KR870001213A - 살충제 화합물의 제조방법 - Google Patents
살충제 화합물의 제조방법 Download PDFInfo
- Publication number
- KR870001213A KR870001213A KR1019860006255A KR860006255A KR870001213A KR 870001213 A KR870001213 A KR 870001213A KR 1019860006255 A KR1019860006255 A KR 1019860006255A KR 860006255 A KR860006255 A KR 860006255A KR 870001213 A KR870001213 A KR 870001213A
- Authority
- KR
- South Korea
- Prior art keywords
- octane
- trioxabicyclo
- cyano
- propyl
- optionally substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 12
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000002917 insecticide Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- -1 cyano, ethynyl Chemical group 0.000 claims 7
- 230000000361 pesticidal effect Effects 0.000 claims 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000010437 gem Substances 0.000 claims 4
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- MDHWDNKSVJUPRT-UHFFFAOYSA-N 4-(4-ethynylphenyl)-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane-2-carbonitrile Chemical compound O1CC(CCC)(C(O2)C#N)COC12C1=CC=C(C#C)C=C1 MDHWDNKSVJUPRT-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000008029 eradication Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- VOGUQIXVRHVFAR-UHFFFAOYSA-N 1,4-dicyclohexyl-2-methyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound CC1OC(OC2)(C3CCCCC3)OCC12C1CCCCC1 VOGUQIXVRHVFAR-UHFFFAOYSA-N 0.000 claims 1
- UWPXAHBMNRGKIV-UHFFFAOYSA-N 1-butyl-4-(4-chlorophenyl)-2-methyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCCC)(C(O2)C)COC12C1=CC=C(Cl)C=C1 UWPXAHBMNRGKIV-UHFFFAOYSA-N 0.000 claims 1
- CRQHOZIRICNCPV-UHFFFAOYSA-N 1-propyl-4-[4-(2-trimethylsilylethynyl)phenyl]-3,5,8-trioxabicyclo[2.2.2]octane-2-carbonitrile Chemical compound O1CC(CCC)(C(O2)C#N)COC12C1=CC=C(C#C[Si](C)(C)C)C=C1 CRQHOZIRICNCPV-UHFFFAOYSA-N 0.000 claims 1
- YYJLYHDJGNCHED-UHFFFAOYSA-N 1-tert-butyl-4-(4-chlorophenyl)-2-methyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(C(C)(C)C)(CO2)C(C)OC21C1=CC=C(Cl)C=C1 YYJLYHDJGNCHED-UHFFFAOYSA-N 0.000 claims 1
- KVJHUDAYMLICIS-UHFFFAOYSA-N 1-tert-butyl-4-(4-iodophenyl)-3,5,8-trioxabicyclo[2.2.2]octane-2-carbonitrile Chemical compound O1CC(C(C)(C)C)(C(O2)C#N)COC12C1=CC=C(I)C=C1 KVJHUDAYMLICIS-UHFFFAOYSA-N 0.000 claims 1
- QJXPHWRQYSFUDE-UHFFFAOYSA-N 1-tert-butyl-4-cyclohexyl-2-methyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(C(C)(C)C)(CO2)C(C)OC21C1CCCCC1 QJXPHWRQYSFUDE-UHFFFAOYSA-N 0.000 claims 1
- IXOYNTFKYIGWJY-UHFFFAOYSA-N 1-tert-butyl-4-cyclohexyl-3,5,8-trioxabicyclo[2.2.2]octane-2-carbonitrile Chemical compound O1CC(C(C)(C)C)(C(O2)C#N)COC12C1CCCCC1 IXOYNTFKYIGWJY-UHFFFAOYSA-N 0.000 claims 1
- CONVAEXWACQJSA-UHFFFAOYSA-N 3-oxabicyclo[2.2.2]octane Chemical compound C1CC2CCC1OC2 CONVAEXWACQJSA-UHFFFAOYSA-N 0.000 claims 1
- DRPWGYSIGSBRFO-UHFFFAOYSA-N 4-(4-bromo-3-chlorophenyl)-1-propyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C(F)(F)F)COC12C1=CC=C(Br)C(Cl)=C1 DRPWGYSIGSBRFO-UHFFFAOYSA-N 0.000 claims 1
- DYZMFMXSXVIZEQ-UHFFFAOYSA-N 4-(4-bromophenyl)-1-cyclohexyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound FC(F)(F)C1OC(OC2)(C=3C=CC(Br)=CC=3)OCC12C1CCCCC1 DYZMFMXSXVIZEQ-UHFFFAOYSA-N 0.000 claims 1
- VXMVDDVAEHVFNT-UHFFFAOYSA-N 4-(4-bromophenyl)-1-cyclohexyl-2-methyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound CC1OC(OC2)(C=3C=CC(Br)=CC=3)OCC12C1CCCCC1 VXMVDDVAEHVFNT-UHFFFAOYSA-N 0.000 claims 1
- AJMICKFBNJDEPD-UHFFFAOYSA-N 4-(4-bromophenyl)-1-propyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C(F)(F)F)COC12C1=CC=C(Br)C=C1 AJMICKFBNJDEPD-UHFFFAOYSA-N 0.000 claims 1
- VKUIYJYNNZVLBU-UHFFFAOYSA-N 4-(4-bromophenyl)-1-tert-butyl-2-ethyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(C(C)(C)C)(CO2)C(CC)OC21C1=CC=C(Br)C=C1 VKUIYJYNNZVLBU-UHFFFAOYSA-N 0.000 claims 1
- YKLKOWGKBCWLPE-UHFFFAOYSA-N 4-(4-bromophenyl)-1-tert-butyl-2-methyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(C(C)(C)C)(CO2)C(C)OC21C1=CC=C(Br)C=C1 YKLKOWGKBCWLPE-UHFFFAOYSA-N 0.000 claims 1
- JLEBKDWYIUDQTN-UHFFFAOYSA-N 4-(4-bromophenyl)-2,6-dimethyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1C(C)C(CCC)(C(O2)C)COC12C1=CC=C(Br)C=C1 JLEBKDWYIUDQTN-UHFFFAOYSA-N 0.000 claims 1
- UKYTVZOXUPBTTA-UHFFFAOYSA-N 4-(4-bromophenyl)-2-ethenyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C=C)COC12C1=CC=C(Br)C=C1 UKYTVZOXUPBTTA-UHFFFAOYSA-N 0.000 claims 1
- IWODIPMLSXJDEP-UHFFFAOYSA-N 4-(4-bromophenyl)-2-methyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C)COC12C1=CC=C(Br)C=C1 IWODIPMLSXJDEP-UHFFFAOYSA-N 0.000 claims 1
- QHNWFIVLSUCUHO-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-cyclohexyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound FC(F)(F)C1OC(OC2)(C=3C=CC(Cl)=CC=3)OCC12C1CCCCC1 QHNWFIVLSUCUHO-UHFFFAOYSA-N 0.000 claims 1
- GWLWQBAIUIVHGV-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-propyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C(F)(F)F)COC12C1=CC=C(Cl)C=C1 GWLWQBAIUIVHGV-UHFFFAOYSA-N 0.000 claims 1
- AOPWPVPDMZXUAF-UHFFFAOYSA-N 4-(4-chlorophenyl)-2,6-dimethyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1C(C)C(CCC)(C(O2)C)COC12C1=CC=C(Cl)C=C1 AOPWPVPDMZXUAF-UHFFFAOYSA-N 0.000 claims 1
- OTCITOZRQRERRH-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-1-propan-2-yl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(C(C)C)(C(O2)C)COC12C1=CC=C(Cl)C=C1 OTCITOZRQRERRH-UHFFFAOYSA-N 0.000 claims 1
- MCJLQKXCZVYUDB-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C)COC12C1=CC=C(Cl)C=C1 MCJLQKXCZVYUDB-UHFFFAOYSA-N 0.000 claims 1
- DITWZBLLQNBERA-UHFFFAOYSA-N 4-(4-cyanophenyl)-1-propan-2-yl-3,5,8-trioxabicyclo[2.2.2]octane-2-carbonitrile Chemical compound O1CC(C(C)C)(C(O2)C#N)COC12C1=CC=C(C#N)C=C1 DITWZBLLQNBERA-UHFFFAOYSA-N 0.000 claims 1
- WJSJQLUQQLCJDA-UHFFFAOYSA-N 4-(4-ethynylphenyl)-1-propyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C(F)(F)F)COC12C1=CC=C(C#C)C=C1 WJSJQLUQQLCJDA-UHFFFAOYSA-N 0.000 claims 1
- GSRHNQLPCLTLNF-UHFFFAOYSA-N 4-(4-ethynylphenyl)-2-methyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C)COC12C1=CC=C(C#C)C=C1 GSRHNQLPCLTLNF-UHFFFAOYSA-N 0.000 claims 1
- HSHJOQPTHROGIC-UHFFFAOYSA-N 4-[1-propyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octan-4-yl]benzonitrile Chemical compound O1CC(CCC)(C(O2)C(F)(F)F)COC12C1=CC=C(C#N)C=C1 HSHJOQPTHROGIC-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- IGSJPUXQRZYHIY-UHFFFAOYSA-N 4-cyclohexyl-1-propyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C(F)(F)F)COC12C1CCCCC1 IGSJPUXQRZYHIY-UHFFFAOYSA-N 0.000 claims 1
- VIEJMZFTXROUML-UHFFFAOYSA-N 4-cyclohexyl-2,6-dimethyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1C(C)C(CCC)(C(O2)C)COC12C1CCCCC1 VIEJMZFTXROUML-UHFFFAOYSA-N 0.000 claims 1
- GQPMHBKMCHMQBG-UHFFFAOYSA-N 4-cyclohexyl-2-methyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(C(O2)C)COC12C1CCCCC1 GQPMHBKMCHMQBG-UHFFFAOYSA-N 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- KFKGEXRDIXBUID-UHFFFAOYSA-N C(C)(C)(C)C12C(OC(OC1)(OC2)C2=CC=C(C=C2)CC)C#N Chemical compound C(C)(C)(C)C12C(OC(OC1)(OC2)C2=CC=C(C=C2)CC)C#N KFKGEXRDIXBUID-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical group COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Chemical group 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 239000010977 jade Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- CJLCHTUMXOMRIC-UHFFFAOYSA-N trimethyl-[2-[4-(2,6,7-trioxabicyclo[2.2.2]octan-1-yl)phenyl]ethynyl]silane Chemical compound C[Si](C)(C)C#CC1=CC=C(C=C1)C12OCC(CO1)CO2 CJLCHTUMXOMRIC-UHFFFAOYSA-N 0.000 claims 1
- SHDPWOONQADVGP-UHFFFAOYSA-N trimethyl-[2-[4-(2-methyl-1-propyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]ethynyl]silane Chemical compound O1CC(CCC)(C(O2)C)COC12C1=CC=C(C#C[Si](C)(C)C)C=C1 SHDPWOONQADVGP-UHFFFAOYSA-N 0.000 claims 1
- DHCYALNJIXMBDQ-UHFFFAOYSA-N trimethyl-[2-[4-[1-propyl-2-(trifluoromethyl)-3,5,8-trioxabicyclo[2.2.2]octan-4-yl]phenyl]ethynyl]silane Chemical compound O1CC(CCC)(C(O2)C(F)(F)F)COC12C1=CC=C(C#C[Si](C)(C)C)C=C1 DHCYALNJIXMBDQ-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
내용 없음.
Description
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Claims (8)
- 일반식 R2C(OR7)3의 오르소 카르복실레이트를 일반식(II)의 트리올과 축합시키거나 또는 일반식(VI)의 화합물을 산촉매 존재하에 고리화 하여 일반식(I)화합물을 제조하는 것을 특징으로 하는 트리옥사바이사이클로[2,2,2]-옥탄의 제조방법.상기식에서, R은 C2-10알킬, 알케닐 또는 메틸로 임의로 치환되거나 또는 치환된 시아노, C3-4사이클로알킬, 할로 C1-4알콕시 또는 S(O)mR4기(R4는 C1-4알킬, m은 0,1 또는 2)로 임의로 치환된 알키닐이거나 또는 R이 C3-10사이클로알킬, C4-10사이클로알케닐 또는 C1-4알콕시, C1-3알킬, C2-4알키닐, 할로, 시아노 또는 S(O)mR4기로 임의로 치환된 페닐; R1은 할로, C1-3알킬, C2-3알케닐 또는 할로, 시아노, C1-4알콕시, 6탄소이하의 아킬 카르브알콕시, S(O)mR4기로 임의로 치환된 알키닐 또는 트리 -C1-4알키닐시릴에 의해 치환된 알키닐, 또는 R1은 시아노, 스피로-사이클로프로필, 젬 딤틸, 젬 디시아노, 젬 디에티닐, 옥소 또는 시아노로 임의로 치환된 메틸렌 또는 불소로 임의 치환된 C1-3알킬, 또는 R1과 R과 그들에 결합된 탄소들은 할로, C1-3알킬, 또는 알콕시 또는 C2-3알케닐로 임의로 치환된 C3-7카르보사이클릭링, R2는 페닐, C5-10사이클로알킬 또는 임의로 치환된 사이클로알케닐이며 R3는 수소, C1-3알킬, C2-3알케닐 또는 시아노, C1-4알킬티오, C1-4알콕시 또는 할로로 임의 치환된 알키닐, 또는 R3는 시아노이거나 할로이며, R1은 C1-4알킬, 페닐 또는 C7-8아르알킬이다.
- 제1항에 있어서, R이 프로필, 부틸, 펜틸, C2-5알케닐 또는 알키닐, C5-7사이클로알킬 또는 1 내지 3의 플루오로, 클로로 또는 브로모로 임의로 치환된 페닐이며; R1은 시아노, 에티닐 또는 메틸 또는 시아노, 메톡시, 메틸티오 또는 플루오로로 임의 치환된 에틸이며; 는, C5-10사이클로알킬 또는 할로, 시아노, 아지도, 테트라족릴, S(O)mR5기(n은 1이며 R5는 C1-4알킬, m은 2 또는 R5가 C1-4알킬, 아미노 또는 디-C1-4알킬아미노)기 COR6(R6는 C1-4알콕시, 벤질옥시, 아미노 또는 디-C1-4알킬아미노임), 니트로로 임의로 치환된 사이클로알케닐 또는 할로, 시아노 또는 에티닐로 임의 치환된 C1-3알킬 또는 할로 또는 트리 C1-4알킬시릴로 임의로 치환된 C2-3알케닐 또는 에티닐; R3는수소 또는 메틸인 일반식(I)화합물의 제조방법.
- 제1항에 있어서, 1-(4-브로모페닐)-4-사이클로헥실-3-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-클로로페닐)-3-메틸-4-이소-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄,1-(4-브로모페닐-3-메틸-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4- 클로로페닐)-3-메틸-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-사이노헥실-3-메틸-4-이소-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐)-4-t-부틸-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1,4-디사이클로헥실-3-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄,4-t-부틸-1-(4-클로로페닐)-3-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄,1-(4-에티닐페닐)3-메틸-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 3-메틸-4-n-프로필-1-(4-(2-트리메틸시릴에티닐)-페닐)-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-에티닐페닐)-4-n-프로필-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-n-프로필-3-트리플루오로메틸-1-(4-(2-트리메틸시릴에티닐)-페닐)-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-클로로페닐)-4-n-프로필 3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄,1-(4-브로모페닐)-4-n-프로필-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-클로로페닐)-4-사이클로헥실-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐-4-사이클로헥실-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐)-3-에테닐-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-사이클로헥실-4-n-프로필-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐)-3-시아노-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 3-시아노-1-(4-에티닐페닐)-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐)-4-사이클로헥실-3-페톡시메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-사이클로헥실-3-메틸-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐)-4-t-부틸-3-에틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-t-부틸-1-사이클로헥실-3-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-클로로페닐-3,5-디메틸-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐)-3,5-디메틸-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-사이클로헥실-3,5-디메틸-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄,1-(4-시아노페닐)-4-n-프로필-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄,1-(4-브로모페닐)-4-n-부틸-3-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4- n - 부틸- 1 - (4-클로로페닐)-3-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-t-부틸-3-시아노-1-(4-에틸페닐)-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-시아노페닐)-3-에티닐-4-이소프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 3-시아노-1-(4-시아노페닐)-4-이소프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-t-부틸-3-시아노-1-(4-아이오도페닐)-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-t-부틸-3-시아노-1-(4-(2-트리메틸시릴에티닐)-페닐-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모-3-디클로로페닐)-4-n-프로필-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모-3-클로로페닐)-4-n-프로필-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-n-부틸-1-(4-브로모페닐)-3-트리플루오로메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-n-부틸-3-메틸-1-[4-(2-트리메틸시릴에티닐)페닐)-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-n-부틸-3-1-(4-에티닐페닐)-3-메틸-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 4-t-부틸-3-시아노-1-사이클로헥실-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 1-(4-브로모페닐)-3-시아노-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 3-시아노-1-(4-아이오도페닐)-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 3-시아노-4-n-프로필-1-(4-(2-트리메틸시릴에티닐)페닐)-2,6,7-트리옥사바이사이클로[2,2,2]옥탄, 또는 3-시아노-1-(4-에티닐페닐)-4-n-프로필-2,6,7-트리옥사바이사이클로[2,2,2]옥탄을 제조하는 방법.
- 제1항에 있어서, 일반식(IA)화합물의 제조방법.이식에서, Rα는 C2-4알킬, 알케닐 또는 알키닐 C5-10사이클로알킬 또는 시아노, C1-4알콕시로 이의 치환된 페닐, R1α은 시아노 또는 C1-3알킬, 시아노 C1-4알콕시, C1-4알킬티오 또는 할로로 임의 치환된 C2-3알케닐 또는 알키닐 또는 R1α는 시아노, 젬 디메틸 또는 R1α과 Rα와 그들에 결합된 탄소원자들은 C1-3알킬 또는 알콕시로 임의 치환된 C5-7카르보사이클릭링을 형성하며; R2α는 페닐, C5-10사이클로알킬 또는 임의로 치환된 사이클로알케닐이며 R3α는 수소, C1-3알킬, 시아노, C1-4알킬티오, C1-4알콕시 또는 할로로 임의 치환된 C2-3알케닐 또는 알키닐임.
- 그 활성성분이 제1 내지 4항의 일반식(I)화합물인 것을 특징으로 하며 살충 또는 진드기 박멸 활성성분과 담체 또는 희석제를 함유하는 살충 또는 진드기 박멸 제제.
- 그 활성 성분이 제1 내지 제4항의 일반식(I)화합물인 것을 특징으로 하며, 살충 활성성분에 대한 공동 상승제와 임의로 담체 또는 희석제와 살충 활성 성분을 함유하는 공력작용의 살충 조성물.
- 적어도 하나의 살충 화합물이 제1-4항의 일반식(I)화합물인 것을 특징으로 하며 적어도 두가지의 살충 화합물과 임의로 담체 또는 희석제의 혼합물을 함유하는 살충 조성물.
- a) 일반식 (가)의 보호된 디알데히드를 그리그나드 시약과 반응시킨후 하이드록시 보호기를 제거하거나 또는 b) 일반식 (나)의 에스테르를 환원시켜 R1과 R3가모두 H인 일반식(II) 화합물을 제공하거나 또는 c) 일반식 (다)의 에스테르를 환원시켜 R3가 H인 일반식(II)화합물을 제공하는 것을 특징으로 하는 하기 일반식(II)트리올의 제조방법.상기식들에서, R,R1과 R3는 제1-4항의 정의와 같고, R8은 하이드록시 보호기이며, R9는 C1-C4알킬기이며, R11은 하이드록시 보호기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858519212A GB8519212D0 (en) | 1985-07-30 | 1985-07-30 | Pesticidal compound |
| GB8519212 | 1985-07-30 | ||
| GB858522601A GB8522601D0 (en) | 1985-09-12 | 1985-09-12 | Oxygen-containing heterocyclic compounds |
| GB8522601 | 1985-09-12 | ||
| GB8606130 | 1986-03-12 | ||
| GB868606130A GB8606130D0 (en) | 1986-03-12 | 1986-03-12 | Pesticidal compounds |
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| KR870001213A true KR870001213A (ko) | 1987-03-12 |
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| KR1019860006255A KR870001213A (ko) | 1985-07-30 | 1986-07-30 | 살충제 화합물의 제조방법 |
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| EP (1) | EP0211598B1 (ko) |
| KR (1) | KR870001213A (ko) |
| CN (1) | CN86105901A (ko) |
| AU (1) | AU604212B2 (ko) |
| DE (1) | DE3689392T2 (ko) |
| DK (1) | DK165448C (ko) |
| ES (2) | ES2000778A6 (ko) |
| FI (1) | FI863091L (ko) |
| GR (1) | GR862011B (ko) |
| HU (1) | HUT41960A (ko) |
| IL (1) | IL79532A0 (ko) |
| MC (1) | MC1756A1 (ko) |
| PL (2) | PL270117A1 (ko) |
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| KR102180724B1 (ko) * | 2019-11-19 | 2020-11-19 | 김영찬 | 가공된 부엽토를 이용한 복합비료의 제조방법 및 이를 이용하여 제조된 복합비료 |
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| AU3933285A (en) * | 1984-01-30 | 1985-08-09 | Regents Of The University Of California, The | A new class of pesticides comprising 1,4-bis-substituted-2,6,7-trioxabicyclo (2.2.2) octanes |
| US4772624A (en) * | 1985-01-23 | 1988-09-20 | The Regents Of The University Of California | 1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)-octanes having ethynyl substituted phenyl group |
| ES2002364A6 (es) * | 1985-09-23 | 1988-08-01 | Wellcome Found | Un procedimiento para preparar derivados de heterobicicloalcanos |
| US5116862A (en) * | 1985-09-24 | 1992-05-26 | The Wellcome Foundation Limited | Pesticidal compounds |
| US4672098A (en) * | 1985-11-06 | 1987-06-09 | Armstrong World Industries, Inc. | Bicyclic acrylic monomers |
| IL85826A0 (en) * | 1987-03-26 | 1988-09-30 | Wellcome Found | Substituted phenyl-bicycloalkanes,their preparation and their use as pesticides |
| KR890002086A (ko) | 1987-07-22 | 1989-04-08 | 엠.피.잭슨 | 살충성 화합물과 그것의 제조방법 및 조성과 용도 |
| US5466710A (en) * | 1988-03-21 | 1995-11-14 | Roussel Uclaf | Heterobicycloalkanes as pesticidal compounds |
| US5204333A (en) * | 1989-01-24 | 1993-04-20 | Larkin John P | Pesticidal compounds |
| US5026874A (en) * | 1989-01-24 | 1991-06-25 | Wellcome Foundation Limited | Pesticidal compounds |
| CN1048496C (zh) * | 1995-03-13 | 2000-01-19 | 中国医学科学院医药生物技术研究所 | 新抗生素波拉霉素(Polaramycin)A或B及其制造方法 |
| NL1002427C2 (nl) * | 1996-02-23 | 1997-08-26 | Akzo Nobel Nv | Bekledingssamenstelling omvattende een bicyclo- of spiroorthoester functionele verbinding. |
| BR0017299A (pt) * | 2000-07-26 | 2003-06-17 | Du Pont | Processo de polimerização, composto e poliolefina |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686224A (en) | 1970-02-24 | 1972-08-22 | Gulf Research Development Co | 2,6,7-trioxabicyclo(2.2.2)octane compounds |
| ZA85734B (en) | 1984-01-30 | 1985-09-25 | Univ California | Pesticides comprising 1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)octanes |
| AU3933285A (en) | 1984-01-30 | 1985-08-09 | Regents Of The University Of California, The | A new class of pesticides comprising 1,4-bis-substituted-2,6,7-trioxabicyclo (2.2.2) octanes |
| ES2002364A6 (es) * | 1985-09-23 | 1988-08-01 | Wellcome Found | Un procedimiento para preparar derivados de heterobicicloalcanos |
| HUT44789A (en) * | 1985-09-24 | 1988-04-28 | Wellcome Found | Process for production of bicycloalcane derivatives and insecticides and acarycides containing them as active substance |
-
1986
- 1986-07-28 FI FI863091A patent/FI863091L/fi not_active IP Right Cessation
- 1986-07-28 IL IL79532A patent/IL79532A0/xx unknown
- 1986-07-29 CN CN198686105901A patent/CN86105901A/zh active Pending
- 1986-07-29 ES ES8600677A patent/ES2000778A6/es not_active Expired
- 1986-07-29 DK DK360486A patent/DK165448C/da not_active IP Right Cessation
- 1986-07-29 EP EP86305820A patent/EP0211598B1/en not_active Expired - Lifetime
- 1986-07-29 GR GR862011A patent/GR862011B/el unknown
- 1986-07-29 PT PT83086A patent/PT83086B/pt unknown
- 1986-07-29 DE DE3689392T patent/DE3689392T2/de not_active Expired - Fee Related
- 1986-07-29 MC MC861842A patent/MC1756A1/xx unknown
- 1986-07-29 HU HU863225A patent/HUT41960A/hu unknown
- 1986-07-30 KR KR1019860006255A patent/KR870001213A/ko not_active IP Right Cessation
- 1986-07-30 PL PL27011786A patent/PL270117A1/xx unknown
- 1986-07-30 PL PL1986260857A patent/PL260857A1/xx unknown
- 1986-07-30 AU AU60718/86A patent/AU604212B2/en not_active Expired - Fee Related
-
1988
- 1988-02-01 ES ES8800278A patent/ES2006546A6/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102180724B1 (ko) * | 2019-11-19 | 2020-11-19 | 김영찬 | 가공된 부엽토를 이용한 복합비료의 제조방법 및 이를 이용하여 제조된 복합비료 |
Also Published As
| Publication number | Publication date |
|---|---|
| DK360486D0 (da) | 1986-07-29 |
| DE3689392T2 (de) | 1994-05-26 |
| DK165448C (da) | 1993-04-13 |
| MC1756A1 (fr) | 1987-04-24 |
| PL270117A1 (en) | 1988-07-07 |
| DK360486A (da) | 1987-01-31 |
| AU6071886A (en) | 1987-02-05 |
| PT83086B (en) | 1988-07-13 |
| CN86105901A (zh) | 1987-03-11 |
| FI863091A0 (fi) | 1986-07-28 |
| PT83086A (en) | 1986-08-01 |
| EP0211598A3 (en) | 1988-08-17 |
| DE3689392D1 (de) | 1994-01-27 |
| DK165448B (da) | 1992-11-30 |
| PL260857A1 (en) | 1988-05-26 |
| IL79532A0 (en) | 1986-10-31 |
| AU604212B2 (en) | 1990-12-13 |
| ES2000778A6 (es) | 1988-03-16 |
| GR862011B (en) | 1986-12-23 |
| EP0211598B1 (en) | 1993-12-15 |
| FI863091L (fi) | 1987-01-31 |
| EP0211598A2 (en) | 1987-02-25 |
| ES2006546A6 (es) | 1989-05-01 |
| HUT41960A (en) | 1987-06-29 |
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