EA019495B1 - Спирогетероциклические n-оксипиперидины в качестве пестицидов - Google Patents

Info

Publication number

EA019495B1

EA019495B1 EA201100919A EA201100919A EA019495B1 EA 019495 B1 EA019495 B1 EA 019495B1 EA 201100919 A EA201100919 A EA 201100919A EA 201100919 A EA201100919 A EA 201100919A EA 019495 B1 EA019495 B1 EA 019495B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

formula

compound

group

alkoxy

Prior art date

2008-12-12

Links

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• Global Dossier
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• 239000000575 pesticide Substances 0.000 title abstract description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 1826
• -1 nitro, phenylamino Chemical group 0.000 claims description 213
• 229910052739 hydrogen Inorganic materials 0.000 claims description 157
• 239000001257 hydrogen Substances 0.000 claims description 156
• 150000002431 hydrogen Chemical class 0.000 claims description 143
• 239000000203 mixture Substances 0.000 claims description 138
• 229910052736 halogen Inorganic materials 0.000 claims description 106
• 150000002367 halogens Chemical class 0.000 claims description 102
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 81
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 73
• 238000000034 method Methods 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 61
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 229910052700 potassium Inorganic materials 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 48
• 241000607479 Yersinia pestis Species 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 40
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• 239000000126 substance Substances 0.000 claims description 39
• 125000001188 haloalkyl group Chemical group 0.000 claims description 38
• 239000003921 oil Substances 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 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 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 31
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 31
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 27
• 238000002360 preparation method Methods 0.000 claims description 25
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
• 230000000895 acaricidal effect Effects 0.000 claims description 16
• 239000004009 herbicide Substances 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
• 125000001246 bromo group Chemical group Br* 0.000 claims description 12
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 12
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 12
• 239000002480 mineral oil Substances 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
• 239000003337 fertilizer Substances 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• 239000002917 insecticide Substances 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000004971 nitroalkyl group Chemical group 0.000 claims description 9
• 230000000361 pesticidal effect Effects 0.000 claims description 9
• 125000006239 protecting group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 241001465754 Metazoa Species 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
• 230000002363 herbicidal effect Effects 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 229910052751 metal Inorganic materials 0.000 claims description 8
• 239000002184 metal Substances 0.000 claims description 8
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 7
• 239000000417 fungicide Substances 0.000 claims description 7
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 7
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 239000000642 acaricide Substances 0.000 claims description 5
• 125000005907 alkyl ester group Chemical group 0.000 claims description 5
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
• 235000010446 mineral oil Nutrition 0.000 claims description 5
• 125000003566 oxetanyl group Chemical group 0.000 claims description 5
• 239000011593 sulfur Substances 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
• 235000013311 vegetables Nutrition 0.000 claims description 5
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 239000000729 antidote Substances 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 239000005645 nematicide Substances 0.000 claims description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
• 230000000855 fungicidal effect Effects 0.000 claims description 3
• 230000002147 killing effect Effects 0.000 claims description 3
• 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 150000004714 phosphonium salts Chemical class 0.000 claims description 3
• 239000005648 plant growth regulator Substances 0.000 claims description 3
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 238000002405 diagnostic procedure Methods 0.000 claims 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims 2
• 238000001356 surgical procedure Methods 0.000 claims 2
• 238000002560 therapeutic procedure Methods 0.000 claims 2
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
• 125000004414 alkyl thio group Chemical group 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• 230000008520 organization Effects 0.000 claims 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
• 108700026220 vif Genes Proteins 0.000 claims 1
• 239000002585 base Substances 0.000 description 57
• 241000196324 Embryophyta Species 0.000 description 51
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 238000006243 chemical reaction Methods 0.000 description 39
• 231100000765 toxin Toxicity 0.000 description 39
• 108700012359 toxins Proteins 0.000 description 39
• 239000002904 solvent Substances 0.000 description 38
• 239000003053 toxin Substances 0.000 description 38
• 239000004480 active ingredient Substances 0.000 description 36
• 239000004094 surface-active agent Substances 0.000 description 31
• 235000019198 oils Nutrition 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 229910052740 iodine Inorganic materials 0.000 description 26
• 238000011160 research Methods 0.000 description 24
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 21
• 239000003153 chemical reaction reagent Substances 0.000 description 21
• 239000000654 additive Substances 0.000 description 20
• 239000007787 solid Substances 0.000 description 20
• 241000238631 Hexapoda Species 0.000 description 19
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• 235000014113 dietary fatty acids Nutrition 0.000 description 18
• 239000000194 fatty acid Substances 0.000 description 18
• 229930195729 fatty acid Natural products 0.000 description 18
• 239000007788 liquid Substances 0.000 description 18
• 239000000843 powder Substances 0.000 description 18
• 240000008042 Zea mays Species 0.000 description 17
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 17
• 239000002253 acid Substances 0.000 description 17
• 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 16
• 150000001412 amines Chemical class 0.000 description 16
• 239000008187 granular material Substances 0.000 description 16
• 230000000749 insecticidal effect Effects 0.000 description 16
• 229910052727 yttrium Inorganic materials 0.000 description 16
• 235000019441 ethanol Nutrition 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• 229910052708 sodium Inorganic materials 0.000 description 14
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 108090000623 proteins and genes Proteins 0.000 description 13
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
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• 239000011734 sodium Substances 0.000 description 12
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• 230000009261 transgenic effect Effects 0.000 description 11
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• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
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• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 9
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• 239000003513 alkali Substances 0.000 description 9
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• JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 9
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• WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 6
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