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WO1996003879A1 - Insecticides - Google Patents

Insecticides Download PDF

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Publication number
WO1996003879A1
WO1996003879A1 PCT/EP1995/002798 EP9502798W WO9603879A1 WO 1996003879 A1 WO1996003879 A1 WO 1996003879A1 EP 9502798 W EP9502798 W EP 9502798W WO 9603879 A1 WO9603879 A1 WO 9603879A1
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WO
WIPO (PCT)
Prior art keywords
spp
alkyl
radical
group
compounds
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/EP1995/002798
Other languages
German (de)
English (en)
Inventor
Christoph Erdelen
Wolfgang Krämer
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
Priority to AU31126/95A priority Critical patent/AU3112695A/en
Priority to JP50612896A priority patent/JPH10503500A/ja
Priority to EP95926912A priority patent/EP0804080A1/fr
Publication of WO1996003879A1 publication Critical patent/WO1996003879A1/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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Definitions

  • the present invention relates to insecticidal compositions based on chloromicinyl insecticides and synergists for insecticides.
  • Chloronicotinyl insecticides are known e.g. from EP-OS 192 060.
  • Synergists for insecticides are inhibitors for oxidases or cytochrome P 450 or increase the penetrability of cell membranes. You are known e.g. B. from chemistry of pesticides and pesticides Bnd. 7 K.
  • the present invention relates to mixtures of chloromotinyl insecticides of the formula (I)
  • A represents optionally substituted alkyl or a bifunctional group which is linked to the radical Z;
  • E represents an electron withdrawing group
  • radical A or radical X represents a bifunctional group which is linked to radical A or radical X
  • R represents hydrogen or alkyl
  • A stands for optionally substituted C -alkyl, or for a bifunctional group.
  • Optionally substituted alkylene with 1-4, in particular 1-2, carbon atoms may be mentioned, it being possible for the alkylene groups to be interrupted by heteroatoms from the series N, O, S
  • a and Z together with the atoms to which they are attached, can form a saturated or unsaturated heterocyclic ring.
  • the heterocyclic ring can contain a further 1 or 2 identical or different hetero atoms and / or hetero groups.
  • Preferred heteroatoms are wise oxygen, sulfur or nitrogen and as hetero groups N-alkyl, alkyl of the N-alkyl group preferably containing 1 to 4, in particular 1 or 2 carbon atoms.
  • alkyl methyl, ethyl, n- and i-propyl and n-, i- and t-butyl may be mentioned.
  • the heterocych ring contains 5 to 7, preferably 5 or 6 ring members.
  • heterocyclic ring examples include pyrrolidine, piperidine, piperazine, hexamethyl enimine, hexahydro-l, 3,5-triazine, morpholine, which may optionally be substituted by methyl.
  • E stands for an electron-withdrawing radical, with particular mention being made of NO 2 or CN.
  • Z represents optionally substituted radicals C M -alkyl, -OR, -SR, -NRR, where R preferably represents hydrogen or C M -alkyl,
  • the heterocychic ring can contain a further 1 or 2 identical or different heteroatoms and / or hetero groups.
  • the hetero atoms are preferably oxygen, sulfur or nitrogen and the hetero groups are N-alkyl, the alkyl or N-alkyl group preferably containing 1 to 4, in particular 1 or 2, carbon atoms. Alkyl, methyl, ethyl, n- and i-propyl and n-, i- and t-butyl may be mentioned.
  • the heterocych ring contains 5 to 7, preferably 5 or 6 ring members.
  • heterocyclic ring examples include pyrrolidine, piperidine,
  • Preferred synergists are:
  • R, R 1 and R 2 may be the same or different and represent hydrogen or alkyl.
  • R represents hydrogen, C alkyl, C ⁇ alkenyl, halogen or nitro
  • R 1 represents C j _ 4 - alkyl or hydrogen
  • R 2 stands for aralkyl, C M alkyl, C ⁇ alkenyl, C 3.6 cycloalkyl or for hydrogen and also
  • Alk is C j _ 4 alkyl
  • Aryl represents phenyl
  • n stands for the numbers 0 or 1
  • X and Y are independently O or S.
  • R represents optionally substituted alkyl, aryl or aralkyl.
  • Alk represents C alkyl
  • R represents alkenyl or alkynyl
  • R 1 , R 2 , R 3 and R 4 which may be the same or different, for
  • Alk stands for C - alkyl
  • the active substance mixtures can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations 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 mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations 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 mist formulations.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or
  • organic solvents can also be used as Auxiliary solvents can be used.
  • 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 and their ethers and esters ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl formamide and dimethyl sulfoxide, and water;
  • liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers are possible: e.g.
  • natural rock meals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for
  • Granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifiers and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also 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, for example 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 compound mixture, preferably between 0.5 and 90%.
  • the active substance mixtures are suitable, with good plant tolerance and favorable warm-blood toxicity, for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Diplopoda e.g. Blaniulus guttulatus.
  • Chilopoda e.g. Geophilus carpophagus, Scutigera spec.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus ar ⁇ ndinis,
  • Siphonaptera for example Xenopsylla cheopis, Ceratophyllus spp.
  • Arachnida for example Scorpio maurus and Latrodectus mactans.
  • Acarina for example Acarus siro, Argas spp., O ithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant-parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidoms spp., Xiphinema spp., Trichodorus spp.
  • the active compound mixtures according to the invention 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, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds such as insecticides, attractants, sterilants, 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 substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms can be from 0.0000001 to 95% by weight of active ingredient, 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
  • 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 being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist.
  • the plants are populated with horseradish leaf beetle larvae (Phaedon cochleariae). After each 7 days, the death rate is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae 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 active ingredient preparation of the desired concentration and with caterpillars of the cabbage cockroach
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Solvent 7 parts by weight of dimethylformamide 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 being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the owl butterfly (Spodoptera frugiperda) 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.
  • Solvent 7 parts by weight of dimethylformamide 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 (Oryzae sativa) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the green leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
  • the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • Solvent 3 parts by weight of dimethylformamide 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), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

Landscapes

  • 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)

Abstract

L'invention concerne des mélanges d'insecticides au chloronicotinyle ayant la formule (I), dans laquelle les substituants X, A, Z et E ont la notation donnée dans la description, avec des synergistes sélectionnés dans le groupe constitué a) des composés d'isochromane ou de benzodioxol, b) des dérivés de propargyle, c) des esters d'acide phosphonique d'alcoyle, d) des esters d'acide phosphorique, e) des dérivés d'azol, f) des esters pinoniques, g) des formamides, h) des amides et esters d'acide carboxylique C12-21, i) des diarylamines, k) des imides cycliques et l) de l'huile de neem.
PCT/EP1995/002798 1994-07-29 1995-07-17 Insecticides Ceased WO1996003879A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU31126/95A AU3112695A (en) 1994-07-29 1995-07-17 Insecticides
JP50612896A JPH10503500A (ja) 1994-07-29 1995-07-17 殺虫剤
EP95926912A EP0804080A1 (fr) 1994-07-29 1995-07-17 Insecticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944426942 DE4426942A1 (de) 1994-07-29 1994-07-29 Insektizide Mittel
DEP4426942.0 1994-07-29

Publications (1)

Publication Number Publication Date
WO1996003879A1 true WO1996003879A1 (fr) 1996-02-15

Family

ID=6524469

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/002798 Ceased WO1996003879A1 (fr) 1994-07-29 1995-07-17 Insecticides

Country Status (5)

Country Link
EP (1) EP0804080A1 (fr)
JP (1) JPH10503500A (fr)
AU (1) AU3112695A (fr)
DE (1) DE4426942A1 (fr)
WO (1) WO1996003879A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5952358A (en) * 1995-01-30 1999-09-14 Rhone-Poulenc Agrochimie Insecticidal combinations including an insecticide from the chloronicotinyl family and an insecticide having a pyrazole, pyrrole or phenylimidazole group
WO2003099012A1 (fr) * 2002-05-23 2003-12-04 Syngenta Limited Phosphonates et leurs derives utilises comme agents d'activation d'insecticides
WO2010061934A1 (fr) * 2008-11-25 2010-06-03 Sumitomo Chemical Company, Limited Composition destinée à la lutte contre les parasites et procédé de lutte contre les parasites

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10059606A1 (de) 2000-12-01 2002-06-06 Bayer Ag Wirkstoffkombinationen
DE102004032418A1 (de) * 2004-04-07 2005-10-27 Bayer Cropscience Ag Wirkstoffkombinationen mit insektiziden Eigenschaften

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4731385A (en) * 1985-10-26 1988-03-15 Nihon Tokushu Noyaku Seizo K.K. Insecticidal and fungicidal composition for agricultural and horticultural use
WO1993003617A1 (fr) * 1991-08-27 1993-03-04 Nippon Soda Co., Ltd. Composition insecticide
EP0617890A1 (fr) * 1993-03-18 1994-10-05 Nihon Bayer Agrochem K.K. Compositions insecticides synergiques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4731385A (en) * 1985-10-26 1988-03-15 Nihon Tokushu Noyaku Seizo K.K. Insecticidal and fungicidal composition for agricultural and horticultural use
WO1993003617A1 (fr) * 1991-08-27 1993-03-04 Nippon Soda Co., Ltd. Composition insecticide
EP0617890A1 (fr) * 1993-03-18 1994-10-05 Nihon Bayer Agrochem K.K. Compositions insecticides synergiques

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 119, no. 15, 1993, Columbus, Ohio, US; abstract no. 153987c, M.Y. LIU ET AL: "Relevance of (3H)imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethylene- and 2-nitroimino-imidazolines." *
K. NAUMANN: "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel. Band 7", 1981, SPRINGER VERLAG, BERLIN *
PESTIC. BIOCHEM. PHYSIOL., vol. 46, no. 3, 1993, pages 200 - 206 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5952358A (en) * 1995-01-30 1999-09-14 Rhone-Poulenc Agrochimie Insecticidal combinations including an insecticide from the chloronicotinyl family and an insecticide having a pyrazole, pyrrole or phenylimidazole group
US6077860A (en) * 1995-01-30 2000-06-20 Rhone-Poulenc Agrochimie Insecticidal combinations including an insecticide from the chloronicotinyl family and an insecticide having a pyrazole, pyrrole or phenylimidazole group
WO2003099012A1 (fr) * 2002-05-23 2003-12-04 Syngenta Limited Phosphonates et leurs derives utilises comme agents d'activation d'insecticides
US9138003B2 (en) 2002-05-23 2015-09-22 Syngenta Crop Protection Inc. Phosphonates and derivatives thereof as enhancers of the activity of insecticides
WO2010061934A1 (fr) * 2008-11-25 2010-06-03 Sumitomo Chemical Company, Limited Composition destinée à la lutte contre les parasites et procédé de lutte contre les parasites
CN102223800A (zh) * 2008-11-25 2011-10-19 住友化学株式会社 害虫防治组合物和防治害虫的方法
EP2647288A1 (fr) * 2008-11-25 2013-10-09 Sumitomo Chemical Company Limited Composition et procédé de lutte contre les nuisibles
AU2009320713B2 (en) * 2008-11-25 2014-09-25 Sumitomo Chemical Company, Limited Pest controlling composition and method of controlling pest
US8940777B2 (en) 2008-11-25 2015-01-27 Sumitomo Chemical Company, Limited Pest controlling composition and method of controlling pest
CN102223800B (zh) * 2008-11-25 2015-03-25 住友化学株式会社 害虫防治组合物和防治害虫的方法

Also Published As

Publication number Publication date
JPH10503500A (ja) 1998-03-31
EP0804080A1 (fr) 1997-11-05
AU3112695A (en) 1996-03-04
DE4426942A1 (de) 1996-02-01

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