JPH0361666B2 - - Google Patents

Info

Publication number: JPH0361666B2
Authority: JP; Japan
Prior art keywords: group; carbon atoms; formula; substituted; alkyl
Prior art date: 1983-05-19
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

Application number

JP59101625A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59222434A (ja

Inventor

Nifueraa Roberuto

Zondoraa Herumuuto

Sutsurumu Erumaa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1983-05-19

Filing date

1984-05-19

Publication date

1991-09-20

1984-05-19 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1984-12-14 Publication of JPS59222434A publication Critical patent/JPS59222434A/ja

1991-09-20 Publication of JPH0361666B2 publication Critical patent/JPH0361666B2/ja

Status Granted legal-status Critical Current

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)
Epoxy Compounds (AREA)
Plural Heterocyclic Compounds (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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

JP59101625A 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 Granted JPS59222434A (ja)

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 (2)	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 (2)
EP (1)	EP0126430B1 (2)
JP (3)	JPS59222434A (2)
KR (2)	KR890000533B1 (2)
AT (1)	ATE66676T1 (2)
AU (2)	AU572145B2 (2)
BR (1)	BR8402388A (2)
CA (1)	CA1223264A (2)
CS (2)	CS247179B2 (2)
DD (2)	DD248274A5 (2)
DE (1)	DE3484968D1 (2)
DK (1)	DK248184A (2)
ES (1)	ES532604A0 (2)
GB (2)	GB2143815B (2)
GR (1)	GR79954B (2)
HU (1)	HU196693B (2)
IE (2)	IE57489B1 (2)
IL (3)	IL83707A (2)
MX (1)	MX5769A (2)
MY (1)	MY102774A (2)
NZ (2)	NZ208209A (2)
PH (3)	PH20959A (2)
PT (1)	PT78602A (2)
TR (1)	TR22379A (2)
ZA (1)	ZA843774B (2)

Families Citing this family (75)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1984
- 1984-05-16 GB GB08412506A patent/GB2143815B/en not_active Expired
- 1984-05-16 EP EP84105582A patent/EP0126430B1/de not_active Expired - Lifetime
- 1984-05-16 DE DE8484105582T patent/DE3484968D1/de not_active Expired - Lifetime
- 1984-05-16 AT AT84105582T patent/ATE66676T1/de active
- 1984-05-17 GR GR74745A patent/GR79954B/el unknown
- 1984-05-17 DD DD84281418A patent/DD248274A5/de not_active IP Right Cessation
- 1984-05-17 IL IL8483707A patent/IL83707A/xx unknown
- 1984-05-17 DK DK248184A patent/DK248184A/da not_active Application Discontinuation
- 1984-05-17 DD DD84263132A patent/DD226882A5/de not_active IP Right Cessation
- 1984-05-17 IL IL71862A patent/IL71862A/xx unknown
- 1984-05-17 PT PT78602A patent/PT78602A/pt not_active IP Right Cessation
- 1984-05-17 CA CA000454548A patent/CA1223264A/en not_active Expired
- 1984-05-18 NZ NZ208209A patent/NZ208209A/en unknown
- 1984-05-18 CS CS843769A patent/CS247179B2/cs unknown
- 1984-05-18 ES ES532604A patent/ES532604A0/es active Granted
- 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 NZ NZ219282A patent/NZ219282A/en unknown
- 1984-05-18 BR BR8402388A patent/BR8402388A/pt not_active IP Right Cessation
- 1984-05-18 TR TR3611/84A patent/TR22379A/xx unknown
- 1984-05-18 IE IE1247/84A patent/IE57488B1/en not_active IP Right Cessation
- 1984-05-18 HU HU841926A patent/HU196693B/hu not_active IP Right Cessation
- 1984-05-18 PH PH30696A patent/PH20959A/en unknown
- 1984-05-18 MX MX576984A patent/MX5769A/es unknown
- 1984-05-18 AU AU28358/84A patent/AU572145B2/en not_active Ceased
- 1984-05-19 JP JP59101625A patent/JPS59222434A/ja active Granted
- 1984-05-19 KR KR1019840002741A patent/KR890000533B1/ko not_active Expired
1985
- 1985-08-08 CS CS855782A patent/CS247200B2/cs unknown
- 1985-10-25 PH PH32974A patent/PH22876A/en unknown
- 1985-10-25 PH PH32973A patent/PH21667A/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

Also Published As

Publication number	Publication date
JPH0420912B2 (2)	1992-04-07
ES8600635A1 (es)	1985-10-16
AU607993B2 (en)	1991-03-21
IE841247L (en)	1984-11-19
MX5769A (es)	1993-10-01
DK248184A (da)	1984-11-20
EP0126430A2 (de)	1984-11-28
GR79954B (2)	1984-10-31
EP0126430A3 (en)	1986-05-14
BR8402388A (pt)	1985-04-02
GB2179659A (en)	1987-03-11
ATE66676T1 (de)	1991-09-15
KR900003367B1 (ko)	1990-05-16
GB8412506D0 (en)	1984-06-20
PH22876A (en)	1989-01-19
IL71862A0 (en)	1984-09-30
KR890000533B1 (ko)	1989-03-20
PH21667A (en)	1988-01-13
KR850000417A (ko)	1985-02-27
IL83707A0 (en)	1988-01-31
MY102774A (en)	1992-10-31
JPH0285265A (ja)	1990-03-26
GB2143815A (en)	1985-02-20
DE3484968D1 (de)	1991-10-02
US4945100A (en)	1990-07-31
IE882779L (en)	1984-11-19
GB2179659B (en)	1988-01-27
NZ219282A (en)	1988-02-12
PT78602A (de)	1984-06-01
EP0126430B1 (de)	1991-08-28
CS247200B2 (cs)	1986-12-18
HUT34011A (en)	1985-01-28
JPH0552819B2 (2)	1993-08-06
CS247179B2 (en)	1986-12-18
IL83707A (en)	1988-08-31
DD248274A5 (de)	1987-08-05
KR900008926A (ko)	1990-06-03
IE57488B1 (en)	1992-10-07
DK248184D0 (da)	1984-05-17
AU572145B2 (en)	1988-05-05
AU2835884A (en)	1984-11-22
AU1550488A (en)	1988-07-21
IE57489B1 (en)	1992-10-07
JPH0296544A (ja)	1990-04-09
PH20959A (en)	1987-06-10
GB8622763D0 (en)	1986-10-29
CA1223264A (en)	1987-06-23
NZ208209A (en)	1988-01-08
IL71862A (en)	1988-08-31
GB2143815B (en)	1988-01-20
TR22379A (tr)	1987-03-11
DD226882A5 (de)	1985-09-04
ZA843774B (en)	1985-01-30
HU196693B (en)	1989-01-30
JPS59222434A (ja)	1984-12-14
ES532604A0 (es)	1985-10-16

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JPH0361666B2 (2)	1991-09-20
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JPH0582387B2 (2)	1993-11-18
EP0273528A1 (en)	1988-07-06	Benzophenones and their preparation
FI101222B (fi)	1998-05-15	Menetelmä terapeuttisesti aktiivisten kinolin-2-yylimetoksifenyylijohd annaisten valmistamiseksi
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JPS5942338A (ja)	1984-03-08	ケトアルデヒド誘導体およびその製造方法
JP2001106687A (ja)	2001-04-17	種々の複素環式環系を有する５−リポキシゲナーゼ阻害剤の製造方法
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