DE2500344A1 - Verbindungen mit einer ungesaettigten aliphatischen kette, verfahren zu deren herstellung sowie insektizid mit juvenilhormonwirkung - Google Patents
Verbindungen mit einer ungesaettigten aliphatischen kette, verfahren zu deren herstellung sowie insektizid mit juvenilhormonwirkungInfo
- Publication number
- DE2500344A1 DE2500344A1 DE19752500344 DE2500344A DE2500344A1 DE 2500344 A1 DE2500344 A1 DE 2500344A1 DE 19752500344 DE19752500344 DE 19752500344 DE 2500344 A DE2500344 A DE 2500344A DE 2500344 A1 DE2500344 A1 DE 2500344A1
- Authority
- DE
- Germany
- Prior art keywords
- dichloro
- formula
- methyl
- chr
- hepta
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000002917 insecticide Substances 0.000 title claims description 4
- 230000000694 effects Effects 0.000 title description 4
- 239000000460 chlorine Substances 0.000 claims description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 43
- -1 carbalkyl Chemical group 0.000 claims description 40
- 229910052801 chlorine Chemical group 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 230000008030 elimination Effects 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 6
- 239000012991 xanthate Substances 0.000 claims description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000001993 dienes Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229930014550 juvenile hormone Natural products 0.000 claims description 4
- 239000002949 juvenile hormone Substances 0.000 claims description 4
- 150000003633 juvenile hormone derivatives Chemical class 0.000 claims description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229940095102 methyl benzoate Drugs 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
- XRNDWADRKXEWDV-UHFFFAOYSA-N 1-(6,6-dichloro-3-methylhexa-2,5-dienoxy)-4-ethylbenzene Chemical compound CCC1=CC=C(OCC=C(C)CC=C(Cl)Cl)C=C1 XRNDWADRKXEWDV-UHFFFAOYSA-N 0.000 claims description 2
- ABRFENSXMQRPPK-UHFFFAOYSA-N 10,10-dichloro-6-methyldeca-5,9-dien-2-one Chemical compound CC(=O)CCC=C(C)CCC=C(Cl)Cl ABRFENSXMQRPPK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000004715 keto acids Chemical class 0.000 claims 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims 2
- GAUKRSRSBNZYSW-UHFFFAOYSA-N 1-(7,7-dichloro-3-methylhepta-2,6-dienoxy)-4-methylbenzene Chemical compound ClC(Cl)=CCCC(C)=CCOC1=CC=C(C)C=C1 GAUKRSRSBNZYSW-UHFFFAOYSA-N 0.000 claims 1
- BFQOMMPRZUAGOM-UHFFFAOYSA-N 1-chloro-4-(6,6-dichloro-3-methylhexa-2,5-dienoxy)benzene Chemical compound ClC(Cl)=CCC(C)=CCOC1=CC=C(Cl)C=C1 BFQOMMPRZUAGOM-UHFFFAOYSA-N 0.000 claims 1
- FVYCLQLRCSBALF-UHFFFAOYSA-N 1-chloro-4-(7,7-dichloro-3-ethylhepta-2,6-dienoxy)benzene Chemical compound ClC(Cl)=CCCC(CC)=CCOC1=CC=C(Cl)C=C1 FVYCLQLRCSBALF-UHFFFAOYSA-N 0.000 claims 1
- KLZFYSOJLVWXKH-UHFFFAOYSA-N 1-chloro-4-(7,7-dichloro-3-methylhepta-2,6-dienoxy)benzene Chemical compound ClC(Cl)=CCCC(C)=CCOC1=CC=C(Cl)C=C1 KLZFYSOJLVWXKH-UHFFFAOYSA-N 0.000 claims 1
- QYYLJUHZOAJIID-UHFFFAOYSA-N 3-(7,7-dichloro-3-methylhepta-2,6-dienoxy)benzonitrile Chemical compound ClC(Cl)=CCCC(C)=CCOC1=CC=CC(C#N)=C1 QYYLJUHZOAJIID-UHFFFAOYSA-N 0.000 claims 1
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 claims 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 101001093181 Homo sapiens Short coiled-coil protein Proteins 0.000 claims 1
- 102100036292 Short coiled-coil protein Human genes 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 106
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 35
- 241000238631 Hexapoda Species 0.000 description 33
- 239000000047 product Substances 0.000 description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 238000009835 boiling Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 235000013601 eggs Nutrition 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 229940035423 ethyl ether Drugs 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 10
- 235000013312 flour Nutrition 0.000 description 10
- 238000010183 spectrum analysis Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 235000000346 sugar Nutrition 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical class CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 6
- 241000256111 Aedes <genus> Species 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000017448 oviposition Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- JAGYXYUAYDLKNO-GGWOSOGESA-N (2e,5e)-hepta-2,5-diene Chemical compound C\C=C\C\C=C\C JAGYXYUAYDLKNO-GGWOSOGESA-N 0.000 description 1
- RJDXPVXKAUSDFR-GORDUTHDSA-N (e)-1,5,5,5-tetrachloro-2-methylpent-2-ene Chemical compound ClCC(/C)=C/CC(Cl)(Cl)Cl RJDXPVXKAUSDFR-GORDUTHDSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 description 1
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 description 1
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 1
- DIYFNUALHGQFRM-UHFFFAOYSA-N 1,5-dichlorocyclohexa-2,4-dien-1-ol Chemical compound OC1(Cl)CC(Cl)=CC=C1 DIYFNUALHGQFRM-UHFFFAOYSA-N 0.000 description 1
- YVXCWOMGXGCNPU-UHFFFAOYSA-N 1-(7,7-dichloro-3-ethylhepta-2,6-dienoxy)-4-ethylbenzene Chemical compound ClC(Cl)=CCCC(CC)=CCOC1=CC=C(CC)C=C1 YVXCWOMGXGCNPU-UHFFFAOYSA-N 0.000 description 1
- AUYGWEXGGAKPCB-UHFFFAOYSA-N 1-(7,7-dichloro-3-methylhepta-2,6-dienoxy)-3-methoxybenzene Chemical compound COC1=CC=CC(OCC=C(C)CCC=C(Cl)Cl)=C1 AUYGWEXGGAKPCB-UHFFFAOYSA-N 0.000 description 1
- XBXWOIBGILYCEK-UHFFFAOYSA-N 1-(7,7-dichloro-3-methylhepta-2,6-dienoxy)-4-ethylbenzene Chemical compound CCC1=CC=C(OCC=C(C)CCC=C(Cl)Cl)C=C1 XBXWOIBGILYCEK-UHFFFAOYSA-N 0.000 description 1
- QWYBUUQNPHDHLH-UHFFFAOYSA-N 1-(7,7-dichloro-3-methylhepta-2,6-dienoxy)-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(OCC=C(C)CCC=C(Cl)Cl)C=C1 QWYBUUQNPHDHLH-UHFFFAOYSA-N 0.000 description 1
- OWXJKYNZGFSVRC-UHFFFAOYSA-N 1-chloroprop-1-ene Chemical compound CC=CCl OWXJKYNZGFSVRC-UHFFFAOYSA-N 0.000 description 1
- PQUUGVDRLWLNGR-UHFFFAOYSA-N 2,3,3,3-tetrachloroprop-1-ene Chemical compound ClC(=C)C(Cl)(Cl)Cl PQUUGVDRLWLNGR-UHFFFAOYSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- BBMFSGOFUHEVNP-UHFFFAOYSA-N 4-hydroxy-2-methylbenzoic acid Chemical compound CC1=CC(O)=CC=C1C(O)=O BBMFSGOFUHEVNP-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 description 1
- RRVMEHNSKCBEBH-UHFFFAOYSA-N 5-(7,7-dichloro-3-methylhepta-2,6-dienoxy)-1,3-benzodioxole Chemical compound ClC(Cl)=CCCC(C)=CCOC1=CC=C2OCOC2=C1 RRVMEHNSKCBEBH-UHFFFAOYSA-N 0.000 description 1
- WXXPXOUDTUQTFW-UHFFFAOYSA-N 6-bromo-1,1-dichloro-4-methylhexa-1,4-diene Chemical compound BrCC=C(C)CC=C(Cl)Cl WXXPXOUDTUQTFW-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- ITXTWOWZLBAEJG-UHFFFAOYSA-N 7,7-dichloro-3-ethylhepta-1,6-dien-3-ol Chemical compound CCC(O)(C=C)CCC=C(Cl)Cl ITXTWOWZLBAEJG-UHFFFAOYSA-N 0.000 description 1
- JIWHRQNFYGNLGF-UHFFFAOYSA-N 7-bromo-1,1-dichloro-5-ethylhepta-1,5-diene Chemical compound BrCC=C(CC)CCC=C(Cl)Cl JIWHRQNFYGNLGF-UHFFFAOYSA-N 0.000 description 1
- OBMOSDAZVSFIGQ-UHFFFAOYSA-N 7-bromo-1,1-dichloro-5-methylhepta-1,5-diene Chemical compound BrCC=C(C)CCC=C(Cl)Cl OBMOSDAZVSFIGQ-UHFFFAOYSA-N 0.000 description 1
- FWHAXCIOWCISRY-UHFFFAOYSA-N 8,8-dichloroocta-5,7-dien-2-one Chemical compound CC(=O)CCC=CC=C(Cl)Cl FWHAXCIOWCISRY-UHFFFAOYSA-N 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 101100070104 Mus musculus Hacl1 gene Proteins 0.000 description 1
- UOJYYXATTMQQNA-UHFFFAOYSA-N Proxan Chemical compound CC(C)OC(S)=S UOJYYXATTMQQNA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- VZZBCNXVZFAIQX-UHFFFAOYSA-N bms-986260 Chemical compound ClC=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)CCO VZZBCNXVZFAIQX-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- UDRCONFHWYGWFI-UHFFFAOYSA-N ethyl 3-oxopentanoate Chemical compound CCOC(=O)CC(=O)CC UDRCONFHWYGWFI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1933274A IT1049216B (it) | 1974-01-11 | 1974-01-11 | Sostanze contenenti una catena alifatica insatura ad azione insetticida ed inibente lo sviluppo e la metamorfosi degli insetti e loro procedimento di preparazione |
| IT2858374A IT1046148B (it) | 1974-10-18 | 1974-10-18 | Sostanze contenenti una catena alifatica insatura ad azione insetticida ed inibente lo sviluppo e la metamorfosi degli insetti e loro procedimento di preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2500344A1 true DE2500344A1 (de) | 1975-07-17 |
Family
ID=26327137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752500344 Withdrawn DE2500344A1 (de) | 1974-01-11 | 1975-01-07 | Verbindungen mit einer ungesaettigten aliphatischen kette, verfahren zu deren herstellung sowie insektizid mit juvenilhormonwirkung |
Country Status (6)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1043239B (it) * | 1975-10-09 | 1980-02-20 | Montedison Spa | Composti a gruppo terminale tri clorometilico aventi azione ormonica giovanile sugli insetti dotati di attivita acaricida |
| US5786504A (en) * | 1996-05-15 | 1998-07-28 | Uniroyal Chemical Company, Inc. | Polymerization catalyst promoter |
| PT2231565E (pt) | 2007-12-19 | 2014-06-11 | Occidental Chem Co | Métodos de fabrico de hidrocarbonetos clorados |
| JP2010248104A (ja) * | 2009-04-14 | 2010-11-04 | Tokuyama Corp | １，１，１，２，３−ペンタクロロプロパンの製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2613221A (en) * | 1948-04-30 | 1952-10-07 | Us Rubber Co | Preparing polyhalogenoalkenyl compounds |
| DE1285996B (de) * | 1966-09-14 | 1969-01-02 | Basf Ag | Verfahren zur Herstellung von 2, 3, 3-Trichloracrolein |
| FR1600695A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-12-31 | 1970-07-27 | ||
| DE1922413A1 (de) * | 1969-05-02 | 1970-11-05 | Basf Ag | Halogenacrylsaeurederivate enthaltende Herbizide |
| FR2109485A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-10-21 | 1972-05-26 | Rhone Progil | |
| US3755411A (en) * | 1971-02-01 | 1973-08-28 | Zoecon Corp | Halo or oxy substituted aliphatic di olefinic nitriles |
-
1975
- 1975-01-03 NL NL7500046A patent/NL7500046A/xx not_active Application Discontinuation
- 1975-01-07 DE DE19752500344 patent/DE2500344A1/de not_active Withdrawn
- 1975-01-10 US US05/540,167 patent/US4000312A/en not_active Expired - Lifetime
- 1975-01-10 FR FR7500650A patent/FR2257558B1/fr not_active Expired
- 1975-01-10 JP JP50005061A patent/JPS50121208A/ja active Pending
- 1975-01-13 GB GB1366/75A patent/GB1497570A/en not_active Expired
-
1977
- 1977-12-29 FR FR7739567A patent/FR2374289A1/fr not_active Withdrawn
- 1977-12-29 FR FR7739566A patent/FR2374294A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL7500046A (nl) | 1975-07-15 |
| FR2374289A1 (fr) | 1978-07-13 |
| FR2374294A1 (fr) | 1978-07-13 |
| FR2257558B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-08-07 |
| FR2257558A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-08 |
| US4000312A (en) | 1976-12-28 |
| JPS50121208A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-23 |
| GB1497570A (en) | 1978-01-12 |
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