EA000786B1 - Производные фенилуксусной кислоты, способ и промежуточные продукты для их получения и содержащие их средства - Google Patents

Info

Publication number

EA000786B1

EA000786B1 EA199800388A EA199800388A EA000786B1 EA 000786 B1 EA000786 B1 EA 000786B1 EA 199800388 A EA199800388 A EA 199800388A EA 199800388 A EA199800388 A EA 199800388A EA 000786 B1 EA000786 B1 EA 000786B1

Authority

EA

Eurasian Patent Office

Prior art keywords

compounds

formula

alkyl

aryl

methyl

Prior art date

1995-10-23

Links

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• 238000000034 method Methods 0.000 title claims abstract description 24
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract description 6
• 239000003795 chemical substances by application Substances 0.000 title claims description 10
• 239000013067 intermediate product Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 3088
• 125000001424 substituent group Chemical group 0.000 claims abstract description 981
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 974
• -1 nitro, hydroxyl Chemical group 0.000 claims abstract description 304
• 125000003118 aryl group Chemical group 0.000 claims abstract description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
• 239000001257 hydrogen Substances 0.000 claims abstract description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 34
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 24
• 241000607479 Yersinia pestis Species 0.000 claims abstract description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 21
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
• 150000002367 halogens Chemical group 0.000 claims abstract description 21
• 241000233866 Fungi Species 0.000 claims abstract description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims abstract description 18
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 18
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 18
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 18
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 16
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 14
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 14
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 13
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 13
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 13
• 125000005110 aryl thio group Chemical group 0.000 claims abstract description 13
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 12
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 239000001301 oxygen Substances 0.000 claims abstract description 12
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
• 239000000463 material Substances 0.000 claims abstract description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 8
• 239000011593 sulfur Substances 0.000 claims abstract description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 7
• 241000244206 Nematoda Species 0.000 claims abstract description 6
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
• 241000239223 Arachnida Species 0.000 claims abstract description 4
• 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 4
• 239000000654 additive Substances 0.000 claims abstract description 4
• 150000001412 amines Chemical class 0.000 claims abstract description 4
• 150000002148 esters Chemical class 0.000 claims abstract description 4
• 229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 3
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 3
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 3
• 241000238631 Hexapoda Species 0.000 claims abstract description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
• 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims 7
• 125000004414 alkyl thio group Chemical group 0.000 claims 3
• 125000003282 alkyl amino group Chemical group 0.000 claims 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
• 125000004438 haloalkoxy group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 25
• 238000002360 preparation method Methods 0.000 abstract description 16
• 241001465754 Metazoa Species 0.000 abstract description 6
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract description 4
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 abstract description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 265
• 239000013543 active substance Substances 0.000 description 36
• 101150065749 Churc1 gene Proteins 0.000 description 30
• 102100038239 Protein Churchill Human genes 0.000 description 30
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• 239000003921 oil Substances 0.000 description 17
• 239000000243 solution Substances 0.000 description 16
• 241000196324 Embryophyta Species 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 14
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 14
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 13
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 13
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 13
• 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 12
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 12
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 12
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 12
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 12
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 12
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 239000000417 fungicide Substances 0.000 description 10
• 125000004434 sulfur atom Chemical group 0.000 description 10
• HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 8
• OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
• 238000010410 dusting Methods 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000013256 coordination polymer Substances 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 238000005507 spraying Methods 0.000 description 7
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 241000209140 Triticum Species 0.000 description 6
• 235000021307 Triticum Nutrition 0.000 description 6
• 235000013339 cereals Nutrition 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
• 239000000945 filler Substances 0.000 description 6
• 235000013312 flour Nutrition 0.000 description 6
• 239000008187 granular material Substances 0.000 description 6
• 125000004430 oxygen atom Chemical group O* 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 240000007594 Oryza sativa Species 0.000 description 5
• 235000007164 Oryza sativa Nutrition 0.000 description 5
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 238000005516 engineering process Methods 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 235000009566 rice Nutrition 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 229910052938 sodium sulfate Inorganic materials 0.000 description 5
• 235000011152 sodium sulphate Nutrition 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 4
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
• 159000000000 sodium salts Chemical class 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 241000894007 species Species 0.000 description 4
• 238000009827 uniform distribution Methods 0.000 description 4
• 235000013311 vegetables Nutrition 0.000 description 4
• NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
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• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
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