SK76698A3 - 2-(o-[pyrimidin-4-yl]methylenoxy)phenyl acetic acid derivatives and their use for controlling harmful fungi and animal pests - Google Patents

Info

Publication number

SK76698A3

SK76698A3 SK766-98A SK76698A SK76698A3 SK 76698 A3 SK76698 A3 SK 76698A3 SK 76698 A SK76698 A SK 76698A SK 76698 A3 SK76698 A3 SK 76698A3

Authority

SK

Slovakia

Prior art keywords

formula

alkyl

phenyl

pyrimidin

methyl

Prior art date

1995-12-14

Links

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• Global Dossier
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• 241000607479 Yersinia pestis Species 0.000 title claims abstract description 20
• 241000233866 Fungi Species 0.000 title claims abstract description 17
• 241001465754 Metazoa Species 0.000 title claims abstract description 16
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract 4
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 title abstract description 3
• -1 amino, hydroxy, mercapto Chemical class 0.000 claims abstract description 101
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
• 239000001257 hydrogen Substances 0.000 claims abstract description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
• 150000003839 salts Chemical class 0.000 claims abstract description 21
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
• 150000002367 halogens Chemical class 0.000 claims abstract description 13
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
• 125000005389 trialkylsiloxy group Chemical group 0.000 claims abstract description 5
• 125000003118 aryl group Chemical group 0.000 claims abstract description 3
• 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 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 43
• 239000000203 mixture Substances 0.000 claims description 36
• 238000000034 method Methods 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 12
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
• 238000009472 formulation Methods 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• 239000000463 material Substances 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
• 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims 1
• 229940049953 phenylacetate Drugs 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 15
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
• 150000002431 hydrogen Chemical class 0.000 abstract description 4
• 150000001350 alkyl halides Chemical class 0.000 abstract 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
• 150000001875 compounds Chemical class 0.000 description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 241000196324 Embryophyta Species 0.000 description 16
• 239000002253 acid Substances 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• 239000000243 solution Substances 0.000 description 14
• 239000002904 solvent Substances 0.000 description 13
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
• 239000004480 active ingredient Substances 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 125000001309 chloro group Chemical group Cl* 0.000 description 9
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• 229910052717 sulfur Inorganic materials 0.000 description 9
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
• 125000004430 oxygen atom Chemical group O* 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
• 229910052783 alkali metal Inorganic materials 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 239000000417 fungicide Substances 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• 125000004434 sulfur atom Chemical group 0.000 description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 6
• 239000013543 active substance Substances 0.000 description 6
• 150000001340 alkali metals Chemical class 0.000 description 6
• 239000004359 castor oil Substances 0.000 description 6
• 235000019438 castor oil Nutrition 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 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 6
• 229920000056 polyoxyethylene ether Polymers 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
• 241000244206 Nematoda Species 0.000 description 5
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
• 244000309464 bull Species 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 230000000855 fungicidal effect Effects 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
• 229940051841 polyoxyethylene ether Drugs 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 235000011121 sodium hydroxide Nutrition 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 239000011701 zinc Substances 0.000 description 5
• 229910052725 zinc Inorganic materials 0.000 description 5
• RACRYYYCDCAZAL-LVZFUZTISA-N (2e)-2-methoxyimino-n-methyl-2-[2-[(2-methylphenoxy)methyl]phenyl]acetamide Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC=CC=C1C RACRYYYCDCAZAL-LVZFUZTISA-N 0.000 description 4
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
• 230000000895 acaricidal effect Effects 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 235000013339 cereals Nutrition 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 239000011737 fluorine Substances 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 238000000227 grinding Methods 0.000 description 4
• 150000008282 halocarbons Chemical class 0.000 description 4
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
• 235000012054 meals Nutrition 0.000 description 4
• KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
• 239000002480 mineral oil Substances 0.000 description 4
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
• 239000012074 organic phase Substances 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 229910052760 oxygen Inorganic materials 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
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• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000011593 sulfur Substances 0.000 description 4
• FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 4
• WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 3
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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• 238000005507 spraying Methods 0.000 description 3
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