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WO1994001403A1 - Derives de piperidine - Google Patents

Derives de piperidine Download PDF

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Publication number
WO1994001403A1
WO1994001403A1 PCT/EP1993/001777 EP9301777W WO9401403A1 WO 1994001403 A1 WO1994001403 A1 WO 1994001403A1 EP 9301777 W EP9301777 W EP 9301777W WO 9401403 A1 WO9401403 A1 WO 9401403A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
general formula
phenyl
alkyl
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
Application number
PCT/EP1993/001777
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English (en)
Inventor
Paul Andrew Carter
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.)
Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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Publication date
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Priority to AU45660/93A priority Critical patent/AU4566093A/en
Publication of WO1994001403A1 publication Critical patent/WO1994001403A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms

Definitions

  • the present invention relates to a method of combating fungi using certain piperidine derivatives, some of which are novel, processes for their preparation, compositions containing such compounds and their use as fungicides for the control of phytopathogenic fungi.
  • R represents a C. .. alkyl, C 2 _ 20 alkoxyalkyl, C 2 . 2 o hydroxyalkyl, C 3 12 cycloalkyl, C ⁇ 2Q alkylcycloalkyl, C,tician» cycloalkylalkyl, aryl, haloaryl, C_ aralkyl, C. 20 haloaralkyl or C ? 20 aryloxyalkyl, m is 1 or 2 and n is 0 or 1.
  • Compounds in which m is 2, that is piperidine derivatives substituted at the 1- and 4- positions, and n is 0 are said to be especially preferred.
  • WO-A-9202502 describes the preparation of
  • J63179850 describes the preparation of N-(2,3-dihydroxy- 3,7,ll-trimethyldodec-l-yl)-4-(2-phenylethyl)piperidine as an allergy inhibitor and brain function improver.
  • Synth. Commun. , 88, Vol. 18(12), pp. 1331-7 discloses N-methyl-4-(3-phenylpropyl)- piperidine and Fresenius' Z. Anal. Chem.
  • FR M 2239 (CA. 60:15839 d) discloses N-[2-(dimethylamino)ethyl)-4-(2-phenyl- ethyl)piperidine and its dihydrochloride, the latter being useful in the treatment of atherosclerosis.
  • US 4033971 describes the preparation of N-methyl-4- [2-(2-methylphenyl)ethyl]piperidine.
  • FR 1489505 describes the preparation of N-(2-hydroxyethyl)-4-(3- phenylpropyl)piperidine hydrochloride and N-(2-chloroethyl)-4-(3- phenylpropyl)piperidine hydrochloride and US 3352873 describes the preparation of N-(4-hydroxybutyl)-4-(3-phenylpropyl)piperidine and N-(2-hydroxyethyl)-4-(3-phenylpropyl)piperidine.
  • any of the compounds disclosed therein exhibit fungicidal activity.
  • the present invention therefore relates to a method of combating fungi at a locus which comprises treating the locus with a compound of the general formula
  • R represents an aryl group which may be substituted by one or more substituents
  • R represents a hydrogen atom or an alkyl or phenyl group, represents a hydrogen atom or an alkyl or phenyl group, R represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl group, m represents an integer from 0 to 3, and n represents an integer from 0 to 2.
  • the locus to be treated especially comprises plants subject to or subjected to fungal attack, seeds of such plants or the medium in which the plants are growing or are to be grown.
  • R represents an optionally substituted aromatic hydrocarbyl group.
  • R in particular represents a phenyl or naphthyl group, optionally substituted by one or more halogen atoms or hydroxy, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, arylamino, formyl, alkylcarbonyl, alkoxycarbonyl, carboxyl, phenyl, halophenyl or phenoxy groups.
  • R represents a phenyl group optionally substituted by one or more fluorine, chlorine or bromine atoms, cyano, C , alkyl, C. haloalkyl, C. , alkoxy, C , haloalkoxy, C , alkylamino, di-C. alkylamino, C. , alkoxycarbonyl, or phenyl groups.
  • the invention especially relates to a method in which R 2 and
  • R represent hydrogen or a C , alkyl group, more especially a
  • R and R represent hydrogen.
  • the invention further especially relates to a method in which 4 R represents an alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, naphthyl, pyridyl, thienyl, pyrimidyl or furyl group, each group optionally substituted by one or more substituents selected from halogen atoms or nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, arylamino, formyl, alkylcarbonyl, alkoxycarbonyl, carboxyl, phenyl, halophenyl or
  • R represents a C . synonym alkyl, C alkenyl, C _ alkynyl, C, g cycloalkyl, phenyl, pyridyl or thienyl group, each group being optionally substituted by one or more substituents selected from fluorine, chlorine or bromine atoms or C alkyl, C , haloalkyl, C. , alkoxy, C , haloalkoxy, C alkylamino, di-C. , alkylamino, C alkylcarbonyl, C alkoxycarbonyl, or phenyl groups.
  • R represents a C, g alkyl, C _ alkenyl, C_ g alkynyl, C, , cycloalkyl, naphthyl, phenyl, pyridyl or thienyl group, optionally substituted by one or more substituents selected from halogen atoms, especially fluorine, chlorine and bromine atoms, nitro, cyano, C , alkyl, C. . haloalkyl, C. , alkoxy, C. , alkylcarbonyl, C. , alkoxycarbonyl, phenyl, halophenyl, and phenoxy groups.
  • the invention especially relates to a method in which m represents 0, 1 or 2.
  • the alkylene group which connects R and the piperidine ring may optionally be substituted by one or more halogen atoms or one or more C , alkyl groups, especially methyl or ethyl groups.
  • the chain is substituted by a fluorine, chlorine or bromine atom or a methyl group.
  • a particularly preferred sub-group of compounds of the general formula I that may be used in the method of the invention is that in which R represents a phenyl, butylphenyl, methylphenyl,
  • R represents a phenyl, fluorophenyl, chlorophenyl, dichlorophenyl, bromophenyl, nitrophenyl, methylphenyl, butylphenyl, methoxyphenyl, methoxycarbonylphenyl, trifluoromethylphenyl, biphenyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl group and m represents 0, 1 or 2.
  • Alkyl as substituent or as part of other substituents, such as alkoxy, alkoxycarbonyl etc. may contain up to 12, preferably up to 6, and especially up to 4, carbon atoms and includes the following straight-chain or branched groups depending on the number of carbon atoms indicated: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc. as well as their isomers such as isopropyl, isobutyl, tertiary-butyl, isopentyl.
  • Halogen includes fluorine, chlorine, bromine or iodine, especially fluo ⁇ rine, chlorine and bromine.
  • Cycloalkyl may contain 3 to 8, prefer ⁇ ably 3 to 6, carbon atoms and includes the following substituents depending on the number of carbon atoms indicated: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl etc.
  • An aryl group may be any aromatic hydrocarbon group, especially a phenyl or naphthyl group.
  • substituents of alkyl, alkenyl, cycloalkyl and phenyl etc. preferably are halogen, methoxy, nitro, amino, cyano and, in the case of cycloalkyl and phenyl, also methyl and trifluoromethyl.
  • Heterocyclyl groups are especially 5- or 6-membered heterocycles, preferably saturated or unsaturated 5- or 6-membered heterocycles containing one to four of the same or different heteroatoms such as nitrogen, oxygen or sulphur.
  • substituent groups which are optionally present may be one or more of those customarily employed in the development of fungicidal compounds and/or the modification of such compounds to influence their structure/activity, persistence, penetration or other properties.
  • substituents include, for example, halogen atoms, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, formyl, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, phenyl, halophenyl and phenoxy groups.
  • the compounds of formula I may form acid addition salts with a variety of acids.
  • acid addition salts with acids such as aliphatic and aromatic carboxylic acids, such as acetic, lauric, benzoic, oxalic, lactic, and mandelic acids, aliphatic and aromatic sulphonic acids, such as dodecylbenzenesulphonic acid, saccharin, an mineral acids such as phosphonic and hydrochloric acid, are especially preferred.
  • Preferred acid addition salts are plant-physiologically acceptable salts.
  • I are capable of existing as different geometric isomers and diastereomers.
  • the invention includes both the individual isomers and mixtures of isomers.
  • R does not represent a methyl group
  • the present invention also provides a process for the preparation of a compound of the general formula I as defined above or an acid addition salt thereof which comprises reacting a compound of the general formula
  • the leaving group is a halogen, especially a chlorine or bromine atom or a sulphonate group, such as a methyl sulphonate or toluenesulphonate group.
  • the process of the present invention is conveniently carried out in the presence of a solvent.
  • Suitable solvents include ethers, particularly tetrahydrofuran, alcohols, particularly ethanol, and dimethylformamide.
  • the reaction is suitably carried out at a temperature between 0 °C and 160 °C, the preferred reaction temperature being between 20 °C and 120 °C It is also preferred that the reaction is carried out in the presence of a base, such as potassium carbonate.
  • Compounds of the general formula II in which R is as defined above and n represents 0 may be conveniently prepared by reaction of an optionally substituted bromo- or iodo-phenyl compound with (4-)vinyl substituted pyridine in the presence of a suitable noble and/or transition metal catalyst, preferably a palladium catalyst, followed by hydrogenation of the obtained product. These reactions are described by R.F. Heck in Org. Reactions, 1982, 2_7, 345 and in Comprehensive Organic Chemistry, 1991, vol. 8, 497, Eds. B.M. Trost and I. Fleming, Pergamon Press. Alternatively, compounds of the general formula II in which R is as defined above and n represents 0 may be prepared by reacting an appropriate benzaldehyde with 4-picoline and acetic acid anhydride, followed by hydrogenation of the product so obtained.
  • 1 may be prepared by reaction of an appropriate acetophenone with 4-pyridine carboxaldehyde in the presence of, for example, piperidine and acetic acid, followed by hydrogenation of the
  • 25 group which is chemically stable to hydrogenation may be prepared as described above.
  • R represents a group which is susceptible to hydrogenation
  • compounds of formula II may, for instance, be conveniently prepared from compounds of formula II in which R represents an amino-substituted aryl group via a Sandmeyer
  • the invention also provides fungicidal compositions comprising at least one of the compounds according to general formula I or an acid addition salt thereof, as well as methods of combating fungi at a locus comprising treatment of the locus with a compound of formula I or an acid addition salt thereof as defined hereinbefore, or with a composition as defined in this specification.
  • the fungicidal composition comprises a carrier and, as active ingredient, a compound of the general formula I or an acid addition salt thereof.
  • a method of making such a composition comprises bringing a compound of the general formula I as defined above or an acid addition salt thereof into association with at least one carrier.
  • a composition may contain a single compound or a mixture of several compounds of the present invention. It is also envisaged that different isomers or mixtures of isomers may have different levels or spectra of activity and thus compositions may comprise individual isomers or mixtures of isomers.
  • the invention further relates to the use as a fungicide of a compound of formula I as defined hereinbefore or a composition as defined hereinbefore.
  • a composition according to the invention preferably contains from 0.5 to 95% by weight of active ingredient.
  • a carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soil, or to facilitate storage, transport or handling.
  • a carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formulating fungicidal compositions may be used.
  • Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarone resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes, for example beeswax, paraffin wax, and chlorinated mineral waxes; and solid fertilisers, for example superphosphates.
  • natural silicas such as diatomaceous earths
  • magnesium silicates for example talcs
  • magnesium aluminium silicates for example attap
  • Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example, kerosine and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable.
  • Fungicidal compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application.
  • a carrier which is a surface-active agent facilitates this process of dilution.
  • at least one carrier in a composition according to the invention is a surface-active agent.
  • the composition may contain at least two carriers, at least one of which is a surface-active agent.
  • a surface-active agent may be an emulsifying agent, a dispers ⁇ ing agent or a wetting agent; it may be nonionic or ionic.
  • Exam- pies of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, ° sorbitol, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example p-octylphenol or £-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of
  • compositions of the invention may for example be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and 5 aerosols.
  • Wettable powders usually contain 25, 50 or 75% w of active ingredient and usually contain in addition to solid inert carrier, 3-10% w of a dispersing agent and, where necessary, 0-10% w of stabiliser(s) and/or other additives such as penetrants or stickers.
  • Dusts are usually formulated as a dust concentrate 0 having a similar composition to that of a wettable powder but without a dispersant, and may be diluted in the field with further solid carrier to give a composition usually containing h-10% w of active ingredient.
  • Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676 - 0.152 mm), and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain 4-75% w active ingredient and
  • Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 1-50% w/v active ingredient, 2-20% w/v emulsifiers and
  • Suspension concentrates are usually compounded so as to obtain a stable, non-sedimenting flowable product and usually contain 10-75% w active ingredient, 0.5-15% w of dispersing agents, 0.1-10% w of suspending agents such as protective colloids and thixotropic agents, 0-10% w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.
  • Aqueous dispersions and emulsions for example compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the invention.
  • the said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnaise' like consistency.
  • composition of the invention may also contain other ingredients, for example other compounds possessing herbicidal, insecticidal or fungicidal properties.
  • a carrier which will provide a slow release of the fungicidal compounds into the environment of the plant which is to be protected.
  • Such slow-release formulations could, for example, be inserted in the soil adjacent to the roots of a vine plant, or could include an adhesive component enabling them to be applied directly to the stem of a vine plant.
  • the present invention still further provides the use as a fungicide of a compound of the general formula I as defined above or a composition as defined above, especially the use as a fungicide against fungicidal diseases in cereals.
  • the present invention is of wide applicability in the protection of crop plants against fungal attack.
  • Typical crops which may be protected include cereals, especially wheat and barley, rice, vines, potatoes, tomatoes, pome fruit, especially apples, and cucumber.
  • the duration of protection is normally dependent on the individual compound selected, and also a variety of external factors, such as climate, whose impact is normally mitigated by the use of a suitable formulation.
  • the compounds of the general formula II and the acid addition salt thereof also exhibit fungicidal activity.
  • the compounds of the general formula II in which R represents phenyl or t-butyl phenyl and n represents 2 and 0 respectively show good activity against Plasmopara viticola and Venturia inaequalis.
  • the present invention also relates to the compounds of the general fomula II or the acid addition salts thereof and to fungicidal compositions containing one or more compounds of the general formula II or the acid addition salts thereof, as well as to the use of the compounds of general formula II or the acid addition salts thereof or compositons containing these compounds as fungicides.
  • the preferred embodiments for R and n correspond with the preferred embodiments for R and n in the general formula I as defined hereinafter.
  • the other definitions with respect to the compounds of the general Formula II correspond with the other definitions with respect to the compounds of the general Formula I, including the acid addition salts, the isomers, the compositions, the method of combating fungi and the use.
  • Example 1 The invention is further illustrated by the following examples.
  • Example 1 The invention is further illustrated by the following examples.
  • the fungicidal activity of compounds of the invention was investigated by means of the following tests.
  • the test is a direct antisporulant one using a foliar spray.
  • the test is a direct protectant one using a foliar spray.
  • the upper surfaces of leaves of broad bean plants (cv The Sutton) are sprayed with the test compound at a dosage of 1000 ppm using an automated sprayline as described under (a) .
  • 24 hours after spraying the leaves are inoculated with an aqueous suspension containing 10 conidia/ml.
  • For 4 days after inoculation plants are kept moist in a humidity compartment at 22 ⁇ C Disease is assessed 4 days after inoculation, based on the percentage of leaf surface area covered by lesions.
  • Leaves of wheat plants (cv Norman), at the single leaf stage, are inoculated by spraying with an aqueous suspension containing 1.5 x 10 spores/ml.
  • the inoculated plants are kept for 24 hours in a high humidity compartment prior to treatment.
  • the plants are sprayed with a solution of the test compound at a dosage of 1000 ppm using an automated sprayline as described under (a) .
  • After drying, the plants are kept for 6-8 days at 22 C and moderate humidity, followed by assessment. Assessment is based on the density of lesions per leaf compared with that on leaves of control plants.
  • the test is a direct therapeutic one, using a foliar spray.
  • Leaves of barley seedlings, (cv. Golden Promise) are inoculated by dusting with mildew conidia one day prior to treatment with the test compound.
  • the inoculated plants are kept overnight at glasshouse ambient temperature and humidity prior to treatment.
  • the plants are sprayed with the test compound at a dosage of 1000 ppm using an automated sprayline as described under (a) . After drying, plants are returned to a compartment at 18 ⁇ C and moderate humidity for up to 7 days, followed by assessment. Assessment is based on the percentage of leaf area covered by sporulation compared with that on leaves of control plants.
  • V. inaequalis that causes apple scab.
  • the test compound in acetone is added into 4 ml aliquots of half strength Potato Dextrose Broth dispensed in 25-compartment petri dishes to give final concentrations of 100 ppm.
  • the fungal inoculum consists of mycelial fragments and spores of V. inaequalis grown on malt agar
  • Petri dishes are incubated at 20°C for 10 days until the assessment of mycelial growth.
  • the leaves of rice seedlings (cv Aichiaishi - about 30 seedlings per pot) are sprayed with an aqueous suspension containing 10 spores/ml 20-24 hours prior to treatment with the test compound.
  • the inoculated plants are kept overnight in high humidity and then allowed to dry before spraying with the test compound at a dosage of 1000 ppm using an automated sprayline as described under (a) .
  • After treatment the plants are kept in a rice compartment at 25-30 C and high humidity. Assessments are made 4-5 days after treatment and are based on the density of necrotie lesions per leaf when compared with control plants.
  • test measures the in vitro activity of compounds against the fungus causing wheat eyespot.
  • the test compound is dissolved or suspended in acetone and is added to molten half strength Potato Dextrose Agar to give a final concentration of lOOppm compound and
  • Rhizoctonia solani Activity against Rhizoctonia in-vitro
  • R. solani that causes stem and root rots.
  • the test compound in acetone is added into 4 ml aliquots of half strength Potato Dextrose Broth dispensed in 25-compartment petri dishes to give final concentrations of 100 ppm.
  • the fungal inoculum consists of mycelial fragments of R. solani growth in half strength PDB in

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Procédé de lutte contre les champignons à l'aide d'un dérivé de pipéridine de la formule générale (I), ou d'un sel d'addition d'acide de celle-ci. Dans ladite formule, R1 représente un groupe aryle éventuellement substitué par un ou plusieurs substituants; R2 représente un atome d'hydrogène ou un groupe alkyle ou phényle; R3 représente un atome d'hydrogène ou un groupe alkyle ou phényle; R4 représente un groupe alkyle, alcényle, alcynyle, cycloalkyle, aryle ou hétérocyclyle éventuellement substitué; m est un nombre entier compris entre 0 et 3; et n est un nombre entier compris entre 0 et 2. Certains des dérivés de pipéridine sont nouveaux, et l'on a également prévu la préparation de ces dérivés de pipéridine, des compositions contenant ces composés, et leur utilisation comme fongicides destinés à la lutte contre les champignons phytopathogènes.
PCT/EP1993/001777 1992-07-08 1993-07-06 Derives de piperidine Ceased WO1994001403A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU45660/93A AU4566093A (en) 1992-07-08 1993-07-06 Piperidine derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP92111568 1992-07-08
EP92111568.9 1992-07-08

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WO1994001403A1 true WO1994001403A1 (fr) 1994-01-20

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AU (1) AU4566093A (fr)
WO (1) WO1994001403A1 (fr)
ZA (1) ZA934874B (fr)

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CN1331855C (zh) * 2005-11-03 2007-08-15 上海人类基因组研究中心 一种抗真菌化合物在制药中的应用

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CN1085384A (zh) 1994-04-20
AU4566093A (en) 1994-01-31

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