EP0595845A1 - Produits phytosanitaires insecticides et acaricides renfermant des derives du 1,2,4-oxadiazole substitues - Google Patents

Produits phytosanitaires insecticides et acaricides renfermant des derives du 1,2,4-oxadiazole substitues

Info

Publication number
EP0595845A1
EP0595845A1 EP92914318A EP92914318A EP0595845A1 EP 0595845 A1 EP0595845 A1 EP 0595845A1 EP 92914318 A EP92914318 A EP 92914318A EP 92914318 A EP92914318 A EP 92914318A EP 0595845 A1 EP0595845 A1 EP 0595845A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
halogen
substituted
alkoxy
hydrogen
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Withdrawn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
EP92914318A
Other languages
German (de)
English (en)
Inventor
Peter Jeschke
Werner Lindner
Ulrike Wachendorff-Neumann
Christoph Erdelen
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 EP0595845A1 publication Critical patent/EP0595845A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to the use of partially known 1,2,4-oxadiazole derivatives as insecticides and acaricides in crop protection,
  • R 1 represents hydrogen or represents optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl,
  • R 2 for hydrogen, nitro, cyano, carboxy, carbamoyl
  • R 3 represents hydrogen, nitro, cyano, carboxy, carbamoyl, halogen or represents optionally substituted alkyl, alkoxy or alkylthio
  • R 4 for hydrogen, hydroxy, mercapto, amino, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkyl sulfonyl, alkylamino, dialkylamino, alkyl carbonylamino, alkyl carbonyl, alkyl carbonyloxy, alkoxycarbonyl , Alkoxyalkyl, hydroxyalkoxy, alkoxyalkoxy, for aryl, aryloxy, aralkyloxy, arylthio, aralkylthio, arylsulfinyl or arylsulfonyl optionally substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, or together with R 3 stands
  • Formula (I) provides a general definition of 1,2,4-oxadiazole derivatives. According to the invention, preference is given to using those compounds of the formula (I) in which rather
  • R 2 represents hydrogen, nitro, cyano, carboxy, carbamoyl, halogen or alkyl, alkoxy or alkylthio, each optionally substituted by halogen, each having 1 to 4 carbon atoms,
  • R 3 represents hydrogen, nitro, cyano, carboxy, carbamoyl, halogen or alkyl, alkoxy or alkylthio, each optionally substituted by halogen, each having 1 to 4 carbon atoms
  • R 4 for hydrogen, hydroxy, mercapto, amino, halogen, for alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkylcarbonyl, alkyl carbonyloxy, alkoxycarbonyl , Alkoxyalkyl, hydroxyalkoxy, alkoxyalkoxy each having 1 to 4 carbon atoms, each optionally by halogen, C 1 -C 4 alkyl,
  • R 1 represents hydrogen, straight-chain or branched C 1 -C 4 alkyl, which is optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, represents cyclopropyl, cyclopentyl, cyclohexyl or thienyl
  • R 2 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine or alkyl, alkoxy or alkylthio, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms
  • R 3 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine or alkyl in each case optionally substituted by fluorine and / or chlorine and having 1 to 4 carbon atoms
  • R 1 represents hydrogen, straight-chain or branched C 1 -C 4 alkyl, which is optionally substituted by fluorine, chlorine, bromine, me
  • R 4 for hydrogen, fluo, chlorine, bromine, methyl, ethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylsulfethyl, trifluoromethyl, methyldifluoromethyl, sulfonyl, methyldifluoromethyl, Methylsulfonyl, ethylsulfonyl, trifluoromethyl sulfonyl, methylamino, ethylamino, dimethylamino, acetylamino, acetyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, each representing phenyl, phenoxy or benzoxy, optionally
  • the E isomers of the compounds of the formula (I) are preferably used according to the invention.
  • the substituted 1,2,4-oxadiazole derivatives to be used according to the invention are known and / or can be prepared by processes known per se (cf. US Pat. No. 4102377. J. Chem, Soc, 1973, 2241-2249; DE patent application no. 4041474).
  • the compounds of the formula (I) are obtained if amidoximes of the formula (II)
  • R 1 has the meaning given above and R represents methyl or ethyl, optionally in the presence of a reaction auxiliary, such as, for example, boron trifluoride etherate or pyridine, and optionally in the presence of a diluent, such as chlorobenzene or chloroform, at temperatures between 10 ° C. and 180 ° C and processed using customary methods (see the manufacturing examples).
  • a reaction auxiliary such as, for example, boron trifluoride etherate or pyridine
  • a diluent such as chlorobenzene or chloroform
  • amidoximes of the formula (II) are known and / or can be prepared by processes known per se (cf. J. Chem. Soc. Perkin I 1973, 2241-2249; J. Heterocycl. Chem. 15 (1978), 1373- 1378).
  • the carboxylic acid derivatives of the formulas (III), (IV), (V) and (VI) are known organic synthetic chemicals.
  • the compounds of the formula (I) are suitable for controlling animal pests in crop cultivation, in particular insects and mites. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Diplopoda for example, Blaniulus guttulatus.
  • Thysanura e.g. Lepisma saccharina.
  • Collembola e.g. Onychiurus armatus.
  • Orthoptera e.g. Blatta Orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • From the order of the Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp ,, Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • the active ingredients can be converted into customary formulations, such as solutions, Emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, fine encapsulation in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals etc., as well as ULV cold and warm fog formulations.
  • customary formulations such as solutions, Emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, fine encapsulation in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals etc., as well as 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, If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers
  • 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 aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean 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;
  • Solid carrier materials are suitable: for example natural rock powders such as
  • emulsifiers and / or foam-generating agents are: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • Alkylaryl polyglycol ether alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose,
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, and further 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
  • Substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, steroids, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • the active compounds can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the kill is determined in%. 100 J4 means that all spider mites have been killed; 0% means that none of the spheres have been killed. In this test, for example, the following compounds of the preparation examples show very strong acaricidal activity: 1, 8, 66, 69 and 70.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbages (Brassica oleracea) are treated with the active ingredient preparation of the desired concentration.
  • One leaf of the treated plant is placed in a plastic can and is covered with larvae (L 3 ) of the horseradish beetle (Phaedon cochleariae). After 2 to 4 days, another leaf from the same plant is used for the replenishment. After the desired time, the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the preparation of the active ingredient of the desired concentration and populated with caterpillars of the cockroach (Flutella maculipennis) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
  • the kill is determined in 5. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne l'utilisation de dérivés du 1,2,4-oxadiazole partiellement connus, comme insecticides et acaricides en protection phytosanitaire. Les composés conformes à l'invention présentent la formule (I) dans laquelle R1 désigne un hydrogène ou un alkyle, cycloalkyle, aryle ou hétérocyclyle, chacun de ces groupes portant éventuellement des substituants, R2 désigne un hydrogène, nitro, cyano, carboxy, carbamoyle, un halogène, un alkyle, alkoxy ou alkylthio, chacun de ces trois derniers groupes portant éventuellement des substituants, R3 désigne un hydrogène, nitro, cyano, carboxy, carbamoyle, un halogène ou un alkyle, alkoxy ou alkylthio, chacun de ces trois derniers groupes portant éventuellement des substituants, et R4 a la signification donnée dans la description.
EP92914318A 1991-07-20 1992-07-06 Produits phytosanitaires insecticides et acaricides renfermant des derives du 1,2,4-oxadiazole substitues Withdrawn EP0595845A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4124151A DE4124151A1 (de) 1991-07-20 1991-07-20 Insektizide und akarizide pflanzenschutzmittel enthaltend substituierte 1,2,4-oxadiazolderivate
DE4124151 1991-07-20
PCT/EP1992/001525 WO1993001719A1 (fr) 1991-07-20 1992-07-06 Produits phytosanitaires insecticides et acaricides renfermant des derives du 1,2,4-oxadiazole substitues

Publications (1)

Publication Number Publication Date
EP0595845A1 true EP0595845A1 (fr) 1994-05-11

Family

ID=6436660

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92914318A Withdrawn EP0595845A1 (fr) 1991-07-20 1992-07-06 Produits phytosanitaires insecticides et acaricides renfermant des derives du 1,2,4-oxadiazole substitues

Country Status (8)

Country Link
US (1) US5428049A (fr)
EP (1) EP0595845A1 (fr)
JP (1) JPH06509104A (fr)
AU (1) AU2230092A (fr)
BR (1) BR9206292A (fr)
DE (1) DE4124151A1 (fr)
HU (1) HUT72174A (fr)
WO (1) WO1993001719A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4401107A1 (de) * 1994-01-17 1995-07-20 Bayer Ag 3-Aryl-alkenyl-1,2,4-oxadiazol-Derivate
DE19962147A1 (de) * 1999-12-22 2001-06-28 Bayer Ag Schädlingsbekämpfungsmittel / PF 1022-221
DE10039477A1 (de) * 2000-08-08 2002-02-21 Aventis Cropscience Gmbh Heterocyclylalkylazol-Derivate und ihre Verwendung als Schädlingsbekämpfungsmittel
PY1981410A (es) * 2018-10-01 2020-04-07 Pi Industries Ltd Nuevos oxadiazoles

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL291628A (fr) * 1962-04-17
GB1228142A (fr) * 1967-03-31 1971-04-15
DE2426878A1 (de) * 1974-06-04 1976-01-08 Basf Ag Verfahren zur herstellung von 1,2,4oxadiazolen
EP0036711B1 (fr) * 1980-03-22 1985-12-04 Fbc Limited Composés hétérocycliques pesticides, procédés pour leur préparation, compositions les contenant, et leur utilisation
DE3135236A1 (de) * 1981-09-05 1983-03-17 Hoechst Ag, 6000 Frankfurt Substituierte 1.2.4.-oxadiazol-3-yl-vinyl-(thio)-phosphate und -phosphonate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide mittel"
JPS63165376A (ja) * 1986-12-27 1988-07-08 Nippon Soda Co Ltd オキサ（チア）ジアゾ−ル誘導体その製造方法及び殺ダニ剤
DE4041474A1 (de) * 1990-12-22 1992-06-25 Bayer Ag Verwendung von substituierten 1,2,4-oxadiazolderivaten zur bekaempfung von endoparasiten, neue substituierte 1,2,4-oxadiazolderivate und verfahren zu ihrer herstellung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9301719A1 *

Also Published As

Publication number Publication date
BR9206292A (pt) 1994-09-27
AU2230092A (en) 1993-02-23
US5428049A (en) 1995-06-27
DE4124151A1 (de) 1993-01-21
JPH06509104A (ja) 1994-10-13
HUT72174A (en) 1996-03-28
HU9400168D0 (en) 1994-05-30
WO1993001719A1 (fr) 1993-02-04

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