RU2003127120A - Пирролкарбоксамиды для применения в качестве фунгицидов - Google Patents
Пирролкарбоксамиды для применения в качестве фунгицидов Download PDFInfo
- Publication number
- RU2003127120A RU2003127120A RU2003127120/04A RU2003127120A RU2003127120A RU 2003127120 A RU2003127120 A RU 2003127120A RU 2003127120/04 A RU2003127120/04 A RU 2003127120/04A RU 2003127120 A RU2003127120 A RU 2003127120A RU 2003127120 A RU2003127120 A RU 2003127120A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- alkyl
- means hydrogen
- fluorine
- Prior art date
Links
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 title claims 2
- 239000000417 fungicide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- SWIGLLMSRXLGCV-UHFFFAOYSA-N 1-methyl-4-(trifluoromethyl)pyrrole-3-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(C(F)(F)F)=C1 SWIGLLMSRXLGCV-UHFFFAOYSA-N 0.000 claims 1
- -1 1-methyl-4-difluoromethyl-1H-pyrrole-3-carboxylic acid amide Chemical compound 0.000 claims 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 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (11)
1. Пирролкарбоксамид формулы I
где R1 означает CF3, CF2H или CFH2;
R2 означает водород или фтор;
R3 означает водород или фтор и
R4 означает водород, фтор, хлор, бром, метил, CF3, OCF3 или SCF3.
2. Соединение формулы I по п.1, где R4 означает водород, хлор, метил, CF3 или OCF3.
3. Соединение формулы I по п.2, где R2 означает водород.
4. Соединение формулы I по п.2, где R2 означает фтор.
5. Соединение формулы I по п.1, выбранное из группы, включающей (4’-бромдифенил-2-ил)амид 1-метил-4-трифторметил-1Н-пиррол-3-карбоновой кислоты и (4’-бромдифенил-2-ил)амид 1-метил-4-дифторметил-1Н-пиррол-3-карбоновой кислоты.
6. Способ получения соединений формулы I, который включает взаимодействие исходных соединений согласно схеме
где R1, R2, R3 и R4 являются такими, как определено для формулы I в п.1.
7. Композиция для борьбы с микроорганизмами и предотвращения поражения и заражения ими растений, в качестве активного ингредиента, включающая соединение по п.1 вместе с подходящим носителем.
8. Способ подавления или предотвращения заражения культивируемых растений фитопатогенными микроорганизмами путем применения соединения формулы I по п.1 к растениям, их частям или месту их произрастания.
9. Соединение общей формулы
где R* означает водород, C1-C6 алкил или Si(C1-C6 алкил)3.
10. Соединение формулы
11. Способ получения соединения формулы
который включает восстановление соединения формулы
где R* означает C1-C6 алкил или Si(C1-C6 алкил)3, в двухстадийном процессе, включающем на первой стадии взаимодействие его с галогенирующим агентом, выбранным из SOCl2/диметилформамида и хлорангидрида щавелевой кислоты/диметилформамида, и на второй стадии восстановление промежуточного хлорангидрида кислоты палладием на углероде в присутствии основания и гидролиз полученного сложного эфира формулы
где R* означает C1-C6 алкил или Si(C1-C6 алкил)3, в щелочных условиях.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0103258.0 | 2001-02-09 | ||
| GBGB0103258.0A GB0103258D0 (en) | 2001-02-09 | 2001-02-09 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2003127120A true RU2003127120A (ru) | 2005-03-10 |
Family
ID=9908443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003127120/04A RU2003127120A (ru) | 2001-02-09 | 2002-02-08 | Пирролкарбоксамиды для применения в качестве фунгицидов |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US20040082477A1 (ru) |
| EP (1) | EP1360176B1 (ru) |
| JP (1) | JP2004528297A (ru) |
| KR (1) | KR20030074794A (ru) |
| CN (1) | CN1223584C (ru) |
| AR (1) | AR035428A1 (ru) |
| AT (1) | ATE344239T1 (ru) |
| BR (1) | BR0207128A (ru) |
| CA (1) | CA2436271A1 (ru) |
| CZ (1) | CZ20032130A3 (ru) |
| DE (1) | DE60215774T2 (ru) |
| EC (1) | ECSP034717A (ru) |
| EG (1) | EG23036A (ru) |
| ES (1) | ES2272697T3 (ru) |
| GB (1) | GB0103258D0 (ru) |
| GT (1) | GT200200008A (ru) |
| HU (1) | HUP0302608A3 (ru) |
| IL (1) | IL157151A0 (ru) |
| MX (1) | MXPA03007016A (ru) |
| PL (1) | PL363372A1 (ru) |
| RU (1) | RU2003127120A (ru) |
| WO (1) | WO2002064562A1 (ru) |
| ZA (1) | ZA200305934B (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9930750D0 (en) * | 1999-12-29 | 2000-02-16 | Novartis Ag | Organic compounds |
| JP2007502312A (ja) * | 2003-05-21 | 2007-02-08 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ジフロオロメチルベンズアニリド類 |
| DE102004041531A1 (de) | 2004-08-27 | 2006-03-02 | Bayer Cropscience Ag | Verfahren zum Herstellen von Biphenylaminen |
| DE102007016971A1 (de) | 2007-04-10 | 2008-10-16 | Saltigo Gmbh | 2-Nitro-5-fluor-3',4'-dichlorbiphenyl sowie ein Verfahren zu dessen Herstellung |
| EP2093216A1 (en) * | 2008-02-25 | 2009-08-26 | Bayer CropScience AG | Process for preparing substituted biphenylanilides |
| CN102786458B (zh) * | 2012-06-04 | 2014-02-12 | 天津渤海职业技术学院 | 吡咯甲酰胺衍生物、其制备方法和用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3689506D1 (de) * | 1985-10-09 | 1994-02-17 | Shell Int Research | Neue Acrylsäureamide. |
| DE19531813A1 (de) * | 1995-08-30 | 1997-03-06 | Basf Ag | Bisphenylamide |
| GB9817548D0 (en) * | 1998-08-12 | 1998-10-07 | Novartis Ag | Organic compounds |
-
2001
- 2001-02-09 GB GBGB0103258.0A patent/GB0103258D0/en not_active Ceased
-
2002
- 2002-01-23 GT GT200200008A patent/GT200200008A/es unknown
- 2002-02-05 EG EG20020149A patent/EG23036A/xx active
- 2002-02-07 AR ARP020100399A patent/AR035428A1/es not_active Application Discontinuation
- 2002-02-08 US US10/467,643 patent/US20040082477A1/en not_active Abandoned
- 2002-02-08 PL PL02363372A patent/PL363372A1/xx not_active Application Discontinuation
- 2002-02-08 EP EP02719787A patent/EP1360176B1/en not_active Expired - Lifetime
- 2002-02-08 CZ CZ20032130A patent/CZ20032130A3/cs unknown
- 2002-02-08 AT AT02719787T patent/ATE344239T1/de not_active IP Right Cessation
- 2002-02-08 ES ES02719787T patent/ES2272697T3/es not_active Expired - Lifetime
- 2002-02-08 IL IL15715102A patent/IL157151A0/xx unknown
- 2002-02-08 CN CNB028047559A patent/CN1223584C/zh not_active Expired - Fee Related
- 2002-02-08 MX MXPA03007016A patent/MXPA03007016A/es unknown
- 2002-02-08 BR BR0207128-2A patent/BR0207128A/pt not_active IP Right Cessation
- 2002-02-08 JP JP2002564495A patent/JP2004528297A/ja active Pending
- 2002-02-08 HU HU0302608A patent/HUP0302608A3/hu unknown
- 2002-02-08 DE DE60215774T patent/DE60215774T2/de not_active Expired - Fee Related
- 2002-02-08 WO PCT/EP2002/001344 patent/WO2002064562A1/en not_active Ceased
- 2002-02-08 KR KR10-2003-7010365A patent/KR20030074794A/ko not_active Withdrawn
- 2002-02-08 CA CA002436271A patent/CA2436271A1/en not_active Abandoned
- 2002-02-08 RU RU2003127120/04A patent/RU2003127120A/ru not_active Application Discontinuation
-
2003
- 2003-07-31 ZA ZA200305934A patent/ZA200305934B/en unknown
- 2003-08-07 EC EC2003004717A patent/ECSP034717A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA03007016A (es) | 2004-05-24 |
| US20040082477A1 (en) | 2004-04-29 |
| GT200200008A (es) | 2002-09-17 |
| DE60215774D1 (de) | 2006-12-14 |
| ZA200305934B (en) | 2004-08-30 |
| CN1491212A (zh) | 2004-04-21 |
| AR035428A1 (es) | 2004-05-26 |
| KR20030074794A (ko) | 2003-09-19 |
| PL363372A1 (en) | 2004-11-15 |
| JP2004528297A (ja) | 2004-09-16 |
| IL157151A0 (en) | 2004-02-08 |
| HUP0302608A3 (en) | 2005-11-28 |
| HUP0302608A2 (hu) | 2003-11-28 |
| BR0207128A (pt) | 2004-03-30 |
| CN1223584C (zh) | 2005-10-19 |
| GB0103258D0 (en) | 2001-03-28 |
| ATE344239T1 (de) | 2006-11-15 |
| EP1360176B1 (en) | 2006-11-02 |
| ES2272697T3 (es) | 2007-05-01 |
| CZ20032130A3 (cs) | 2003-11-12 |
| EP1360176A1 (en) | 2003-11-12 |
| DE60215774T2 (de) | 2007-08-30 |
| ECSP034717A (es) | 2003-09-24 |
| EG23036A (en) | 2004-01-31 |
| WO2002064562A1 (en) | 2002-08-22 |
| CA2436271A1 (en) | 2002-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20060419 |