JPH0143748B2 - - Google Patents

Info

Publication number: JPH0143748B2
Authority: JP; Japan
Prior art keywords: compound; present; formula; parts; pyrazoline
Prior art date: 1981-02-17
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

JP2176781A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57136572A (en

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.)

1981-02-17

Filing date

1981-02-17

Publication date

1989-09-22

1981-02-17 Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp

1981-02-17 Priority to JP2176781A priority Critical patent/JPS57136572A/ja

1981-08-13 Priority to US06/292,710 priority patent/US4407813A/en

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

1982-02-09 Priority to ZA82817A priority patent/ZA82817B/xx

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 EP82101106A priority patent/EP0058424B1/en

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

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

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

1982-08-23 Publication of JPS57136572A publication Critical patent/JPS57136572A/ja

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

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

1989-09-22 Publication of JPH0143748B2 publication Critical patent/JPH0143748B2/ja

Status Granted legal-status Critical Current

Links

239000002917 insecticide Substances 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
150000003219 pyrazolines Chemical class 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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 claims description 5
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 43
239000000203 mixture Substances 0.000 description 28
238000012360 testing method Methods 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
229910001868 water Inorganic materials 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
238000009472 formulation Methods 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
230000000749 insecticidal effect Effects 0.000 description 10
-1 pyrazoline compound Chemical class 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000000839 emulsion Substances 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 5
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NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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229920000742 Cotton Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000007605 air drying Methods 0.000 description 3
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OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
231100000111 LD50 Toxicity 0.000 description 2
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
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 1
RPXYFYFWSOUIGD-UHFFFAOYSA-N 1,3-bis(4-hydroxyphenyl)-1,3-diphenylpropan-2-one Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)C(=O)C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RPXYFYFWSOUIGD-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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 1
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 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
ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical group C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
IBHYTRJMMUPWFN-UHFFFAOYSA-N 4-phenyl-4,5-dihydro-1h-pyrazole Chemical compound C1NN=CC1C1=CC=CC=C1 IBHYTRJMMUPWFN-UHFFFAOYSA-N 0.000 description 1
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VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
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WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
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IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
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XBJXEKFQXHPCIC-UHFFFAOYSA-N n-(4-chlorophenyl)-5-[4-(difluoromethoxy)phenyl]-4-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C1=NN(C(=O)NC=2C=CC(Cl)=CC=2)CC1C1=CC=CC=C1 XBJXEKFQXHPCIC-UHFFFAOYSA-N 0.000 description 1
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UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

JP2176781A 1981-02-17 1981-02-17 Novel pyrazoline derivative, its preparation, and noxious life controlling agent containing said derivative as active component Granted JPS57136572A (en)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
JP2176781A JPS57136572A (en)	1981-02-17	1981-02-17	Novel pyrazoline derivative, its preparation, and noxious life controlling agent containing said derivative as active component
US06/292,710 US4407813A (en)	1981-02-17	1981-08-13	Insecticidal pyrazoline derivatives and composition
GB8203354A GB2093836B (en)	1981-02-17	1982-02-05	Insecticidal pyrazoline derivatives
ZA82817A ZA82817B (en)	1981-02-17	1982-02-09	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
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
JP2176781A JPS57136572A (en)	1981-02-17	1981-02-17	Novel pyrazoline derivative, its preparation, and noxious life controlling agent containing said derivative as active component

Publications (2)

Publication Number	Publication Date
JPS57136572A JPS57136572A (en)	1982-08-23
JPH0143748B2 true JPH0143748B2 (pl)	1989-09-22

Family

ID=12064216

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2176781A Granted JPS57136572A (en)	1981-02-17	1981-02-17	Novel pyrazoline derivative, its preparation, and noxious life controlling agent containing said derivative as active component

Country Status (2)

Country	Link
JP (1)	JPS57136572A (pl)
ZA (1)	ZA82817B (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57209275A (en) *	1981-06-19	1982-12-22	Nissan Chem Ind Ltd	Novel pyrazoline derivative, its preparation, and vermin-controlling agent containing said derivative as active component
DE3545786A1 (de) *	1985-12-21	1987-06-25	Schering Ag	Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung

1981
- 1981-02-17 JP JP2176781A patent/JPS57136572A/ja active Granted
1982
- 1982-02-09 ZA ZA82817A patent/ZA82817B/xx unknown

Also Published As

Publication number	Publication date
ZA82817B (en)	1982-12-29
JPS57136572A (en)	1982-08-23

Publication	Publication Date	Title
JP2577189B2 (ja)	1997-01-29	新規ヒドラジン誘導体およびそれを有効成分とする殺虫組成物
JPH0547553B2 (pl)	1993-07-19
JPH1081609A (ja)	1998-03-31	１，３−オキサジン−４−オン誘導体を含有する除草剤
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
GB2093836A (en)	1982-09-08	Insecticidal pyrazoline derivatives
JP3279818B2 (ja)	2002-04-30	殺虫・殺ダニ剤
DE60120402T2 (de)	2006-10-19	2-(3,5-disubstituierte-4-pyridyl)-4-(thienyl, thiazolyl oder arylphenyl)-1,3-oxazolinverbindungen
US4407813A (en)	1983-10-04	Insecticidal pyrazoline derivatives and composition
WO2010075760A1 (zh)	2010-07-08	具有杀虫活性的含氮杂环化合物、其制备及用途
JPH0143748B2 (pl)	1989-09-22
JPH0347275B2 (pl)	1991-07-18
JPH0133102B2 (pl)	1989-07-11
JPH0625095A (ja)	1994-02-01	７−エチニル−α−（メトキシメチレン）−１−ナフタリン酢酸の新規な誘導体、それらの製造法及び有害生物駆除剤としての使用
JPH0539252A (ja)	1993-02-19	Ｎ，Ｎ’−ジベンゾイル−ｔｅｒｔ−ブチルヒドラジン誘導体およびそれを有効成分とする殺虫組成物
JPH02229157A (ja)	1990-09-11	テトラヒドロフタルイミド誘導体および除草剤
JPH0339060B2 (pl)	1991-06-12
US4540706A (en)	1985-09-10	Insecticidal 1-N-phenylcarbamoyl-3-(4-difluoromethoxyphenyl)-4-phenyl-2-pyrazoline derivatives
US4863504A (en)	1989-09-05	Cyclohexadione derivatives, selective herbicidal compositions as well as herbicidal method
RU2038352C1 (ru)	1995-06-27	Производные амина или их соли и инсектицидная композиция на их основе
JPH08231528A (ja)	1996-09-10	新規ヒドラジン誘導体およびそれを有効成分とする殺虫組成物
JPH08231529A (ja)	1996-09-10	ヒドラジン誘導体およびそれを有効成分とする殺虫組成物
JPH06172342A (ja)	1994-06-21	新規ヒドラジン誘導体およびそれを有効成分とする殺虫組成物
EP0129889A2 (en)	1985-01-02	An oxime derivative and its use as an insecticide or acaricide
JP3102502B2 (ja)	2000-10-23	アミジン誘導体及びそれを含有する殺虫、殺ダニ組成物
CN119751423A (zh)	2025-04-04	一种含嘧啶的芳基吡唑肟醚类化合物及其制备方法和应用