JPH0543706B2 - - Google Patents
Info
- Publication number
- JPH0543706B2 JPH0543706B2 JP57228261A JP22826182A JPH0543706B2 JP H0543706 B2 JPH0543706 B2 JP H0543706B2 JP 57228261 A JP57228261 A JP 57228261A JP 22826182 A JP22826182 A JP 22826182A JP H0543706 B2 JPH0543706 B2 JP H0543706B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- compound
- formula
- methyl
- lower alkyl
- 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 - Lifetime
Links
- 239000004009 herbicide Substances 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- VMFDZAIIYSKZDE-UHFFFAOYSA-N 1h-pyrazol-5-ylsulfonylurea Chemical class NC(=O)NS(=O)(=O)C=1C=CNN=1 VMFDZAIIYSKZDE-UHFFFAOYSA-N 0.000 claims description 2
- 150000005005 aminopyrimidines Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims description 2
- YSZJWGGYDOPMDX-UHFFFAOYSA-N 1h-pyrazole;sulfonylurea Chemical class C=1C=NNC=1.NC(=O)N=S(=O)=O YSZJWGGYDOPMDX-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 47
- 239000000203 mixture Substances 0.000 description 34
- 239000003795 chemical substances by application Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000008187 granular material Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000003945 anionic surfactant Substances 0.000 description 8
- 230000000887 hydrating effect Effects 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- LSJVQKDTVCDSPE-UHFFFAOYSA-N 1h-pyrazole-5-sulfonamide Chemical compound NS(=O)(=O)C=1C=CNN=1 LSJVQKDTVCDSPE-UHFFFAOYSA-N 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 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 6
- 239000000047 product Substances 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 5
- 239000000440 bentonite Substances 0.000 description 5
- 229910000278 bentonite Inorganic materials 0.000 description 5
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 150000003918 triazines Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- -1 alkyl chlorocarbonate Chemical compound 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000004033 plastic 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
- 238000010298 pulverizing process Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- HWCIJXQWUOZFBW-UHFFFAOYSA-N 1H-pyrazole sulfuryl diisocyanate Chemical class S(=O)(=O)(N=C=O)N=C=O.N1N=CC=C1 HWCIJXQWUOZFBW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YRDRWAMQGRODTB-UHFFFAOYSA-N CCOC(=O)C=1C=NN(C)C=1S Chemical compound CCOC(=O)C=1C=NN(C)C=1S YRDRWAMQGRODTB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 3
- CMKZUAZQUJEAQU-UHFFFAOYSA-N 1h-pyrrol-2-ylsulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CN1 CMKZUAZQUJEAQU-UHFFFAOYSA-N 0.000 description 2
- SDYOVMHXYNKROV-UHFFFAOYSA-N 5-chloro-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=CC(C(O)=O)=C1Cl SDYOVMHXYNKROV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000301850 Cupressus sempervirens Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ICDLJCWXRUNUNO-UHFFFAOYSA-N ethyl 1-methyl-5-sulfamoylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1S(N)(=O)=O ICDLJCWXRUNUNO-UHFFFAOYSA-N 0.000 description 2
- UOKDEVVNDSYMRY-UHFFFAOYSA-N ethyl 5-chloro-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1Cl UOKDEVVNDSYMRY-UHFFFAOYSA-N 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 1
- SNWZXTZIZWBIDQ-UHFFFAOYSA-N 4-methoxy-6-methylpyrimidin-2-amine Chemical compound COC1=CC(C)=NC(N)=N1 SNWZXTZIZWBIDQ-UHFFFAOYSA-N 0.000 description 1
- 244000296825 Amygdalus nana Species 0.000 description 1
- 235000003840 Amygdalus nana Nutrition 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- SRMHVGZFDOFMKW-UHFFFAOYSA-N COC(=O)c1cnn(C)c1O Chemical compound COC(=O)c1cnn(C)c1O SRMHVGZFDOFMKW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 240000006766 Cornus mas Species 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241001517923 Douglasiidae Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 235000011432 Prunus Nutrition 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 241000681978 Rhododendron japonicum Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- YKENTGBQCDMCNF-UHFFFAOYSA-N ethyl 2-methyl-3-oxo-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C1=CNN(C)C1=O YKENTGBQCDMCNF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- UCEGAOBNUZGIPC-UHFFFAOYSA-N isocyanic acid;triazine Chemical compound N=C=O.C1=CN=NN=C1 UCEGAOBNUZGIPC-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UNWLBZTZCSGYIE-UHFFFAOYSA-N methyl 1-methyl-5-sulfamoylpyrazole-4-carboxylate Chemical compound COC(=O)C=1C=NN(C)C=1S(N)(=O)=O UNWLBZTZCSGYIE-UHFFFAOYSA-N 0.000 description 1
- GXCHZTZQQJQKAN-UHFFFAOYSA-N methyl 5-chloro-1-methylpyrazole-4-carboxylate Chemical compound COC(=O)C=1C=NN(C)C=1Cl GXCHZTZQQJQKAN-UHFFFAOYSA-N 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- FMLHTZVGNSACKP-UHFFFAOYSA-N pyridin-2-ylsulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=N1 FMLHTZVGNSACKP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- UWLSBCQQMWCJFY-UHFFFAOYSA-N pyridine;sulfonylurea Chemical class C1=CC=NC=C1.NC(=O)N=S(=O)=O UWLSBCQQMWCJFY-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22826182A JPS59122488A (ja) | 1982-12-28 | 1982-12-28 | ピラゾ−ルスルホニルウレア誘導体、その製法および該誘導体を含有する除草剤 |
| CA 422309 CA1340326C (en) | 1982-02-27 | 1983-02-24 | Pyrazolesulfonylurea derivative, preparation therof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof |
| MYPI87003208A MY100991A (en) | 1982-02-27 | 1987-12-16 | Pyrazolesulfonylurea derivative, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22826182A JPS59122488A (ja) | 1982-12-28 | 1982-12-28 | ピラゾ−ルスルホニルウレア誘導体、その製法および該誘導体を含有する除草剤 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3889986A Division JPS61210003A (ja) | 1986-02-24 | 1986-02-24 | 除草剤 |
| JP3889886A Division JPS61210084A (ja) | 1986-02-24 | 1986-02-24 | ピラゾールスルホニルウレア誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59122488A JPS59122488A (ja) | 1984-07-14 |
| JPH0543706B2 true JPH0543706B2 (ko) | 1993-07-02 |
Family
ID=16873695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22826182A Granted JPS59122488A (ja) | 1982-02-27 | 1982-12-28 | ピラゾ−ルスルホニルウレア誘導体、その製法および該誘導体を含有する除草剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59122488A (ko) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4917719A (en) * | 1983-03-30 | 1990-04-17 | E. I. Du Pont De Nemours And Company | Herbicidal isothiazole derivatives |
| JPH0660175B2 (ja) * | 1983-08-24 | 1994-08-10 | 日産化学工業株式会社 | ピラゾ−ルスルホニルウレア誘導体，その製法および該誘導体を含有する選択性除草剤 |
| JPH0660176B2 (ja) * | 1984-03-22 | 1994-08-10 | 日産化学工業株式会社 | ピラゾールスルホニルウレア誘導体、製法および選択性除草剤 |
| US4792565A (en) * | 1986-04-24 | 1988-12-20 | Mitsui Toatsu Chemicals, Inc. | Pyrazolecarbonylamine derivatives and agricultural and horticultural fungicides containing said compounds |
| JPH0193503A (ja) * | 1987-01-21 | 1989-04-12 | Kumiai Chem Ind Co Ltd | 除草剤組成物 |
| AU606496B2 (en) * | 1988-01-26 | 1991-02-07 | Schering Aktiengesellschaft | Benfuresate mixtures |
| US5480993A (en) * | 1993-03-05 | 1996-01-02 | Lucky Ltd. | Process for preparation of sulfonylurea derivatives and intermediates for the process and process for preparing the same |
| US6087500A (en) * | 1996-05-16 | 2000-07-11 | Nissan Chemical Industries, Ltd. | Methods for producing pyrimidine compounds |
| CN102524278A (zh) * | 2011-12-13 | 2012-07-04 | 济南科赛基农化工有限公司 | 水稻田用恶嗪草酮、吡嘧磺隆、丙草胺三元泡腾除草剂及其制备方法 |
| CN112441978B (zh) * | 2019-08-29 | 2022-04-26 | 江西天宇化工有限公司 | 一种1-甲基-5-羟基吡唑-4-羧酸乙酯的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS591480A (ja) * | 1982-06-01 | 1984-01-06 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | イミダゾール又はピラゾール誘導体 |
-
1982
- 1982-12-28 JP JP22826182A patent/JPS59122488A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS591480A (ja) * | 1982-06-01 | 1984-01-06 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | イミダゾール又はピラゾール誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59122488A (ja) | 1984-07-14 |
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