UA48114C2 - Заміщені азадіоксациклоалкени, спосіб їх одержання, фунгіцидні засоби на основі заміщених азадіоксациклоалкенів та спосіб їх одержання - Google Patents

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Publication number

UA48114C2

UA48114C2 UA96020465A UA96020465A UA48114C2 UA 48114 C2 UA48114 C2 UA 48114C2 UA 96020465 A UA96020465 A UA 96020465A UA 96020465 A UA96020465 A UA 96020465A UA 48114 C2 UA48114 C2 UA 48114C2

Authority

UA

Ukraine

Prior art keywords

unsubstituted

carbon atoms

substituted

cyano

alkyl

Prior art date

1993-08-11

Links

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• Global Dossier
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• 239000000417 fungicide Substances 0.000 title claims abstract description 8
• 238000000034 method Methods 0.000 title claims description 35
• 239000001301 oxygen Substances 0.000 claims abstract description 31
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
• 125000001424 substituent group Chemical group 0.000 claims abstract description 11
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 7
• 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 6
• 125000005277 alkyl imino group Chemical group 0.000 claims abstract description 5
• 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 5
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• 125000000732 arylene group Chemical group 0.000 claims abstract description 3
• -1 3-thia-1-propene-2,3-diyl Chemical group 0.000 claims description 293
• 125000004432 carbon atom Chemical group C* 0.000 claims description 97
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 239000011737 fluorine Substances 0.000 claims description 49
• 229910052731 fluorine Inorganic materials 0.000 claims description 49
• 239000000460 chlorine Substances 0.000 claims description 48
• 229910052801 chlorine Inorganic materials 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 47
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 46
• 150000001875 compounds Chemical class 0.000 claims description 45
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 239000013543 active substance Substances 0.000 claims description 31
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 30
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
• 229910052794 bromium Inorganic materials 0.000 claims description 26
• 239000011593 sulfur Substances 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• 239000003085 diluting agent Substances 0.000 claims description 17
• 125000003282 alkyl amino group Chemical group 0.000 claims description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims description 15
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
• 230000003993 interaction Effects 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 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 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
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
• 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 4
• 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 239000000945 filler Substances 0.000 claims description 4
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 4
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
• 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 3
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000005027 hydroxyaryl group Chemical group 0.000 claims description 3
• 238000011065 in-situ storage Methods 0.000 claims description 3
• 150000003839 salts Chemical class 0.000 claims description 3
• 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 239000007795 chemical reaction product Substances 0.000 claims description 2
• 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 239000012433 hydrogen halide Substances 0.000 claims description 2
• 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
• 125000004957 naphthylene group Chemical group 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 238000007363 ring formation reaction Methods 0.000 claims description 2
• 238000000926 separation method Methods 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 14
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 6
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
• 101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 claims 1
• SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 1
• 241000233866 Fungi Species 0.000 claims 1
• 238000007796 conventional method Methods 0.000 claims 1
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
• 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 1
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
• 239000002446 δ-tocopherol Substances 0.000 claims 1
• 239000005864 Sulphur Chemical group 0.000 abstract 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
• 239000000126 substance Substances 0.000 description 37
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 24
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• 230000007958 sleep Effects 0.000 description 19
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• 238000002360 preparation method Methods 0.000 description 17
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• 235000011181 potassium carbonates Nutrition 0.000 description 8
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• 239000007858 starting material Substances 0.000 description 6
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