UA77708C2 - Substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazolin(thi)ones and a herbicidal agent - Google Patents

Info

Publication number

UA77708C2

UA77708C2 UA20040604155A UA20040604155A UA77708C2 UA 77708 C2 UA77708 C2 UA 77708C2 UA 20040604155 A UA20040604155 A UA 20040604155A UA 20040604155 A UA20040604155 A UA 20040604155A UA 77708 C2 UA77708 C2 UA 77708C2

Authority

UA

Ukraine

Prior art keywords

necessary

substituted

fluorine

chlorine

methyl

Prior art date

2001-11-02

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• 239000004009 herbicide Substances 0.000 title claims abstract description 10
• 150000001875 compounds Chemical class 0.000 claims abstract description 67
• -1 hydroxy, amino Chemical group 0.000 claims description 147
• 239000000460 chlorine Substances 0.000 claims description 61
• 229910052801 chlorine Inorganic materials 0.000 claims description 61
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 58
• 229910052731 fluorine Inorganic materials 0.000 claims description 51
• 239000011737 fluorine Substances 0.000 claims description 50
• 125000004432 carbon atom Chemical group C* 0.000 claims description 49
• 125000001153 fluoro group Chemical group F* 0.000 claims description 47
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical group 0.000 claims description 19
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 239000003085 diluting agent Substances 0.000 claims description 13
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 8
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 230000002363 herbicidal effect Effects 0.000 claims description 6
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 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 5
• 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 5
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000006437 ethyl cyclopropyl group Chemical group 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 125000005920 sec-butoxy group Chemical group 0.000 claims 3
• 125000005484 neopentoxy group Chemical group 0.000 claims 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
• 125000005922 tert-pentoxy group Chemical group 0.000 claims 2
• 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
• 125000002541 furyl group Chemical group 0.000 claims 1
• 125000003566 oxetanyl group Chemical group 0.000 claims 1
• 239000004094 surface-active agent Substances 0.000 claims 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
• 125000001544 thienyl group Chemical group 0.000 claims 1
• 125000002053 thietanyl group Chemical group 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 abstract description 7
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• 150000004702 methyl esters Chemical class 0.000 description 37
• 238000000034 method Methods 0.000 description 33
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 31
• 239000002253 acid Substances 0.000 description 27
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 25
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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• 239000000047 product Substances 0.000 description 15
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