JP6326043B2 - ５−ハロゲノピラゾールインダニルカルボキサミド類 - Google Patents

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Publication number

JP6326043B2

JP6326043B2 JP2015510767A JP2015510767A JP6326043B2 JP 6326043 B2 JP6326043 B2 JP 6326043B2 JP 2015510767 A JP2015510767 A JP 2015510767A JP 2015510767 A JP2015510767 A JP 2015510767A JP 6326043 B2 JP6326043 B2 JP 6326043B2

Authority

JP

Japan

Prior art keywords

alkyl

cycloalkyl

different

optionally substituted

group

Prior art date

2012-05-09

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• DZGMFITYAJIDHR-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carboxamide Chemical class C1=CC=C2C(C(=O)N)CCC2=C1 DZGMFITYAJIDHR-UHFFFAOYSA-N 0.000 title claims description 11
• -1 hydroxycarbamoyl Chemical group 0.000 claims description 165
• 239000000203 mixture Substances 0.000 claims description 131
• 150000001875 compounds Chemical class 0.000 claims description 108
• 125000005843 halogen group Chemical group 0.000 claims description 103
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 91
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 73
• 239000004480 active ingredient Substances 0.000 claims description 73
• 229910052799 carbon Inorganic materials 0.000 claims description 72
• 229910052801 chlorine Inorganic materials 0.000 claims description 70
• 239000000460 chlorine Substances 0.000 claims description 67
• 239000004009 herbicide Substances 0.000 claims description 64
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
• 238000000034 method Methods 0.000 claims description 57
• 229910052731 fluorine Inorganic materials 0.000 claims description 55
• 239000001257 hydrogen Substances 0.000 claims description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims description 55
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
• 239000011737 fluorine Substances 0.000 claims description 52
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 47
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 46
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 45
• 150000002431 hydrogen Chemical group 0.000 claims description 43
• 238000002360 preparation method Methods 0.000 claims description 43
• 241000233866 Fungi Species 0.000 claims description 36
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
• 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 34
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 33
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 32
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
• 150000002367 halogens Chemical group 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 30
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 29
• 229910052794 bromium Inorganic materials 0.000 claims description 29
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 28
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
• 239000000126 substance Substances 0.000 claims description 24
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 22
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 21
• 230000003032 phytopathogenic effect Effects 0.000 claims description 20
• 230000009261 transgenic effect Effects 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000005103 alkyl silyl group Chemical group 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 11
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 239000011230 binding agent Substances 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
• 125000004740 (C1-C6) haloalkylsulfanyl group Chemical group 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
• 239000004094 surface-active agent Substances 0.000 claims description 6
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
• 230000000844 anti-bacterial effect Effects 0.000 claims description 5
• 238000002156 mixing Methods 0.000 claims description 5
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
• 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 239000004067 bulking agent Substances 0.000 claims description 4
• 239000007822 coupling agent Substances 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 125000001769 aryl amino group Chemical group 0.000 claims description 3
• 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 3
• 230000003197 catalytic effect Effects 0.000 claims description 3
• 239000003337 fertilizer Substances 0.000 claims description 3
• 239000003630 growth substance Substances 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
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• 239000000642 acaricide Substances 0.000 claims description 2
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 241000238631 Hexapoda Species 0.000 description 54
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