EP0699183A1 - Esters de l'acide 3-methoxy-2-phenylacrylique utilises comme agents antiparasitaires, notamment comme fongicides - Google Patents

Esters de l'acide 3-methoxy-2-phenylacrylique utilises comme agents antiparasitaires, notamment comme fongicides

Info

Publication number
EP0699183A1
EP0699183A1 EP94916931A EP94916931A EP0699183A1 EP 0699183 A1 EP0699183 A1 EP 0699183A1 EP 94916931 A EP94916931 A EP 94916931A EP 94916931 A EP94916931 A EP 94916931A EP 0699183 A1 EP0699183 A1 EP 0699183A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
chain
straight
branched
phenyl
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Withdrawn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
EP94916931A
Other languages
German (de)
English (en)
Inventor
Herbert Gayer
Peter Gerdes
Heinz-Wilhelm Dehne
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP0699183A1 publication Critical patent/EP0699183A1/fr
Withdrawn legal-status Critical Current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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/38—Amides of thiocarboxylic acids
    • C07C327/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C327/52—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/38—Amides of thiocarboxylic acids
    • C07C327/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C327/54—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the invention relates to new 3-methoxy-2-phenyl-acrylic acid esters, a process for their preparation and their use as pesticides.
  • R stands for optionally substituted alkyl, cycloalkyl or aryl and n stands for a number 0 or 1,
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure isomers and the isomer mixtures
  • the 3-methoxy-2-phenyl-acrylic acid esters of the formula (I) according to the invention show a considerably better activity against microorganisms which damage plants than, for example, 3-methoxy-2- (2-benzoyloxyphenyl) acrylic acid methyl ester, which is a constitutionally similar, known active ingredient same direction of action - _>
  • the 3-_vlethoxy-2-phenyl-acrylic acid esters according to the invention are generally defined by the formula (I).
  • R preferably represents straight-chain or branched alkyl having 1 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms or in each case optionally mono- to pentasubstituted by identical or different substituents
  • Aralkyl or aryl each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part, where the aryl part can in each case be substituted by
  • Carbon atoms in the individual alkyl or alkoxy parts each optionally one to five times, the same or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, each with two bonds alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, 3 to 7-membered heterocyclyl with 2 to 6 carbon atoms and 1 to 3 identical or different heteroatoms - especially nitrogen, Oxygen and / or sulfur, and in each case optionally in the phenyl part from one to five times, identical or different by halogen and / or straight-chain or branched with 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different
  • n also preferably represents a number 0 or 1.
  • R particularly preferably stands for straight-chain or branched alkyl having 1 to 6 carbon atoms, for cycloalkyl with 3 to 7 carbon atoms or for in each case optionally one to five times, equally or differently substituted aralkyl or aryl each having 6 or 10 carbon atoms in the aryl part and optionally 1 up to 4 carbon atoms in the straight-chain or branched alkyl part, where the aryl part can in each case be substituted by
  • Dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl or alkoxy parts, each optionally one to five times, the same or different, by halogen and / or straight 3 -
  • chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, substituted and in each case doubly linked .alkylene or dioxyalkylene, each having 1 to 4 carbon atoms, cycloalkyl having 3 up to 6 carbon atoms, 5- to 7-membered, saturated
  • n also particularly preferably represents a number 0 or 1.
  • R very particularly preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl or phenyl, naphthyl, benzyl or naphthylmethyl which is monosubstituted to triple, identically or differently, where appropriate, the aryl part in each case being substituted can by
  • n also very particularly preferably represents the number 0 or 1.
  • reaction sequence of the process according to the invention can be represented by the following formula *
  • Formula (III) provides a general definition of the N-acyl isothiocyanates which are furthermore required as starting materials for carrying out the process according to the invention.
  • R and n preferably represent those radicals and indices which have already been mentioned as preferred for this substituent and this index in connection with the description of the compounds of the formula (I) according to the invention.
  • N-acyl isothiocyanates of the formula (III) are generally known compounds of organic chemistry (cf. Houben-Weyl "Methods of Organic Chemistry", Vol.9, p.878, Thieme Verlag, Stuttgart; J. Am. Chem. Soc. 56, 719, 1408 [1934]; and Organic Syntheses 28, 89 [1948]).
  • Inert organic solvents are suitable as diluents for carrying out the process according to the invention.
  • Aliphatic are preferably usable.
  • Suitable acid binders for carrying out the process according to the invention are all customary inorganic or organic bases.
  • Alkaline earth or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates or ammonium compounds, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide are preferably used .
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -30 ° C and + 100 ° C, preferably at temperatures between -20 ° C and + 60 ° C.
  • the process according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • methyl 2- (2-hydroxyphenyl) -3-methoxy-acrylic acid of the formula (II) is generally employed per mole of 1.0 to 3.0 moles, preferably 1.0 to 1.5 moles of N-acyl isothiocyanate of the formula (III) and optionally 0.01 to 1.0 mol, preferably 0.1 to 0.5 mol of acid binder.
  • the reaction is carried out, worked up and isolated by known processes (cf. also the preparation examples).
  • the end products of the formula (I) are purified using customary methods, for example by column chromatography or by recrystallization.
  • the characterization is carried out with the aid of the melting point or, in the case of non-crystallizing compounds, with the aid of the refractive index or proton nuclear magnetic resonance spectroscopy (-H-NMR).
  • the active compounds according to the invention have a strong action against pests and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Plasmopara species such as, for example, Plasmopara viticola
  • Peronospora species such as, for example, Peronospora pisi or Peronospora brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechs ⁇ lera, synonym: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae
  • Pseudocercosporella species such as, for example, Pseudocercosporellä herpotrichoides.
  • the active compounds according to the invention can be particularly successful in combating diseases in fruit and vegetable cultivation, such as, for example, against the pathogen of apple scab (Venturia inaequalis) or for combating cereal diseases, for example in relation to the pathogen of powdery mildew (Erysiphe graminis) ) or against the pathogen causing brown furs in wheat (Septoria nodorum) or against the pathogen causing barley net blotch (Pyrenophora teres) or for combating rice diseases, such as are used against the pathogen of the rice stain disease (Py ⁇ cula ⁇ a oryzae)
  • the active compounds according to the invention have good in vitro activity
  • the active compounds according to the invention also have a leaf-insecticidal action
  • the active compounds can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV cold and warm fog formulations
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants, and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants, and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • Liquid solvents are essentially: flavors such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes.
  • Chlorethylene or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, as well as water
  • Liquefied gaseous extenders or carrier materials mean those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide, and solid carrier materials are possible: for example natural rock powder, such as Kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and silicates; Solid
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0, 1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used as such or in their formulations, preferably in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides. Thanks to this mixture, the spectrum of activity is broadened or the development of resistance is prevented. In many cases there are synergistic effects.
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproothat, Fufionfonofin, Phufen, Fufionfonofin, fufion, fufon, phufen, fufon, phufen, fufion, fufon, fufon, phufon, phufen, fufon, phufen, fufon, phufen, fufon, phufen, fufon, phufen, fufon, phufen, fufon, phuf
  • Methamidophos Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M Primiphos A, Profenofos, Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos, Prothoat, Py- metrozin, Pyrachlophos, Pyraclofos, Pyraclophos, Pyradaphrinum, Pyr- methrhrentum, Pyreshraphenhion, Pyreshraphenin Pyrimidifen, pyriproxifen,
  • Tebufenozid Tebufenpyrad
  • Tebupirimphos Teflubenzuron
  • Tefluthrin Temephos
  • the active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to prepare the active ingredient or the active ingredient itself in the Inject soil.
  • the seeds of the plants can also be treated.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • a part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 20 ° C. and a relative atmospheric humidity of approx. 70%.
  • Evaluation is carried out 12 days after the inoculation.
  • the compounds according to the invention disclosed in Examples 1, 2, 3, 4, 5, 6, 7, 8, 10 and 11 show an efficiency of 50% to 100% while at a concentration of 10 ppm in the spray liquid the comparison substance (A) has an efficiency of less than 30%.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention a pour objet de nouveaux esters de l'acide 3-méthoxy-2-phénylacrylique de formule (I), dans laquelle R désigne un alkyle, cycloalkyle ou aryle, chacun de ces restes étant éventuellement substitué, et n est égal à 0 ou à 1, ainsi qu'un procédé de fabrication de ces nouveaux produits et leur utilisation comme agents antiparasitaires.
EP94916931A 1993-05-17 1994-05-04 Esters de l'acide 3-methoxy-2-phenylacrylique utilises comme agents antiparasitaires, notamment comme fongicides Withdrawn EP0699183A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4316431 1993-05-17
DE4316431A DE4316431A1 (de) 1993-05-17 1993-05-17 3-Methoxy-2-phenyl-acrylsäureester
PCT/EP1994/001417 WO1994026705A1 (fr) 1993-05-17 1994-05-04 Esters de l'acide 3-methoxy-2-phenylacrylique utilises comme agents antiparasitaires, notamment comme fongicides

Publications (1)

Publication Number Publication Date
EP0699183A1 true EP0699183A1 (fr) 1996-03-06

Family

ID=6488268

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94916931A Withdrawn EP0699183A1 (fr) 1993-05-17 1994-05-04 Esters de l'acide 3-methoxy-2-phenylacrylique utilises comme agents antiparasitaires, notamment comme fongicides

Country Status (7)

Country Link
US (1) US5728729A (fr)
EP (1) EP0699183A1 (fr)
JP (1) JPH08510217A (fr)
CN (1) CN1123543A (fr)
AU (1) AU6842794A (fr)
DE (1) DE4316431A1 (fr)
WO (1) WO1994026705A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6066754A (en) * 1999-06-10 2000-05-23 Bayer Corporation Process for manufacturing N-alkoxy(or aryloxy)carbonyl isothiocyanate derivatives using N,N-dialkylarylamine as catalyst

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9218541D0 (en) * 1991-09-30 1992-10-14 Ici Plc Fungicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9426705A1 *

Also Published As

Publication number Publication date
JPH08510217A (ja) 1996-10-29
AU6842794A (en) 1994-12-12
CN1123543A (zh) 1996-05-29
WO1994026705A1 (fr) 1994-11-24
DE4316431A1 (de) 1994-11-24
US5728729A (en) 1998-03-17

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