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WO1982003390A1 - Derives de phenoxy-phenyle-isothio-uree, produits intermediaires a base de phenoxy-phenyle-thio-uree, leur preparation et leur utilisation dans la lutte contre les insectes - Google Patents

Derives de phenoxy-phenyle-isothio-uree, produits intermediaires a base de phenoxy-phenyle-thio-uree, leur preparation et leur utilisation dans la lutte contre les insectes Download PDF

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Publication number
WO1982003390A1
WO1982003390A1 PCT/CH1981/000037 CH8100037W WO8203390A1 WO 1982003390 A1 WO1982003390 A1 WO 1982003390A1 CH 8100037 W CH8100037 W CH 8100037W WO 8203390 A1 WO8203390 A1 WO 8203390A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
hydrogen
formula
phenoxy
compound
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/CH1981/000037
Other languages
German (de)
English (en)
Inventor
Geigy Ag Ciba
Jozef Drabek
Manfred Boeger
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
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Priority to AU69272/81A priority Critical patent/AU6927281A/en
Priority to NL8120075A priority patent/NL8120075A/nl
Priority to BR8108994A priority patent/BR8108994A/pt
Priority to PCT/CH1981/000037 priority patent/WO1982003390A1/fr
Publication of WO1982003390A1 publication Critical patent/WO1982003390A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/16—Isothiocyanates
    • C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/30—Isothioureas
    • C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms

Definitions

  • the present invention relates to N-phenoxyphenyl isothioureas, processes for their preparation, pesticide compositions which contain the compounds according to the invention as active co-component, and their use for the pest control of pests on animals and plants.
  • N-phenoxyphenyl isothioureas correspond to the Forael
  • R 1 , R 2 and R 3 are each hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy,
  • R 4 and R 5 each C 2 -C 4 alkyl, R 6 C 1 -C 6 alkyl, C 3 -C 6 alkanesyl, or C 3 -C 5 alkynyl, R 7 C 1 - C 10 alkyl, C 3 -C 5 alkenyl or C 3 -C 6 cycloalkyl and R 8 is hydrogen or C 1 -C 10 alkyl.
  • Halogen is fluorine, chlorine, bromine or iodine, but especially chlorine.
  • alkyl, alkoxy, alkenyl and alkynyl groups which are in question in the case of R 1 to R 8 can be saturated or bent.
  • examples of such groups include methyl, methoxy, ethyl, propyl, isopropyl, n-, i-, sec-, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl and its isomers, allyl, methallyl, fropargyl.
  • Cyclopropyl and cyclohexyl are the preferred cycloalkyl groups in R 7 .
  • R 1 is hydrogen, chlorine, methoxy, trifluoroethane or nitro
  • R 2 and R 3 are each hydrogen or chlorine
  • R 4 and R 5 are each ethayl, I ⁇ propyl, i-butyl, sec .-Butyl or tert.-butyl
  • R 6 is C 1 -C 6 alkyl, allyl or fropargyl
  • R 7 is C 1 -C 6 alkyl, cyclopropyl or cyclohexyl
  • R 8 is hydrogen.
  • R 1 is hydrogen, chlorine or trifluoroethane
  • R 2 is hydrogen or chlorine
  • R 3 is hydrogen
  • R 4 and R 5 are each isonropyl or R 4 is ethyl and R 5 is-butyl
  • R 6 is methyl
  • R 7 is tert-butyl or isopropyl
  • R 8 is hydrogen
  • the compounds of Forael I are also in Fora of acid addition salts e.g. Mineral salts before and can be used according to the invention in the form of their salts.
  • the term of the present invention is therefore understood to mean both the free compounds of Forael I and their acid addition salts which are non-toxic to warablütam.
  • the compounds of Forael I can be converted into their acid salts by methods known per se.
  • addition salts are, for example, chloroformic acid, hydrobromic acid, hydroiodic acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, propionic acid, buttaric acid, valeric acid, oxalic acid, malonic acid, succinic acid, malic acid, maleic acid, Fumaric acid, lactic acid, tartaric acid, citric acid, beuzoic acid, phthalic acid, ciatic acid and salicylic acid are suitable.
  • the compounds of Forael I are prepared analogously to known processes, in dea aan e.g. a thiourea from Forael
  • R 1 to R 8 have the meanings already given for Forael I and "Hal" represents a halogen atom, in particular a chlorine or bromine atom.
  • the process is conveniently carried out at a temperature between 0 and 100 ° C, under normal or slightly elevated pressure and preferably in the presence of a solution or diluent which is inert to the reaction substances.
  • Suitable solvents or diluents are e.g. Ethers and ethereal compounds such as diethyl ether, di-isopropyl ether, dioxane and tatrahydrofuran; aromatic hydrocarbons such as benzene, toluene and sylola; and ketones such as acetone, methyl ethyl ketone and cyclohexanone.
  • the compounds of Forael II to be used as starting materials are new. They can easily be obtained from known precursors, for example by using an isothiocyanate of Forael IV
  • the process for the preparation of the starting materials of Forael II is preferably carried out in the presence of a solvent or diluent which is inert to the reactants, at a reaction temperature of 0 to 100 ° C. under normal pressure.
  • a solvent or diluent which is inert to the reactants, at a reaction temperature of 0 to 100 ° C. under normal pressure.
  • Suitable solvents and solvents for this process are the substances already mentioned for the process for the preparation of the end product in Formula I.
  • the compounds of Forael I and the starting materials of Formula II are suitable for controlling pests on animals and plants.
  • the compounds of formulas I and II are particularly suitable for controlling insects, phytopathogenic mites and ticks, e.g. of the order Lepidoptera, Coleoptera, Homoptera, Diptera, Acarina, Thysanoptera, Orthoptera, Anopl ⁇ ra, Siphonaptera, Mallophaga, Thysanura, Is ⁇ ptera, Psocoptera and Hyaenoptera.
  • Compounds of formulas I and II are particularly suitable for controlling insects which damage crops, in particular plant-damaging insects, in ornamental and useful plants, in particular in cotton crops (for example against Spodoptera littoralis and Heliothis virescans) and vegetable cultures (for example against Laptinotarsa decamlineata).
  • Active ingredients of the formulas I and II also have a very favorable action against flies, e.g. Musca domestica and mosquito larvae.
  • the acaricidal activity of the compounds of Forael I extends both to plant-damaging acarines (mites: 2.3. Of the families Tetranychidae, Tarsonemidae, Eriophydae, Tyroglyphidae and Glycyphagidae) as well as to ectoparasitic acarines (mites and ticks: e.g. of the families Ixidaeidae, , Sarccptidae and Der- manyssidae), which cause damage to farm animals.
  • the compounds of formulas I and II can also be used in unchanged form or together with the auxiliaries customary in forauling technology as formulations, such as emulsion concentrates, suspension concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusting agents, granules Feineverkapseiungen in polymeric materials and the like, are used in a known manner.
  • formulations such as emulsion concentrates, suspension concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusting agents, granules Feineverkapseiieux in polymeric materials and the like, are used in a known manner.
  • the application methods such as spraying, atomizing, dusting, scattering or pouring, depend entirely on the intended use. It should be noted here that the biological behavior of the active ingredient of the formula I or II is not significantly influenced by the application method and the type and amount of auxiliary
  • the formulations are prepared in a known manner, for example by intimately mixing and / or grinding the active ingredients with extenders, that is to say with solvents, solid carriers, and, if appropriate, using surface-active substances (surfactants).
  • solvents are: aromatic hydrocarbons, preferably the fractions C 8 to C 12 , ie xylene gels up to substituted naphthalenes, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, strongly polar solvents such as dimethyl sulfoxide or diaethylformamide, and water.
  • powdered rock is usually used as a solid carrier, for example for dusting agents and dispersible powders.
  • calcite, talc, kaolinite, montmorillonite or attapulgite are particularly suitable.
  • highly disperse silicas or highly disperse absorbent polymers can also be added.
  • Porous types such as pumice, broken brick, sepiolite and bentonite can be used as granular carriers, materials such as calcite or sand as non-sorptive carriers.
  • a large number of pre-granulated materials of inorganic or organic nature can be used, from dolomite to crushed nutshells or corn cobs.
  • suitable surface-active substances are nonionic, cationic and / or anionic surfactants with good emulsifying, dispersing and wetting properties.
  • Suitable action-active surfactants are, for example, quaternary ammonium compounds, such as, for example, cetyltriaethylammonium bromide.
  • Suitable anionic surfactants are, for example, soaps, salts of aliphatic monoesters of sulfuric acid, such as sodium lauryl sulfate, salts of sulfonated aromatic compounds, such as sodium dodecylbenzenesulfonate, sodium, calcium or ansaonium lignin sulfonate, butylnaphthalene sulfonate or a mixture of the sodium Diisopropyl and Triisopropylnaphthalenesulfonate.
  • Suitable non-ionic surfactants are, for example, the condensation products of ethylene oxide with fatty alcohols, such as, for example, oleyl alcohol or cetyl alcohol, or with alkyl pheuols, such as, for example, octylphenol, nonylphenol or octylresol.
  • fatty alcohols such as, for example, oleyl alcohol or cetyl alcohol
  • alkyl pheuols such as, for example, octylphenol, nonylphenol or octylresol.
  • Other non-ionic compounds are the partial esters which are derived from long-chain fatty acids and hexitan hydrides, the condensation products of these partial esters with ethylene oxide or lacithins.
  • non-ionic, anionic and cationic tansides commonly used in fonulation technology include: described in the following publications:
  • the formulations generally contain 0.1 to 99%, in particular 0.1 to 95%, active ingredient of the formula I or II and 0 to 25% of a surfactant and 1 to 99.9% of a solid or liquid additive.
  • the formulations can also contain additives such as stabilizers, defoamers, viscosity regulators, binders in the adhesive and also fertilizers for producing special effects.
  • the active compounds of the formula I or II can be formulated, for example, as follows: (data in percent by weight):
  • Formulation examples for liquid active ingredients of the formula I or II emulsion concentrates a) active ingredient 20%
  • Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
  • the active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent is then evaporated off in vacuo.
  • Ready-to-use dusts are obtained by intimately mixing the carriers with the active ingredient.
  • Formulation examples for solid active ingredients of Forael I or II wettable powders a) Active ingredient 20% Na lignin sulfonate 5% Na lauryl sulfate 3% silica 5% kaolin 67%
  • the active ingredient is mixed well with the additives and ground well in a suitable grinder.
  • Spray powder is obtained which can be diluted with water to form suspensions of any desired concentration.
  • Emulsions of any desired concentration can be prepared from this concentrate by dilution with water. Dusts a) active ingredient 5% talc 95% b) active ingredient 8% kaolin fine-particle 92%
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding them in a suitable mill.
  • the active ingredient is mixed with the additives, ground and moistened with water. This mixture is extracted and then dried in an air stream.
  • the finely ground active ingredient is evenly applied in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.
  • Suspension concentrate is obtained.
  • the finely ground active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
  • Example 2 Insecticidal feeding poison effect: Spodoptera littoraiis, Dysdercus fasciams and Heliothis virascens
  • Cotton plants were sprayed with an aqueous emulsion containing 0.052 of the compound to be tested (obtained from a 10% emulsifiable concentrate).
  • Example 3 Insecticides feeding poison effect: Laptiaotarsa decemlineata
  • Example 4 Action against acarines damaging to plants: Tetranychus urticae (OP-sensitive) and Tetranychus cinnabarinus (OP-colerant)
  • the primary leaves of Phaseolus vulgaris plants were 16
  • the infected plants treated in this way were sprayed with a test solution containing 400 or 200 ppm of the compound to be tested to the point of dripping wet.
  • Example 5 Action against ectoparasitic acarines (ticks) Rhipi - cephalus bursa (adults and larvae), Amblyomma hebraeum ( ⁇ adults, nymphs and larvae) and Boophilus microplus (larvae - OP-sensitive and OP-coleranr)
  • Larvae (approx. 50 each), nymphs (approx. 23 each) or adults (approx. 10 each) of the tick species Rhipicephalus bursa, Ambly ⁇ mma hebraeum and Boophilus microplus are used as test objects.
  • the test tiara are briefly in an aqueous emulsion or solution containing 0.1; 1.0; 10; 50 or 100 ppm of the compound to be tested immersed.
  • test tubes The emulsions or solutions in the test tubes are then taken up with cotton wool and the wetted tactile animals are left in the tubes contaminated in this way.
  • the kill rate achieved at each concentration was evaluated after 3 days for larvae and after 14 days for nymphs and adults.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Derives de N-phenoxy-phenyl-isothio-uree de formule (FORMULE) dans laquelle R1, R2 et R3 signifient separement l'hydrogene, un halogene, C1-C4-alkyle, C1-C4 alkoxy, un trifluoromethyle ou nitro, R4 et R5 signifient separement C2-C4-alkyle, R6 signifie C1-C6-alkyle, C3-C6-alkenyle ou C3-C5-alkinyle, R7 signifie C1-C10-alkyle, C3-C5-alkenyle ou C3-C6-cyclo-alkyle et R8 signifie l'hydrogene ou C1-C10-alkyle. L'invention decrit egalement un procede de leur preparation et leur utilisation dans la lutte contre les insectes; ainsi que leurs produits intermediaires a base de phenoxy-phenyle-thio-uree.
PCT/CH1981/000037 1981-03-30 1981-03-30 Derives de phenoxy-phenyle-isothio-uree, produits intermediaires a base de phenoxy-phenyle-thio-uree, leur preparation et leur utilisation dans la lutte contre les insectes Ceased WO1982003390A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU69272/81A AU6927281A (en) 1981-03-30 1981-03-30 Derivatives of phenoxy-phenyle-isothio-urea, intermediary products based on phenoxy-phenyle-thio-urea, preparation thereof and their utilization against insects
NL8120075A NL8120075A (nl) 1981-03-30 1981-03-30 Fenoxyfenylisothiourea, fenoxyfenylthiourea als tussenprodukten, de bereiding en toepassing ervan bij de bestrijding van schadelijke organismen.
BR8108994A BR8108994A (pt) 1981-03-30 1981-03-30 Fenoxifenilisotioureias fenoxifeniltioureias como produtos intermediarios sua preparacao e emprego no combate de pragas
PCT/CH1981/000037 WO1982003390A1 (fr) 1981-03-30 1981-03-30 Derives de phenoxy-phenyle-isothio-uree, produits intermediaires a base de phenoxy-phenyle-thio-uree, leur preparation et leur utilisation dans la lutte contre les insectes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
WOCH81/00037810330 1981-03-30
PCT/CH1981/000037 WO1982003390A1 (fr) 1981-03-30 1981-03-30 Derives de phenoxy-phenyle-isothio-uree, produits intermediaires a base de phenoxy-phenyle-thio-uree, leur preparation et leur utilisation dans la lutte contre les insectes

Publications (1)

Publication Number Publication Date
WO1982003390A1 true WO1982003390A1 (fr) 1982-10-14

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PCT/CH1981/000037 Ceased WO1982003390A1 (fr) 1981-03-30 1981-03-30 Derives de phenoxy-phenyle-isothio-uree, produits intermediaires a base de phenoxy-phenyle-thio-uree, leur preparation et leur utilisation dans la lutte contre les insectes

Country Status (4)

Country Link
AU (1) AU6927281A (fr)
BR (1) BR8108994A (fr)
NL (1) NL8120075A (fr)
WO (1) WO1982003390A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0296120A3 (en) * 1987-06-18 1990-10-10 Ciba-Geigy Ag Aryloxyphenyl ureas, isothio ureas and carbodiimides, their preparation and their use for the control of pests
EP0481921A1 (fr) * 1990-10-18 1992-04-22 Ciba-Geigy Ag Carbodiimides et thiourées substitués et leur utilisation comme pesticides
WO1998045259A3 (fr) * 1997-04-10 1999-02-25 Upjohn Co Compositions antivirales polyaromatiques
CN102993075A (zh) * 2012-11-29 2013-03-27 江苏长青农化股份有限公司 硫脲类杀虫杀螨剂丁醚脲的合成工艺
CN104920408A (zh) * 2015-03-26 2015-09-23 青岛科技大学 一种硫脲类杀虫杀螨剂
CN104082350B (zh) * 2014-07-15 2016-06-15 云南省农业科学院蚕桑蜜蜂研究所 含丁醚脲与除虫菊素的复配杀螨剂

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2465720A1 (fr) * 1979-09-19 1981-03-27 Ciba Geigy Ag Phenoxyphenylisothiourees, procede pour leur preparation et leur application dans la lutte antiparasitaire ainsi que phenoxyphenylthiourees comme produits intermediaires pour la preparation des phenoxyphenylisothiourees ainsi que leur application dans la lutte antiparasitaire

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2465720A1 (fr) * 1979-09-19 1981-03-27 Ciba Geigy Ag Phenoxyphenylisothiourees, procede pour leur preparation et leur application dans la lutte antiparasitaire ainsi que phenoxyphenylthiourees comme produits intermediaires pour la preparation des phenoxyphenylisothiourees ainsi que leur application dans la lutte antiparasitaire

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0296120A3 (en) * 1987-06-18 1990-10-10 Ciba-Geigy Ag Aryloxyphenyl ureas, isothio ureas and carbodiimides, their preparation and their use for the control of pests
EP0481921A1 (fr) * 1990-10-18 1992-04-22 Ciba-Geigy Ag Carbodiimides et thiourées substitués et leur utilisation comme pesticides
WO1998045259A3 (fr) * 1997-04-10 1999-02-25 Upjohn Co Compositions antivirales polyaromatiques
US5958983A (en) * 1997-04-10 1999-09-28 Pharmacia & Upjohn Company Polyaromatic antiviral compositions
US6147116A (en) * 1997-04-10 2000-11-14 Pharmacia & Upjohn Company Polyaromatic antiviral compositions
CN102993075A (zh) * 2012-11-29 2013-03-27 江苏长青农化股份有限公司 硫脲类杀虫杀螨剂丁醚脲的合成工艺
CN104082350B (zh) * 2014-07-15 2016-06-15 云南省农业科学院蚕桑蜜蜂研究所 含丁醚脲与除虫菊素的复配杀螨剂
CN104920408A (zh) * 2015-03-26 2015-09-23 青岛科技大学 一种硫脲类杀虫杀螨剂

Also Published As

Publication number Publication date
AU6927281A (en) 1982-10-19
BR8108994A (pt) 1983-03-01
NL8120075A (nl) 1983-02-01

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