FI117199B - 2-[(dihydro)pyratsolyyli-3'-oksimetyleeni]anilidit tuholaistentorjunta-aineina ja fungisideina, näiden yhdisteiden valmistus, välituotteita, näitä yhdisteitä sisältävä seos ja niiden käyttö ja menetelmä tuhosienten ja tuhoeläinten torjumiseksi - Google Patents

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Publication number

FI117199B

FI117199B FI970067A FI970067A FI117199B FI 117199 B FI117199 B FI 117199B FI 970067 A FI970067 A FI 970067A FI 970067 A FI970067 A FI 970067A FI 117199 B FI117199 B FI 117199B

Authority

FI

Finland

Prior art keywords

eller

som

alkyl

formula

och

Prior art date

1994-07-06

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• 238000002360 preparation method Methods 0.000 title claims abstract description 26
• 238000000034 method Methods 0.000 title claims abstract description 15
• 239000000543 intermediate Substances 0.000 title claims abstract description 14
• 239000000417 fungicide Substances 0.000 title claims abstract description 13
• 150000003931 anilides Chemical class 0.000 title claims abstract description 8
• 239000000575 pesticide Substances 0.000 title claims abstract description 7
• 229940051881 anilide analgesics and antipyretics Drugs 0.000 title claims abstract description 6
• 150000001875 compounds Chemical class 0.000 title claims description 180
• 239000000203 mixture Substances 0.000 title claims description 33
• 241000607479 Yersinia pestis Species 0.000 title claims description 17
• -1 di-C 1-6 alkylamino Chemical group 0.000 claims description 415
• 239000001257 hydrogen Substances 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 125000001424 substituent group Chemical group 0.000 claims description 56
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 49
• 150000002431 hydrogen Chemical class 0.000 claims description 49
• 229910052760 oxygen Inorganic materials 0.000 claims description 41
• 239000001301 oxygen Substances 0.000 claims description 39
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 125000004432 carbon atom Chemical group C* 0.000 claims description 36
• 229910052717 sulfur Inorganic materials 0.000 claims description 32
• 125000004434 sulfur atom Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 28
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 15
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• 125000004414 alkyl thio group Chemical group 0.000 claims description 11
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 11
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• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
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• 125000002619 bicyclic group Chemical group 0.000 claims description 9
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• 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• 239000000463 material Substances 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 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 claims description 7
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
• CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims description 6
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• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
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• 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
• 125000005157 alkyl carboxy group Chemical group 0.000 claims description 5
• 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• 239000002689 soil Substances 0.000 claims description 5
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
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• 125000004429 atom Chemical group 0.000 claims description 4
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
• 125000004893 1,1-dimethylethylamino group Chemical group CC(C)(C)N* 0.000 claims description 3
• XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 229910052744 lithium Inorganic materials 0.000 claims description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
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• 229940125890 compound Ia Drugs 0.000 claims description 2
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 2
• 125000003944 tolyl group Chemical group 0.000 claims description 2
• 239000003086 colorant Substances 0.000 claims 10
• 125000004995 haloalkylthio group Chemical group 0.000 claims 3
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
• 230000000269 nucleophilic effect Effects 0.000 claims 2
• 238000010792 warming Methods 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 1
• VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 1
• OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 claims 1
• FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
• 241000282461 Canis lupus Species 0.000 claims 1
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• 108090000623 proteins and genes Proteins 0.000 claims 1
• 239000010802 sludge Substances 0.000 claims 1
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