EP1861369A1 - Anilides d'acide nicotinique, procedes de fabrication et agents fongicides contenant ces composes - Google Patents

Anilides d'acide nicotinique, procedes de fabrication et agents fongicides contenant ces composes

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Publication number
EP1861369A1
EP1861369A1 EP06708777A EP06708777A EP1861369A1 EP 1861369 A1 EP1861369 A1 EP 1861369A1 EP 06708777 A EP06708777 A EP 06708777A EP 06708777 A EP06708777 A EP 06708777A EP 1861369 A1 EP1861369 A1 EP 1861369A1
Authority
EP
European Patent Office
Prior art keywords
nicotinamide
chloro
trifluoromethyl
methyl
formula
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.)
Withdrawn
Application number
EP06708777A
Other languages
German (de)
English (en)
Inventor
Markus Gewehr
Jochen Dietz
Thomas Grote
Carsten Blettner
Wassilios Grammenos;
Udo HÜNGER
Bernd Müller
Frank Schieweck
Anja Schwögler
Jan Klaas Lohmann
Joachim Rheinheimer
Peter Schäfer
Siegfried Strathmann
Reinhard Stierl
Jan Rether
Karl Eicken
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1861369A1 publication Critical patent/EP1861369A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

Definitions

  • Nicotinic acid anilides process for their preparation and compositions containing them for controlling harmful fungi
  • the present invention is a.
  • n 0.1 or 2; m 2 or 3;
  • X 2 is halogen, where the radicals X 2 may have different meanings;
  • Y is CN, NO 2, -C 4 -alkyl, C r C 4 haloalkyl, methoxy or methylthio;
  • p is zero or 1;
  • R 1 is halogen, methyl, C 1 -C 4 -haloalkyl, methoxy, methylthio, methylsulfinyl or methylsulfonyl;
  • R 2 is hydrogen, methyl or ethyl; W oxygen or sulfur.
  • the invention relates to processes for the preparation of these compounds, compositions containing them and processes for their use for controlling harmful fungi.
  • Nicotinic acid anilides with fungicidal activity are known from the literature.
  • EP-A 545 099 describes biphenylanilides of this type which have monosubstitution on the biphenyl group.
  • Amide group have a very specific substitution with unsaturated radicals.
  • the compounds of the formula I have an over the known compounds improved activity against harmful fungi.
  • the compounds of the formula I can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.
  • halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
  • C 1 -C 4 -alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, preferably methyl or ethyl;
  • C 1 -C 4 -haloalkyl represents a partially or completely halogenated C 1 -C 4 -alkyl radical, where the halogen atom (s) is / are in particular fluorine and / or chlorine, ie, for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, diflu oromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2,2-trifluoroethyl, 2 Chloro-1,1,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2-bromo-2,2-difluoroethyl
  • the compounds I are generally obtained by reacting a carboxylic acid halide of the formula II in a manner known per se (for example, March, Advanced Organic Chemistry, 2nd Ed., 382 f., McGraw-Hill, 1977) in the presence of a Base reacted with an aniline of formula III:
  • the radical Hal in the formula II represents a halogen atom such as fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine or bromine.
  • This reaction is usually carried out at temperatures of (-2O) 0 C to 100 0 C, preferably 0 0 C to 50 ° C.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and methylene chloride, dimethylsul
  • Bases generally include inorganic compounds, e.g. Alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate and alkali metal hydrogencarbonates such as sodium bicarbonate and organometallic compounds, in particular alkali metal lalkyle such as methyllithium, butyl lithium and phenyllithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alkoxides such as sodium, sodium, potassium, potassium tert .
  • Butanolate and dimethoxymagnesium also organic bases, eg tertiary amines such as trimethylamine, triethylamine, di-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration.
  • organic bases eg tertiary amines such as trimethylamine, triethylamine, di-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration.
  • Triethylamine and pyridine are particularly preferably used.
  • the bases are generally used in equimolar amounts based on the compound II. But they can also be used in an excess of 5 mol% to 30 mol%, preferably 5 mol% to 10 mol%, or - in the case of using tertiary amines - optionally as a solvent.
  • the starting materials are generally reacted with each other in approximately equimolar amounts. It may be advantageous for the yield to use II in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%, based on III.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,
  • Cyclohexane and petroleum ether aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile , Ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide, more preferably methylene chloride, toluene and tetrahydrofuran.
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • halogenated hydrocarbons such as methylene
  • Suitable dehydrating agents are 1, 1'-carbonyldiimidazole, bis (2-oxo-3-oxazolidinyl) phosphoryl chloride, carbodiimides such as N, N'-dicyclohexylcarbodiimide and N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide, phosphonium salts such as (benzotriazole-1 - yloxy) tris (dimethylamino) phosphonium hexafluorophosphate, bromotripyrrolidinophosphonium hexafluorophosphate, bromotris (dimethylamino) phosphonium hexafluorophosphate and Chlorotripyrrolidinophosphonium hexafluorophosphate, uronium and thiuronium salts such as O- (benzotriazol-1-yl) -N, N, N ', N'-t
  • Suitable organic bases are tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methyl-piperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylamino-pyridine and bicyclic amines. Triethylamine and pyridine are particularly preferably used.
  • the bases are generally used in excess of from 10 mol% to 200 mol%, preferably from 50 mol% to 150 mol%, based on the compound IV.
  • the starting materials are generally reacted in approximately equimolar amounts with one another. It may be advantageous for the yield to use one of the compounds in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%.
  • the dehydrating agents are generally used in excess of from 5 mol% to 100 mol%, preferably from 5 mol% to 60 mol%.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, as well as dimethyl sulfoxide and dimethylformamide, particularly preferably diethyl ether, tert-butyl methyl ether, tetrahydrofuran and dimethylformamide.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether
  • aromatic hydrocarbons such as toluene, o-, m- and p-xy
  • Suitable alkylating agents are alkyl halides such as methyl iodide, ethyl iodide, methyl bromide, ethyl bromide, methyl chloride and ethyl chloride, alkyl (perfluoroalkyl sulfonates) such as methyl trifluoromethyl sulfonate and ethyl trifluoromethyl sulfonate, alkyl (alkyl sulfonates) such as methyl methyl sulfonate and ethyl methyl sulfonate, alkyl (arylsulfonate ) such as methyl p-tolylsulfonate and ethyl p-tolylsulfonate, oxonium salts such as trimethyloxonium tetrafluoroborate and triethyloxonium tetrafluoroborate.
  • alkyl halides such as methyl
  • methyl iodide ethyl iodide
  • methyl bromide ethyl bromide
  • chloride methyl chloride
  • ethyl chloride ethyl chloride
  • Suitable bases are generally inorganic compounds, for example alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride Alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydrogen carbonates such as sodium bicarbonate or organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyl-lithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium
  • the bases are generally used in approximately equimolar amounts based on the compound I. However, they can also be used in an excess of 5 mol% to 30 mol%, preferably 5 mol% to 10 mol%.
  • the starting materials are generally reacted with each other in approximately equimolar amounts. However, it may also be advantageous for the yield to use the alkylating agent in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%, based on I.
  • Those compounds I 1 in which W is sulfur can also be prepared by sulfurization of the corresponding compounds I 1 in which W is oxygen (cf., for example, D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976 ) and WO 01/42223).
  • n zero; X 1 chlorine; X 2 F or Cl, in particular fluorine;
  • Y -C 4 -alkyl, Ci-C4-haloalkyl or methoxy in particular methyl, difluoro- methyl, trifluoromethyl or methoxy; particularly preferably methyl or trifluoromethyl; p zero;
  • R 1 is halogen, methyl, trifluoromethyl or methoxy, in particular F 1 Cl 1 methyl or
  • trifluoromethyl particularly preferably fluorine, chlorine or trifluoromethyl, in particular chlorine or
  • Trifluoromethyl most preferably chlorine
  • R 2 is hydrogen or methyl, in particular hydrogen
  • W oxygen is hydrogen
  • radicals X 2 are preferably in the 2,4,5- or 3,4,5-position, in particular in the 3,4,5-position.
  • Y -C 4 alkyl, -C 4 haloalkyl or methoxy in particular methyl, Difluorme- methyl, trifluoromethyl or methoxy
  • R 1 is halogen, methyl, trifluoromethyl or methoxy, in particular fluorine, chlorine, methyl or trifluoromethyl
  • R 2 is hydrogen or methyl
  • W oxygen
  • R 1 is F, Cl, methyl or trifluoromethyl, in particular fluorine or chlorine; R 2 is hydrogen; W oxygen.
  • compounds I with m 2, in particular those in which n is zero, p is zero, R 1 is fluorine or chlorine, in particular chlorine, and R 2 is hydrogen.
  • radicals X are preferably in the 2,4- or 3,4-position, in particular in the 3,4-position.
  • Table 4 Compounds of the general formula IA, in which R 1 is trifluoromethyl and R 2 is hydrogen and B corresponds in each case to one row of Table A.
  • Table 8 Compounds of the general formula IA, in which R 1 is methyl and R 2 is methyl and B corresponds in each case to one row of Table A.
  • Table 13 Compounds of the general formula IA, in which R 1 is methyl and R 2 is ethyl and B corresponds in each case to one row of Table A.
  • Table 18 Compounds of the general formula IB in which R 1 is methyl and B corresponds in each case to one row of Table A.
  • the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Peronosporomyces (syn. Oomycetes) and Basidiomycetes. They are sometimes systemically effective and can be used in crop protection as foliar, soil and Beizfungizide.
  • Alternaria species on vegetables, rapeseed, sugar beets and fruits and rice e.g. A. solani or A. alternata on potatoes and tomatoes, - Aphanomyces species on sugar beet and vegetables,
  • Fusarium and Verticillium species on various plants e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, e.g. Tomatoes, - Gaeumanomyces graminis on cereals,
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi on rice
  • Pseudoperonospora on various plants e.g. P. cubensis on cucumber or P. humili on hops,
  • Venturia species scab
  • apples and pears e.g. V. inaequalis to apple.
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidi- omycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., P / et / rotus spp., Porta spp., Serpula spp.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • seed treatment e.g. by dusting, coating or impregnating seed
  • active substance e.g. by dusting, coating or impregnating seed
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound I according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active compound with solvents and / or excipients, if desired with use of emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • aromatic solvents eg Solvesso ® products, XyIoI
  • paraffins eg petroleum fractions
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • ketones eg cyclohexanone, gamma-butyrolactone
  • pyrrolidones N-methylpyrrolidone and NOP
  • acetates glycols, dimethyl fatty acid amides, fatty acids and
  • Fatty acid ester In principle, solvent mixtures can also be used.
  • - Carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Seed treatment formulations may additionally contain binders and / or gelling agents and optionally dyes.
  • Binders can be added to increase adhesion of the active ingredients to the seed after treatment.
  • Suitable binders are for example EO / PO block copolymer surfactants, but late also polyvinyl alcohols, Ppolyvinylpyrrolidone, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrenes, polyethyleneamines, Polyethylenamide, polyethylenimines (Lupasol ®, Polymin ®), polyethers, polyurethanes, polyvinyl acetates, Tylose and Copolymers of these polymers.
  • a suitable gelling agent is, for example, carrageen (Satiagel ®).
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active compound I.
  • the active compounds are in a purity of 90% to 100%, preferably 95% % to 100% (according to NMR spectrum) used.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • the formulations in question give, after dilution of from two to ten times, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
  • formulations are: 1. Products for dilution in water
  • a compound I according to the invention 10 parts by weight of a compound I according to the invention are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with an active ingredient content of 10% by weight.
  • a compound I according to the invention 20 parts by weight of a compound I according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone solved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight.
  • a compound I according to the invention 20 parts by weight of a compound I according to the invention are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to give a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • 50 parts by weight of a compound I according to the invention are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • WP, SP Water-dispersible and Water-Soluble Powders (WP, SP) 75 parts by weight of a compound I according to the invention are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • a compound I according to the invention are finely ground and with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
  • the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
  • the forms of application depend entirely on the purposes of use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just before use (tank mix), are added. These agents can usually be mixed into the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • the agents according to the invention in the form of use as fungicides, may also be present together with other active substances, e.g. with herbicides, insecticides, growth regulators such as Prohexadion-Ca, fungicides or with fertilizers.
  • active substances e.g. with herbicides, insecticides, growth regulators such as Prohexadion-Ca, fungicides or with fertilizers.
  • Azoxystrobin dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate;
  • bitertanol bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriafol, Hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimol, triadimefon, triticonazole;
  • - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole; Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • Dicarboximides iprodione, procymidone, vinclozolin;
  • guanidines dodin, iminoctadine, guazatine
  • Antibiotics Kasugamycin, Polyoxin, Streptomycin, Validamycin A; Organometallic compounds: fentin salts;
  • Sulfur-containing heterocyclyl compounds isoprothiolane, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Nitrophenyl derivatives binapacryl, dinocap, dinobuton;
  • - Inorganic active substances Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur;
  • Example 1 ⁇ Aß ⁇ '- dichlorobiphenyl ⁇ -yl ⁇ -ttrifluormethyOnicotinamid
  • 2- (trifluoromethyl) nicotinic acid a solution of 0.20 g of 2- (trifluoromethyl) nicotinic acid and 0.21 g of triethylamine in 30 ml dichloromethane at 0 0 C 0.25 g of 3'.
  • the mixture was stirred at 0 ° C. for 15 minutes and then at room temperature for 12 hours.
  • the active compounds were prepared as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or dimethyl sulfoxide and the emulsifier Uniperol ® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkyl kylphenole) in the volume ratio solvent Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the desired drug concentration.
  • Leaves of potted plants of the "Golden Queen" variety were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below.
  • the leaves were infected with an aqueous spore suspension of Alternaria solani 'm 2% biomalt solution having a density of 0.17 ⁇ 10 6 spores / ml.
  • the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days, the disease on the untreated, but infected control plants had developed so strongly that the infestation could be determined visually in%.

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

Abstract

L'invention concerne des anilides d'acide nicotinique représentés par la formule (I) dans laquelle n = 0, 1, 2 ; m = 2, 3 ; X<SUP>1</SUP> = F, chlore ; X<SUP>2</SUP> = halogène ; Y = CN, NO<SUB>2</SUB>, C<SUB>1</SUB>-C4-alkyle, C<SUB>1</SUB>-C<SUB>4</SUB>-halogénoalkyle, méthoxy, méthylthio ; p = 0, 1 ; R<SUP>1</SUP> = halogène, méthyle, CrC4-halogénoalkyle, méthoxy, méthylthio, méthylsulfinyle, méthylsulfonyle ; R<SUP>2</SUP> = hydrogène, méthyle, éthyle ; et, W = O, S. L'invention concerne également des procédés de fabrication de ces composés, des agents les contenant, des semences et des procédés de lutte contre les champignons parasites.
EP06708777A 2005-03-16 2006-03-15 Anilides d'acide nicotinique, procedes de fabrication et agents fongicides contenant ces composes Withdrawn EP1861369A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005012485 2005-03-16
PCT/EP2006/060754 WO2006097490A1 (fr) 2005-03-16 2006-03-15 Anilides d'acide nicotinique, procedes de fabrication et agents fongicides contenant ces composes

Publications (1)

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EP1861369A1 true EP1861369A1 (fr) 2007-12-05

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CN105432620B (zh) * 2015-01-12 2017-11-14 四川利尔作物科学有限公司 杀菌组合物及其应用
RU2017132315A (ru) * 2015-02-18 2019-03-18 Байер Кропсайенс Акциенгезельшафт Замещенные 2-дифторметил-никотин(тио)карбоксанилидные производные и их применение в качестве фунгицидов
UY36887A (es) 2015-09-07 2017-03-31 Bayer Cropscience Ag Derivados heterocíclicos condensados sustituidos por 2-(het)arilo como pesticidas
CN113912534B (zh) * 2021-11-10 2023-07-25 江苏科技大学 一种联苯类杂环化合物、其合成方法及其应用

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IL103614A (en) * 1991-11-22 1998-09-24 Basf Ag Carboxamides for controlling botrytis and certain novel such compounds
DE4231517A1 (de) * 1992-09-21 1994-03-24 Basf Ag Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen
JP2001302605A (ja) * 2000-04-20 2001-10-31 Sumitomo Chem Co Ltd ビフェニル化合物およびその用途
EA005777B1 (ru) * 2001-01-18 2005-06-30 Басф Акциенгезельшафт Фунгицидные смеси

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WO2006097490A1 (fr) 2006-09-21
AR053176A1 (es) 2007-04-25
JP2008533097A (ja) 2008-08-21
US20080171774A1 (en) 2008-07-17
CN101142190A (zh) 2008-03-12
BRPI0608709A2 (pt) 2010-01-26

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