CN1204123C - N－苯基吡唑衍生物杀虫剂 - Google Patents
N－苯基吡唑衍生物杀虫剂 Download PDFInfo
- Publication number
- CN1204123C CN1204123C CNB021283125A CN02128312A CN1204123C CN 1204123 C CN1204123 C CN 1204123C CN B021283125 A CNB021283125 A CN B021283125A CN 02128312 A CN02128312 A CN 02128312A CN 1204123 C CN1204123 C CN 1204123C
- Authority
- CN
- China
- Prior art keywords
- insecticide
- compound
- pyrazole derivative
- phenyl pyrazole
- regent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000000575 pesticide Substances 0.000 title claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 239000002917 insecticide Substances 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- 230000000857 drug effect Effects 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract description 2
- 241000607479 Yersinia pestis Species 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 1
- 230000035945 sensitivity Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000003217 pyrazoles Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- -1 chloro acetylamino Chemical group 0.000 description 4
- 238000003810 ethyl acetate extraction Methods 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000009885 systemic effect Effects 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
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 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 1
- 241001179564 Melanaphis sacchari Species 0.000 description 1
- 241000409991 Mythimna separata Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical group CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003987 organophosphate pesticide Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- GWBNYWVYPASUBM-UHFFFAOYSA-N trifluoromethanesulfinyl chloride Chemical compound FC(F)(F)S(Cl)=O GWBNYWVYPASUBM-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (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)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021283125A CN1204123C (zh) | 2002-07-30 | 2002-07-30 | N－苯基吡唑衍生物杀虫剂 |
| JP2004523726A JP2005534683A (fr) | 2002-07-30 | 2003-05-12 | Composes insecticides constitues de derives de n-phenylpyrazole |
| AU2003242089A AU2003242089A1 (en) | 2002-07-30 | 2003-05-12 | A series of n-phenylpyrazole derivatives insecticide compounds |
| KR1020047021516A KR100603690B1 (ko) | 2002-07-30 | 2003-05-12 | Ｎ-페닐피라졸 유도체 살충제 화합물 |
| PCT/CN2003/000343 WO2004010785A1 (fr) | 2002-07-30 | 2003-05-12 | Composes insecticides constitues de derives de n-phenylpyrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021283125A CN1204123C (zh) | 2002-07-30 | 2002-07-30 | N－苯基吡唑衍生物杀虫剂 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1398515A CN1398515A (zh) | 2003-02-26 |
| CN1204123C true CN1204123C (zh) | 2005-06-01 |
Family
ID=4745954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021283125A Expired - Lifetime CN1204123C (zh) | 2002-07-30 | 2002-07-30 | N－苯基吡唑衍生物杀虫剂 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2005534683A (fr) |
| KR (1) | KR100603690B1 (fr) |
| CN (1) | CN1204123C (fr) |
| AU (1) | AU2003242089A1 (fr) |
| WO (1) | WO2004010785A1 (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1915977B (zh) * | 2005-08-18 | 2010-04-07 | 李坚 | 氯氟虫腈及其制备和用途 |
| CN100593540C (zh) * | 2007-09-30 | 2010-03-10 | 浙江工业大学 | 一种5-氨基-1-(2,6-二氯-4-三氟甲基苯基)-3-氰基吡唑的制备方法 |
| CN101444221B (zh) * | 2008-12-27 | 2011-11-30 | 东莞市瑞德丰生物科技有限公司 | 一种含有噁二嗪和吡唑类杀虫剂的组合物 |
| CN101491251B (zh) * | 2009-02-23 | 2012-08-08 | 深圳诺普信农化股份有限公司 | 一种农药组合物及其应用 |
| CN102206184B (zh) * | 2010-03-29 | 2013-07-10 | 南开大学 | 3-氰基-1-(2，6-二氯-4-三氟甲基苯基)吡唑衍生物杀虫剂 |
| CN101836649B (zh) * | 2010-05-07 | 2013-05-15 | 湖南化工研究院 | N-苯基-5-取代氨基吡唑类化合物的制剂及应用 |
| CN102250008A (zh) * | 2010-05-17 | 2011-11-23 | 温州大学 | 5-氨基-3-氰基-4-乙硫基-1-(2,6-二氯-4-三氟甲基苯基)吡唑的制备方法 |
| CN104522036B (zh) * | 2014-12-19 | 2017-02-01 | 湖南化工研究院有限公司 | 一种防治鳞翅目和同翅目害虫杀虫组合物 |
| CN104642401B (zh) * | 2015-02-03 | 2018-01-12 | 沈阳农业大学 | 一种防治蝗虫的丁虫腈油剂及其制备方法 |
| CN104855399B (zh) * | 2015-05-02 | 2018-06-19 | 广东中迅农科股份有限公司 | 一种含有丁烯氟虫腈和氟苯虫酰胺的杀虫组合物 |
| CN106305758A (zh) * | 2015-06-23 | 2017-01-11 | 沈阳中化农药化工研发有限公司 | 一种增效复配杀虫、杀螨组合物 |
| CN106187896B (zh) * | 2016-07-19 | 2018-07-31 | 中南民族大学 | 超声波喷雾微波辐射一体化制备芳基吡唑单或多烷基化衍生物 |
| CN111072568A (zh) * | 2019-12-26 | 2020-04-28 | 华东理工大学 | 含偶氮结构的苯基吡唑类化合物及其制备方法和应用 |
| CN114105877A (zh) * | 2021-06-30 | 2022-03-01 | 浙江美诺华药物化学有限公司 | 一种氟虫腈中间体的制备方法及其制备氟虫腈的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| FR2696906B1 (fr) * | 1992-10-20 | 1996-09-20 | Rhone Poulenc Agrochimie | Procede de traitement agrochimique du riz et semences ainsi traitees. |
| US5614182A (en) * | 1995-04-10 | 1997-03-25 | Rhone-Poulenc Inc. | Methods of attracting and combatting insects |
| FR2735952B1 (fr) * | 1995-06-29 | 1997-08-01 | Rhone Poulenc Agrochimie | Procede de controle d'une population d'insectes sociaux |
| FR2739255B1 (fr) * | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
| SE517612C2 (sv) * | 1995-12-20 | 2002-06-25 | Rhone Poulenc Agrochimie | Användning av 5-amino-4-etylsulfinyl-1-arylpyrazol föreningar som pesticider |
| FR2750861B1 (fr) * | 1996-07-11 | 1998-12-24 | Rhone Merieux | Procedes d'elimination des parasites, et notamment des ectoparasites de vertebres, notamment de mammiferes et compositions pour la mise en oeuvre de ce procede |
| EP0839809A1 (fr) * | 1996-11-01 | 1998-05-06 | Rhone-Poulenc Agrochimie | Dérivés pesticides 1-arylpyrazole-5-sulfinilimine |
| FR2761232B1 (fr) * | 1997-03-26 | 2000-03-10 | Rhone Merieux | Procede et moyens d'eradication des puces dans les locaux habites par les petits mammiferes |
| JP4336906B2 (ja) * | 1997-04-07 | 2009-09-30 | 日本農薬株式会社 | ピラゾール誘導体、その製造法、中間体及びこれを有効成分とする有害生物防除剤 |
| ES2327189T3 (es) * | 1997-04-07 | 2009-10-26 | Nihon Nohyaku Co., Ltd. | Derivados de pirazol, su procedimiento de preparacion, intermediarios y plangicida que los contienen como ingrediente activo. |
-
2002
- 2002-07-30 CN CNB021283125A patent/CN1204123C/zh not_active Expired - Lifetime
-
2003
- 2003-05-12 AU AU2003242089A patent/AU2003242089A1/en not_active Abandoned
- 2003-05-12 KR KR1020047021516A patent/KR100603690B1/ko not_active IP Right Cessation
- 2003-05-12 WO PCT/CN2003/000343 patent/WO2004010785A1/fr active Application Filing
- 2003-05-12 JP JP2004523726A patent/JP2005534683A/fr active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1398515A (zh) | 2003-02-26 |
| AU2003242089A1 (en) | 2004-02-16 |
| KR100603690B1 (ko) | 2006-07-20 |
| WO2004010785A1 (fr) | 2004-02-05 |
| KR20050016663A (ko) | 2005-02-21 |
| JP2005534683A (fr) | 2005-11-17 |
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