ZA200308400B - Process for the preparation of azoxystrobin and analogues thereof. - Google Patents
Process for the preparation of azoxystrobin and analogues thereof. Download PDFInfo
- Publication number
- ZA200308400B ZA200308400B ZA200308400A ZA200308400A ZA200308400B ZA 200308400 B ZA200308400 B ZA 200308400B ZA 200308400 A ZA200308400 A ZA 200308400A ZA 200308400 A ZA200308400 A ZA 200308400A ZA 200308400 B ZA200308400 B ZA 200308400B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- general formula
- methyl
- cyanophenoxy
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 19
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 title claims description 12
- 239000005730 Azoxystrobin Substances 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- -1 hydroxy, 2- cyanophenoxy, 2,6-difluorophenoxy, 2-nitrophenoxy Chemical group 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
- 150000004702 methyl esters Chemical class 0.000 claims description 8
- 239000012022 methylating agents Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- IELHIACVIURUJP-JXMROGBWSA-N (e)-2-[2-(6-chloropyrimidin-4-yl)oxyphenyl]-3-methoxyprop-2-enoic acid Chemical compound CO\C=C(\C(O)=O)C1=CC=CC=C1OC1=CC(Cl)=NC=N1 IELHIACVIURUJP-JXMROGBWSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 229940049953 phenylacetate Drugs 0.000 description 9
- 239000000010 aprotic solvent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical group [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 150000002642 lithium compounds Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LGPFHQVEKXEUBO-UHFFFAOYSA-N methyl 2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 LGPFHQVEKXEUBO-UHFFFAOYSA-N 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000022244 formylation Effects 0.000 description 5
- 238000006170 formylation reaction Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 230000011987 methylation Effects 0.000 description 5
- 238000007069 methylation reaction Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- BVBSGGBDFJUSIH-UHFFFAOYSA-N Methyl (2-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1O BVBSGGBDFJUSIH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- IEXRKQFZXJSHOB-UHFFFAOYSA-N (4-nitrophenyl) formate Chemical compound [O-][N+](=O)C1=CC=C(OC=O)C=C1 IEXRKQFZXJSHOB-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010013647 Drowning Diseases 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000007351 Smiles rearrangement reaction Methods 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CUEDLSLTSIRGCF-VQHVLOKHSA-N methyl (e)-2-(2-hydroxyphenyl)-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1O CUEDLSLTSIRGCF-VQHVLOKHSA-N 0.000 description 2
- VDHAOUQTBXCDHK-UHFFFAOYSA-N methyl 4-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-oxobutanoate Chemical compound COC(=O)CC(=O)CC1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 VDHAOUQTBXCDHK-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XBECWGJPSXHFCS-UHFFFAOYSA-N imidazole-1-carbaldehyde Chemical class O=CN1C=CN=C1 XBECWGJPSXHFCS-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YRYZZSRRDCTETP-DHZHZOJOSA-N methyl (e)-2-[2-(6-chloropyrimidin-4-yl)oxyphenyl]-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(Cl)=NC=N1 YRYZZSRRDCTETP-DHZHZOJOSA-N 0.000 description 1
- CPIKEDMPXDEUED-UHFFFAOYSA-N methyl 2-(2-phenylmethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1OCC1=CC=CC=C1 CPIKEDMPXDEUED-UHFFFAOYSA-N 0.000 description 1
- FPZYAQQTJYNLMM-UHFFFAOYSA-N methyl 2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]propanoate Chemical compound COC(=O)C(C)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 FPZYAQQTJYNLMM-UHFFFAOYSA-N 0.000 description 1
- BTTXESIFAHCXMK-UHFFFAOYSA-N methyl 2-methoxyprop-2-enoate Chemical group COC(=C)C(=O)OC BTTXESIFAHCXMK-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical class [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0114408.8A GB0114408D0 (en) | 2001-06-13 | 2001-06-13 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308400B true ZA200308400B (en) | 2004-09-02 |
Family
ID=9916496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308400A ZA200308400B (en) | 2001-06-13 | 2003-10-28 | Process for the preparation of azoxystrobin and analogues thereof. |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7084272B2 (es) |
| EP (1) | EP1399427B1 (es) |
| JP (1) | JP2004534794A (es) |
| KR (1) | KR100860378B1 (es) |
| CN (1) | CN1259313C (es) |
| AR (1) | AR035251A1 (es) |
| AT (1) | ATE281438T1 (es) |
| BR (1) | BR0209284B1 (es) |
| CA (1) | CA2445755C (es) |
| DE (1) | DE60201836T2 (es) |
| ES (1) | ES2229121T3 (es) |
| GB (1) | GB0114408D0 (es) |
| IL (2) | IL158577A0 (es) |
| MX (1) | MXPA03011225A (es) |
| PL (1) | PL215304B1 (es) |
| PT (1) | PT1399427E (es) |
| WO (1) | WO2002100837A1 (es) |
| ZA (1) | ZA200308400B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0619941D0 (en) * | 2006-10-09 | 2006-11-15 | Syngenta Ltd | Chemical process |
| IL180134A0 (en) * | 2006-12-17 | 2007-07-04 | David Ovadia | Process for the preparation of substituted cyanophenoxy-pyrimidinyloxy -phenyl acrylate derivatives |
| IL181125A0 (en) * | 2007-02-01 | 2007-07-04 | Maktheshim Chemical Works Ltd | Polymorphs of 3-(e)-2-{2-[6-(2- |
| CN100564362C (zh) | 2007-10-24 | 2009-12-02 | 北京颖泰嘉和科技股份有限公司 | 嘧菌酯及其类似物的制备方法 |
| CN101723905B (zh) * | 2009-11-25 | 2011-09-14 | 大连凯飞精细化工有限公司 | 2-(2-(6-(2-氰基苯氧基)嘧啶-4-氧基)苯基)乙酸甲酯的合成方法 |
| DE102010039715B9 (de) * | 2010-08-24 | 2012-08-02 | Telegärtner Karl Gärtner GmbH | Verfahren, Verbindungsstecker und Verbindungseinrichtung zum Herstellen einer lösbaren Verbindung |
| CN102057916A (zh) * | 2011-01-21 | 2011-05-18 | 陕西美邦农药有限公司 | 一种含有腈苯唑与甲氧基丙烯酸酯类化合物的杀菌组合物 |
| CN102276538B (zh) * | 2011-08-12 | 2015-01-28 | 河北威远生化农药有限公司 | 嘧菌酯及其关键中间体的制备方法 |
| CN102715168B (zh) * | 2012-06-28 | 2013-09-04 | 杭州宇龙化工有限公司 | 一种含有苯醚双唑与嘧菌酯的杀菌组合物及其用途 |
| CN109467537A (zh) * | 2017-09-07 | 2019-03-15 | 北京颖泰嘉和生物科技股份有限公司 | 一种改进型嘧菌酯的纯化和回收方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0391451A1 (en) * | 1986-04-17 | 1990-10-10 | Imperial Chemical Industries Plc | Fungicides |
| US5264440A (en) * | 1989-02-10 | 1993-11-23 | Imperial Chemical Industries Plc | Fungicides |
| US5393837A (en) * | 1993-01-21 | 1995-02-28 | Kuraray Company Ltd. | Polyester composition and process for producing the same |
| ES2162074T3 (es) | 1995-06-28 | 2001-12-16 | Syngenta Ltd | Procedimiento para la preparacion de 2-(6-sustituido pirid-2-iloximetil)fenilacetato. |
| DE19605901A1 (de) | 1996-02-17 | 1997-08-21 | Basf Ag | Verfahren zur Herstellung von 2-(2-Methylphenyl)-3-methoxyacrylsäure -methylester |
| JP3736823B2 (ja) * | 1997-06-26 | 2006-01-18 | 日本写真印刷株式会社 | 機能性物質とその製造方法 |
-
2001
- 2001-06-13 GB GBGB0114408.8A patent/GB0114408D0/en not_active Ceased
-
2002
- 2002-05-03 BR BRPI0209284-0A patent/BR0209284B1/pt active IP Right Grant
- 2002-05-03 PL PL367230A patent/PL215304B1/pl unknown
- 2002-05-03 IL IL15857702A patent/IL158577A0/xx unknown
- 2002-05-03 PT PT02720312T patent/PT1399427E/pt unknown
- 2002-05-03 EP EP02720312A patent/EP1399427B1/en not_active Expired - Lifetime
- 2002-05-03 WO PCT/GB2002/002078 patent/WO2002100837A1/en active IP Right Grant
- 2002-05-03 KR KR1020037016193A patent/KR100860378B1/ko not_active IP Right Cessation
- 2002-05-03 MX MXPA03011225A patent/MXPA03011225A/es active IP Right Grant
- 2002-05-03 DE DE60201836T patent/DE60201836T2/de not_active Expired - Lifetime
- 2002-05-03 AT AT02720312T patent/ATE281438T1/de active
- 2002-05-03 JP JP2003503605A patent/JP2004534794A/ja active Pending
- 2002-05-03 US US10/480,863 patent/US7084272B2/en not_active Expired - Lifetime
- 2002-05-03 CA CA2445755A patent/CA2445755C/en not_active Expired - Fee Related
- 2002-05-03 ES ES02720312T patent/ES2229121T3/es not_active Expired - Lifetime
- 2002-05-03 CN CNB028103688A patent/CN1259313C/zh not_active Expired - Lifetime
- 2002-06-07 AR ARP020102170A patent/AR035251A1/es not_active Application Discontinuation
-
2003
- 2003-10-23 IL IL158577A patent/IL158577A/en unknown
- 2003-10-28 ZA ZA200308400A patent/ZA200308400B/en unknown
-
2006
- 2006-06-20 US US11/425,173 patent/US7244737B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2445755C (en) | 2010-09-21 |
| CA2445755A1 (en) | 2002-12-19 |
| KR20040030667A (ko) | 2004-04-09 |
| KR100860378B1 (ko) | 2008-09-25 |
| PL367230A1 (en) | 2005-02-21 |
| EP1399427A1 (en) | 2004-03-24 |
| DE60201836D1 (de) | 2004-12-09 |
| GB0114408D0 (en) | 2001-08-08 |
| CN1511144A (zh) | 2004-07-07 |
| PL215304B1 (pl) | 2013-11-29 |
| IL158577A (en) | 2010-11-30 |
| AR035251A1 (es) | 2004-05-05 |
| US7244737B2 (en) | 2007-07-17 |
| US7084272B2 (en) | 2006-08-01 |
| PT1399427E (pt) | 2005-01-31 |
| CN1259313C (zh) | 2006-06-14 |
| BR0209284B1 (pt) | 2013-04-16 |
| IL158577A0 (en) | 2004-05-12 |
| BR0209284A (pt) | 2004-07-13 |
| ATE281438T1 (de) | 2004-11-15 |
| JP2004534794A (ja) | 2004-11-18 |
| US20060229450A1 (en) | 2006-10-12 |
| MXPA03011225A (es) | 2004-02-26 |
| DE60201836T2 (de) | 2005-10-27 |
| EP1399427B1 (en) | 2004-11-03 |
| ES2229121T3 (es) | 2005-04-16 |
| WO2002100837A1 (en) | 2002-12-19 |
| US20040242607A1 (en) | 2004-12-02 |
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