WO1993014079A1 - Alkylthiothiophenes and alkylthiopolythiophenes, methods of preparing them, and their use - Google Patents
Alkylthiothiophenes and alkylthiopolythiophenes, methods of preparing them, and their use Download PDFInfo
- Publication number
- WO1993014079A1 WO1993014079A1 PCT/EP1993/000060 EP9300060W WO9314079A1 WO 1993014079 A1 WO1993014079 A1 WO 1993014079A1 EP 9300060 W EP9300060 W EP 9300060W WO 9314079 A1 WO9314079 A1 WO 9314079A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- methylthio
- hydrogen
- polythiophenes
- radicals
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 23
- 229930192474 thiophene Natural products 0.000 claims abstract description 21
- 229920000123 polythiophene Polymers 0.000 claims abstract description 15
- 150000003577 thiophenes Chemical class 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
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- 239000000654 additive Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- 241000251730 Chondrichthyes Species 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
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- -1 methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio , 3-methylbutylthio Chemical group 0.000 description 21
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
Definitions
- the present invention relates to thiophenes and polythiophenes of the formula I
- R 1 , R 2 and R 3 independently of one another are hydrogen and Ci-Ci ⁇ -alkylthio
- R 1 , R 2 and R 3 are not simultaneously hydrogen and where R 1 is not hydrogen if R 2 is methylthio and n is 0.
- the invention relates to processes for the preparation of these compounds, compositions comprising at least one thiophene or polythiophene of the formula I '
- R 1 , R 2 and R 3 independently of one another Hydrogen and Ci-Ci ⁇ -alkylthio
- the invention was based on new active substances suitable for pest control as a task.
- the introduction of the halogen substituent is generally carried out according to the method described by Taylor et al. described method (p. 1003) in the presence of N-bromosuccinimide or N-chlorosuccinimide.
- the reaction temperatures are usually 0 ° C to 50 ° C, preferably 10 ° C to 40 ° C.
- the halogenating agents can generally be used in equimolar amounts or in excess.
- Halogenated hydrocarbons such as methylene chloride and tetrachloroethane and protically polar solvents such as acetic acid are particularly suitable as solvents.
- the preparation and implementation of the Grignard compound is advantageously carried out in accordance with the method described by MacEachern et al. described method carried out.
- the reaction temperatures are usually 10 ° C to 60 ° C, preferably 20 ° C to 50 ° C.
- the amount of magnesium shavings or Magnesiu gries' is generally at least equimolar, but is usually used in an excess.
- Suitable solvents are in particular ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether and dioxane, particularly preferably diethyl ether and tert-butyl methyl ether.
- a halogenated thiophene is reacted with a disulfide in general at low temperatures in an aprotic solvent in the presence of an alkali metal organyl.
- the reaction temperatures are usually from -100 ° C to 0 ° C, preferably from -80 ° C to -40 ° C.
- the alkali metal organyls used are generally organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium. into consideration.
- the alkali metal organyls are generally used in an excess of 10 to 100 mol%, preferably 10 to 50 mol%, based on the halothiophene.
- Aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane and tetrahydrofu are used as solvents, particularly preferably ethers.
- the starting materials are generally reacted with one another at least in an equimolar amount. With a view to increasing the yield, however, it may be advantageous to use an excess of 10 mol% to 100 mol%, preferably 10 mol% to 50 mol%, in particular 10 mol%, of the disulfide. % to 20 mol% based on the amount of halogen thiophene.
- Ci-Cis-alkylthio especially Ci-Ce-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio , 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4- Methylpentylthio, 1, 1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,
- radicals R 3 it being possible for the radicals R 3 to be different if the value of n is> 1.
- radicals R 3 it being possible for the radicals R 3 to be different if the value of n is> 1.
- thiophenes and polythiophenes of the formula I ' are particularly preferred in which the substituents and the index have the following meaning:
- R 1 , R- and R 3 independently of one another
- radicals R 3 it being possible for the radicals R 3 to be different if the value of n is> 1.
- R 1 , R 2 and R 3 independently of one another are hydrogen and methyl thio
- the compounds of the formula I ' are suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection and in the hygiene, supply protection and veterinary sectors.
- the harmful insects include from the order of the
- Butterflies for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneuraoneumoneidomoneirone, fumiferella, choristoneura fumiferellaidia unidirectional fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumifeella, choristoneura fumiferida Diaphania nitidalis, Diatrae
- Pectinophora gossypiella Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includesoptera, Spyacoda lodipod, frotana, Scrobipalpulaotha, Diana , Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.
- Diaptera From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chryso ya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Dylobaculexucaceacita, acylucia pacita, acylucia pacificaceae, Cylobaceapura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Mushroom Domica, Lyi
- Thrips for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
- From the order of the hymenoptera for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.
- Heteroptera From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratidularis, Parsma viralisea, Pira .
- bugs Heteroptera
- Acrosternum hilare Blissus leucopterus
- Cyrtopeltis notatus Dysdercus cingulatus
- Dysdercus intermedius Eurygaster integriceps
- Euchistus impictiventris Leptoglossus phyllopus
- Lygus lineolaris Lygus pratidularis
- Parsma viralisea Pira
- suckers for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci,
- Brachycaudus cardui Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dyasphis radicola, Dysaulacorthum pseudosolani, E poasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Megodipononium, Macodipononiumia, Macrosiphoniumia, Macodipa bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphu maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vitarifoli, Vite.
- Orthoptera for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia,
- arachnids such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Ornithodorus moubata, Otobins megnini, Paratetranychus pilosus, Permanyssus gallinae, Phyllocaptrata oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Saccop
- Tetranychus kanzawai Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.
- root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycinae, Heterodera schatii, Hetrodera triflolii, stalks and leaves, e.g. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci,
- root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycinae, Heterodera schatii, Hetroder
- the active compounds can be sprayed as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oldispersions, pastes, dusts, scattering agents, granules hen, nebulizing, dusting, scattering or pouring can be used.
- the application forms depend entirely on the Uses; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
- mineral oil fractions of medium to high boiling point such as kerosene or diesel oil
- coal tar oils as well as oils of vegetable or animal origin
- aliphatic, cyclic and aromatic hydrocarbons e.g. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol.
- Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions) by adding water.
- emulsions, pastes or old dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
- concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
- Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
- III.10 parts by weight of compound no. 4 are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid -N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.
- Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
- Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain meal, tree bark, wood and nutshell meal, cellulose powder and other solid carrier substances.
- Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay,
- the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% by weight.
- the active substance concentrations in the ready-to-use preparations can be varied over a wide range.
- they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used successfully in the fragrance
- Ultra-low-volume processes (ULV) are used, it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
- the amount of active ingredient applied under field conditions is 0.2 to 10, preferably 0.5 to 2.0 kg / ha.
- Oils of various types, herbicides, fungicides, other pesticides, bactericides can be used as active ingredients, if appropriate also only immediately before use
- the active ingredients were:
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93902185A EP0624158A1 (en) | 1992-01-20 | 1993-01-14 | Alkylthiothiophenes and alkylthiopolythiophenes, methods of preparing them, and their use |
JP5512139A JPH07502998A (en) | 1992-01-20 | 1993-01-14 | Thiophene and polythiophene, their production methods and uses |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4201305A DE4201305A1 (en) | 1992-01-20 | 1992-01-20 | Pesticide compsn. contg. (poly)thiophene deriv. - e.g. new alkyl thio-substd. deriv., used as insecticide, acaricide or nematocide |
DEP4201305.4 | 1992-01-20 | ||
DEP4206767.7 | 1992-03-04 | ||
DE19924206767 DE4206767A1 (en) | 1992-03-04 | 1992-03-04 | Pesticide compsn. contg. (poly)thiophene deriv. |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993014079A1 true WO1993014079A1 (en) | 1993-07-22 |
Family
ID=25911078
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1993/000060 WO1993014079A1 (en) | 1992-01-20 | 1993-01-14 | Alkylthiothiophenes and alkylthiopolythiophenes, methods of preparing them, and their use |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0624158A1 (en) |
JP (1) | JPH07502998A (en) |
AU (1) | AU3349493A (en) |
CA (1) | CA2123324A1 (en) |
CZ (1) | CZ155394A3 (en) |
HU (1) | HUT67118A (en) |
IL (1) | IL104408A0 (en) |
MX (1) | MX9300282A (en) |
TW (1) | TW229138B (en) |
WO (1) | WO1993014079A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105340955A (en) * | 2015-11-06 | 2016-02-24 | 南宁邃丛赋语科技开发有限责任公司 | Pesticide composition containing thifluzamide and chlorpyrifos |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2577566A (en) * | 1947-12-13 | 1951-12-04 | Socony Vacuum Oil Co Inc | 3-thienyl thioethers |
US3250787A (en) * | 1962-06-27 | 1966-05-10 | Dow Chemical Co | Alkylthio thiophenes |
WO1986005949A1 (en) * | 1985-04-17 | 1986-10-23 | Fmc Corporation | Photoactive bithienyl pesticides |
-
1993
- 1993-01-14 HU HU9401351A patent/HUT67118A/en unknown
- 1993-01-14 JP JP5512139A patent/JPH07502998A/en active Pending
- 1993-01-14 WO PCT/EP1993/000060 patent/WO1993014079A1/en not_active Application Discontinuation
- 1993-01-14 EP EP93902185A patent/EP0624158A1/en not_active Withdrawn
- 1993-01-14 CZ CZ941553A patent/CZ155394A3/en unknown
- 1993-01-14 CA CA002123324A patent/CA2123324A1/en not_active Abandoned
- 1993-01-14 AU AU33494/93A patent/AU3349493A/en not_active Abandoned
- 1993-01-15 IL IL104408A patent/IL104408A0/en unknown
- 1993-01-20 TW TW082100354A patent/TW229138B/zh active
- 1993-01-20 MX MX9300282A patent/MX9300282A/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2577566A (en) * | 1947-12-13 | 1951-12-04 | Socony Vacuum Oil Co Inc | 3-thienyl thioethers |
US3250787A (en) * | 1962-06-27 | 1966-05-10 | Dow Chemical Co | Alkylthio thiophenes |
WO1986005949A1 (en) * | 1985-04-17 | 1986-10-23 | Fmc Corporation | Photoactive bithienyl pesticides |
Non-Patent Citations (2)
Title |
---|
RUIZ J. P., ET AL.: "SOLUBLE ETHYLMERCAPTO-SUBSTITUTED POLYTHIOPHENES.", MACROMOLECULES, AMERICAN CHEMICAL SOCIETY, US, vol. 22., no. 03., 1 March 1989 (1989-03-01), US, pages 1231 - 1238., XP000127367, ISSN: 0024-9297, DOI: 10.1021/ma00193a039 * |
TETRAHEDRON, (INCL. TETRAHEDRON REPORTS) Bd. 44, Nr. 9, 1988, OXFORD GB Seiten 2403 - 2412 A. MAC EACHERN ET AL. 'Synthesis and Characterization of Alkyl-, Halo- and Hetero-substituted Derivatives of the Potent Phototoxin alpha-Terthienyl' in der Anmeldung erwähnt * |
Also Published As
Publication number | Publication date |
---|---|
CZ155394A3 (en) | 1995-02-15 |
AU3349493A (en) | 1993-08-03 |
CA2123324A1 (en) | 1993-07-22 |
IL104408A0 (en) | 1993-05-13 |
MX9300282A (en) | 1993-07-01 |
HUT67118A (en) | 1995-02-28 |
HU9401351D0 (en) | 1994-08-29 |
TW229138B (en) | 1994-09-01 |
EP0624158A1 (en) | 1994-11-17 |
JPH07502998A (en) | 1995-03-30 |
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