KR20040011484A - 치환된플루오로알콕시페닐설포닐아미노(티오)카보닐트리아졸린(티)온 - Google Patents

Info

Publication number

KR20040011484A

KR20040011484A KR10-2003-7012388A KR20037012388A KR20040011484A KR 20040011484 A KR20040011484 A KR 20040011484A KR 20037012388 A KR20037012388 A KR 20037012388A KR 20040011484 A KR20040011484 A KR 20040011484A

Authority

KR

South Korea

Prior art keywords

oxygen

group

methyl

methoxy

ethoxy

Prior art date

2001-04-09

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

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• -1 (thio) carbonyltriazolin Chemical class 0.000 claims abstract description 252
• 150000001875 compounds Chemical class 0.000 claims abstract description 74
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims abstract description 36
• 238000000034 method Methods 0.000 claims abstract description 36
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 348
• 239000001301 oxygen Substances 0.000 claims description 348
• 229910052760 oxygen Inorganic materials 0.000 claims description 348
• 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims description 56
• 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 44
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
• 125000001449 isopropyl group Chemical class [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 29
• 125000004123 n-propyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 29
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 28
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 24
• 239000000203 mixture Substances 0.000 claims description 20
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 19
• 230000008569 process Effects 0.000 claims description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
• 238000006243 chemical reaction Methods 0.000 claims description 18
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 239000011593 sulfur Substances 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000000959 isobutyl group Chemical class [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 125000004108 n-butyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 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
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 230000002363 herbicidal effect Effects 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• 125000002914 sec-butyl group Chemical class [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical class C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims description 6
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
• 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 6
• 125000004368 propenyl group Chemical class C(=CC)* 0.000 claims description 6
• 125000002568 propynyl group Chemical class [*]C#CC([H])([H])[H] 0.000 claims description 6
• 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 6
• 229910052751 metal Inorganic materials 0.000 claims description 5
• 239000002184 metal Substances 0.000 claims description 5
• 125000000999 tert-butyl group Chemical class [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004369 butenyl group Chemical class C(=CCC)* 0.000 claims description 4
• 125000000480 butynyl group Chemical class [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
• 238000007796 conventional method Methods 0.000 claims description 4
• 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
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
• 239000004606 Fillers/Extenders Substances 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
• BVDXCHGWNQVCFS-UHFFFAOYSA-N N-[2-(2-fluoroethoxy)-6-methylphenyl]sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboxamide Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=C(C)C=CC=C1OCCF BVDXCHGWNQVCFS-UHFFFAOYSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
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• 206010041349 Somnolence Diseases 0.000 claims 1
• 241000927721 Tritia Species 0.000 claims 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract description 14
• 238000002360 preparation method Methods 0.000 abstract description 13
• 239000004009 herbicide Substances 0.000 abstract description 9
• 241000196324 Embryophyta Species 0.000 description 76
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 37
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 37
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 22
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 16
• 238000012360 testing method Methods 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
• 239000007858 starting material Substances 0.000 description 15
• 230000035784 germination Effects 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 241000219146 Gossypium Species 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000002689 soil Substances 0.000 description 9
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