UA78204C2 - Substituted fluoralkoxyphenylsulfonylamino(thio)carbonyltriazolino(thi)ones and herbicidal agent based thereon - Google Patents

Info

Publication number

UA78204C2

UA78204C2 UA20031110064A UA20031110064A UA78204C2 UA 78204 C2 UA78204 C2 UA 78204C2 UA 20031110064 A UA20031110064 A UA 20031110064A UA 20031110064 A UA20031110064 A UA 20031110064A UA 78204 C2 UA78204 C2 UA 78204C2

Authority

UA

Ukraine

Prior art keywords

oxygen

group

methyl

methoxy

ethoxy

Prior art date

2001-04-09

Links

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• 239000004009 herbicide Substances 0.000 title claims abstract description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 39
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 347
• 229910052760 oxygen Inorganic materials 0.000 claims description 347
• 239000001301 oxygen Substances 0.000 claims description 347
• -1 methoxy, ethoxy Chemical group 0.000 claims description 145
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 42
• 125000001301 ethoxy group Chemical class [H]C([H])([H])C([H])([H])O* 0.000 claims description 40
• 239000013543 active substance Substances 0.000 claims description 33
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 30
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 23
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 21
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 239000011737 fluorine Substances 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 7
• 230000002363 herbicidal effect Effects 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• 150000003456 sulfonamides Chemical class 0.000 claims description 2
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 5
• 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 4
• 125000006606 n-butoxy group Chemical group 0.000 claims 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
• 125000005920 sec-butoxy group Chemical group 0.000 claims 2
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 31
• 241000196324 Embryophyta Species 0.000 description 86
• 239000000126 substance Substances 0.000 description 30
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 25
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 23
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 18
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• 240000008042 Zea mays Species 0.000 description 13
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 13
• 239000000203 mixture Substances 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
• 235000005822 corn Nutrition 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 229920000742 Cotton Polymers 0.000 description 9
• 244000299507 Gossypium hirsutum Species 0.000 description 9
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• 239000002689 soil Substances 0.000 description 9
• 235000010469 Glycine max Nutrition 0.000 description 8
• 244000068988 Glycine max Species 0.000 description 8
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
• 230000003993 interaction Effects 0.000 description 8
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• 230000006378 damage Effects 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 229910052700 potassium Inorganic materials 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 229910052796 boron Inorganic materials 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 108090000623 proteins and genes Proteins 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• 230000009261 transgenic effect Effects 0.000 description 6
• 239000002253 acid Substances 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 5
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
• 239000008187 granular material Substances 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 238000005507 spraying Methods 0.000 description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 235000002595 Solanum tuberosum Nutrition 0.000 description 4
• 244000061456 Solanum tuberosum Species 0.000 description 4
• 244000062793 Sorghum vulgare Species 0.000 description 4
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
• 235000021307 Triticum Nutrition 0.000 description 4
• 241000209140 Triticum Species 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 4
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• 230000000694 effects Effects 0.000 description 4
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• IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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