SK85096A3 - Fluoropropylthiazoline derivatives and herbicides - Google Patents
Fluoropropylthiazoline derivatives and herbicides Download PDFInfo
- Publication number
- SK85096A3 SK85096A3 SK850-96A SK85096A SK85096A3 SK 85096 A3 SK85096 A3 SK 85096A3 SK 85096 A SK85096 A SK 85096A SK 85096 A3 SK85096 A3 SK 85096A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- compound
- fluoropropylthiazoline
- reaction
- mmol
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 18
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims description 60
- 241000196324 Embryophyta Species 0.000 claims description 18
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 14
- 235000021536 Sugar beet Nutrition 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- -1 metal alkoxides Chemical class 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- ZUCNQLCQHOGZNO-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-thiazol-2-yl)-3-fluoropropan-2-imine Chemical compound FCC(=N)CC1=NCCS1 ZUCNQLCQHOGZNO-UHFFFAOYSA-N 0.000 description 12
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 12
- CGXLVFVQLHINFO-UHFFFAOYSA-N 3-(3-fluoropropyl)-1,3-thiazol-2-imine Chemical compound FCCCN1C=CSC1=N CGXLVFVQLHINFO-UHFFFAOYSA-N 0.000 description 12
- YFKGQFATEDYTPI-UHFFFAOYSA-N 4,6-dimethoxy-1h-triazin-2-amine Chemical compound COC1=CC(OC)=NN(N)N1 YFKGQFATEDYTPI-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 150000007530 organic bases Chemical class 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 235000007320 Avena fatua Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 7
- 240000008620 Fagopyrum esculentum Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 7
- 150000008282 halocarbons Chemical class 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 150000003918 triazines Chemical class 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- ZYHSBLCLXCOGBP-UHFFFAOYSA-N 3-(3-fluoropropyl)-1,3-thiazol-2-imine;hydrobromide Chemical compound Br.FCCCN1C=CSC1=N ZYHSBLCLXCOGBP-UHFFFAOYSA-N 0.000 description 6
- 241000219198 Brassica Species 0.000 description 6
- 235000003351 Brassica cretica Nutrition 0.000 description 6
- 235000003343 Brassica rupestris Nutrition 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000003945 anionic surfactant Substances 0.000 description 6
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 235000010460 mustard Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 6
- 238000002791 soaking Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 240000001592 Amaranthus caudatus Species 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 241000258957 Asteroidea Species 0.000 description 5
- 241000209764 Avena fatua Species 0.000 description 5
- 244000098338 Triticum aestivum Species 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 4
- 235000004535 Avena sterilis Nutrition 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 244000245600 Persicaria longiseta Species 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000004178 amaranth Substances 0.000 description 4
- 235000012735 amaranth Nutrition 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ZIBYVLURVCHISB-UHFFFAOYSA-N (4,6-dimethoxy-1H-triazin-2-yl)urea Chemical compound COC1=NN(NC(=C1)OC)NC(=O)N ZIBYVLURVCHISB-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 244000281762 Chenopodium ambrosioides Species 0.000 description 2
- 241000132536 Cirsium Species 0.000 description 2
- 235000005422 Distichlis palmeri Nutrition 0.000 description 2
- 244000077283 Distichlis palmeri Species 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001502129 Mullus Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241000251555 Tunicata Species 0.000 description 2
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WGBSTIRRHNSMRN-UHFFFAOYSA-N n-tert-butylsulfamoyl chloride Chemical compound CC(C)(C)NS(Cl)(=O)=O WGBSTIRRHNSMRN-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- KBZORIBFGMIGOT-UHFFFAOYSA-N phenyl n-chlorosulfonylcarbamate Chemical compound ClS(=O)(=O)NC(=O)OC1=CC=CC=C1 KBZORIBFGMIGOT-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZAONJNQXCRQBQZ-UHFFFAOYSA-N 1-bromo-1-fluoropropane Chemical compound CCC(F)Br ZAONJNQXCRQBQZ-UHFFFAOYSA-N 0.000 description 1
- DRZFUQLDKMBBIV-UHFFFAOYSA-N 2-(3-fluoropropyl)-4,5-dihydro-1,3-thiazole Chemical compound FCCCC1=NCCS1 DRZFUQLDKMBBIV-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 235000005474 African couch grass Nutrition 0.000 description 1
- 241000189415 Alopecurus aequalis Species 0.000 description 1
- 241000219317 Amaranthaceae Species 0.000 description 1
- 241000561739 Amaranthus blitum subsp. oleraceus Species 0.000 description 1
- 235000013478 Amaranthus oleraceus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 244000055702 Amaranthus viridis Species 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000217444 Calystegia Species 0.000 description 1
- 241000220244 Capsella <angiosperm> Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000219321 Caryophyllaceae Species 0.000 description 1
- 244000277285 Cassia obtusifolia Species 0.000 description 1
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 235000009731 Chenopodium ficifolium Nutrition 0.000 description 1
- 244000035395 Chenopodium ficifolium Species 0.000 description 1
- 241000233839 Commelina communis Species 0.000 description 1
- 241000233833 Commelinaceae Species 0.000 description 1
- 241000207782 Convolvulaceae Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 235000016854 Cyperus rotundus Nutrition 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 240000003176 Digitaria ciliaris Species 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 241000305599 Erigeron annuus Species 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- 241001599881 Euphorbia maculata Species 0.000 description 1
- 241000221017 Euphorbiaceae Species 0.000 description 1
- 241001520106 Eustachys Species 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 241001289540 Fallopia convolvulus Species 0.000 description 1
- 235000016622 Filipendula ulmaria Nutrition 0.000 description 1
- 244000061544 Filipendula vulgaris Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 241001077837 Galinsoga quadriradiata Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000060234 Gmelina philippensis Species 0.000 description 1
- 235000017335 Hordeum vulgare subsp spontaneum Nutrition 0.000 description 1
- 241001299819 Hordeum vulgare subsp. spontaneum Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 241000442132 Lactarius lactarius Species 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241000207923 Lamiaceae Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 235000009193 Lamium purpureum Nutrition 0.000 description 1
- 240000006503 Lamium purpureum Species 0.000 description 1
- 241000219071 Malvaceae Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241001148659 Panicum dichotomiflorum Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 240000000697 Pinguicula vulgaris Species 0.000 description 1
- 235000004262 Pinguicula vulgaris Nutrition 0.000 description 1
- 241000219050 Polygonaceae Species 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000219304 Portulacaceae Species 0.000 description 1
- 235000008484 Rorippa indica Nutrition 0.000 description 1
- 240000004053 Rorippa indica Species 0.000 description 1
- 241001153838 Rubia argyi Species 0.000 description 1
- 241001107098 Rubiaceae Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000251778 Squalus acanthias Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- 241000052209 Triplasis Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000990144 Veronica persica Species 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 241000394440 Viola arvensis Species 0.000 description 1
- 241001106476 Violaceae Species 0.000 description 1
- 244000067505 Xanthium strumarium Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP104794 | 1994-01-11 | ||
| JP6310585A JPH07242665A (ja) | 1994-01-11 | 1994-12-14 | フルオロプロピルチアゾリン誘導体及び除草剤 |
| PCT/JP1995/000011 WO1995018806A1 (fr) | 1994-01-11 | 1995-01-10 | Derive de fluoropropylthiazoline et herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK85096A3 true SK85096A3 (en) | 1997-02-05 |
Family
ID=26334205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK850-96A SK85096A3 (en) | 1994-01-11 | 1995-01-10 | Fluoropropylthiazoline derivatives and herbicides |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5763365A (ja) |
| EP (1) | EP0739893A1 (ja) |
| JP (1) | JPH07242665A (ja) |
| CN (2) | CN1037349C (ja) |
| BG (1) | BG100697A (ja) |
| CZ (1) | CZ205296A3 (ja) |
| HU (1) | HU214648B (ja) |
| SK (1) | SK85096A3 (ja) |
| WO (1) | WO1995018806A1 (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997000250A1 (fr) * | 1995-06-15 | 1997-01-03 | Nissan Chemical Industries, Ltd. | Procede pour preparer la 3-(3-fluoropropyl)-2-iminothiazoline |
| WO1997038581A1 (en) * | 1996-04-16 | 1997-10-23 | E.I. Du Pont De Nemours And Company | Herbicidal mixtures |
| US20030212116A1 (en) * | 1999-12-28 | 2003-11-13 | Toshio Niki | Heterocyclic imino compounds and fungicides and insecticides for agricultural and horitcultural use |
| MXPA03000793A (es) * | 2000-07-28 | 2003-06-04 | Henkel Kgaa | Enzima amilolitica novedosa, extraida de bacilo sp a 7-7 (dsm 12368) y agentes de lavado y limpiadores que contienen esta enzima amilolitica novedosa. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0596109B1 (en) * | 1990-03-06 | 1996-12-18 | Nissan Chemical Industries, Limited | Sulfamidosulfonamide derivatives and herbicides |
| JP3208773B2 (ja) * | 1991-06-28 | 2001-09-17 | 日産化学工業株式会社 | イミノスルホニルウレア誘導体及び除草剤 |
| ES2123044T3 (es) * | 1991-06-28 | 1999-01-01 | Nissan Chemical Ind Ltd | Derivado de iminosulfonilurea y herbicida. |
-
1994
- 1994-12-14 JP JP6310585A patent/JPH07242665A/ja active Pending
-
1995
- 1995-01-10 CZ CZ962052A patent/CZ205296A3/cs unknown
- 1995-01-10 EP EP95905234A patent/EP0739893A1/en not_active Ceased
- 1995-01-10 CN CN95191163A patent/CN1037349C/zh not_active Expired - Fee Related
- 1995-01-10 WO PCT/JP1995/000011 patent/WO1995018806A1/ja not_active Application Discontinuation
- 1995-01-10 HU HU9601871A patent/HU214648B/hu not_active IP Right Cessation
- 1995-01-10 SK SK850-96A patent/SK85096A3/sk unknown
- 1995-01-10 US US08/669,380 patent/US5763365A/en not_active Expired - Fee Related
-
1996
- 1996-07-05 BG BG100697A patent/BG100697A/xx unknown
-
1997
- 1997-06-16 CN CN97112763.8A patent/CN1208037A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1037349C (zh) | 1998-02-11 |
| HU214648B (hu) | 1998-04-28 |
| EP0739893A4 (ja) | 1996-11-20 |
| CN1208037A (zh) | 1999-02-17 |
| WO1995018806A1 (fr) | 1995-07-13 |
| HU9601871D0 (en) | 1996-09-30 |
| HUT74889A (en) | 1997-02-28 |
| CN1138331A (zh) | 1996-12-18 |
| EP0739893A1 (en) | 1996-10-30 |
| JPH07242665A (ja) | 1995-09-19 |
| US5763365A (en) | 1998-06-09 |
| CZ205296A3 (en) | 1996-10-16 |
| BG100697A (en) | 1997-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100203826B1 (ko) | 우라실 유도체 | |
| US4744814A (en) | N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-trifluoromethylpyridine-2-sulfonamide or salts thereof, herbicidal composition containing the same | |
| JPH0228159A (ja) | 複素環式２―アルコキシフエノキシスルホニル尿素類、それらの製造方法およびそれらを含有する除草剤 | |
| CZ280644B6 (cs) | Herbicidní prostředek | |
| EP0103537A2 (de) | N-Arylsulfonyl-N'-triazolylharnstoffe | |
| JPH0245473A (ja) | 置換スルホニルジアミド、それらの製造方法およびそれらの除草剤および植物生長調整剤としての用途 | |
| NZ199547A (en) | Heterocyclic substituted phenylsulphonyl ureas and herbicidal compositions | |
| JPH0421672B2 (ja) | ||
| SK85096A3 (en) | Fluoropropylthiazoline derivatives and herbicides | |
| US3999974A (en) | Barbituric acid derivatives | |
| JP3208773B2 (ja) | イミノスルホニルウレア誘導体及び除草剤 | |
| DE3105453A1 (de) | Phenyl- bzw. phenoxysulfonyl-pyrimidyl-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchstumsregulatoren | |
| EP0493321A1 (de) | Pyrimidinyl- und Triazinyl-salicylamide sowie deren Verwendung und Herstellung | |
| EP0596109B1 (en) | Sulfamidosulfonamide derivatives and herbicides | |
| EP0268295B1 (de) | N-Arylsulfonyl-N'-pyrimidyl-(triazinyl)-harnstoffe | |
| US4790869A (en) | Sulfonamide compounds and salts thereof, herbicidal compositions containing them | |
| US5376620A (en) | Sulfonamide derivative, process for preparing the same and herbicide using the same | |
| CA2042355C (en) | Sulfamidosulfonylurea derivatives and herbicides | |
| JP2000128713A (ja) | 除草剤組成物 | |
| DE3431918A1 (de) | Substituierte arylsulfonylguanidine | |
| US5116405A (en) | Pyridinesulfonamide derivatives and herbicides | |
| AU622322B2 (en) | Pyridazinone derivatives and compositions for controlling and/or preventing insect pests | |
| RU2109011C1 (ru) | Производные иминосульфонилмочевины, способ уничтожения или подавления сорняков | |
| US5464808A (en) | 1-[α-cyclopropyl-α-(substituted oxy)-o-tolyl]sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal agents | |
| JPH0525173A (ja) | 縮合ピリミジンジオン誘導体および除草剤 |