FR2483418A1 - Trihalomethylhydroxylactones et un procede pour leur preparation - Google Patents
Trihalomethylhydroxylactones et un procede pour leur preparation Download PDFInfo
- Publication number
- FR2483418A1 FR2483418A1 FR8110349A FR8110349A FR2483418A1 FR 2483418 A1 FR2483418 A1 FR 2483418A1 FR 8110349 A FR8110349 A FR 8110349A FR 8110349 A FR8110349 A FR 8110349A FR 2483418 A1 FR2483418 A1 FR 2483418A1
- Authority
- FR
- France
- Prior art keywords
- cis
- acid
- keto
- preparation
- dimethyl
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 13
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract description 4
- 239000013067 intermediate product Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 239000002728 pyrethroid Substances 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- QKAHKEDLPBJLFD-UHFFFAOYSA-N 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1OC(=O)C2C1C2(C)C QKAHKEDLPBJLFD-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- MSPJNHHBNOLHOC-UHFFFAOYSA-N 3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(O)=O MSPJNHHBNOLHOC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- MSPJNHHBNOLHOC-ZXZARUISSA-N (1s,2r)-3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)[C@H](C(O)=O)[C@@H]1C(O)=O MSPJNHHBNOLHOC-ZXZARUISSA-N 0.000 description 2
- SCXAMTPGGRKRNY-UHFFFAOYSA-N 2-hydroxy-6,6-dimethyl-2-(trichloromethyl)-3-oxabicyclo[3.1.0]hexan-4-one Chemical compound ClC(Cl)(Cl)C1(O)OC(=O)C2C1C2(C)C SCXAMTPGGRKRNY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- -1 alkali metal salt Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 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 1
- 241000124008 Mammalia Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000000777 acyl halide group Chemical group 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- ULKADLGGTPAKSU-UHFFFAOYSA-M sodium;2,2,2-tribromoacetate Chemical compound [Na+].[O-]C(=O)C(Br)(Br)Br ULKADLGGTPAKSU-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/18—Saturated compounds containing keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8017698 | 1980-05-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2483418A1 true FR2483418A1 (fr) | 1981-12-04 |
| FR2483418B1 FR2483418B1 (enrdf_load_stackoverflow) | 1983-08-26 |
Family
ID=10513721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8110349A Granted FR2483418A1 (fr) | 1980-05-30 | 1981-05-25 | Trihalomethylhydroxylactones et un procede pour leur preparation |
Country Status (15)
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5273843A (en) * | 1975-12-17 | 1977-06-21 | Sumitomo Chem Co Ltd | Preparation of 2,2-dimethyl-3-trihalogeno-acetylcyclopropane carboxyli c acid derivatives |
| EP0041283A1 (en) * | 1980-05-30 | 1981-12-09 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of dihalomethylene-lactones |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2396006A1 (fr) * | 1977-06-27 | 1979-01-26 | Roussel Uclaf | Nouveaux composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinyliques |
-
1981
- 1981-05-06 CA CA000377006A patent/CA1170663A/en not_active Expired
- 1981-05-22 BE BE1/10231A patent/BE888924A/nl not_active IP Right Cessation
- 1981-05-25 FR FR8110349A patent/FR2483418A1/fr active Granted
- 1981-05-27 DK DK234281A patent/DK234281A/da not_active Application Discontinuation
- 1981-05-27 AR AR285473A patent/AR228602A1/es active
- 1981-05-27 ES ES502525A patent/ES8207167A1/es not_active Expired
- 1981-05-27 JP JP7947381A patent/JPS5721382A/ja active Granted
- 1981-05-27 BR BR8103314A patent/BR8103314A/pt not_active IP Right Cessation
- 1981-05-27 DE DE19813121177 patent/DE3121177A1/de active Granted
- 1981-05-27 CH CH3502/81A patent/CH651301A5/de not_active IP Right Cessation
- 1981-05-27 IT IT21988/81A patent/IT1137238B/it active
- 1981-05-27 ZA ZA00813553A patent/ZA813553B/xx unknown
- 1981-05-27 NL NL8102596A patent/NL8102596A/nl not_active Application Discontinuation
- 1981-05-27 SE SE8103371A patent/SE450121B/sv not_active IP Right Cessation
- 1981-12-22 IN IN797/DEL/81A patent/IN157781B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5273843A (en) * | 1975-12-17 | 1977-06-21 | Sumitomo Chem Co Ltd | Preparation of 2,2-dimethyl-3-trihalogeno-acetylcyclopropane carboxyli c acid derivatives |
| EP0041283A1 (en) * | 1980-05-30 | 1981-12-09 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of dihalomethylene-lactones |
Non-Patent Citations (3)
| Title |
|---|
| CA1978 * |
| EXBK/67 * |
| EXBK/76 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3121177C2 (enrdf_load_stackoverflow) | 1989-07-20 |
| IT8121988A0 (it) | 1981-05-27 |
| ES502525A0 (es) | 1982-09-01 |
| NL8102596A (nl) | 1981-12-16 |
| JPS5721382A (en) | 1982-02-04 |
| CA1170663A (en) | 1984-07-10 |
| FR2483418B1 (enrdf_load_stackoverflow) | 1983-08-26 |
| SE450121B (sv) | 1987-06-09 |
| ES8207167A1 (es) | 1982-09-01 |
| DE3121177A1 (de) | 1982-03-04 |
| BR8103314A (pt) | 1982-02-16 |
| IT1137238B (it) | 1986-09-03 |
| ZA813553B (en) | 1982-06-30 |
| BE888924A (nl) | 1981-11-23 |
| AR228602A1 (es) | 1983-03-30 |
| IN157781B (enrdf_load_stackoverflow) | 1986-06-14 |
| DK234281A (da) | 1981-12-01 |
| SE8103371L (sv) | 1981-12-01 |
| CH651301A5 (de) | 1985-09-13 |
| JPH0148271B2 (enrdf_load_stackoverflow) | 1989-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH627431A5 (fr) | Procede de preparation de nouveaux acides cyclopropane carboxyliques comportant un groupement polyhalogene. | |
| FR2483418A1 (fr) | Trihalomethylhydroxylactones et un procede pour leur preparation | |
| WO2008139057A2 (fr) | Procede de preparation de 2-(n-butyl)-3-(4-hydroxybenzoyl)-5-nitrobenzofurane | |
| FR2481274A1 (fr) | Procede de preparation de derives esters d'acides cyclopropane-carboxyliques | |
| EP0573361B1 (fr) | Procédé de préparation d'esters de l'acide 2,2-diméthyl 3-((Z)-2-(alcoxycarbonyl)ethenyl cyclopropane carboxylique et intermédiaires | |
| FR2483404A1 (fr) | Procede de preparation de 2,2-dihalovinyl-cyclopropanecarboxylates | |
| FR2540860A1 (fr) | Nouveaux intermediaires pour la production de derives de l'acide 2-(2-aminothiazol-4-yl) glyoxylique ou d'un de ses sels et le procede de production desdits intermediaires | |
| US4346038A (en) | Oxabicyclo[3.1.0]hexan-2-ones | |
| US4332730A (en) | Dihalomethylenelactone pyrethroid intermediates | |
| CH630601A5 (en) | Cyclopropanecarboxylic acids containing a polyhalogenated group | |
| EP0589784B1 (fr) | Dérivé du 2-éthyl benzo [b] thiophène, son procédé de préparation et son utilisation comme intermédiaire de synthèse | |
| FR2471360A1 (fr) | Halogenocyclobutanones, procede pour leur preparation et produits intermediaires de leur preparation | |
| EP0043307B1 (fr) | Dérivés cyclopropane-1-carboxyliques et leurs sels, préparation et application à la synthèse d'intermédiaires de pyréthrinoides cis | |
| EP0380393B1 (fr) | Preparation d'esters d'acide-2 chloropropionique | |
| US4267381A (en) | Preparation of side-chain fluorinated 3,3-dimethyl-butan-2-one | |
| FR2505327A1 (fr) | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues | |
| JPH0528214B2 (enrdf_load_stackoverflow) | ||
| GB2076818A (en) | Trihalomethylhydroxylactones and keto acids | |
| JPH07133271A (ja) | ベンズアルデヒド誘導体及びそれを中間体とするクロマンカルボン酸誘導体の製法 | |
| FR2689125A1 (fr) | Procédé de préparation de dérivés d'acides gras halogénophénoxyles par halogénation sélective et dérivés d'acides gras halogénophénoxyles. | |
| FR2483419A1 (fr) | Procede de preparation de la n-(2-(2-thenoyl)-thiopropionyl)-glicine | |
| JPH0226612B2 (enrdf_load_stackoverflow) | ||
| JPH0231701B2 (ja) | Arukokishineofuirukuroridoruioyobisonoseizohoho | |
| JPH05230010A (ja) | パラクロロフェニルカルバミン酸エステルの製造方法 | |
| FR2473040A1 (fr) | A-oxonitriles, leur preparation et leur utilisation dans la preparation d'esters cyclopropane-carboxyliques biocides |