JPS6160070B2 - - Google Patents

Info

Publication number

JPS6160070B2

JPS6160070B2 JP22583582A JP22583582A JPS6160070B2 JP S6160070 B2 JPS6160070 B2 JP S6160070B2 JP 22583582 A JP22583582 A JP 22583582A JP 22583582 A JP22583582 A JP 22583582A JP S6160070 B2 JPS6160070 B2 JP S6160070B2

Authority

JP

Japan

Prior art keywords

methyl

yloxyacetic acid

benzoxazol

compound

formula

Prior art date

1982-12-24

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

Links

• Espacenet
• Global Dossier
• Discuss

• 238000004519 manufacturing process Methods 0.000 claims description 8
• HTSCXQQAODEVDH-UHFFFAOYSA-N (4,6-dimethoxy-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(NC(N)=O)=NC(OC)=N1 HTSCXQQAODEVDH-UHFFFAOYSA-N 0.000 claims description 4
• CEZUTXKTYBCXLP-UHFFFAOYSA-N n-(oxomethylidene)-2-phenylbenzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 CEZUTXKTYBCXLP-UHFFFAOYSA-N 0.000 claims description 4
• KVHFZZUPCXCRIX-UHFFFAOYSA-N 4,6-dimethoxy-1,3,5-triazin-2-amine Chemical compound COC1=NC(N)=NC(OC)=N1 KVHFZZUPCXCRIX-UHFFFAOYSA-N 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 34
• 241000196324 Embryophyta Species 0.000 description 27
• FWYULLXZQPHSAL-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yloxy)acetic acid Chemical compound C1=CC=C2OC(OCC(=O)O)=NC2=C1 FWYULLXZQPHSAL-UHFFFAOYSA-N 0.000 description 26
• OPQIOIYLAKHILI-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yloxy)acetic acid Chemical compound C1=CC=C2SC(OCC(=O)O)=NC2=C1 OPQIOIYLAKHILI-UHFFFAOYSA-N 0.000 description 19
• -1 1,3,5-triazine -2-yl Chemical group 0.000 description 17
• 239000000203 mixture Substances 0.000 description 15
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• 229910052739 hydrogen Inorganic materials 0.000 description 14
• 239000001257 hydrogen Substances 0.000 description 14
• 230000002363 herbicidal effect Effects 0.000 description 13
• 150000002431 hydrogen Chemical class 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 238000000034 method Methods 0.000 description 10
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• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
• GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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• 239000004009 herbicide Substances 0.000 description 5
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
• 235000009566 rice Nutrition 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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• 125000004432 carbon atom Chemical group C* 0.000 description 4
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• 239000000945 filler Substances 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
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• 239000003381 stabilizer Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
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• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• 239000008096 xylene Substances 0.000 description 4
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 238000006243 chemical reaction Methods 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
• 238000011156 evaluation Methods 0.000 description 3
• 230000009931 harmful effect Effects 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 239000000575 pesticide Substances 0.000 description 3
• 239000003208 petroleum Substances 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
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 description 2
• SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
• 244000056139 Brassica cretica Species 0.000 description 2
• 235000003351 Brassica cretica Nutrition 0.000 description 2
• 235000003343 Brassica rupestris Nutrition 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
• 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
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• 231100000674 Phytotoxicity Toxicity 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 239000000853 adhesive Substances 0.000 description 2
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• 125000003545 alkoxy group Chemical group 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
• 230000015572 biosynthetic process Effects 0.000 description 2
• QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
• 150000004657 carbamic acid derivatives Chemical class 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
• 235000021240 caseins Nutrition 0.000 description 2
• 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 2
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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• FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
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• HWIPDQZKMXAATL-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yloxy)-n-phenyl-n-propan-2-ylacetamide Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C(C)C)C1=CC=CC=C1 HWIPDQZKMXAATL-UHFFFAOYSA-N 0.000 description 1
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• XRMYDVOOPVERPA-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yloxy)-n-cyclohexyl-n-methylacetamide Chemical compound N=1C2=CC=CC=C2OC=1OCC(=O)N(C)C1CCCCC1 XRMYDVOOPVERPA-UHFFFAOYSA-N 0.000 description 1
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• HJAJCUOMYGWPHW-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yloxy)-n-phenyl-n-propan-2-ylacetamide Chemical compound N=1C2=CC=CC=C2OC=1OCC(=O)N(C(C)C)C1=CC=CC=C1 HJAJCUOMYGWPHW-UHFFFAOYSA-N 0.000 description 1
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