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)

Applications Claiming Priority (6)

Publications (2)

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ID=27175333

Family Applications (1)

Country Status (13)

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Family Cites Families (4)

• 1978
  • 1978-07-12 DE DE7878100376T patent/DE2861000D1/de not_active Expired
  • 1978-07-12 EP EP78100376A patent/EP0000508B1/de not_active Expired
  • 1978-07-17 US US05/925,342 patent/US4172135A/en not_active Expired - Lifetime
  • 1978-07-18 NZ NZ187885A patent/NZ187885A/xx unknown
  • 1978-07-18 CA CA307,598A patent/CA1095052A/en not_active Expired
  • 1978-07-18 IL IL7855162A patent/IL55162A/xx unknown
  • 1978-07-18 EG EG451/78A patent/EG13419A/xx active
  • 1978-07-19 GR GR56818A patent/GR72142B/el unknown
  • 1978-07-19 ES ES78471849A patent/ES471849A1/es not_active Expired
  • 1978-07-19 IT IT7825893A patent/IT7825893A0/it unknown
  • 1978-07-19 BR BR7804655A patent/BR7804655A/pt unknown
  • 1978-07-19 AU AU38174/78A patent/AU3817478A/en active Pending
  • 1978-07-20 JP JP8893378A patent/JPS5422374A/ja active Pending

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