JPH0339060B2 - - Google Patents
Info
- Publication number
- JPH0339060B2 JPH0339060B2 JP432682A JP432682A JPH0339060B2 JP H0339060 B2 JPH0339060 B2 JP H0339060B2 JP 432682 A JP432682 A JP 432682A JP 432682 A JP432682 A JP 432682A JP H0339060 B2 JPH0339060 B2 JP H0339060B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrazoline
- general formula
- compound
- atom
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 73
- 238000004519 manufacturing process Methods 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 241000607479 Yersinia pestis Species 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000003219 pyrazolines Chemical class 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 44
- 239000000203 mixture Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 229910001868 water Inorganic materials 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000002994 raw material Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- -1 pyrazoline compound Chemical class 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 239000002917 insecticide Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000004847 absorption spectroscopy Methods 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 8
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical class C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 230000000749 insecticidal effect Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- FHQHGONWDDDNCE-UHFFFAOYSA-N 3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-1h-pyrazole Chemical class C1=CC(OC(F)F)=CC=C1C1=NNCC1 FHQHGONWDDDNCE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 231100000614 poison Toxicity 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- JBQTZLNCDIFCCO-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-phenylethan-1-one Chemical compound C1=CC(O)=CC=C1C(=O)CC1=CC=CC=C1 JBQTZLNCDIFCCO-UHFFFAOYSA-N 0.000 description 3
- HWHSXOWFPIHTGE-UHFFFAOYSA-N 3-[4-(difluoromethoxy)phenyl]-4-methyl-4,5-dihydro-1h-pyrazole Chemical compound CC1CNN=C1C1=CC=C(OC(F)F)C=C1 HWHSXOWFPIHTGE-UHFFFAOYSA-N 0.000 description 3
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 241001556089 Nilaparvata lugens Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- OJPBXGHGERDPQV-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-2-phenylethanone Chemical compound C1=CC(OC(F)F)=CC=C1C(=O)CC1=CC=CC=C1 OJPBXGHGERDPQV-UHFFFAOYSA-N 0.000 description 2
- BVRHCNRPPZCQIS-UHFFFAOYSA-N 1-[bromo(difluoro)methyl]sulfanyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(SC(F)(F)Br)C=C1 BVRHCNRPPZCQIS-UHFFFAOYSA-N 0.000 description 2
- NYQSIHZNEJCZKX-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethylsulfanyl)benzene Chemical compound FC(F)(F)SC1=CC=C(N=C=O)C=C1 NYQSIHZNEJCZKX-UHFFFAOYSA-N 0.000 description 2
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical class C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 2
- UNWXTIMZARMQEH-UHFFFAOYSA-N 3-[4-(difluoromethoxy)phenyl]-4-phenyl-4,5-dihydro-1h-pyrazole Chemical compound C1=CC(OC(F)F)=CC=C1C1=NNCC1C1=CC=CC=C1 UNWXTIMZARMQEH-UHFFFAOYSA-N 0.000 description 2
- SMOAXJZTOPUFGP-UHFFFAOYSA-N 3-[4-(difluoromethoxy)phenyl]-5,5-dimethyl-4-phenyl-n-[4-(trifluoromethylsulfanyl)phenyl]-4h-pyrazole-1-carboxamide Chemical compound CC1(C)C(C=2C=CC=CC=2)C(C=2C=CC(OC(F)F)=CC=2)=NN1C(=O)NC1=CC=C(SC(F)(F)F)C=C1 SMOAXJZTOPUFGP-UHFFFAOYSA-N 0.000 description 2
- HDOFWFJSKJNFST-UHFFFAOYSA-N 4-[3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-1h-pyrazol-4-yl]butanenitrile Chemical compound C1=CC(OC(F)F)=CC=C1C1=NNCC1CCCC#N HDOFWFJSKJNFST-UHFFFAOYSA-N 0.000 description 2
- AMHPHEOPYNPEIX-UHFFFAOYSA-N 4-[bromo(difluoro)methoxy]aniline Chemical compound NC1=CC=C(OC(F)(F)Br)C=C1 AMHPHEOPYNPEIX-UHFFFAOYSA-N 0.000 description 2
- JHKOEEAMBXPXTK-UHFFFAOYSA-N 4-bromo-2-(difluoromethoxy)-1-isocyanatobenzene Chemical compound FC(F)OC1=CC(Br)=CC=C1N=C=O JHKOEEAMBXPXTK-UHFFFAOYSA-N 0.000 description 2
- IBHYTRJMMUPWFN-UHFFFAOYSA-N 4-phenyl-4,5-dihydro-1h-pyrazole Chemical compound C1NN=CC1C1=CC=CC=C1 IBHYTRJMMUPWFN-UHFFFAOYSA-N 0.000 description 2
- DAXIIVIGOFVCRK-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-4-propan-2-yl-n-[4-(trifluoromethoxy)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound CC(C)C1CN(C(=O)NC=2C=CC(OC(F)(F)F)=CC=2)N=C1C1=CC=C(OC(F)F)C=C1 DAXIIVIGOFVCRK-UHFFFAOYSA-N 0.000 description 2
- WHQOGZZJHFXZNH-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-n-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C1=NN(C(=O)NC=2C=CC(OC(F)(F)C(F)F)=CC=2)CC1 WHQOGZZJHFXZNH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
- 241001600408 Aphis gossypii Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241001498622 Cixius wagneri Species 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 241001635274 Cydia pomonella Species 0.000 description 2
- 241000336797 Eoeurysa flavocapitata Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000409991 Mythimna separata Species 0.000 description 2
- 241001477931 Mythimna unipuncta Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000276569 Oryzias latipes Species 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000184734 Pyrus japonica Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000012267 brine Substances 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
- 239000004927 clay Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 102200082872 rs34866629 Human genes 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HGHDFZQBZPKBLJ-UHFFFAOYSA-N 1,3-bis[4-(trifluoromethylsulfanyl)phenyl]urea Chemical compound C1=CC(SC(F)(F)F)=CC=C1NC(=O)NC1=CC=C(SC(F)(F)F)C=C1 HGHDFZQBZPKBLJ-UHFFFAOYSA-N 0.000 description 1
- BKNKXUVEYRKURO-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-2-[(dimethylamino)methyl]-3-methylbutan-1-one;hydrochloride Chemical compound Cl.CN(C)CC(C(C)C)C(=O)C1=CC=C(OC(F)F)C=C1 BKNKXUVEYRKURO-UHFFFAOYSA-N 0.000 description 1
- PWNKYXSPGKGMJB-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-2-phenylprop-2-en-1-one Chemical compound C1=CC(OC(F)F)=CC=C1C(=O)C(=C)C1=CC=CC=C1 PWNKYXSPGKGMJB-UHFFFAOYSA-N 0.000 description 1
- SERLUJOYXDUMBU-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-3-(dimethylamino)-2-methylpropan-1-one;hydrochloride Chemical compound Cl.CN(C)CC(C)C(=O)C1=CC=C(OC(F)F)C=C1 SERLUJOYXDUMBU-UHFFFAOYSA-N 0.000 description 1
- UXLWIGWLZVCQBE-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-3-(dimethylamino)propan-1-one;hydrochloride Chemical compound Cl.CN(C)CCC(=O)C1=CC=C(OC(F)F)C=C1 UXLWIGWLZVCQBE-UHFFFAOYSA-N 0.000 description 1
- IHLUVYPOTPHPOF-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-3-methyl-2-phenylbutan-1-one Chemical compound C=1C=CC=CC=1C(C(C)C)C(=O)C1=CC=C(OC(F)F)C=C1 IHLUVYPOTPHPOF-UHFFFAOYSA-N 0.000 description 1
- JPNHCEIQOASHOX-UHFFFAOYSA-N 1-[bromo(difluoro)methoxy]-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OC(F)(F)Br)C=C1 JPNHCEIQOASHOX-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- STMXDGLZXDOVJG-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-hydroxyphenyl)ethanone Chemical compound C1=CC(O)=CC=C1C(=O)CC1=CC=C(Cl)C=C1 STMXDGLZXDOVJG-UHFFFAOYSA-N 0.000 description 1
- JCQZORFCYBCJBJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[4-(difluoromethoxy)phenyl]prop-2-en-1-one Chemical compound C1=CC(OC(F)F)=CC=C1C(=O)C(=C)C1=CC=C(Cl)C=C1 JCQZORFCYBCJBJ-UHFFFAOYSA-N 0.000 description 1
- HGIDMJOUQKOWMX-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-phenylethanone Chemical compound C1=CC(Cl)=CC=C1CC(=O)C1=CC=CC=C1 HGIDMJOUQKOWMX-UHFFFAOYSA-N 0.000 description 1
- XKWSIMMVZLLASC-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(4-hydroxyphenyl)ethanone Chemical compound C1=CC(O)=CC=C1C(=O)CC1=CC=C(F)C=C1 XKWSIMMVZLLASC-UHFFFAOYSA-N 0.000 description 1
- CWYRBOMWOQXYFZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-phenylethanone Chemical compound C1=CC(F)=CC=C1CC(=O)C1=CC=CC=C1 CWYRBOMWOQXYFZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QQLKGCQKXTVFOC-UHFFFAOYSA-N 2-isocyanato-3-methylthiophene Chemical compound CC=1C=CSC=1N=C=O QQLKGCQKXTVFOC-UHFFFAOYSA-N 0.000 description 1
- JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-UHFFFAOYSA-N 0.000 description 1
- FGCBXTLVUQGHQP-UHFFFAOYSA-N 3,4-dihydropyrazole-2-carboxamide Chemical class NC(=O)N1CCC=N1 FGCBXTLVUQGHQP-UHFFFAOYSA-N 0.000 description 1
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Description
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Claims (1)
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Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP432682A JPS58170761A (ja) | 1982-01-14 | 1982-01-14 | æ°èŠãã©ãŸãªã³èªå°äœïŒãã®è£œé æ¹æ³ããã³ãããæå¹æåãšããŠå«æããæ害çç©é²é€å€ |
| GB8203354A GB2093836B (en) | 1981-02-17 | 1982-02-05 | Insecticidal pyrazoline derivatives |
| CA000395923A CA1171419A (en) | 1981-02-17 | 1982-02-10 | Pyrazoline derivatives |
| AU80320/82A AU544267B2 (en) | 1981-02-17 | 1982-02-10 | Pyrazoline derivatives |
| DE8282101106T DE3266262D1 (de) | 1981-02-17 | 1982-02-15 | Pyrazoline derivatives |
| EP82101106A EP0058424B1 (en) | 1981-02-17 | 1982-02-15 | Pyrazoline derivatives |
| EG7882A EG16507A (en) | 1981-06-19 | 1982-02-17 | Novel pyrazoline derivatives,preparation thereof and pesticides containing itas active ingredsent |
| BR8200864A BR8200864A (pt) | 1981-02-17 | 1982-02-17 | Compostos derivados de pirozolina processo para sua producao e inceticida |
| KR8200680A KR870001945B1 (ko) | 1981-02-17 | 1982-02-17 | íŒëŒì¡žëŠ° ì ë첎ì ì ë² |
| US06/455,735 US4464386A (en) | 1981-02-17 | 1983-01-05 | Insecticidal 3-difluoromethoxyphenyl-1-phenylcarbamoyl-2-pyrazolines |
| US06/461,666 US4540706A (en) | 1981-02-17 | 1983-01-27 | Insecticidal 1-N-phenylcarbamoyl-3-(4-difluoromethoxyphenyl)-4-phenyl-2-pyrazoline derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP432682A JPS58170761A (ja) | 1982-01-14 | 1982-01-14 | æ°èŠãã©ãŸãªã³èªå°äœïŒãã®è£œé æ¹æ³ããã³ãããæå¹æåãšããŠå«æããæ害çç©é²é€å€ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58170761A JPS58170761A (ja) | 1983-10-07 |
| JPH0339060B2 true JPH0339060B2 (ja) | 1991-06-12 |
Family
ID=11581322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP432682A Granted JPS58170761A (ja) | 1981-02-17 | 1982-01-14 | æ°èŠãã©ãŸãªã³èªå°äœïŒãã®è£œé æ¹æ³ããã³ãããæå¹æåãšããŠå«æããæ害çç©é²é€å€ |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58170761A (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3545786A1 (de) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung |
-
1982
- 1982-01-14 JP JP432682A patent/JPS58170761A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58170761A (ja) | 1983-10-07 |
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