JP4384910B2 - 除草剤及び薬害軽減剤の組合せ - Google Patents

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Publication number

JP4384910B2

JP4384910B2 JP2003526192A JP2003526192A JP4384910B2 JP 4384910 B2 JP4384910 B2 JP 4384910B2 JP 2003526192 A JP2003526192 A JP 2003526192A JP 2003526192 A JP2003526192 A JP 2003526192A JP 4384910 B2 JP4384910 B2 JP 4384910B2

Authority

JP

Japan

Prior art keywords

herbicide

plants

safener

formula

group

Prior art date

2001-09-13

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.)

Expired - Lifetime

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• 239000004009 herbicide Substances 0.000 title claims description 70
• 230000002363 herbicidal effect Effects 0.000 title claims description 64
• 239000000203 mixture Substances 0.000 claims description 52
• 241000196324 Embryophyta Species 0.000 claims description 36
• 150000001875 compounds Chemical class 0.000 claims description 24
• 244000038559 crop plants Species 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 9
• 240000008042 Zea mays Species 0.000 claims description 7
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 7
• 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 7
• 235000005822 corn Nutrition 0.000 claims description 7
• 240000007594 Oryza sativa Species 0.000 claims description 6
• 235000007164 Oryza sativa Nutrition 0.000 claims description 6
• 235000009566 rice Nutrition 0.000 claims description 6
• 240000005979 Hordeum vulgare Species 0.000 claims description 4
• 235000007340 Hordeum vulgare Nutrition 0.000 claims description 4
• 235000021307 Triticum Nutrition 0.000 claims description 4
• 150000003839 salts Chemical class 0.000 claims description 4
• 235000007319 Avena orientalis Nutrition 0.000 claims description 3
• 244000075850 Avena orientalis Species 0.000 claims description 3
• 229920000742 Cotton Polymers 0.000 claims description 3
• 244000068988 Glycine max Species 0.000 claims description 3
• 235000010469 Glycine max Nutrition 0.000 claims description 3
• 235000007238 Secale cereale Nutrition 0.000 claims description 3
• 244000082988 Secale cereale Species 0.000 claims description 3
• 235000007558 Avena sp Nutrition 0.000 claims description 2
• 244000299507 Gossypium hirsutum Species 0.000 claims description 2
• 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
• 240000006394 Sorghum bicolor Species 0.000 claims 1
• 229940100389 Sulfonylurea Drugs 0.000 claims 1
• 244000098338 Triticum aestivum Species 0.000 claims 1
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
• 239000013543 active substance Substances 0.000 description 35
• -1 1-methylprop-2-en-1-yl Chemical group 0.000 description 26
• 238000009472 formulation Methods 0.000 description 18
• 150000002148 esters Chemical class 0.000 description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
• 239000002689 soil Substances 0.000 description 14
• 229910052736 halogen Inorganic materials 0.000 description 13
• 150000002367 halogens Chemical class 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 239000008187 granular material Substances 0.000 description 12
• 239000000126 substance Substances 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• 239000004495 emulsifiable concentrate Substances 0.000 description 10
• 125000000623 heterocyclic group Chemical group 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 125000000217 alkyl group Chemical group 0.000 description 9
• 239000000839 emulsion Substances 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• 229910052717 sulfur Chemical group 0.000 description 8
• 239000004562 water dispersible granule Substances 0.000 description 8
• 230000000885 phytotoxic effect Effects 0.000 description 7
• 239000004563 wettable powder Substances 0.000 description 7
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 239000003995 emulsifying agent Substances 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000007921 spray Substances 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
• 0 CCN(C*)C(c(cc1)ccc1S(NC(c(cccc1)c1OC)=O)(=*)=O)=O Chemical compound CCN(C*)C(c(cc1)ccc1S(NC(c(cccc1)c1OC)=O)(=*)=O)=O 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 125000000304 alkynyl group Chemical group 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 125000001188 haloalkyl group Chemical group 0.000 description 5
• 229920000151 polyglycol Polymers 0.000 description 5
• 239000010695 polyglycol Substances 0.000 description 5
• 239000004094 surface-active agent Substances 0.000 description 5
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• 125000002252 acyl group Chemical group 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 238000007796 conventional method Methods 0.000 description 4
• 125000004093 cyano group Chemical group *C#N 0.000 description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
• 235000014113 dietary fatty acids Nutrition 0.000 description 4
• 239000000194 fatty acid Substances 0.000 description 4
• 229930195729 fatty acid Natural products 0.000 description 4
• 125000004438 haloalkoxy group Chemical group 0.000 description 4
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
• 150000004702 methyl esters Chemical class 0.000 description 4
• 230000000116 mitigating effect Effects 0.000 description 4
• 230000009467 reduction Effects 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 3
• XBYZOHTXPQOOJM-UHFFFAOYSA-N 1,2-oxazol-3-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C=1C=CON=1 XBYZOHTXPQOOJM-UHFFFAOYSA-N 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 3
• 239000004372 Polyvinyl alcohol Substances 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 240000000111 Saccharum officinarum Species 0.000 description 3
• 235000007201 Saccharum officinarum Nutrition 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• 244000062793 Sorghum vulgare Species 0.000 description 3
• 241000209140 Triticum Species 0.000 description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
• 125000004414 alkyl thio group Chemical group 0.000 description 3
• 235000012211 aluminium silicate Nutrition 0.000 description 3
• 125000003118 aryl group Chemical group 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• 235000013339 cereals Nutrition 0.000 description 3
• WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 3
• 239000000084 colloidal system Substances 0.000 description 3
• 201000010099 disease Diseases 0.000 description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• 239000002270 dispersing agent Substances 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• 239000003814 drug Substances 0.000 description 3
• 150000002191 fatty alcohols Chemical class 0.000 description 3
• 239000003337 fertilizer Substances 0.000 description 3
• FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 3
• 238000000227 grinding Methods 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 239000003112 inhibitor Substances 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 description 3
• 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 3
• 229920002451 polyvinyl alcohol Polymers 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• 238000001694 spray drying Methods 0.000 description 3
• 229940104261 taurate Drugs 0.000 description 3
• XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
• 230000000007 visual effect Effects 0.000 description 3
• 239000000080 wetting agent Substances 0.000 description 3
• RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 2
• NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
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• NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 description 2
• DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 description 2
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• QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 description 2
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
• QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 description 2
• AOQMRUTZEYVDIL-UHFFFAOYSA-N Flupoxam Chemical compound C=1C=C(Cl)C(COCC(F)(F)C(F)(F)F)=CC=1N1N=C(C(=O)N)N=C1C1=CC=CC=C1 AOQMRUTZEYVDIL-UHFFFAOYSA-N 0.000 description 2
• YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 description 2
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
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• 239000005589 Oxasulfuron Substances 0.000 description 2
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• LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 2
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