TW202379B - - Google Patents
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- TW202379B TW202379B TW074101429A TW74101429A TW202379B TW 202379 B TW202379 B TW 202379B TW 074101429 A TW074101429 A TW 074101429A TW 74101429 A TW74101429 A TW 74101429A TW 202379 B TW202379 B TW 202379B
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- TW
- Taiwan
- Prior art keywords
- compound
- formula
- item
- preparation
- propane
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 methylenedioxy phenyl group Chemical group 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 241000607479 Yersinia pestis Species 0.000 claims description 16
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000001294 propane Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 241000255925 Diptera Species 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 claims description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 150000004795 grignard reagents Chemical class 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- GFCCTYKSXKVOGY-UHFFFAOYSA-N BC(C)(C)CCC Chemical compound BC(C)(C)CCC GFCCTYKSXKVOGY-UHFFFAOYSA-N 0.000 claims description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 2
- 229910052704 radon Inorganic materials 0.000 claims 2
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 claims 2
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims 1
- 102100024092 Aldo-keto reductase family 1 member C4 Human genes 0.000 claims 1
- 101000690301 Homo sapiens Aldo-keto reductase family 1 member C4 Proteins 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000004888 barrier function Effects 0.000 claims 1
- 150000001639 boron compounds Chemical class 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000013043 chemical agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 238000004880 explosion Methods 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 238000009434 installation Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- YSZUKWLZJXGOTF-UHFFFAOYSA-N propane Chemical compound CCC.CCC YSZUKWLZJXGOTF-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000010117 shenhua Substances 0.000 claims 1
- 210000003625 skull Anatomy 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000004563 wettable powder Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 241001608567 Phaedon cochleariae Species 0.000 description 8
- 239000000575 pesticide Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 241000255777 Lepidoptera Species 0.000 description 5
- 241000257159 Musca domestica Species 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000256247 Spodoptera exigua Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- YXNVYZYRKHOSDJ-UHFFFAOYSA-N 1-cyclopropyl-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C1CC1 YXNVYZYRKHOSDJ-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000426499 Chilo Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- PVFTVTSMZMQOLM-UHFFFAOYSA-N cyclopropane;formaldehyde Chemical compound O=C.C1CC1 PVFTVTSMZMQOLM-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 230000001590 oxidative effect Effects 0.000 description 2
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 2
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
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- 231100000331 toxic Toxicity 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 1
- GVNQQZVYKCKTCR-UHFFFAOYSA-N 1-(2,2-difluorocyclopropyl)-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C1C(F)(F)C1 GVNQQZVYKCKTCR-UHFFFAOYSA-N 0.000 description 1
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- UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 1
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- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
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Classifications
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- 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
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
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- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
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- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
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- C—CHEMISTRY; METALLURGY
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- C07C43/02—Ethers
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C43/02—Ethers
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- C—CHEMISTRY; METALLURGY
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- C07C43/02—Ethers
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- C—CHEMISTRY; METALLURGY
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- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/457—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/47—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- 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
-
- 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
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
-
- 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
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/52—Radicals substituted by halogen atoms or nitro radicals
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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)
- 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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB848409195A GB8409195D0 (en) | 1984-04-09 | 1984-04-09 | Pesticides |
Publications (1)
Publication Number | Publication Date |
---|---|
TW202379B true TW202379B (en, 2012) | 1993-03-21 |
Family
ID=10559443
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW074101429A TW202379B (en, 2012) | 1984-04-09 | 1985-04-06 |
Country Status (34)
Country | Link |
---|---|
US (1) | US4777185A (en, 2012) |
EP (1) | EP0179788B1 (en, 2012) |
JP (1) | JPH0629200B2 (en, 2012) |
KR (1) | KR920002126B1 (en, 2012) |
AR (1) | AR240041A1 (en, 2012) |
AU (5) | AU584084B2 (en, 2012) |
BE (1) | BE902147A (en, 2012) |
BG (1) | BG46742A3 (en, 2012) |
BR (1) | BR8506438A (en, 2012) |
CA (1) | CA1337430C (en, 2012) |
CZ (1) | CZ281414B6 (en, 2012) |
DD (1) | DD238789A5 (en, 2012) |
DE (1) | DE3583205D1 (en, 2012) |
DK (2) | DK172189B1 (en, 2012) |
EG (1) | EG17870A (en, 2012) |
ES (3) | ES8705195A1 (en, 2012) |
GB (2) | GB8409195D0 (en, 2012) |
GR (1) | GR850875B (en, 2012) |
HU (1) | HU201219B (en, 2012) |
IE (1) | IE58692B1 (en, 2012) |
IL (1) | IL74721A (en, 2012) |
MX (1) | MX160841A (en, 2012) |
OA (1) | OA07988A (en, 2012) |
PH (1) | PH22357A (en, 2012) |
PL (1) | PL146599B1 (en, 2012) |
PT (1) | PT80230B (en, 2012) |
RO (1) | RO93563A (en, 2012) |
SK (1) | SK256785A3 (en, 2012) |
SU (1) | SU1549475A3 (en, 2012) |
TR (1) | TR25297A (en, 2012) |
TW (1) | TW202379B (en, 2012) |
WO (1) | WO1985004651A1 (en, 2012) |
ZA (1) | ZA852481B (en, 2012) |
ZW (1) | ZW6885A1 (en, 2012) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5248834A (en) * | 1984-04-09 | 1993-09-28 | British Technology Group Limited | Pesticides |
GB8409195D0 (en) * | 1984-04-09 | 1984-05-16 | Elliott M | Pesticides |
US5283371A (en) * | 1986-03-13 | 1994-02-01 | National Research Development Corporation | Intermediates useful in the production of pesticides |
WO1988008416A1 (en) * | 1987-04-23 | 1988-11-03 | Fmc Corporation | Insecticidal cyclopropyl-substituted di(aryl) compounds |
GB9219612D0 (en) * | 1992-09-16 | 1992-10-28 | Khambay Bhupinder P S | Pesticidal fluoroolefins |
GB9408605D0 (en) * | 1994-04-29 | 1994-06-22 | British Tech Group | Pesticidal fluoroolefins |
ZA974582B (en) * | 1996-06-03 | 1998-11-26 | American Cyanamid Co | Process and intermediate compounds for the preparation of pesticidal fluoroolefin compounds |
US7932410B2 (en) * | 2008-10-31 | 2011-04-26 | Bedoukian Research, Inc. | Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1570982A (en) * | 1976-03-05 | 1980-07-09 | Shell Int Research | Substituted benzyl ethers and thioethers |
US4242357A (en) * | 1976-04-09 | 1980-12-30 | Bayer Aktiengesellschaft | Carboxylic acid esters for combating pests |
US4152455A (en) * | 1977-02-02 | 1979-05-01 | Fmc Corporation | Insecticidal α-trifluoromethyl-3-phenoxybenzyl carboxylates |
JPS5764632A (en) * | 1980-10-09 | 1982-04-19 | Mitsui Toatsu Chem Inc | Novel 2-arylethyl ether derivative and thioether derivative, their production and insecticide and acaricide |
US4562213A (en) * | 1982-05-12 | 1985-12-31 | Sumitomo Chemical Company, Limited | Certain phenoxy-benzyloxy ether derivatives and an insecticidal and/or acaricidal composition containing the same and methods of use |
JPS58201737A (ja) * | 1982-05-18 | 1983-11-24 | Mitsui Toatsu Chem Inc | 新規芳香族アルカン誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
AU576307B2 (en) * | 1982-09-24 | 1988-08-25 | Commonwealth Scientific And Industrial Research Organisation | Arthropodicidal compounds |
EP0104908B1 (en) * | 1982-09-24 | 1990-12-27 | Commonwealth Scientific And Industrial Research Organisation | Arthropodicidal compounds |
EP0125204A1 (de) * | 1983-04-12 | 1984-11-14 | Ciba-Geigy Ag | 3-Phenoxybenzyl-(2-phenyl-2,2-alkylen-äthyl)-äther und -thioäther, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
DK181683A (da) * | 1983-04-25 | 1984-10-26 | Cheminova As | Arylcycloalkylether-derivater, deres anvendelse og fremstilling |
AU2827884A (en) * | 1983-04-25 | 1984-11-19 | Cheminova A/S | Arylcycloalkyl ether derivatives their use and preparation |
GB8409195D0 (en) * | 1984-04-09 | 1984-05-16 | Elliott M | Pesticides |
-
1984
- 1984-04-09 GB GB848409195A patent/GB8409195D0/en active Pending
-
1985
- 1985-03-26 IL IL74721A patent/IL74721A/xx not_active IP Right Cessation
- 1985-04-02 ZA ZA852481A patent/ZA852481B/xx unknown
- 1985-04-03 WO PCT/GB1985/000146 patent/WO1985004651A1/en active IP Right Grant
- 1985-04-03 EP EP85901517A patent/EP0179788B1/en not_active Expired - Lifetime
- 1985-04-03 AU AU42127/85A patent/AU584084B2/en not_active Ceased
- 1985-04-03 DE DE8585901517T patent/DE3583205D1/de not_active Expired - Lifetime
- 1985-04-03 PT PT80230A patent/PT80230B/pt unknown
- 1985-04-03 KR KR1019850700374A patent/KR920002126B1/ko not_active Expired
- 1985-04-03 BR BR8506438A patent/BR8506438A/pt not_active IP Right Cessation
- 1985-04-03 JP JP60501687A patent/JPH0629200B2/ja not_active Expired - Lifetime
- 1985-04-03 GB GB08528482A patent/GB2167749B/en not_active Expired
- 1985-04-03 RO RO85121082A patent/RO93563A/ro unknown
- 1985-04-03 HU HU86514A patent/HU201219B/hu not_active IP Right Cessation
- 1985-04-04 IE IE86085A patent/IE58692B1/en not_active IP Right Cessation
- 1985-04-04 ZW ZW68/85A patent/ZW6885A1/xx unknown
- 1985-04-04 CA CA000478363A patent/CA1337430C/en not_active Expired - Fee Related
- 1985-04-04 EG EG220/85A patent/EG17870A/xx active
- 1985-04-05 CZ CS852567A patent/CZ281414B6/cs not_active IP Right Cessation
- 1985-04-05 US US06/720,374 patent/US4777185A/en not_active Expired - Lifetime
- 1985-04-05 SK SK2567-85A patent/SK256785A3/sk unknown
- 1985-04-06 TW TW074101429A patent/TW202379B/zh active
- 1985-04-08 MX MX204882A patent/MX160841A/es unknown
- 1985-04-08 DD DD85274944A patent/DD238789A5/de unknown
- 1985-04-08 GR GR850875A patent/GR850875B/el not_active IP Right Cessation
- 1985-04-09 BE BE0/214809A patent/BE902147A/fr unknown
- 1985-04-09 TR TR85/18003A patent/TR25297A/xx unknown
- 1985-04-09 PH PH32110A patent/PH22357A/en unknown
- 1985-04-09 AR AR300009A patent/AR240041A1/es active
- 1985-04-09 OA OA58564A patent/OA07988A/xx unknown
- 1985-04-09 PL PL1985252847A patent/PL146599B1/pl unknown
- 1985-12-06 DK DK566985A patent/DK172189B1/da active
- 1985-12-06 SU SU853995752A patent/SU1549475A3/ru active
- 1985-12-09 BG BG072654A patent/BG46742A3/xx unknown
-
1986
- 1986-01-29 ES ES551379A patent/ES8705195A1/es not_active Expired
- 1986-01-29 ES ES551381A patent/ES8800127A1/es not_active Expired
- 1986-01-29 ES ES551380A patent/ES8705196A1/es not_active Expired
-
1989
- 1989-08-08 AU AU39359/89A patent/AU611579B2/en not_active Ceased
- 1989-08-08 AU AU39363/89A patent/AU613220B2/en not_active Ceased
- 1989-08-08 AU AU39364/89A patent/AU614654B2/en not_active Ceased
- 1989-08-08 AU AU39362/89A patent/AU611822B2/en not_active Ceased
-
1992
- 1992-05-26 DK DK199200698A patent/DK172479B1/da active
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