PT876332E - Derivados de acido fenilacetico processo e produtos intermediarios para a sua preparacao e agentes que os contem - Google Patents

Info

Publication number

PT876332E

PT876332E PT96934659T PT96934659T PT876332E PT 876332 E PT876332 E PT 876332E PT 96934659 T PT96934659 T PT 96934659T PT 96934659 T PT96934659 T PT 96934659T PT 876332 E PT876332 E PT 876332E

Authority

PT

Portugal

Prior art keywords

compounds

methyl

substituent

compound

corresponds

Prior art date

1995-10-23

Links

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• 238000002360 preparation method Methods 0.000 title claims description 25
• 238000000034 method Methods 0.000 title claims description 19
• 239000003795 chemical substances by application Substances 0.000 title claims description 15
• 239000002253 acid Substances 0.000 title description 4
• 239000013067 intermediate product Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 3059
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 1013
• 125000001424 substituent group Chemical group 0.000 claims description 998
• -1 cyano, nitro, hydroxy, mercapto, amino, carboxyl Chemical group 0.000 claims description 239
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 31
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 14
• 125000004104 aryloxy group Chemical group 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
• 229910052757 nitrogen Chemical group 0.000 claims description 13
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 12
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 12
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
• 241000233866 Fungi Species 0.000 claims description 11
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
• 244000045947 parasite Species 0.000 claims description 11
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 9
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 8
• 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 8
• 125000005110 aryl thio group Chemical group 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 239000000463 material Substances 0.000 claims description 7
• 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 5
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
• 239000011593 sulfur Chemical group 0.000 claims description 5
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 4
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 230000000269 nucleophilic effect Effects 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 241000239223 Arachnida Species 0.000 claims description 3
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 241000238631 Hexapoda Species 0.000 claims description 3
• 241000244206 Nematoda Species 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 230000002538 fungal effect Effects 0.000 claims description 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 2
• 239000000654 additive Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 6
• 244000000054 animal parasite Species 0.000 claims 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims 2
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 120
• 239000013543 active substance Substances 0.000 description 43
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• 125000001309 chloro group Chemical group Cl* 0.000 description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 description 23
• 241000196324 Embryophyta Species 0.000 description 18
• 239000000203 mixture Substances 0.000 description 16
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 125000001246 bromo group Chemical group Br* 0.000 description 14
• 239000000243 solution Substances 0.000 description 14
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 13
• 238000005160 1H NMR spectroscopy Methods 0.000 description 13
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 13
• 125000004430 oxygen atom Chemical group O* 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
• 125000000175 2-thienyl group Chemical group S1C([*])=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
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 125000004434 sulfur atom Chemical group 0.000 description 10
• 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
• 238000006243 chemical reaction Methods 0.000 description 9
• 239000000417 fungicide Substances 0.000 description 9
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
• 239000006185 dispersion Substances 0.000 description 8
• 239000003995 emulsifying agent Substances 0.000 description 8
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 239000007921 spray Substances 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 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
• 239000000839 emulsion Substances 0.000 description 6
• 239000000945 filler Substances 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 235000012239 silicon dioxide Nutrition 0.000 description 6
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 5
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 5
• 101150065749 Churc1 gene Proteins 0.000 description 5
• 102100038239 Protein Churchill Human genes 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 239000000499 gel Substances 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
• 229910052938 sodium sulfate Inorganic materials 0.000 description 5
• 235000011152 sodium sulphate Nutrition 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 240000007594 Oryza sativa Species 0.000 description 4
• 235000007164 Oryza sativa Nutrition 0.000 description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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• 239000000460 chlorine Substances 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
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• 239000007787 solid Substances 0.000 description 4
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• 239000005995 Aluminium silicate Substances 0.000 description 3
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• 125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 2
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• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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• 241000255925 Diptera Species 0.000 description 2
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• 241000243785 Meloidogyne javanica Species 0.000 description 2
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