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WO1997016971A1 - Insecticides - Google Patents

Insecticides Download PDF

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Publication number
WO1997016971A1
WO1997016971A1 PCT/EP1996/004574 EP9604574W WO9716971A1 WO 1997016971 A1 WO1997016971 A1 WO 1997016971A1 EP 9604574 W EP9604574 W EP 9604574W WO 9716971 A1 WO9716971 A1 WO 9716971A1
Authority
WO
WIPO (PCT)
Prior art keywords
spp
insects
urea
alkyl
antagonists
Prior art date
Application number
PCT/EP1996/004574
Other languages
German (de)
English (en)
Inventor
Wolfgang Wirth
Uwe Priesnitz
Gerhard Baron
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU72969/96A priority Critical patent/AU7296996A/en
Publication of WO1997016971A1 publication Critical patent/WO1997016971A1/fr

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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 containing agonists or antagonists of the nicotinergic acetylcholine receptors of insects, urea or its derivatives and surface-active substances
  • Agonists or antagonists of the nicotinergic acetylcholine receptors of insects are known, for example from the following publications
  • Agonists or antagonists of the nicotinergic acetylcholine receptors of insects are sometimes summarized under the term nitromethylenes and related compounds
  • R represents hydrogen, optionally substituted radicals from the group acyl, alkyl,
  • E represents an electron-withdrawing residue
  • H atom can be linked to the radical Z;
  • R N stands for a bifunctional group that is associated with the
  • Radical A or the radical X is linked.
  • R represents hydrogen and also optionally substituted radicals from the
  • Formyl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, (alkyl-) - (aryl-) - phosphoryl, which in turn can be substituted, may be mentioned as acyl radicals.
  • alkyl which may be mentioned are C ⁇ l0 -alkyl, in particular C, .4- alkyl, in particular methyl, ethyl, i-propyl, see- or t-butyl, which in turn can be substituted
  • Phenyl, naphthyl, in particular phenyl, may be mentioned as aryl
  • Phenylmethyl and phenethyl may be mentioned as aralkyl
  • Heteroaryl with up to 10 ring atoms and N, O, S in particular N as heteroatoms may be mentioned as heteroaryl.
  • Thiophenyl, furyl, thiazolyl, imidazolyl, pyridyl and benzothiazolyl may be mentioned in particular Heteroaryl alkyl which may be mentioned are heteroarylmethyl, heteroarylethyl having up to 6 ring atoms and N, O, S, in particular N, as heteroatoms
  • substituents are, preferably, alkyl with preferably 1 to 4, in particular 1 or 2, carbon atoms, such as methyl, ethyl, n- and i-propyl and n-, l- and t-butyl, alkoxy with preferably 1 to 4 , in particular 1 or 2 carbon atoms, such as methoxy, ethoxy, n- and i-propyloxy and n-, i- and t-butyloxy, alkylthio with preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methylthio, ethylthio , n- and i-propylthio and n-, i- and t-butylthio, haloalkyl preferably having 1 to 4, in particular 1 or 2, carbon atoms and preferably 1 to 5, in particular 1 to 3, halogen atoms, the halogen atoms being identical or different and as halogen atoms, preferably fluor
  • 1 to 4 carbon atoms such as methylsulfonyl and ethylsulfonyl, arylsulfonyl with preferably 6 or 10 aryl carbon atoms, such as phenylsulfonyl, and also heteroarylamino and heteroarylalkylamino such as chloropyidylamino and chloropyridylmethylamino
  • Heteroatoms from the series N, O, S can be interrupted
  • 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- contain atoms and / or hetero groups
  • the hetero atoms are preferably oxygen, sulfur or nitrogen and the hetero groups N-alkyl, alkyl of the N-alkyl group preferably containing 1 to 4, in particular 1 or 2, carbon atoms.
  • the alkyls are methyl, ethyl, n- and i- Propyl and n-, I- and t-butyl called
  • the heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members
  • heterocyclic ring examples include pyrrolidine, piperidine, piperazine, hexamethyleneimine, hexahydro-l, 3,5-t ⁇ az ⁇ n, morpholine, which may optionally be preferably substituted by methyl
  • E stands for an electron-withdrawing radical, in particular NO 7 , CN,
  • Haloalkylcarbonyl such as 1,5-halogen-C M -carbonyl, in particular COCF 3 may be mentioned
  • Z stands for optionally substituted radicals alkyl, -OR, -SR, -NRR, where R and the substituents preferably have the meaning given above
  • Z can also join the atom
  • the heterocyclic ring may contain a further 1 or 2 identical or different heteroatoms and / or hetero groups.
  • the heteroatoms are preferably oxygen, sulfur or nitrogen and as hetero groups N-alkyl, the alkyl or N-alkyl group, preferably 1 to 4, in particular 1 or 2 carbon atoms, and alkyl may be methyl, ethyl, n- and i-propyl and n-, i- and t-butyl.
  • the heterocyclic ring contains 5 to 7 , preferably 5 or 6 ring links
  • heterocyclic ring examples include pyrrolidine, piperidine, piperazine, hexamethyleneimine, morpholine and N-methylpiperazine
  • compounds of the general formulas (II) and (III) may be mentioned as very particularly preferred compounds which can be used according to the invention
  • n 1 or 2
  • Urea is particularly preferably used
  • the mixtures according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector. They are resistant to normally sensitive and resistant species and effective against all or individual stages of development
  • animal pests preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector. They are resistant to normally sensitive and resistant species and effective against all or individual stages of development
  • the pests mentioned above include
  • Isopoda for example Oniscus asellus, Armadillidium vulgare, Porecellio scaber From the order of the Diplopoda, for example, Blaniulus guttulatus
  • Thysanoptera e.g. Hercinothrips femoralis, Th ⁇ ps tabaci
  • Anthonomus pp Sitophilus spp, Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp, Trogoderma spp, Anthrenus spp, Attagenus spp, Lyctus spp, Meligethes aeneus, Ptinus holium sppno, Pt , Ag ⁇ otes spp, Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica
  • Hymenoptera From the order of the Hymenoptera, for example Diprion spp, Hoplocampa spp, Lasius spp, Monomorium pharaonis, Vespa spp ..
  • Chewing biting insects for example from the orders Coleoptera or Lepidoptera, may be mentioned
  • the respective physical and / or chemical properties of the mixtures according to the invention can be converted into customary formulations. those 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, furthermore in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and warm fog formulations
  • compositions 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 Foaming agents
  • 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 Foaming agents
  • organic solvents can also be used as auxiliary solvents.
  • Liquid solvents are essentially aromatics, such as xylene, toluene, or 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 dimethyl formamide and dimethyl sulfoxide, and also water Liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, e.g. aerosol propellant, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; solid carrier materials are possible, e.g.
  • rock powders such as kaolins , Clays, talc, chalk, quartz, attapulgite, montmo ⁇ llonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules come into question e.g.
  • emulsifiers and / or foam-generating agents are possible, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • suitable dispersants include lignin sulfite waste liquors 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, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal lphthalocyanin dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the mixtures according to the invention can also contain other active ingredients, such as
  • Insecticides attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas and others.
  • mixtures according to the invention can also be used in their commercially available
  • Formulations and in the use forms prepared from these formulations are present 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 mixtures according to the invention contain agonists and antagonists of the nicotinergic acetylcholine receptors of insects in concentrations of 0.1 to 50% by weight, preferably 0.1 to 25% by weight, very particularly preferably 0.1 to 10% by weight.
  • the mixtures according to the invention contain urea or its derivatives in concentrations of 99 to 45% by weight, preferably 95 to 35% by weight.
  • the mixtures according to the invention contain surface-active substances in concentrations of 0.1 to 10% by weight, preferably 0.2 to 5% by weight.
  • the active ingredient concentration of the agonsites or antagonists of the nicotinergic acetylcholine receptors of Insects in the use forms can be from 0.0001 to 1% by weight of active compound, preferably between 0.0016 and 0.1% by weight.
  • the application takes place in a customary manner adapted to the application forms by spraying, atomizing, dusting, spraying, pouring.
  • Active substances characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.
  • the compound with the common name imidacloprid (1- (2-chloro-5-pyridinyl-methyl) -2-nitroiminoimidazoline) is used as a representative of an agonist or antagonist of the nicotinergic acetylcholine receptors of insects.

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 insecticides renfermant des agonistes ou des antagonistes des récepteurs nicotiniques à l'acétylcholine d'insectes, ainsi que de l'urée ou des dérivés de l'urée et des substances tensio-actives.
PCT/EP1996/004574 1995-11-03 1996-10-22 Insecticides WO1997016971A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU72969/96A AU7296996A (en) 1995-11-03 1996-10-22 Insecticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19540948.5 1995-11-03
DE19540948A DE19540948A1 (de) 1995-11-03 1995-11-03 Insektizide Mittel

Publications (1)

Publication Number Publication Date
WO1997016971A1 true WO1997016971A1 (fr) 1997-05-15

Family

ID=7776506

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/004574 WO1997016971A1 (fr) 1995-11-03 1996-10-22 Insecticides

Country Status (4)

Country Link
AU (1) AU7296996A (fr)
DE (1) DE19540948A1 (fr)
WO (1) WO1997016971A1 (fr)
ZA (1) ZA969209B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005112624A3 (fr) * 2004-05-13 2006-01-05 Bayer Cropscience Ag Procede ameliorant la croissance de plantes
CN1294812C (zh) * 1998-02-23 2007-01-17 拜尔公司 抗人体寄生虫和螨虫的含水制剂
CN1328958C (zh) * 1998-02-23 2007-08-01 拜尔公司 施用于皮肤的含水杀寄生物制剂

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1205999A (en) * 1997-10-31 1999-05-24 University Of Florida Control of tephritidae fruit flies
JP4324308B2 (ja) * 2000-04-26 2009-09-02 住友化学株式会社 ハエ類の防除方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5718605A (en) * 1980-07-07 1982-01-30 Kumiai Chem Ind Co Ltd Stable insecticidal composition
DE4412833A1 (de) * 1994-04-14 1995-10-19 Bayer Ag Insektizide Düngemischungen

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5718605A (en) * 1980-07-07 1982-01-30 Kumiai Chem Ind Co Ltd Stable insecticidal composition
DE4412833A1 (de) * 1994-04-14 1995-10-19 Bayer Ag Insektizide Düngemischungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CENTRAL PATENTS INDEX, BASIC ABSTRACTS JOURNAL Section Ch Week 8210, Derwent World Patents Index; Class C02, AN 82-18651E, XP002026835 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1294812C (zh) * 1998-02-23 2007-01-17 拜尔公司 抗人体寄生虫和螨虫的含水制剂
CN1328958C (zh) * 1998-02-23 2007-08-01 拜尔公司 施用于皮肤的含水杀寄生物制剂
WO2005112624A3 (fr) * 2004-05-13 2006-01-05 Bayer Cropscience Ag Procede ameliorant la croissance de plantes

Also Published As

Publication number Publication date
DE19540948A1 (de) 1997-05-07
AU7296996A (en) 1997-05-29
ZA969209B (en) 1997-06-18

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