JP4847952B2 - 除草剤として有用なジフルオロメタンスルホニルアニリド誘導体 - Google Patents
除草剤として有用なジフルオロメタンスルホニルアニリド誘導体 Download PDFInfo
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- JP4847952B2 JP4847952B2 JP2007505434A JP2007505434A JP4847952B2 JP 4847952 B2 JP4847952 B2 JP 4847952B2 JP 2007505434 A JP2007505434 A JP 2007505434A JP 2007505434 A JP2007505434 A JP 2007505434A JP 4847952 B2 JP4847952 B2 JP 4847952B2
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- herbicides
- dimethoxypyrimidin
- plants
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- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000208041 Veronica Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- WJPZDRIJJYYRAH-UHFFFAOYSA-N [Zn].[Mo] Chemical compound [Zn].[Mo] WJPZDRIJJYYRAH-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 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 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- KOWWOODYPWDWOJ-LVBPXUMQSA-N elatine Chemical compound C([C@]12CN(C3[C@@]45OCO[C@]44[C@H]6[C@@H](OC)[C@@H]([C@H](C4)OC)C[C@H]6[C@@]3([C@@H]1[C@@H]5OC)[C@@H](OC)CC2)CC)OC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O KOWWOODYPWDWOJ-LVBPXUMQSA-N 0.000 description 1
- KTRGHLZBDIJZLQ-UHFFFAOYSA-N elatine Natural products CCN1CC2(CCC(OC)C34C2C(OC)C5(OCOC56CC(OC)C7CC3(O)C6C7OC)C14)OC(=O)c8ccccc8N9C(=O)CC(C)C9=O KTRGHLZBDIJZLQ-UHFFFAOYSA-N 0.000 description 1
- 239000005712 elicitor Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000012239 gene modification Methods 0.000 description 1
- 230000005017 genetic modification Effects 0.000 description 1
- 235000013617 genetically modified food Nutrition 0.000 description 1
- 235000003869 genetically modified organism Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920005610 lignin Polymers 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical class COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- WROZTZHKRRNHBS-UHFFFAOYSA-N phenyl propaneperoxoate Chemical compound CCC(=O)OOC1=CC=CC=C1 WROZTZHKRRNHBS-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000000280 phytoalexin Substances 0.000 description 1
- 150000001857 phytoalexin derivatives Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000003976 plant breeding Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- IQDUSUMPAWCGJY-UHFFFAOYSA-N pyridine-2,3-dicarbothioic s-acid Chemical compound SC(=O)C1=CC=CN=C1C(S)=O IQDUSUMPAWCGJY-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000020637 scallop Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Xはハロゲンを示し、
YはCH又はNを示し
R1は水素を示しそしてR2は水素又はヒドロキシを示すか、またはR1及びR2は一緒になってそれらが結合している炭素原子と共にC=Oを形成していてもよい。
a)式(II)の化合物
X、Y、R1及びR2は上記と同じ定義を有する、
を、不活性溶媒の存在下に、そしてもし必要ならば酸結合剤の存在下に、ジフルオロメタンスルホニルクロライドと反応させるか、
X及びYは上記と同じ定義を有する、
を、不活性溶媒の存在下に、そしてもし必要ならば酸触媒の存在下に、酸化剤と反応させるか、または
X及びYは上記と同じ定義を有する、
を、不活性溶媒の存在下でアルカリ金属水素錯化合物又はボラン錯体と反応させるかの方法によって製造することができる。
Xはフッ素又は塩素を示し、
YはCH又はNを示し、
R1は水素を示し、
R2は水素又はヒドロキシを示すか、又は
R1とR2は一緒になってそれらが結合している炭素原子と共にC=Oを形成していてもよい。
X及びYは上記と同じ定義を有する、
の化合物を還元剤、例えば塩化ニッケル(II)の存在下における水素化ホウ素ナトリウムと反応させるか、又はラネーニッケルと反応させることで容易に製造することができる。
2−フルオロ−6−[(4,6−ジメトキシピリミジン−2−イル)メチル]アニリン、
2−クロロ−6−[(4,6−ジメトキシピリミジン−2−イル)メチル]アニリン、
2−ブロモ−6−[(4,6−ジメトキシピリミジン−2−イル)メチル]アニリン、
2−ヨード−6−[(4,6−ジメトキシピリミジン−2−イル)メチル]アニリン、
2−フルオロ−6−[(4,6−ジメトキシピリミジン−2−イル)ヒドロキシメチル]アニリン、
2−クロロ−6−[(4,6−ジメトキシピリミジン−2−イル)ヒドロキシメチル]アニリン、
2−ブロモ−6−[(4,6−ジメトキシピリミジン−2−イル)ヒドロキシメチル]アニリン、
2−ヨード−6−[(4,6−ジメトキシピリミジン−2−イル)ヒドロキシメチル]アニリン、
2−フルオロ−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]アニリン、
2−クロロ−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]アニリン、
2−ブロモ−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]アニリン、
2−ヨード−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]アニリン、
2−クロロ−6−[(4,6−ジメトキシトリアジン−2−イル)メチル]アニリン、
2−ブロモ−6−[(4,6−ジメトキシトリアジン−2−イル)メチル]アニリン、
2−ヨード−6−[(4,6−ジメトキシトリアジン−2−イル)メチル]アニリン、
2−フルオロ−6−[(4,6−ジメトキシトリアジン−2−イル)ヒドロキシメチル]アニリン、
2−クロロ−6−[(4,6−ジメトキシトリアジン−2−イル)ヒドロキシメチル]アニリン、
2−ブロモ−6−[(4,6−ジメトキシトリアジン−2−イル)ヒドロキシメチル]アニリン、
2−ヨード−6−[(4,6−ジメトキシトリアジン−2−イル)ヒドロキシメチル]アニリン、
2−フルオロ−6−[(4,6−ジメトキシトリアジン−2−イル)カルボニル]アニリン、
2−クロロ−6−[(4,6−ジメトキシトリアジン−2−イル)カルボニル]アニリン、
2−ブロモ−6−[(4,6−ジメトキシトリアジン−2−イル)カルボニル]アニリン、
2−ヨード−6−[(4,6−ジメトキシトリアジン−2−イル)カルボニル]アニリン、
など。
2−フルオロ−6−[(4,6−ジメトキシピリミジン−2−イル)メチル]−N−ジフルオロメタンスルホンアニリド、
2−クロロ−6−[(4,6−ジメトキシピリミジン−2−イル)メチル]−N−ジフルオロメタンスルホンアニリド、
2−ブロモ−6−[(4,6−ジメトキシピリミジン−2−イル)メチル]−N−ジフルオロメタンスルホンアニリド、
2−フルオロ−6−[(4,6−ジメトキシトリアジン−2−イル)メチル]−N−ジフルオロメタンスルホンアニリド、
など。
2−フルオロ−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]−N−ジフルオロメタンスルホンアニリド、
2−クロロ−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]−N−ジフルオロメタンスルホンアニリド、
2−ブロモ−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]−N−ジフルオロメタンスルホンアニリド、
2−ヨード−6−[(4,6−ジメトキシピリミジン−2−イル)カルボニル]−N−ジフルオロメタンスルホンアニリド、
2−フルオロ−6−[(4,6−ジメトキシトリアジン−2−イル)カルボニル]−N−ジフルオロメタンスルホンアニリド、
など。
によって、目的化合物を得ることができる。
双子葉植物
キカシグサ Rotala indica Koehne
アゼナ Lindernia procumbens Philcox
アメリカアゼナ Lindernia dubia L.Penn.
アゼトウガラシ Lindernia angustifolia
チョウジタデ Ludwigia prostrata Roxburgh
ヒルムシロ Potamogeton distinctus A.Benn
ミゾハコベ Elatine triandra Schk
セリ Oenanthe javanica
単子葉植物
タイヌビエ Echinochloa oryzicola Vasing
マツバイ Eleocharis acicularis L.
クログワイ Eleocharis kuroguwai Ohwi
タマカヤツリ Cyperus difformis L.
ミズガヤツリ Cyperus serotinus Rottboel
ホタルイ Scirpus juncoides Roxburgh
コナギ Monochoria vaginalis Presl
ウリガワ Sagittaria pygmaea Miq
ヘラオモダカ Alisma canaliculatum A.Br.Et Bouche
オモダカ Sagittaria trifolia
ミズアオイ Monochoria korsakowii
アセトアミド系除草剤:例えば、プレチラクロール、ブタクロール、テニルクロール、アラクロールなど;
アミド系除草剤:例えば、クロメプロップ、エトベンザニドなど;
ベンゾフラン系除草剤:例えば、ベンフレセートなど;
インダンジオン系除草剤:例えばインダノファンなど;
ピラゾール系除草剤:例えば、ピラゾレート、ベンゾフェナップ、ピラゾキシフェンなど;
オキサジノン系除草剤:例えば、オキサジクロメフォンなど;
スルホニルウレア系除草剤:ベンスルフロン−メチル、アジムスルフロン、イマゾスルフロン、ピラゾスルフロン−エチル、シクロスルファムロン、エトキシスルフロン、ハロスルフロン−メチルなど;
チオカルバメート系除草剤:例えば、チオベンカルブ、リモネート、ピリブチカルブなど;
トリアジン系除草剤:例えば、ジメタメトリン、シメトリンなど;
トリアゾール系除草剤:例えば、カフェンストロールなど;
キノリン系除草剤:例えば、キンクロラックなど;
イソキサゾール系除草剤:例えば、イソキサフルトールなど;
ジチオホスフェート系除草剤:例えば、アニロホスなど;
オキシアセトアミド系除草剤:例えば、メフェナセット、フルフェナセットなど
テトラゾリノン系除草剤:例えば、フェントラザミドなど;
ジカルボキシイミド系除草剤:例えば、ペントキサゾンなど;
オキサジアゾロン系除草剤:例えば、オキサジアルギル、オキサジアゾンなど;
トリオン系除草剤:例えば、スルコトリオン、ベンゾビシクロンなど;
フェノキシプロピオネート系除草剤:例えば、シハロホップ−ブチルなど
ベンゾイックアシッド系除草剤:例えば、ピリミノバック−メチル、ビスピリバックナトリウム塩など;
ジフェニルエーテル系除草剤:例えば、クロメトキシニル、オキシフルオルフェンなど;ピリジンジカルボチオエート系除草剤:例えば、ジチオピルなど;
フェノキシ系除草剤:例えば、MCPA、MCPBなど;
ウレア系除草剤:例えば、ダイムロン、クミルロンなど;
ナフタレンジオン系除草剤:例えば、キノクラミンなど;
イソキサゾリジノン系除草剤:例えば、クロマゾンなど。
AD−67、BAS−145138、ベノキサコル、クロキントセット−メチル、シオメトリニル、2,4−D、DKA−24、ジクロルミッド、ダイムロン、フェンクロリム、フェンクロラゾール−エチル、フルラゾール、フルキソフェニム、フルラゾール、イソキサジフェン−エチル、メフェンピル−ジエチル、MG−191、ナフタリックアンハイドライド、オキサベトリニル、PPG−1292、R−29148,など。
次の実施例によって、本発明による式(I)の化合物の更なる特定的な製造例及び施用例を示す。しかしながら、本発明は決してこれらのみに限定されるべきものではない。
1H-NMR(300MHz,CDCl3)δ3.99(6H,s),4.97(1H,d),5.99(1H,s),6.13(1H,d),6.61(1H,t),7.07-7.13(1H,m),7.23-7.29(1H,m),7.51-7.53(1H,m),10.57(1H,br)。
1HNMR(300MHz,CDCl3)δ3.94(6H,s),4.30(2H,s),5.92(1H,s),6.74(1H,t),7.18-7.21(1H,m),7.33-7.38(2H,m),11.09(1H,br)。
2−フルオロ−6−[(4,6−ジメトキシトリアジン−2−イル)メチル]−N−ジフルオロメタンスルホンアニリド。
1H-NMR(300MHz,CDCl3)δ4.05(6H,s),4.22(2H,s),6.56(1H,t),7.07-7.28(3H,m),10.16(1H,s)。
28g(収率67%)を白色結晶として得た。
1H-NMR(300MHz,CDCl3)δ3.93(6H,s),6.19(1H,s),6.34(1H,t),7.37-7.43(1H,m),7.63-7.69(2H,m)。
2−フルオロ−6−[(4,6−ジメトキシトリアジン−2−イル)カロボニル]−N−ジフルオロメタンスルホンアニリド。
1H-NMR(300MHz,CDCl3)δ4.10(6H,s),6.48(1H,t),7.36(1H,m),7.45(1H,t),7.55(1H,d),9.08(1H,s)。
1H-NMR(300MHz,CDCl3)δ3.99(6H,s),4.99(1H,br),5.99(1H,s),6.24(1H,s),6.76(1H,t),7.27-7.30(1H,m),7.39-7.42(1H,m),7.64-7.67(1H,m),10.62(1H,br)。
1H-NMR(300MHz,CDCl3)δ3.94(6H,s),4.74(3H,m),5.84(1H,d),5.94(1H,s),6.66-6.73(1H,m),6.88-6.95(1H,m),7.13-7.15(1H,m)。
1H-NMR(300MHz,CDCl3)δ3.91(6H,s),4.01(2H,s),5.18(2H,s),5.81(1H,s),6.62-6.67(1H,m),7.14-7.17(2H,m)。
1H-NMR(300MHz,CDCl3)δ2.04(3H,s),3.93(6H,s),5.07(1H,br), 5.14(1H,s),5.90(1H,s),6.67(1H,t),7.19(1H,dd),7.42(1H,dd)。
活性化合物の製剤の調製
担体:DMF 5重量部
乳化剤:ベンジルオキシポリグリコールエーテル 1重量部
活性化合物の製剤は、活性化合物1重量%と、上記した量の担体と乳化剤とを混合して得られた。製剤の所定量は水で希釈された。
温室内で、1000cm2ポットに水田の土壌を満たし、水を注ぎ約2〜3cmの深さとした。上記試験例1で述べた所定の希釈溶液を水表面に施した。処理後の所定の時間(処理直後、処理後の、1週間、2週間、3週間、4週間、5週間、6週間及び7週間)に、被試験雑草の、ホタルイ、コナギ、一年生広葉雑草(アゼナ、キカシグサ、ミゾハコベ、ヒメミソハギなど)、ミズガヤツリ、ウリカワの種子又は塊茎を接種した。接種後3週間に各々の除草効果を調査した。
温室内で、水田土壌を満たした20cm2のカップに、すべてがスルホニルウレア抵抗性であることが確認されている、ホタルイ(北海道岩見沢地区で採取された)、アゼナ(埼玉県加須地区で採取された)、アゼナ(広島県東広島地区で採取された)、ミゾハコベ(埼玉県加須地区で採取された)の種子を接種した。次いで水を約2〜3cmの深さに注いだ。各々の雑草の発生の始めに、上記試験例1と同様にして調製された所定の活性化合物製剤の希釈溶液を水の表面に施した。この処理の後、水の深さを3cmに保ち、処理後の3週間後で除草効果を調査した。除草効果の評価は、上記試験例1と同様にして行った。80%よりも高い除草効果を示す場合、除草剤として実用性があるものと評価される。異なった地域で生育した植物は除草剤抵抗性を含む生物学的性質が異なるかもしれないという可能性を考慮して、この試験では、二つの異なった地域から採取されたスルホニルウレア抵抗性のアゼナを用いた。
水田に於ける稲の傷害の原因となる除草剤についての過酷な条件を模擬するものである、通常の深さの2cmよりもより浅い植え付け条件下で、移植された稲に対する薬害が評価された。温室内で、2〜2.5葉期の稲(品種 日本晴れ)を、水田土壌を満たした1000cm2ポットに3つの異なった深さで移植した。次いで水を約2から3cmの深さに注ぎ入れた。移植5日後に、所定の上記した試験例1と同様にして調製された各活性化合物製剤の希釈溶液を水の表面に施した。この処理後に3cmの水深を維持し、そして稲の損傷を処理の2週間後に調査した。稲の損傷は完全枯死の場合に100%、損傷無しの場合に0%と評価した。20%よりも小さい傷害を示す場合に、稲の除草剤として実用性があるものとして評価した。
温室内で、水田土壌を満たした500cm2ポットに、タマガヤツリ、ホタルイ、コナギ、一年生広葉雑草(アゼナ、キカシグサ、ミゾハコベ、ヒメミソハギ)及び稲(品種 日本晴れ及びRD−23)の種子を播種した。次いで、水を約0から約0.5cmの深さに注いで湿潤条件とした。所定の上記した試験例1と同様にして調製された各活性化合物製剤の希釈溶液を、稲の2葉期に、植物が生えたポット上に散布した。この処理の2日後に、3cmの水深を保ち、除草効果と稲の損傷を処理の3週後及び2週後に夫々評価した。
本発明の化合物番号1(0.4部)、ベントナイト(モントモリロナイト)(39.6部)、タルク(58部)及びリグノスルホン酸塩(2部)の混合物に水(25部)を加え、良く捏和し、押し出し造粒機で10〜40メッシュの顆粒状にし、40〜50℃で乾燥して顆粒とした。
0.2から2mmの範囲の粒子径分布を有する粘度鉱物粒子を回転混合機に入れた。その回転中に、本発明の化合物番号1(0.2部)を液体稀釈剤と一緒にして噴霧し、均一に濡らし、40〜50℃で乾燥して顆粒とした。
本発明の化合物番号1(30部)、キシレン(55部)、ポリオキシエチレンアルキルフェニルエーテル(8部)、及びアルキルベンゼンスルホン酸カルシウム(7部)を混合し、攪拌して、乳剤を得た。
本発明の化合物番号1(15部)、ホワイトカーボン(含水無定形酸化ケイ素微粉末)と粉末粘土の1:5の混合物(80部)、アルキルベンゼンスルホン酸ナトリウム(2部)、及びアルキルナフタレンスルホン酸ナトリウム−ホルマリン縮合物(3部)を粉末で混合し、水和剤を得た。
本発明の化合物番号1(20部)、リグニンスルホン酸ナトリウム(30部)、ベントナイト(15部)、及び焼成珪藻土粉末(35部)を良く混合し、水を加え、0.3mmのスクリーンを用いて押し出し、乾燥して水分散性の顆粒を得た。
Claims (7)
- Xはフッ素又は塩素を示し、
YはCH又はNを示し、
R1は水素を示し、そして
R2は水素又はヒドロキシを示すか、又は
R1及びR2は、それらが結合している炭素原子と一緒になってC=Oを形成していてもよい、
請求項1に記載の化合物。 - 請求項1の式(I)
a)式(II)
b)R1及びR2が、それらが結合している炭素原子と一緒になってC=Oを形成している場合において、式(Ib)
c)R1が水素、R2がヒドロキシを示す場合において、式(Ic)
を特徴とする、上記製造方法。 - 請求項1の式(I)の化合物の少なくとも一つを含有することを特徴とする除草剤組成物。
- 請求項1の式(I)の化合物の少なくとも一つを、水田雑草及び/又はそれらの生育場所に作用させることを特徴とする、水田雑草を防除する方法。
- 水田雑草の防除のための請求項1の式(I)の化合物の使用。
- 請求項1の式(I)の化合物を、稀釈剤及び/又は界面活性剤と混合することを特徴とする、除草剤組成物の製造方法。
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JP2008201693A (ja) * | 2007-02-19 | 2008-09-04 | Bayer Cropscience Ag | 水田用混合除草剤組成物 |
JP2009046418A (ja) * | 2007-08-20 | 2009-03-05 | Bayer Cropscience Ag | スルホンアニリド類の除草剤としての利用 |
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DE102008037621A1 (de) * | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
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PT2627183T (pt) | 2010-10-15 | 2017-12-11 | Bayer Ip Gmbh | Utilização de herbicidas inibidores de als para controlo de vegetação indesejada em plantas beta vulgaris tolerantes a inibidor de als |
DE102010042786A1 (de) | 2010-10-22 | 2012-04-26 | Bayer Cropscience Ag | Herbizid- Kombination mit einem Dimethoxytriazinyl-substituierten Difluormethansulfonylanilid |
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WO2012084857A2 (de) | 2010-12-21 | 2012-06-28 | Bayer Cropscience Ag | Verfahren zur herstellung von 2-(triazinylcarbonyl)sulfonaniliden |
KR101821847B1 (ko) | 2010-12-21 | 2018-01-24 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | N-술포닐-치환된 옥신돌의 제조 방법 |
KR101613679B1 (ko) * | 2011-02-04 | 2016-04-19 | 이하라케미칼 고교가부시키가이샤 | 아미노페닐피리미디닐알코올 유도체의 제조 방법 및 그 합성 중간체 |
UA117447C2 (uk) | 2011-05-04 | 2018-08-10 | Байєр Інтеллектуал Проперті Гмбх | Застосування гербіцидів інгібіторів als для боротьби з небажаною рослинністю на площі вирощування brassica |
LT2931034T (lt) | 2012-12-13 | 2018-10-10 | Bayer Cropscience Ag | Als slopinančių herbicidų panaudojimas nepageidaujamos augmenijos kontrolei augaluose beta vulgaris, kurie tolerantiški als slopinantiems herbicidams |
CN105325426A (zh) * | 2015-10-29 | 2016-02-17 | 北京燕化永乐生物科技股份有限公司 | 一种除草组合物 |
CA3046044A1 (en) | 2016-12-07 | 2018-06-14 | Bayer Cropscience Aktiengesellschaft | Herbicidal combination containing triafamone and indaziflam |
AR127377A1 (es) | 2021-10-15 | 2024-01-17 | Kws Saat Se & Co Kgaa | Mutantes de beta vulgaris tolerantes a herbicidas inhibidores de als |
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JP2000044546A (ja) * | 1998-07-29 | 2000-02-15 | Kumiai Chem Ind Co Ltd | ジフルオロメタンスルホニルアニリド誘導体、その製造方法及びそれを有効成分とする除草剤 |
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EP1750510B1 (en) | 2007-08-22 |
WO2005096818A1 (en) | 2005-10-20 |
US20070197390A1 (en) | 2007-08-23 |
ECSP066889A (es) | 2006-11-24 |
US7482308B2 (en) | 2009-01-27 |
KR20060132976A (ko) | 2006-12-22 |
BRPI0509403A (pt) | 2007-08-28 |
BRPI0509403B1 (pt) | 2014-04-22 |
KR101169483B1 (ko) | 2012-07-27 |
JP2006056870A (ja) | 2006-03-02 |
EP1750510A1 (en) | 2007-02-14 |
JP2007530613A (ja) | 2007-11-01 |
US20080312084A1 (en) | 2008-12-18 |
DE602005002139D1 (de) | 2007-10-04 |
AU2005230239A1 (en) | 2005-10-20 |
CR8662A (es) | 2008-02-28 |
US7829703B2 (en) | 2010-11-09 |
ATE370655T1 (de) | 2007-09-15 |
ES2288740T3 (es) | 2008-01-16 |
AR048448A1 (es) | 2006-04-26 |
AU2005230239B2 (en) | 2010-09-30 |
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