KR930005990A - 살진드기 및 살충 활성을 갖는 옥사(티아)디아졸-및 트리아졸-온(티온) - Google Patents
살진드기 및 살충 활성을 갖는 옥사(티아)디아졸-및 트리아졸-온(티온) Download PDFInfo
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- KR930005990A KR930005990A KR1019920016950A KR920016950A KR930005990A KR 930005990 A KR930005990 A KR 930005990A KR 1019920016950 A KR1019920016950 A KR 1019920016950A KR 920016950 A KR920016950 A KR 920016950A KR 930005990 A KR930005990 A KR 930005990A
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- WRLBAVRHUGJQEC-UHFFFAOYSA-N 1H-pyrazole triazol-4-one Chemical compound C=1C=NNC=1.O=C1C=NN=N1 WRLBAVRHUGJQEC-UHFFFAOYSA-N 0.000 title claims abstract 16
- 241000534944 Thia Species 0.000 title claims abstract 16
- 241001061127 Thione Species 0.000 title claims abstract 16
- 230000000895 acaricidal effect Effects 0.000 title claims abstract 3
- 239000000642 acaricide Substances 0.000 title claims abstract 3
- 230000000361 pesticidal effect Effects 0.000 title claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims 20
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 241000607479 Yersinia pestis Species 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 241000238876 Acari Species 0.000 claims 2
- 206010061217 Infestation Diseases 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 1
- BWTYXCASFXVGBL-UHFFFAOYSA-N 3-(2-bromophenyl)-5-[(4-butan-2-yloxyphenyl)methyl]-1,3,4-thiadiazol-2-one Chemical compound C1=CC(OC(C)CC)=CC=C1CC(SC1=O)=NN1C1=CC=CC=C1Br BWTYXCASFXVGBL-UHFFFAOYSA-N 0.000 claims 1
- QWQHHFRKNHFINN-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-[(4-cyclopentyloxyphenyl)methyl]-1,3,4-oxadiazol-2-one Chemical compound ClC1=CC=CC=C1N1C(=O)OC(CC=2C=CC(OC3CCCC3)=CC=2)=N1 QWQHHFRKNHFINN-UHFFFAOYSA-N 0.000 claims 1
- MSGIIGJHUIXFPA-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-[(4-cyclopentyloxyphenyl)methyl]-1,3,4-thiadiazol-2-one Chemical compound ClC1=CC=CC=C1N1C(=O)SC(CC=2C=CC(OC3CCCC3)=CC=2)=N1 MSGIIGJHUIXFPA-UHFFFAOYSA-N 0.000 claims 1
- HHORTOJJSNPMTD-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-[1-(4-propan-2-yloxyphenyl)ethyl]-1,3,4-oxadiazol-2-one Chemical compound C1=CC(OC(C)C)=CC=C1C(C)C(OC1=O)=NN1C1=CC=CC=C1Cl HHORTOJJSNPMTD-UHFFFAOYSA-N 0.000 claims 1
- BBNMQCSOMFUCNJ-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-[1-(4-propan-2-yloxyphenyl)ethyl]-1,3,4-thiadiazol-2-one Chemical compound C1=CC(OC(C)C)=CC=C1C(C)C(SC1=O)=NN1C1=CC=CC=C1Cl BBNMQCSOMFUCNJ-UHFFFAOYSA-N 0.000 claims 1
- PUGDWJVJPLOIHA-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-[[4-(2-ethylhexoxy)phenyl]methyl]-1,3,4-thiadiazol-2-one Chemical compound C1=CC(OCC(CC)CCCC)=CC=C1CC(SC1=O)=NN1C1=CC=CC=C1Cl PUGDWJVJPLOIHA-UHFFFAOYSA-N 0.000 claims 1
- SPGIJXJARPOWLG-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-[[4-(2-methylpropoxy)phenyl]methyl]-1,3,4-thiadiazol-2-one Chemical compound C1=CC(OCC(C)C)=CC=C1CC(SC1=O)=NN1C1=CC=CC=C1Cl SPGIJXJARPOWLG-UHFFFAOYSA-N 0.000 claims 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- FDCKCFSAWSKJGY-UHFFFAOYSA-N 5-[(4-but-3-yn-2-yloxyphenyl)methyl]-3-(2-chlorophenyl)-1,3,4-oxadiazol-2-one Chemical compound CC(C#C)OC1=CC=C(CC2=NN(C(O2)=O)C2=C(C=CC=C2)Cl)C=C1 FDCKCFSAWSKJGY-UHFFFAOYSA-N 0.000 claims 1
- CJIPFCXTBGSVFY-UHFFFAOYSA-N 5-[(4-but-3-yn-2-yloxyphenyl)methyl]-3-(2-chlorophenyl)-1,3,4-thiadiazol-2-one Chemical compound CC(C#C)OC1=CC=C(CC2=NN(C(S2)=O)C2=C(C=CC=C2)Cl)C=C1 CJIPFCXTBGSVFY-UHFFFAOYSA-N 0.000 claims 1
- MHSNNXCEHMMVGE-UHFFFAOYSA-N 5-[(4-butan-2-yloxyphenyl)methyl]-3-(2-chlorophenyl)-1,3,4-oxadiazol-2-one Chemical compound C1=CC(OC(C)CC)=CC=C1CC(OC1=O)=NN1C1=CC=CC=C1Cl MHSNNXCEHMMVGE-UHFFFAOYSA-N 0.000 claims 1
- SZPXLGJGRUVDNR-UHFFFAOYSA-N 5-[(4-butan-2-yloxyphenyl)methyl]-3-(2-chlorophenyl)-1,3,4-thiadiazol-2-one Chemical compound C1=CC(OC(C)CC)=CC=C1CC(SC1=O)=NN1C1=CC=CC=C1Cl SZPXLGJGRUVDNR-UHFFFAOYSA-N 0.000 claims 1
- KIYVIWABPUAOOM-UHFFFAOYSA-N 5-[(4-butan-2-yloxyphenyl)methyl]-3-(2-methylphenyl)-1,3,4-thiadiazol-2-one Chemical compound C1=CC(OC(C)CC)=CC=C1CC(SC1=O)=NN1C1=CC=CC=C1C KIYVIWABPUAOOM-UHFFFAOYSA-N 0.000 claims 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940126142 compound 16 Drugs 0.000 claims 1
- 229940125810 compound 20 Drugs 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- 229940127204 compound 29 Drugs 0.000 claims 1
- 229940125877 compound 31 Drugs 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/13—Oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
살진드기 및 살충 활성을 갖는 하기 일반식(Ⅰ)의 옥사(티아)디아졸-및 트리아졸-온(티온)이 개시된다.
(상기 식에서, Y=O이고, Z=O, S, HCH3이며, 두 치환체 P 및 Q중의 하나는 오르토-치환 페닐이고 그 나머지는 치환 벤질이다].
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (17)
- 하기 일반식(Ⅰ)를 갖는 옥사(티아)디아졸-및 트리아졸-온(티온).[상기 식에서, Y는 O, S를 나타내고, Z은 O, S또는 NMe(Me=메틸)기를 나타내며; P는 Fp기 또는 Bp기를 나타내고; Q는, P=Fp일 경우에는 Bq또는 P=Bp 및 Z=O 또는 S일 경우는 Fq를 나타내며, 여기서,단, 상기 Fp, Fq, Bp 및 Bq기 중에서, X는 Cl, F, Br, Me, CF3, 또는 MeO를 나타내며; X1은 H또는 F를 나타내고; X2는 H, F 또는 Cl을 나타내고; X2는 H, F, Cl 또는 C1~C4알콕시를 나타내고; R1및 R2는 독립적으로 H 또는 C1~C3알킬을 나타내며; Rx는 C3~C10알콕시, C3~C6알케닐옥시, C3~C8알키닐옥시, C3~C8시클로알콕시, C4~C8시클로알킬알콕시, 전체가 임의 할로겐화된 C3~C10알콕시알콕시, 또는 할로겐 원자로 임의 치환된 페녹시 또는 페닐알콕시, 알킬기, 할로알킬기, 알콕시기, 할로알콕시기를 나타내고 R3은 C1~C3알킬기를 나타낸다].
- 하기 일반식(Ⅰ)를 갖는 옥사(티아)디아졸-및 트리아졸-온(티온).[상기 식에서, Y는 O, S를 나타내고, Z은 O, S또는 NMe(Me=메틸)기를 나타내며; P는 Fp기 또는 Bp기를 나타내고; Q는, P=Fp일 경우에는 Bq기이고, P=Bp 및 Z=O 또는 S일 경우는 Fq를 나타내며, 여기서,단, 상기 Fp, Fq, Bp 및 Bq기 중에서, X는 Cl, F, Br, Me, CF3, MeO를 나타내며; X1은 H또는 F를 나타내며; X2는 H, F또는 Cl을 나타내고; X3은 H, F, Cl또는 C1~C4알콕시를 나타내며; R1및 R2는 독립적으로 H 또는 C1~C3알킬을 나타내고; Rx는 C1~C10알킬, C3~C8시클로알킬, C4~C8시클로알킬알킬, C3~C10알콕시, C3~C8시클로알콕시, C4~C8시클로알킬알콕시, 전체가 임의 할로겐화된 C3~C10알콕시알콕시, 또는 할로겐 원자로 임의 치환된 페녹시 또는 페닐알콕시, 알킬기, 할로알킬기, 알콕시기, 할로알콕시기를 나타낸다].
- (a)하기 식(Ⅱ)를 갖는 히드라지드 또는 티오히드라지를 20℃~반응 혼합물의 비점의 온도 범위로 비활성 유기 용매에서 임의로 염기 존재하에 포스겐 또는 티오포스겐 또는 트리클로로메틸클로로포르미에이트와 반응시켜 하기 식(Ⅰa)를 갖는 화합물을 수득하고, (b)이어서, Y 및 Z이 O이고; P=Fp 및 Q=Bq인 식(Ⅰa)의 화합물을 반응 혼합물의 환류온도로 비활성 유기 용매에서 메틸아민과 반응시킨 다음, 염기의 존재하에 혼합물을 가열하여 하기 식(Ⅰc)의 화합물을 수득하여, (c)이어서, 식(Ⅰc)의 화합물을 반응 혼합물의 비점으로 비활성 유기 용매에서 황화제와 반응시켜 하기 식(Ⅰe)를 수득하는 것으로 구성됨을 특징으로 하는 일반식(Ⅰ)의 제조방법.[상기 식에서, Z1및 Y는 O, S이고, Me=메틸이며, Z=NMe이고, P 및 Q는 제1항의 정의와 동일하며, 단 식(Ⅰe)에서는 P=Fp 및 Q=Bq이다].
- 해충 및 진드기의 만연 지역에 걸쳐 하나 이상의 제1항에 기재된 화합물의 유효량을 살포하는 것을 특징으로 하는 해충 및 진드기의 칩습(infestation)의 방제방법.
- 고체 또는 액체 담체 및 임의의 기타 첨가제와 함께 하나 이상의 제1항에 기재된 화합물의 유효량을 함유하는 살진드기 및 살충 조성물.
- 제1항에 있어서, 5-(4-sec-부톡시벤질)-3-(2-클로로-페닐)-1,3,4-옥사디아졸-2(3H)-온(화합물4)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 5-(4-시클로펜톡시벤질)-3-(2-클로로펜닐)-1,3,4-옥사디아졸-2(3H)-온(화합물16)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 5-(4-(3-부틴-2-옥시)벤질)-3-(2-클로로페닐)-1,3,4-옥사디아졸-2(3H)-온(화합물19)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 3-(2-클로로페닐)-5-[1-(4-iso-프로폭시페닐)에틸]-1,3,4-옥사디아졸-2(3H)-온(화합물20)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 5-(4-sec-부톡시벤질)-3-(2-클로로페닐)-1,3,4-티아디아졸-2(3H)-온(화합물25)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 5-(4-iso-부톡시벤질)-3-(2-클로로페닐)-1,3,4-티아디아졸-2(3H)-온(화합물26)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 5-(4-sec-부톡시벤질)-3-(2-메틸페닐)-1,3,4-티아디아졸-2(3H)-온(화합물29)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 3-(2-클로로페닐)-5-[4-(2-에틸헥실옥시)벤질]-1,3,4-티아디아졸-2(3H)-온(화합물30)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 5-(4-시클로펜톡시벤질)-3-(2-클로로페닐)-1,3,4-티아디아졸-2(3H)-온(화합물31)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 3-(2-브로모페닐)-5-(4-sec-부톡시벤질)-1,3,4-티아디아졸-2(3H)-온(화합물32)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 5-[4-(3-부틴-2-옥시)벤질]-3-(2-클로로페닐)-1,3,4-티아디아졸-2(3H)-온(화합물34)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).
- 제1항에 있어서, 3-(2-클로로페닐)-5-[1-(4-iso-프로폭시페닐)에틸]-1,3,4-티아디아졸-2(3H)-온(화합물35)임을 특징으로 하는 옥사(티아)디아졸- 및 트리아졸-온(티온).※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI912456A IT1251488B (it) | 1991-09-17 | 1991-09-17 | Ossa(tia)diazol- e triazol-oni(tioni) ad attivita' acaricida ed insetticida |
| ITMI91A002456 | 1991-09-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR930005990A true KR930005990A (ko) | 1993-04-20 |
| KR950004707B1 KR950004707B1 (ko) | 1995-05-04 |
Family
ID=11360684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920016950A KR950004707B1 (ko) | 1991-09-17 | 1992-09-17 | 살진드기 및 살충 활성을 갖는 옥사(티아)디아졸-및 트리아졸-온(티온) |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5418246A (ko) |
| EP (1) | EP0533276B1 (ko) |
| JP (1) | JPH06263746A (ko) |
| KR (1) | KR950004707B1 (ko) |
| AT (1) | ATE156124T1 (ko) |
| DE (1) | DE69221234T2 (ko) |
| DK (1) | DK0533276T3 (ko) |
| ES (1) | ES2104812T3 (ko) |
| IT (1) | IT1251488B (ko) |
| TW (1) | TW212794B (ko) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19531892A1 (de) * | 1995-08-30 | 1997-03-06 | Bayer Ag | 1,3,4-Oxadiazolin-2-one |
| IT1277681B1 (it) * | 1995-12-21 | 1997-11-11 | Isagro Ricerca Srl | Ariltiadiazoloni ad attivita' erbicida |
| TW467902B (en) * | 1996-07-31 | 2001-12-11 | Bristol Myers Squibb Co | Diphenyl heterocycles as potassium channel modulators |
| CA2318814A1 (en) * | 1998-01-29 | 1999-08-05 | Xi Chen | Benzoate derivatives of diaryl 1,3,4-oxadiazolone |
| DE69912250T2 (de) * | 1998-01-29 | 2004-07-29 | Bristol-Myers Squibb Co., Wallingford | Phosphorylierte derivate des diaryl 1,3,4 oxadiazolon |
| EP1056731A4 (en) * | 1998-01-29 | 2002-07-31 | Bristol Myers Squibb Co | AMINOACID DERIVATIVES OF DIARYL 1,3,4-OXADIAZOLONE |
| AU735704B2 (en) * | 1998-01-29 | 2001-07-12 | Bristol-Myers Squibb Company | Derivatives of 1,3,4-oxadiazolone |
| US6297241B1 (en) | 1999-01-29 | 2001-10-02 | Bristol-Myers Squibb Company | Carbamate derivatives of diaryl 1,3,4-oxadiazolone |
| CA2358964A1 (en) * | 1999-01-29 | 2000-08-03 | Xi Chen | Carbamate derivatives of diaryl 1,3,4-oxadiazolone |
| DE102006024024A1 (de) | 2006-05-23 | 2007-11-29 | Bayer Healthcare Aktiengesellschaft | Substituierte Arylimidazolone und -triazolone sowie ihre Verwendung |
| DE102008060967A1 (de) | 2008-12-06 | 2010-06-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Phenylsulfonyltriazolone und ihre Verwendung |
| DE102010001064A1 (de) | 2009-03-18 | 2010-09-23 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung |
| MA34019B1 (fr) | 2010-02-27 | 2013-02-01 | Bayer Ip Gmbh | Aryltriazolone liée à un bis-aryle et son utilisation |
| DE102010040187A1 (de) | 2010-09-02 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Substituierte N-Phenethyl-triazolonacetamide und ihre Verwendung |
| DE102010040924A1 (de) | 2010-09-16 | 2012-03-22 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Phenylacet- und Phenylpropanamide und ihre Verwendung |
| CN113461630B (zh) * | 2021-06-10 | 2022-09-02 | 郑州大学 | 含1,3,4-噁二唑环的诺卡酮硫醚类衍生物、及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5210421A (en) * | 1975-07-16 | 1977-01-26 | Nippon Soda Co Ltd | A thiadiazoline series germicide |
| DK570987A (da) * | 1986-12-01 | 1988-06-02 | Hoffmann La Roche | Oxadiazol-, thiadiazol- og triazolforbindelser |
| DE3931843A1 (de) * | 1989-09-23 | 1991-04-04 | Bayer Ag | Substituierte 1,3,4-oxa(thia)diazolinone verfahren zu ihrer herstellung und ihre verwendung der bekaempfung von endoparasiten |
-
1991
- 1991-09-17 IT ITMI912456A patent/IT1251488B/it active IP Right Grant
-
1992
- 1992-09-15 ES ES92202824T patent/ES2104812T3/es not_active Expired - Lifetime
- 1992-09-15 AT AT92202824T patent/ATE156124T1/de not_active IP Right Cessation
- 1992-09-15 DK DK92202824.6T patent/DK0533276T3/da active
- 1992-09-15 US US07/945,135 patent/US5418246A/en not_active Expired - Fee Related
- 1992-09-15 EP EP92202824A patent/EP0533276B1/en not_active Expired - Lifetime
- 1992-09-15 DE DE69221234T patent/DE69221234T2/de not_active Expired - Fee Related
- 1992-09-17 KR KR1019920016950A patent/KR950004707B1/ko not_active IP Right Cessation
- 1992-09-17 TW TW081107313A patent/TW212794B/zh active
- 1992-09-17 JP JP4273620A patent/JPH06263746A/ja active Pending
-
1995
- 1995-02-21 US US08/391,240 patent/US5550140A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI912456A0 (it) | 1991-09-17 |
| ATE156124T1 (de) | 1997-08-15 |
| US5550140A (en) | 1996-08-27 |
| EP0533276A1 (en) | 1993-03-24 |
| TW212794B (ko) | 1993-09-11 |
| DK0533276T3 (da) | 1997-12-29 |
| US5418246A (en) | 1995-05-23 |
| EP0533276B1 (en) | 1997-07-30 |
| ITMI912456A1 (it) | 1993-03-17 |
| DE69221234T2 (de) | 1998-03-12 |
| ES2104812T3 (es) | 1997-10-16 |
| IT1251488B (it) | 1995-05-15 |
| JPH06263746A (ja) | 1994-09-20 |
| KR950004707B1 (ko) | 1995-05-04 |
| DE69221234D1 (de) | 1997-09-04 |
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