WO2011138345A2 - Fungicidal mixtures based on gallic acid esters - Google Patents
Fungicidal mixtures based on gallic acid esters Download PDFInfo
- Publication number
- WO2011138345A2 WO2011138345A2 PCT/EP2011/057081 EP2011057081W WO2011138345A2 WO 2011138345 A2 WO2011138345 A2 WO 2011138345A2 EP 2011057081 W EP2011057081 W EP 2011057081W WO 2011138345 A2 WO2011138345 A2 WO 2011138345A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- iii
- methyl
- alkyl
- triazolo
- pyrimidin
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- 0 *c1n[n]2c(N)c(*)c(*)nc2n1 Chemical compound *c1n[n]2c(N)c(*)c(*)nc2n1 0.000 description 2
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a 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
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a 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 having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
Definitions
- the present invention relates to a fungicidal mixture comprising, as active components: 1 ) gallic acid esters of the formula I
- Y is Ci-Ci2-alkyl
- At least one active compound II selected from the following groups
- R 1 is C3-Ci2-alkyl, C2-Ci2-alkenyl, C5-Ci2-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-Ci-C4-alkyl;
- R 2 is Ci-Ci2-alkyl, C 2 -Ci 2 -alkenyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl; where the aliphatic chains in R 1 and/or R 2 may be substituted by one to four identical or different groups R a :
- R a is halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C3-C8-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C 6 -alkoxy-Ci-C 6 -alkyl or NR A R B ;
- R A , R B are hydrogen and Ci-C6-alkyl
- R 1 and/or R a may be substituted by one to four groups R b :
- R b is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-C6-alkoxy;
- R 3 is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, Ci-C6-alkyl,
- Ci-C6-haloalkyl Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C8-cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl,
- Ci-Cio-alkylcarbonyl Ci-Cio-alkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C2-Cio-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, Ci-C 6 -alkyl-S(0) m -;
- n 0, 1 or 2;
- carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, fluxapyroxad, 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, N-(4'-trifluoromethylthiobi- phenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide and N-(2- (1 ,3,3-
- benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide;
- carpropamid carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide; in a synergistically effective amount.
- the present invention relates to an agrochemical composition, comprising a liquid or solid carrier and the fungicidal mixture.
- the present invention relates to seed, comprising the fungicidal mixture or the composition in an amount of form 1 to 1000 g/100 kg of seed.
- the present invention relates to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the fungicidal mixture or the composition.
- the present invention relates to a method for improving plant health, comprising treating a plant, its propagation material, the lotus where the plant is growing or is to grow with an effective amount of the fungicidal mixture or the composition.
- the fungicidal mixtures comprising compound of the formula I and at least one compound II.
- the mixtures of the compound of the formula I and an active compound II or the simultaneous, that is joint or separate, use of the compounds I and an active compound II are/is distinguished by excellent activity against a broad spectrum of phytopathogenic fungi. Some of them are systemically active and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil fungicides.
- C x -C y denotes the number of possible carbon atoms in the particular case.
- halogen fluorine, bromine, chlorine or iodine, especially fluorine, chlorine or bromine; alkyl and the alkyl moieties of composite groups such as, for example, alkoxy, alkylamino, alkoxycarbonyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 12 carbon atoms, for example Ci-Ci2-akyl, such as methyl, ethyl, propyl, 1 - methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl
- the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluorine, chlorine or bromine.
- a particular halogen atom preferably fluorine, chlorine or bromine.
- the alkyl groups are partially or fully halogenated by different halogen atoms; in the case of mixed halogen
- substitutions the combination of chlorine and fluorine is preferred.
- Particular preference is given to (Ci-C3)-haloalkyl, more preferably (Ci-C2)-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,
- alkenyl and also the alkenyl moieties in composite groups such as alkenyloxy:
- unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one double bond in any position.
- small alkenyl groups such as (C2-C4)-alkenyl
- larger alkenyl groups such as (C5-C8)-alkenyl.
- alkenyl groups are, for example, C2-C6-alkenyl, such as ethenyl, 1 - propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 - propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl,
- alkynyl and the alkynyl moieties in composite groups straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2- propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl,
- cycloalkyl and also the cycloalkyl moieties in composite groups mono- or bicyclic saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, for example C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
- bicyclic radicals comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
- optionally substituted Cs-Cs-cycloalkyl means a cycloalkyl radical having from 3 to 8 carbon atoms, in which at least one hydrogen atom, for example 1 , 2, 3, 4 or 5 hydrogen atoms, is/are replaced by substituents which are inert under the conditions of the reaction.
- substituents which are inert under the conditions of the reaction.
- inert substituents are CN, Ci-C6-alkyl, Ci-C4-haloalkyl, C1-C6- alkoxy, C3-C6-cycloalkyl, and Ci-C4-alkoxy-Ci-C6-alkyl;
- alkoxy an alkyl group as defined above which is attached via an oxygen, preferably having 1 to 8, more preferably 2 to 6, carbon atoms.
- Examples are: methoxy, ethoxy, n- propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1 ,1 - dimethylethoxy, and also for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 - ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4- methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethy
- phenyl-Ci-C6-alkyl Ci-C6-alkyl in which one of the hydrogen atoms is replaced by an optionally substituted phenyl group. Examples are benzyl, 4-methylbenzyl, phenylethyl etc.;
- alkylthio alkyl as defined above which is attached via an S atom
- cycloalkylthio cycloalkyl as defined above which is attached via an S atom;
- hydroxyl OH group which is attached via an O atom
- cyano CN group which is attached via an C atom
- formyl CHO group, which is attached via an C atom;
- gallic acid esters of the formula I referred to above as component 1 , also known as "gallates", are antioxidant compounds widely used in the food, cosmetics and drug industries (Pucci B, et all. Helv. Chim. Acta 2003, 86(2), 247-265). Antifungal activity of octyl gallate is known from Bioorg. Med. Chem. Lett. 2001 ; 12; 1 1 (3); 7-50.
- Many of the gallic acid esters used in the practice of the present invention are commercially available compounds or may be readily synthesized by methods that are well known in the art, for example, by refluxing gallic acid and the appropriate alcohol (R-OH) in the presence of acid using standard conditions.
- the fungicidal mixtures comprise a compound of the formula I, in which Y is:
- fungicidal mixture comprising a compound I, in which A is propyl.
- azolopyrimidin-7-ylamines of the formula III referred to above as component 2, their preparation and their action against harmful fungi are known from the literature (EP-A 71 792; EP-A 141 317; WO 03/009687; WO 05/087771 ; WO 05/087772; WO 05/087773; WO 2005/087772; WO 2006/087325; WO 2006/092428).
- Particularly suitable for the mixtures according to the invention are compounds of the formula III in which R 1 is straight-chain or branched C3-Ci2-alkyl or phenyl which may be substituted by one to three halogen or Ci-C4-alkyl groups.
- the fungicidal mixtures comprise compounds of the formula III in which group R a is absent.
- a preferred embodiment relates the fungicidal mixtures comprising a compound of the formula III in which R 1 is straight-chain or branched Cs-C-io-alkyl, in particular ethyl, 3,5,5-trimethylhexyl, n-heptyl, n-octyl, n-nonyl and n-decyl.
- a further embodiment relates to the fungicidal mixtures comprising a compound of the formula III in which R 1 is phenyl which is unsubstituted or substituted by one to four halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl and Ci-C6-alkoxy groups.
- Preferred compounds of the formula III are those in which R 1 is a substituted phenyl group which corresponds to a group G
- L 1 is cyano, halogen, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkoxy;
- L 2 , L 3 independently of one another are hydrogen or one of the groups mentioned under L 1 and
- # denotes the bond to the azolopyrimidine skeleton.
- L 1 is cyano, halogen, hydroxyl, mercapto, nitro, NR A R B , Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy, preferably cyano, halogen, Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy.
- L 2 is hydrogen or one of the groups mentioned above.
- L 3 is hydrogen, cyano, halogen, hydroxyl, mercapto, nitro, NR A R B , Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy, preferably hydrogen.
- R 2 is straight-chain or branched Ci-Ci2-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl or Ci-C4-haloalkyl.
- R 2 is methyl, ethyl, n-propyl, n-octyl, trifluoromethyl or methoxymethyl, in particular methyl, ethyl, trifluoromethyl or methoxymethyl.
- R 3 is amino
- One embodiment of the compounds of the formula III relates to those in which A is N. These compounds correspond to the formula IIIA in which the variables are as defined for formula III:
- Another embodiment of the compounds of the formula III relates to those in which A is CH. These compounds correspond to the formula NIB in which the variables are as defined for formula III:
- the carbon chains of R 1 and R 2 together do not have more than 12 carbon atoms.
- Preferred embodiments of the mixtures according to the invention comprise, as active component 2, a compound selected from the following list:
- the active compounds II of group B) and C), mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf. Pesticide manuals, http://www.alanwood.net/pesticides/); they are commercially available.
- the active compounds II of group D), mentioned above as component 2, and their preparation have been described in the international non-published applications WO 2009/071448, WO 2009/071449, WO 2009/101078 and WO 2009/101079.
- the fungicidal mixtures comprise as active compound II metrafenone.
- the fungicidal mixtures comprise as active compound I I a compound of group C) selected from: benalaxyl, benalaxyl-M, boscalid , bixafen , fluopyram, fluxapyroxad, isopyrazam, metalaxyl, penflufen, pentihipyrad, sedaxane.
- group C selected from: benalaxyl, benalaxyl-M, boscalid , bixafen , fluopyram, fluxapyroxad, isopyrazam, metalaxyl, penflufen, pentihipyrad, sedaxane.
- the fungicidal mixtures comprise as active compound II boscalid.
- Preferred embodiments relate to the compositions listed in table A, where in each case one row of table A corresponds to a fungicidal composition comprising the particular compound of the formula I mentioned (Component 1 ) and one active compound of the groups mentioned (Component 2), this active compound preferably being selected from the preferred embodiments defined above.
- Table A
- a further embodiment relates to the compositions B-1 to B-165 listed in Table B, where a row of Table B corresponds in each case to a fungicidal composition comprising as component 1 an individualized compound of the formula I and the respective further active substance from groups A) to C) (component 2) stated in the row in question.
- the compositions described comprise the active substances in
- Table B Composition comprising one individualized compound of the formula I and one further active substance from groups A) to C)
- the active compounds mentioned above can also be employed in the form of their agriculturally compatible salts. These are usually the alkali metal or alkaline earth metal salts, such as sodium, potassium or calcium salts.
- the compounds of the formula I and/or the compounds II of the inventive compositions can be present in different crystal modifications, which may differ in biological activity.
- - azoxystrobin coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-[2-
- - carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fen- furam, fenhexamid, flutolanil, fluxapyroxad, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil,
- carpropamid carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
- C) azoles carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
- - triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothio- conazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;
- - 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;
- - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepani- pyrim, nitrapyrin, nuarimol, pyrimethanil;
- 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;
- acibenzolar-S-methyl ametoctradin, amisulbrom, anilazin, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, proquinazid, 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]
- guanidine guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
- antibiotics kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, poly- oxine, validamycin A;
- nitrophenyl derivates: binapacryl, dicloran, dinobuton, dinocap, nitrothal-isopropyl, tecnazen,
- organometal compounds fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
- organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
- organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quinto- zene, thiophanate-methyl, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide;
- Ampelomyces quisqualis e.g. AQ 10 ® from Intrachem Bio GmbH & Co. KG, Germany
- Aspergillus flavus e.g.
- AFLAGUARD ® from Syngenta, CH
- Aureobasidium pullulans e.g. BOTECTOR ® from bio-ferm GmbH, Germany
- Bacillus pumilus e.g. NRRL Accession No. B- 30087 in SONATA ® and BALLAD ® Plus from AgraQuest Inc., USA
- Bacillus subtilis e.g. isolate NRRL-Nr. B-21661 in RHAPSODY ® , SERENADE ® MAX and
- BIOCURE ® in mixture with lysozyme
- BIOCOAT ® from Micro Flo Company, USA (BASF SE) and Arysta
- Chitosan e.g. ARMOUR-ZEN from BotriZen Ltd., NZ
- Clonostachys rosea f. catenulata also named Gliocladium catenulatum (e.g. isolate J1446: PRESTOP ® from Verdera, Finland), Coniothyrium minitans (e.g.
- CONTANS ® from Prophyta, Germany Cryphonectrl-Aparasitica (e.g. Endothl- Aparasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS ® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g. BIOFOX ® from S.I.A.P.A., Italy, FUSACLEAN ® from Natural Plant Protection, France),
- Cryphonectrl-Aparasitica e.g. Endothl- Aparasitica from CNICM, France
- Cryptococcus albidus e.g. YIELD PLUS ® from Anchor Bio-Technologies, South Africa
- Fusarium oxysporum e.g. BIOFOX ® from S.I.A.P.A., Italy, FUSACLEAN ® from Natural Plant Protection, France
- Metschnikowl-Afructicola e.g. SHEMER ® from Agrogreen, Israel
- Microdochium dimerum e.g. ANTIBOT ® from Agrauxine, France
- Phlebiopsis gigantea e.g. ROTSOP ® from Verdera, Finland
- Pseudozyma flocculosa e.g. SPORODEX ® from Plant Products Co. Ltd., Canada
- Pythium oligandrum DV74 e.g. POLYVERSUM ® from Remeslo SSRO, Biopreparaty, Czech Rep.
- Reynoutria sachlinensis e.g. REGALIA ® from Marrone Biolnnovations, USA
- Talaromyces flavus V1 17b e.g.
- PLANTSHIELD ® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO ® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX ® and
- T. harzianum and T. viride e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ
- T. harzianum ICC012 and T. viride ICC080 e.g. REMEDIER ® WP from Isagro Ricerca, Italy
- T. polyspo rum and T. harzianum e.g. BINAB ® from BINAB Bio- Innovation AB, Sweden
- T. stromaticum e.g. TRICOVAB ® from C.E.P.L.A.C.
- T. virens GL-21 e.g. SOILGARD ® from Certis LLC, USA
- T. viride TV1 e.g. T. viride TV1 from Agribiotec srl, Italy
- Ulocladium oudemansii ⁇ RU3 e.g.
- abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dike- gulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthi- acet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
- acetochlor alachlor, butachlor, dimethachlor, dimethenamid
- flufenacet mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
- - aryloxyphenoxypropionates clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
- - (thio)carbamates asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
- acifluorfen acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
- - 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;
- - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
- - sulfonyl ureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl,
- - triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone,
- metamitron metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
- ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
- acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
- amicarbazone amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin,
- organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, 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;
- - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfen- valerate, 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: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etox- azole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
- - GABA antagonist compounds endosulfan, ethiprole, fipronil, vaniliprole,
- - macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
- - mitochondrial electron transport inhibitor I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
- oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
- - moulting disruptor compounds cryomazine; - mixed function oxidase inhibitors: piperonyl butoxide;
- a further embodiment relates to the compositions C-1 to C-1035 listed in Table C, where a row of Table C corresponds in each case to a fungicidal composition
- a fungicidal composition comprising as component 1 an individualized compound of the formula I (l-A, l-B, l-C), as component 2: 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-7) and the respective further active substance (component 3) stated in the row in question.
- compositions described comprise the active substances in
- Table C Composition comprising one individualized compound of the formula I (l-A, l-B or l-C), 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-7) and one further active substance.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Fungicidal mixtures based on gallic acid ester.
Description
Fungicidal mixtures based on gallic acid esters
Description
The present invention relates to a fungicidal mixture comprising, as active components: 1 ) gallic acid esters of the formula I
in which the substituent is as defined below:
Y is Ci-Ci2-alkyl;
and
at least one active compound II selected from the following groups
azolopyrimidinylamines of the formula III,
in which the substituents are as defined below:
R1 is C3-Ci2-alkyl, C2-Ci2-alkenyl, C5-Ci2-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-Ci-C4-alkyl;
R2 is Ci-Ci2-alkyl, C2-Ci2-alkenyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl; where the aliphatic chains in R1 and/or R2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C3-C8-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C6-alkyl or NRARB;
RA, RB are hydrogen and Ci-C6-alkyl;
where the cyclic groups in R1 and/or Ra may be substituted by one to four groups Rb:
Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, Ci-Cio-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-C6-alkoxy;
R3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, Ci-C6-alkyl,
Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C8-cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl,
Ci-Cio-alkylcarbonyl, Ci-Cio-alkoxycarbonyl, C2-Cio-alkenyloxycarbonyl,
C2-Cio-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, Ci-C6-alkyl-S(0)m-;
m is 0, 1 or 2;
Ais CR3 or N
B) metrafenone;
C) carboxamides selected from:
carboxanilides:benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, fluxapyroxad, 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, N-(4'-trifluoromethylthiobi- phenyl-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;
other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide; in a synergistically effective amount.
Furthermore the present invention relates to an agrochemical composition, comprising a liquid or solid carrier and the fungicidal mixture.
Furthermore the present invention relates to seed, comprising the fungicidal mixture or the composition in an amount of form 1 to 1000 g/100 kg of seed.
Furthermore the present invention relates to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the fungicidal mixture or the composition.
Furthermore the present invention relates to a method for improving plant health, comprising treating a plant, its propagation material, the lotus where the plant is growing or is to grow with an effective amount of the fungicidal mixture or the composition.
Mixtures comprising gallic acid esters and some fungicides have been already described in the literature (WO 2008/065527, WO 2008/071714). Further, WO
2005/04404 describes mixtures comprising strobilurins and ethylene modulators such as n-propyl gallate.
Practical agricultural experience has shown that the repeated and exclusive application of an individual active compound in the control of harmful fungi or insects or other pests
leads in many cases to a rapid selection of those fungus strains or pest isolates which have developed natural or adapted resistance against the active compound in question. Effective control of these fungi or pests with the active compound in question is then no longer possible.
To reduce the risk of the selection of resistant fungus strains or insect isolates, mixtures of different active compounds are nowadays conventionally employed for controlling harmful fungi or insects or other pests. By combining active compounds having different mechanisms of action, it is possible to ensure successful control over a relatively long period of time.
It is an object of the present invention to provide, with a view to effective resistance management and effective control of phytopathogenic harmful fungi, insects or other pests, at application rates which are as low as possible, compositions which, at a reduced total amount of active compounds applied, have improved activity against the harmful fungi or pests (synergistic mixtures) and a broadened activty spectrum, in particular for certain indications.
We have accordingly found that this object is achieved by the fungicidal mixtures, defined herein, comprising compound of the formula I and at least one compound II. The mixtures of the compound of the formula I and an active compound II or the simultaneous, that is joint or separate, use of the compounds I and an active compound II are/is distinguished by excellent activity against a broad spectrum of phytopathogenic fungi. Some of them are systemically active and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil fungicides.
The terms used for organic groups in the definition of the variables are, for example the expression "halogen", collective terms which represent the individual members of these groups of organic units.
The prefix Cx-Cy denotes the number of possible carbon atoms in the particular case. halogen: fluorine, bromine, chlorine or iodine, especially fluorine, chlorine or bromine; alkyl and the alkyl moieties of composite groups such as, for example, alkoxy, alkylamino, alkoxycarbonyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 12 carbon atoms, for example Ci-Ci2-akyl, such as methyl, ethyl, propyl, 1 - methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl,1 -ethyl-2-methylpropyl, octyl, dodecyl; haloalkyl: straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above. In one embodiment, the alkyl groups
are substituted at least once or completely by a particular halogen atom, preferably fluorine, chlorine or bromine. In a further embodiment, the alkyl groups are partially or fully halogenated by different halogen atoms; in the case of mixed halogen
substitutions, the combination of chlorine and fluorine is preferred. Particular preference is given to (Ci-C3)-haloalkyl, more preferably (Ci-C2)-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,
1 - chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1 ,1 ,1 -trifl uoroprop-2-yl ;
alkenyl and also the alkenyl moieties in composite groups, such as alkenyloxy:
unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one double bond in any position. According to the invention, it may be preferred to use small alkenyl groups, such as (C2-C4)-alkenyl; on the other hand, it may also be preferred to employ larger alkenyl groups, such as (C5-C8)-alkenyl. Examples of alkenyl groups are, for example, C2-C6-alkenyl, such as ethenyl, 1 - propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 - propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl,
2- pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1 - butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 -methyl-3- butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl-
1 - propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl,
2- hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl-1 -pentenyl, 2-methyl-1 -pentenyl,
3- methyl-1 -pentenyl, 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3- methyl-2-pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-3-pentenyl, 3- methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3- methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1 - butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3- dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1 - butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2-butenyl, 1 -ethyl-3-butenyl,
2- ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 - ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 -propenyl and 1 -ethyl-2-methyl-2- propenyl;
alkynyl and the alkynyl moieties in composite groups: straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2- propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl,
3- pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3- methyl-1 -butynyl, 1 ,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3- hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4-
pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4- pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1 ,1 -dimethyl-2-butynyl, 1 ,1 - dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1 - butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 -ethyl-1 -methyl-2- propynyl;
cycloalkyl and also the cycloalkyl moieties in composite groups: mono- or bicyclic saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, for example C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Examples of bicyclic radicals comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. In this connection, optionally substituted Cs-Cs-cycloalkyl means a cycloalkyl radical having from 3 to 8 carbon atoms, in which at least one hydrogen atom, for example 1 , 2, 3, 4 or 5 hydrogen atoms, is/are replaced by substituents which are inert under the conditions of the reaction. Examples of inert substituents are CN, Ci-C6-alkyl, Ci-C4-haloalkyl, C1-C6- alkoxy, C3-C6-cycloalkyl, and Ci-C4-alkoxy-Ci-C6-alkyl;
alkoxy: an alkyl group as defined above which is attached via an oxygen, preferably having 1 to 8, more preferably 2 to 6, carbon atoms. Examples are: methoxy, ethoxy, n- propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1 ,1 - dimethylethoxy, and also for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 - ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4- methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2- methylpropoxy;
phenyl-Ci-C6-alkyl: Ci-C6-alkyl in which one of the hydrogen atoms is replaced by an optionally substituted phenyl group. Examples are benzyl, 4-methylbenzyl, phenylethyl etc.;
alkylthio: alkyl as defined above which is attached via an S atom;
cycloalkylthio: cycloalkyl as defined above which is attached via an S atom;
hydroxyl: OH group which is attached via an O atom;
cyano: CN group which is attached via an C atom;
formyl: CHO group, which is attached via an C atom;
carboxyl: COOH group, which is attached via an C atom;
mercapto: SH group which is attached via an S atom;
nitro: NO2 group which is attached via an N atom.
The gallic acid esters of the formula I, referred to above as component 1 , also known as "gallates", are antioxidant compounds widely used in the food, cosmetics and drug industries (Pucci B, et all. Helv. Chim. Acta 2003, 86(2), 247-265). Antifungal activity of octyl gallate is known from Bioorg. Med. Chem. Lett. 2001 ; 12; 1 1 (3); 7-50. Many of the gallic acid esters used in the practice of the present invention are commercially available compounds or may be readily synthesized by methods that are well known in the art, for example, by refluxing gallic acid and the appropriate alcohol (R-OH) in the presence of acid using standard conditions.
According to one embodiment of the invention the fungicidal mixtures comprise a compound of the formula I, in which Y is:
propyl (l-A), octyl (l-B) or dodecyl (l-C).
Particular preference is given to the fungicidal mixture comprising a compound I, in which A is propyl.
The azolopyrimidin-7-ylamines of the formula III, referred to above as component 2, their preparation and their action against harmful fungi are known from the literature (EP-A 71 792; EP-A 141 317; WO 03/009687; WO 05/087771 ; WO 05/087772; WO 05/087773; WO 2005/087772; WO 2006/087325; WO 2006/092428).
With a view to the intended use of the azolopyrimidinylamines of the formula III, particular preference is given to the following meanings of the substituents, in each case on their own or in combination:
Particularly suitable for the mixtures according to the invention are compounds of the formula III in which R1 is straight-chain or branched C3-Ci2-alkyl or phenyl which may be substituted by one to three halogen or Ci-C4-alkyl groups.
According to one embodiment of the invention the fungicidal mixtures comprise compounds of the formula III in which group Ra is absent.
A preferred embodiment relates the fungicidal mixtures comprising a compound of the formula III in which R1 is straight-chain or branched Cs-C-io-alkyl, in particular ethyl, 3,5,5-trimethylhexyl, n-heptyl, n-octyl, n-nonyl and n-decyl.
A further embodiment relates to the fungicidal mixtures comprising a compound of the formula III in which R1 is phenyl which is unsubstituted or substituted by one to four halogen, cyano, hydroxyl, mercapto, nitro, NRARB, Ci-Cio-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl and Ci-C6-alkoxy groups.
Preferred compounds of the formula III are those in which R1 is a substituted phenyl group which corresponds to a group G
in which
L1 is cyano, halogen, hydroxyl, mercapto, nitro, NRARB, Ci-Cio-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkoxy; and
L2, L3 independently of one another are hydrogen or one of the groups mentioned under L1 and
# denotes the bond to the azolopyrimidine skeleton.
In a further embodiment of the compounds of the formula III, L1 is cyano, halogen, hydroxyl, mercapto, nitro, NRARB, Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy, preferably cyano, halogen, Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy.
In a further embodiment of the compounds of the formula III, L2 is hydrogen or one of the groups mentioned above.
In a further embodiment of the compounds of the formula III, L3 is hydrogen, cyano, halogen, hydroxyl, mercapto, nitro, NRARB, Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy, preferably hydrogen.
Preference is given to compounds of the formula III in which R2 is straight-chain or branched Ci-Ci2-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl or Ci-C4-haloalkyl.
In a particularly preferred embodiment of the compounds of the formula III, R2 is methyl, ethyl, n-propyl, n-octyl, trifluoromethyl or methoxymethyl, in particular methyl, ethyl, trifluoromethyl or methoxymethyl.
Preference is furthermore given to compounds of the formula III in which R3 is hydrogen.
In a further embodiment of the compounds of the formula III, R3 is amino.
One embodiment of the compounds of the formula III relates to those in which A is N. These compounds correspond to the formula IIIA in which the variables are as defined for formula III:
Another embodiment of the compounds of the formula III relates to those in which A is CH. These compounds correspond to the formula NIB in which the variables are as defined for formula III:
In a further embodiment of preferred compounds III, the carbon chains of R1 and R2 together do not have more than 12 carbon atoms.
Preferred embodiments of the mixtures according to the invention comprise, as active component 2, a compound selected from the following list:
6-(3,4-dichlorophenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (111-1 ),
6-(4-tert-butylphenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-2),
5-methyl-6-(3,5,5-trimethylhexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-3), 5-methyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-4),
5- ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidine-2,7-diamine (III-5),
6- ethyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-6),
5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-7),
5-ethyl-6-(3,5,5-trimethylhexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-8),
6-octyl-5-propyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-9),
5- methoxymethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (111-10),
6- octyl-5-trifluoromethyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (111-1 1 )and
5-trifluoromethyl-6-(3,5,5-trimethylhexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (111-12).
The active compounds II of group B) and C), mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf. Pesticide manuals, http://www.alanwood.net/pesticides/); they are commercially available. The active compounds II of group D), mentioned above as component 2, and their preparation have been described in the international non-published applications WO 2009/071448, WO 2009/071449, WO 2009/101078 and WO 2009/101079.
According to one embodiment of the invention the fungicidal mixtures comprise as active compound II metrafenone.
According to another embodiment of the invention the fungicidal mixtures comprise as active compound I I a compound of group C) selected from: benalaxyl, benalaxyl-M, boscalid , bixafen , fluopyram, fluxapyroxad, isopyrazam, metalaxyl, penflufen, pentihipyrad, sedaxane.
According to one embodiment of the invention the fungicidal mixtures comprise as active compound II boscalid.
Preferred embodiments relate to the compositions listed in table A, where in each case one row of table A corresponds to a fungicidal composition comprising the particular
compound of the formula I mentioned (Component 1 ) and one active compound of the groups mentioned (Component 2), this active compound preferably being selected from the preferred embodiments defined above. Table A
A further embodiment relates to the compositions B-1 to B-165 listed in Table B, where a row of Table B corresponds in each case to a fungicidal composition comprising as component 1 an individualized compound of the formula I and the respective further active substance from groups A) to C) (component 2) stated in the row in question. Preferably, the compositions described comprise the active substances in
synergistically effective amounts. Table B: Composition comprising one individualized compound of the formula I and one further active substance from groups A) to C)
Mixture Component 1 Component 2
B-1 l-A 6-(3,4-dichloro-phenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamin
B-2 l-A 6- (4-tert-butylphenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-
7- ylamine
B-3 l-A 5-methyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamine
B-4 l-A 5-methyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-5 l-A 6-methyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-6 l-A 6-ethyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamin
B-7 l-A 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-8 l-A 5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin- 7-ylamine
B-9 l-A 6-octyl-5-propyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
Mixture Component 1 Component 2
B-10 l-A 5-methoxymethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7- ylamine
B-1 1 l-A 6-octyl-5-trifluormethyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7- ylamine
B-12 l-A 5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamine
B-13 l-A metrafenone
B-14 l-A benalaxyl
B-15 l-A benalaxyl-M
B-16 l-A benodanil
B-17 l-A bixafen
B-18 l-A boscalid
B-19 l-A carboxin
B-20 l-A fenfuram
B-21 l-A fenhexamid
B-22 l-A flutolanil
B-23 l-A fluxapyroxad
B-24 l-A furametpyr
B-25 l-A isopyrazam
B-26 l-A isotianil
B-27 l-A kiraxyl
B-28 l-A mepronil
B-29 l-A metalaxyl
B-30 l-A metalaxyl-M
B-31 l-A of u race
B-32 l-A oxadixyl
B-33 l-A oxycarboxin
B-34 l-A penflufen
B-35 l-A penthiopyrad
B-36 l-A sedaxane
B-37 l-A tecloftalam
B-38 l-A thifluzamide
B-39 l-A tiadinil
B-40 l-A 2-amino-4-methyl-thiazole-5-carboxanilide
B-41 l-A N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 - methyl-1 H-pyrazole-4-carboxamide
B-42 l-A N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- pyrazole-4-carboxamide
B-43 l-A dimethomorph
B-44 l-A flumorph
Mixture Component 1 Component 2
B-45 l-A pyrimorph
B-46 l-A flumetover
B-47 l-A fluopicolide
B-48 l-A fluopyram
B-49 l-A zoxamide
B-50 l-A carpropamid
B-51 l-A dicyclomet
B-52 l-A mandiproamid
B-53 l-A oxytetracyclin
B-54 l-A silthiofam
B-55 l-A N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide
B-56 l-B 6-(3,4-dichloro-phenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamin
B-57 l-B 6- (4-tert-butylphenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-
7- ylamine
B-58 l-B 5-methyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamine
B-59 l-B 5-methyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-60 l-B 6-methyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-61 l-B 6-ethyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamin
B-62 l-B 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-63 l-B 5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin- 7-ylamine
B-64 l-B 6-octyl-5-propyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-65 l-B 5-methoxymethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7- ylamine
B-66 l-B 6-octyl-5-trifluormethyl-[l,2,4]triazolo[l,5-a]pyrimidin-7- ylamine
B-67 l-B 5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamine
B-68 l-B metrafenone
B-69 l-B benalaxyl
B-70 l-B benalaxyl-M
B-71 l-B benodanil
B-72 l-B bixafen
B-73 l-B boscalid
B-74 l-B carboxin
B-75 l-B fenfuram
B-76 l-B fenhexamid
B-77 l-B flutolanil
B-78 l-B fluxapyroxad
Mixture Component 1 Component 2
B-79 l-B furametpyr
B-80 l-B isopyrazam
B-81 l-B isotianil
B-82 l-B kiraxyl
B-83 l-B mepronil
B-84 l-B metalaxyl
B-85 l-B metalaxyl-M
B-86 l-B of u race
B-87 l-B oxadixyl
B-88 l-B oxycarboxin
B-89 l-B penflufen
B-90 l-B penthiopyrad
B-91 l-B sedaxane
B-92 l-B tecloftalam
B-93 l-B thifluzamide
B-94 l-B tiadinil
B-95 l-B 2-amino-4-methyl-thiazole-5-carboxanilide
B-96 l-B N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 - methyl-1 H-pyrazole-4-carboxamide
B-97 l-B N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- pyrazole-4-carboxamide
B-98 l-B dimethomorph
B-99 l-B flumorph
B-100 l-B pyrimorph
B-101 l-B flumetover
B-102 l-B fluopicolide
B-103 l-B fluopyram
B-104 l-B zoxamide
B-105 l-B carpropamid
B-106 l-B dicyclomet
B-107 l-B mandiproamid
B-108 l-B oxytetracyclin
B-109 l-B silthiofam
B-1 10 l-B N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide
B-1 1 1 l-C 6-(3,4-dichloro-phenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamin
B-1 12 l-C 6- (4-tert-butylphenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-
7- ylamine
B-1 13 l-C 5-methyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamine
Mixture Component 1 Component 2
B-1 14 l-C 5-methyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-1 15 l-C 6-methyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-1 16 l-C 6-ethyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamin
B-1 17 l-C 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-1 18 l-C 5-ethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin- 7-ylamine
B-1 19 l-C 6-octyl-5-propyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine
B-120 l-C 5-methoxymethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7- ylamine
B-121 l-C 6-octyl-5-trifluormethyl-[l,2,4]triazolo[l,5-a]pyrimidin-7- ylamine
B-122 l-C 5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin-7-ylamine
B-123 l-C metrafenone
B-124 l-C benalaxyl
B-125 l-C benalaxyl-M
B-126 l-C benodanil
B-127 l-C bixafen
B-128 l-C boscalid
B-129 l-C carboxin
B-130 l-C fenfuram
B-131 l-C fenhexamid
B-132 l-C flutolanil
B-133 l-C fluxapyroxad
B-134 l-C furametpyr
B-135 l-C isopyrazam
B-136 l-C isotianil
B-137 l-C kiraxyl
B-138 l-C mepronil
B-139 l-C metalaxyl
B-140 l-C metalaxyl-M
B-141 l-C of u race
B-142 l-C oxadixyl
B-143 l-C oxycarboxin
B-144 l-C penflufen
B-145 l-C penthiopyrad
B-146 l-C sedaxane
B-147 l-C tecloftalam
B-148 l-C thifluzamide
B-149 l-C tiadinil
B-150 l-C 2-amino-4-methyl-thiazole-5-carboxanilide
Mixture Component 1 Component 2
B-151 l-C N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 - methyl-1 H-pyrazole-4-carboxamide
B-152 l-C N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- pyrazole-4-carboxamide
B-153 l-C dimethomorph
B-154 l-C flumorph
B-155 l-C pyrimorph
B-156 l-C flumetover
B-157 l-C fluopicolide
B-158 l-C fluopyram
B-159 l-C zoxamide
B-160 l-C carpropamid
B-161 l-C dicyclomet
B-162 l-C mandiproamid
B-163 l-C oxytetracyclin
B-164 l-C silthiofam
B-165 l-C N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide
The active compounds mentioned above can also be employed in the form of their agriculturally compatible salts. These are usually the alkali metal or alkaline earth metal salts, such as sodium, potassium or calcium salts.
The compounds of the formula I and active compounds II can be applied
simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
The compounds of the formula I and/or the compounds II of the inventive compositions can be present in different crystal modifications, which may differ in biological activity.
Preference is also given to three component mixtures (ternary mixtures) comprising a further active compound. It is obvious that the active compound II and the further compound should be different.
The following list of active compounds, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible combinations but does not limit them:
A) strobilurins
- azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-[2-
(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester 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, carboxin, fen- furam, fenhexamid, flutolanil, fluxapyroxad, 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, 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;
- other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide; C) azoles
- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothio- conazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;
- imidazoles: cyazofamid, imazalil, pefurazoate, prochloraz, triflumizol;
- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
- others: ethaboxam, etridiazole, hymexazole and 2-(4-chloro-phenyl)-N-[4-(3,4-di- methoxy-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;
- 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, difenzoquat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, proquinazid, 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, methasulphocarb, metiram, propineb, thiram, zineb, ziram;
- carbamates: benthiavalicarb, diethofencarb, iprovalicarb, propamocarb, propamo- carb 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, poly- oxine, validamycin A;
- nitrophenyl derivates: binapacryl, dicloran, dinobuton, dinocap, nitrothal-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, quinto- zene, 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;
- antifungal biocontrol agents, plant bioactivators: Ampelomyces quisqualis (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (e.g.
AFLAGUARD® from Syngenta, CH), Aureobasidium pullulans (e.g. BOTECTOR®
from bio-ferm GmbH, Germany), Bacillus pumilus (e.g. NRRL Accession No. B- 30087 in SONATA® and BALLAD® Plus from AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr. B-21661 in RHAPSODY®, SERENADE® MAX and
SERENADE® ASO from AgraQuest Inc., USA), Bacillus subtilis var. amylolique- faciens FZB24 (e.g. TAEGRO® from Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (e.g. ASPIRE® from Ecogen Inc., USA), Candida saitoana (e.g.
BIOCURE® (in mixture with lysozyme) and BIOCOAT® from Micro Flo Company, USA (BASF SE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ), Clonostachys rosea f. catenulata, also named Gliocladium catenulatum (e.g. isolate J1446: PRESTOP® from Verdera, Finland), Coniothyrium minitans (e.g.
CONTANS® from Prophyta, Germany), Cryphonectrl-Aparasitica (e.g. Endothl- Aparasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g. BIOFOX® from S.I.A.P.A., Italy, FUSACLEAN® from Natural Plant Protection, France),
Metschnikowl-Afructicola (e.g. SHEMER® from Agrogreen, Israel), Microdochium dimerum (e.g. ANTIBOT® from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP® from Verdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVERSUM® from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g. REGALIA® from Marrone Biolnnovations, USA), Talaromyces flavus V1 17b (e.g.
PROTUS® from Prophyta, Germany), Trichoderma asperellum SKT-1 (e.g. ECO- HOPE® from Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T. harzianum J-22 (e.g.
PLANTSHIELD® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX® and
TRICHODERMA 2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. REMEDIER® WP from Isagro Ricerca, Italy), T. polyspo rum and T. harzianum (e.g. BINAB® from BINAB Bio- Innovation AB, Sweden), T. stromaticum (e.g. TRICOVAB® from C.E.P.L.A.C.,
Brazil), T. virens GL-21 (e.g. SOILGARD® from Certis LLC, USA), T. viride {e.g. TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F from T. Stanes & Co. Ltd., Indien), T. viride TV1 (e.g. T. viride TV1 from Agribiotec srl, Italy), Ulocladium oudemansii ΉRU3 (e.g. BOTRY-ZEN® from Botry-Zen Ltd, NZ); others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamin, metrafenone, pyriofenone, 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-meth- yl-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 A/-Methyl-2-{1 -[(5-methyl-3- trifluoromethyl-1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-A/-[(1 R)-1 ,2,3,4-tetrahydro- naphthalen-1 -yl]-4-thiazolecarboxamide.
G) growth regulators
abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dike- gulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthi- acet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-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, sethoxydim, 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, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, 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- d i methoxy-pyri m id i n-2-yl) u rea ;
- triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone,
metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
- ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
- other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
- others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin,
bencarbazone,benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon- ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, 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, pentoxazone, 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, chlorpyrifos, 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, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
- pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfen- valerate, 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: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etox- azole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, 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,
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, lepimectin, 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, bistrifluron, and pyrifluquinazon.
A further embodiment relates to the compositions C-1 to C-1035 listed in Table C, where a row of Table C corresponds in each case to a fungicidal composition comprising as component 1 an individualized compound of the formula I (l-A, l-B, l-C), as component 2: 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-7) and the respective further active substance (component 3) stated in the row in question.
Preferably, the compositions described comprise the active substances in
synergistically effective amounts.
Table C: Composition comprising one individualized compound of the formula I (l-A, l-B or l-C), 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-7) and one further active substance.
Mixtures Components
1 2 3
C-1 l-A III-7 Azoxystrobin
C-2 l-A III-7 Coumethoxystrobin
C-3 l-A III-7 Coumoxystrobin
C-4 l-A III-7 Dimoxystrobin
C-5 l-A III-7 Enestroburin
C-6 l-A III-7 Fluoxastrobin
C-7 l-A III-7 Kresoxim-methyl
C-8 l-A III-7 Metominostrobin
C-9 l-A III-7 Orysastrobin
C-10 l-A III-7 Picoxystrobin
C-1 1 l-A III-7 Pyraclostrobin
C-12 l-A III-7 Pyrametostrobin
C-13 l-A III-7 Pyraoxystrobin
C-14 l-A III-7 Pyribencarb
C-15 l-A III-7 Trifloxystrobin
C-16 l-A 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic
III-7 acid methyl ester
C-17 l-A 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl- allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-
III-7 acetamide
C-18 l-A III-7 Benalaxyl
C-19 l-A III-7 Benalaxyl-M
C-20 l-A III-7 Benodanil
C-21 l-A III-7 Bixafen
C-22 l-A III-7 Boscalid
C-23 l-A III-7 Carboxin
C-24 l-A III-7 Fenfuram
C-25 l-A III-7 Fenhexamid
C-26 l-A III-7 Flutolanil
C-27 l-A III-7 Fluxapyroxad
C-28 l-A III-7 Furametpyr
C-29 l-A III-7 Isopyrazam
C-30 l-A III-7 Isotianil
C-31 l-A III-7 Kiralaxyl
C-32 l-A III-7 Mepronil
C-33 l-A III-7 Metalaxyl
C-34 l-A III-7 Metalaxyl-M
C-35 l-A III-7 Of u race
C-36 l-A III-7 Oxadixyl
C-37 l-A III-7 Oxycarboxin
C-38 l-A III-7 Penflufen
C-39 l-A III-7 Penthiopyrad
C-40 l-A III-7 Sedaxane
C-41 l-A III-7 Tecloftalam
C-42 l-A III-7 Thifluzamide
C-43 l-A III-7 Tiadinil
C-44 l-A III-7 2-Amino-4-methyl-thiazole-5-carboxylic acid anilide
C-45 l-A N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 -
III-7 methyl-1 H-pyrazole-4-carboxamide
C-46 l-A N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-
III-7 pyrazole-4-carboxamide
C-47 l-A III-7 Dimethomorph
C-48 l-A III-7 Flumorph
C-49 l-A III-7 Pyrimorph
C-50 l-A III-7 Flumetover
C-51 l-A III-7 Fluopicolide
C-52 l-A III-7 Fluopyram
C-53 l-A III-7 Zoxamide
C-54 l-A III-7 Carpropamid
C-55 l-A III-7 Diclocymet
C-56 l-A III-7 Mandipropamid
C-57 l-A III-7 Oxytetracyclin
C-58 l-A III-7 Silthiofam
C-59 l-A III-7 N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide
C-60 l-A III-7 Azaconazole
C-61 l-A III-7 Bitertanol
C-62 l-A III-7 Bromuconazole
C-63 l-A III-7 Cyproconazole
C-64 l-A III-7 Difenoconazole
C-65 l-A III-7 Diniconazole
C-66 l-A III-7 Diniconazole-M
C-67 l-A III-7 Epoxiconazole
C-68 l-A III-7 Fenbuconazole
C-69 l-A III-7 Fluquinconazole
C-70 l-A III-7 Flusilazole
C-71 l-A III-7 Flutriafol
C-72 l-A III-7 Hexaconazol
C-73 l-A III-7 Imibenconazole
C-74 l-A III-7 Ipconazole
C-75 l-A III-7 Metconazole
C-76 l-A III-7 Myclobutanil
C-77 l-A III-7 Oxpoconazol
C-78 l-A III-7 Paclobutrazol
C-79 l-A III-7 Penconazole
C-80 l-A III-7 Propiconazole
C-81 l-A III-7 Prothioconazole
C-82 l-A III-7 Simeconazole
C-83 l-A III-7 Tebuconazole
C-84 l-A III-7 Tetraconazole
C-85 l-A III-7 Triadimefon
C-86 l-A III-7 Triadimenol
C-87 l-A III-7 Triticonazole
C-88 l-A III-7 Uniconazole
C-89 l-A III-7 Cyazofamid
C-90 l-A III-7 Imazalil
C-91 l-A III-7 Imazalil-sulfate
C-92 l-A III-7 Pefurazoate
C-93 l-A III-7 Prochloraz
C-94 l-A III-7 Triflumizole
C-95 l-A III-7 Benomyl
C-96 l-A III-7 Carbendazim
C-97 l-A III-7 Fuberidazole
C-98 l-A III-7 Thiabendazole
C-99 l-A III-7 Ethaboxam
C-100 l-A III-7 Etridiazole
C-101 l-A III-7 Hymexazole
C-102 l-A 2-(4-Chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-
III-7 yl]-2-prop-2-ynyloxy-acetamide
C-103 l-A III-7 Fluazinam
C-104 l-A III-7 Pyrifenox
C-105 l-A III-7 3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
C-106 l-A III-7 3-[5-(4-Methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
C-107 l-A III-7 Bupirimate
C-108 l-A III-7 Cyprodinil
C-109 l-A III-7 Diflumetorim
C-1 10 l-A III-7 Fenarimol
C-1 1 1 l-A III-7 Ferimzone
C-1 12 l-A III-7 Mepanipyrim
C-1 13 l-A III-7 Nitra pyrin
C-1 14 l-A III-7 Nuarimol
C-1 15 l-A III-7 Pyrimethanil
C-1 16 l-A III-7 Triforine
C-1 17 l-A III-7 Fenpiclonil
C-1 18 l-A III-7 Fludioxonil
C-1 19 l-A III-7 Aldimorph
C-120 l-A III-7 Dodemorph
C-121 l-A III-7 Dodemorph-acetate
C-122 l-A III-7 Fenpropimorph
C-123 l-A III-7 Tridemorph
C-124 l-A III-7 Fenpropidin
C-125 l-A III-7 Fluoroimid
C-126 l-A III-7 Iprodione
C-127 l-A III-7 Procymidone
C-128 l-A III-7 Vinclozolin
C-129 l-A III-7 Famoxadone
C-130 l-A III-7 Fenamidone
C-131 l-A III-7 Flutianil
C-132 l-A III-7 Octhilinone
C-133 l-A III-7 Probenazole
C-134 l-A 5-Amino-2-iso-propyl-4-ortho-tolyl-2,3-dihydro-pyrazole-1 -
III-7 carbothioic acid S-allyl ester
C-135 l-A III-7 Acibenzolar-S-methyl
C-136 l-A III-7 Amisulbrom
C-137 l-A III-7 Anilazin
C-138 l-A III-7 Blasticidin-S
C-139 l-A III-7 Captafol
C-140 l-A III-7 Captan
C-141 l-A III-7 Chinomethionat
C-142 l-A III-7 Dazomet
C-143 l-A III-7 Debacarb
C-144 l-A III-7 Diclomezine
C-145 l-A III-7 Difenzoquat,
C-146 l-A III-7 Difenzoquat-methylsulfate
C-147 l-A III-7 Fenoxanil
C-148 l-A III-7 Folpet
C-149 l-A III-7 Oxolinsaure
C-150 l-A III-7 Piperalin
C-151 l-A III-7 Proquinazid
C-152 l-A III-7 Pyroquilon
C-153 l-A III-7 Quinoxyfen
C-154 l-A III-7 Triazoxid
C-155 l-A III-7 Tricyclazole
C-156 l-A III-7 2-Butoxy-6-iodo-3-propyl-chromen-4-one
C-157 l-A 5-Chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-
III-7 benzoimidazole
C-158 l-A 5-Chloro-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluoro-phenyl)-
III-7 [1 ,2,4]triazolo[1 ,5-a]pyrimidine
C-159 l-A III-7 Ferbam
C-160 l-A III-7 Mancozeb
C-161 l-A III-7 Maneb
C-162 l-A III-7 Metam
C-163 l-A III-7 Methasulphocarb
C-164 l-A III-7 Metiram
C-165 l-A III-7 Propineb
C-166 l-A III-7 Thiram
C-167 l-A III-7 Zineb
C-168 l-A III-7 Ziram
C-169 l-A III-7 Diethofencarb
C-170 l-A III-7 Benthiavalicarb
C-171 l-A III-7 Iprovalicarb
C-172 l-A III-7 Propamocarb
C-173 l-A III-7 Propamocarb hydrochlorid
C-174 l-A III-7 Valifenalate
C-175 l-A N-(1 -(1 -(4-cyanophenyl)ethanesulfonyl)-but-2-yl) carbamic
III-7 acid-(4-fluorophenyl) ester
C-176 l-A III-7 Dodine
C-177 l-A III-7 Dodine free base
C-178 l-A III-7 Guazatine
C-179 l-A III-7 Guazatine-acetate
C-180 l-A III-7 Iminoctadine
C-181 l-A III-7 Iminoctadine-triacetate
C-182 l-A III-7 Iminoctadine-tris(albesilate)
C-183 l-A III-7 Kasugamycin
C-184 l-A III-7 Kasugamycin-hydrochloride-hydrate
C-185 l-A III-7 Polyoxine
C-186 l-A III-7 Streptomycin
C-187 l-A III-7 Validamycin A
C-188 l-A III-7 Binapacryl
C-189 l-A III-7 Dicloran
C-190 l-A III-7 Dinobuton
C-191 l-A III-7 Dinocap
C-192 l-A III-7 Nitrothal-isopropyl
C-193 l-A III-7 Tecnazen
C-194 l-A III-7 Fentin salts
C-195 l-A III-7 Dithianon
C-196 l-A III-7 Isoprothiolane
C-197 l-A III-7 Edifenphos
C-198 l-A III-7 Fosetyl, Fosetyl-aluminium
C-199 l-A III-7 Iprobenfos
C-200 l-A III-7 Phosphorous acid (H3PO3) and derivatives
C-201 l-A III-7 Pyrazophos
C-202 l-A III-7 Tolclofos-methyl
C-203 l-A III-7 Chlorothalonil
C-204 l-A III-7 Dichlofluanid
C-205 l-A III-7 Dichlorophen
C-206 l-A III-7 Flusulfamide
C-207 l-A III-7 Hexachlorbenzene
C-208 l-A III-7 Pencycuron
C-209 l-A III-7 Pentachlorophenol and salts
C-210 l-A III-7 Phthalide
C-21 1 l-A III-7 Quintozene
C-212 l-A III-7 Thiophanate Methyl
C-213 l-A III-7 Tolylfluanid
C-214 l-A N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-
III-7 benzenesulfonamide
C-215 l-A III-7 Bordeaux mixture
C-216 l-A III-7 Copper acetate
C-217 l-A III-7 Copper hydroxide
C-218 l-A III-7 Copper oxychloride
C-219 l-A III-7 basic Copper sulfate
C-220 l-A III-7 Sulfur
C-221 l-A III-7 Biphenyl
C-222 l-A III-7 Bronopol
C-223 l-A III-7 Cyflufenamid
C-224 l-A III-7 Cymoxanil
C-225 l-A III-7 Diphenylamin
C-226 l-A III-7 Metrafenone
C-227 l-A III-7 Pyriofenone
C-228 l-A III-7 Mildiomycin
C-229 l-A III-7 Oxin-copper
C-230 l-A III-7 Prohexadione calcium
C-231 l-A III-7 Spiroxamine
C-232 l-A III-7 Tebufloquin
C-233 l-A III-7 Tolylfluanid
C-234 l-A N-(Cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-
III-7 phenyl)-methyl)-2-phenyl acetamide
C-235 l-A N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-
III-7 phenyl)-N-ethyl-N-methyl formamidine
C-236 l-A N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-
III-7 phenyl)-N-ethyl-N-methyl formamidine
C-237 l-A N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-
III-7 phenyl)-N-ethyl-N-methyl formamidine
C-238 l-A N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-
III-7 phenyl)-N-ethyl-N-methyl formamidine
C-239 l-A 2-{1 -[2-(5-Methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]- piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1 , 2,3,4-
III-7 tetrahydro-naphthalen-1 -yl)-amide
C-240 l-A 2-{1 -[2-(5-Methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]- piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 ,2,3,4-
III-7 tetrahydro-naphthalen-1 -yl-amide
C-241 l-A Methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-
III-7 4-yl ester
C-242 l-A A/-Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)- acetyl]-piperidin-4-yl}-A/-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -
III-7 yl]-4-thiazolecarboxamide
C-243 l-A III-7 Bacillus subtilis NRRL No. B-21661
C-244 l-A III-7 Bacillus pumilus NRRL No. B-30087
C-245 l-A III-7 Ulocladium oudemansii
C-246 l-A III-7 Carbaryl
C-247 l-A III-7 Carbofuran
C-248 l-A III-7 Carbosulfan
C-249 l-A III-7 Methomylthiodicarb
C-250 l-A III-7 Bifenthrin
C-251 l-A III-7 Cyfluthrin
C-252 l-A III-7 Cypermethrin
C-253 l-A III-7 alpha-Cypermethrin
C-254 l-A III-7 zeta-Cypermethrin
C-255 l-A III-7 Deltamethrin
C-256 l-A III-7 Esfenvalerate
C-257 l-A III-7 Lambda-cyhalothrin
C-258 l-A III-7 Permethrin
C-259 l-A III-7 Tefluthrin
C-260 l-A III-7 Diflubenzuron
C-261 l-A III-7 Flufenoxuron
C-262 l-A III-7 Lufenuron
C-263 l-A III-7 Teflubenzuron
C-264 l-A III-7 Spirotetramate
C-265 l-A III-7 Clothianidin
C-266 l-A III-7 Dinotefuran
C-267 l-A III-7 Imidacloprid
C-268 l-A III-7 Thiamethoxam
C-269 l-A III-7 Acetamiprid
C-270 l-A III-7 Thiacloprid
C-271 l-A III-7 Endosulfan
C-272 l-A III-7 Fipronil
C-273 l-A III-7 Abamectin
C-274 l-A III-7 Emamectin
C-275 l-A III-7 Spinosad
C-276 l-A III-7 Spinetoram
C-277 l-A III-7 Hydramethylnon
C-278 l-A III-7 Chlorfenapyr
C-279 l-A III-7 Fenbutatin oxide
C-280 l-A III-7 Indoxacarb
C-281 l-A III-7 Metaflumizone
C-282 l-A III-7 Flonicamid
C-283 l-A III-7 Lubendiamide
C-284 l-A III-7 Chlorantraniliprole
C-285 l-A III-7 Cyazypyr (HGW86)
C-286 l-A III-7 Cyflumetofen
C-287 l-A III-7 Acetochlor
C-288 l-A III-7 Dimethenamid
C-289 l-A III-7 metolachlor
C-290 l-A III-7 Metazachlor
C-291 l-A III-7 Glyphosate
C-292 l-A III-7 Glufosinate
C-293 l-A III-7 Sulfosate
C-294 l-A III-7 Clodinafop
C-295 l-A III-7 Fenoxaprop
C-296 l-A III-7 Fluazifop
C-297 l-A III-7 Haloxyfop
C-298 l-A III-7 Paraquat
C-299 l-A III-7 Phenmedipham
C-300 l-A III-7 Clethodim
C-301 l-A III-7 Cycloxydim
C-302 l-A III-7 Profoxydim
C-303 l-A III-7 Sethoxydim
C-304 l-A III-7 Tepraloxydim
C-305 l-A III-7 Pendimethalin
C-306 l-A III-7 Prodiamine
C-307 l-A III-7 Trifluralin
C-308 l-A III-7 Acifluorfen
C-309 l-A III-7 Bromoxynil
C-310 l-A III-7 Imazamethabenz
C-31 1 l-A III-7 Imazamox
C-312 l-A III-7 Imazapic
C-313 l-A III-7 Imazapyr
C-314 l-A III-7 Imazaquin
C-315 l-A III-7 Imazethapyr
C-316 l-A III-7 2,4-Dichlorophenoxyacetic acid (2,4-D)
C-317 l-A III-7 Chloridazon
C-318 l-A III-7 Clopyralid
C-319 l-A III-7 Fluroxypyr
C-320 l-A III-7 Picloram
C-321 l-A III-7 Picolinafen
C-322 l-A III-7 Bensulfuron
C-323 l-A III-7 Chlorimuron-ethyl
C-324 l-A III-7 Cyclosulfamuron
C-325 l-A III-7 lodosulfuron
C-326 l-A III-7 Mesosulfuron
C-327 l-A III-7 Metsulfuron-methyl
C-328 l-A III-7 Nicosulfuron
C-329 l-A III-7 Rimsulfuron
C-330 l-A III-7 Triflusulfuron
C-331 l-A III-7 Atrazine
C-332 l-A III-7 Hexazinone
C-333 l-A III-7 Diuron
C-334 l-A III-7 Florasulam
C-335 l-A III-7 Pyroxasulfone
C-336 l-A III-7 Bentazone
C-337 l-A III-7 Cinidon-ethlyl
C-338 l-A III-7 Cinmethylin
C-339 l-A III-7 Dicamba
C-340 l-A III-7 Diflufenzopyr
C-341 l-A III-7 Quinclorac
C-342 l-A III-7 Quinmerac
C-343 l-A III-7 Mesotrione
C-344 l-A III-7 Saflufenacil
C-345 l-A III-7 Topramezone
C-346 l-B III-7 Azoxystrobin
C-347 l-B III-7 Coumethoxystrobin
C-348 l-B III-7 Coumoxystrobin
C-349 l-B III-7 Dimoxystrobin
C-350 l-B III-7 Enestroburin
C-351 l-B III-7 Fluoxastrobin
C-352 l-B III-7 Kresoxim-methyl
C-353 l-B III-7 Metominostrobin
C-354 l-B III-7 Orysastrobin
C-355 l-B III-7 Picoxystrobin
C-356 l-B III-7 Pyraclostrobin
C-357 l-B III-7 Pyrametostrobin
C-358 l-B III-7 Pyraoxystrobin
C-359 l-B III-7 Pyribencarb
C-360 l-B III-7 Trifloxystrobin
C-361 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic l-B III-7 acid methyl ester
C-362 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl- allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl- l-B III-7 acetamide
C-363 l-B III-7 Benalaxyl
C-364 l-B III-7 Benalaxyl-M
C-365 l-B III-7 Benodanil
C-366 l-B III-7 Bixafen
C-367 l-B III-7 Boscalid
C-368 l-B III-7 Carboxin
C-369 l-B III-7 Fenfuram
C-370 l-B III-7 Fenhexamid
C-371 l-B III-7 Flutolanil
C-372 l-B III-7 Fluxapyroxad
C-373 l-B III-7 Furametpyr
C-374 l-B III-7 Isopyrazam
C-375 l-B III-7 Isotianil
C-376 l-B III-7 Kiralaxyl
C-377 l-B III-7 Mepronil
C-378 l-B III-7 Metalaxyl
C-379 l-B III-7 Metalaxyl-M
C-380 l-B III-7 Of u race
C-381 l-B III-7 Oxadixyl
C-382 l-B III-7 Oxycarboxin
C-383 l-B III-7 Penflufen
C-384 l-B III-7 Penthiopyrad
C-385 l-B III-7 Sedaxane
C-386 l-B III-7 Tecloftalam
C-387 l-B III-7 Thifluzamide
C-388 l-B III-7 Tiadinil
C-389 l-B III-7 2-Amino-4-methyl-thiazole-5-carboxylic acid anilide
C-390 N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 - l-B III-7 methyl-1 H-pyrazole-4-carboxamide
C-391 N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- l-B III-7 pyrazole-4-carboxamide
C-392 l-B III-7 Dimethomorph
C-393 l-B III-7 Flumorph
C-394 l-B III-7 Pyrimorph
C-395 l-B III-7 Flumetover
C-396 l-B III-7 Fluopicolide
C-397 l-B III-7 Fluopyram
C-398 l-B III-7 Zoxamide
C-399 l-B III-7 Carpropamid
C-400 l-B III-7 Diclocymet
C-401 l-B III-7 Mandipropamid
C-402 l-B III-7 Oxytetracyclin
C-403 l-B III-7 Silthiofam
C-404 l-B III-7 N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide
C-405 l-B III-7 Azaconazole
C-406 l-B III-7 Bitertanol
C-407 l-B III-7 Bromuconazole
C-408 l-B III-7 Cyproconazole
C-409 l-B III-7 Difenoconazole
C-410 l-B III-7 Diniconazole
C-41 1 l-B III-7 Diniconazole-M
C-412 l-B III-7 Epoxiconazole
C-413 l-B III-7 Fenbuconazole
C-414 l-B III-7 Fluquinconazole
C-415 l-B III-7 Flusilazole
C-416 l-B III-7 Flutriafol
C-417 l-B III-7 Hexaconazol
C-418 l-B III-7 Imibenconazole
C-419 l-B III-7 Ipconazole
C-420 l-B III-7 Metconazole
C-421 l-B III-7 Myclobutanil
C-422 l-B III-7 Oxpoconazol
C-423 l-B III-7 Paclobutrazol
C-424 l-B III-7 Penconazole
C-425 l-B III-7 Propiconazole
C-426 l-B III-7 Prothioconazole
C-427 l-B III-7 Simeconazole
C-428 l-B III-7 Tebuconazole
C-429 l-B III-7 Tetraconazole
C-430 l-B III-7 Triadimefon
C-431 l-B III-7 Triadimenol
C-432 l-B III-7 Triticonazole
C-433 l-B III-7 Uniconazole
C-434 l-B III-7 Cyazofamid
C-435 l-B III-7 Imazalil
C-436 l-B III-7 Imazalil-sulfate
C-437 l-B III-7 Pefurazoate
C-438 l-B III-7 Prochloraz
C-439 l-B III-7 Triflumizole
C-440 l-B III-7 Benomyl
C-441 l-B III-7 Carbendazim
C-442 l-B III-7 Fuberidazole
C-443 l-B III-7 Thiabendazole
C-444 l-B III-7 Ethaboxam
C-445 l-B III-7 Etridiazole
C-446 l-B III-7 Hymexazole
C-447 2-(4-Chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5- l-B III-7 yl]-2-prop-2-ynyloxy-acetamide
C-448 l-B III-7 Fluazinam
C-449 l-B III-7 Pyrifenox
C-450 l-B III-7 3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
C-451 l-B III-7 3-[5-(4-Methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
C-452 l-B III-7 Bupirimate
C-453 l-B III-7 Cyprodinil
C-454 l-B III-7 Diflumetorim
C-455 l-B III-7 Fenarimol
C-456 l-B III-7 Ferimzone
C-457 l-B III-7 Mepanipyrim
C-458 l-B III-7 Nitra pyrin
C-459 l-B III-7 Nuarimol
C-460 l-B III-7 Pyrimethanil
C-461 l-B III-7 Triforine
C-462 l-B III-7 Fenpiclonil
C-463 l-B III-7 Fludioxonil
C-464 l-B III-7 Aldimorph
C-465 l-B III-7 Dodemorph
C-466 l-B III-7 Dodemorph-acetate
C-467 l-B III-7 Fenpropimorph
C-468 l-B III-7 Tridemorph
C-469 l-B III-7 Fenpropidin
C-470 l-B III-7 Fluoroimid
C-471 l-B III-7 Iprodione
C-472 l-B III-7 Procymidone
C-473 l-B III-7 Vinclozolin
C-474 l-B III-7 Famoxadone
C-475 l-B III-7 Fenamidone
C-476 l-B III-7 Flutianil
C-477 l-B III-7 Octhilinone
C-478 l-B III-7 Probenazole
C-479 5-Amino-2-iso-propyl-4-ortho-tolyl-2,3-dihydro-pyrazole-1 - l-B III-7 carbothioic acid S-allyl ester
C-480 l-B III-7 Acibenzolar-S-methyl
C-481 l-B III-7 Amisulbrom
C-482 l-B III-7 Anilazin
C-483 l-B III-7 Blasticidin-S
C-484 l-B III-7 Captafol
C-485 l-B III-7 Captan
C-486 l-B III-7 Chinomethionat
C-487 l-B III-7 Dazomet
C-488 l-B III-7 Debacarb
C-489 l-B III-7 Diclomezine
C-490 l-B III-7 Difenzoquat,
C-491 l-B III-7 Difenzoquat-methylsulfate
C-492 l-B III-7 Fenoxanil
C-493 l-B III-7 Folpet
C-494 l-B III-7 Oxolinsaure
C-495 l-B III-7 Piperalin
C-496 l-B III-7 Proquinazid
C-497 l-B III-7 Pyroquilon
C-498 l-B III-7 Quinoxyfen
C-499 l-B III-7 Triazoxid
C-500 l-B III-7 Tricyclazole
C-501 l-B III-7 2-Butoxy-6-iodo-3-propyl-chromen-4-one
C-502 5-Chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H- l-B III-7 benzoimidazole
C-503 5-Chloro-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluoro-phenyl)- l-B III-7 [1 ,2,4]triazolo[1 ,5-a]pyrimidine
C-504 l-B III-7 Ferbam
C-505 l-B III-7 Mancozeb
C-506 l-B III-7 Maneb
C-507 l-B III-7 Metam
C-508 l-B III-7 Methasulphocarb
C-509 l-B III-7 Metiram
C-510 l-B III-7 Propineb
C-51 1 l-B III-7 Thiram
C-512 l-B III-7 Zineb
C-513 l-B III-7 Ziram
C-514 l-B III-7 Diethofencarb
C-515 l-B III-7 Benthiavalicarb
C-516 l-B III-7 Iprovalicarb
C-517 l-B III-7 Propamocarb
C-518 l-B III-7 Propamocarb hydrochlorid
C-519 l-B III-7 Valifenalate
C-520 N-(1 -(1 -(4-cyanophenyl)ethanesulfonyl)-but-2-yl) carbamic l-B III-7 acid-(4-fluorophenyl) ester
C-521 l-B III-7 Dodine
C-522 l-B III-7 Dodine free base
C-523 l-B III-7 Guazatine
C-524 l-B III-7 Guazatine-acetate
C-525 l-B III-7 Iminoctadine
C-526 l-B III-7 Iminoctadine-triacetate
C-527 l-B III-7 Iminoctadine-tris(albesilate)
C-528 l-B III-7 Kasugamycin
C-529 l-B III-7 Kasugamycin-hydrochloride-hydrate
C-530 l-B III-7 Polyoxine
C-531 l-B III-7 Streptomycin
C-532 l-B III-7 Validamycin A
C-533 l-B III-7 Binapacryl
C-534 l-B III-7 Dicloran
C-535 l-B III-7 Dinobuton
C-536 l-B III-7 Dinocap
C-537 l-B III-7 Nitrothal-isopropyl
C-538 l-B III-7 Tecnazen
C-539 l-B III-7 Fentin salts
C-540 l-B III-7 Dithianon
C-541 l-B III-7 Isoprothiolane
C-542 l-B III-7 Edifenphos
C-543 l-B III-7 Fosetyl, Fosetyl-aluminium
C-544 l-B III-7 Iprobenfos
C-545 l-B III-7 Phosphorous acid (H3PO3) and derivatives
C-546 l-B III-7 Pyrazophos
C-547 l-B III-7 Tolclofos-methyl
C-548 l-B III-7 Chlorothalonil
C-549 l-B III-7 Dichlofluanid
C-550 l-B III-7 Dichlorophen
C-551 l-B III-7 Flusulfamide
C-552 l-B III-7 Hexachlorbenzene
C-553 l-B III-7 Pencycuron
C-554 l-B III-7 Pentachlorophenol and salts
C-555 l-B III-7 Phthalide
C-556 l-B III-7 Quintozene
C-557 l-B III-7 Thiophanate Methyl
C-558 l-B III-7 Tolylfluanid
C-559 N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- l-B III-7 benzenesulfonamide
C-560 l-B III-7 Bordeaux mixture
C-561 l-B III-7 Copper acetate
C-562 l-B III-7 Copper hydroxide
C-563 l-B III-7 Copper oxychloride
C-564 l-B III-7 basic Copper sulfate
C-565 l-B III-7 Sulfur
C-566 l-B III-7 Biphenyl
C-567 l-B III-7 Bronopol
C-568 l-B III-7 Cyflufenamid
C-569 l-B III-7 Cymoxanil
C-570 l-B III-7 Diphenylamin
C-571 l-B III-7 Metrafenone
C-572 l-B III-7 Pyriofenone
C-573 l-B III-7 Mildiomycin
C-574 l-B III-7 Oxin-copper
C-575 l-B III-7 Prohexadione calcium
C-576 l-B III-7 Spiroxamine
C-577 l-B III-7 Tebufloquin
C-578 l-B III-7 Tolylfluanid
C-579 N-(Cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro- l-B III-7 phenyl)-methyl)-2-phenyl acetamide
C-580 N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- l-B III-7 phenyl)-N-ethyl-N-methyl formamidine
C-581 N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- l-B III-7 phenyl)-N-ethyl-N-methyl formamidine
C-582 N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)- l-B III-7 phenyl)-N-ethyl-N-methyl formamidine
C-583 N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)- l-B III-7 phenyl)-N-ethyl-N-methyl formamidine
C-584 2-{1 -[2-(5-Methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]- piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1 ,2,3,4- l-B III-7 tetrahydro-naphthalen-1 -yl)-amide
C-585 2-{1 -[2-(5-Methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]- piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 , 2,3,4- l-B III-7 tetrahydro-naphthalen-1 -yl-amide
C-586 Methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin- l-B III-7 4-yl ester
C-587 A/-Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)- acetyl]-piperidin-4-yl}-A/-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 - l-B III-7 yl]-4-thiazolecarboxamide
C-588 l-B III-7 Bacillus subtilis NRRL No. B-21661
C-589 l-B III-7 Bacillus pumilus NRRL No. B-30087
C-590 l-B III-7 Ulocladium oudemansii
C-591 l-B III-7 Carbaryl
C-592 l-B III-7 Carbofuran
C-593 l-B III-7 Carbosulfan
C-594 l-B III-7 Methomylthiodicarb
C-595 l-B III-7 Bifenthrin
C-596 l-B III-7 Cyfluthrin
C-597 l-B III-7 Cypermethrin
C-598 l-B III-7 alpha-Cypermethrin
C-599 l-B III-7 zeta-Cypermethrin
C-600 l-B III-7 Deltamethrin
C-601 l-B III-7 Esfenvalerate
C-602 l-B III-7 Lambda-cyhalothrin
C-603 l-B III-7 Permethrin
C-604 l-B III-7 Tefluthrin
C-605 l-B III-7 Diflubenzuron
C-606 l-B III-7 Flufenoxuron
C-607 l-B III-7 Lufenuron
C-608 l-B III-7 Teflubenzuron
C-609 l-B III-7 Spirotetramate
C-610 l-B III-7 Clothianidin
C-61 1 l-B III-7 Dinotefuran
C-612 l-B III-7 Imidacloprid
C-613 l-B III-7 Thiamethoxam
C-614 l-B III-7 Acetamiprid
C-615 l-B III-7 Thiacloprid
C-616 l-B III-7 Endosulfan
C-617 l-B III-7 Fipronil
C-618 l-B III-7 Abamectin
C-619 l-B III-7 Emamectin
C-620 l-B III-7 Spinosad
C-621 l-B III-7 Spinetoram
C-622 l-B III-7 Hydramethylnon
C-623 l-B III-7 Chlorfenapyr
C-624 l-B III-7 Fenbutatin oxide
C-625 l-B III-7 Indoxacarb
C-626 l-B III-7 Metaflumizone
C-627 l-B III-7 Flonicamid
C-628 l-B III-7 Lubendiamide
C-629 l-B III-7 Chlorantraniliprole
C-630 l-B III-7 Cyazypyr (HGW86)
C-631 l-B III-7 Cyflumetofen
C-632 l-B III-7 Acetochlor
C-633 l-B III-7 Dimethenamid
C-634 l-B III-7 metolachlor
C-635 l-B III-7 Metazachlor
C-636 l-B III-7 Glyphosate
C-637 l-B III-7 Glufosinate
C-638 l-B III-7 Sulfosate
C-639 l-B III-7 Clodinafop
C-640 l-B III-7 Fenoxaprop
C-641 l-B III-7 Fluazifop
C-642 l-B III-7 Haloxyfop
C-643 l-B III-7 Paraquat
C-644 l-B III-7 Phenmedipham
C-645 l-B III-7 Clethodim
C-646 l-B III-7 Cycloxydim
C-647 l-B III-7 Profoxydim
C-648 l-B III-7 Sethoxydim
C-649 l-B III-7 Tepraloxydim
C-650 l-B III-7 Pendimethalin
C-651 l-B III-7 Prodiamine
C-652 l-B III-7 Trifluralin
C-653 l-B III-7 Acifluorfen
C-654 l-B III-7 Bromoxynil
C-655 l-B III-7 Imazamethabenz
C-656 l-B III-7 Imazamox
C-657 l-B III-7 Imazapic
C-658 l-B III-7 Imazapyr
C-659 l-B III-7 Imazaquin
C-660 l-B III-7 Imazethapyr
C-661 l-B III-7 2,4-Dichlorophenoxyacetic acid (2,4-D)
C-662 l-B III-7 Chloridazon
C-663 l-B III-7 Clopyralid
C-664 l-B III-7 Fluroxypyr
C-665 l-B III-7 Picloram
C-666 l-B III-7 Picolinafen
C-667 l-B III-7 Bensulfuron
C-668 l-B III-7 Chlorimuron-ethyl
C-669 l-B III-7 Cyclosulfamuron
C-670 l-B III-7 lodosulfuron
C-671 l-B III-7 Mesosulfuron
C-672 l-B III-7 Metsulfuron-methyl
C-673 l-B III-7 Nicosulfuron
C-674 l-B III-7 Rimsulfuron
C-675 l-B III-7 Triflusulfuron
C-676 l-B III-7 Atrazine
C-677 l-B III-7 Hexazinone
C-678 l-B III-7 Diuron
C-679 l-B III-7 Florasulam
C-680 l-B III-7 Pyroxasulfone
C-681 l-B III-7 Bentazone
C-682 l-B III-7 Cinidon-ethlyl
C-683 l-B III-7 Cinmethylin
C-684 l-B III-7 Dicamba
C-685 l-B III-7 Diflufenzopyr
C-686 l-B III-7 Quinclorac
C-687 l-B III-7 Quinmerac
C-688 l-B III-7 Mesotrione
C-689 l-B III-7 Saflufenacil
C-690 l-B III-7 Topramezone
C-691 I-C III-7 Azoxystrobin
C-692 I-C III-7 Coumethoxystrobin
C-693 I-C III-7 Coumoxystrobin
C-694 I-C III-7 Dimoxystrobin
C-695 I-C III-7 Enestroburin
C-696 I-C III-7 Fluoxastrobin
C-697 I-C III-7 Kresoxim-methyl
C-698 I-C III-7 Metominostrobin
C-699 I-C III-7 Orysastrobin
C-700 I-C III-7 Picoxystrobin
C-701 I-C III-7 Pyraclostrobin
C-702 I-C III-7 Pyrametostrobin
C-703 I-C III-7 Pyraoxystrobin
C-704 I-C III-7 Pyribencarb
C-705 I-C III-7 Trifloxystrobin
C-706 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic
I-C III-7 acid methyl ester
C-707 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl- allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-
I-C III-7 acetamide
C-708 I-C III-7 Benalaxyl
C-709 I-C III-7 Benalaxyl-M
C-710 I-C III-7 Benodanil
C-71 1 l-C III-7 Bixafen
C-712 l-C III-7 Boscalid
C-713 l-C III-7 Carboxin
C-714 l-C III-7 Fenfuram
C-715 l-C III-7 Fenhexamid
C-716 l-C III-7 Flutolanil
C-717 l-C III-7 Fluxapyroxad
C-718 l-C III-7 Furametpyr
C-719 l-C III-7 Isopyrazam
C-720 l-C III-7 Isotianil
C-721 l-C III-7 Kiralaxyl
C-722 l-C III-7 Mepronil
C-723 l-C III-7 Metalaxyl
C-724 l-C III-7 Metalaxyl-M
C-725 l-C III-7 Of u race
C-726 l-C III-7 Oxadixyl
C-727 l-C III-7 Oxycarboxin
C-728 l-C III-7 Penflufen
C-729 l-C III-7 Penthiopyrad
C-730 l-C III-7 Sedaxane
C-731 l-C III-7 Tecloftalam
C-732 l-C III-7 Thifluzamide
C-733 l-C III-7 Tiadinil
C-734 l-C III-7 2-Amino-4-methyl-thiazole-5-carboxylic acid anilide
C-735 N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 - l-C III-7 methyl-1 H-pyrazole-4-carboxamide
C-736 N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- l-C III-7 pyrazole-4-carboxamide
C-737 l-C III-7 Dimethomorph
C-738 l-C III-7 Flumorph
C-739 l-C III-7 Pyrimorph
C-740 l-C III-7 Flumetover
C-741 l-C III-7 Fluopicolide
C-742 l-C III-7 Fluopyram
C-743 l-C III-7 Zoxamide
C-744 l-C III-7 Carpropamid
C-745 l-C III-7 Diclocymet
C-746 l-C III-7 Mandipropamid
C-747 l-C III-7 Oxytetracyclin
C-748 l-C III-7 Silthiofam
C-749 l-C III-7 N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide
C-750 l-C III-7 Azaconazole
C-751 l-C III-7 Bitertanol
C-752 l-C III-7 Bromuconazole
C-753 l-C III-7 Cyproconazole
C-754 l-C III-7 Difenoconazole
C-755 l-C III-7 Diniconazole
C-756 l-C III-7 Diniconazole-M
C-757 l-C III-7 Epoxiconazole
C-758 l-C III-7 Fenbuconazole
C-759 l-C III-7 Fluquinconazole
C-760 l-C III-7 Flusilazole
C-761 l-C III-7 Flutriafol
C-762 l-C III-7 Hexaconazol
C-763 l-C III-7 Imibenconazole
C-764 l-C III-7 Ipconazole
C-765 l-C III-7 Metconazole
C-766 l-C III-7 Myclobutanil
C-767 l-C III-7 Oxpoconazol
C-768 l-C III-7 Paclobutrazol
C-769 l-C III-7 Penconazole
C-770 l-C III-7 Propiconazole
C-771 l-C III-7 Prothioconazole
C-772 l-C III-7 Simeconazole
C-773 l-C III-7 Tebuconazole
C-774 l-C III-7 Tetraconazole
C-775 l-C III-7 Triadimefon
C-776 l-C III-7 Triadimenol
C-777 l-C III-7 Triticonazole
C-778 l-C III-7 Uniconazole
C-779 l-C III-7 Cyazofamid
C-780 l-C III-7 Imazalil
C-781 l-C III-7 Imazalil-sulfate
C-782 l-C III-7 Pefurazoate
C-783 l-C III-7 Prochloraz
C-784 l-C III-7 Triflumizole
C-785 l-C III-7 Benomyl
C-786 l-C III-7 Carbendazim
C-787 l-C III-7 Fuberidazole
C-788 l-C III-7 Thiabendazole
C-789 l-C III-7 Ethaboxam
C-790 l-C III-7 Etridiazole
C-791 l-C III-7 Hymexazole
C-792 2-(4-Chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5- l-C III-7 yl]-2-prop-2-ynyloxy-acetamide
C-793 l-C III-7 Fluazinam
C-794 l-C III-7 Pyrifenox
C-795 l-C III-7 3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
C-796 l-C III-7 3-[5-(4-Methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
C-797 l-C III-7 Bupirimate
C-798 l-C III-7 Cyprodinil
C-799 l-C III-7 Diflumetorim
C-800 l-C III-7 Fenarimol
C-801 l-C III-7 Ferimzone
C-802 l-C III-7 Mepanipyrim
C-803 l-C III-7 Nitra pyrin
C-804 l-C III-7 Nuarimol
C-805 l-C III-7 Pyrimethanil
C-806 l-C III-7 Triforine
C-807 l-C III-7 Fenpiclonil
C-808 l-C III-7 Fludioxonil
C-809 l-C III-7 Aldimorph
C-810 l-C III-7 Dodemorph
C-81 1 l-C III-7 Dodemorph-acetate
C-812 l-C III-7 Fenpropimorph
C-813 l-C III-7 Tridemorph
C-814 l-C III-7 Fenpropidin
C-815 l-C III-7 Fluoroimid
C-816 l-C III-7 Iprodione
C-817 l-C III-7 Procymidone
C-818 l-C III-7 Vinclozolin
C-819 l-C III-7 Famoxadone
C-820 l-C III-7 Fenamidone
C-821 l-C III-7 Flutianil
C-822 l-C III-7 Octhilinone
C-823 l-C III-7 Probenazole
C-824 5-Amino-2-iso-propyl-4-ortho-tolyl-2,3-dihydro-pyrazole-1 - l-C III-7 carbothioic acid S-allyl ester
C-825 l-C III-7 Acibenzolar-S-methyl
C-826 l-C III-7 Amisulbrom
C-827 l-C III-7 Anilazin
C-828 l-C III-7 Blasticidin-S
C-829 l-C III-7 Captafol
C-830 l-C III-7 Captan
C-831 l-C III-7 Chinomethionat
C-832 l-C III-7 Dazomet
C-833 l-C III-7 Debacarb
C-834 l-C III-7 Diclomezine
C-835 l-C III-7 Difenzoquat,
C-836 l-C III-7 Difenzoquat-methylsulfate
C-837 l-C III-7 Fenoxanil
C-838 l-C III-7 Folpet
C-839 l-C III-7 Oxolinsaure
C-840 l-C III-7 Piperalin
C-841 l-C III-7 Proquinazid
C-842 l-C III-7 Pyroquilon
C-843 l-C III-7 Quinoxyfen
C-844 l-C III-7 Triazoxid
C-845 l-C III-7 Tricyclazole
C-846 l-C III-7 2-Butoxy-6-iodo-3-propyl-chromen-4-one
C-847 5-Chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H- l-C III-7 benzoimidazole
C-848 5-Chloro-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluoro-phenyl)- l-C III-7 [1 ,2,4]triazolo[1 ,5-a]pyrimidine
C-849 l-C III-7 Ferbam
C-850 l-C III-7 Mancozeb
C-851 l-C III-7 Maneb
C-852 l-C III-7 Metam
C-853 l-C III-7 Methasulphocarb
C-854 l-C III-7 Metiram
C-855 l-C III-7 Propineb
C-856 l-C III-7 Thiram
C-857 l-C III-7 Zineb
C-858 l-C III-7 Ziram
C-859 l-C III-7 Diethofencarb
C-860 l-C III-7 Benthiavalicarb
C-861 l-C III-7 Iprovalicarb
C-862 l-C III-7 Propamocarb
C-863 l-C III-7 Propamocarb hydrochlorid
C-864 l-C III-7 Valifenalate
C-865 N-(1 -(1 -(4-cyanophenyl)ethanesulfonyl)-but-2-yl) carbamic l-C III-7 acid-(4-fluorophenyl) ester
C-866 l-C III-7 Dodine
C-867 l-C III-7 Dodine free base
C-868 l-C III-7 Guazatine
C-869 l-C III-7 Guazatine-acetate
C-870 l-C III-7 Iminoctadine
C-871 l-C III-7 Iminoctadine-triacetate
C-872 l-C III-7 Iminoctadine-tris(albesilate)
C-873 l-C III-7 Kasugamycin
C-874 l-C III-7 Kasugamycin-hydrochloride-hydrate
C-875 l-C III-7 Polyoxine
C-876 l-C III-7 Streptomycin
C-877 l-C III-7 Validamycin A
C-878 l-C III-7 Binapacryl
C-879 l-C III-7 Dicloran
C-880 l-C III-7 Dinobuton
C-881 l-C III-7 Dinocap
C-882 l-C III-7 Nitrothal-isopropyl
C-883 l-C III-7 Tecnazen
C-884 l-C III-7 Fentin salts
C-885 l-C III-7 Dithianon
C-886 l-C III-7 Isoprothiolane
C-887 l-C III-7 Edifenphos
C-888 l-C III-7 Fosetyl, Fosetyl-aluminium
C-889 l-C III-7 Iprobenfos
C-890 l-C III-7 Phosphorous acid (H3PO3) and derivatives
C-891 l-C III-7 Pyrazophos
C-892 l-C III-7 Tolclofos-methyl
C-893 l-C III-7 Chlorothalonil
C-894 l-C III-7 Dichlofluanid
C-895 l-C III-7 Dichlorophen
C-896 l-C III-7 Flusulfamide
C-897 l-C III-7 Hexachlorbenzene
C-898 l-C III-7 Pencycuron
C-899 l-C III-7 Pentachlorophenol and salts
C-900 l-C III-7 Phthalide
C-901 l-C III-7 Quintozene
C-902 l-C III-7 Thiophanate Methyl
C-903 l-C III-7 Tolylfluanid
C-904 N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- l-C III-7 benzenesulfonamide
C-905 l-C III-7 Bordeaux mixture
C-906 l-C III-7 Copper acetate
C-907 l-C III-7 Copper hydroxide
C-908 l-C III-7 Copper oxychloride
C-909 l-C III-7 basic Copper sulfate
C-910 l-C III-7 Sulfur
C-91 1 l-C III-7 Biphenyl
C-912 l-C III-7 Bronopol
C-913 l-C III-7 Cyflufenamid
C-914 l-C III-7 Cymoxanil
C-915 l-C III-7 Diphenylamin
C-916 l-C III-7 Metrafenone
C-917 l-C III-7 Pyriofenone
C-918 l-C III-7 Mildiomycin
C-919 l-C III-7 Oxin-copper
C-920 l-C III-7 Prohexadione calcium
C-921 l-C III-7 Spiroxamine
C-922 l-C III-7 Tebufloquin
C-923 l-C III-7 Tolylfluanid
C-924 N-(Cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro- l-C III-7 phenyl)-methyl)-2-phenyl acetamide
C-925 N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- l-C III-7 phenyl)-N-ethyl-N-methyl formamidine
C-926 N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- l-C III-7 phenyl)-N-ethyl-N-methyl formamidine
C-927 N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)- l-C III-7 phenyl)-N-ethyl-N-methyl formamidine
C-928 N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)- l-C III-7 phenyl)-N-ethyl-N-methyl formamidine
C-929 2-{1 -[2-(5-Methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]- piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1 , 2,3,4- l-C III-7 tetrahydro-naphthalen-1 -yl)-amide
C-930 2-{1 -[2-(5-Methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]- piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(R)-1 , 2,3,4- l-C III-7 tetrahydro-naphthalen-1 -yl-amide
C-931 Methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin- l-C III-7 4-yl ester
C-932 A/-Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)- acetyl]-piperidin-4-yl}-A/-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 - l-C III-7 yl]-4-thiazolecarboxamide
C-933 l-C III-7 Bacillus subtilis NRRL No. B-21661
C-934 l-C III-7 Bacillus pumilus NRRL No. B-30087
C-935 l-C III-7 Ulocladium oudemansii
C-936 l-C III-7 Carbaryl
C-937 l-C III-7 Carbofuran
C-938 l-C III-7 Carbosulfan
C-939 l-C III-7 Methomylthiodicarb
C-940 l-C III-7 Bifenthrin
C-941 l-C III-7 Cyfluthrin
C-942 l-C III-7 Cypermethrin
C-943 l-C III-7 alpha-Cypermethrin
C-944 l-C III-7 zeta-Cypermethrin
C-945 l-C III-7 Deltamethrin
C-946 l-C III-7 Esfenvalerate
C-947 l-C III-7 Lambda-cyhalothrin
C-948 l-C III-7 Permethrin
C-949 l-C III-7 Tefluthrin
C-950 l-C III-7 Diflubenzuron
C-951 l-C III-7 Flufenoxuron
C-952 l-C III-7 Lufenuron
C-953 l-C III-7 Teflubenzuron
C-954 l-C III-7 Spirotetramate
C-955 l-C III-7 Clothianidin
C-956 l-C III-7 Dinotefuran
C-957 l-C III-7 Imidacloprid
C-958 l-C III-7 Thiamethoxam
C-959 l-C III-7 Acetamiprid
C-960 l-C III-7 Thiacloprid
C-961 l-C III-7 Endosulfan
C-962 l-C III-7 Fipronil
C-963 l-C III-7 Abamectin
C-964 l-C III-7 Emamectin
C-965 l-C III-7 Spinosad
C-966 l-C III-7 Spinetoram
C-967 l-C III-7 Hydramethylnon
C-968 l-C III-7 Chlorfenapyr
C-969 l-C III-7 Fenbutatin oxide
C-970 l-C III-7 Indoxacarb
C-971 l-C III-7 Metaflumizone
C-972 l-C III-7 Flonicamid
C-973 l-C III-7 Lubendiamide
C-974 l-C III-7 Chlorantraniliprole
C-975 l-C III-7 Cyazypyr (HGW86)
C-976 l-C III-7 Cyflumetofen
C-977 l-C III-7 Acetochlor
C-978 l-C III-7 Dimethenamid
C-979 l-C III-7 metolachlor
C-980 l-C III-7 Metazachlor
C-981 l-C III-7 Glyphosate
C-982 l-C III-7 Glufosinate
C-983 l-C III-7 Sulfosate
C-984 l-C III-7 Clodinafop
C-985 l-C III-7 Fenoxaprop
C-986 l-C III-7 Fluazifop
C-987 l-C III-7 Haloxyfop
C-988 l-C III-7 Paraquat
C-989 l-C III-7 Phenmedipham
C-990 l-C III-7 Clethodim
C-991 l-C III-7 Cycloxydim
C-992 l-C III-7 Profoxydim
C-993 l-C III-7 Sethoxydim
C-994 l-C III-7 Tepraloxydim
C-995 l-C III-7 Pendimethalin
C-996 l-C III-7 Prodiamine
C-997 l-C III-7 Trifluralin
C-998 l-C III-7 Acifluorfen
C-999 l-C III-7 Bromoxynil
C-1000 l-C III-7 Imazamethabenz
C-1001 l-C III-7 Imazamox
C-1002 l-C III-7 Imazapic
C-1003 l-C III-7 Imazapyr
C-1004 l-C III-7 Imazaquin
C-1005 l-C III-7 Imazethapyr
C-1006 l-C III-7 2,4-Dichlorophenoxyacetic acid (2,4-D)
C-1007 l-C III-7 Chloridazon
C-1008 l-C III-7 Clopyralid
C-1009 l-C III-7 Fluroxypyr
C-1010 l-C III-7 Picloram
C-101 1 l-C III-7 Picolinafen
C-1012 l-C III-7 Bensulfuron
C-1013 l-C III-7 Chlorimuron-ethyl
C-1014 l-C III-7 Cyclosulfamuron
C-1015 l-C III-7 lodosulfuron
C-1016 l-C III-7 Mesosulfuron
C-1017 l-C III-7 Metsulfuron-methyl
C-1018 l-C III-7 Nicosulfuron
C-1019 l-C III-7 Rimsulfuron
C-1020 l-C III-7 Triflusulfuron
C-1021 l-C III-7 Atrazine
C-1022 l-C III-7 Hexazinone
C-1023 l-C III-7 Diuron
C-1024 l-C III-7 Florasulam
C-1025 l-C III-7 Pyroxasulfone
C-1026 l-C III-7 Bentazone
C-1027 l-C III-7 Cinidon-ethlyl
C-1028 l-C III-7 Cinmethylin
C-1029 l-C III-7 Dicamba
C-1030 l-C III-7 Diflufenzopyr
C-1031 l-C III-7 Quinclorac
C-1032 l-C III-7 Quinmerac
C-1033 l-C III-7 Mesotrione
C-1034 l-C III-7 Saflufenacil
C-1035 l-C III-7 Topramezone
In binary mixtures, i.e. mixtures according to the invention comprising one compound of the formula I (component 1 ) and one further active compound II (component 2), e. g. one active substance from groups A) to C) as defined in claim 1 , the weight ratio of component 1 and component 2 generally depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :3 to 3:1.
In ternary mixtures, i.e. compositions according to the invention comprising one compound of the formula I (component 1 ) and a first further active compound II
(component 2) and a second further active compound (component 3), e. g. an active substance from groups A) to C) as defined above, the weight ratio of component 1 and component 2 depends from the properties of the active substances used, preferably it is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1 , and the weight ratio of component 1 and component 3 preferably is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1.
The invention also relates to agrochemical compositions comprising a solvent or solid carrier and the inventive fungicidal mixtures.
The agrochemical composition comprises a fungicidally effective amount of a com- pound of the formula I and at least one compound II. The term "effective amount" denotes an amount of the composition or of the compounds of the formula I and at least one compound II, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial
damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific mixture used.
The inventive mixtures 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), emulsifiable concentrates (EC), emulsions (EW, EO, ES), 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, EC, 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 application form and active substance, respectively.
Examples for suitable auxiliaries are solvents, solid carriers, dispersants or emulsifiers (such as further solubilizers, protective colloids, surfactants and adhesion agents), organic and anorganic thickeners, bactericides, anti-freezing agents, anti-foaming agents, if appropriate colorants and tackifiers or binders (e. g. for seed treatment formulations).
Suitable solvents are water, organic solvents such as mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones such as cyclohexanone and gamma-butyrolactone, fatty acid dimethylamides, 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, limestone, lime, chalk, bole, loess, clays, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
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 fungicidal mixture and, if appropriate, further active substances, 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.
Examples for composition types are:
1 . Composition types for dilution with water
i) Water-soluble concentrates (SL, LS)
10 parts by weight of a compound of the formula I according to the invention are dissolved in 90 parts by weight of water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active substance dissolves upon dilution with water. In this way, a composition having a content of 10% by weight of active substance is obtained.
ii) Dispersible concentrates (DC)
20 parts by weight of a according to the invention are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, e. g.
polyvinylpyrrolidone. Dilution with water gives a dispersion. The active substance content is 20% by weight.
iii) Emulsifiable concentrates (EC)
15 parts by weight of a compound of the formula I according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
Dilution with water gives an emulsion. The composition has an active substance content of 15% by weight.
iv) Emulsions (EW, EO, ES)
25 parts by weight of a compound of the formula I according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The composition has an active substance content of 25% by weight. v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20 parts by weight of a compound of the formula I according to the invention are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. The active substance content in the composition is 20% by weight. vi) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of a compound of the formula I according to the invention are ground finely with addition of 50 parts by weight of dispersants and wetting agents and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. The composition has an active substance content of 50% by weight.
vii) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)
75 parts by weight of a compound of the formula I according to the invention are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active substance. The active substance content of the composition is 75% by weight. viii) Gel (GF)
In an agitated ball mill, 20 parts by weight of a compound of the formula I according to the invention are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance, whereby a composition with 20% (w/w) of active substance is obtained.
2. Composition types to be applied undiluted
ix) Dustable powders (DP, DS)
5 parts by weight of a compound of the formula I according to the invention are ground
finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable composition having an active substance content of 5% by weight.
x) Granules (GR, FG, GG, MG)
0.5 parts by weight of a compound of the formula I according to the invention is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted having an active substance content of 0.5% by weight.
xi) ULV solutions (UL)
10 parts by weight of a compound of the formula I according to the invention are dissolved in 90 parts by weight of an organic solvent, e. g. xylene. This gives a composition to be applied undiluted having an active substance content of 10% by weight.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Water-soluble concentrates (LS), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES) emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. These compositions can be applied to plant propagation materials, particularly seeds, diluted or undiluted. The compositions in question give, after two-to- tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during 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, soaking and in-furrow application methods of the propagation material. In a preferred embodiment, the compounds or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
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,
011 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 process (ULV), it being possible to apply compositions comprising over 95% by weight of active substance, or even to apply the active substance without additives.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg 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 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably 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 active substances or the compositions comprising them, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1 .
Adjuvants which can be used are in particular organic modified polysiloxanes such as Break Thru S 240®; alcohol alkoxylates such as Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO/PO block polymers, e. g. Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates such as Lutensol XP 80®; and dioctyl sulfosuccinate sodium such as Leophen RA®.
According to this invention, applying the compounds of the formula I together with at
least compound II is to be understood to denote, that at least one compound of the formula 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, materials or the soil as well as plants, plant propagation materials, particularly seeds, soil, surfaces, materials or rooms to be protected from fungal attack) in a fungicidally effective amount. This can be obtained by applying the compounds of the formula I and at least one 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. The same proceeding do apply to the ternary mixtures.
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.
In one embodiment of the invention, the kits may include one or more, including all, components that may be used to prepare a subject agrochemical composition. E. g., kits may include one or more fungicide component(s) and/or an adjuvant component and/or a insecticide component and/or a growth regulator component and/or a herbicde. One or more of the components may already be combined together or pre- formulated. In those embodiments where more than two components are provided in a kit, the components may already be combined together and as such are packaged in a single container such as a vial, bottle, can, pouch, bag or canister. In other
embodiments, two or more components of a kit may be packaged separately, i. e., not pre-formulated. As such, kits may include one or more separate containers such as vials, cans, bottles, pouches, bags or canisters, each container containing a separate component for an agrochemical composition. In both forms, a component of the kit may be applied separately from or together with the further components or as a component of a combination composition according to the invention for preparing the composition according to the invention.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank or a spray plane. Here, the agrochemical composition is made up with water and/or buffer to the desired application
concentration, it being possible, if appropriate, to add further auxiliaries, and the ready- to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 50 to 500 liters of the ready-to-use spray liquor are applied per hectare of agricultural useful area, preferably 100 to 400 liters.
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 mixtures and the compositions according to the invention, respectively, are suitable as fungicides. Therefore, the present invention relates to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the inventive mixture the composition.
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 fungicidal mixtures and the 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; sweet leaf (also called Stevia); 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, fungicidal mixtures and compositions thereof, respectively 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 includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
Preferably, treatment of plant propagation materials with the fungicidal mixtures 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.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxyl- phenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibit- tors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res.
58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA,
CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins;
proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy- steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publi- cations mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars
producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard® I (cotton cultivars producing the Cry1 Ac toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
The fungicidal mixtures and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Altemaria 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; Aphano- myces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), 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; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad- leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C.
miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthi- anum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (£. pyri), soft fruits (£. veneta: anthracnose) and vines (£. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (£. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph:
Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxy- sporum on tomatoes, F. solani on soybeans and F verticillioides on corn; Gaeumanno- myces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grain- staining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helmintho- sporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; 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.
parasitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) 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, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. feres (net blotch) on
barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals;
Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits;
Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp.
(black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T.
basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
The fungicidal mixtures and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, colling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the
particular attention is paid to the following harmful fungi: Ascomycetes such as
Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Por/'a spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichorma spp., Altemaria spp.,
Paecilomyces spp. and Zygomycetes such as /Wucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
The fungicidal mixtures and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of the fungicidal mixtures and compositions thereof, respectively.
The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.
The components can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
The components are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
Plant propagation materials may be treated with the fungicidal mixture as such or the composition prophylactically either at or before planting or transplanting.
The fungicidal action of the mixtures according to the invention can be shown by the tests described below.
The active compound ametoctradin (111-7) was pre-formulated and applied at the respective concentrations/ dose rates.
The propyl gallate (l-A) was dissolved at the respective concentration for greenhouse trials in water, for field trials under the addition of ethanol at a concentration of 1 %.
The visually determined percentages of infected leaf areas were 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, 20-22, 1967) and compared with the observed efficacies.
Colby's formula:
E = x + y - x-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
1. Greenhouse trial data
• Example 1 : Activity against grape downy mildew, Plasmopara viticola The treatment solutions are mixed according to the respective ratio given in the table below and sprayed onto young grape plants (grape cuttings, growth stage 15). On average 3 to 5 replications (i.e. plants) are sprayed per treatment. The plants are placed in a greenhouse chamber at approx. 20°C for 2 days in case of a 2d preventive test. A spore suspension of Plasmopara viticola (1 ,5 to 2 x 10-5 conidia/ ml) is sprayed onto the plants. After inoculation, the plants are placed for 24 h in a dark dew chamber at approx. 21 °C and approx. 95% relative humidity. The plants are placed afterwards in a greenhouse chamber at 21 °C and 55% relative humidity (1 Oh day, 14h night).24h before the disease assessment is made, the lower leaf surfaces of all leaves are sprayed with water and the plants are moved back into the dew chamber. Using visual assessment in %, the disease severity is assessed 6 days after the inoculation. The disease assessment given in the table below represents the mean value of all replicates.
Active compound / Concentration Observed Calculated active mixture (ppm) efficacy efficacy
according to
Colby (%)
ametoctradin 2,5 68
0,75 18
propyl gallate 500 12
ametoctradin + 2,5 + 500 95 72
propyl gallate
ametoctradin + 0,75 + 500 68 27
propyl gallate
2. Field trial data Grape plants of the variety Mueller-Thurgau were grown under practical conditions in the field for use in field trials. The used grape plants were between 6 and 15 years old. Single guyot and cordon were the pruning methods applied. The distance between plants in the row was between 0,5 and 1 m. Distance between rows was 2 m.
Depending on the field trial, 5 or 8 plants were used per plot, respectively. Each treatment was tested in 3 replicates.
• Example 2: Activity against grape downy mildew, Plasmopara viticola
Active compound / Concentration Observed Calculated active mixture (g ai /ha) efficacy efficacy
1 1.07.2009 according to
GS 77 Colby (%)
ametoctradin 300 49
propyl gallate 1000 3
ametoctradin + 300 85 51 propyl gallate 1000
Location: Limburgerhof / Waldeck
Variety: Muller Thurgau
Application: 6 at 10-14 days interval
Application table
• Example 3: Activity against grape downy mildew, Plasmopara viticola
Location: Limburgerhof / Trifelsring
Variety: Muller Thurgau
Application: 6 at 10-14 days interval Application table
Appl. Appl. Growth
Appl. Date Carrier / Vol Code Meth. stage
A 06.05.2009 Spray H20 800,00 L/HA 53
B 15.05.2009 Spray H20 800,00 L/HA 55
C 27.05.2009 Spray H20 800,00 L/HA 59
D 08.06.2009 Spray H20 800,00 L/HA 65
E 18.06.2009 Spray H20 800,00 L/HA 71
F 02.07.2009 Spray H20 800,00 L/HA 75
Claims
1 . A fungicidal mixture comprising, as active components:
1 ) gallic acid esters of the formula I
in which the substituent is as defined below:
Y is Ci-Ci2-alkyl;
and
at least one active compound II selected from the following groups
azolopyrimidinylamines of the formula III, 
in which the substituents are as defined below:
R1 is C3-Ci2-alkyl, C2-Ci2-alkenyl, C5-Ci2-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-Ci-C4-alkyl;
R2 is Ci-Ci2-alkyl, C2-Ci2-alkenyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl; where the aliphatic chains in R1 and/or R2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C3-C8-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C6-alkyl or NRARB;
RA, RB are hydrogen and Ci-C6-alkyl;
where the cyclic groups in R1 and/or Ra may be substituted by one to four groups Rb:
Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, Ci-Cio-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-C6-alkoxy;
R3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, Ci-C6-alkyl,
Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C8-cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl,
Ci-Cio-alkylcarbonyl, Ci-Cio-alkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C2-Cio-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzyl- thio, Ci-C6-alkyl-S(0)m-;
m is 0, 1 or 2;
A is CR3 or N
B) metrafenone;
C) carboxamides selected from:
carboxanilides:benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, fluxapyroxad, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxy- carboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2- amino-4-methyl-thiazole-5-carboxanilide, 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;
other carboxamides: carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide; in a synergistically effective amount.
2. The fungicidal mixture according to claim 1 , comprising a compound of the formula I and a compound II in a weight ratio of from 100:1 to 1 :100.
3. The fungicidal mixture according to claim 1 or 2, comprising a compound of the formula I, in which
A is propyl, octyl or dodecyl.
4. The fungicidal mixture according to any of claims 1 to 3, comprising a compound of the formula I, in which
A is propyl.
5. The fungicidal mixture according to any of claims 1 to 4, wherein compound II is a compound of the formula III corresponding to the formula IIIA 
in which
is C3-Ci2-alkyl, C5-Ci2-alkoxyalkyl, phenyl or phenyl-Ci-C4-alkyl, where phenyl may be substituted by one to three groups Rb;
R2 is Ci-Ci2-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl; R3 is hydrogen or NH2.
6. The fungicidal mixture according to any of claims 1 to 5, wherein compound II is a compound selected from the group consisting of:
6-(3,4-dichloro-phenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine, 6-(4-tert-butylphenyl)-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
5-methyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
5- methyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
6- methyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
6-ethyl-5-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
5- ethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
6- octyl-5-propyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
5- methoxymethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine,
6- octyl-5-trifluormethyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine and
5-trifluoromethyl-6-(3,5,5-trimethyl-hexyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7- ylamine.
7. The fungicidal mixture according to any of claims 1 to 4, wherein compound II is metrafenone.
8. The fungicidal mixture according to any of claims 1 to 4, wherein compound II is a com pound of group C) selected from : benalaxyl, benalaxyl-M, boscalid, bixafen, fluopyram, fluxapyroxad, isopyrazam, metalaxyl, penflufen, pentihipyrad, sedaxane.
9. The fungicidal mixture according to any of claims 1 to 4, wherein compound II is boscalid.
10. A fungicidal mixture according to any of claims 1 to 9, comprising a further active compound.
1 1 . An agrochemical composition, comprising a liquid or solid carrier and a mixture according to any of claims 1 to 10.
12. Seed, comprising a mixture according to any of claims 1 to 10 or a composition according to claim 1 1 in an amount of from 1 to 1000 g/100 kg of seed.
13. A method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of a mixture as defined in one of claims 1 to 10 or the composition as defined in claim 1 1 .
14. A method for improving plant health, comprising treating a plant, its propagation material, the lotus where the plant is growing or is to grow with an effective amount of the mixture as defined in any one of claims 1 to 10 or the composition as defined in claim 1 1 .
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33185010P | 2010-05-06 | 2010-05-06 | |
| US61/331850 | 2010-05-06 | ||
| EP10162180.3 | 2010-05-06 | ||
| EP10162180 | 2010-05-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2011138345A2 true WO2011138345A2 (en) | 2011-11-10 |
| WO2011138345A3 WO2011138345A3 (en) | 2012-05-31 |
Family
ID=44802565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2011/057081 Ceased WO2011138345A2 (en) | 2010-05-06 | 2011-05-04 | Fungicidal mixtures based on gallic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2011138345A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2745693A1 (en) | 2012-12-20 | 2014-06-25 | Forschungsanstalt Agroscope Reckenholz-Tänikon ART | Method and composition for controlling fungal phytopathogens |
| CN108271461A (en) * | 2018-01-19 | 2018-07-13 | 新疆天业（集团）有限公司 | A kind of processing method of lotus rhizome seed |
Citations (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| 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 |
| GB2095558A (en) | 1981-03-30 | 1982-10-06 | Avon Packers Ltd | Formulation of agricultural chemicals |
| EP0071792A2 (en) | 1981-08-01 | 1983-02-16 | BASF Aktiengesellschaft | 7-Amino-azolo-(1,5-a)-pyrimidines process for their production and fungicides containing them |
| EP0141317A2 (en) | 1983-10-21 | 1985-05-15 | BASF Aktiengesellschaft | 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them |
| EP0374753A2 (en) | 1988-12-19 | 1990-06-27 | American Cyanamid Company | Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines |
| EP0392225A2 (en) | 1989-03-24 | 1990-10-17 | Ciba-Geigy Ag | Disease-resistant transgenic plants |
| EP0427529A1 (en) | 1989-11-07 | 1991-05-15 | Pioneer Hi-Bred International, Inc. | Larvicidal lectins and plant insect resistance based thereon |
| 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 |
| EP0451878A1 (en) | 1985-01-18 | 1991-10-16 | Plant Genetic Systems, N.V. | Modifying plants by genetic engineering to combat or control insects |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| WO1993007278A1 (en) | 1991-10-04 | 1993-04-15 | Ciba-Geigy Ag | Synthetic dna sequence having enhanced insecticidal activity in maize |
| US5208030A (en) | 1989-08-30 | 1993-05-04 | Imperial Chemical Industries Plc | Active ingredient dosage device |
| US5232701A (en) | 1990-10-11 | 1993-08-03 | Sumitomo Chemical Company, Limited | Boron carbonate and solid acid pesticidal composition |
| WO1995034656A1 (en) | 1994-06-10 | 1995-12-21 | Ciba-Geigy Ag | Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests |
| EP0707445A1 (en) | 1993-07-03 | 1996-04-24 | Basf Ag | READY-TO-USE, STABLE, MULTI-PHASE AQUEOUS FORMULATION FOR PHYTOSANITARY PRODUCTS AND METHOD OF PREPARATION |
| WO2002015701A2 (en) | 2000-08-25 | 2002-02-28 | Syngenta Participations Ag | Bacillus thuringiensis crystal protein hybrids |
| WO2003009687A1 (en) | 2001-07-26 | 2003-02-06 | Basf Aktiengesellschaft | 7-amino triazolopyrimidines for controlling harmful fungi |
| WO2003018810A2 (en) | 2001-08-31 | 2003-03-06 | Syngenta Participations Ag | Modified cry3a toxins and nucleic acid sequences coding therefor |
| WO2003052073A2 (en) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Novel corn event |
| WO2005004404A1 (en) | 2003-07-03 | 2005-01-13 | Thomson Licensing | Method for controlling a network station in a network of a first type from a network station in a network of a second type, and connection unit for the connection of the networks of the first and second types |
| 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 |
| WO2005087771A2 (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 |
| 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 |
| WO2006092428A2 (en) | 2005-03-02 | 2006-09-08 | Basf Aktiengesellschaft | 2-substituted 7-amino-azolopyrimidine, a method for the production and use thereof for controlling pathogenic fungi and agents containing said compound |
| WO2008065527A2 (en) | 2006-11-27 | 2008-06-05 | Carlo Ghisalberti | Gallic acid esters of fragrant alcohols |
| WO2008071714A1 (en) | 2006-12-15 | 2008-06-19 | Rohm And Haas Company | Mixtures comprising 1-methylcyclopropene |
| WO2009071448A1 (en) | 2007-12-05 | 2009-06-11 | Basf Se | Pyridylmethyl-sulfonamide compounds |
| WO2009101079A1 (en) | 2008-02-15 | 2009-08-20 | Basf Se | Pyrimidylmethyl sulfonamide compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1909579E (en) * | 2005-07-27 | 2016-02-10 | Basf Se | FUNGICIDE MIXTURES BASED ON AZOLOPYRYIDINYLAMINES |
| EP2069413B1 (en) * | 2006-10-05 | 2011-08-03 | Basf Se | Active ingredient formulations containing comb polymers |
| TWI361044B (en) * | 2006-12-04 | 2012-04-01 | Univ Nat Taiwan | Antifungal compositions for inhibiting growth of wood decay fungi and use thereof |
-
2011
- 2011-05-04 WO PCT/EP2011/057081 patent/WO2011138345A2/en not_active Ceased
Patent Citations (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| 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 |
| GB2095558A (en) | 1981-03-30 | 1982-10-06 | Avon Packers Ltd | Formulation of agricultural chemicals |
| EP0071792A2 (en) | 1981-08-01 | 1983-02-16 | BASF Aktiengesellschaft | 7-Amino-azolo-(1,5-a)-pyrimidines process for their production and fungicides containing them |
| EP0141317A2 (en) | 1983-10-21 | 1985-05-15 | BASF Aktiengesellschaft | 7-Amino-azolo[1,5-a]pyrimidines and fungicides containing them |
| EP0451878A1 (en) | 1985-01-18 | 1991-10-16 | Plant Genetic Systems, N.V. | Modifying plants by genetic engineering to combat or control insects |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| EP0374753A2 (en) | 1988-12-19 | 1990-06-27 | American Cyanamid Company | Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines |
| EP0392225A2 (en) | 1989-03-24 | 1990-10-17 | Ciba-Geigy Ag | Disease-resistant transgenic plants |
| US5208030A (en) | 1989-08-30 | 1993-05-04 | Imperial Chemical Industries Plc | Active ingredient dosage device |
| EP0427529A1 (en) | 1989-11-07 | 1991-05-15 | Pioneer Hi-Bred International, Inc. | Larvicidal lectins and plant insect resistance based thereon |
| 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 |
| US5232701A (en) | 1990-10-11 | 1993-08-03 | Sumitomo Chemical Company, Limited | Boron carbonate and solid acid pesticidal composition |
| WO1993007278A1 (en) | 1991-10-04 | 1993-04-15 | Ciba-Geigy Ag | Synthetic dna sequence having enhanced insecticidal activity in maize |
| EP0707445A1 (en) | 1993-07-03 | 1996-04-24 | Basf Ag | READY-TO-USE, STABLE, MULTI-PHASE AQUEOUS FORMULATION FOR PHYTOSANITARY PRODUCTS AND METHOD OF PREPARATION |
| WO1995034656A1 (en) | 1994-06-10 | 1995-12-21 | Ciba-Geigy Ag | Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests |
| WO2002015701A2 (en) | 2000-08-25 | 2002-02-28 | Syngenta Participations Ag | Bacillus thuringiensis crystal protein hybrids |
| WO2003009687A1 (en) | 2001-07-26 | 2003-02-06 | Basf Aktiengesellschaft | 7-amino triazolopyrimidines for controlling harmful fungi |
| WO2003018810A2 (en) | 2001-08-31 | 2003-03-06 | Syngenta Participations Ag | Modified cry3a toxins and nucleic acid sequences coding therefor |
| WO2003052073A2 (en) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Novel corn event |
| WO2005004404A1 (en) | 2003-07-03 | 2005-01-13 | Thomson Licensing | Method for controlling a network station in a network of a first type from a network station in a network of a second type, and connection unit for the connection of the networks of the first and second types |
| 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 |
| WO2005087771A2 (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 |
| 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 |
| WO2006092428A2 (en) | 2005-03-02 | 2006-09-08 | Basf Aktiengesellschaft | 2-substituted 7-amino-azolopyrimidine, a method for the production and use thereof for controlling pathogenic fungi and agents containing said compound |
| WO2008065527A2 (en) | 2006-11-27 | 2008-06-05 | Carlo Ghisalberti | Gallic acid esters of fragrant alcohols |
| WO2008071714A1 (en) | 2006-12-15 | 2008-06-19 | Rohm And Haas Company | Mixtures comprising 1-methylcyclopropene |
| WO2009071448A1 (en) | 2007-12-05 | 2009-06-11 | Basf Se | Pyridylmethyl-sulfonamide compounds |
| WO2009071449A1 (en) | 2007-12-05 | 2009-06-11 | Basf Se | Pyridylmethyl-sulfonamide compounds |
| WO2009101079A1 (en) | 2008-02-15 | 2009-08-20 | Basf Se | Pyrimidylmethyl sulfonamide compounds |
| WO2009101078A1 (en) | 2008-02-15 | 2009-08-20 | Basf Se | Pyrimidylmethyl sulfonamide compounds |
Non-Patent Citations (12)
| Title |
|---|
| "Antifungal activity of octyl gallate is known from Bioorg", MED. CHEM. LETT., vol. 11, no. 3, December 2001 (2001-12-01), pages 7 - 50 |
| AUSTRAL. J. AGRICULT. RES., vol. 58, 2007, pages 708 |
| BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 December 1967 (1967-12-04), pages 147 - 48 |
| COLBY, S.R.: "Calculating synergistic and antagonistic responses of herbicide combinations", WEEDS, vol. 15, 1967, pages 20 - 22 |
| HANCE ET AL.: "Weed Control Handbook", 1989, BLACKWELL SCIENTIFIC |
| KLINGMAN: "Weed Control as a Science", 1961, J. WILEY & SONS |
| MOLLET, H., GRUBEMANN, A.: "Formulation technology", 2001, WILEY VCH VERLAG |
| PERRY'S: "Chemical Engineer's Handbook", 1963, MCGRAW-HILL, pages: 8 - 57 |
| PEST MANAGEM. SCI., vol. 61, 2005, pages 246 |
| PUCCI B, HELV. CHIM. ACTA, vol. 86, no. 2, 2003, pages 247 - 265 |
| SCIENCE, vol. 316, 2007, pages 1185 |
| WEED SCI., vol. 57, 2009, pages 108 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2745693A1 (en) | 2012-12-20 | 2014-06-25 | Forschungsanstalt Agroscope Reckenholz-Tänikon ART | Method and composition for controlling fungal phytopathogens |
| CN108271461A (en) * | 2018-01-19 | 2018-07-13 | 新疆天业（集团）有限公司 | A kind of processing method of lotus rhizome seed |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011138345A3 (en) | 2012-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20120322654A1 (en) | Synergistic fungicidal mixtures | |
| US20130130898A1 (en) | Fungicidal Compositions | |
| JP2012530100A (en) | Disinfectant mixture | |
| JP2014520828A (en) | Bactericidal alkyl-substituted 2- [2-chloro-4- (4-chloro-phenoxy) -phenyl] -1- [1,2,4] triazol-1-yl-ethanol compounds | |
| EP2560492B1 (en) | Fungicidal mixtures comprising ametoctradin and a tetrazoloxime derivative | |
| EP2720541A1 (en) | Compositions comprising fungicidal substituted dithiines and further actives | |
| US20130023412A1 (en) | Fungicidal Mixtures Based on Azolopyrimidinylamines | |
| EP2481284A2 (en) | Pesticidal mixtures | |
| EP2402343A1 (en) | Pyrazole-fused bicyclic compounds | |
| WO2011138345A2 (en) | Fungicidal mixtures based on gallic acid esters | |
| US9253980B2 (en) | Use of substituted dithiine-tetracarboximides for combating phytopathogenic fungi | |
| WO2013124250A2 (en) | Fungicidal substituted thiophenes | |
| EP2402339A1 (en) | Pyrazolopyridine compounds | |
| WO2010115758A2 (en) | Fungicidal compounds | |
| DE102011017541A1 (en) | Composition useful for controlling phytopathogenic harmful fungi, and protecting a plant propagation material, comprises2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazole-5-carboxanilide and silthiofam | |
| DE102011017670A1 (en) | Composition, useful e.g. for combating phytopathogenic harmful fungi, e.g. soil-borne pathogens, from classes of Plasmodiophoromycetes, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and fluxapyroxad | |
| EP2402335A1 (en) | Pyrazolopyridine compounds | |
| DE102011017715A1 (en) | Composition useful for controlling phytopathogenic harmful fungi, and protecting plant propagation materials, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and pyrimethanil as active ingredients | |
| DE102011017669A1 (en) | Composition, useful e.g. for combating phytopathogenic harmful fungi, e.g. soil-borne pathogens, from classes of Plasmodiophoromycetes, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and fludioxonil | |
| DE102011017716A1 (en) | Composition, useful e.g. for combating phytopathogenic harmful fungi, e.g. soil-borne pathogens, from classes of Plasmodiophoromycetes, comprises 2',4'-dimethoxy-4-cyclopropyl-1,2,3-thiadiazol-5-carboxanilide and triticonazole |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 11718709 Country of ref document: EP Kind code of ref document: A2 |