PH26571A - 2, 2,-difluorocyclopropyl-ethane derivatives processes for their preparation and their use on pesticides - Google Patents
2, 2,-difluorocyclopropyl-ethane derivatives processes for their preparation and their use on pesticides Download PDFInfo
- Publication number
- PH26571A PH26571A PH37867A PH37867A PH26571A PH 26571 A PH26571 A PH 26571A PH 37867 A PH37867 A PH 37867A PH 37867 A PH37867 A PH 37867A PH 26571 A PH26571 A PH 26571A
- Authority
- PH
- Philippines
- Prior art keywords
- alkyl
- phenyl
- hydrogen
- compounds
- formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 13
- 239000000575 pesticide Substances 0.000 title description 2
- 230000008569 process Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 38
- -1 9-phenanthrenylmethyl Chemical group 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
- 125000006387 trifluoromethyl pyridyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 230000000694 effects Effects 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 235000013601 eggs Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 241001454293 Tetranychus urticae Species 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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- 238000004809 thin layer chromatography Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
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- 239000002585 base Substances 0.000 description 4
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- 235000019341 magnesium sulphate Nutrition 0.000 description 4
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- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
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- 241000219422 Urtica Species 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 229960001413 acetanilide Drugs 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
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- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
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- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/23—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
- C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873740840 DE3740840A1 (de) | 1987-11-27 | 1987-11-27 | 2,2-difluorcyclopropylethanderivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
Publications (1)
Publication Number | Publication Date |
---|---|
PH26571A true PH26571A (en) | 1992-08-19 |
Family
ID=6341739
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PH37867A PH26571A (en) | 1987-11-27 | 1988-11-28 | 2, 2,-difluorocyclopropyl-ethane derivatives processes for their preparation and their use on pesticides |
Country Status (21)
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US (2) | US4983630A (es) |
EP (1) | EP0318425B1 (es) |
JP (1) | JPH02218A (es) |
KR (1) | KR890008080A (es) |
CN (1) | CN1021011C (es) |
AR (1) | AR247547A1 (es) |
AT (1) | ATE73758T1 (es) |
AU (1) | AU619509B2 (es) |
BR (1) | BR8806217A (es) |
CA (1) | CA1316182C (es) |
DD (1) | DD283552A5 (es) |
DE (2) | DE3740840A1 (es) |
DK (1) | DK660788A (es) |
ES (1) | ES2038337T3 (es) |
FI (1) | FI90529C (es) |
GR (1) | GR3004537T3 (es) |
HU (1) | HU204398B (es) |
IL (1) | IL88503A (es) |
PH (1) | PH26571A (es) |
RU (1) | RU1833139C (es) |
ZA (1) | ZA888862B (es) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
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DE3740840A1 (de) * | 1987-11-27 | 1989-06-08 | Schering Ag | 2,2-difluorcyclopropylethanderivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
US5264632A (en) * | 1988-07-19 | 1993-11-23 | Bayer Aktiengesellschaft | 2,2-difluorocyclopropyl derivatives |
DE3824432A1 (de) * | 1988-07-19 | 1990-03-22 | Bayer Ag | 2,2-difluorcyclopropyl-derivate |
US4952863A (en) * | 1989-12-20 | 1990-08-28 | International Business Machines Corporation | Voltage regulator with power boost system |
US5583198A (en) * | 1989-12-22 | 1996-12-10 | Commonwealth Scientific And Industrial Research Organization | Amino acids, peptides or derivatives thereof coupled to fats |
EP0467840A3 (en) * | 1990-07-18 | 1992-10-28 | Ciba-Geigy Ag | Derivatives of cyclopropyle acetic acid |
YU128891A (sh) * | 1990-07-27 | 1994-06-10 | Ciba Geigy Ag. | Derivati karboksimetilciklopropana |
JP2554797Y2 (ja) * | 1993-05-27 | 1997-11-17 | 株式会社 タブチ | 防食スリーブ |
JPH09504508A (ja) * | 1993-09-28 | 1997-05-06 | チバ−ガイギー アクチエンゲゼルシャフト | 殺虫剤及び殺ダニ剤としてのアクリル化スルホンアミド |
AU701863B2 (en) * | 1994-09-08 | 1999-02-04 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
US5717109A (en) * | 1994-09-08 | 1998-02-10 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
US6012873A (en) * | 1997-09-30 | 2000-01-11 | Copple; Robert W. | Buoyant leg platform with retractable gravity base and method of anchoring and relocating the same |
CN1066497C (zh) * | 1998-08-20 | 2001-05-30 | 南亚塑胶工业股份有限公司 | 聚酯混练纤维的制法及其用途 |
IL148326A (en) * | 2002-02-21 | 2008-04-13 | Bromine Compounds Ltd | Brominated esters, methods for their preparation and use thereof as flame retardants |
US7022097B2 (en) | 2003-05-09 | 2006-04-04 | Morton Glickman | Method for treating glandular diseases and malignancies |
JP4645010B2 (ja) * | 2003-07-22 | 2011-03-09 | チッソ株式会社 | フルオロシクロプロパン化合物およびその重合体 |
JP5504898B2 (ja) * | 2010-01-08 | 2014-05-28 | セントラル硝子株式会社 | ジフルオロシクロプロパン化合物の製造方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US3509197A (en) * | 1966-05-11 | 1970-04-28 | Minnesota Mining & Mfg | Fluoro-containing cyclopropanes |
US3759964A (en) * | 1966-09-15 | 1973-09-18 | Zoecon Corp | Dihalomethylene substituted esters and derivatives |
GB1437789A (en) * | 1973-02-16 | 1976-06-03 | Shell Int Research | Cyclopropane derivatives and their use as pesticides |
CA1127658A (en) * | 1977-10-27 | 1982-07-13 | Johannes L.M. Syrier | Esters of cyclopropane carboxylic acid derivatives and process for their preparation |
US4459305A (en) * | 1980-04-10 | 1984-07-10 | Dainippon Sochugiku Kabushiki Kaisha | Cyclopropanecarboxylic acid ester derivatives, a method of manufacturing them, and their uses |
DE3504749A1 (de) * | 1985-02-08 | 1986-08-14 | Schering AG, 1000 Berlin und 4709 Bergkamen | Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
DE3740840A1 (de) * | 1987-11-27 | 1989-06-08 | Schering Ag | 2,2-difluorcyclopropylethanderivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
-
1987
- 1987-11-27 DE DE19873740840 patent/DE3740840A1/de not_active Withdrawn
-
1988
- 1988-11-25 IL IL8850388A patent/IL88503A/en not_active IP Right Cessation
- 1988-11-25 EP EP88730257A patent/EP0318425B1/de not_active Expired - Lifetime
- 1988-11-25 DK DK660788A patent/DK660788A/da not_active Application Discontinuation
- 1988-11-25 BR BR888806217A patent/BR8806217A/pt not_active Application Discontinuation
- 1988-11-25 HU HU886071A patent/HU204398B/hu not_active IP Right Cessation
- 1988-11-25 RU SU884356937A patent/RU1833139C/ru active
- 1988-11-25 DE DE8888730257T patent/DE3869342D1/de not_active Expired - Lifetime
- 1988-11-25 ZA ZA888862A patent/ZA888862B/xx unknown
- 1988-11-25 ES ES198888730257T patent/ES2038337T3/es not_active Expired - Lifetime
- 1988-11-25 AU AU25976/88A patent/AU619509B2/en not_active Ceased
- 1988-11-25 FI FI885488A patent/FI90529C/fi not_active IP Right Cessation
- 1988-11-25 DD DD88322215A patent/DD283552A5/de not_active IP Right Cessation
- 1988-11-25 AT AT88730257T patent/ATE73758T1/de not_active IP Right Cessation
- 1988-11-26 CN CN88108198A patent/CN1021011C/zh not_active Expired - Fee Related
- 1988-11-26 KR KR1019880015623A patent/KR890008080A/ko not_active Application Discontinuation
- 1988-11-28 US US07/276,870 patent/US4983630A/en not_active Expired - Fee Related
- 1988-11-28 PH PH37867A patent/PH26571A/en unknown
- 1988-11-28 JP JP63298458A patent/JPH02218A/ja active Granted
- 1988-11-29 AR AR88312577A patent/AR247547A1/es active
-
1990
- 1990-12-03 US US07/621,618 patent/US5089662A/en not_active Expired - Fee Related
-
1991
- 1991-10-01 CA CA000616187A patent/CA1316182C/en not_active Expired - Fee Related
-
1992
- 1992-05-08 GR GR920400797T patent/GR3004537T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
BR8806217A (pt) | 1989-08-15 |
DD283552A5 (de) | 1990-10-17 |
ZA888862B (en) | 1989-08-30 |
CN1021011C (zh) | 1993-06-02 |
JPH02218A (ja) | 1990-01-05 |
US5089662A (en) | 1992-02-18 |
HU204398B (en) | 1992-01-28 |
GR3004537T3 (es) | 1993-04-28 |
IL88503A0 (en) | 1989-06-30 |
HUT49450A (en) | 1989-10-30 |
CA1316182C (en) | 1993-04-13 |
RU1833139C (ru) | 1993-08-07 |
CN1033271A (zh) | 1989-06-07 |
DK660788A (da) | 1989-05-28 |
FI885488A (fi) | 1989-05-28 |
AU619509B2 (en) | 1992-01-30 |
AR247547A1 (es) | 1995-01-31 |
FI885488A0 (fi) | 1988-11-25 |
ES2038337T3 (es) | 1993-07-16 |
IL88503A (en) | 1994-01-25 |
ATE73758T1 (de) | 1992-04-15 |
DE3869342D1 (de) | 1992-04-23 |
JPH0468295B2 (es) | 1992-11-02 |
EP0318425A1 (de) | 1989-05-31 |
DE3740840A1 (de) | 1989-06-08 |
FI90529B (fi) | 1993-11-15 |
DK660788D0 (da) | 1988-11-25 |
FI90529C (fi) | 1994-02-25 |
KR890008080A (ko) | 1989-07-08 |
EP0318425B1 (de) | 1992-03-18 |
AU2597688A (en) | 1989-06-29 |
US4983630A (en) | 1991-01-08 |
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