JPH0361666B2 - - Google Patents
Info
- Publication number
- JPH0361666B2 JPH0361666B2 JP59101625A JP10162584A JPH0361666B2 JP H0361666 B2 JPH0361666 B2 JP H0361666B2 JP 59101625 A JP59101625 A JP 59101625A JP 10162584 A JP10162584 A JP 10162584A JP H0361666 B2 JPH0361666 B2 JP H0361666B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- formula
- substituted
- alkyl
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 23
- 150000003852 triazoles Chemical class 0.000 claims abstract description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 6
- BHESZOICBTWRPK-UHFFFAOYSA-N 4-[1-[1-(2h-triazol-4-yl)ethoxy]ethyl]-2h-triazole Chemical class C=1NN=NC=1C(C)OC(C)C1=CNN=N1 BHESZOICBTWRPK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003377 acid catalyst Substances 0.000 claims abstract description 5
- 229910052751 metal Chemical group 0.000 claims abstract description 4
- 239000002184 metal Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 83
- 238000004519 manufacturing process Methods 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
- -1 halophenoxy group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000006277 halobenzyl group Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 150000002148 esters Chemical class 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000011230 binding agent Substances 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 125000003118 aryl group Chemical group 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 239000003208 petroleum Substances 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 24
- 229910002027 silica gel Inorganic materials 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 238000000921 elemental analysis Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 239000012230 colorless oil Substances 0.000 description 17
- 239000012467 final product Substances 0.000 description 17
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 159000000000 sodium salts Chemical class 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 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 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 150000003509 tertiary alcohols Chemical class 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 5
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 230000003641 microbiacidal effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- HAKOFSDOQLDZBZ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-propyloxirane Chemical compound C=1C=C(Cl)C=C(Cl)C=1C1(CCC)CO1 HAKOFSDOQLDZBZ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- SSMDZKBRISDURT-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-methoxypentan-1-ol Chemical compound CCCC(CO)(OC)C1=CC=C(Cl)C=C1Cl SSMDZKBRISDURT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229940124561 microbicide Drugs 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BXSOQSOCBKWJLT-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-propan-2-yloxypentyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)(OC(C)C)CN1C=NC=N1 BXSOQSOCBKWJLT-UHFFFAOYSA-N 0.000 description 2
- IYTVJXCMDVQMKO-UHFFFAOYSA-N 1-butyl-2,4-dichlorobenzene Chemical compound CCCCC1=CC=C(Cl)C=C1Cl IYTVJXCMDVQMKO-UHFFFAOYSA-N 0.000 description 2
- ANHYRIRINAFJPT-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-propan-2-yloxypentan-1-ol Chemical compound CCCC(CO)(OC(C)C)C1=CC=C(Cl)C=C1Cl ANHYRIRINAFJPT-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003943 azolyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- QEHXDOJPVIHUDO-UHFFFAOYSA-N (2-fluorophenyl)methanol Chemical compound OCC1=CC=CC=C1F QEHXDOJPVIHUDO-UHFFFAOYSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- OJTBQXZLANYDLF-UHFFFAOYSA-N 1-(2-methoxyethoxy)pentane Chemical compound CCCCCOCCOC OJTBQXZLANYDLF-UHFFFAOYSA-N 0.000 description 1
- ONWBAHCUYAVODA-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-ethoxypentyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)(OCC)CN1C=NC=N1 ONWBAHCUYAVODA-UHFFFAOYSA-N 0.000 description 1
- HKIWVIQHCFPTFJ-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-methoxybutyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CC)(OC)CN1C=NC=N1 HKIWVIQHCFPTFJ-UHFFFAOYSA-N 0.000 description 1
- YIRNQCBBRNXIQV-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-methoxypentyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)(OC)CN1C=NC=N1 YIRNQCBBRNXIQV-UHFFFAOYSA-N 0.000 description 1
- PMIJMRNVBADJFQ-UHFFFAOYSA-N 1-[2-butoxy-2-(4-fluorophenyl)propyl]-1,2,4-triazole Chemical compound C=1C=C(F)C=CC=1C(C)(OCCCC)CN1C=NC=N1 PMIJMRNVBADJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- VXDAYEQIKPBCMA-UHFFFAOYSA-N 2,4-dichloro-1-pentylbenzene Chemical compound CCCCCC1=CC=C(Cl)C=C1Cl VXDAYEQIKPBCMA-UHFFFAOYSA-N 0.000 description 1
- ASFCNYFBNGYXOW-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-(2-methoxyethoxy)pentan-1-ol Chemical compound COCCOC(CO)(CCC)C1=CC=C(Cl)C=C1Cl ASFCNYFBNGYXOW-UHFFFAOYSA-N 0.000 description 1
- ZPHLOTXTOAYCBR-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-[(2-fluorophenyl)methoxy]pentan-1-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CO)(CCC)OCC1=CC=CC=C1F ZPHLOTXTOAYCBR-UHFFFAOYSA-N 0.000 description 1
- XDROQJIPODXCMY-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-ethoxypentan-1-ol Chemical compound CCCC(CO)(OCC)C1=CC=C(Cl)C=C1Cl XDROQJIPODXCMY-UHFFFAOYSA-N 0.000 description 1
- USPDYOUEBWSTFD-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-methoxybutan-1-ol Chemical compound CCC(CO)(OC)C1=CC=C(Cl)C=C1Cl USPDYOUEBWSTFD-UHFFFAOYSA-N 0.000 description 1
- QPMKKBOWFYRTKN-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-propoxybutan-1-ol Chemical compound CCCOC(CC)(CO)C1=CC=C(Cl)C=C1Cl QPMKKBOWFYRTKN-UHFFFAOYSA-N 0.000 description 1
- IWBNMSJHMZPROE-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-propoxypentan-1-ol Chemical compound CCCOC(CO)(CCC)C1=CC=C(Cl)C=C1Cl IWBNMSJHMZPROE-UHFFFAOYSA-N 0.000 description 1
- PASVNUFCKZMCHY-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-methyloxirane Chemical compound C=1C=C(F)C=CC=1C1(C)CO1 PASVNUFCKZMCHY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- BSCFIWHJBMWXAD-UHFFFAOYSA-N 2-butoxy-2-(4-fluorophenyl)propan-1-ol Chemical compound CCCCOC(C)(CO)C1=CC=C(F)C=C1 BSCFIWHJBMWXAD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- 229910015844 BCl3 Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- ONPDEBLRQGFEIV-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-2-methoxybutyl] methanesulfonate Chemical compound CS(=O)(=O)OCC(CC)(OC)C1=CC=C(Cl)C=C1Cl ONPDEBLRQGFEIV-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N isourea group Chemical group NC(O)=N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002855 microbicide agent Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- DISPOJHKKXSCLS-UHFFFAOYSA-N n-diaminophosphorylmethanamine Chemical compound CNP(N)(N)=O DISPOJHKKXSCLS-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940035637 spectrum-4 Drugs 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (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)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2730/83-7 | 1983-05-19 | ||
| CH273083 | 1983-05-19 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1112794A Division JPH0285265A (ja) | 1983-05-19 | 1989-05-01 | ジフェニルエーテル基を含む新規トリアゾリル誘導体及び殺微生物剤組成物 |
| JP1112793A Division JPH0296544A (ja) | 1983-05-19 | 1989-05-01 | グリコールモノエーテル及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59222434A JPS59222434A (ja) | 1984-12-14 |
| JPH0361666B2 true JPH0361666B2 (enExample) | 1991-09-20 |
Family
ID=4240315
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59101625A Granted JPS59222434A (ja) | 1983-05-19 | 1984-05-19 | １―トリアゾリルエチルエーテル誘導体の製造方法 |
| JP1112794A Granted JPH0285265A (ja) | 1983-05-19 | 1989-05-01 | ジフェニルエーテル基を含む新規トリアゾリル誘導体及び殺微生物剤組成物 |
| JP1112793A Granted JPH0296544A (ja) | 1983-05-19 | 1989-05-01 | グリコールモノエーテル及びその製造方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1112794A Granted JPH0285265A (ja) | 1983-05-19 | 1989-05-01 | ジフェニルエーテル基を含む新規トリアゾリル誘導体及び殺微生物剤組成物 |
| JP1112793A Granted JPH0296544A (ja) | 1983-05-19 | 1989-05-01 | グリコールモノエーテル及びその製造方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4945100A (enExample) |
| EP (1) | EP0126430B1 (enExample) |
| JP (3) | JPS59222434A (enExample) |
| KR (2) | KR890000533B1 (enExample) |
| AT (1) | ATE66676T1 (enExample) |
| AU (2) | AU572145B2 (enExample) |
| BR (1) | BR8402388A (enExample) |
| CA (1) | CA1223264A (enExample) |
| CS (2) | CS247179B2 (enExample) |
| DD (2) | DD248274A5 (enExample) |
| DE (1) | DE3484968D1 (enExample) |
| DK (1) | DK248184A (enExample) |
| ES (1) | ES8600635A1 (enExample) |
| GB (2) | GB2143815B (enExample) |
| GR (1) | GR79954B (enExample) |
| HU (1) | HU196693B (enExample) |
| IE (2) | IE57488B1 (enExample) |
| IL (3) | IL71862A (enExample) |
| MX (1) | MX5769A (enExample) |
| MY (1) | MY102774A (enExample) |
| NZ (2) | NZ208209A (enExample) |
| PH (3) | PH20959A (enExample) |
| PT (1) | PT78602A (enExample) |
| TR (1) | TR22379A (enExample) |
| ZA (1) | ZA843774B (enExample) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2143815B (en) * | 1983-05-19 | 1988-01-20 | Ciba Geigy Ag | Process for the preparation of micro biocidal 1-triazolylethyl ether derivatives |
| GB2156807A (en) * | 1984-04-05 | 1985-10-16 | Ici Plc | Azolyl propanols |
| DE3682023D1 (de) * | 1985-08-07 | 1991-11-21 | Ici Plc | Triazolylmethyl-tert.-butyl-carbinolderivate, verfahren zu ihrer herstellung und ihre verwendung als planzenwachstumsregulatoren. |
| GB8603951D0 (en) * | 1986-02-18 | 1986-03-26 | Ici Plc | Heterocyclic compounds |
| EP0275955B1 (de) * | 1987-01-21 | 1990-07-04 | Ciba-Geigy Ag | Mikrobizides Mittel |
| DE3732387A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Azolylmethylcyclopropyl-derivate enthaltende antimykotische mittel |
| DE58903329D1 (de) * | 1988-08-04 | 1993-03-04 | Ciba Geigy Ag | Mikrobizide mittel. |
| US4940720A (en) * | 1989-08-02 | 1990-07-10 | Ciba-Geigy Corporation | Microbicidal compositions |
| US5358939A (en) * | 1992-06-25 | 1994-10-25 | Rohm And Haas Company | Fungicidal 2-aryl-2,2-disubstituted ethyl-1,2,4-triazoles |
| NZ270418A (en) | 1994-02-07 | 1997-09-22 | Eisai Co Ltd | Polycyclic triazole & imidazole derivatives, antifungal compositions |
| KR20020037652A (ko) * | 2000-11-15 | 2002-05-22 | 김응필 | 비중분리 선광기 |
| JP5260540B2 (ja) | 2006-11-22 | 2013-08-14 | ビーエーエスエフ ソシエタス・ヨーロピア | 液体水性農芸化学製剤 |
| PT2184993E (pt) | 2007-08-08 | 2011-12-19 | Basf Se | Microemulsões aquosas contendo compostos inseticidas orgânicos |
| EP2309847A2 (de) * | 2008-07-24 | 2011-04-20 | Basf Se | Öl-in-wasser emulsion umfassend lösungsmittel, wasser, tensid und pestizid |
| TW201018400A (en) | 2008-10-10 | 2010-05-16 | Basf Se | Liquid aqueous plant protection formulations |
| UA106213C2 (ru) | 2008-10-10 | 2014-08-11 | Басф Се | Жидкие препараты для защиты растений, содержащие пираклостробин |
| PE20140826A1 (es) * | 2011-07-13 | 2014-07-09 | Basf Se | Compuestos sustituidos fungicidas de 2-[2-halogenalquil-4-(fenoxi)-fenil]-1-[1,2,4]triazol-1-il-etanol |
| BR112014000821A2 (pt) | 2011-07-15 | 2016-08-23 | Basf Se | compostos, processo, composições agroquímicas, uso de compostos da fórmula i, método para combate de fungos nocivos e semente |
| WO2013010885A1 (en) | 2011-07-15 | 2013-01-24 | Basf Se | Fungicidal alkyl- and aryl-substituted 2-[2-chloro-4-(dihalo-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
| AU2012285981A1 (en) * | 2011-07-15 | 2014-01-30 | Basf Se | Fungicidal alkyl-substituted 2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
| UY34261A (es) * | 2011-08-15 | 2013-02-28 | Basf Se | Compuestos fungicidas de 1-{2-[2-halo-4-(4-halogen-fenoxi)-fenil]-2-alcoxi-2-ciclil-etil}-1h-[1,2,4]triazol sustituidos |
| EP2744791B1 (en) * | 2011-08-15 | 2015-10-28 | Basf Se | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-3-methyl-butyl}-1h-[1,2,4]triazole compounds |
| KR20140054236A (ko) | 2011-08-15 | 2014-05-08 | 바스프 에스이 | 살진균 치환된 1-｛2-［2-할로-4-(4-할로겐-페녹시)-페닐］-2-에톡시-에틸｝-1h-［1,2,4］트리아졸 화합물 |
| AR087538A1 (es) | 2011-08-15 | 2014-04-03 | Basf Se | Compuestos fungicidas de 1-{2-[2-halo-4-(4-halogen-fenoxi)-fenil]-2-alcoxi-2-alquinil/alquenil-etil}-1h-[1,2,4]triazol sustituidos |
| JP2014525404A (ja) * | 2011-08-15 | 2014-09-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌性置換１−｛２−［２−ハロ−４−（４−ハロゲン−フェノキシ）−フェニル］−２−アルキニルオキシ−エチル｝−１ｈ−［１，２，４］トリアゾール化合物 |
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| CN104936450A (zh) * | 2012-12-20 | 2015-09-23 | 巴斯夫欧洲公司 | 包含三唑化合物的组合物 |
| CA2894264C (en) * | 2012-12-20 | 2023-03-07 | BASF Agro B.V. | Compositions comprising a triazole compound |
| WO2014108299A1 (en) * | 2013-01-09 | 2014-07-17 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
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| WO2014124850A1 (en) | 2013-02-14 | 2014-08-21 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014198557A1 (en) * | 2013-06-12 | 2014-12-18 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2813499A1 (en) | 2013-06-12 | 2014-12-17 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014198553A1 (en) * | 2013-06-12 | 2014-12-18 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| BR112016000299B8 (pt) | 2013-07-08 | 2021-04-20 | Basf Agro Bv | composições, uso de uma composição, método para o combate dos fungos fitopatogênicos e uso dos componentes |
| EP2839745A1 (en) | 2013-08-21 | 2015-02-25 | Basf Se | Agrochemical formulations comprising a 2-ethyl-hexanol alkoxylate |
| JP6053948B2 (ja) | 2013-10-24 | 2016-12-27 | 三菱電機株式会社 | 情報処理装置及び情報処理方法及びプログラム |
| UA118214C2 (uk) | 2014-02-14 | 2018-12-10 | Басф Агро Б.В. | Здатний до емульгування концентрат, що включає пестицид, жирний амід і лактамід |
| EP3272217A1 (en) | 2014-06-25 | 2018-01-24 | BASF Agro B.V. | Pesticidal compositions |
| ES2688377T3 (es) | 2014-07-08 | 2018-11-02 | BASF Agro B.V. | Proceso para la preparación de oxiranos y triazoles sustituidos |
| EP3169157B1 (en) | 2014-07-14 | 2021-09-08 | Basf Se | Pesticidal compositions |
| WO2016071167A1 (en) | 2014-11-07 | 2016-05-12 | Basf Se | Pesticidal mixtures |
| EP3028573A1 (en) | 2014-12-05 | 2016-06-08 | Basf Se | Use of a triazole fungicide on transgenic plants |
| WO2016174042A1 (en) | 2015-04-27 | 2016-11-03 | BASF Agro B.V. | Pesticidal compositions |
| WO2016180614A1 (en) | 2015-05-08 | 2016-11-17 | Basf Se | A process for the preparation of limonene-4-ol |
| MX2017014351A (es) | 2015-05-08 | 2018-11-09 | Basf Agro Bv | Un proceso para la preparacion de epoxido de terpinoleno. |
| EP3111763A1 (en) | 2015-07-02 | 2017-01-04 | BASF Agro B.V. | Pesticidal compositions comprising a triazole compound |
| CN107809906A (zh) | 2015-07-02 | 2018-03-16 | 巴斯夫农业公司 | 包含三唑化合物的农药组合物 |
| WO2017157910A1 (en) | 2016-03-16 | 2017-09-21 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals |
| WO2017157916A1 (en) | 2016-03-16 | 2017-09-21 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean |
| CA3015456C (en) | 2016-03-16 | 2024-09-17 | Basf Se | USE OF TETRAZOLINONES TO CONTROL RESISTANT PLANT PATHOGENIC FUNGI ON FRUIT |
| EP3472139B1 (en) | 2016-06-15 | 2021-04-07 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| AU2017286055B2 (en) | 2016-06-15 | 2021-07-01 | BASF Agro B.V. | Process for the epoxidation of a tetrasubstituted alkene |
| WO2018054829A1 (en) | 2016-09-22 | 2018-03-29 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives and their use as fungicides |
| EP3515907A1 (en) | 2016-09-22 | 2019-07-31 | Bayer CropScience Aktiengesellschaft | Novel triazole derivatives |
| CA3052519A1 (en) | 2017-02-08 | 2018-08-16 | Andreas Gortz | Triazolethione derivatives |
| US20200045967A1 (en) | 2017-02-08 | 2020-02-13 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
| BR112019016241A2 (pt) | 2017-02-08 | 2020-04-07 | Bayer Cropscience Ag | derivados de triazol e seu uso como fungicidas |
| KR20190115449A (ko) | 2017-02-10 | 2019-10-11 | 바이엘 악티엔게젤샤프트 | 1-(페녹시-피리디닐)-2-(1,2,4-트리아졸-1-일)-에탄올 유도체를 포함하는 유해 미생물을 방제하기 위한 조성물 |
| EP3421460A1 (en) | 2018-03-15 | 2019-01-02 | Bayer Aktiengesellschaft | 2-[(4-alkylphenoxy)-pyridinyl]-1-(1,2,4-triazol-1-yl)alkan-2-ol fungicides |
| WO2020020813A1 (en) | 2018-07-25 | 2020-01-30 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
| WO2020020816A1 (en) | 2018-07-26 | 2020-01-30 | Bayer Aktiengesellschaft | Novel triazole derivatives |
| WO2020070050A1 (en) | 2018-10-01 | 2020-04-09 | Bayer Aktiengesellschaft | Fungicidal 5-substituted imidazol-1-yl carbinol derivatives |
| EP3620053A1 (en) | 2018-12-14 | 2020-03-11 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2547953A1 (de) * | 1975-10-27 | 1977-04-28 | Bayer Ag | (1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| AU515134B2 (en) * | 1976-08-10 | 1981-03-19 | Janssen Pharmaceutica N.V. | 1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles |
| DE2650831A1 (de) * | 1976-11-06 | 1978-05-11 | Basf Ag | Mittel zur beeinflussung des pflanzenwachstums |
| DE2725214A1 (de) * | 1977-06-03 | 1978-12-14 | Bayer Ag | Metallsalzkomplexe von 1-phenyl-2- triazolyl-aethyl-derivaten, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2725314A1 (de) * | 1977-06-04 | 1978-12-14 | Bayer Ag | 1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| US4654332A (en) * | 1979-03-07 | 1987-03-31 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| CH647513A5 (de) * | 1979-11-13 | 1985-01-31 | Sandoz Ag | Triazol-derivate, deren herstellung und verwendung. |
| AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| EP0131684B1 (en) * | 1980-08-18 | 1992-03-11 | Imperial Chemical Industries Plc | Use of triazolylethanol derivatives and their compositions as non-agricultural fungicides |
| EP0052424B2 (en) * | 1980-11-19 | 1990-02-28 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| DE3140276A1 (de) * | 1981-10-10 | 1983-04-28 | Bayer Ag, 5090 Leverkusen | Phenoxyphenyl-azolylmethyl-ketone und -carbinole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und als zwischenprodukte |
| ATE49200T1 (de) * | 1981-11-27 | 1990-01-15 | Ciba Geigy Ag | Mikrobizide triazolyl-ethyl-aether. |
| DE3202604A1 (de) * | 1982-01-27 | 1983-08-04 | Bayer Ag, 5090 Leverkusen | Ether-derivate von substituierten 1-hydroxyalkyl-azolen, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren |
| US4610716A (en) * | 1982-12-14 | 1986-09-09 | Ciba-Geigy Corporation | Fluorinated azolyl ethanol growth regulators and microbicides |
| GB2143815B (en) * | 1983-05-19 | 1988-01-20 | Ciba Geigy Ag | Process for the preparation of micro biocidal 1-triazolylethyl ether derivatives |
-
1984
- 1984-05-16 GB GB08412506A patent/GB2143815B/en not_active Expired
- 1984-05-16 DE DE8484105582T patent/DE3484968D1/de not_active Expired - Lifetime
- 1984-05-16 AT AT84105582T patent/ATE66676T1/de active
- 1984-05-16 EP EP84105582A patent/EP0126430B1/de not_active Expired - Lifetime
- 1984-05-17 PT PT78602A patent/PT78602A/pt not_active IP Right Cessation
- 1984-05-17 CA CA000454548A patent/CA1223264A/en not_active Expired
- 1984-05-17 DD DD84281418A patent/DD248274A5/de not_active IP Right Cessation
- 1984-05-17 IL IL71862A patent/IL71862A/xx unknown
- 1984-05-17 DK DK248184A patent/DK248184A/da not_active Application Discontinuation
- 1984-05-17 GR GR74745A patent/GR79954B/el unknown
- 1984-05-17 IL IL8483707A patent/IL83707A/xx unknown
- 1984-05-17 DD DD84263132A patent/DD226882A5/de not_active IP Right Cessation
- 1984-05-18 NZ NZ208209A patent/NZ208209A/en unknown
- 1984-05-18 ES ES532604A patent/ES8600635A1/es not_active Expired
- 1984-05-18 CS CS843769A patent/CS247179B2/cs unknown
- 1984-05-18 HU HU841926A patent/HU196693B/hu not_active IP Right Cessation
- 1984-05-18 MX MX576984A patent/MX5769A/es unknown
- 1984-05-18 IE IE1247/84A patent/IE57488B1/en not_active IP Right Cessation
- 1984-05-18 ZA ZA843774A patent/ZA843774B/xx unknown
- 1984-05-18 IE IE2779/88A patent/IE57489B1/en not_active IP Right Cessation
- 1984-05-18 TR TR3611/84A patent/TR22379A/xx unknown
- 1984-05-18 PH PH30696A patent/PH20959A/en unknown
- 1984-05-18 BR BR8402388A patent/BR8402388A/pt not_active IP Right Cessation
- 1984-05-18 NZ NZ219282A patent/NZ219282A/en unknown
- 1984-05-18 AU AU28358/84A patent/AU572145B2/en not_active Ceased
- 1984-05-19 KR KR1019840002741A patent/KR890000533B1/ko not_active Expired
- 1984-05-19 JP JP59101625A patent/JPS59222434A/ja active Granted
-
1985
- 1985-08-08 CS CS855782A patent/CS247200B2/cs unknown
- 1985-10-25 PH PH32973A patent/PH21667A/en unknown
- 1985-10-25 PH PH32974A patent/PH22876A/en unknown
-
1986
- 1986-09-22 GB GB08622763A patent/GB2179659B/en not_active Expired
-
1987
- 1987-08-31 IL IL83707A patent/IL83707A0/xx unknown
- 1987-09-30 MY MYPI87002496A patent/MY102774A/en unknown
-
1988
- 1988-05-02 AU AU15504/88A patent/AU607993B2/en not_active Ceased
- 1988-09-02 US US07/240,441 patent/US4945100A/en not_active Expired - Fee Related
- 1988-11-10 KR KR1019880014855A patent/KR900003367B1/ko not_active Expired
-
1989
- 1989-05-01 JP JP1112794A patent/JPH0285265A/ja active Granted
- 1989-05-01 JP JP1112793A patent/JPH0296544A/ja active Granted
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