JPH0339060B2 - - Google Patents

Info

Publication number: JPH0339060B2
Authority: JP; Japan
Prior art keywords: group; pyrazoline; general formula; compound; atom
Prior art date: 1982-01-14
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

Application number

JP432682A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58170761A (ja

Inventor

Shimizu Ozawa

Yasuyuki Nakajima

Makoto Tsugeno

Shigeru Ishii

Masataka Hatanaka

Masayoshi Hirose

Masaki Kudo

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.)

Nissan Chemical Corp

Original Assignee

Nissan Chemical Corp

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.)

1982-01-14

Filing date

1982-01-14

Publication date

1991-06-12

1982-01-14 Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp

1982-01-14 Priority to JP432682A priority Critical patent/JPS58170761A/ja

1982-02-05 Priority to GB8203354A priority patent/GB2093836B/en

1982-02-10 Priority to CA000395923A priority patent/CA1171419A/en

1982-02-10 Priority to AU80320/82A priority patent/AU544267B2/en

1982-02-15 Priority to DE8282101106T priority patent/DE3266262D1/de

1982-02-15 Priority to EP82101106A priority patent/EP0058424B1/en

1982-02-17 Priority to EG7882A priority patent/EG16507A/xx

1982-02-17 Priority to BR8200864A priority patent/BR8200864A/pt

1982-02-17 Priority to KR8200680A priority patent/KR870001945B1/ko

1983-01-05 Priority to US06/455,735 priority patent/US4464386A/en

1983-01-27 Priority to US06/461,666 priority patent/US4540706A/en

1983-10-07 Publication of JPS58170761A publication Critical patent/JPS58170761A/ja

1991-06-12 Publication of JPH0339060B2 publication Critical patent/JPH0339060B2/ja

Status Granted legal-status Critical Current

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
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Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

JP432682A 1981-02-17 1982-01-14 新規ピラゾリン誘導体，その製造方法およびそれを有効成分として含有する有害生物防除剤 Granted JPS58170761A (ja)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
JP432682A JPS58170761A (ja)	1982-01-14	1982-01-14	新規ピラゾリン誘導体，その製造方法およびそれを有効成分として含有する有害生物防除剤
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	피라졸린 유도체의 제법
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	新規ピラゾリン誘導体，その製造方法およびそれを有効成分として含有する有害生物防除剤

Publications (2)

Publication Number	Publication Date
JPS58170761A JPS58170761A (ja)	1983-10-07
JPH0339060B2 true JPH0339060B2 (pl)	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	新規ピラゾリン誘導体，その製造方法およびそれを有効成分として含有する有害生物防除剤

Country Status (1)

Country	Link
JP (1)	JPS58170761A (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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

Publication	Publication Date	Title
JPS6217583B2 (pl)	1987-04-18
JPH0547553B2 (pl)	1993-07-19
CS258495B2 (en)	1988-08-16	Insecticide and acaricide and method of efficient substances production
BE1001812A4 (fr)	1990-03-13	Derives du 1,5-diphenyl-1h-1,2,4-triazole-3-carboxamide et compositions herbicides qui les contiennent.
JPH0341039A (ja)	1991-02-21	新規化合物
KR870001945B1 (ko)	1987-10-23	피라졸린 유도체의 제법
JP2704655B2 (ja)	1998-01-26	３一置換フェニルピラゾール誘導体又はその塩類及び除草剤
US4407813A (en)	1983-10-04	Insecticidal pyrazoline derivatives and composition
EP0004754A2 (en)	1979-10-17	Ketoximinoether insecticides
JPH0339060B2 (pl)	1991-06-12
US4464386A (en)	1984-08-07	Insecticidal 3-difluoromethoxyphenyl-1-phenylcarbamoyl-2-pyrazolines
JPS625928A (ja)	1987-01-12	炭化水素系化合物およびそれを有効成分とする殺虫、殺ダニ剤
US4902337A (en)	1990-02-20	Herbicidal hydantoin derivatives
JPH0143748B2 (pl)	1989-09-22
JPH0133102B2 (pl)	1989-07-11
US4540706A (en)	1985-09-10	Insecticidal 1-N-phenylcarbamoyl-3-(4-difluoromethoxyphenyl)-4-phenyl-2-pyrazoline derivatives
JPH01230562A (ja)	1989-09-14	フェニルトリアゾール誘導体及び殺虫剤
CH659249A5 (fr)	1987-01-15	Derives triazolyles et leur utilisation fongicide dans la domaine agricole.
JP2809482B2 (ja)	1998-10-08	２―アルコキシ―１，４―ジヒドロ―４―オキソ―３―ピリジンカルボキサミド誘導体、その製造法および除草剤
JPS59116243A (ja)	1984-07-05	２―アリールエチルエーテル誘導体およびチオエーテル誘導体の製造方法
DE3615448A1 (de)	1987-11-12	Neue e/z-isomere fungizid wirksame acrylsaeureverbindungen, verfahren zu deren herstellung und zwischenprodukte zur durchfuehrung des verfahrens
EP0722939A1 (en)	1996-07-24	4-iminooxazolidin-2-one derivative, process for producing the same, and herbicide containing the same as active ingredient
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