JP2007530473A - 除草剤−薬害軽減剤の混合剤 - Google Patents

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Publication number

JP2007530473A

JP2007530473A JP2007504300A JP2007504300A JP2007530473A JP 2007530473 A JP2007530473 A JP 2007530473A JP 2007504300 A JP2007504300 A JP 2007504300A JP 2007504300 A JP2007504300 A JP 2007504300A JP 2007530473 A JP2007530473 A JP 2007530473A

Authority

JP

Japan

Prior art keywords

iii

alkyl

halogen

hydrogen

group

Prior art date

2004-03-27

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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• 239000000203 mixture Substances 0.000 title claims abstract description 56
• 239000001257 hydrogen Substances 0.000 claims abstract description 102
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 102
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 98
• 150000002367 halogens Chemical class 0.000 claims abstract description 98
• 150000001875 compounds Chemical class 0.000 claims abstract description 97
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 55
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 52
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 52
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 31
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
• 239000003814 drug Substances 0.000 claims abstract description 24
• 229940079593 drug Drugs 0.000 claims abstract description 24
• 150000003839 salts Chemical class 0.000 claims abstract description 24
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 19
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
• 125000003118 aryl group Chemical group 0.000 claims abstract description 14
• 230000000116 mitigating effect Effects 0.000 claims abstract description 14
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 13
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 12
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 12
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 12
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 10
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
• RFMQOHXWHFHOJF-UHFFFAOYSA-N cyano thiocyanate Chemical compound N#CSC#N RFMQOHXWHFHOJF-UHFFFAOYSA-N 0.000 claims abstract description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 43
• 230000002363 herbicidal effect Effects 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 238000009472 formulation Methods 0.000 claims description 16
• 244000038559 crop plants Species 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 15
• MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 13
• 230000009261 transgenic effect Effects 0.000 claims description 13
• GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 9
• YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 9
• OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 7
• 239000000654 additive Substances 0.000 claims description 6
• 235000013311 vegetables Nutrition 0.000 claims description 5
• UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 claims description 3
• JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 3
• NYDKNJDNBUFWRJ-UHFFFAOYSA-N n-[4-(dimethylcarbamoylamino)phenyl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(=O)N(C)C)C=C1 NYDKNJDNBUFWRJ-UHFFFAOYSA-N 0.000 claims description 3
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 238000009394 selective breeding Methods 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 7
• 239000000126 substance Substances 0.000 abstract description 4
• 125000004429 atom Chemical group 0.000 abstract description 2
• 125000005843 halogen group Chemical group 0.000 abstract description 2
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
• 235000018936 Vitellaria paradoxa Nutrition 0.000 abstract 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
• MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 156
• ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 148
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 98
• -1 methoxy, methoxymethyl Chemical group 0.000 description 90
• 241000196324 Embryophyta Species 0.000 description 69
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 65
• 239000004009 herbicide Substances 0.000 description 43
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 23
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 22
• 125000000623 heterocyclic group Chemical group 0.000 description 20
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 19
• 229910052760 oxygen Inorganic materials 0.000 description 19
• 238000011282 treatment Methods 0.000 description 18
• 239000000460 chlorine Substances 0.000 description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 17
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 15
• 229910052801 chlorine Inorganic materials 0.000 description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
• 125000004093 cyano group Chemical group *C#N 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• 150000002430 hydrocarbons Chemical group 0.000 description 12
• 235000010469 Glycine max Nutrition 0.000 description 11
• 239000001301 oxygen Substances 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 244000068988 Glycine max Species 0.000 description 10
• 244000062793 Sorghum vulgare Species 0.000 description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
• 229910052799 carbon Inorganic materials 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 125000005842 heteroatom Chemical group 0.000 description 10
• 239000002689 soil Substances 0.000 description 10
• 240000007594 Oryza sativa Species 0.000 description 9
• 235000007164 Oryza sativa Nutrition 0.000 description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
• 240000008042 Zea mays Species 0.000 description 9
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
• 235000005822 corn Nutrition 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
• 239000008187 granular material Substances 0.000 description 9
• 235000019713 millet Nutrition 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 235000009566 rice Nutrition 0.000 description 9
• 125000001424 substituent group Chemical group 0.000 description 9
• 239000011593 sulfur Substances 0.000 description 9
• 244000075850 Avena orientalis Species 0.000 description 8
• VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 description 8
• MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
• 235000013339 cereals Nutrition 0.000 description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• 238000005507 spraying Methods 0.000 description 8
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 7
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
• 235000007319 Avena orientalis Nutrition 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 235000021307 Triticum Nutrition 0.000 description 7
• 241000209140 Triticum Species 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 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 description 7
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 240000002791 Brassica napus Species 0.000 description 6
• 235000004977 Brassica sinapistrum Nutrition 0.000 description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000001931 aliphatic group Chemical group 0.000 description 6
• ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
• 239000011737 fluorine Substances 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• 235000000346 sugar Nutrition 0.000 description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 5
• 229920000742 Cotton Polymers 0.000 description 5
• 244000299507 Gossypium hirsutum Species 0.000 description 5
• 235000007340 Hordeum vulgare Nutrition 0.000 description 5
• 240000005979 Hordeum vulgare Species 0.000 description 5
• 241000219843 Pisum Species 0.000 description 5
• 241000220259 Raphanus Species 0.000 description 5
• 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 5
• 235000007238 Secale cereale Nutrition 0.000 description 5
• 244000082988 Secale cereale Species 0.000 description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
• 230000034303 cell budding Effects 0.000 description 5
• IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
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• 238000009331 sowing Methods 0.000 description 5
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• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 4
• YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 4
• 239000002794 2,4-DB Substances 0.000 description 4
• OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 description 4
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• 238000007796 conventional method Methods 0.000 description 4
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• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
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• 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 description 3
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• QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 2
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• ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 description 2
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• AXHCGXRBOHBEQA-UHFFFAOYSA-N 2-(5-chloro-2-methylphenoxy)acetic acid Chemical compound CC1=CC=C(Cl)C=C1OCC(O)=O AXHCGXRBOHBEQA-UHFFFAOYSA-N 0.000 description 2
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