NO862137L - Nye sulfonamider med herbicid virkning. - Google Patents
Nye sulfonamider med herbicid virkning.Info
- Publication number
- NO862137L NO862137L NO862137A NO862137A NO862137L NO 862137 L NO862137 L NO 862137L NO 862137 A NO862137 A NO 862137A NO 862137 A NO862137 A NO 862137A NO 862137 L NO862137 L NO 862137L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- och3
- methyl
- tetrazol
- alkoxy
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title abstract description 10
- 230000000694 effects Effects 0.000 title abstract description 5
- 239000004009 herbicide Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- -1 Sulfonamide compounds Chemical class 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- NGQNPXOYTXCDRK-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(1-methyltetrazol-5-yl)phenyl]sulfonylurea Chemical group COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C=2N(N=NN=2)C)=N1 NGQNPXOYTXCDRK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- NEQJDWDGWRFLLB-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(1-ethyltetrazol-5-yl)phenyl]sulfonylurea Chemical group CCN1N=NN=C1C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NEQJDWDGWRFLLB-UHFFFAOYSA-N 0.000 claims description 2
- PWRVPHGIZXNDGT-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(5-methyltetrazol-1-yl)phenyl]sulfonylurea Chemical group COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)N2C(=NN=N2)C)=N1 PWRVPHGIZXNDGT-UHFFFAOYSA-N 0.000 claims description 2
- OQRSGIQLGCIVOB-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-methyl-6-(1-methyltetrazol-5-yl)phenyl]sulfonylurea Chemical group COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C=2N(N=NN=2)C)=N1 OQRSGIQLGCIVOB-UHFFFAOYSA-N 0.000 claims description 2
- OAPUSXSTWFGBEJ-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-3-[2-(1-methyltetrazol-5-yl)phenyl]sulfonylurea Chemical group CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C=2N(N=NN=2)C)=N1 OAPUSXSTWFGBEJ-UHFFFAOYSA-N 0.000 claims description 2
- CPZVXDVNLGECTI-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-3-[2-methyl-6-(1-methyltetrazol-5-yl)phenyl]sulfonylurea Chemical group CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C=2N(N=NN=2)C)=N1 CPZVXDVNLGECTI-UHFFFAOYSA-N 0.000 claims description 2
- OUEXWLVAGUGRSD-UHFFFAOYSA-N 1-(4-chloro-6-methoxypyrimidin-2-yl)-3-[2-(1-ethyltetrazol-5-yl)phenyl]sulfonylurea Chemical group CCN1N=NN=C1C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 OUEXWLVAGUGRSD-UHFFFAOYSA-N 0.000 claims description 2
- GOYYTHAPASAXAC-UHFFFAOYSA-N 1-(4-chloro-6-methoxypyrimidin-2-yl)-3-[2-(1-methyltetrazol-5-yl)phenyl]sulfonylurea Chemical group COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C=2N(N=NN=2)C)=N1 GOYYTHAPASAXAC-UHFFFAOYSA-N 0.000 claims description 2
- HYIYISQXUGIMDT-UHFFFAOYSA-N 1-(4-methoxy-6-methylpyrimidin-2-yl)-3-[2-(1-methyltetrazol-5-yl)phenyl]sulfonylurea Chemical group COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C=2N(N=NN=2)C)=N1 HYIYISQXUGIMDT-UHFFFAOYSA-N 0.000 claims description 2
- BDDYTHKZNAPVFB-UHFFFAOYSA-N 1-(4-methoxy-6-methylpyrimidin-2-yl)-3-[2-methyl-6-(1-methyltetrazol-5-yl)phenyl]sulfonylurea Chemical group COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C=2N(N=NN=2)C)=N1 BDDYTHKZNAPVFB-UHFFFAOYSA-N 0.000 claims description 2
- 229940100389 Sulfonylurea Drugs 0.000 claims description 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006519 CCH3 Chemical group 0.000 claims 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 abstract description 6
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 abstract description 5
- 230000008635 plant growth Effects 0.000 abstract description 4
- HFOWWBNMJUVIMH-UHFFFAOYSA-N sulfuryl diisothiocyanate Chemical compound S=C=NS(=O)(=O)N=C=S HFOWWBNMJUVIMH-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 239000000203 mixture Substances 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 31
- 238000000034 method Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 18
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000008187 granular material Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 11
- 230000035784 germination Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 150000003536 tetrazoles Chemical group 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- ACUVVGHNVWGEIG-UHFFFAOYSA-N 2-(5-methyltetrazol-1-yl)benzenesulfonamide Chemical compound CC1=NN=NN1C1=CC=CC=C1S(N)(=O)=O ACUVVGHNVWGEIG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 150000003918 triazines Chemical group 0.000 description 4
- KJPBIIYLHXZOSB-UHFFFAOYSA-N 2-(2-methyltetrazol-5-yl)benzenesulfonamide Chemical compound CN1N=NC(C=2C(=CC=CC=2)S(N)(=O)=O)=N1 KJPBIIYLHXZOSB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 3
- 235000003097 Artemisia absinthium Nutrition 0.000 description 3
- 240000001851 Artemisia dracunculus Species 0.000 description 3
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 3
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 244000075634 Cyperus rotundus Species 0.000 description 3
- 235000016854 Cyperus rotundus Nutrition 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 241001355178 Setaria faberi Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000001138 artemisia absinthium Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000008331 benzenesulfonamides Chemical class 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
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- 239000012265 solid product Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
- FUCAOINCGJBFPX-UHFFFAOYSA-N 2-(1-methyltetrazol-5-yl)benzenesulfonamide Chemical compound CN1N=NN=C1C1=CC=CC=C1S(N)(=O)=O FUCAOINCGJBFPX-UHFFFAOYSA-N 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000209761 Avena Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 244000277285 Cassia obtusifolia Species 0.000 description 2
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 2
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- 244000058871 Echinochloa crus-galli Species 0.000 description 2
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- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 244000009660 Sassafras variifolium Species 0.000 description 2
- 240000006410 Sida spinosa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 240000007313 Tilia cordata Species 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 244000067505 Xanthium strumarium Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical class CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- KWGFMMAPDMTJHX-UHFFFAOYSA-N sulfonylthiourea Chemical class SC(=N)N=S(=O)=O KWGFMMAPDMTJHX-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73921485A | 1985-05-30 | 1985-05-30 | |
| US84961886A | 1986-04-11 | 1986-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO862137L true NO862137L (no) | 1986-12-01 |
Family
ID=27113497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO862137A NO862137L (no) | 1985-05-30 | 1986-05-29 | Nye sulfonamider med herbicid virkning. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0204513B1 (de) |
| KR (1) | KR900006100B1 (de) |
| CN (1) | CN1027999C (de) |
| AT (1) | ATE65161T1 (de) |
| AU (1) | AU581317B2 (de) |
| BR (1) | BR8602412A (de) |
| CA (1) | CA1231336A (de) |
| DE (1) | DE3680242D1 (de) |
| DK (1) | DK252186A (de) |
| ES (2) | ES8706652A1 (de) |
| GR (1) | GR861386B (de) |
| HU (1) | HU201452B (de) |
| IL (1) | IL78962A (de) |
| NO (1) | NO862137L (de) |
| NZ (1) | NZ216357A (de) |
| PT (1) | PT82666B (de) |
| SU (1) | SU1660571A3 (de) |
| TR (1) | TR23218A (de) |
| ZW (1) | ZW11086A1 (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5108487A (en) * | 1986-10-17 | 1992-04-28 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4927453A (en) * | 1986-10-17 | 1990-05-22 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US5869428A (en) * | 1995-03-13 | 1999-02-09 | Ishihara Sangyo Kaisha Ltd. | Pyridonesulfonylurea compounds, process for their production and herbicides containing them |
| US7741485B2 (en) * | 2003-04-08 | 2010-06-22 | Basf Aktiengesellschaft | Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds |
| WO2014002109A1 (en) | 2012-06-26 | 2014-01-03 | Rallis India Limited | Substituted tetrazole compounds and process thereof |
| WO2014002110A1 (en) | 2012-06-26 | 2014-01-03 | Rallis India Limited | Substitutued pyrazole compounds and process for preparation thereof. |
| US9708336B2 (en) | 2014-01-22 | 2017-07-18 | Merck Sharp & Dohme Corp. | Metallo-beta-lactamase inhibitors |
| US9839642B2 (en) | 2014-05-09 | 2017-12-12 | Merck Sharp & Dohme Corp. | Beta-tetrazolyl-propionic acids as metallo-beta-lactamase inhibitors |
| WO2016206101A1 (en) | 2015-06-26 | 2016-12-29 | Merck Sharp & Dohme Corp. | Metallo-beta-lactamase inhibitors |
| US11840543B2 (en) | 2017-05-24 | 2023-12-12 | The University Of Queensland | Compounds and uses |
| EP3654968B1 (de) | 2017-07-17 | 2023-08-16 | Merck Sharp & Dohme LLC | Metallo-beta-lactamase-inhibitoren und verfahren zu deren verwendung |
| TW201910316A (zh) | 2017-08-15 | 2019-03-16 | 愛爾蘭商英弗雷佐姆有限公司 | 新穎化合物 |
| EP3668843A1 (de) | 2017-08-15 | 2020-06-24 | Inflazome Limited | Sulfonylharnstoffe und sulfonylthioharnstoffe als nlrp3-inhibitoren |
| TW201910317A (zh) | 2017-08-15 | 2019-03-16 | 愛爾蘭商英弗雷佐姆有限公司 | 新穎化合物 |
| PE20210050A1 (es) | 2017-11-09 | 2021-01-08 | Inflazome Ltd | Nuevos compuestos de sulfonamida carboxamida |
| EP3707137A1 (de) | 2017-11-09 | 2020-09-16 | Inflazome Limited | Neuartige sulfonamid-carboxamid-verbindungen |
| WO2019166619A1 (en) | 2018-03-02 | 2019-09-06 | Inflazome Limited | Novel compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR8300034A (pt) * | 1982-01-07 | 1983-09-13 | Du Pont | Composto;composicao adequada para controlar o crescimento de vegetacao indesejada;processo para controlar o crescimento de vegetacao indesejada |
| US4475944A (en) * | 1982-06-09 | 1984-10-09 | E. I. Du Pont De Nemours And Company | Herbicidal sulfamates |
| EP0111442A1 (de) * | 1982-11-12 | 1984-06-20 | Ciba-Geigy Ag | N-2-Heterocyclyl-phenylsulfonyl-N'-pyrimidinyl- und -triazinyl-harnstoffe |
-
1986
- 1986-05-22 CA CA000509793A patent/CA1231336A/en not_active Expired
- 1986-05-27 BR BR8602412A patent/BR8602412A/pt unknown
- 1986-05-28 PT PT82666A patent/PT82666B/pt unknown
- 1986-05-28 GR GR861386A patent/GR861386B/el unknown
- 1986-05-29 IL IL78962A patent/IL78962A/xx not_active IP Right Cessation
- 1986-05-29 NZ NZ216357A patent/NZ216357A/xx unknown
- 1986-05-29 EP EP86304075A patent/EP0204513B1/de not_active Expired - Lifetime
- 1986-05-29 DE DE8686304075T patent/DE3680242D1/de not_active Expired - Lifetime
- 1986-05-29 AT AT86304075T patent/ATE65161T1/de not_active IP Right Cessation
- 1986-05-29 SU SU864027542A patent/SU1660571A3/ru active
- 1986-05-29 HU HU862267A patent/HU201452B/hu not_active IP Right Cessation
- 1986-05-29 ES ES555484A patent/ES8706652A1/es not_active Expired
- 1986-05-29 DK DK252186A patent/DK252186A/da not_active Application Discontinuation
- 1986-05-29 NO NO862137A patent/NO862137L/no unknown
- 1986-05-30 KR KR1019860004323A patent/KR900006100B1/ko not_active Expired
- 1986-05-30 AU AU58093/86A patent/AU581317B2/en not_active Expired
- 1986-05-30 ZW ZW110/86A patent/ZW11086A1/xx unknown
- 1986-11-24 CN CN86108740A patent/CN1027999C/zh not_active Expired - Lifetime
-
1987
- 1987-02-13 ES ES557392A patent/ES8801825A1/es not_active Expired
- 1987-05-29 TR TR283/86D patent/TR23218A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1027999C (zh) | 1995-03-29 |
| DE3680242D1 (de) | 1991-08-22 |
| ATE65161T1 (de) | 1991-08-15 |
| ES557392A0 (es) | 1988-02-16 |
| HUT41227A (en) | 1987-04-28 |
| DK252186D0 (da) | 1986-05-29 |
| AU5809386A (en) | 1986-12-04 |
| IL78962A (en) | 1989-12-15 |
| ES8801825A1 (es) | 1988-02-16 |
| PT82666B (pt) | 1988-08-17 |
| PT82666A (en) | 1986-06-01 |
| DK252186A (da) | 1986-12-01 |
| ZW11086A1 (en) | 1986-12-31 |
| BR8602412A (pt) | 1987-01-21 |
| ES8706652A1 (es) | 1987-07-01 |
| EP0204513B1 (de) | 1991-07-17 |
| KR900006100B1 (ko) | 1990-08-22 |
| EP0204513A2 (de) | 1986-12-10 |
| ES555484A0 (es) | 1987-07-01 |
| SU1660571A3 (ru) | 1991-06-30 |
| EP0204513A3 (en) | 1988-07-20 |
| HU201452B (en) | 1990-11-28 |
| KR860008992A (ko) | 1986-12-19 |
| TR23218A (tr) | 1989-06-21 |
| AU581317B2 (en) | 1989-02-16 |
| CA1231336A (en) | 1988-01-12 |
| NZ216357A (en) | 1988-11-29 |
| IL78962A0 (en) | 1986-09-30 |
| GR861386B (en) | 1986-09-17 |
| CN86108740A (zh) | 1988-06-08 |
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