SK107597A3 - Fungicidal aza-heterocycloalkenes, producing method thereof, agents for killing the pests containing the same, method of killing the pests and use said compounds - Google Patents

Info

Publication number

SK107597A3

SK107597A3 SK1075-97A SK107597A SK107597A3 SK 107597 A3 SK107597 A3 SK 107597A3 SK 107597 A SK107597 A SK 107597A SK 107597 A3 SK107597 A3 SK 107597A3

Authority

SK

Slovakia

Prior art keywords

group

optionally

cyano

substituted

carbon atoms

Prior art date

1995-02-13

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 53
• 238000000034 method Methods 0.000 title claims description 41
• 230000000855 fungicidal effect Effects 0.000 title claims description 13
• 241000607479 Yersinia pestis Species 0.000 title claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
• 239000001301 oxygen Substances 0.000 claims abstract description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
• -1 3-aza-1-propene-2,3-diyl Chemical group 0.000 claims description 420
• 125000004432 carbon atom Chemical group C* 0.000 claims description 94
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 84
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
• 239000000460 chlorine Substances 0.000 claims description 66
• 229910052717 sulfur Inorganic materials 0.000 claims description 58
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
• 229910052801 chlorine Inorganic materials 0.000 claims description 53
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 52
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 50
• 239000011737 fluorine Substances 0.000 claims description 48
• 229910052731 fluorine Inorganic materials 0.000 claims description 48
• 125000004434 sulfur atom Chemical group 0.000 claims description 48
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 47
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 150000002367 halogens Chemical class 0.000 claims description 32
• 125000005843 halogen group Chemical group 0.000 claims description 30
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 29
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 28
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 28
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 27
• 238000002360 preparation method Methods 0.000 claims description 26
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
• 229910052794 bromium Inorganic materials 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 20
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 14
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
• 125000000335 thiazolyl group Chemical group 0.000 claims description 14
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 13
• 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 13
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• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 150000002440 hydroxy compounds Chemical class 0.000 claims description 11
• 239000000203 mixture Substances 0.000 claims description 11
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 10
• 239000003085 diluting agent Substances 0.000 claims description 10
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• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 9
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 7
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 6
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 125000004957 naphthylene group Chemical group 0.000 claims description 6
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 125000005700 haloalkyleneoxy group Chemical group 0.000 claims description 5
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 239000003208 petroleum Substances 0.000 claims description 5
• 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 4
• 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
• 239000013543 active substance Substances 0.000 claims description 4
• 125000001931 aliphatic group Chemical group 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
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• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
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• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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• 125000006413 ring segment Chemical group 0.000 claims description 4
• 125000005649 substituted arylene group Chemical group 0.000 claims description 4
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
• 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 3
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• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 3
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
• 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
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• GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
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