WO1999029671A1 - Derives d'acide 3-pyrazol-1-yl-benzoique - Google Patents

Derives d'acide 3-pyrazol-1-yl-benzoique Download PDF

Info

Publication number
WO1999029671A1
WO1999029671A1 PCT/EP1998/007920 EP9807920W WO9929671A1 WO 1999029671 A1 WO1999029671 A1 WO 1999029671A1 EP 9807920 W EP9807920 W EP 9807920W WO 9929671 A1 WO9929671 A1 WO 9929671A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
phenyl
methyl
haloalkyl
Prior art date
Application number
PCT/EP1998/007920
Other languages
German (de)
English (en)
Inventor
Karl Eicken
Joachim Rheinheimer
Frank Wetterich
Eberhard Ammermann
Gisela Lorenz
John-Bryan Speakman
Siegfried Strathmann
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO1999029671A1 publication Critical patent/WO1999029671A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to benzoic acid derivatives of the general formula I.
  • R 1 -C-alkyl C.-C alkoxy or halogen
  • R 2 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, halogen or aryl, which may optionally have one to three substituents selected from nitro, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C alkoxy, C 1 -C haloalkoxy, C 1 -C alkylthio and C 1 -C alkoxycarbonyl can be carried,
  • C 1 -C 4 haloalkoxy, C 1 -C 8 alkylthio and C 1 -C 4 alkoxy carbonyl can carry,
  • R 5 is hydrogen, Ci-C ⁇ -alkyl, Ci-C ⁇ -haloalkyl, C 3 -C 6 -alkenyl, C 3 -Cg-alkynyl, Ci-Cg-hydroxyalkyl, Ci-C ⁇ -alkoxy-Ci -ce-alkyl, C ⁇ -C 6 -alkylthio-C ⁇ -C 6 alkyl, C 6 -C cycloalkyl, C -C 6 cycloalkyl-C ⁇ -C3-alkyl, phenyl or phenyl-C ⁇ -C -alkyl wherein the phenyl ring of the last two substituents one to three groups selected from nitro, halogen, cyano, C 4 -alkyl, C haloalkyl, C ⁇ -C -alkoxy, C 4 haloalkoxy, C ⁇ -C 4 -Alkylthio and -CC
  • Z is oxygen or sulfur, or
  • R 6 and R 7 independently of one another are each hydrogen, Ci-C ⁇ - alkyl, C ⁇ -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C -C 6 - alkynyl, Ci-C ⁇ hydroxyalkyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl - alkyl, C 3 -C 6 cycloalkyl, phenyl or phenyl-C ⁇ -C -alkyl, wherein the phenyl ring of the latter two Substituents selected from one to three groups
  • R 8 and R 9 independently of one another are each hydrogen, C 1 -C 5 -alkyl, C -C 6 -alkenyl, C -C 6 -alkynyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy-C ⁇ -C 6 -alkyl, C 6 alkylthio -Al--C ⁇ -C6 alkyl, cyano-Ci-Cg-alkyl, C-C6 cycloalkyl, phenyl or phenyl-C ⁇ -C - alkyl, wherein the phenyl ring of the last two substituents one to three groups selected from nitro, halogen, cyano, C 4 -alkyl, C 4 haloalkyl, C ⁇ -C4 alkoxy, C_-C 4 -Halo- genalkoxy, -C ⁇ alkylthio and -C
  • R 8 has the meaning defined above and R 10 for hydrogen, -CC 6 alkyl, C 3 -Cg alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl -CC 3 -alkyl, phenyl or phenyl -CC-C -alkyl, the phenyl ring of the latter two substituents being one to three groups selected from nitro, halogen, cyano , C ⁇ ⁇ C 4 -Al- kyl, -CC 4 -haloalkyl, C.-C 4 -alkoxy, C C-C -haloalkoxy, oxy -CC 4 -alkylthio and -C-C 4 alkoxycarbonyl, can wear, or
  • Triazolyl or imidazole radical the ring in each case one to three substituents selected from Cj_-C alkyl, C ⁇ -C alkoxy, C ! -C -alkylthio and halogen, can carry
  • the organic molecule parts mentioned for the substituents R 1 to R 10 or as residues on phenyl rings or heterocycles, like the meaning halogen, are collective terms for individual lists of the individual group members.
  • All carbon chains, that is to say all alkyl, haloalkyl, alkenyl, Alkynyl, alkoxy, alkenoxy, alkynoxy, alkoxycarbonyl, alkoxyimino, alkylaminocarbonyl, alkoxy (alkylamino) carbonyl, and alkoxyalkyl parts can be straight-chain or branched.
  • Halogenated substituents preferably carry one to five identical or different halogen atoms.
  • C 6 alkyl and the alkyl parts of C 6 alkoxy-C 6 alkyl for: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2- Methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dirnethylpropyl, 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,
  • Ci-Cö-haloalkyl for: Ci-C ⁇ - alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, Chlorodifluoromethyl, 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, 3 -Fluorpropyl, 3-chloropropyl, and heptafluoropropyl, preferably C,
  • C 3 -C 6 alkenyl for: prop-1-en-l-yl, prop-2-en-l-yl, 1-methyl-ethenyl, n-buten-1-yl, n-buten-2-yl , n-buten-3-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl , 2-methyl-prop-2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl - but-1-en-l-yl, 2-methyl-but-l-en-l-yl, 3-methyl-but-1-en-l-yl, l-methyl-but-2-en-l -yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl
  • Phenyl -CC-alkyl e.g. for: benzyl, 1-phenyleth-l-yl, 2-phenyleth-1-yl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, l- Phenylprop-2-yl, 2-phenylprop-2-yl, 1-phenylbut-l-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 1-phenylbut-3-yl, 2-phenylbut-3-yl, l-phenyl-2-methyl-prop-3-yl, 2- Phenyl-2-methyl-prop-3-yl, 3-phenyl-2-methyl-prop-3-yl and 2-benzyl-prop-2-yl, preferably for 2-phenyleth-l-yl
  • Ci-C ⁇ - alkoxy-Ci-Cg-alkyl for: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methyl-propoxy, 2- Methylpropoxy, 1, 1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, n- 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
  • (-C 6 -alkoxy) carbonyl for: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methyl-ethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl, 1,1-dimethylethoxycarbonyl, n-pentoxycarbonyl, 1 -Methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl , 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2, 2-d
  • Hydroxy-Ci-C ⁇ - alkyl for: eg hydroxymethyl, 2-hydroxyeth-1-yl, 2-hydroxyprop-l-yl, 3-hydroxyprop-l-yl, 1-hydroxyprop-2-yl , 2-hydroxy-but-l-yl, 3-hydroxy-but-l-yl, 4-hydroxy-but-l-yl, l-hydroxy-but-2-yl, l-hydroxy-but-3-yl , 2-hydroxy-but-3-yl, l-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, in particular for 2 -hydroxyethyl;
  • Cyano-C ⁇ -C 6 alkyl for: for example cyanomethyl, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop -1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l -yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3-yl , 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;
  • Ci-C ⁇ -alkylthio for: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3 -Methylbutylthio, 2, 2-dirnethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methyl-pentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methyl-pentylthio , 1-Dimethylbutylthio, 1, 2-Dimethylbutylthio, 1,3-Dirnethylbutylthio, 2, 2-D
  • C ⁇ -C 6 -alkylthio-C ⁇ -C 6 alkyl viewed by C ⁇ -C 6 -alkylthio as mentioned above substituted C ß alkyl, eg methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, (l-methylethylthio) methyl , n-Butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, (1, 1-dimethylethylthio) methyl, 2-methylthioethyl, 2-ethylthioethyl, 2- (n-propylthio) ethyl, 2nd - (1-Methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1, 1-di
  • C -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • C -C 6 cycloalkyl-C 3 -C 3 alkyl for: cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1- (cyclopropyl) ethyl, 1- (cyclobutyl) ethyl, 1- (cyclopentyl) ethyl, 1- (cyclohexyl ) ethyl, 2- (cyclopropyl) ethyl, 2- (cyclobutyl) ethyl, 2- (cyclopentyl) ethyl, 2- (cyclohexyl) ethyl, 3- (cyclopropyl) propyl, 3- (cyclobutyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl) propyl, especially for cyclopentylmethyl or cyclohexylmethyl.
  • Preferred benzoic acid derivatives according to the invention are those in which 1 and m in the general formula I have the value 0 and Y represents an oxygen atom.
  • the compounds of the formula I according to the invention can advantageously be prepared in one of the ways described below.
  • the reaction conditions of the individual substeps are known per se to the person skilled in the art and correspond to the usual conditions for such reactions, so that further details are unnecessary here. These reactions are described in detail in the relevant literature.
  • R ⁇ , RSS and R ⁇ independently represent hydrogen, C 1 -C 4 -AI - alkyl, C ⁇ ⁇ C 4 haloalkyl, C 3 -C 6 cycloalkyl or aryl, and R n C ⁇ -C 4 -alkyl.
  • esters la represent precursors for further benzoic acid esters of the formula I according to the invention, which can be obtained by generally customary methods, as is illustrated in the following scheme:
  • U and V are independently an N atom or a methine group.
  • the compounds according to the invention activate defense systems which are latently present in plants against pathogenic microbial influences and thus protect the plant from pathogenic pathogens, in particular harmful fungi.
  • pathogenic pathogens in particular harmful fungi.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where in the case of water as diluent other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) ) and water;
  • Carriers such as natural stone powder (e.g.
  • kaolins, clays, talc, chalk) and synthetic stone powder e.g. highly disperse silica, silicates
  • Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin-,
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • Di-iso-butylnaphthalene-2-sulfonic acid 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite lye and 7 parts by weight of powdered silica gel; a spray mixture is obtained by finely distributing the mixture in water;
  • a stable aqueous dispersion of 40 parts by weight of a compound I according to the invention, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water can be further diluted;
  • IX a stable oily dispersion of 20 parts by weight of a compound I according to the invention, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 50 parts by weight of a paraffinic mineral oil.
  • the compounds according to the invention activate latent defense systems against pathogenic microbial influences in plants, they also act against a broad spectrum of phytopathogenic fungi, in particular from the classes of the deuteromycetes, ascomycetes, phycomycetes and basidiomycetes. Some of them are systemically effective and can be used as leaf and soil fungicides.
  • the compounds are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, lawn, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetable plants such as cucumbers, beans and pumpkin family, as well as on the seeds of these plants.
  • the compounds are applied by treating the seeds, plants, materials or the soil to be protected against fungal attack with a sufficient amount of the active compounds which are immunized against disease.
  • the application takes place as long as possible before the infection of the materials, plants or seeds by the fungi, so that the plants can activate their defensive defense systems.
  • the new compounds are particularly suitable for combating the following plant diseases:
  • Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and turf, Ustilago sugar species on cereals, Ustilago sugar on cereals, Ustilago varieties on cereals, Ustilago sugar varieties on cereals, Ustilago varieties on cereals, Ustilago varieties inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, ornamental plants and vegetables, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryza , Phytophthora infestans on potatoes
  • the crop protection agents against disease generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates are between 0.0025 and 2, preferably 0.1 to 1 kg of active ingredient per ha.
  • active compound 0.001 to 50, preferably 0.01 to 10 g per kg of seed are generally required.
  • agents according to the invention can also be present in the form of use as agents which protect plants against disease, together with other active ingredients, e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers.
  • Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc ethylene diamine bis-dithiocarbamate, tetramethylthiurium dibiammamodisulfide ), Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N '-polypropylene-bis- (thio-carbamoyl) -disulfide;
  • Nitroderivatives such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4, 6-dinitrophenyl-3, 3-dimethylacrylate, 2-sec-
  • heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethyl-phthalimidophosphonothioate, 5-amino-l- [bis - (dimethylamino) -phosphinyl] - 3-phenyl-l, 2, 4-triazole, 2, 3-dicyano-l, 4-dithioanthraquinone, 2-thio-l, 3-dithiolo [4, 5-b] quinoxaline, Methyl 1- (butylcarbamoyl) -2-benzimidazole-carbamate, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl- (4)) -benz -imidazole, N- (1, 1, 2, 2-tetrachloroeth
  • fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethylphenyl) -N-furoyl (2) -alaninate, DL-N- (2, 6-dimethyl-phenyl) -N- (2'-methoxyacetyl) -alanine-methyl ester, N- (2, 6-dimethylphenyl) -N -chloroacetyl-D, L-2-aminobutyrol-acton, DL-N- (2, 6-dimethylphenyl) -N- (phenylacetyl) -alanine methyl ester, 5-methyl-5-vinyl-3- (3, 5- dichlorophenyl) -2, 4-dioxo-l, 3-oxazolidine, 3-
  • Strobilurins such as methyl -E-methoximino- [ ⁇ - (o-tolyloxy) - o-tolyl] acetate, methyl -E- 2- ⁇ 2- [6- (2 -cyanophenoxy) pyridimin-4 -yl-oxy] phenyl ⁇ -3-methoxyacrylate, methyl -E-methoximino- [ ⁇ - (2,5-dimethyloxy) -otolyl] acetamide.
  • Anilino pyrimidines such as N- (4, 6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (l-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-6 - cyclopropyl-pyrimidin-2-yl) aniline.
  • Phenylpyrroles such as 4 - (2, 2-difluoro-1, 3 -benzodioxol-4 -yl) -pyrrole-3-carbonitrile.
  • Cinnamic acid amides such as 3- (chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic acid morpholide.
  • the first fully developed leaves of potted seedlings of the "Chinese snake” variety were specifically prepared with an aqueous preparation of active ingredients, containing a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier was applied to dripping wet, covering the remaining parts of the plant.
  • the plants were cultivated in a greenhouse at temperatures between 22 and 24 ° C. and 60 to 80% relative atmospheric humidity for a week before being inoculated with an aqueous spore suspension of Colletotrichum lagenarium, the causative agent of the cucumber focal spot disease.
  • the plants were then cultivated for another week at temperatures between 24 and 28 ° C and almost 100% relative humidity. The extent of disease development on the individual leaf days was then determined visually as% infestation of the leaf surface.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des dérivés d'acide benzoïque correspondant à la formule générale (I), dans laquelle les substituants ont la signification donnée dans la description.
PCT/EP1998/007920 1997-12-08 1998-12-05 Derives d'acide 3-pyrazol-1-yl-benzoique WO1999029671A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19754301.4 1997-12-08
DE19754301 1997-12-08

Publications (1)

Publication Number Publication Date
WO1999029671A1 true WO1999029671A1 (fr) 1999-06-17

Family

ID=7851059

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/007920 WO1999029671A1 (fr) 1997-12-08 1998-12-05 Derives d'acide 3-pyrazol-1-yl-benzoique

Country Status (1)

Country Link
WO (1) WO1999029671A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0138527A2 (fr) * 1983-10-08 1985-04-24 Nippon Kayaku Kabushiki Kaisha Dérivés de pyrazole à activité herbicide
EP0269806A1 (fr) * 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
EP0558999A2 (fr) * 1992-03-02 1993-09-08 Bayer Ag Dérivés de pyrazole N-arylé comme herbicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0138527A2 (fr) * 1983-10-08 1985-04-24 Nippon Kayaku Kabushiki Kaisha Dérivés de pyrazole à activité herbicide
EP0269806A1 (fr) * 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
EP0558999A2 (fr) * 1992-03-02 1993-09-08 Bayer Ag Dérivés de pyrazole N-arylé comme herbicides

Similar Documents

Publication Publication Date Title
EP1017670B1 (fr) Derives de benzamidoxime, produits intermediaires et procedes pour les preparer et les utiliser comme fongicides
EP0847388B1 (fr) Derives de biphenylamide a substitution heterocyclique, leur preparation et leur utilisation comme fongicides
EP1003725B1 (fr) Fluorpyrazole-biphenylamides fongicides
DE4142514A1 (de) Verfahren zur bekaempfung von pilzen
EP1085807B1 (fr) Utilisation de 2-(n-phenylamino)pyrimidines comme fongicides et nouvelles 2-(n-phenylamino)pyrimidines
WO2001030154A2 (fr) Compositions agrochimiques contenant des pyrazols comme principes actifs et leur utilisation comme phytosanitaires a action fongicide
EP0617891B1 (fr) Procédé pour le combat des moisissures agricoles et 2-aniline-pyridines.
EP0336211B1 (fr) Ethers phénoliques substitués en position ortho et fongicides les contenant
EP1172355B1 (fr) Dérivés de l'acide salicylique, procédé pour leur préparation, agents les contenant ainsi que leur utilisation pour lutter contre les champignons nuisibles
EP0984686B1 (fr) Procede pour lutter contre les champignons nuisibles
EP0808102B1 (fr) Agent fongicide
WO1999029671A1 (fr) Derives d'acide 3-pyrazol-1-yl-benzoique
WO1999014188A1 (fr) Nouveaux derives de benzamidoxime, produits intermediaires et procedes pour les preparer et leur utilisation comme fongicides
EP1133229B1 (fr) Produits fongicides contenant comme principes actifs des pyrrolidones
EP1218339B1 (fr) Derives de benzylamidoxime, produits intermediaires et procede servant a la preparation desdits derives, ainsi que leur utilisation comme fongicides
DE19504599A1 (de) Fungizides Mittel
WO2001062087A2 (fr) Produit fongicide contenant des pyrrolidones comme principes actifs et leur utilisation lors du traitement de plantes
EP0941988A2 (fr) Dérivés de benzamidoximes, produits intermédiaires et procédé de leur préparation et leur utilisation comme fongicides
EP0657418A1 (fr) Acylaminobenzamides et fongicides les contenant
EP0664283A1 (fr) Dérivés p-phenylènediamine et agents fongicides les contenant
DE19636509A1 (de) Fungizide Chinoline
EP1118609A2 (fr) Benzylphényléthers iminooxi-sunstitués, procédé et intermédiaires pour leur préparation, agents les contenant ainsi que leur utilisation pour lutter contre les champignons nuisibles
WO2000017156A1 (fr) Nouveaux derives de benzamidoxime, produits intermediaires et procedes permettant de les preparer et leur utilisation comme fongicides
DE19857273A1 (de) Fungizide Mittel enthaltend als Wirkstoffe 2-Oxa-1,3,6,7-tetraaza-cyclopenta[alpha]naphthalin-Derivate und deren Verwendung bei der Behandlung von Pflanzen
WO2002072523A1 (fr) Benzophenones, leur production et leur utilisation dans la lutte de champignons pathogenes pour les vegetaux

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP MX US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA