FI92829B - N-fenyl-5-alkoxi-1,2,4-triazolo/1,5-c/pyrimidin-2-sulfonamider och herbicidicala kompositionera därav - Google Patents
N-fenyl-5-alkoxi-1,2,4-triazolo/1,5-c/pyrimidin-2-sulfonamider och herbicidicala kompositionera därav Download PDFInfo
- Publication number
- FI92829B FI92829B FI900371A FI900371A FI92829B FI 92829 B FI92829 B FI 92829B FI 900371 A FI900371 A FI 900371A FI 900371 A FI900371 A FI 900371A FI 92829 B FI92829 B FI 92829B
- Authority
- FI
- Finland
- Prior art keywords
- pyrimidine
- triazolo
- compound
- compounds
- formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 61
- 230000002363 herbicidal effect Effects 0.000 title claims description 21
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical class NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 118
- -1 pyrimidine-2-sulfonamide compound Chemical class 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000004009 herbicide Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- NYXSWZYOVPCNCV-UHFFFAOYSA-N 7-chloro-5-ethoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride Chemical compound CCOC1=NC(Cl)=CC2=NC(S(Cl)(=O)=O)=NN12 NYXSWZYOVPCNCV-UHFFFAOYSA-N 0.000 claims description 2
- QOJVMWWQQCLLLO-UHFFFAOYSA-N 7-chloro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride Chemical compound COC1=NC(Cl)=CC2=NC(S(Cl)(=O)=O)=NN12 QOJVMWWQQCLLLO-UHFFFAOYSA-N 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 230000035784 germination Effects 0.000 claims description 2
- RWCWOLSSRGJBML-UHFFFAOYSA-N 5,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride Chemical compound COC1=NC(OC)=CC2=NC(S(Cl)(=O)=O)=NN21 RWCWOLSSRGJBML-UHFFFAOYSA-N 0.000 claims 1
- AMTMFUMHIYECPO-UHFFFAOYSA-N 7-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride Chemical compound COC1=NC(F)=CC2=NC(S(Cl)(=O)=O)=NN12 AMTMFUMHIYECPO-UHFFFAOYSA-N 0.000 claims 1
- DZSDPRWWVPGCMZ-UHFFFAOYSA-N 8-chloro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride Chemical compound COC1=NC=C(Cl)C2=NC(S(Cl)(=O)=O)=NN12 DZSDPRWWVPGCMZ-UHFFFAOYSA-N 0.000 claims 1
- LBYADLCRAJSDQT-UHFFFAOYSA-N 8-chloro-n-(2,6-difluorophenyl)-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide Chemical compound N=1N2C(OC)=NC=C(Cl)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F LBYADLCRAJSDQT-UHFFFAOYSA-N 0.000 claims 1
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 claims 1
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 claims 1
- YCAVTTFYAOQYCZ-UHFFFAOYSA-N n-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide Chemical compound N=1N2C(OC)=NC(OC)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl YCAVTTFYAOQYCZ-UHFFFAOYSA-N 0.000 claims 1
- CULAGHAXBSYDOC-UHFFFAOYSA-N pyrimidine-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=NC=CC=N1 CULAGHAXBSYDOC-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 239000000843 powder Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000003039 volatile agent Substances 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 6
- 229940073608 benzyl chloride Drugs 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000002211 ultraviolet spectrum Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YBKJYRSLZWQJNE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide Chemical class C1=CN=CN2N=C(S(=O)(=O)N)N=C21 YBKJYRSLZWQJNE-UHFFFAOYSA-N 0.000 description 3
- QEWBHMFBUSIJLS-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride Chemical compound C1=CN=CN2N=C(S(=O)(=O)Cl)N=C21 QEWBHMFBUSIJLS-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BMAYBAYAYKTUDB-UHFFFAOYSA-N 2-benzylsulfanyl-5-chloro-7-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N=1N2C(Cl)=NC(OC)=CC2=NC=1SCC1=CC=CC=C1 BMAYBAYAYKTUDB-UHFFFAOYSA-N 0.000 description 2
- UXIVAUKRKDVKFR-UHFFFAOYSA-N 2-benzylsulfanyl-7-fluoro-5-methylsulfanyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N=1N2C(SC)=NC(F)=CC2=NC=1SCC1=CC=CC=C1 UXIVAUKRKDVKFR-UHFFFAOYSA-N 0.000 description 2
- YLFFPQUVEAYUCL-UHFFFAOYSA-N 2-benzylsulfanyl-8-chloro-7-methoxy-5-methyl-[1,2,4]triazolo[1,5-c]pyrimidine Chemical compound N1=C2C(Cl)=C(OC)N=C(C)N2N=C1SCC1=CC=CC=C1 YLFFPQUVEAYUCL-UHFFFAOYSA-N 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000003403 Limnocharis flava Nutrition 0.000 description 2
- 239000002202 Polyethylene glycol Chemical class 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000019764 Soybean Meal Nutrition 0.000 description 2
- 241000692569 Stylephorus chordatus Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- QLOWGDIISXJREF-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine Chemical class C1=CN=CN2N=CN=C21 QLOWGDIISXJREF-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001804 chlorine Chemical group 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229920001223 polyethylene glycol Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical class NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 description 2
- QIEQDFYXVYQLLU-UHFFFAOYSA-N pyrimidin-4-ylhydrazine Chemical class NNC1=CC=NC=N1 QIEQDFYXVYQLLU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000004455 soybean meal Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- AHMAKFIBYJTQAW-UHFFFAOYSA-N (2-methylsulfanylpyrimidin-4-yl)hydrazine Chemical compound CSC1=NC=CC(NN)=N1 AHMAKFIBYJTQAW-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- VLCPQJBTYLSJFR-UHFFFAOYSA-N (5-chloro-2-methylsulfanylpyrimidin-4-yl)hydrazine Chemical compound CSC1=NC=C(Cl)C(NN)=N1 VLCPQJBTYLSJFR-UHFFFAOYSA-N 0.000 description 1
- ICCQVWLLVLDWFC-UHFFFAOYSA-N (5-chloro-6-methoxy-2-methylpyrimidin-4-yl)hydrazine Chemical compound COC1=NC(C)=NC(NN)=C1Cl ICCQVWLLVLDWFC-UHFFFAOYSA-N 0.000 description 1
- HJTQAJRNALYEMJ-UHFFFAOYSA-N (6-bromo-2-methylsulfanylpyrimidin-4-yl)hydrazine Chemical compound CSC1=NC(Br)=CC(NN)=N1 HJTQAJRNALYEMJ-UHFFFAOYSA-N 0.000 description 1
- YYJMUTXAMSZWMQ-UHFFFAOYSA-N (6-fluoro-2-methylsulfanylpyrimidin-4-yl)hydrazine Chemical compound CSC1=NC(F)=CC(NN)=N1 YYJMUTXAMSZWMQ-UHFFFAOYSA-N 0.000 description 1
- IICQWDJYVKCOTB-UHFFFAOYSA-N (6-methyl-2-methylsulfanylpyrimidin-4-yl)hydrazine Chemical compound CSC1=NC(C)=CC(NN)=N1 IICQWDJYVKCOTB-UHFFFAOYSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
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- 150000003230 pyrimidines Chemical class 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XQOLMNXEGDTGML-UHFFFAOYSA-N triazolo[1,5-c]pyrimidine Chemical compound C1=NC=CC2=CN=NN21 XQOLMNXEGDTGML-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (19)
1. N-fenyl-5-alkoxi-l,2,4-triazolo[1,5-c]pyrimidin-2-sulfonamidförening med formeln 5 N I—I A)—(J (I) B D vari X betecknar OCH3 eller OC2H5; Y och Z är oberoende av varandra OCH3/ OC2H5, H, CH3,
2. Förening enligt patentkrav 1, vilken är N-(2,6-diklor-3-metylfenyl) -5,7-dimetoxi-l, 2,4-triazolo [ 1,5-c] -pyrimidin-2-sulfonamid.
3. Förening enligt patentkrav 1, vilken är N-(2- 25 metoxikarbonyl-6-fluorfenyl) -7-klor-5-xnetoxi-l, 2,4-triazo- lo[1,5-c]pyrimidin-2-sulfonamid.
4. Förening enligt patentkrav l, vilken är N-(2-metoxikarbonyl-6-klorfenyl)-7-fluor-5-etoxi-l,2,4-triazo-lo[l,5-c]pyrimidin-2-sulfonamid. ;· 30
5. Förening enligt patentkrav 1, vilken är N-(2- • klor-6-fluorfenyl)-5-etoxi-7-fluor-1,2,4-triazolo[1,5-c]- pyrimidin-2-sulfonamid.
6. Förening enligt patentkrav 1, vilken är N-(2,6-diklorfenyl)-7-fluor-5-etoxi-l,2,4-triazolo[1,5-c]pyrimi-35 din-2-sulfonamid. 92829 Do
7. Förening enligt patentkrav 1, vilken är N-(2,6-difluorfenyl)-8-fluor-5-metoxi-l,2,4-triazolo[1,5-c]pyri-midin-2-sulfonamid.
8. Förening enligt patentkrav 1, vilken Mr N-(2,6- 5 dif luorfenyl)-8-klor-5-metoxi-l, 2,4-triazolo[ 1,5-c]pyrimi- din-2-sulfonamid.
9. Förening enligt patentkrav 1, vilken Mr N-(2-metoxikarbonyl-6-f luorfenyl) -8-klor-5-metoxi-l, 2,4-triazo-lo[1,5-c]pyrimidin-2-sulfonamid.
10. Herbicidal komposition, kMnneteck- n a d dMrav, att den omfattar en agrikulturellt godtagbar hjMlpsubstans eller en bMrare och en herbicidalt effektiv mMngd av en l,2,4-triazolo[l,5-c]pyrimidin-2-sulfonamidfö-rening enligt nägot av patentkraven 1-9. 15
11. Förfarande för regiering av oönskad vegetation, kMnnetecknat dMrav, att pM vMxterna eller pä vMxtplatsen appliceras en herbicidalt effektiv mMngd av en herbicidal komposition enligt patentkrav 10.
12. Förfarande enligt patentkrav 11, k M n n e - 20 tecknat dMrav, att den herbicidala kompositionen appliceras före grodden i en mMngd av 0,01 - 10 kg den aktiva bestandsdelen/ha.
13. Förfarande enligt patentkrav 11, kMnnetecknat dMrav, att den herbicidala kompositionen 25 appliceras efter grodden i en mMngd av 0,001 - 10 kg den aktiva beständsdelen/ha.
14. 5-alkoxi-l,2,4-triazolo[1,5-c]pyrimidin-2-sul-fonylkloridförening med formeln (II), vilken Mr anvMndbar som utgängsmaterial vid framstMllning av föreningar med 30 formeln (I) X -N ,ΧΑΑο1, Z 92829 väri X betecknar Cl, OCH3 eller OC2H5; och Y och Z är oberoende av varandra OCH3, OC2H5, H, CH3, Cl, Br eller F. 5 15. Förening enligt patentkrav 14, vilken är 2- klorsulfonyl-5,7-dimetoxi-l,2,4-triazolo[1,5-c]pyrimidin.
15 Cl, Br eller F; A är F, Cl, Br, C02(C,-C3)alkyl, CF3 eller N02; B betecknar H, CH3, F, Cl, Br eller OCH3; D och J betecknar vardera H eller CH3 förutsatt att ätminstone nägondera av D och J betecknar H; 20 och agrikulturellt godtagbara salter därav.
16. Förening enligt patentkrav 14, vilken är 7- klor-2-klorsulfonyl-5-metoxi-l,2,4-triazolo[l,5-c]pyrimi-din. 10
17. Förening enligt patentkrav 14, vilken är 2- klorsulfonyl-7-fluor-5-metoxi-l, 2,4-triazolo[ 1,5-c]pyrimi-din.
18. Förening enligt patentkrav 14, vilken är 7- klor-2-klorsulfonyl-5-etoxi-l, 2,4-triazolo [ 1,5-c] pyrimi- 15 din.
19. Förening enligt patentkrav 14, vilken är 8- klor-2-klorsulfonyl-5-metoxi-l,2,4-triazolo[l,5-c]pyrimi-din. m » 1 i «
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19827888A | 1988-05-25 | 1988-05-25 | |
| US19827888 | 1988-05-25 | ||
| US07/347,601 US5010195A (en) | 1988-05-25 | 1989-05-03 | Herbicidal alkoxy-1,2,4-triazolo(1,5-c)primidine-2-sulfonamides |
| US34760189 | 1989-05-03 | ||
| PCT/US1989/002286 WO1989011782A1 (en) | 1988-05-25 | 1989-05-25 | ALKOXY-1,2,4-TRIAZOLO[1,5-c]PYRIMIDINE-2-SULFONAMIDES, PROCESS FOR THEIR PREPARATION AND INTERMEDIATES |
| US8902286 | 1989-05-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI900371A0 FI900371A0 (sv) | 1990-01-24 |
| FI92829B true FI92829B (sv) | 1994-09-30 |
| FI92829C FI92829C (sv) | 1995-01-10 |
Family
ID=26893624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI900371A FI92829C (sv) | 1988-05-25 | 1990-01-24 | N-fenyl-5-alkoxi-1,2,4-triazolo/1,5-c/pyrimidin-2-sulfonamider och herbicidicala kompositionera därav |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5010195A (sv) |
| EP (1) | EP0343752B1 (sv) |
| JP (1) | JP2598540B2 (sv) |
| KR (1) | KR0123876B1 (sv) |
| CN (2) | CN1030606C (sv) |
| AR (1) | AR247209A1 (sv) |
| AU (1) | AU616519B2 (sv) |
| BR (1) | BR8906993A (sv) |
| CA (1) | CA1331180C (sv) |
| DE (1) | DE68911033T2 (sv) |
| DK (1) | DK174982B1 (sv) |
| ES (1) | ES2059704T3 (sv) |
| FI (1) | FI92829C (sv) |
| HU (1) | HU206212B (sv) |
| IL (1) | IL90365A0 (sv) |
| MY (1) | MY106285A (sv) |
| NZ (1) | NZ229200A (sv) |
| UA (1) | UA26989A1 (sv) |
| WO (1) | WO1989011782A1 (sv) |
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| FR2678618B1 (fr) * | 1991-07-05 | 1993-11-05 | Upsa Laboratoires | Nouveaux derives de triazolo pyrimidine antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| US5201938A (en) * | 1991-07-19 | 1993-04-13 | Dowelanco | N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides |
| US5177206A (en) * | 1991-10-08 | 1993-01-05 | Dowelanco | Process for the preparation of substituted N-(aryl)-1,2,4-triazolopyrimidine-2-sulfonamides |
| US5155221A (en) * | 1992-03-06 | 1992-10-13 | Dowelanco | Process for the preparation of 2-alkylthio-4-hydrazino-5-fluoropyrimidines |
| US5356789A (en) * | 1993-05-28 | 1994-10-18 | American Cyanamid Company | Methods for detecting acetohydroxyacid synthase inhibitors |
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| US5552546A (en) * | 1994-07-28 | 1996-09-03 | Dowelanco | Process for the preparation of 2-ethoxy-4,6-dihydroxypyrimidine |
| WO1997008172A1 (en) * | 1995-08-31 | 1997-03-06 | Dowelanco | N-(1-ethyl-4-pyrazolyl)triazoloazinesulfonamide herbicides |
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| CN106674132B (zh) * | 2016-11-22 | 2019-04-26 | 上海书亚医药科技有限公司 | 一种嘧啶类除草剂的制备方法与应用 |
| CN106905323B (zh) * | 2017-02-27 | 2019-02-19 | 江苏省农用激素工程技术研究中心有限公司 | 双氯磺草胺的制备方法 |
| JP6911143B2 (ja) | 2018-11-07 | 2021-07-28 | 福建永晶科技股▲ふん▼有限公司Ｆｕｊｉａｎ Ｙｏｎｇｊｉｎｇ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ | ピラゾール又はピリミジノンの新しい製造方法 |
| CN111217817B (zh) * | 2020-02-26 | 2022-06-10 | 山东潍坊润丰化工股份有限公司 | 一种三唑并嘧啶类除草剂的制备方法 |
| GB2610805A (en) | 2021-09-03 | 2023-03-22 | Rotam Agrochem Int Co Ltd | Novel crystalline form of florasulam, preparation and use of the same |
| WO2023222836A1 (en) | 2022-05-20 | 2023-11-23 | Syngenta Crop Protection Ag | Herbicidal compositions |
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| GB951652A (en) * | 1960-06-28 | 1964-03-11 | Wallace Broadbent | Sulphamyl triazolopyrimidines and their preparation |
| US4036840A (en) * | 1972-06-07 | 1977-07-19 | Icn Pharmaceuticals | 2-Substituted-s-triazolo[1,5a]pyrimidines |
| US4349378A (en) * | 1978-07-25 | 1982-09-14 | Fbc Limited | Compounds useful as pesticides |
| US4528288A (en) * | 1983-05-02 | 1985-07-09 | Riker Laboratories, Inc. | Substituted triazolo[1,5-c]pyrimidines |
| DE19775042I2 (de) * | 1983-11-14 | 2001-05-03 | Dowelanco | 1, 2, 4-Triazolo 1, 4-a pyrimidin-2-Sulfonamide und zubereitungen und Methode zur Bekaempfung unerwuenschter Pflanzen und die Nitrierung von Ammonium-Stickstoff im Boden |
| GR80916B (en) * | 1983-11-14 | 1985-03-12 | Dow Chemical Co | Method of preparing 1,2,4-triazolo (1,5-a)-pyrimidine-2-sulfonyl chlorides |
| CA1244826A (en) * | 1984-01-26 | 1988-11-15 | William A. Kleschick | Sulfonamides derived from substituted 2-amino-1,2,4- triazolo(1,5-a)-pyrimidines and compositions and methods of controlling undesired vegetation |
| US4605433A (en) * | 1985-05-30 | 1986-08-12 | The Dow Chemical Company | 1,2,4-triazolo[1,5-a]-1,3,5-triazine-2-sulfonamides and compositions and methods of controlling undesired vegetation |
| GB8610531D0 (en) * | 1986-04-30 | 1986-06-04 | Fbc Ltd | Herbicides |
| GB8610532D0 (en) * | 1986-04-30 | 1986-06-04 | Fbc Ltd | Herbicides |
| EP0244948A3 (en) * | 1986-04-30 | 1989-03-15 | Schering Agrochemicals Limited | Triazolopyrimidine herbicides |
| US4734123A (en) * | 1986-05-06 | 1988-03-29 | The Dow Chemical Company | Novel sulfonamides and method of making |
| DE3627411A1 (de) * | 1986-08-13 | 1988-02-18 | Bayer Ag | Triazolo-pyrimidin-2-sulfonamide |
| DE3640155A1 (de) * | 1986-11-25 | 1988-05-26 | Bayer Ag | Triazolo-pyrimidin-2-sulfonamide |
| US4731446A (en) * | 1987-05-01 | 1988-03-15 | The Dow Chemical Company | Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides |
| US4921527A (en) * | 1987-07-31 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4910306A (en) * | 1987-11-09 | 1990-03-20 | The Dow Chemical Company | Preparation of substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonanilides |
| DE3812350A1 (de) * | 1988-04-14 | 1989-10-26 | Bayer Ag | Triazoloazine |
| US4904301A (en) * | 1988-04-19 | 1990-02-27 | The Dow Chemical Company | 5-Fluoromethyl-1,2,4-triazolo(1,5-A)-pyrimidines |
| US4959473A (en) * | 1988-04-19 | 1990-09-25 | The Dow Chemical Company | 7-ethoxy-5-fluoromethyl-1,2,4-triazole[1,5-a]-pyrimidine-2-sulfonamindes |
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| EP0378508B1 (de) * | 1989-01-11 | 1995-03-01 | Ciba-Geigy Ag | Antidots zur Verbesserung der Kulturpflanzenvertäglichkeit agrochemischer Wirkstoffe |
-
1989
- 1989-05-03 US US07/347,601 patent/US5010195A/en not_active Expired - Lifetime
- 1989-05-19 NZ NZ229200A patent/NZ229200A/xx unknown
- 1989-05-22 IL IL90365A patent/IL90365A0/xx unknown
- 1989-05-23 AR AR89313991A patent/AR247209A1/es active
- 1989-05-24 DE DE89201326T patent/DE68911033T2/de not_active Expired - Lifetime
- 1989-05-24 CN CN89103624A patent/CN1030606C/zh not_active Expired - Lifetime
- 1989-05-24 EP EP89201326A patent/EP0343752B1/en not_active Expired - Lifetime
- 1989-05-24 CA CA000600483A patent/CA1331180C/en not_active Expired - Lifetime
- 1989-05-24 MY MYPI89000699A patent/MY106285A/en unknown
- 1989-05-24 CN CN93116973A patent/CN1037605C/zh not_active Expired - Lifetime
- 1989-05-24 ES ES89201326T patent/ES2059704T3/es not_active Expired - Lifetime
- 1989-05-25 JP JP1506836A patent/JP2598540B2/ja not_active Expired - Lifetime
- 1989-05-25 AU AU35208/89A patent/AU616519B2/en not_active Expired
- 1989-05-25 WO PCT/US1989/002286 patent/WO1989011782A1/en not_active Ceased
- 1989-05-25 UA UA5001117A patent/UA26989A1/uk unknown
- 1989-05-25 KR KR1019900700131A patent/KR0123876B1/ko not_active Expired - Lifetime
- 1989-05-25 HU HU894025A patent/HU206212B/hu unknown
- 1989-05-25 BR BR898906993A patent/BR8906993A/pt not_active Application Discontinuation
-
1990
- 1990-01-24 FI FI900371A patent/FI92829C/sv not_active IP Right Cessation
- 1990-01-25 DK DK199000206A patent/DK174982B1/da not_active IP Right Cessation
-
1991
- 1991-08-13 US US07/744,149 patent/US5163995A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BR8906993A (pt) | 1990-12-18 |
| US5010195A (en) | 1991-04-23 |
| KR900701786A (ko) | 1990-12-04 |
| KR0123876B1 (ko) | 1997-11-20 |
| DK20690A (da) | 1990-01-25 |
| DE68911033D1 (de) | 1994-01-13 |
| AU616519B2 (en) | 1991-10-31 |
| JPH03501129A (ja) | 1991-03-14 |
| FI92829C (sv) | 1995-01-10 |
| US5163995A (en) | 1992-11-17 |
| IL90365A0 (en) | 1989-12-15 |
| CN1039590A (zh) | 1990-02-14 |
| CN1037605C (zh) | 1998-03-04 |
| NZ229200A (en) | 1993-01-27 |
| AR247209A1 (es) | 1994-11-30 |
| ES2059704T3 (es) | 1994-11-16 |
| AU3520889A (en) | 1989-11-30 |
| HU894025D0 (en) | 1990-11-28 |
| JP2598540B2 (ja) | 1997-04-09 |
| WO1989011782A1 (en) | 1989-12-14 |
| EP0343752B1 (en) | 1993-12-01 |
| DK174982B1 (da) | 2004-04-05 |
| HUT53907A (en) | 1990-12-28 |
| MY106285A (en) | 1995-04-29 |
| DE68911033T2 (de) | 1994-03-31 |
| UA26989A1 (uk) | 2000-02-28 |
| EP0343752A1 (en) | 1989-11-29 |
| CN1106010A (zh) | 1995-08-02 |
| CN1030606C (zh) | 1996-01-03 |
| HU206212B (en) | 1992-09-28 |
| DK20690D0 (da) | 1990-01-25 |
| FI900371A0 (sv) | 1990-01-24 |
| CA1331180C (en) | 1994-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Patent granted |
Owner name: THE DOW CHEMICAL COMPANY |
|
| MA | Patent expired |