamide;

- inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

- others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamin,

metrafenone, mildiomycin, oxin-copper, prohexadione-calcium, spiroxamine, tebufloquin, tolylfluanid, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3- difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(4-(4-fluoro- 3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N- methyl formamidine, N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine,

2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-amide, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen-1 -yl-amide, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N- Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-

N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4-thiazolecarboxamide;

G) growth regulators

abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, flu- thiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohy- drojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,

2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;

H) herbicides

- acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, 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, pyributicarb, thiobencarb, triallate;

- cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxy- dim, tepraloxydim, tralkoxydim;

- dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;

- diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;

- hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;

- imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;

- phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4- DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;

- pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate;

- pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;

- sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flu- cetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodo- sulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, ox- asulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometu- ron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 -((2-chloro-6-propyl-imidazo[1 ,2-b]pyridazin-3- yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)urea;

- triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, tri- aziflam;

- ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron,

methabenzthiazuron,tebuthiuron;

- other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho- sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyriben- zoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;

- others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, ben- carbazone,benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopy- rone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentra- zone, cinidon-ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosul- famide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pen- toxazone, pinoxaden, pyraclonil, pyraf I uf en-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro- 5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1 -yl)- phenoxy]-pyridin-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2- cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2- cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4-chloro- phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-

3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2-carboxylic acid methyl ester;

I) insecticides

- organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyri- fos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;

- carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofu- ran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;

- pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cyperme- thrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda- cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;

- insect growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorflua- zuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spi- romesifen, spirotetramat;

- nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -(2-chloro- thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;

- GABA antagonist compounds: endosulfan, ethiprole, fipronil, vaniliprole, pyra- fluprole, pyriprole, 5-amino-1 -(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl- 1 H-pyrazole-3-carbothioic acid amide;

- macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, le- pimectin, spinosad, spinetoram;

- mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyri- daben, tebufenpyrad, tolfenpyrad, flufenerim;

- METI II 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), cyeno- pyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, and pyrifluquinazon; in a synergistically effective amount. Therefore the present invention furthermore relates to a method for combating phy- topathogenic harmful fungi, which process comprises treating the fungi or the plants, the soil or seeds to be protected against fungal attack, with an effective amount of the mixtures as defined herein. The present invention also relates to an agrochemical composition which comprises a solvent or solid carrier and a mixture as defined herein.

Furthermore, the present invention also relates to seed coated with a mixture as defined herein or a composition thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

It is known to use fungicides to protect crop plants from phytopathogenic fungi. However, there is an increasing resistance against the use of fungicdes in food, aand nowadays many countries have legislation that prohibits or restricts the amount of active ingredient used for many fungicides in crop protection. Accordingly, there is a need for new active ingredients that have less toxic side effects and are known to be safe to human.

Another typical problem arising in the field of pathogen control lies in the need to reduce the dosage rates of the fungicides in order to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing pathogen control. A further problem encoutered concerns the need to have available fungal control agents which show an improved action against harmful fungi with a reduced amount of active compounds applied and/or a broadened spectrum of pathogens controlled.

Another difficulty in relation to the use of fungicides is that the repeated and exclusive application of an individual pesticidal compound or compounds of the same mode of action or chemical class leads in many cases to a rapid selection of fungal pathogens that have developed natural or adapted resistance against the active compound or chemical class in question.

Lactylates such as sodium stearoyl lactylate are well-known and safe cosmetic and food additives e.g. used as a dough strengthener in baked goods or as emulsifiers in cleansing products or as hair conditioner. It is noted that WO 2009/092787 describes an anti-bacterial animal feed composition comprising lactylates and/or glycolylates. An animal feed composition is described as being active against gram-positive bacteria in animals. The use for treating or preventing intestinal infections with Clostridium perfringens in animals is specified. While the anti-bacterial activity is elucidated, their efficacy against fungi and specifically against phytopathogenic fungi is not mentioned. There is nothing in this reference that teaches or suggests the specific activity of lactylates and/or glycolylates against phytopathogenic fungi, nor their use in

agrochemical compositions.

Likewise, US 2009/0082253 A1 relates to an antibacterial composition comprising lactylates and to its use as antibacterial agent active against gram-negative bacteria e.g. in the pharmaceutical field, in the feed industry and in the food and drink industry. The reduction or prevention of gram-negative human pathogenic bacteria such as Escherichia coli, Salmonella typhimurium and S. enteridis is specified. GB1 1 15480 suggests the use of acyated alpha-hydroxy carboxylic acids for food conservation and reduction of skin diseases. The compositions described for consumption by or application to humans or other animals have been shown to be active against human pathogenic bacteria and molds e.g. on packaged cheese or leather. There is nothing in these references that teaches or suggests the specific activity of lactylates and/or glycolylates against phytopathogenic fungi, nor their use in agrochemical compositions.

Further, WO 2006/006788 describes a fungicidally active composition of anhydrous milk fat as fungicidally active component and an emulsifier and an antioxidant such as . In one example, calcium stearoyi lactylate is used as an emulsifier for the milk fat and a mixture of propyl gallate and citric acid monoglyceride ester as an antioxidant.

Thus, lactylates, are however, not known to be effective against phytopathogenic fungi or to form synergistically effective mixtures for the control of phytopathogenic fungi. They are therefore also not used as fungicidal agents in agrochemical compositions. In fact, their regulatory status is that of of them being used as

emulsifying agents only.

Agriculturally useful salts of the compounds I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammo- nium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfo- nium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.

The term "an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms" refers to a univalent acyl radical [RCO] from a Ci-C34-alkyl carboxylic acid or from a Ci-C34-alkenyl carboxylic acid with a straight-chained or branched saturated or unsaturated (having at least one double bond) hydrocarbon group, for example bu- tanoyl, butenoyl, hexanoyl (caproyl) (Ce), octoyl (capryloyl) (Cs), lauroyl (C12), myristoyl (C14), hexadecanoyl (palmitoyl) (C16), stearoyi (ds), oleoyl (C18, C18: 1 ), linoleoyl (Cis, C1 8:2), linolenoyl (Cie, C18:3) and erucoyl (C22, C22: 1 ).

According to one embodiment of the invention, preference is given to lactylates or glycolylates of formula I (compounds I) wherein A is -CO-. According to another embodiment, preference is given to lactylates or lactate esters of formula I wherein X is CH3, more preferably to lactylates of formula I, wherein A is -CO- and X is CH3. According to a further embodiment, the use of glycolylates of formula I, wherein A is -CO- and X is H is preferred.

In another embodiment, Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6-20 carbon atoms. More in particular, Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6-1 8 carbon atoms. In this embodiment, suitable substituents include acyl groups having 6 carbon atoms (caproyl), 8 carbon atoms (capryloyl), 1 0 carbon atoms (decanoyl), 12 carbon atoms (lauroyl), 14 carbon atoms (myristoyl), 1 6 carbon atoms (palmitoyl), 18 carbon atoms (stearoyi). Mixtures of two or more com- pounds may also be used. More preferred substituents Ac are selected from acyl radicals of an alkyl or alkenyl carboxylic acid having 6 carbon atoms (caproyl), 8 carbon atoms (capryloyl), 10 carbon atoms (decanoyl), 12 carbon atoms (lauroyl) and 14 carbon atoms (myristoyi).

Where a salt of compounds of formula I is used, the use of a Na, K, Ca, Mg, Fe(ll), Zn, NH4, or Cu(ll) salt may be preferred with a Na, K, Ca, or Mg salt being particularly preferred.

The value for n is preferably in the range of 1 -5. More preferably, n has a value of 1 , 2, or 3, in particular n is 2.

The use of lauroyl lactylate, myristoyi lactylate, and their sodium salts is particularly preferred. In one embodiment, a mixture is used comprising 5-95 wt.% of lauroyl lactylate and 95-5 wt. % of myristoyi lactylate, or the sodium salt(s) of these compounds are used, more in particular, a mixture is used comprising 25-75 wt. %, more in particular 40-60 wt. % of lauroyl lactylate, and 75-25 wt.%, more in particular 40-60 wt. % of myristoyi lactylate, or the sodium salt(s) of these compounds.

Moreover, we have found that simultaneous, that is joint or separate, application of compound I and at least one compound II or successive application of a compound I and of a compound II 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.

The compounds II, their preparation and their activity against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available and known, for example, from the references below:

benalaxyl, methyl N-(phenylacetyl)-N-(2,6-xylyl)-DL-alaninate (DE 29 03 612);

metalaxyl, methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (GB 15 00 581 );

ofurace, (RS)-a -(2-chloro-N-2,6-xylylacetamido)-Y -butyrolactone [CAS RN 58810-48- 3]; oxadixyl; N-(2,6-dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamide (GB 20 58 059); 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 " a l kyl " 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. 41 , p.1029 (1957)); dode- morph, 4-cyclododecyl-2,6-dimethylmorpholine (DE 1 198125); fenpropimorph, (RS)- cis-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (DE 27 52 096); fenpropidin, (RS)-1 -[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine (DE 27 52 096); guazatine, mixture of the reaction products from the amidation of technical grade imi- nodi(octamethylene)diamine, comprising various guanidines and polyamines [CAS RN 108173-90-6]; iminoctadine, 1 ,1 '-iminodi(octamethylene)diguanidine (Congr. Plant Pathol., 1 ., p.27 (1968); spiroxamine, (8-tert-butyl-1 ,4-dioxaspiro[4.5]dec-2-yl)diethyl- amine (EP-A 281 842); tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE 1 1 64 152); pyrimethanil, 4,6-dimethylpyrimidin-2-ylphenylamine (DD-A 151 404); mepanipyrim, (4- methyl-6-prop-1 -ynylpyrimidin-2-yl)phenylamine (EP-A 224 339); cyprodinil, (4-cyclo- propyl-6-methylpyrimidin-2-yl)phenylamine (EP-A 310 550); cycloheximid, 4-{(2R)-2- [(1 S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione [CAS RN 66-81 -9]; griseofulvin, 7-chloro-2\4,6-trimethoxy-6'-methylspiro[benzofuran- 2(3H),1 '-cyclohex-2'-ene]-3,4'-dione [CAS RN 126-07-8]; kasugamycin, 3-0-[2-amino- 4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-a -D-arabino-hexopyranosyl]-D- chiro-inositol [CAS RN 6980-18-3]; natamycin, (8E,14E,16E,18E,20E)-(1 R,3S,5R, 7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-3 -D-mannopyranosyloxy)- 1 ,3,26-trihydroxy-12-methyl-10-oxo-6,1 1 ,28-trioxatricyclo[22.3.1.05'7]octacosa- 8,14,16,18,20-pentaene-25-carboxylic acid [CAS RN 7681 -93-8]; polyoxin, 5-(2-amino- 5-0-carbamoyl-2-deoxy-L-xylonamido)-1 -(5-carboxy-1 ,2,3,4-tetrahydro-2,4-dioxo- pyrimidin-1 -yl)-1 ,5-dideoxy-3 -D-allofuranuronic acid [CAS RN 22976-86-9]; streptomycin, 1 ,1 ' -{1 -L-(1 ,3,5/2,4,6)-4-[5-deoxy-2-0-(2-deoxy-2-methylamino-a -L-gluco- pyranosyl)-3-C-formyl-a -L-lyxofuranosyloxy]-2,5,6-trihydroxycyclohex-1 ,3-ylene}di- guanidine (J. Am. Chem. Soc. Vol. 69, p.1234 (1947)); bitertanol, β -([1 ,1 ' -biphenyl]- 4-yloxy)-a -(1 ,1 -dimethylethyl)-1 H-1 ,2,4-triazole-1-ethanol (DE 23 24 020); bromu- conazole, 1 -[[4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl]methyl]-1 H-1 ,2,4- triazole (Proc. 1990 Br. Crop. Prot. Conf. - Pests Dis. Vol. 1 , p. 459); cyproconazole, 2-(4-chlorophenyl)-3-cyclopropyl-1 -[1 ,2,4]triazol-1 -ylbutan-2-ol (US 4 664 696); difeno- conazole, 1 -{2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-[1 ,3]dioxolan-2-ylmeth- yl}-1 H-[1 ,2,4]triazole (GB-A 2 098 607); diniconazole, (β Ε)-β -[(2,4-dichlorophenyl)- methylene]-a -(1 ,1 -dimethylethyl)-1 H-1 ,2,4-triazole-1 -ethanol (Noyaku Kagaku, 1983, Vol. 8, p. 575); enilconazole (imazalil), 1 -[2-(2,4-dichlorphenyl)-2-(2-propenyloxy)ethyl]- 1 H-imidazole (Fruits, 1973, Vol. 28, p. 545); epoxiconazole, (2RS,3SR)-1 -[3-(2-chloro- phenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1 H-1 ,2,4-triazole (EP-A 196 038); fenbu- conazole, a -[2-(4-chlorophenyl)ethyl]-a -phenyl-1 H-1 ,2,4-triazole-1 -propanenitrile (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis. Vol. 1 , p. 33); fluquinconazole, 3-(2,4- dichlorophenyl)-6-fluoro-2-[1 ,2,4]- triazol-1 -yl-3H-quinazolin-4-one (Proc. Br. Crop Prot. Conf.-Pests Dis., 5-3, 41 1 (1992)); flusilazole, 1 -{[bis-(4-fluorophenyl)methyl- silanyl]methyl}-1 H-[1 ,2,4]triazole (Proc. Br. Crop Prot. Conf.-Pests Dis., 1 , 413 (1984)); flutriafol, a -(2-fluorophenyl)-a -(4-fluorophenyl)-1 H-1 ,2,4-triazole-1 -ethanol (EP 15 756); hexaconazole, 2-(2,4-dichlorophenyl)-1 -[1 ,2,4]triazol-1 -ylhexan-2-ol (CAS RN 79983-71 -4); ipconazole, 2-[(4-chlorophenyl)methyl]-5-(1 -methylethyl)-1 -(1 H-1 ,2,4- triazol-1 -ylmethyl)cyclopentanol (EP 267 778), metconazole, 5-(4-chlorobenzyl)-2,2- dimethyl-1 -[1 ,2,4]triazol-1 -ylmethylcyclopentanol (GB 857 383); myclobutanil, 2-(4- chlorophenyl)-2-[1 ,2,4]triazol-1 -ylmethylpentanenitrile (CAS RN 88671- 89- 0); pen- conazole, 1 -[2-(2,4-dichlorophenyl)pentyl]-1 H-[1 ,2,4]triazole (Pesticide Manual, 12th Ed. (2000), S.712); propiconazole, 1 -[[2-(2,4-dichlorophenyl)-4-propyl-1 ,3-dioxolan-2- yl]methyl]-1 H-1 ,2,4-triazole (BE 835 579); prochloraz, N-(propyl-[2-(2,4,6-trichloro- phenoxy)ethyl])imidazole-1 -carboxamide (US 3 991 071 ); prothioconazole, 2-[2-(1 - chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1 ,2,4]triazole-3- thione (WO 96/16048); simeconazole, a -(4-fluorophenyl)-a -[(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 793 867); triadimenol, β -(4-chlorophenoxy)-a -(1 ,1 -dimethylethyl)-1 H-1 ,2,4-triazole-1 - ethanol (DE 23 24 010); triflumizol, (4-chloro-2-trifluormethylphenyl)-(2-propoxy-1 - [1 ,2,4]triazol-1 -ylethyliden)-amine (JP-A 79/1 19 462); triticonazole, (5E)-5-[(4- chlorophenyl)methylene]-2,2-dimethyl-1 -(1 H-1 ,2,4-triazol-1 -ylmethyl)cyclopentanol (FR 26 41 277); iprodione, N-isopropyl-3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1 - carboxamide (GB 13 12 536); myclozolin, (RS)-3-(3,5-dichlorophenyl)-5-methoxy- methyl-5-methyl-1 ,3-oxazolidine-2,4-dione [CAS RN 54864-61 -8]; procymidone, N-(3,5- dichlorophenyl)-1 ,2-dimethylcyclopropane-1 ,2-dicarboximide (US 3 903 090); vinclo- zolin, 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione (DE-A 22 07 576); ferbam, iron(3+) dimethyldithiocarbamate (US 1 972 961 ); nabam, disodium ethylene- bis(dithiocarbamate) (US 2 317 765); maneb, manganese ethylenebis(dithiocarbamate) (US 2 504 404); mancozeb, manganese ethylenebis(dithiocarbamate) polymer com- plex zinc salt (GB 996 264); metam, methyldithiocarbaminic acid (US 2 791 605); meti- ram, zinc ammoniate ethylenebis(dithiocarbamate) (US 3 248 400); propineb, zinc pro- pylenebis(dithiocarbamate) polymer (BE 61 1 960); polycarbamate, bis(dimethylcar- bamodithioato-K S,K S' )[μ -[[1 ,2-ethanediylbis[carbamodithioato-K S,K S' ]](2- )]]- di[zinc] [CAS RN 64440-88-6]; thiram, bis(dimethylthiocarbamoyl) disulfide (DE 642 532); ziram, dimethyldithiocarbamate [CAS RN 137-30-4]; zineb, zinc ethylene- bis(dithiocarbamate) (US 2 457 674); anilazine, 4,6-dichloro-N-(2-chlorophenyl)-1 ,3,5- triazine-2-amine (US 2 720 480); benomyl, N-butyl-2-acetylaminobenzoimidazole-1 - carboxamide (US 3 631 176); boscalid, 2-chloro-N-(4' -chlorobiphenyl-2-yl)nicotin- amide (EP-A 545 099); carbendazim, methyl (1 H-benzoimidazol-2-yl)carbamate (US 3 657 443); carboxin, 5,6-dihydro-2-methyl-N-phenyl-1 ,4-oxathiin-3-carboxamide (US 3 249 499); oxycarboxin, 5,6-dihydro-2-methyl-1 ,4-oxathiin-3-carboxanilide 4,4-dioxide (US 3 399 214); cyazofamid, 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1 H- imidazole-1 -sulfonamide (CAS RN 1201 16-88-3]; dazomet, 3,5-dimethyl-1 ,3,5-thia- diazinane-2-thione (Bull. Soc. Chim. Fr. Vol. 15, p. 891 (1897)); dithianon, 5,10-dioxo- 5,10-dihydronaphtho[2,3-b][1 ,4]dithiin-2,3-dicarbonitrile (GB 857 383); famoxadone, (RS)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1 ,3-oxazolidine-2,4-dione [CAS RN 131807-57-3]; fenamidone, (S)-1 -anilino-4-methyl-2-methylthio-4-phenylimidazolin-5- one [CAS RN 161326-34-7]; fenarimol, a -(2-chlorophenyl)-a -(4-chlorophenyl)-5- pyrimidinemethanol (GB 12 18 623); fuberidazole, 2-(2-furanyl)-1 H-benzimidazole (DE 12 09 799); flutolanil, a ,a ,a -trifluoro-3' -isopropoxy-o-toluanilide (JP 1 104514); furametpyr, 5-chloro-N-(1 ,3-dihydro-1 ,1 ,3-trimethyl-4-isobenzofuranyl)-1 ,3-dimethyl-1 H- pyrazole-4-carboxamide [CAS RN 123572-88-3]; isoprothiolane, diisopropyl 1 ,3-dithio- lan-2-ylidenemalonate (Proc. Insectic. Fungic. Conf. 8. Vol. 2, p. 715 (1975)); mepronil, 3 '-isopropoxy-o-toluanilide (US 3 937 840); nuarimol, a -(2-chlorophenyl)-a -(4-fluoro- phenyl)-5-pyrimidinemethanol (GB 12 18 623); fluopicolide (picobenzamid), 2,6-di- chloro-N-(3-chloro-5-trifluoromethylpyridin-2-ylmethyl)benzamide (WO 99/42447); pro- benazole, 3-allyloxy-1 ,2-benzothiazole 1 ,1 -dioxide (Agric. Biol. Chem. Vol. 37, p. 737 (1973)); proquinazid, 6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one (WO 97/48684); pyrifenox, 2' ,4' -dichloro-2-(3-pyridyl)acetophenone (EZ)-O-methyloxime (EP 49 854); pyroquilon, 1 ,2,5,6-tetrahydropyrrolo[3,2,1 -ij]quinolin-4-one (GB 139 43 373); quinoxyfen, 5,7-dichloro-4-(4-fluorophenoxy)quinoline (US 5 240 940); silthiofam, N- allyl-4,5-dimethyl-2-(trimethylsilyl)thiophene-3-carboxamide [CAS RN 175217-20-6]; thiabendazole, 2-(1 ,3-thiazol-4-yl)benzimidazole (US 3 017 415); thifluzamide, 2' ,6' - dibromo-2-methyl-4' -trifluormethoxy-4-trifluormethyl-1 ,3-thiazole-5-carboxanilide

[CAS RN 130000-40-7]; thiophanate-methyl, 1 ,2-phenylenebis(iminocarbonothioyl)- bis(dimethylcarbamate) (DE-A 19 30 540); tiadinil, 3' -chloro-4,4' -dimethyl-1 ,2,3- thiadiazole-5-carboxanilide [CAS RN 223580-51 -6]; tricyclazole, 5-methyl-1 ,2,4- triazolo[3,4-b][1 ,3]benzothiazole [CAS RN 41814-78-2]; triforine, Ν,Ν' -{piperazine- 1 ,4-diylbis[(trichlormethyl)methylene]}diformamide (DE 19 01 421 ); Bordeaux mixture, mixture of CuS04 x 3Cu(OH)2 x 3CaS04 [CAS RN 801 1 -63-0] copper acetate,

Cu(OCOCH3)2 [CAS RN 801 1 -63-0]; copper oxychloride, Cu2CI(OH)3 [CAS RN 1332- 40-7]; basic copper sulfate, CuS04 [CAS RN 1344-73-6]; binapacryl, (RS)-2-sec-butyl- 4,6-dinitrophenyl 3-methylcrotonate [CAS RN 485-31 -4]; dinocap, the mixture of 2,6- dinitro-4-octylphenylcrotonate and 2,4-dinitro-6-octylphenylcrotonate, where " octyl" is a mixture of 1 -methylheptyl, 1 -ethylhexyl and 1 -propylpentyl (US 2 526 660); dinobu- ton, (RS)-2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate [CAS RN 973-21 -7]; ni- trothal-isopropyl, diisopropyl 5-nitroisophthalate (Proc. Br. Insectic. Fungic. Conf. 7., Vol. 2, p. 673 (1973)); fenpiclonil, Fludioxonil, 4-(2,3-dichlorophenyl)-1 H-pyrrole-3- carbonitrile (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., Vol. 1 , p. 65); fludioxonil, 4- (2,2-difluorobenzo[1 ,3]dioxol-4-yl)-1 H-pyrrole-3-carbonitrile (The Pesticide Manual, publ. The British Crop Protection Council, 10th ed. (1995), p. 482); acibenzolar-S- methyl, methyl 1 ,2,3-benzothiadiazol-7-carbothioate [CAS RN 135158-54-2]; fluben- thiavalicarb (benthiavalicarb), isopropyl {(S)-1 -[(1 R)-1 -(6-fluorobenzothiazol-2-yl)- ethylcarbamoyl]-2-methylpropyl}carbamate (JP-A 09/323 984); carpropamid, 2,2-di- chloro-N-[1 -(4-chlorphenyl)ethyl]-1 -ethyl-3-methylcyclopropanecarboxamide [CAS RN 104030-54-8]; chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3 290 353); cy- flufenamid, (Z)-N-[a -(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)benzyl]- 2-phenylacetamide (WO 96/19442); cymoxanil, 1 -(2-cyano-2-methoxyiminoacetyl)-3- ethylurea (US 3 957 847); diclomezine, 6-(3,5-dichlorophenyl-p-tolyl)pyridazin-3(2H)- one (US 4 052 395); diclocymet, (RS)-2-cyano-N-[(R)-1 -(2,4-dichlorophenyl)ethyl]-3,3- dimethylbutyramide [CAS RN 139920-32-4]; diethofencarb, isopropyl 3,4-diethoxy- carbanilate (EP 78 663); edifenphos, O-ethyl S,S-diphenyl phosphorodithioate (DE 14 93 736); ethaboxam, N-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazole- carboxamide (EP-A 639 574); fenhexamid, N-(2,3-dichloro-4-hydroxyphenyl)-1 - methylcyclohexanecarboxamide (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, Vol. 2, p. 327); fentin acetate, triphenyltin (US 3 499 086); fenoxanil, N-(1 -cyano-1 ,2- dimethylpropyl)-2-(2,4-dichlorophenoxy)propanamide (EP 262 393); ferimzone, me- panipyrim, (Ζ)-2' -methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone [CAS RN 89269-64-7]; fluazinam, 3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5- (trifluoromethyl)-2-pyridinamine (The Pesticide Manual, publ. The British Crop Protection Council, 10th ed. (1995), p. 474); fosetyl, fosetyl-aluminum, ethylphosphonate (FR 22 54 276); iprovalicarb, isopropyl [(1 S)-2-methyl-1 -(1 -p-tolylethylcarbamoyl)propyl]- carbamate (EP-A 472 996); hexachlorbenzene (C. R. Seances Acad. Agric. Fr., Vol. 31 , p. 24 (1945); metrafenon, 3' -bromo-2,3,4,6' -tetramethoxy-2' ,6-dimethylbenzo- phenone (US5,945,567); pencycuron, 1 -(4-chlorobenzyl)-1 -cyclopentyl-3-phenylurea (DE 27 32 257); penthiopyrad, (RS)-N-[2-(1 ,3-dimethylbutyl)-3-thienyl]-1 -methyl-3- (trifluoromethyl)-l H-pyrazole-4-carboxamide (JP 10130268); propamocarb, propyl 3- (dimethylamino)propylcarbamate (DE 15 67 169); phthalide (DE 16 43 347); toloclofos- methyl, 0-2,6-dichloro-p-tolyl 0,0-dimethyl phosphorothioate (GB 14 67 561 ); quintoz- ene, pentachlornitrobenzene (DE 682 048); zoxamide, (RS)-3,5-dichloro-N-(3-chloro-1 - ethyl-1 -methyl-2-oxopropyl)-p-toluamide [CAS RN 156052-68-5]; azoxystrobin, methyl 2-{2-[6-(2-cyano-1 -vinyl penta-1 , 3-dienyloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy- acrylate (EP 382 375); dimoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-[a -(2,5- xylyloxy)-o-tolyl]acetamide (EP 477 631 ); enestroburin, methyl 2-{2-[3-(4-chlorophenyl)- 1 -methylallylideneaminooxymethyl]phenyl}-3-methoxyacrylate (EP 936 213); fluox- astrobin, (E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro- 1 ,4,2-dioxazin-3-yl)methanone O-methyloxime (WO 97/27189); kresoxim-methyl, methyl (E)-methoxyimino[a -(o-tolyloxy)-o-tolyl]acetate (EP 253 213); metominostrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide (EP 398 692); orysas- trobin, (2E)-2-(methoxyimino)-2-{2-[(3E,5E,6E)-5-(methoxyimino)-4,6-dimethyl-2,8-di- oxa-3,7-diazanona-3,6-dien-1 -yl]phenyl}-N-methylacetamide (WO 97/15552); picoxy- strobin, 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-yloxymeth- yl]phenyl}(N-methoxy)carbamate (WO 96/01256); trifloxystrobin, methyl (E)-methoxy- imino-{(E)-a -[1 -(a ,a ,a -trifluoro-m-tolyl)ethylideneaminooxy]-o-tolyl}acetate (EP 460 575); captafol, N-(1 ,1 ,2,2-tetrachloroethylthio)cyclohex-4-ene-1 ,2-dicarboximide (Phytopathology, Vol. 52, p. 754 (1962)); captan, N-(trichloromethylthio)cyclohex-4-ene-1 ,2- dicarboximide (US 2 553 770); dichlofluanid, N-dichlorofluoromethylthio-N,N-dimethyl- N-phenylsulfamide (DE 1 1 93 498); folpet, N-(trichlormethylthio)phthalimide (US 2 553 770); tolylfluanid, N-dichlorofluoromethylthio-N,N-dimethyl-N-p-tolylsulfamide (DE 1 1 93 498); dimethomorph, 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1 -morpholin-4- yl-propenone (EP 120 321 ); flumetover, 2-(3,4-dimethoxyphenyl)-N-ethyl-a ,a ,a -tri- fluoro-N-methyl-p-toluamide [AGROW no. 243, 22 (1995)]; flumorph, 3-(4-fluorophen- yl)-3-(3,4-dimethoxyphenyl)-1 -morpholin-4-ylpropenone (EP 860 438); 5-Amino-2- isopropyl-3-oxo-4-o-tolyl-2,3-dihydro-pyrazole-1 -carbothioic acid S-allyl ester

(CN1939128).

The compounds described by lUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP- A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783;

WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358;

WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ;

WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690;

WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325;

WO 06/87343; WO 07/82098; WO 07/90624).

According to the present invention, it may be preferred that the mixtures comprise as compound II a compound that is selected from the group A), C), D), E), F) and G).

According to another embodiment of the invention, mixtures comprise as compound II a compound that is selected from the group H).

According to a further embodiment, mixtures comprise as compound II a compound that is selected from the group I).

According to a further embodiment, mixtures comprise as compound II a compound of group A (strobilurins), preferably selected from pyraclostrobin, kresoxim-methyl, azoxystrobin, fluoxastrobin, trifloxystrobin, enestroburin and pyribencarb, more preferably from pyraclostrobin and fluoxastrobin.

According to a further emobodiment, group B) of compounds II is as follows:

- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, sedaxane, carboxin, penthiopyrad, boscalid, fenfuram, fenhexamid, flutolanil, furametpyr, isopyrazam, isoti- anil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxy- carboxin, , tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 , 1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3- difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(4'-trifluoromethylthiobiphenyl- 2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3-trimethyl- butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide;

- carboxylic morpholides: dimethomorph, flumorph;

- 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;

According to a further embodiment, mixtures comprise as compound II a compound of group B (carboxamides), preferably selected from bixafen, penthiopyrad, sedaxane, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)- nicotinamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole- 4-carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl- 1 H-pyrazole-4-carboxamide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl- 5-fluoro-1 H-pyrazole-4-carboxamide, fluopyram, mandiproamid, amisulbrom, flutolanil, metalaxyl, oxadixyl, benalaxyl, ofurace, dimethomorph, zoxamide and flumetover.

According to a further embodiment, mixtures comprise as compound II 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, more preferably selected from epoxiconazole and prothioconazole.

According to a further embodiment, mixtures comprise as compound II 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- 1 -carbothioic acid S-allyl ester.

According to a further embodiment, the mixtures comprise at least one compound (II) selected from the group of E) carbamates, more preferably selected from man- cozeb, maneb and metiram.

According to a further embodiment, mixtures comprise as compound II a compound of group F (other active substances), preferably selected from cymoxanil, thiophanate- methyl, fosetyl, chlorothalonil, copper, copper hydroxide and copper oxychloride.

Preference is also given to three-component mixtures of one compound I with two of the active compounds II mentioned above.

The mixtures and compositions according to the invention are suitable as fungicides. 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. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.

Preferably the 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.

The term "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 in- eludes 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.

Preferably, treatment of plant propagation materials with the inventive combination of compounds I and compounds II 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.

The term "cultivated 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/agri_products.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. Typically, 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-translational 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 agrochemical compositions and the fungicidal mixtures, respectively, are particularly suitable for controlling the following fungal plant diseases:

Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Bipolaris and Drechslera spp.

(teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokiniana) on cereals and e.g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); 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; 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; 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. cruciferarum); 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. verticillioides 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); Guignardia bidwellii (black rot) on vines; Microdo- chium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Moni- linia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. para- sitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P.

manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; 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); Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (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) on wheat or P. teres (net blotch) on barley; Pyricu- laria 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. aphanidermatum); 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; Rhynchosporium secalis (scald) on barley, rye and triticale; 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; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears.

In particular, the mixtures and the compositions thereof 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 compounds I and compounds II, and salts thereof can be converted into customary types of agrochemical 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 compound according to the invention.

Examples for 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). Usually the composition types (e. g. SC, OD, FS, WG, SG, WP, SP, SS, WS, GF) are employed diluted. 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,

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. Wiley & Sons, New York, 1961 ), Hance et al.: Weed Control Handbook (8th Ed., Blackwell Scientific, Oxford, 1989) and Mollet, H. and Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001 ).

The agrochemical compositions may also comprise auxiliaries which are customary in agrochemical compositions. The auxiliaries used depend on the particular applica- tion form and active substance, respectively.

Examples for suitable 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 for- mulations).

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. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their de- rivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones such as cyclohexanone and gamma-butyrolactone, fatty acid dimethyla- mides, fatty acids and fatty acid esters and strongly polar solvents, e. g. amines such as N-methylpyrrolidone.

Solid carriers are mineral earths such as silicates, silica gels, talc, kaolins, lime- stone, 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.

Suitable surfactants (adjuvants, wtters, tackifiers, dispersants or emulsifiers) 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, furthermore condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxy-ethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearyl- phenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and proteins, denatured proteins, polysaccharides (e. 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.

Examples for thickeners (i. e. compounds that impart a modified flowability to compositions, i. e. high viscosity under static conditions and low viscosity during agitation) are polysaccharides and organic and anorganic clays such as Xanthan gum (Kelzan®, CP Kelco, U.S.A.), Rhodopol® 23 (Rhodia, France), Veegum® (R.T. Vanderbilt, U.S.A.) or Attaclay® (Engelhard Corp., NJ, USA).

Bactericides may be added for preservation and stabilization of the composition. Examples for 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).

Examples for suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Examples for anti-foaming agents are 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 1 12, 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 1 12, 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.

Examples for tackifiers or binders are 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 compounds I and compounds II 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. Examples of 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. 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.

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 ac- tive 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 usu- ally 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 compositions 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. In a preferred embodiment, the compounds or the compositions thereof, respectively, are applied on to the plant propagation mate- rial by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.

In a preferred embodiment, a suspension-type (FS) composition is used for seed treatment. Typcially, 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. in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading, brushing, immersing or pouring. The application forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active substances according to the invention.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, 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. Alternatively, it is possible to prepare 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.

When employed in plant protection, the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active substance per ha.

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.

When used in the protection of materials or stored products, 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.

Various types of oils, wetters, adjuvants, herbicides, bactericides, other fungicides and/or pesticides may be added to the mixtures 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®.

The 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).

According to this invention, applying compounds I together with a compound II is to be understood to denote, that compounds I and at least one compound II occur simultaneously at the site of action (i.e. the harmful fungi to be controlled or their habitats such as infected plants, plant propagation materials, particularly seeds, surfaces, mate- rials 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 compounds I and compound II 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.

In the mixtures and compositions according to the invention the weight ratio of compounds I and compound II 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 , more preferably in the range of from 1 :10 to 10:1 and particularly in the range of from 1 :5 to 5:1 (compounds I : compound II). In another embodiment, the weight ratio of compounds I and compound II is in the range of from 1000:1 to 1 :1 , preferably in the range of from 100:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 and particularly in the range of from 10:5 to 2:1 (compounds I : compound II).

Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the compounds I.

In the mixtures and compositions, the compound l/compound II 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 Colby's formula (Colby, S. R., "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, pp. 20-22, 1967).

The term "synergistic effect" is also understood to refer to that defined by application of the Tammes method, (Tammes, P. M. L, "Isoboles, a graphic representation of synergism in pesticides", Netherl. J. Plant Pathol. 70, 1964).

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.

According to one embodiment, 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).

In a further embodiment, 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).

In a further embodiment, either individual components of the composition according to the invention or partially premixed components can be applied jointly (e.g. after tankmix) or consecutively.

The fungicidal action of the compositions according to the invention can be shown by the examples described below which show the inventive merits of this invention, without being llimited thereto or thereby.

Glass house Trials

The active compounds, separately or jointly, 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.

The visually determined percentages of infected leaf areas are converted into efficacies in % of the untreated control.

The efficacy (E) is calculated as follows using Abbot's formula:

E = (1 - α/β ) 100 a corresponds to the fungicidal infection of the treated plants in % and

β 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 expected efficacies of active compound combinations were determined using Colby's formula (Colby, S.R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 1 5, pp. 20-22, 1967) and compared with the observed efficacies.

Colby's formula: E = x + y - χ · y/100

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.

Microstests

The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. Sodium stearoyl lactylate was obtained from Dr. Straetmanns (Dermofeel® SL).

The product orysastrobin was used as commercial finished formulation and diluted with water to the stated concentration of the active compound.

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of the respective pathogen in the respective nutrient medium 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.

The expected efficacies of active compound mixtures were determined using Colby's formula [R.S. Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficacies. Use example 1. Activity against the grey mold pathogen Botrytis cinerea

A spore suspension of Botrytis cinerea containing a aqueous biomalt medium was used.

Figure imgf000025_0001

Use example 2. Activity against the rice blast pathogen Pyricularia oryzae

A spore suspension of Pyricularia oryzae containing a aqueous biomalt medium was used.

Active compound / Concentration Mixture Observed Calculated efficacy active mixture (ppm) efficacy according to Colby

(%)

Sodium stearoyl

4

lactylate 2

Fluoxastrobin 0.016 - 12

Mancozeb 1 - 18

Sodium stearoyl

4

lactylate + 250 : 1 39 14

Fluoxastrobin 0.016

Sodium stearoyl

4

lactylate + 4 : 1 45 19

Mancozeb 1

Use example 3. Activity against the wheat leaf blotch pathogen Septoria tritici

A spore suspension of Septoria tritici containing a aqueous biomalt medium was used.

Active compound / Concentration Mixture Observed Calculated efficacy active mixture (ppm) efficacy according to Colby

(%)

Sodium stearoyl 16 - 15

lactylate 4 13

Fluoxastrobin 0.063 - 18

Prothioconazole 0.063 - 19

Sodium stearoyl

16

lactylate + 250 : 1 94 30 Fluoxastrobin 0.063

Sodium stearoyl

4

lactylate + 4 : 1 59 30 Prothioconazole 0.063

Claims

Claims
1 . A mixture, comprising as active compounds
1 ) at least one compound of formula I
Figure imgf000027_0001
wherein
Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 2 to 35 carbon atoms, wherein the carbon chain is branched or unbranched,
X is H or CHs; n is an integer with a value of 1 to 10;
A is, if n > 1 , -CO-, or
A is, if n = 1 , -CO- or a direct bond; or an agrochemically acceptable salt thereof; and
2) at least one active compound II selected from groups A) to I): A) strobilurins
azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrame- tostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-(2-(6-(3-chloro-2- methyl-phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N- methyl-acetamide, 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclopropane- carboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester, methyl (2- chloro-5-[1 -(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2-(2-(3- (2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2- methoxyimino-N-methyl-acetamide;
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, penflufen, penthiopyrad, sedaxane, tecloftalam, thif- luzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro- N-(1 ,1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-(3',4',5'-trifluorobiphenyl- 2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(4'-trifluoro- methylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carbox- amide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- pyrazole-4-carboxamide;
- carboxylic morpholides: dimethomorph, flumorph, pyrimorph;
- benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N-(3- Ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide; - other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracy- clin, silthiofarm and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
C) azoles
- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difeno- conazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ip- conazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, pen- conazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -(4- chloro-phenyl)-2-([1 ,2,4]triazol-1 -yl)-cycloheptanol;
- imidazoles: cyazofamid, imazalil, pefurazoate, prochloraz, triflumizol;
- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
- others: ethaboxam, etridiazole, hymexazole and 2-(4-chloro-phenyl)-N-[4- (3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;
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-trichloropyridine-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, diflumetorim, fenarimol, ferimzone, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;
- piperazines: triforine;
- pyrroles: fenpiclonil, fludioxonil;
- morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;
- piperidines: fenpropidin;
- dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
- non-aromatic 5-membered heterocycles: famoxadone, fenamidone, fluti- anil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3- dihydro-pyrazole-1 -carbothioic acid S-allyl ester;
- others: acibenzolar-S-methyl, ametoctradin, amisulbrom, anilazin, blasti- cidin-S, captafol, captan, chinomethionat, dazomet, debacarb, di- clomezine, difenzoquat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, quinoxyfen, triazoxide, tri- cyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, 5-chloro-1 -(4,6- dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole and 5-chloro-7-(4- methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo- [1 ,5-a]pyrimidine;
E) carbamates
- thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasul- phocarb, metiram, propineb, thiram, zineb, ziram;
- carbamates: benthiavalicarb, diethofencarb, iprovalicarb, propamocarb, propamocarb hydrochlorid, valifenalate and N-(1 -(1 -(4-cyano-phenyl)- ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
F) other active substances
- 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 acid and its salts, pyrazophos, tolclofos-methyl; - organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N-(4-chloro- 2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
- inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
- others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamin,
metrafenone, mildiomycin, oxin-copper, prohexadione-calcium, spiroxam- ine, tebufloquin, tolylfluanid, N-(cyclopropylmethoxyimino-(6-difluoro- methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro- 3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl forma- midine, N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N- ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethyl- silanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N'-(5- difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N- methyl formamidine,
2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)- amide, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-
4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen- 1 -yl-amide, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin- 4-yl ester and N-Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)- acetyl]-piperidin-4-yl}-N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4-thi- azolecarboxamide;
G) growth regulators
abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flu- metralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, pro- hexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapen- thenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid , trinexapac- ethyl and uniconazole;
H) herbicides
- acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproani- lide, 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, dime- piperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
- cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, seth- oxydim, tepraloxydim, tralkoxydim;
- dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodia- mine, trifluralin;
- diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fome- safen, lactofen, oxyfluorfen;
- hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;
- imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, ima- zaquin, imazethapyr; - phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
- pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate;
- pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, flu- roxypyr, picloram, picolinafen, thiazopyr;
- sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron- ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, fla- zasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron- methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfu- ron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 -((2-chloro-6- propyl-imidazo[1 ,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2- yl)urea;
- triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazi- none, metamitron, metribuzin, prometryn, simazine, terbuthylazine, ter- butryn, triaziflam;
- ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron,tebuthiuron;
- other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam- methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, or- tho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, py- roxasulfone, pyroxsulam;
- others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone,benfluresate, benzofenap, bentazone, benzobicyclon, bicy- clopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, car- fentrazone, cinidon-ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fen- trazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flur- tamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclo- nil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quino- clamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3- methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1 -yl)- phenoxy]-pyridin-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2- cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2- cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4- chloro-phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)- pyridine-2-carboxylic acid methyl ester;
I) insecticides
- organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl,
chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, di- crotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
- carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, car- bofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, ox- amyl, pirimicarb, propoxur, thiodicarb, triazamate;
- pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cy- permethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imi- prothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
- insect growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlor- fluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflu- muron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, dio- fenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spi- rodiclofen, spiromesifen, spirotetramat;
- nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefu- ran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -
(2-chloro-thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
- GABA antagonist compounds: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1 -(2,6-dichloro-4-methyl-phenyl)-4- sulfinamoyl-1 H-pyrazole-3-carbothioic acid amide;
- macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, le- pimectin, spinosad, spinetoram;
- mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
- METI II 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, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistriflu- ron, and pyrifluquinazon; in a synergistically effective amount. 2. The mixture according to claim 1 , comprising a compound I and a compound II in a weight ratio of from 1000:1 to 1 :1 .
3. The mixture according to claim 1 or 2, wherein A is -CO-.
4. The mixture according to any of the claims 1 to 3, wherein X is CH3.
5. The mixture according to any of the claims 1 to 4, wherein Ac is an acyl radical of an alkyl or alkenyl carboxylic acid having 6 to 18 carbon atoms.
6. The mixture according to claim 5, wherein Ac is selected from acyl radicals of alkyl or alkenyl carboxylic acids having 6 carbon atoms (caproyi), 8 carbon atoms (capryloyl), 10 carbon atoms (decanoyl), 12 carbon atoms (lauroyl) and 14 carbon atoms (myristoyl).
7. The mixture according to any of the claims 1 to 6, wherein n is 1 , 2 or 3.
8. The mixture according to any of the claims 1 to 7, wherein the agriculturally acceptable salt of compound I is a Na, K, Ca, Mg, Fe(ll), Zn, NH4, or Cu(ll) salt.
9. The mixture according to any of the claims 1 to 8, wherein compound I is sodium stearoyl lactylate.
10. The mixture according to any of the claims 1 to 9, wherein component 2) is at least one compound II selected from pyraclostrobin, kresoxim-methyl, azox- ystrobin, fluoxastrobin, trifloxystrobin, enestroburin and pyribencarb.
1 1 . The mixture according to any of the claims 1 to 10 comprising at least two active compounds II.
12. An agrochemical composition wherein said composition comprises a solvent or solid carrier and a mixture according to any of the claims 1 to 1 1.
13. A method for combating harmful fungi, comprising:
treating the fungi or the plants, the soil or seeds to be protected against fungal attack with an effective amount of the mixtures as defined in any of the claims 1 to 1 1 , or a composition as defined in claim 12.
14. The use of the mixtures as defined in any of claims 1 to 1 1 , for protecting plant propagation material, seed, the seedlings' roots and shoots from infestation by harmful fungi.
15. Seed coated with a mixture as defined in any of the claims 1 to 1 1 , or a composition as defined it claim 12, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
PCT/EP2010/062565 2009-09-01 2010-08-27 Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi WO2011026796A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP09169127.9 2009-09-01
EP09169127 2009-09-01

Publications (1)

Publication Number Publication Date
WO2011026796A1 true WO2011026796A1 (en) 2011-03-10

Family

ID=41571446

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/062565 WO2011026796A1 (en) 2009-09-01 2010-08-27 Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi

Country Status (1)

Country Link
WO (1) WO2011026796A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013007558A3 (en) * 2011-07-08 2013-04-04 Purac Biochem Bv Active formulation for use in feed products
CN105251497A (en) * 2015-09-28 2016-01-20 江苏七洲绿色化工股份有限公司 Solid catalyst, and preparation method and applications thereof
CN105494387A (en) * 2015-12-16 2016-04-20 江苏辉丰农化股份有限公司 Pesticide composition
WO2016121354A1 (en) * 2015-01-26 2016-08-04 国立研究開発法人農業・食品産業技術総合研究機構 Soil-borne disease control method, soil for plant cultivation use, and soil-borne disease control agent
CN107047576A (en) * 2017-03-07 2017-08-18 南京华洲药业有限公司 Sterilizing compound containing fluoxastrobin and kresoxim-methyl and application thereof

Citations (157)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1972961A (en) 1931-05-26 1934-09-11 Du Pont Disinfectant
DE642532C (en) 1934-06-30 1937-03-08 Ig Farbenindustrie Ag Means for fighting of Pilzschaedigungen in orchards
DE682048C (en) 1932-12-23 1939-10-06 Ig Farbenindustrie Ag Soil treatment agent for combating fungal plant Saddle Edlingen
US2317765A (en) 1941-08-20 1943-04-27 Rohm & Haas Fungicidal composition
US2457674A (en) 1944-12-02 1948-12-28 Rohm & Haas Fungicidal compositions
US2504404A (en) 1946-06-12 1950-04-18 Du Pont Manganous ethylene bis-dithiocarbamate and fungicidal compositions containing same
US2526660A (en) 1946-07-06 1950-10-24 Rohm & Haas Capryldintrophenyl crotonate
US2553770A (en) 1948-05-18 1951-05-22 Standard Oil Dev Co Parasiticidal compounds containing the nsccll3 group
US2720480A (en) 1953-07-17 1955-10-11 Ethyl Corp Fungicidal compositions and method of using same
US2791605A (en) 1954-07-28 1957-05-07 Stauffer Chemical Co Stabilization of salts of monoalkyldithiocarbamic acids
GB857383A (en) 1957-10-26 1960-12-29 Merck Ag E New dithia-anthracene derivatives and fungicidal compositions containing them
US3017415A (en) 1960-01-18 1962-01-16 Merck & Co Inc Certain benzimidazoles carrying thiazolyl, thiadiazolyl and isothiazolyl substituents in the 2 position
BE611960A (en) 1960-12-28 1962-07-27
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
DE1164152B (en) 1961-02-22 1964-02-27 Basf Ag antifungal agents
DE1193498B (en) 1960-11-03 1965-05-26 Bayer Ag A process for preparing Sulfensaeurederivaten
GB996264A (en) 1961-05-09 1965-06-23 Rohm & Haas Metal bisdithiocarbamate complexes
DE1209799B (en) 1964-05-14 1966-01-27 Bayer Ag Dressers against Fusarium
US3248400A (en) 1957-08-17 1966-04-26 Basf Ag Fungicidal agents containing dithiocarbamate and thiuram disulfide radicals
US3249499A (en) 1965-04-26 1966-05-03 Us Rubber Co Control of plant diseases
US3290353A (en) 1963-04-01 1966-12-06 Diamond Alkali Co Halogenated aromatic nitriles
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
GB1115480A (en) 1964-08-26 1968-05-29 Patterson Co C Improvements relating to the control of micro organisms
US3399214A (en) 1965-11-05 1968-08-27 Uniroyal Inc Oxides of carboxamido oxathiins
DE1493736A1 (en) 1965-08-26 1969-04-03 Bayer Ag A process for preparing Dithiolphosphorsaeuretriestern
DE1901421A1 (en) 1968-01-23 1969-08-28 Boehringer Sohn Ingelheim diaminocompounds
DE1930540A1 (en) 1968-06-18 1970-01-08 Nippon Soda Co Thioureidobenzole and processes for their preparation
US3499086A (en) 1953-07-03 1970-03-03 Hoechst Ag Methods and compositions for controlling fungal and bacterial infestation of plants utilizing organic tetravalent tin compounds
DE1567169A1 (en) 1966-12-17 1970-08-06 Schering Ag Fungicides and fungistatic agents
GB1218623A (en) 1967-04-27 1971-01-06 Lilly Co Eli Susbtituted-5-pyrimidine compounds
DE1643347A1 (en) 1967-08-23 1971-05-27 Bayer Ag A process for the preparation of aromatic lactones
US3631176A (en) 1970-07-20 1971-12-28 Du Pont Carbamoyl substituted 2-aminobenzimidazoles
US3657443A (en) 1969-09-29 1972-04-18 Du Pont 2-benzimidazolecarbamic acid alkyl esters as foliar fungicides
GB1312536A (en) 1970-10-06 1973-04-04 Rhone Poulenc Sa Hydantoin derivatives
BE793867A (en) 1972-01-11 1973-07-10 Bayer Ag New derivatives of 1,2,4-triazoles, their process for the preparation and their use as fungicides
DE2207576A1 (en) 1972-02-18 1973-08-23 Basf Ag oxazolidine
DE2324020A1 (en) 1972-05-26 1973-12-06 Stauffer Chemical Co Non-terpenoid, the juvenile hormone mimetic compounds and their use for insektenbekaempfung
DE2324010A1 (en) 1973-05-12 1975-01-16 Bayer Ag Triazolyl 0, n-acetals, process for their production and their fungicidal use
GB1394373A (en) 1972-05-17 1975-05-14 Pfizer Ltd Control of plant diseases
FR2254276A1 (en) 1973-12-14 1975-07-11 Pepro
US3903090A (en) 1969-03-19 1975-09-02 Sumitomo Chemical Co Novel n-(3,5-dihalophenyl)-imide compounds
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US3937840A (en) 1973-08-18 1976-02-10 Kumiai Chemical Industry Co., Ltd. Compositions and methods of combatting bacteria and fungi using 2-methylbenzanilide derivatives
BE835579A (en) 1974-11-18 1976-05-14 A process for the preparation of novel 1 - (beta - aryl) ethyl - 1H - 1,2,4 - triazole ketals
US3957847A (en) 1974-03-21 1976-05-18 E. I. Du Pont De Nemours And Company 2-cyano-2-hydroxyiminoacetamides as plant disease control agents
US3991071A (en) 1973-06-21 1976-11-09 The Boots Company Limited Fungicidal compositions containing substituted imidazoles
GB1467561A (en) 1974-01-14 1977-03-16 Sumitomo Chemical Co Phosphorothioates processes for producing them and fungicidal compositions containing them
US4052395A (en) 1975-09-11 1977-10-04 Sankyo Company Limited Agricultural fungicidal compositions containing 6-(substituted phenyl)-pyridazinones and said pyridazinones
DE2732257A1 (en) 1976-07-20 1978-01-26 Nihon Tokushu Noyaku Seizo Kk New ureas or thioureas, processes for their manufacture and their use as fungicides
GB1500581A (en) 1974-04-09 1978-02-08 Ciba Geigy Ag Substituted amides and their use as fungicides
DE2752096A1 (en) 1976-11-22 1978-06-01 Hoffmann La Roche heterocyclic compounds
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
DE2903612A1 (en) 1978-02-02 1979-08-09 Montedison Spa New acylanilines whose production and their use as fungicides
JPS54119462A (en) 1978-03-10 1979-09-17 Nippon Soda Co Ltd Imidazole derivative, its preparation and biocides for agruculture and floriculture containing the same
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
EP0015756A1 (en) 1979-03-07 1980-09-17 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
GB2058059A (en) 1979-08-16 1981-04-08 Sandoz Ltd Novel N-acylamino-2-oxo-3- oxazolidine derivatives and their use as fungicides
DD151404A1 (en) 1980-06-13 1981-10-21 Friedrich Franke Fungicidal agents
EP0040345A1 (en) 1980-05-16 1981-11-25 Bayer Ag 1-Hydroxyethyl-azole derivatives, process for their preparation and their use in the regulation of plant growth and as fungicides
EP0049854A2 (en) 1980-10-10 1982-04-21 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Pyridine and pyrazine derivatives, preparation of these compounds, fungicidal agents containing these compounds as active ingredients, and the use of such compounds or agents as fungicides in agriculture and in horticulture
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
GB2098607A (en) 1981-05-12 1982-11-24 Ciba Geigy Ag Novel microbicidal arylphenyl ether derivatives
EP0078663A2 (en) 1981-10-29 1983-05-11 Sumitomo Chemical Company, Limited Fungicidal N-phenylcarbamates
EP0120321A1 (en) 1983-02-28 1984-10-03 Shell Agrar GmbH & Co. KG Acrylic-acid amides, their preparation and use
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 SHIONOGI & CO., LTD. Azolyl cycloalkanol derivatives and agricultural fungicides
EP0196038A2 (en) 1985-03-29 1986-10-01 BASF Aktiengesellschaft Azolyl methyl oxiranes, their preparation and use as plant-protecting agents
US4664696A (en) 1983-03-04 1987-05-12 Sandoz Ltd. α-phenyl- or benzyl-α-cyclopropylalkylene-1H-imidazole- and 1,2,4-triazole-1-ethanols and use against fungus
EP0224339A2 (en) 1985-10-30 1987-06-03 Kumiai Chemical Industry Co., Ltd. Pyrimidine derivative, process for preparing same and agricultural or horticultural fungicidal composition containing same
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0234242A2 (en) 1986-01-23 1987-09-02 MONTEDIPE S.r.l. Fungicidal azolyl-derivatives
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
EP0253213A1 (en) 1986-07-16 1988-01-20 BASF Aktiengesellschaft Oximethers and fungicides containing them
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0262393A1 (en) 1986-08-29 1988-04-06 Shell Internationale Research Maatschappij B.V. Derivatives of aryloxycarbonic acids, their preparation and their use
EP0267778A2 (en) 1986-11-10 1988-05-18 Kureha Kagaku Kogyo Kabushiki Kaisha Azole derivatives useful in controlling plant diseases and regulating plant growth
EP0278595A2 (en) 1987-02-09 1988-08-17 Zeneca Limited Fungicides
EP0281842A1 (en) 1987-03-07 1988-09-14 Bayer Ag Aminomethyl-heterocycles
WO1988007815A1 (en) * 1987-04-06 1988-10-20 Cpc International, Inc. Method for regulating plant growth
EP0310550A1 (en) 1987-09-28 1989-04-05 Ciba-Geigy Ag Pesticide
JPH01104514A (en) 1987-10-16 1989-04-21 Yoshitaka Aoyama Parts feeder
FR2641277A1 (en) 1988-12-29 1990-07-06 Rhone Poulenc Agrochimie Azolylmethylcyclopentanebenzylidene or -cyclopentenebenzylidene and use as fungicide
EP0382375A2 (en) 1989-02-10 1990-08-16 Zeneca Limited Fungicides
EP0398692A2 (en) 1989-05-17 1990-11-22 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Alkoxyiminoacetamide derivatives and their use as fungicides
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
WO1991013546A1 (en) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Water-dispersible or water-soluble pesticide granules from heat-activated binders
EP0460575A1 (en) 1990-06-05 1991-12-11 Ciba-Geigy Ag Aromatic compounds
EP0472996A1 (en) 1990-08-25 1992-03-04 Bayer Ag Substituted valinamide derivatives
EP0477631A1 (en) 1990-09-22 1992-04-01 BASF Aktiengesellschaft Ortho substituted phenylacetic acid amides
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
EP0545099A2 (en) 1991-11-22 1993-06-09 BASF Aktiengesellschaft Anilide derivatives and their use to combat Botrytis
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
US5240940A (en) 1988-01-29 1993-08-31 Dowelanco Quinoline and cinnoline fungicide compositions
EP0639574A1 (en) 1993-08-16 1995-02-22 Lucky Ltd. 2-aminothiazolecarboxamide derivatives, processes for their preparation and their use for controlling phytopathogenic organisms
WO1996001256A1 (en) 1994-07-06 1996-01-18 Basf Aktiengesellschaft Use of 2-[(dihydro)pyrazolyl-3'-oxymethylene]-anilides as pest-control agents and fungicides
EP0707445A1 (en) 1993-07-03 1996-04-24 Basf Ag Stable, ready-to-use, multi-phase aqueous pesticide formulations and methods of preparing them
WO1996016048A1 (en) 1994-11-21 1996-05-30 Bayer Aktiengesellschaft Microbicidal triazolyl derivatives
WO1996019442A1 (en) 1994-12-19 1996-06-27 Nippon Soda Co., Ltd. Benzamidoxime derivative, process for production thereof, and agrohorticultural bactericide
WO1997015552A1 (en) 1995-10-23 1997-05-01 Basf Aktiengesellschaft Phenylacetic acid derivatives, process and intermediate products for use in producing them and agents containing them
WO1997027189A1 (en) 1996-01-22 1997-07-31 Bayer Aktiengesellschaft Halogen pyrimidines and its use thereof as parasite abatement means
JPH09323984A (en) 1996-06-04 1997-12-16 Ihara Chem Ind Co Ltd Amino acid amide derivative and germicide for agriculture and horticulture
WO1997048684A1 (en) 1996-06-18 1997-12-24 E.I. Du Pont De Nemours And Company Preparation of fungicidal quinazolinones and useful intermediates
JPH10130268A (en) 1996-10-29 1998-05-19 Mitsui Chem Inc Substituted thiophene derivative and agricultural and horticultural fungicide comprising the same as active ingredient
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
EP0860438A1 (en) 1997-02-21 1998-08-26 Shenyang Research Institute of Chemical Industry Fluorine-containing diphenyl acrylamide antimicrobial agents
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
EP0936213A1 (en) 1998-02-10 1999-08-18 Rohm And Haas Company Unsaturated oxime ethers and their use as fungicides and insecticides
WO1999042447A1 (en) 1998-02-19 1999-08-26 Aventis Cropscience Uk Limited 2-pyridylmethylamine derivatives useful as fungicides
US5945567A (en) 1997-08-20 1999-08-31 American Cyanamid Company Fungicidal 2-methoxybenzophenones
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
EP1201648A1 (en) 1999-08-05 2002-05-02 IHARA CHEMICAL INDUSTRY Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2006006878A1 (en) * 2004-07-09 2006-01-19 The Horticulture And Food Research Institute Of New Zealand Limited Fungicidal compositions
WO2006006788A1 (en) 2004-07-08 2006-01-19 Lg Electronics Inc. Washing machine and method for supplying water thereof
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
CN1939128A (en) 2005-09-27 2007-04-04 中国农业大学 Agricultural bacteriocide-P3rimorph
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
KR20080009479A (en) * 2006-07-24 2008-01-29 정병윤 The eco-friendly preventive composition of vermin and disease in the crops
US20090082253A1 (en) 2007-09-17 2009-03-26 Purac Biochem B.V. Antibacterial agent based on fatty acid esters of hydroxy carboxylic acid acids
WO2009092787A1 (en) 2008-01-25 2009-07-30 Purac Biochem Bv Lactylates for the prevention and treatment of infections caused by gram-positive bacteria in animals

Patent Citations (158)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1972961A (en) 1931-05-26 1934-09-11 Du Pont Disinfectant
DE682048C (en) 1932-12-23 1939-10-06 Ig Farbenindustrie Ag Soil treatment agent for combating fungal plant Saddle Edlingen
DE642532C (en) 1934-06-30 1937-03-08 Ig Farbenindustrie Ag Means for fighting of Pilzschaedigungen in orchards
US2317765A (en) 1941-08-20 1943-04-27 Rohm & Haas Fungicidal composition
US2457674A (en) 1944-12-02 1948-12-28 Rohm & Haas Fungicidal compositions
US2504404A (en) 1946-06-12 1950-04-18 Du Pont Manganous ethylene bis-dithiocarbamate and fungicidal compositions containing same
US2526660A (en) 1946-07-06 1950-10-24 Rohm & Haas Capryldintrophenyl crotonate
US2553770A (en) 1948-05-18 1951-05-22 Standard Oil Dev Co Parasiticidal compounds containing the nsccll3 group
US3499086A (en) 1953-07-03 1970-03-03 Hoechst Ag Methods and compositions for controlling fungal and bacterial infestation of plants utilizing organic tetravalent tin compounds
US2720480A (en) 1953-07-17 1955-10-11 Ethyl Corp Fungicidal compositions and method of using same
US2791605A (en) 1954-07-28 1957-05-07 Stauffer Chemical Co Stabilization of salts of monoalkyldithiocarbamic acids
US3248400A (en) 1957-08-17 1966-04-26 Basf Ag Fungicidal agents containing dithiocarbamate and thiuram disulfide radicals
GB857383A (en) 1957-10-26 1960-12-29 Merck Ag E New dithia-anthracene derivatives and fungicidal compositions containing them
US3017415A (en) 1960-01-18 1962-01-16 Merck & Co Inc Certain benzimidazoles carrying thiazolyl, thiadiazolyl and isothiazolyl substituents in the 2 position
DE1193498B (en) 1960-11-03 1965-05-26 Bayer Ag A process for preparing Sulfensaeurederivaten
BE611960A (en) 1960-12-28 1962-07-27
DE1164152B (en) 1961-02-22 1964-02-27 Basf Ag antifungal agents
DE1198125B (en) 1961-02-22 1965-08-05 Basf Ag antifungal agents
GB996264A (en) 1961-05-09 1965-06-23 Rohm & Haas Metal bisdithiocarbamate complexes
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3290353A (en) 1963-04-01 1966-12-06 Diamond Alkali Co Halogenated aromatic nitriles
DE1209799B (en) 1964-05-14 1966-01-27 Bayer Ag Dressers against Fusarium
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
GB1115480A (en) 1964-08-26 1968-05-29 Patterson Co C Improvements relating to the control of micro organisms
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3249499A (en) 1965-04-26 1966-05-03 Us Rubber Co Control of plant diseases
DE1493736A1 (en) 1965-08-26 1969-04-03 Bayer Ag A process for preparing Dithiolphosphorsaeuretriestern
US3399214A (en) 1965-11-05 1968-08-27 Uniroyal Inc Oxides of carboxamido oxathiins
DE1567169A1 (en) 1966-12-17 1970-08-06 Schering Ag Fungicides and fungistatic agents
GB1218623A (en) 1967-04-27 1971-01-06 Lilly Co Eli Susbtituted-5-pyrimidine compounds
DE1643347A1 (en) 1967-08-23 1971-05-27 Bayer Ag A process for the preparation of aromatic lactones
DE1901421A1 (en) 1968-01-23 1969-08-28 Boehringer Sohn Ingelheim diaminocompounds
DE1930540A1 (en) 1968-06-18 1970-01-08 Nippon Soda Co Thioureidobenzole and processes for their preparation
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US3903090A (en) 1969-03-19 1975-09-02 Sumitomo Chemical Co Novel n-(3,5-dihalophenyl)-imide compounds
US3657443A (en) 1969-09-29 1972-04-18 Du Pont 2-benzimidazolecarbamic acid alkyl esters as foliar fungicides
US3631176A (en) 1970-07-20 1971-12-28 Du Pont Carbamoyl substituted 2-aminobenzimidazoles
GB1312536A (en) 1970-10-06 1973-04-04 Rhone Poulenc Sa Hydantoin derivatives
BE793867A (en) 1972-01-11 1973-07-10 Bayer Ag New derivatives of 1,2,4-triazoles, their process for the preparation and their use as fungicides
DE2207576A1 (en) 1972-02-18 1973-08-23 Basf Ag oxazolidine
GB1394373A (en) 1972-05-17 1975-05-14 Pfizer Ltd Control of plant diseases
DE2324020A1 (en) 1972-05-26 1973-12-06 Stauffer Chemical Co Non-terpenoid, the juvenile hormone mimetic compounds and their use for insektenbekaempfung
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
DE2324010A1 (en) 1973-05-12 1975-01-16 Bayer Ag Triazolyl 0, n-acetals, process for their production and their fungicidal use
US3991071A (en) 1973-06-21 1976-11-09 The Boots Company Limited Fungicidal compositions containing substituted imidazoles
US3937840A (en) 1973-08-18 1976-02-10 Kumiai Chemical Industry Co., Ltd. Compositions and methods of combatting bacteria and fungi using 2-methylbenzanilide derivatives
FR2254276A1 (en) 1973-12-14 1975-07-11 Pepro
GB1467561A (en) 1974-01-14 1977-03-16 Sumitomo Chemical Co Phosphorothioates processes for producing them and fungicidal compositions containing them
US3957847A (en) 1974-03-21 1976-05-18 E. I. Du Pont De Nemours And Company 2-cyano-2-hydroxyiminoacetamides as plant disease control agents
GB1500581A (en) 1974-04-09 1978-02-08 Ciba Geigy Ag Substituted amides and their use as fungicides
BE835579A (en) 1974-11-18 1976-05-14 A process for the preparation of novel 1 - (beta - aryl) ethyl - 1H - 1,2,4 - triazole ketals
US4052395A (en) 1975-09-11 1977-10-04 Sankyo Company Limited Agricultural fungicidal compositions containing 6-(substituted phenyl)-pyridazinones and said pyridazinones
DE2732257A1 (en) 1976-07-20 1978-01-26 Nihon Tokushu Noyaku Seizo Kk New ureas or thioureas, processes for their manufacture and their use as fungicides
DE2752096A1 (en) 1976-11-22 1978-06-01 Hoffmann La Roche heterocyclic compounds
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
DE2903612A1 (en) 1978-02-02 1979-08-09 Montedison Spa New acylanilines whose production and their use as fungicides
JPS54119462A (en) 1978-03-10 1979-09-17 Nippon Soda Co Ltd Imidazole derivative, its preparation and biocides for agruculture and floriculture containing the same
EP0015756A1 (en) 1979-03-07 1980-09-17 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
GB2058059A (en) 1979-08-16 1981-04-08 Sandoz Ltd Novel N-acylamino-2-oxo-3- oxazolidine derivatives and their use as fungicides
EP0040345A1 (en) 1980-05-16 1981-11-25 Bayer Ag 1-Hydroxyethyl-azole derivatives, process for their preparation and their use in the regulation of plant growth and as fungicides
DD151404A1 (en) 1980-06-13 1981-10-21 Friedrich Franke Fungicidal agents
EP0049854A2 (en) 1980-10-10 1982-04-21 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Pyridine and pyrazine derivatives, preparation of these compounds, fungicidal agents containing these compounds as active ingredients, and the use of such compounds or agents as fungicides in agriculture and in horticulture
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
GB2098607A (en) 1981-05-12 1982-11-24 Ciba Geigy Ag Novel microbicidal arylphenyl ether derivatives
EP0078663A2 (en) 1981-10-29 1983-05-11 Sumitomo Chemical Company, Limited Fungicidal N-phenylcarbamates
EP0120321A1 (en) 1983-02-28 1984-10-03 Shell Agrar GmbH & Co. KG Acrylic-acid amides, their preparation and use
US4664696A (en) 1983-03-04 1987-05-12 Sandoz Ltd. α-phenyl- or benzyl-α-cyclopropylalkylene-1H-imidazole- and 1,2,4-triazole-1-ethanols and use against fungus
EP0141317A2 (en) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them
EP0152031A2 (en) 1984-02-03 1985-08-21 SHIONOGI & CO., LTD. Azolyl cycloalkanol derivatives and agricultural fungicides
EP0196038A2 (en) 1985-03-29 1986-10-01 BASF Aktiengesellschaft Azolyl methyl oxiranes, their preparation and use as plant-protecting agents
EP0224339A2 (en) 1985-10-30 1987-06-03 Kumiai Chemical Industry Co., Ltd. Pyrimidine derivative, process for preparing same and agricultural or horticultural fungicidal composition containing same
EP0226917A1 (en) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Acrylic acid esters and fungicides containing these compounds
EP0234242A2 (en) 1986-01-23 1987-09-02 MONTEDIPE S.r.l. Fungicidal azolyl-derivatives
EP0243970A1 (en) 1986-05-02 1987-11-04 Stauffer Chemical Company Fungicidal pyridyl imidates
EP0253213A1 (en) 1986-07-16 1988-01-20 BASF Aktiengesellschaft Oximethers and fungicides containing them
EP0256503A2 (en) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Pyridinecarboxamide derivatives and their use as fungicide
EP0262393A1 (en) 1986-08-29 1988-04-06 Shell Internationale Research Maatschappij B.V. Derivatives of aryloxycarbonic acids, their preparation and their use
EP0267778A2 (en) 1986-11-10 1988-05-18 Kureha Kagaku Kogyo Kabushiki Kaisha Azole derivatives useful in controlling plant diseases and regulating plant growth
EP0278595A2 (en) 1987-02-09 1988-08-17 Zeneca Limited Fungicides
EP0281842A1 (en) 1987-03-07 1988-09-14 Bayer Ag Aminomethyl-heterocycles
WO1988007815A1 (en) * 1987-04-06 1988-10-20 Cpc International, Inc. Method for regulating plant growth
EP0310550A1 (en) 1987-09-28 1989-04-05 Ciba-Geigy Ag Pesticide
JPH01104514A (en) 1987-10-16 1989-04-21 Yoshitaka Aoyama Parts feeder
US5240940A (en) 1988-01-29 1993-08-31 Dowelanco Quinoline and cinnoline fungicide compositions
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
FR2641277A1 (en) 1988-12-29 1990-07-06 Rhone Poulenc Agrochimie Azolylmethylcyclopentanebenzylidene or -cyclopentenebenzylidene and use as fungicide
EP0382375A2 (en) 1989-02-10 1990-08-16 Zeneca Limited Fungicides
EP0398692A2 (en) 1989-05-17 1990-11-22 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Alkoxyiminoacetamide derivatives and their use as fungicides
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
EP0428941A1 (en) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Hexahydrotriazine compounds and insecticides
WO1991013546A1 (en) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Water-dispersible or water-soluble pesticide granules from heat-activated binders
EP0460575A1 (en) 1990-06-05 1991-12-11 Ciba-Geigy Ag Aromatic compounds
EP0472996A1 (en) 1990-08-25 1992-03-04 Bayer Ag Substituted valinamide derivatives
EP0477631A1 (en) 1990-09-22 1992-04-01 BASF Aktiengesellschaft Ortho substituted phenylacetic acid amides
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
EP0532022A1 (en) 1991-09-13 1993-03-17 Ube Industries, Ltd. Acrylate compound, preparation process thereof and fungicide using the same
EP0545099A2 (en) 1991-11-22 1993-06-09 BASF Aktiengesellschaft Anilide derivatives and their use to combat Botrytis
EP0707445A1 (en) 1993-07-03 1996-04-24 Basf Ag Stable, ready-to-use, multi-phase aqueous pesticide formulations and methods of preparing them
EP0639574A1 (en) 1993-08-16 1995-02-22 Lucky Ltd. 2-aminothiazolecarboxamide derivatives, processes for their preparation and their use for controlling phytopathogenic organisms
WO1996001256A1 (en) 1994-07-06 1996-01-18 Basf Aktiengesellschaft Use of 2-[(dihydro)pyrazolyl-3'-oxymethylene]-anilides as pest-control agents and fungicides
WO1996016048A1 (en) 1994-11-21 1996-05-30 Bayer Aktiengesellschaft Microbicidal triazolyl derivatives
WO1996019442A1 (en) 1994-12-19 1996-06-27 Nippon Soda Co., Ltd. Benzamidoxime derivative, process for production thereof, and agrohorticultural bactericide
WO1997015552A1 (en) 1995-10-23 1997-05-01 Basf Aktiengesellschaft Phenylacetic acid derivatives, process and intermediate products for use in producing them and agents containing them
WO1997027189A1 (en) 1996-01-22 1997-07-31 Bayer Aktiengesellschaft Halogen pyrimidines and its use thereof as parasite abatement means
JPH09323984A (en) 1996-06-04 1997-12-16 Ihara Chem Ind Co Ltd Amino acid amide derivative and germicide for agriculture and horticulture
WO1997048684A1 (en) 1996-06-18 1997-12-24 E.I. Du Pont De Nemours And Company Preparation of fungicidal quinazolinones and useful intermediates
JPH10130268A (en) 1996-10-29 1998-05-19 Mitsui Chem Inc Substituted thiophene derivative and agricultural and horticultural fungicide comprising the same as active ingredient
DE19650197A1 (en) 1996-12-04 1998-06-10 Bayer Ag 3-thiocarbamoylpyrazole derivatives
EP0860438A1 (en) 1997-02-21 1998-08-26 Shenyang Research Institute of Chemical Industry Fluorine-containing diphenyl acrylamide antimicrobial agents
WO1998046608A1 (en) 1997-04-14 1998-10-22 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
US5945567A (en) 1997-08-20 1999-08-31 American Cyanamid Company Fungicidal 2-methoxybenzophenones
WO1999014187A1 (en) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Benzamidoxim derivatives, intermediate products and methods for preparing and using them as fungicides
WO1999024413A2 (en) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Isothiazole carboxylic acid amides and the application thereof in order to protect plants
WO1999027783A1 (en) 1997-12-04 1999-06-10 Dow Agrosciences Llc Fungicidal compositions and methods, and compounds and methods for the preparation thereof
EP0936213A1 (en) 1998-02-10 1999-08-18 Rohm And Haas Company Unsaturated oxime ethers and their use as fungicides and insecticides
WO1999042447A1 (en) 1998-02-19 1999-08-26 Aventis Cropscience Uk Limited 2-pyridylmethylamine derivatives useful as fungicides
WO2000029404A1 (en) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultura/horticultural bactericides
EP1028125A1 (en) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptide compounds having fungicidal activity and their agronomic use
WO2000046148A1 (en) 1999-02-02 2000-08-10 Sintokogio, Ltd. Silica gel carrying titanium oxide photocatalyst in high concentration and method for preparation thereof
EP1035122A1 (en) 1999-03-11 2000-09-13 Rohm And Haas Company Heterocyclic subsituted isoxazolidines and their use as fungicides
WO2000065913A1 (en) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Sulfonamide derivatives
EP1201648A1 (en) 1999-08-05 2002-05-02 IHARA CHEMICAL INDUSTRY Co., Ltd. Carbamate derivatives and agricultural/horticultural bactericides
DE10021412A1 (en) 1999-12-13 2001-06-21 Bayer Ag Fungicidal active ingredient combinations
WO2001054501A2 (en) 2000-01-25 2001-08-02 Syngenta Participations Ag Herbicidal composition
WO2001056358A2 (en) 2000-01-28 2001-08-09 Rohm And Haas Company Enhanced propertied pesticides
EP1122244A1 (en) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Uracil compounds and their use
WO2002022583A2 (en) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl amides and imides for use as fungicides
WO2002040431A2 (en) 2000-11-17 2002-05-23 Dow Agrosciences Llc Compounds having fungicidal activity and processes to make and use same
JP2002316902A (en) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd Plant blight-preventing agent composition
WO2003010149A1 (en) 2001-07-25 2003-02-06 Bayer Cropscience Ag Pyrazolylcarboxanilides as fungicides
WO2003011853A1 (en) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates and their use as herbicides
WO2003014103A1 (en) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Iodobenzopyran-4-one derivatives having fungicidal activity
WO2003016286A1 (en) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
WO2003053145A1 (en) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Bactericidal composition
WO2003061388A1 (en) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Fused heterocyclic sulfonylurea compound, herbicide containing the same, and method of controlling weed with the same
WO2003066609A1 (en) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Disubstituted thiazolyl carboxanilides and their use as microbicides
WO2003074491A1 (en) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyl-carboxanilides and their use as fungicides
WO2004049804A2 (en) 2002-11-29 2004-06-17 Syngenta Participations Ag Fungicidal combinations for crop potection
WO2004083193A1 (en) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Amide compound and bactericide composition containing the same
WO2005063721A1 (en) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Herbicidal pyrimidines
WO2005087773A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005087772A1 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
WO2005120234A2 (en) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds
WO2005123689A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide
WO2005123690A1 (en) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-difluoromethyl-pyrazol-4-carbonic acid-(ortho-phenyl)-anilides, and use thereof as a fungicide
WO2006006788A1 (en) 2004-07-08 2006-01-19 Lg Electronics Inc. Washing machine and method for supplying water thereof
WO2006006878A1 (en) * 2004-07-09 2006-01-19 The Horticulture And Food Research Institute Of New Zealand Limited Fungicidal compositions
WO2006015866A1 (en) 2004-08-12 2006-02-16 Syngenta Participations Ag Method for protecting useful plants or plant propagation material
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
WO2006087325A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said substances
DE102005009458A1 (en) 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
CN1939128A (en) 2005-09-27 2007-04-04 中国农业大学 Agricultural bacteriocide-P3rimorph
WO2007082098A2 (en) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2007090624A2 (en) 2006-02-09 2007-08-16 Syngenta Participations Ag A method of protecting a plant propagation material, a plant, and/or plant organs
KR20080009479A (en) * 2006-07-24 2008-01-29 정병윤 The eco-friendly preventive composition of vermin and disease in the crops
US20090082253A1 (en) 2007-09-17 2009-03-26 Purac Biochem B.V. Antibacterial agent based on fatty acid esters of hydroxy carboxylic acid acids
WO2009092787A1 (en) 2008-01-25 2009-07-30 Purac Biochem Bv Lactylates for the prevention and treatment of infections caused by gram-positive bacteria in animals

Non-Patent Citations (31)

* Cited by examiner, † Cited by third party
Title
"Perry' s Chemical Engineer' s Handbook, 4th Ed.,", 1963, MCGRAW-HILL, pages: 8 - 57
"Pesticide Manual", 2000, pages: 712
"The British Crop Protection Council,10th ed.", 1995, pages: 482
"The Pesticide Manual, publ.", 1995, THE BRITISH CROP PROTECTION COUNCIL, 10TH ED., pages: 474
AGRIC. BIOL. CHEM., vol. 37, 1973, pages 737
BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 December 1967 (1967-12-04), pages 147 - 48
BULL. SOC. CHIM. FR., vol. 15, 1897, pages 891
C. R. SEANCES, ACAD. AGRIC. FR., vol. 31, 1945, pages 24
CAN. J. PLANT SCI., vol. 48, no. 6, 1968, pages 587 - 94
COLBY, S. R.: "Calculating synergistic and antagonistic responses of herbicide combinations", WEEDS, vol. 15, 1967, pages 20 - 22
COLBY, S.R.: "Calculating synergistic and antagonistic responses of herbicide combinations", WEEDS, vol. 15, 1967, pages 20 - 22
CONGR. PLANT PATHOL., vol. 1, 1968, pages 27
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 2008, JUNG, BYEONG YUN: "Environment-friendly composition for preventing pests and diseases in crops", XP002566290, retrieved from STN Database accession no. 148:278298 *
FRUITS, vol. 28, 1973, pages 545
HANCE ET AL.: "Weed Control Handbook", 1989, BLACKWELL SCIENTIFIC
J. AM. CHEM. SOC., vol. 69, 1947, pages 1234
KLINGMAN: "Weed Control as a Science", 1961, J. WILEY & SONS
MOLLET, H.; GRUBEMANN, A.: "Formulation technology", 2001, WILEY VCH VERLAG
NOYAKU KAGAKU, vol. 8, 1983, pages 575
PHYTOPATHOLOGY, vol. 52, 1962, pages 754
PLANT DIS. REP., vol. 41, 1957, pages 1029
PROC. 1988 BR. CROP PROT. CONF. - PESTS DIS., vol. 1, 1988, pages 33
PROC. 1988 BR. CROP PROT. CONF. - PESTS DIS., vol. 1, 1988, pages 65
PROC. 1990 BR. CROP. PROT. CONF. - PESTS DIS., vol. 1, 1990, pages 459
PROC. BR. CROP PROT. CONF. - PESTS DIS., vol. 2, 1998, pages 327
PROC. BR. CROP PROT. CONF.-PESTS DIS., vol. 1, 1984, pages 413
PROC. BR. CROP PROT. CONF.-PESTS DIS., vol. 5-3, 1992, pages 411
PROC. BR. INSECTIC. FUNGIC. CONF. 7., vol. 2, 1973, pages 673
PROC. INSECTIC. FUNGIC. CONF. 8., vol. 2, 1975, pages 715
R.S. COLBY, WEEDS, vol. 15, 1967, pages 20 - 22
TAMMES, P. M. L.: "Isoboles, a graphic representation of synergism in pesticides", NETHERL. J. PLANT PATHOL., 1964, pages 70

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013007558A3 (en) * 2011-07-08 2013-04-04 Purac Biochem Bv Active formulation for use in feed products
CN103732077A (en) * 2011-07-08 2014-04-16 普拉克生化公司 Active formulation for use in feed products
JP2014520518A (en) * 2011-07-08 2014-08-25 ピュラック バイオケム ビー. ブイ. Active composition for use in feed products
RU2603915C2 (en) * 2011-07-08 2016-12-10 ПУРАК Биокем БВ Active composition for use in fodder products
US9849105B2 (en) 2011-07-08 2017-12-26 Purac Biochem Bv Active formulation for use in feed products
WO2016121354A1 (en) * 2015-01-26 2016-08-04 国立研究開発法人農業・食品産業技術総合研究機構 Soil-borne disease control method, soil for plant cultivation use, and soil-borne disease control agent
CN105251497A (en) * 2015-09-28 2016-01-20 江苏七洲绿色化工股份有限公司 Solid catalyst, and preparation method and applications thereof
CN105494387A (en) * 2015-12-16 2016-04-20 江苏辉丰农化股份有限公司 Pesticide composition
CN107047576A (en) * 2017-03-07 2017-08-18 南京华洲药业有限公司 Sterilizing compound containing fluoxastrobin and kresoxim-methyl and application thereof

Similar Documents

Publication Publication Date Title
RU2428838C2 (en) Fungicide combinations of biologically active substances that contain fluoxastrobin
CA2753150C (en) Use of synthetic and biological fungicides in combination for controlling harmful fungi
JP4589959B2 (en) Plant disease controlling composition and method control
US7598206B2 (en) Fungicidal mixtures
JP5670328B2 (en) Pesticidal mixtures comprising isoxazoline compounds ii
US8349877B2 (en) Ternary fungicidal compositions comprising boscalid and chlorothalonil
JP5227950B2 (en) Use of aryl acid biphenylamide for seed treatment
JP6002034B2 (en) Methods for increasing the vigor and / or crop yield of agricultural crops in the essentially non-presence of pathogens pressure
CN101410016B (en) Fungicidal compositions
RU2370034C2 (en) Triple fungicide combination of bioactive substances
US20130130898A1 (en) Fungicidal Compositions
RU2331192C2 (en) Fungicidal combination of active agents
ES2650764T3 (en) Combinations of active compounds containing a fungicide and tiazolilisoxazolina
JP5122452B2 (en) Fungicidal mixtures based on Asolo pyrimidinylamine
US20120245031A1 (en) Pesticidal Mixtures
JP5618479B2 (en) Fungicidal mixture comprising a substituted 1-methyl-4-yl carboxylate anilide compounds
CN1946294B (en) Pesticidal composition and method for fungal control
US8404263B2 (en) Agrochemical formulations comprising a pesticide, an organic UV-photoprotective filter and coated metal-oxide nanoparticles
WO2012084670A1 (en) Pesticidal active mixtures comprising pyrazole compounds
WO2005041653A2 (en) Synergistic fungicidal active combinations
JP5530428B2 (en) Sterilant mixture comprising the substituted l-methyl-5-yl carboxylate anilide
HU0401717A2 (en) fungicidal composition comprising arylamidine derivatives and fungicidal compounds known
CN102014628A (en) Plant health composition
US20090123561A1 (en) Fungicide mixtures based on 1-methyl-pyrazol-4-ylcarboxanilides
CA2739564A1 (en) Method for improving plant health

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10745664

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase in:

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10745664

Country of ref document: EP

Kind code of ref document: A1