DK168765B1 - Hidtil ukendte 1,4-bis-substituerede-2,6,7-trioxabicyclo(2.2.2)octaner, pesticid omfattende en sådan octan, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige organismer samt fremgangsmåde til fremstilling af octanerne - Google Patents
Hidtil ukendte 1,4-bis-substituerede-2,6,7-trioxabicyclo(2.2.2)octaner, pesticid omfattende en sådan octan, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige organismer samt fremgangsmåde til fremstilling af octanerne Download PDFInfo
- Publication number
- DK168765B1 DK168765B1 DK440285A DK440285A DK168765B1 DK 168765 B1 DK168765 B1 DK 168765B1 DK 440285 A DK440285 A DK 440285A DK 440285 A DK440285 A DK 440285A DK 168765 B1 DK168765 B1 DK 168765B1
- Authority
- DK
- Denmark
- Prior art keywords
- pesticide
- compound
- octanes
- substituted
- butyl
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title claims description 33
- -1 1,4-bis-substituted-2,6,7- trioxabicyclo[2.2.2]octanes Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 19
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 230000000505 pernicious effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 48
- 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 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical group C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 17
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 17
- 241000238631 Hexapoda Species 0.000 claims description 13
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
- 241000257159 Musca domestica Species 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000000361 pesticidal effect Effects 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 238000001784 detoxification Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007171 acid catalysis Methods 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- PQZJTHGEFIQMCO-UHFFFAOYSA-N oxetan-2-ylmethanol Chemical class OCC1CCO1 PQZJTHGEFIQMCO-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 241000257226 Muscidae Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 6
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- VTUKKVHSZDBIPA-UHFFFAOYSA-N 3,5,8-trioxabicyclo[2.2.2]octane Chemical class O1CC2COC1OC2 VTUKKVHSZDBIPA-UHFFFAOYSA-N 0.000 description 4
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- 238000005481 NMR spectroscopy Methods 0.000 description 4
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- 238000002474 experimental method Methods 0.000 description 4
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- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 241000699670 Mus sp. Species 0.000 description 3
- 241000238675 Periplaneta americana Species 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 231100001225 mammalian toxicity Toxicity 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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- 241000256113 Culicidae Species 0.000 description 2
- 244000207543 Euphorbia heterophylla Species 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- 235000019256 formaldehyde Nutrition 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 231100000041 toxicology testing Toxicity 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- FMUFFUZPAMYTLG-UHFFFAOYSA-N (3-propan-2-yloxetan-3-yl)methanol Chemical compound CC(C)C1(CO)COC1 FMUFFUZPAMYTLG-UHFFFAOYSA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- KDHYEQYWOYBACO-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propan-2-ylpropane-1,3-diol Chemical compound CC(C)C(CO)(CO)CO KDHYEQYWOYBACO-UHFFFAOYSA-N 0.000 description 1
- BNEQHTNDYHYJFK-UHFFFAOYSA-N 2-tert-butyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CC(C)(C)C(CO)(CO)CO BNEQHTNDYHYJFK-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
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- 241000208327 Apocynaceae Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 108010045510 NADPH-Ferrihemoprotein Reductase Proteins 0.000 description 1
- 241000258914 Oncopeltus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical class C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000002759 chromosomal effect Effects 0.000 description 1
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- 230000000052 comparative effect Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006199 crossed Cannizzaro oxidation reduction reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000007031 hydroxymethylation reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002560 ketene acetals Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- FCTSPUZGCMHTFO-UHFFFAOYSA-N phenyl(prop-2-ynoxy)phosphinic acid Chemical compound C#CCOP(=O)(O)C1=CC=CC=C1 FCTSPUZGCMHTFO-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical group [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- MVDRXYIEGOGRAI-UHFFFAOYSA-N tribromomethylbenzene Chemical compound BrC(Br)(Br)C1=CC=CC=C1 MVDRXYIEGOGRAI-UHFFFAOYSA-N 0.000 description 1
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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
- C07D493/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57584384A | 1984-01-30 | 1984-01-30 | |
| US57584384 | 1984-01-30 | ||
| US69281885A | 1985-01-23 | 1985-01-23 | |
| US69281885 | 1985-01-23 | ||
| PCT/US1985/000150 WO1985003203A1 (en) | 1984-01-30 | 1985-01-29 | A new class of pesticides comprising 1,4-bis-substituted-2,6,7-trioxabicyclo ad2.2.2. bd octanes |
| US8500150 | 1985-01-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK440285D0 DK440285D0 (da) | 1985-09-27 |
| DK440285A DK440285A (da) | 1985-11-27 |
| DK168765B1 true DK168765B1 (da) | 1994-06-06 |
Family
ID=27076803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK440285A DK168765B1 (da) | 1984-01-30 | 1985-09-27 | Hidtil ukendte 1,4-bis-substituerede-2,6,7-trioxabicyclo(2.2.2)octaner, pesticid omfattende en sådan octan, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadelige organismer samt fremgangsmåde til fremstilling af octanerne |
Country Status (9)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8523582D0 (en) * | 1985-09-24 | 1985-10-30 | Wellcome Found | Insecticidal compounds |
| GB8519212D0 (en) * | 1985-07-30 | 1985-09-04 | Wellcome Found | Pesticidal compound |
| US5098929A (en) * | 1985-07-30 | 1992-03-24 | The Wellcome Foundation Limited | Pesticidal compounds |
| FI863091L (fi) | 1985-07-30 | 1987-01-31 | Wellcome Found | Pesticida foereningar. |
| MC1767A1 (fr) * | 1985-09-23 | 1987-07-17 | Wellcome Found | Composes pesticides,procedes pour leur preparation et composition insecticide ou acaricide,composition pesticide synergisee et melange en contenant |
| EP0216625A3 (en) * | 1985-09-24 | 1988-08-17 | The Wellcome Foundation Limited | Pesticidal compounds |
| US5116862A (en) * | 1985-09-24 | 1992-05-26 | The Wellcome Foundation Limited | Pesticidal compounds |
| GR862418B (en) * | 1985-09-24 | 1987-01-23 | Wellcome Found | Pesticidal compounds |
| GB8603383D0 (en) * | 1986-02-11 | 1986-03-19 | Wellcome Found | Pesticidal formulations |
| EP0243184A3 (en) * | 1986-04-25 | 1989-05-10 | Roussel-Uclaf | Pesticidal compounds |
| FI883453A7 (fi) * | 1987-07-22 | 1989-01-23 | Wellcome Found | Bicyklooktanderivat anvaendbara som pesticider och foerfarande foer deras framstaellning. |
| 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 |
| US8152798B2 (en) * | 2005-10-31 | 2012-04-10 | Novartis Ag | Surgical variable-angle illuminator |
| TWI550071B (zh) | 2011-03-25 | 2016-09-21 | 捷恩智股份有限公司 | 原酸酯化合物、液晶組成物及液晶顯示元件 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI863091L (fi) * | 1985-07-30 | 1987-01-31 | Wellcome Found | Pesticida foereningar. |
| MC1767A1 (fr) * | 1985-09-23 | 1987-07-17 | Wellcome Found | Composes pesticides,procedes pour leur preparation et composition insecticide ou acaricide,composition pesticide synergisee et melange en contenant |
| EP0216625A3 (en) * | 1985-09-24 | 1988-08-17 | The Wellcome Foundation Limited | Pesticidal compounds |
-
1985
- 1985-01-29 HU HU851068A patent/HU198828B/hu not_active IP Right Cessation
- 1985-01-29 AU AU39332/85A patent/AU3933285A/en not_active Abandoned
- 1985-01-29 JP JP60500578A patent/JPH0623082B2/ja not_active Expired - Lifetime
- 1985-01-29 WO PCT/US1985/000150 patent/WO1985003203A1/en unknown
- 1985-01-30 DE DE85300619T patent/DE3585886D1/de not_active Expired - Lifetime
- 1985-01-30 EP EP85300619A patent/EP0152229B1/en not_active Expired - Lifetime
- 1985-01-30 EG EG56/85A patent/EG17617A/xx active
- 1985-02-11 IL IL74293A patent/IL74293A/xx not_active IP Right Cessation
- 1985-09-27 DK DK440285A patent/DK168765B1/da not_active IP Right Cessation
-
1989
- 1989-02-13 AU AU29892/89A patent/AU615986B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IL74293A0 (en) | 1988-12-30 |
| EG17617A (en) | 1990-08-30 |
| WO1985003203A1 (en) | 1985-08-01 |
| AU3933285A (en) | 1985-08-09 |
| EP0152229B1 (en) | 1992-04-22 |
| IL74293A (en) | 1992-12-01 |
| EP0152229A2 (en) | 1985-08-21 |
| JPS61501149A (ja) | 1986-06-12 |
| DK440285D0 (da) | 1985-09-27 |
| EP0152229A3 (en) | 1985-12-04 |
| AU615986B2 (en) | 1991-10-17 |
| JPH0623082B2 (ja) | 1994-03-30 |
| AU2989289A (en) | 1989-06-29 |
| HU198828B (en) | 1989-12-28 |
| DK440285A (da) | 1985-11-27 |
| HUT38034A (en) | 1986-04-28 |
| DE3585886D1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-05-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |