JPS5846071A - 置換フエニルスルホニルウレア誘導体、その中間体、それらの製法、及び除草剤 - Google Patents
置換フエニルスルホニルウレア誘導体、その中間体、それらの製法、及び除草剤Info
- Publication number
- JPS5846071A JPS5846071A JP56144590A JP14459081A JPS5846071A JP S5846071 A JPS5846071 A JP S5846071A JP 56144590 A JP56144590 A JP 56144590A JP 14459081 A JP14459081 A JP 14459081A JP S5846071 A JPS5846071 A JP S5846071A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- general formula
- lower alkyl
- substituted
- Prior art date
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 22
- 239000004009 herbicide Substances 0.000 title claims abstract description 11
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 7
- -1 2-chlorophenoxy Chemical group 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004020 conductor Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 abstract description 31
- 238000000034 method Methods 0.000 abstract description 17
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- CAHZKICHVXSVPO-UHFFFAOYSA-N (4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound COC1=CC(C)=NC(NC(N)=O)=N1 CAHZKICHVXSVPO-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
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- 229910052739 hydrogen Inorganic materials 0.000 description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 238000006243 chemical reaction Methods 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
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- 238000005507 spraying Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 230000009931 harmful effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 244000301850 Cupressus sempervirens Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 240000003173 Drymaria cordata Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 229940072049 amyl acetate Drugs 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
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- KHBQMWCZKVMBLN-IDEBNGHGSA-N benzenesulfonamide Chemical compound NS(=O)(=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 KHBQMWCZKVMBLN-IDEBNGHGSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/65—N-sulfonylisocyanates
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Display Devices Of Pinball Game Machines (AREA)
- Cereal-Derived Products (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56144590A JPS5846071A (ja) | 1981-09-16 | 1981-09-16 | 置換フエニルスルホニルウレア誘導体、その中間体、それらの製法、及び除草剤 |
| PT75510A PT75510B (en) | 1981-09-16 | 1982-09-06 | Process for the preparation of substituted phenylsulfonylurea derivatives having an herbicidal effect |
| AT82108192T ATE20884T1 (de) | 1981-09-16 | 1982-09-06 | Substituierte phenylsulfonylharnstoffderivate, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide. |
| EP82108192A EP0074595B1 (de) | 1981-09-16 | 1982-09-06 | Substituierte Phenylsulfonylharnstoff- Derivate, Verfahren und neue Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE8282108192T DE3272147D1 (en) | 1981-09-16 | 1982-09-06 | Substituted phenylsulfonyl urea derivatives, process and intermediates for their preparation, and their use as herbicides |
| US06/415,629 US4474600A (en) | 1981-09-16 | 1982-09-07 | Herbicidally active novel substituted phenylsulfonylurea derivatives |
| PH27837A PH18858A (en) | 1981-09-16 | 1982-09-08 | Herbicidally active novel substituted phenyl-sulfonylurea derivatives and intermediates therefor |
| IL66779A IL66779A (en) | 1981-09-16 | 1982-09-13 | Pyrimidine(triazine)substituted phenylsulfonylurea derivatives,their preparation and their use as herbicides |
| NZ201892A NZ201892A (en) | 1981-09-16 | 1982-09-13 | Heterocyclic benzenesulphonylureas:and herbicidal compositions |
| DD82243236A DD204201A5 (de) | 1981-09-16 | 1982-09-14 | Herbizide mittel |
| AU88374/82A AU8837482A (en) | 1981-09-16 | 1982-09-14 | Heterocyclic substituted phenylsulfonylurea derivatives |
| TR21759A TR21759A (tr) | 1981-09-16 | 1982-09-14 | Suebstituee edilmis fenilsuelfoniluere tuerevleri,bunlarin meydana getirilmesine mahsus usul ve herbisid olarak kullanimlari ve bunlarin meydana getirilmesine mahsus yeni ara ueruenler |
| GR69267A GR77338B (en, 2012) | 1981-09-16 | 1982-09-14 | |
| BR8205407A BR8205407A (pt) | 1981-09-16 | 1982-09-15 | Processo para a preparacao de derivados substituidos de fenilsulfonilureias composicoes herbicidas processos para o combate do crescimento indesejado de plantas e para a preparacao de composicoes |
| HU822934A HU188806B (en) | 1981-09-16 | 1982-09-15 | Herbicidal preparations containing phenyl-sulfonyl-urea derivatives as active substance and process for the production of the active substances |
| ZA826755A ZA826755B (en) | 1981-09-16 | 1982-09-15 | Substituted phenylsulfonylurea derivatives,a process for their preparation and their use as herbicides,and new intermediate products for their preparation |
| CA 411420 CA1225407C (en) | 1981-09-16 | 1982-09-15 | Substituted phenylsulfonylurea derivatives, a process for their preparation and their use as herbicides, and new intermediate products for their preparation |
| PL1982238231A PL135593B1 (en) | 1981-09-16 | 1982-09-15 | Herbicide and method of obtaining a new substituted derivatives of phenylsulfonylurea |
| DK412782A DK412782A (da) | 1981-09-16 | 1982-09-15 | Substituerede phenylurinstofderivater, deres fremstilling og mellemprodukter hertil samt deres anvendelse som herbicider |
| ES515724A ES515724A0 (es) | 1981-09-16 | 1982-09-15 | Procedimiento para la obtencion de derivados de fenilsulfonil-urea sustituidas. |
| CS826669A CS229691B2 (en) | 1981-09-16 | 1982-09-16 | Herbicide agent and manufacturing process of effective substances |
| US06/561,610 US4545944A (en) | 1981-09-16 | 1983-12-14 | Herbicidally active novel substituted phenylsulfonylurea derivatives and intermediates therefor |
| CA000483271A CA1225407A (en) | 1981-09-16 | 1985-06-05 | Substituted phenylsulfonylurea derivatives, a process for their preparation and their use as herbicides, and new intermediate products for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56144590A JPS5846071A (ja) | 1981-09-16 | 1981-09-16 | 置換フエニルスルホニルウレア誘導体、その中間体、それらの製法、及び除草剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5846071A true JPS5846071A (ja) | 1983-03-17 |
Family
ID=15365615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56144590A Pending JPS5846071A (ja) | 1981-09-16 | 1981-09-16 | 置換フエニルスルホニルウレア誘導体、その中間体、それらの製法、及び除草剤 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4474600A (en, 2012) |
| EP (1) | EP0074595B1 (en, 2012) |
| JP (1) | JPS5846071A (en, 2012) |
| AT (1) | ATE20884T1 (en, 2012) |
| AU (1) | AU8837482A (en, 2012) |
| BR (1) | BR8205407A (en, 2012) |
| CA (2) | CA1225407C (en, 2012) |
| CS (1) | CS229691B2 (en, 2012) |
| DD (1) | DD204201A5 (en, 2012) |
| DE (1) | DE3272147D1 (en, 2012) |
| DK (1) | DK412782A (en, 2012) |
| ES (1) | ES515724A0 (en, 2012) |
| GR (1) | GR77338B (en, 2012) |
| HU (1) | HU188806B (en, 2012) |
| IL (1) | IL66779A (en, 2012) |
| NZ (1) | NZ201892A (en, 2012) |
| PH (1) | PH18858A (en, 2012) |
| PL (1) | PL135593B1 (en, 2012) |
| PT (1) | PT75510B (en, 2012) |
| TR (1) | TR21759A (en, 2012) |
| ZA (1) | ZA826755B (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58146572A (ja) * | 1982-01-25 | 1983-09-01 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Ｎ−フエニルスルホニル−ｎ′−ピリミジニル−および−ｎ′−トリアジニル尿素、その製造方法ならびに該化合物を含有する除草および植物生長抑制剤 |
| JPS62201326A (ja) * | 1986-02-28 | 1987-09-05 | Canon Inc | 測光装置 |
| US11807796B2 (en) | 2016-12-09 | 2023-11-07 | Daikin Industries, Ltd. | Heat transport device and heat transport method using same |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR21378A (tr) * | 1981-01-26 | 1984-04-26 | Nihon Tokushu Noyaku Seizo Kk | Yeni substit*e fenilsulfonil*re t*revleri,bunlarin ihzarina mahsus bir usul ve yeni ara maddeler ve bunlarin herbisidler olarak kullanimi |
| BR8302396A (pt) * | 1982-05-12 | 1984-01-10 | Du Pont | Composto;composicao e processo adequados para controlar o crescimento de vegetacao indesejada |
| JPS606654A (ja) * | 1983-06-24 | 1985-01-14 | Nippon Tokushu Noyaku Seizo Kk | 置換フエニルスルホニルグアニジン誘導体、その中間体、それらの製法及び除草剤 |
| JPS6036467A (ja) * | 1983-08-10 | 1985-02-25 | Nippon Tokushu Noyaku Seizo Kk | 置換フエニルスルホニルグアニジン誘導体、その中間体、それらの製法及び雑草防除剤 |
| DE3330602A1 (de) * | 1983-08-25 | 1985-03-21 | Hoechst Ag, 6230 Frankfurt | Neue pyrazolyl- und isoxazolylsulfonylharnstoffe |
| US4602936A (en) * | 1983-09-09 | 1986-07-29 | Ciba-Geigy Corporation | Herbicidal sulfonylureas |
| EP0151554A1 (de) * | 1984-02-03 | 1985-08-14 | Ciba-Geigy Ag | Neue Phenylsulfonamidderivate |
| US4514213A (en) * | 1984-03-19 | 1985-04-30 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4602942A (en) * | 1984-03-19 | 1986-07-29 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4643761A (en) * | 1985-01-28 | 1987-02-17 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US6075166A (en) * | 1995-03-31 | 2000-06-13 | Smithkline Beecham Corporation | Photolytically cleavable encoding and linking agents for use in combinatorial chemistry |
| CN102464611B (zh) * | 2010-11-03 | 2014-01-01 | 中国中化股份有限公司 | 一种取代的联芳香基苯磺酰胺类化合物与用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3280184A (en) * | 1960-07-08 | 1966-10-18 | Minnesota Mining & Mfg | Bis-sulfonylisocyanates |
| FR1468747A (fr) * | 1965-07-19 | 1967-02-10 | Benzène-sulfonyl-1 (pyrimidyl-2)-3 urées | |
| US3484466A (en) * | 1966-09-30 | 1969-12-16 | Upjohn Co | Preparation of aromatic sulfonyl isocyanates |
| OA05625A (fr) * | 1976-04-07 | 1981-04-30 | Du Pont | N-(hétérocyclique aminocarbonyl) aryl sulfonamides herbicides, compositions les contenant et procédés les utilisant . |
| US4169719A (en) * | 1976-04-07 | 1979-10-02 | E. I. Du Pont De Nemours And Co. | Herbicidal sulfonamides |
| US4191553A (en) * | 1978-03-02 | 1980-03-04 | E. I. Du Pont De Nemours And Company | Herbicidal sulfamates |
| US4452628A (en) * | 1979-07-26 | 1984-06-05 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4339267A (en) * | 1980-01-18 | 1982-07-13 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4368067A (en) * | 1980-04-29 | 1983-01-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4378991A (en) * | 1980-07-11 | 1983-04-05 | E. I. Du Pont De Nemours And Company | Herbicidal o-aryl or alkarylsulfonylureas |
| BR8107546A (pt) * | 1980-11-25 | 1982-08-17 | Du Pont | Composto de 3-amino-2-alquenilimidatos e processo para preparar o composto |
| TR21378A (tr) * | 1981-01-26 | 1984-04-26 | Nihon Tokushu Noyaku Seizo Kk | Yeni substit*e fenilsulfonil*re t*revleri,bunlarin ihzarina mahsus bir usul ve yeni ara maddeler ve bunlarin herbisidler olarak kullanimi |
-
1981
- 1981-09-16 JP JP56144590A patent/JPS5846071A/ja active Pending
-
1982
- 1982-09-06 AT AT82108192T patent/ATE20884T1/de active
- 1982-09-06 DE DE8282108192T patent/DE3272147D1/de not_active Expired
- 1982-09-06 EP EP82108192A patent/EP0074595B1/de not_active Expired
- 1982-09-06 PT PT75510A patent/PT75510B/pt unknown
- 1982-09-07 US US06/415,629 patent/US4474600A/en not_active Expired - Fee Related
- 1982-09-08 PH PH27837A patent/PH18858A/en unknown
- 1982-09-13 IL IL66779A patent/IL66779A/xx unknown
- 1982-09-13 NZ NZ201892A patent/NZ201892A/xx unknown
- 1982-09-14 TR TR21759A patent/TR21759A/xx unknown
- 1982-09-14 AU AU88374/82A patent/AU8837482A/en not_active Abandoned
- 1982-09-14 DD DD82243236A patent/DD204201A5/de unknown
- 1982-09-14 GR GR69267A patent/GR77338B/el unknown
- 1982-09-15 DK DK412782A patent/DK412782A/da not_active Application Discontinuation
- 1982-09-15 CA CA 411420 patent/CA1225407C/en not_active Expired
- 1982-09-15 ZA ZA826755A patent/ZA826755B/xx unknown
- 1982-09-15 HU HU822934A patent/HU188806B/hu unknown
- 1982-09-15 PL PL1982238231A patent/PL135593B1/pl unknown
- 1982-09-15 BR BR8205407A patent/BR8205407A/pt unknown
- 1982-09-15 ES ES515724A patent/ES515724A0/es active Granted
- 1982-09-16 CS CS826669A patent/CS229691B2/cs unknown
-
1983
- 1983-12-14 US US06/561,610 patent/US4545944A/en not_active Expired - Fee Related
-
1985
- 1985-06-05 CA CA000483271A patent/CA1225407A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58146572A (ja) * | 1982-01-25 | 1983-09-01 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Ｎ−フエニルスルホニル−ｎ′−ピリミジニル−および−ｎ′−トリアジニル尿素、その製造方法ならびに該化合物を含有する除草および植物生長抑制剤 |
| JPS62201326A (ja) * | 1986-02-28 | 1987-09-05 | Canon Inc | 測光装置 |
| US11807796B2 (en) | 2016-12-09 | 2023-11-07 | Daikin Industries, Ltd. | Heat transport device and heat transport method using same |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8403444A1 (es) | 1984-03-16 |
| PL238231A1 (en) | 1984-04-24 |
| HU188806B (en) | 1986-05-28 |
| ES515724A0 (es) | 1984-03-16 |
| ATE20884T1 (de) | 1986-08-15 |
| PH18858A (en) | 1985-10-21 |
| EP0074595B1 (de) | 1986-07-23 |
| ZA826755B (en) | 1983-08-31 |
| TR21759A (tr) | 1985-06-06 |
| DK412782A (da) | 1983-03-17 |
| DE3272147D1 (en) | 1986-08-28 |
| US4474600A (en) | 1984-10-02 |
| PT75510B (en) | 1984-12-04 |
| IL66779A (en) | 1985-12-31 |
| CS229691B2 (en) | 1984-06-18 |
| US4545944A (en) | 1985-10-08 |
| BR8205407A (pt) | 1983-08-23 |
| PT75510A (en) | 1982-10-01 |
| NZ201892A (en) | 1985-04-30 |
| PL135593B1 (en) | 1985-11-30 |
| DD204201A5 (de) | 1983-11-23 |
| IL66779A0 (en) | 1982-12-31 |
| CA1225407A (en) | 1987-08-11 |
| GR77338B (en, 2012) | 1984-09-11 |
| CA1225407C (en) | 1987-08-11 |
| EP0074595A1 (de) | 1983-03-23 |
| AU8837482A (en) | 1983-03-24 |
| US4474600B1 (en, 2012) | 1986-11-04 |
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