SE437263B - Nya cyklopropanderivat till anvendning som insekticider samt sett att framstella dessa - Google Patents
Nya cyklopropanderivat till anvendning som insekticider samt sett att framstella dessaInfo
- Publication number
- SE437263B SE437263B SE7800789A SE7800789A SE437263B SE 437263 B SE437263 B SE 437263B SE 7800789 A SE7800789 A SE 7800789A SE 7800789 A SE7800789 A SE 7800789A SE 437263 B SE437263 B SE 437263B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- atom
- group
- hydrogen
- chemical compound
- Prior art date
Links
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- SRAKKNOEHFCVLC-XINAWCOVSA-N (1R,3R)-2,2-dimethyl-3-[3,3,3-trifluoro-2-(trifluoromethyl)prop-1-enyl]cyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=C(C(F)(F)F)C(F)(F)F)[C@H]1C(O)=O SRAKKNOEHFCVLC-XINAWCOVSA-N 0.000 description 1
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- 238000011069 regeneration method Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000012502 risk assessment Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229940056345 tums Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/42—Halogenated unsaturated alcohols acyclic
- C07C33/423—Halogenated unsaturated alcohols acyclic containing only double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB276377 | 1977-01-24 | ||
GB1221077 | 1977-03-23 | ||
GB3671477 | 1977-09-02 | ||
GB3671577 | 1977-09-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
SE7800789L SE7800789L (sv) | 1978-07-25 |
SE437263B true SE437263B (sv) | 1985-02-18 |
Family
ID=27447244
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7800789A SE437263B (sv) | 1977-01-24 | 1978-01-23 | Nya cyklopropanderivat till anvendning som insekticider samt sett att framstella dessa |
SE8205420A SE445735B (sv) | 1977-01-24 | 1982-09-22 | Kemisk forening till anvendning som mellanprodukt vid framstellning av cyklopropanderivat med insekticida egenskaper jemte sett for dess framstellning |
SE8205421A SE445736B (sv) | 1977-01-24 | 1982-09-22 | Kemisk forening till anvendning som mellanprodukt vid framstellning av cyklopropanderivat med insekticida egenskaper jemte sett for dess framstellning |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8205420A SE445735B (sv) | 1977-01-24 | 1982-09-22 | Kemisk forening till anvendning som mellanprodukt vid framstellning av cyklopropanderivat med insekticida egenskaper jemte sett for dess framstellning |
SE8205421A SE445736B (sv) | 1977-01-24 | 1982-09-22 | Kemisk forening till anvendning som mellanprodukt vid framstellning av cyklopropanderivat med insekticida egenskaper jemte sett for dess framstellning |
Country Status (27)
Country | Link |
---|---|
US (2) | US4183948A (fr) |
JP (2) | JPS5395945A (fr) |
AR (1) | AR218651A1 (fr) |
BE (1) | BE863151A (fr) |
BR (1) | BR7800422A (fr) |
CA (1) | CA1246094A (fr) |
CH (1) | CH638171A5 (fr) |
DD (1) | DD138544A5 (fr) |
DE (2) | DE2858248C2 (fr) |
DK (1) | DK158784C (fr) |
EG (1) | EG13028A (fr) |
ES (3) | ES466281A1 (fr) |
FR (2) | FR2392964A1 (fr) |
GR (1) | GR65619B (fr) |
HU (1) | HU184685B (fr) |
IL (3) | IL53832A (fr) |
IT (1) | IT1092969B (fr) |
LU (1) | LU78930A1 (fr) |
NL (3) | NL189087C (fr) |
NZ (1) | NZ186256A (fr) |
PH (2) | PH13451A (fr) |
PL (1) | PL113130B1 (fr) |
PT (1) | PT67574B (fr) |
SE (3) | SE437263B (fr) |
TR (1) | TR20462A (fr) |
YU (1) | YU15078A (fr) |
ZM (1) | ZM1078A1 (fr) |
Families Citing this family (75)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
US4235927A (en) * | 1978-01-20 | 1980-11-25 | Fmc Corporation | Insecticidal benzylfurylmethyl perhaloalkylvinylcyclopropanecarboxylates |
US4238505A (en) | 1978-01-20 | 1980-12-09 | Fmc Corporation | Insecticidal biphenylmethyl perhaloalkylvinylcyclopropanecarboxylates |
US4243677A (en) * | 1978-01-20 | 1981-01-06 | Fmc Corporation | Insecticidal perhaloalkylvinylcyclopropanecarboxylates |
IN150399B (fr) * | 1978-01-20 | 1982-09-25 | Fmc Corp | |
BG48921A3 (en) * | 1978-02-28 | 1991-06-14 | Montedison Spa | Method for destroying of insects |
US4328237A (en) * | 1978-02-28 | 1982-05-04 | Montedison S.P.A. | Pyrethroids |
US4258202A (en) * | 1978-02-28 | 1981-03-24 | Montedison S.P.A. | Cyclopropanecarboxylic acids and esters |
DE2819788A1 (de) * | 1978-05-05 | 1979-11-08 | Bayer Ag | Benzylester mit fluorsubstituierten aether- und/oder thioaethergruppen und ihre verwendung als insektizide |
DE2831193A1 (de) * | 1978-07-15 | 1980-01-24 | Bayer Ag | Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide |
DE2842541A1 (de) * | 1978-09-29 | 1980-05-22 | Bayer Ag | Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide |
DE2965744D1 (en) * | 1978-10-27 | 1983-07-28 | Ici Plc | Process for separating optical isomers of substituted cyclopropane carboxylic acids; amine salts of substituted cyclopropane carboxylic acids; a substituted cyclopropane carboxylic acid |
EP0010859B1 (fr) * | 1978-10-31 | 1982-12-01 | Imperial Chemical Industries Plc | Procédé de préparation d'esters d'acide cyclopropanecarboxylique |
DE3060562D1 (en) * | 1979-02-14 | 1982-08-12 | Ici Plc | Esters of halogenated substituted cyclopropanoic acids, their preparation and use as insecticides |
DE2916357A1 (de) * | 1979-04-23 | 1980-11-06 | Bayer Ag | Verfahren zur herstellung von 3-(2-aryl-vinyl)-2,2-dimethyl-cyclopropan-1-carbonsaeureestern und neue zwischenprodukte dafuer |
AU531541B2 (en) * | 1979-05-11 | 1983-08-25 | Pitman-Moore Australia Limited | Tickicidal composition |
US4333950A (en) * | 1979-05-24 | 1982-06-08 | Fmc Corporation | (+)-4-Substituted-2-indanol insecticidal ester derivatives |
US4335252A (en) * | 1979-05-24 | 1982-06-15 | Fmc Corporation | Insecticidal pyrethroid enantiomer pair |
US4332815A (en) * | 1979-06-25 | 1982-06-01 | Fmc Corporation | Insecticidal perhaloalkylvinylcyclopropanecarboxylates |
US4341796A (en) | 1979-06-25 | 1982-07-27 | Fmc Corporation | Control of acarids with biphenylmethyl perhaloalkylvinylcyclopropanecarboxylates |
EP0022608B1 (fr) * | 1979-07-13 | 1983-07-06 | Imperial Chemical Industries Plc | Procédé de préparation d'esters d'acides cyclopropane carboxyliques |
DE2939913A1 (de) * | 1979-10-02 | 1981-04-30 | Bayer Ag, 5090 Leverkusen | 3-(2,3-dichlor-3,3-difluor-prop-1-en-1-yl)-2,2-dimethyl-cyclopropancarbonsaeure-fluor-benzylester, verfahren zu ihrer herstellung sowie ihre verwendung in schaedlingsbekaempfungsmitteln |
JPS5692830A (en) * | 1979-12-07 | 1981-07-27 | Ciba Geigy Ag | 22*2**2**dichloroo3**3**3**trifluoropropyl** and 22*2**2**3**trichloroo3**3** difluoropropyl**44chlorocyclobutanee11one and their manufacture |
OA06786A (fr) * | 1980-04-16 | 1982-12-31 | Roussel Uclaf | Nouveaux dérivés de l'acide cyclopropane, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux, les compositions les renfermant et les nouveaux intermediaires obtenus. |
DE3019552A1 (de) * | 1980-05-22 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | 3-(2-chlor-3,3,4,4,4-pentafluor-1-butenyl)-2,2-dimethyl-cyclopropancarbonsaeureester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln |
IT1150963B (it) * | 1980-07-29 | 1986-12-17 | Montedison Spa | Piretroidi |
DE3161438D1 (en) * | 1980-10-23 | 1983-12-22 | Bayer Ag | Process for the preparation of chloro-fluoroalkenyl-substituted cyclopropane-carboxylic-acid esters |
US4368205A (en) * | 1980-10-31 | 1983-01-11 | Fmc Corporation | 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives |
US4417078A (en) * | 1980-12-31 | 1983-11-22 | Fmc Corporation | Process for producing (+)-4-substituted-2-indanols |
US4423255A (en) * | 1980-12-31 | 1983-12-27 | Fmc Corporation | (+)-4-Substituted-2-indanols |
US4362744A (en) * | 1981-03-19 | 1982-12-07 | Fmc Corporation | Trans-3-substituted-1-indanol insecticidal ester derivatives |
DE3225130A1 (de) * | 1981-07-10 | 1983-01-27 | National Research Development Corp., London | Benzylalkoholderivate, verfahren zu deren herstellung und pestizide unter deren verwendung |
DE3127752A1 (de) * | 1981-07-14 | 1983-02-03 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von permethrinsaeurementhylester |
US4415748A (en) * | 1981-08-06 | 1983-11-15 | Fmc Corporation | Intermediates for insecticidal synthetic pyrethroids |
AU550754B2 (en) * | 1981-11-27 | 1986-04-10 | Pitman-Moore Australia Limited | Levamisole and cyhalothrin compositions |
FR2523444B1 (fr) * | 1982-03-16 | 1987-07-24 | Wellcome Australia | Formule antiparasitaire pour mammiferes appliquee localement, contenant une association d'un pyrethroide et d'un thiazole |
GB2130199A (en) * | 1982-10-11 | 1984-05-31 | Ici Plc | An enantiomeric pair of cyhalothrin isomers and process for the preparation thereof |
GB8308507D0 (en) * | 1983-03-28 | 1983-05-05 | Ici Plc | Insecticidal product |
ZA836964B (en) * | 1982-10-11 | 1984-05-30 | Ici Plc | Insecticidal product and preparation thereof |
LV5122A3 (lv) * | 1982-10-11 | 1993-06-10 | Ici Plc | Panemiens (1R,Cis)-3-(Z-hlor-3,3,3-trifluorprop-1-en-1-il)-2,2-dimetilciklopropionskabes un (R)-alpha-ciano-3-(Z-2-hlor-3,3,3-trifluor-prop-1-en-1-il)-2,2-dimetilciklopropionskabes (S)-alpha-ciano-3-fenoksibenzilestera izomeru kristaliska enantiomeru para iegusanai |
EP0107296B1 (fr) * | 1982-10-18 | 1987-07-15 | Imperial Chemical Industries Plc | Produit insecticide et sa préparation |
USH49H (en) | 1983-01-10 | 1986-04-01 | Fmc Corporation | Process for producing 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates |
GB8418331D0 (en) * | 1984-07-18 | 1984-08-22 | Ici Plc | Insecticidal ester |
JPH0674238B2 (ja) * | 1985-09-30 | 1994-09-21 | 財団法人相模中央化学研究所 | 2,2−ジメチルシクロプロパンカルボン酸誘導体 |
DE3900275A1 (de) * | 1989-01-07 | 1990-07-12 | Basf Ag | Substituierte cyclopropancarbonsaeurepropargylester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
GB9311054D0 (en) * | 1993-05-28 | 1993-07-14 | Zeneca Ltd | Preparation of cyclopropane esters |
FR2708930B1 (fr) * | 1993-08-10 | 1995-09-08 | Roussel Uclaf | Nouveaux esters dérivés de l'acide 2,2-diméthyl 3-(3,3,3-trifluoro-1-propényl) cyclopropane carboxylique, leur procédé de préparation et leur application comme pesticides. |
IL115833A (en) * | 1994-11-25 | 1998-10-27 | Zeneca Ltd | Acids 6, 6 - Dihalo - 3, 3 - Dimethyl - 5 - Hydroxy - 7, 7, 7 Triplooroheptanoics and their alkaline esters useful as an intermediate product Insecticides |
DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10007411A1 (de) * | 2000-02-18 | 2001-08-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
AR029677A1 (es) | 2000-06-29 | 2003-07-10 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas y acaricidas |
GB0118137D0 (en) * | 2001-07-25 | 2001-09-19 | Syngenta Ltd | Insecticidal mixture |
AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
US20040058605A1 (en) * | 2002-09-19 | 2004-03-25 | Hansen Michael R. | Polysaccharide treated cellulose fibers |
GB0229803D0 (en) * | 2002-12-20 | 2003-01-29 | Syngenta Ltd | Chemical process |
DE102004001271A1 (de) * | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
DE102004006324A1 (de) * | 2004-02-10 | 2005-08-25 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
US20090281157A1 (en) * | 2006-07-11 | 2009-11-12 | Bayer Cropscience Ag | Active Ingredient Combinations With Insecticidal and Acaricidal Properties |
DE102007007750A1 (de) * | 2006-08-17 | 2008-02-21 | Bayer Cropscience Ag | Avermectinderivate |
DE102006046688B3 (de) * | 2006-09-29 | 2008-01-24 | Siemens Ag | Kälteanlage mit einem warmen und einem kalten Verbindungselement und einem mit den Verbindungselementen verbundenen Wärmerohr |
JP2010505755A (ja) * | 2006-09-30 | 2010-02-25 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 農芸化学的活性成分の根による吸収を向上させるための懸濁濃縮物 |
DE102007045953B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
AU2009243775B2 (en) * | 2008-05-07 | 2015-05-14 | Bayer Intellectual Property Gmbh | Synergistic active ingredient combinations |
GB0808767D0 (en) * | 2008-05-14 | 2008-06-18 | Syngenta Ltd | Process |
EP2127522A1 (fr) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Combinaisons de principes actifs presentant des propriétés insecticides et acaricides |
JP2012521371A (ja) | 2009-03-25 | 2012-09-13 | バイエル・クロップサイエンス・アーゲー | 殺虫特性および殺ダニ特性を有する活性化合物の組合せ |
DE102009028001A1 (de) | 2009-07-24 | 2011-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
EP2382865A1 (fr) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Combinaisons d'agents actifs synergiques |
WO2012150207A1 (fr) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Utilisation de dérivés d'esters de l'acide cyclopropancarboxylique pour lutter contre les insectes résistants aux insecticides |
WO2012150208A1 (fr) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Utilisation d'esters d'alcools benzyliques substitués de l'acide cyclopropane carboxylique pour lutter contre des insectes résistants aux insecticides |
WO2012150221A2 (fr) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Nouveaux esters d'alcools benzyliques halogénés de l'acide cyclopropancarboxique utilisés comme pesticides |
WO2012150205A1 (fr) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Nouveaux esters d'alcools benzyliques substitués de l'acide cyclopropane carboxylique en tant que pesticides |
WO2012150223A1 (fr) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Nouveaux pyridinmethylesters de l'acide cyclopropancarboxylique utilisés comme pesticides |
WO2012150206A2 (fr) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Nouveaux dérivés d'esters de l'acide cyclopropane utilisés comme pesticides |
US20150094474A1 (en) * | 2012-03-13 | 2015-04-02 | Redx Pharma Ltd. | Agricultural chemicals |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS515450B1 (fr) * | 1971-06-29 | 1976-02-20 | ||
JPS5163158A (en) * | 1972-05-25 | 1976-06-01 | Nat Res Dev | 33 chikanshikuropuropankarubonsan oyobi sonojudotainoseiho |
US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
US3862174A (en) * | 1972-06-26 | 1975-01-21 | Sumitomo Chemical Co | Cyclopropanecarboxylates |
JPS5813522B2 (ja) * | 1974-10-24 | 1983-03-14 | 住友化学工業株式会社 | 新しいシクロプロパンカルボン酸エステルを含有する殺虫、殺ダニ剤 |
JPS51131857A (en) * | 1975-05-08 | 1976-11-16 | Kuraray Co Ltd | Process for preparation of substituted cyclopropanecarboxylic acid est ers |
US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
GB1572669A (en) * | 1977-05-26 | 1980-08-28 | Ici Ltd | Manufacture of esters |
US4332815A (en) * | 1979-06-25 | 1982-06-01 | Fmc Corporation | Insecticidal perhaloalkylvinylcyclopropanecarboxylates |
-
1978
- 1978-01-16 US US05/869,615 patent/US4183948A/en not_active Expired - Lifetime
- 1978-01-17 IL IL53832A patent/IL53832A/xx unknown
- 1978-01-18 HU HU78IE821A patent/HU184685B/hu unknown
- 1978-01-18 NZ NZ186256A patent/NZ186256A/xx unknown
- 1978-01-19 CA CA000295309A patent/CA1246094A/fr not_active Expired
- 1978-01-20 BE BE184513A patent/BE863151A/fr not_active IP Right Cessation
- 1978-01-23 GR GR55242A patent/GR65619B/el unknown
- 1978-01-23 IT IT19536/78A patent/IT1092969B/it active Protection Beyond IP Right Term
- 1978-01-23 PL PL1978204165A patent/PL113130B1/pl unknown
- 1978-01-23 YU YU00150/78A patent/YU15078A/xx unknown
- 1978-01-23 LU LU78930A patent/LU78930A1/fr active Protection Beyond IP Right Term
- 1978-01-23 SE SE7800789A patent/SE437263B/sv not_active IP Right Cessation
- 1978-01-23 FR FR7801831A patent/FR2392964A1/fr active Granted
- 1978-01-24 EG EG43/78A patent/EG13028A/xx active
- 1978-01-24 ES ES466281A patent/ES466281A1/es not_active Expired
- 1978-01-24 DE DE2858248A patent/DE2858248C2/de not_active Expired
- 1978-01-24 BR BR7800422A patent/BR7800422A/pt unknown
- 1978-01-24 DE DE2802962A patent/DE2802962C2/de not_active Expired
- 1978-01-24 ZM ZM10/78A patent/ZM1078A1/xx unknown
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- 1978-01-24 PH PH20703A patent/PH13451A/en unknown
- 1978-01-24 PT PT67574A patent/PT67574B/pt unknown
- 1978-01-24 JP JP588278A patent/JPS5395945A/ja active Granted
- 1978-01-24 DD DD78203378A patent/DD138544A5/xx unknown
- 1978-01-24 NL NLAANVRAGE7800824,A patent/NL189087C/xx not_active IP Right Cessation
- 1978-01-24 DK DK034778A patent/DK158784C/da active
- 1978-01-24 CH CH74278A patent/CH638171A5/de not_active IP Right Cessation
- 1978-04-05 ES ES468567A patent/ES468567A1/es not_active Expired
- 1978-04-05 ES ES468566A patent/ES468566A1/es not_active Expired
- 1978-06-15 FR FR7817922A patent/FR2383914A1/fr active Granted
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1979
- 1979-11-06 PH PH23248A patent/PH15508A/en unknown
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1980
- 1980-01-01 AR AR21863580D patent/AR218651A1/es active
- 1980-05-05 IL IL59997A patent/IL59997A0/xx unknown
- 1980-05-05 IL IL59996A patent/IL59996A0/xx unknown
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1982
- 1982-09-22 SE SE8205420A patent/SE445735B/sv not_active IP Right Cessation
- 1982-09-22 SE SE8205421A patent/SE445736B/sv not_active IP Right Cessation
- 1982-12-30 US US06/454,863 patent/US4970330A/en not_active Expired - Fee Related
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1986
- 1986-02-01 JP JP61019209A patent/JPS61178949A/ja active Granted
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1993
- 1993-06-30 NL NL930122C patent/NL930122I1/nl unknown
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1997
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