JPH0152389B2 - - Google Patents
Info
- Publication number
- JPH0152389B2 JPH0152389B2 JP21497186A JP21497186A JPH0152389B2 JP H0152389 B2 JPH0152389 B2 JP H0152389B2 JP 21497186 A JP21497186 A JP 21497186A JP 21497186 A JP21497186 A JP 21497186A JP H0152389 B2 JPH0152389 B2 JP H0152389B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- aminocarbonyl
- compounds
- nitrophenyl
- reaction
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 241000196324 Embryophyta Species 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- -1 Substituted -pyrimidinylsulfonyl Chemical group 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- 239000008187 granular material Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 11
- 240000007594 Oryza sativa Species 0.000 description 11
- 235000007164 Oryza sativa Nutrition 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 241000209140 Triticum Species 0.000 description 11
- 235000021307 Triticum Nutrition 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 235000009566 rice Nutrition 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229940124530 sulfonamide Drugs 0.000 description 8
- 150000003456 sulfonamides Chemical class 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- 229960000892 attapulgite Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229910052625 palygorskite Inorganic materials 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 244000062793 Sorghum vulgare Species 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 5
- 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 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- HTAXOAKNMIFKSU-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[(2-nitrophenyl)methylsulfonyl]urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)[N+]([O-])=O)=N1 HTAXOAKNMIFKSU-UHFFFAOYSA-N 0.000 description 4
- 240000006995 Abutilon theophrasti Species 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 241000209764 Avena fatua Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 244000201986 Cassia tora Species 0.000 description 3
- 235000014552 Cassia tora Nutrition 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 235000017896 Digitaria Nutrition 0.000 description 3
- 241001303487 Digitaria <clam> Species 0.000 description 3
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 3
- 240000003176 Digitaria ciliaris Species 0.000 description 3
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 3
- 235000005476 Digitaria cruciata Nutrition 0.000 description 3
- 235000006830 Digitaria didactyla Nutrition 0.000 description 3
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 235000014716 Eleusine indica Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 description 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- ICRCGYUJMWBKJQ-UHFFFAOYSA-N (2-methylsulfonylphenyl)methanesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1CS(N)(=O)=O ICRCGYUJMWBKJQ-UHFFFAOYSA-N 0.000 description 2
- ISTVKPVROGPHTI-UHFFFAOYSA-N (2-methylsulfonylphenyl)methanesulfonyl chloride Chemical compound CS(=O)(=O)C1=CC=CC=C1CS(Cl)(=O)=O ISTVKPVROGPHTI-UHFFFAOYSA-N 0.000 description 2
- HHHPBOLNRBDDIN-UHFFFAOYSA-N (2-methylsulfonylphenyl)methyl carbamimidothioate;hydrobromide Chemical compound Br.CS(=O)(=O)C1=CC=CC=C1CSC(N)=N HHHPBOLNRBDDIN-UHFFFAOYSA-N 0.000 description 2
- SNCFSWRNEADGAI-UHFFFAOYSA-N (2-nitrophenyl)methanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1[N+]([O-])=O SNCFSWRNEADGAI-UHFFFAOYSA-N 0.000 description 2
- FUEFNUGYRWQHTH-UHFFFAOYSA-N (2-nitrophenyl)methanesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1CS(Cl)(=O)=O FUEFNUGYRWQHTH-UHFFFAOYSA-N 0.000 description 2
- UOMAUCLXHRHFRD-UHFFFAOYSA-N (2-nitrophenyl)methyl carbamimidothioate;hydrochloride Chemical compound Cl.NC(=N)SCC1=CC=CC=C1[N+]([O-])=O UOMAUCLXHRHFRD-UHFFFAOYSA-N 0.000 description 2
- LKUSKRMVUBLXDH-UHFFFAOYSA-N 1-(2-methylsulfonylphenyl)-n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1CS(=O)(=O)N=C=O LKUSKRMVUBLXDH-UHFFFAOYSA-N 0.000 description 2
- SDQPJVPIWHFCES-UHFFFAOYSA-N 1-(2-nitrophenyl)-n-(oxomethylidene)ethanesulfonamide Chemical compound O=C=NS(=O)(=O)C(C)C1=CC=CC=C1[N+]([O-])=O SDQPJVPIWHFCES-UHFFFAOYSA-N 0.000 description 2
- JRSRXSLMRDOUBE-UHFFFAOYSA-N 1-(2-nitrophenyl)-n-(oxomethylidene)methanesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1CS(=O)(=O)N=C=O JRSRXSLMRDOUBE-UHFFFAOYSA-N 0.000 description 2
- ILVLQAASRSQQDM-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanesulfonamide Chemical compound NS(=O)(=O)C(C)C1=CC=CC=C1[N+]([O-])=O ILVLQAASRSQQDM-UHFFFAOYSA-N 0.000 description 2
- OGRHYKRDIGQZIR-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanesulfonyl chloride Chemical compound ClS(=O)(=O)C(C)C1=CC=CC=C1[N+]([O-])=O OGRHYKRDIGQZIR-UHFFFAOYSA-N 0.000 description 2
- OOXBILMPVRVXOC-UHFFFAOYSA-N 1-(2-nitrophenyl)ethyl carbamimidothioate;hydrobromide Chemical compound Br.NC(=N)SC(C)C1=CC=CC=C1[N+]([O-])=O OOXBILMPVRVXOC-UHFFFAOYSA-N 0.000 description 2
- QWRBSNOOIBLILY-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-(2-nitrophenyl)ethylsulfonyl]urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C(C)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 QWRBSNOOIBLILY-UHFFFAOYSA-N 0.000 description 2
- NYOVEYKGZYLOPT-UHFFFAOYSA-N 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-[(2-nitrophenyl)methylsulfonyl]urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)[N+]([O-])=O)=N1 NYOVEYKGZYLOPT-UHFFFAOYSA-N 0.000 description 2
- XSEZQSLGRZXPKV-UHFFFAOYSA-N 1-(4-methoxy-6-methylpyrimidin-2-yl)-3-[(2-nitrophenyl)methylsulfonyl]urea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)[N+]([O-])=O)=N1 XSEZQSLGRZXPKV-UHFFFAOYSA-N 0.000 description 2
- BGNSUIXBZRGZOV-UHFFFAOYSA-N 1-butyl-3-[(2-methylsulfonylphenyl)methylsulfonyl]urea Chemical compound CCCCNC(=O)NS(=O)(=O)CC1=CC=CC=C1S(C)(=O)=O BGNSUIXBZRGZOV-UHFFFAOYSA-N 0.000 description 2
- LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007563 Barbarea vulgaris Nutrition 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241000209202 Bromus secalinus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000016854 Cyperus rotundus Nutrition 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000110847 Kochia Species 0.000 description 2
- 235000003403 Limnocharis flava Nutrition 0.000 description 2
- 244000100545 Lolium multiflorum Species 0.000 description 2
- 241001268782 Paspalum dilatatum Species 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 241001355178 Setaria faberi Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 244000061457 Solanum nigrum Species 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- 241001506766 Xanthium Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- SOUGLODYPBMACB-UHFFFAOYSA-N butane;hydrate Chemical compound O.CCCC SOUGLODYPBMACB-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000005243 fluidization Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20363880A | 1980-11-03 | 1980-11-03 | |
| US203638 | 1980-11-03 | ||
| US306212 | 1981-09-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62103059A JPS62103059A (ja) | 1987-05-13 |
| JPH0152389B2 true JPH0152389B2 (fr) | 1989-11-08 |
Family
ID=22754736
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56174697A Granted JPS57112379A (en) | 1980-11-03 | 1981-11-02 | Herbicidal sulfonamides |
| JP21497186A Granted JPS62103059A (ja) | 1980-11-03 | 1986-09-11 | ベンゼンメタンスルホニルイソシアネ−ト類 |
| JP21497086A Granted JPS62116567A (ja) | 1980-11-03 | 1986-09-11 | ベンジルスルホニル尿素類及びその利用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56174697A Granted JPS57112379A (en) | 1980-11-03 | 1981-11-02 | Herbicidal sulfonamides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21497086A Granted JPS62116567A (ja) | 1980-11-03 | 1986-09-11 | ベンジルスルホニル尿素類及びその利用 |
Country Status (1)
| Country | Link |
|---|---|
| JP (3) | JPS57112379A (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02131412A (ja) * | 1982-11-04 | 1990-05-21 | E I Du Pont De Nemours & Co | 水稲用複合除草剤 |
| JPS5982306A (ja) * | 1982-11-04 | 1984-05-12 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | 水田雑草除草方法 |
| DD238318A5 (de) * | 1984-08-30 | 1986-08-20 | Bayer Ag,De | Herbizide mittel |
| JPS6187670A (ja) * | 1984-10-05 | 1986-05-06 | S D S Baiotetsuku:Kk | スルホニルアセトアミド誘導体及び除草剤 |
| JPH0655650B2 (ja) * | 1984-11-06 | 1994-07-27 | 三共株式会社 | 除草剤組成物 |
| JPS63179806A (ja) * | 1987-01-21 | 1988-07-23 | Kumiai Chem Ind Co Ltd | 除草剤組成物 |
| JP2546200B2 (ja) * | 1991-02-20 | 1996-10-23 | 東ソー株式会社 | 田植前湛水下水田除草用水性懸濁製剤および散布方法 |
| JPH04308605A (ja) * | 1991-04-08 | 1992-10-30 | Sumitomo Metal Ind Ltd | 銅導体ペースト |
| JP3270819B2 (ja) * | 1997-02-13 | 2002-04-02 | 北興化学工業株式会社 | 湛水下水田の直接散布用水性懸濁製剤 |
| JP3270825B2 (ja) * | 1997-02-14 | 2002-04-02 | 北興化学工業株式会社 | 湛水下水田の直接散布用水性懸濁製剤 |
-
1981
- 1981-11-02 JP JP56174697A patent/JPS57112379A/ja active Granted
-
1986
- 1986-09-11 JP JP21497186A patent/JPS62103059A/ja active Granted
- 1986-09-11 JP JP21497086A patent/JPS62116567A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62116567A (ja) | 1987-05-28 |
| JPS57112379A (en) | 1982-07-13 |
| JPS62103059A (ja) | 1987-05-13 |
| JPS6251954B2 (fr) | 1987-11-02 |
| JPS626705B2 (fr) | 1987-02-13 |
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