EP0000508B1 - Phenylacetate von 2-Oxy-Pyridyl, Verfahren zu deren Herstellung und deren Verwendung als Schädlingsbekämpfungsmittel - Google Patents

Phenylacetate von 2-Oxy-Pyridyl, Verfahren zu deren Herstellung und deren Verwendung als Schädlingsbekämpfungsmittel Download PDF

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Publication number
EP0000508B1
EP0000508B1 EP78100376A EP78100376A EP0000508B1 EP 0000508 B1 EP0000508 B1 EP 0000508B1 EP 78100376 A EP78100376 A EP 78100376A EP 78100376 A EP78100376 A EP 78100376A EP 0000508 B1 EP0000508 B1 EP 0000508B1
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EP
European Patent Office
Prior art keywords
formula
compound
compound according
compounds
larvae
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.)
Expired
Application number
EP78100376A
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German (de)
English (en)
French (fr)
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EP0000508A1 (de
Inventor
Odd Dr. Kristiansen
Peter Dr. Ackermann
Jozef Dr. Drabek
Saleem Dr. Farooq
Laurenz Dr. Gsell
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0000508A1 publication Critical patent/EP0000508A1/de
Application granted granted Critical
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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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives 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
    • 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

Definitions

  • the present invention relates to phenylacetates of 2-oxy-pyridyl and their salts with inorganic and organic acids, processes for their preparation and their use in pest control.
  • the phenylacetates of the formula I according to the invention differ from the known compounds in that the phenyl part of the phenoxy radical is replaced by a pyridyl radical and, on the other hand, are capable of salt formation because of the pyridyloxy radical.
  • the phenylacetates have the formula wherein R 1 is hydrogen, cyano, ethynyl or methyl and R 2 and R 3 are each hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
  • Inorganic salts such as HCl, H 2 O 4 ' HBr and H 3 P0 4 are used for salt formation, and organic and organic acids include saturated and unsaturated mono-, di- and tricarboxylic acids such as formic acid, acetic acid, oxalic acid, phthalic acid, succinic acid and citric acid into consideration.
  • Halogen at R 2 and R 3 is fluorine, chlorine, bromine and iodine, but especially chlorine.
  • alkyl or alkoxy groups that are suitable for R 2 and R 3 can be straight-chain or branched. Examples of such groups include: methyl, methoxy, ethyl, ethoxy, propyl, propoxy, isopropyl, isopropoxy, n-butyl, n-butoxy-, i-, sec-, tert-butyl.
  • R 1 is cyano and R 2 and R 3 are each hydrogen or chlorine.
  • R 1 , R 2 and R 3 have the meaning given for the formula I.
  • X represents a halogen atom, in particular chlorine or bromine
  • R represents C 1 -C 4 alkyl, in particular methyl or ethyl.
  • Suitable acid-binding agents for processes 1 and 2 are, in particular, tertiary amines, such as trialkylamine and pyridine, also hydroxides, oxides, carbonates and bicarbonates of alkali and alkaline earth metals and alkali metal alcoholates such as, for example, potassium t-butoxide and sodium methylate.
  • Dicyclohexylcarbodiimide for example, can be used as the water-binding agent for process 3.
  • Processes 1 to 4 are carried out at a reaction temperature between -10 and 120 ° C, usually between 20 and 80 ° C at normal or elevated pressure and preferably in an inert solvent or diluent.
  • Suitable solvents or diluents are, for example, ethers and ethereal compounds such as diethyl ether, dipropyl ether, dioxane, dimethoxyethane and tetrahydrofuran; Amides such as N, N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, especially benzene, toluene, xylene, chloroform and chlorobenzene; Nitriles such as acetonitrile; Dimethyl sulfoxide and ketones such as acetone and methyl ethyl ketone.
  • the compounds of formula 1 are present as a mixture of different optically active isomers if optically active starting materials were not used uniformly in the preparation.
  • the various isomer mixtures can be separated into the individual isomers by known methods.
  • the compound of the formula I is understood to mean both the individual isomers and their mixtures.
  • the compounds of the formula are suitable for controlling various types of animal and vegetable pests.
  • the compounds of the formula I are suitable for controlling insects, phytopathogenic mites and ticks, e.g. the orders Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Acarina, Thysanoptera, Orthoptera, Anoplura, Siphonoptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera.
  • Compounds of the formula I are particularly suitable for combating plant-damaging insects, in particular plant-damaging insects, in ornamental and useful plants, in particular in cotton crops (e.g. against Spodoptera littoralis and Heliothis virescens) and vegetable crops (e.g. against Leptinotarsa decemlineata and Myzus persicae).
  • Active ingredients of formula I also have a very beneficial effect against flies, such as Musca domestica and mosquito larvae.
  • acaricidal or insecticidal effect can be significantly broadened by adding other insecticides and / or acaricides and adapted to the given circumstances.
  • Suitable additives are e.g. org. Phosphorus compounds; Nitrophenols and their derivatives; Formamidines: ureas; other pyrethrin-like compounds as well as carbamates and chlorinated hydrocarbons.
  • connections include Piperonyl butoxide, propynyl ether, propynyl oximes, propynyl carbamates and propynyl phosphonates, 2- (3,4-methylenedioxyphenoxy) -3,6,9-trioxaundecane (Sesamex or Sesoxane), S, S, S-tributylphosphorotrithioate, 1,2-methylenedioxy-4- (2- (octylsulfonyl) propyl) benzene.
  • Suitable additives can be solid or liquid and correspond to the substances commonly used in formulation technology, e.g. natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.
  • Aqueous active ingredient emulsion were flanzen cotton p with a 0.05% (obtained from a 10% emulsifiable concentrate) sprayed.
  • the cotton plants were each populated with Spodoptera littoralis and Heliothis virescens larvae L 3 .
  • the test was carried out at 24 ° C and 60% relative humidity.
  • Phaseolus vulgaris plants were covered with an infested leaf piece from a mass cultivation of Tetranychus urticae 12 hours before the test for acaricidal activity.
  • the overflowing movable stages were sprayed with the emulsified test preparations from a chromatography atomizer in such a way that the spray liquor did not run off.
  • larvae, adults and eggs under the binocular were evaluated for living and dead individuals and the result expressed as a percentage.
  • the treated plants were in greenhouse cabins at 25 ° C.

Landscapes

  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100376A 1977-07-20 1978-07-12 Phenylacetate von 2-Oxy-Pyridyl, Verfahren zu deren Herstellung und deren Verwendung als Schädlingsbekämpfungsmittel Expired EP0000508B1 (de)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH8999/77 1977-07-20
CH899977 1977-07-20
CH15003/77 1977-12-07
CH1500377 1977-12-07
CH5777/78 1978-05-26
CH577778 1978-05-26

Publications (2)

Publication Number Publication Date
EP0000508A1 EP0000508A1 (de) 1979-02-07
EP0000508B1 true EP0000508B1 (de) 1981-09-02

Family

ID=27175333

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100376A Expired EP0000508B1 (de) 1977-07-20 1978-07-12 Phenylacetate von 2-Oxy-Pyridyl, Verfahren zu deren Herstellung und deren Verwendung als Schädlingsbekämpfungsmittel

Country Status (13)

Country Link
US (1) US4172135A (da)
EP (1) EP0000508B1 (da)
JP (1) JPS5422374A (da)
AU (1) AU3817478A (da)
BR (1) BR7804655A (da)
CA (1) CA1095052A (da)
DE (1) DE2861000D1 (da)
EG (1) EG13419A (da)
ES (1) ES471849A1 (da)
GR (1) GR72142B (da)
IL (1) IL55162A (da)
IT (1) IT7825893A0 (da)
NZ (1) NZ187885A (da)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3005201A1 (de) * 1979-03-02 1980-09-11 Zoecon Corp Neue ester und thiolester von n-phenylsubstituierten valinderivaten
US4247701A (en) * 1979-09-24 1981-01-27 Zoecon Corporation Certain pesticidal substituted amino lower-alkanoates or lower-alkano-thioates containing pyridyl in the ester portion
US4248875A (en) * 1979-08-31 1981-02-03 Zoecon Corporation Pyridyl esters and thiolesters of α-substituted unsaturated acids
US4269981A (en) * 1979-09-24 1981-05-26 Zoecon Corporation Certain pyridylmethyl esters of formamido-lower-alkanoates and derivatives thereof
US4301156A (en) * 1979-10-01 1981-11-17 The Dow Chemical Company Insecticidal synergistic mixtures of O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) phosphorothioate and 4-chloro-α-(1-methylethyl)benzeneacetic acid:cyano (6-phenoxy-2-pyridinyl)methyl ester
JPS56147770A (en) * 1980-04-15 1981-11-16 Sumitomo Chem Co Ltd Novel carboxylic ester, its preparation and insecticide and acaricide containing the same as active constituent
US4285954A (en) * 1980-11-19 1981-08-25 Zoecon Corporation Pesticidal S-pyridyl thioesters of phenylbutanoic acids and derivatives thereof
US4798839A (en) * 1982-03-31 1989-01-17 Rhone Poulenc Nederlands B.V. Synergistic insecticidal compositions
DE3476878D1 (en) * 1984-01-12 1989-04-06 Ciba Geigy Ag Alpha-methyl-(6-phenoxy)-2-picolyl ester of cyclopropanecarboxylic acid
IL74868A0 (en) * 1984-04-13 1985-07-31 Fmc Corp Fluoropyridinylmethyl cyclopropanecarboxylate insecticides and intermediates
EP0206772A3 (en) * 1985-06-20 1988-05-11 E.I. Du Pont De Nemours And Company Herbicidal aryloxybenzeneacetic acid derivatives
WO2004087667A1 (en) * 2003-03-31 2004-10-14 Council Of Scientific And Industrial Research Ester derivatives of (pyridinyloxy-phenyl)-methanol and process of preparation thereof
KR101052620B1 (ko) * 2008-08-28 2011-07-29 한국과학기술연구원 신규 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 ｔ-형 칼슘 이온 채널의 활성에 의해 유발되는 질환의 예방 또는 치료용 조성물

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4058622A (en) * 1972-07-11 1977-11-15 Sumitomo Chemical Company, Limited Substituted phenyl acetate, insecticidal composition and method of use
EG11383A (en) * 1972-07-11 1979-03-31 Sumitomo Chemical Co Novel composition for controlling nixious insects and process for preparing thereof
US4039680A (en) * 1972-07-11 1977-08-02 Sumitomo Chemical Company, Limited Insecticidal substituted acetate compounds
US4031233A (en) * 1976-02-09 1977-06-21 Sandoz, Inc. Phenoxyphenyl imidazolyl methanols and ketone derivatives thereof

Also Published As

Publication number Publication date
CA1095052A (en) 1981-02-03
BR7804655A (pt) 1979-03-20
DE2861000D1 (en) 1981-11-26
EP0000508A1 (de) 1979-02-07
IL55162A0 (en) 1978-09-29
NZ187885A (en) 1981-05-29
EG13419A (en) 1981-06-30
ES471849A1 (es) 1979-02-01
GR72142B (da) 1983-09-20
AU3817478A (en) 1980-01-24
IT7825893A0 (it) 1978-07-19
JPS5422374A (en) 1979-02-20
US4172135A (en) 1979-10-23
IL55162A (en) 1981-07-31

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