GB1215066A - Acrylamides and their use as fungicides - Google Patents
Acrylamides and their use as fungicidesInfo
- Publication number
- GB1215066A GB1215066A GB1419868A GB1419868A GB1215066A GB 1215066 A GB1215066 A GB 1215066A GB 1419868 A GB1419868 A GB 1419868A GB 1419868 A GB1419868 A GB 1419868A GB 1215066 A GB1215066 A GB 1215066A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- group
- carbocyclic
- carboxanilide
- dihydro
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,215,066. Acrylamides. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 14 Feb., 1969 [25 March, 1968], No. 14198/68. Heading C2C. [Also in Division A5] Novel acrylamides of the general formula wherein R is an alkyl group; R 1 is H or an alkyl group; R 2 is an unsubstituted carbocyclic group or carbocyclic-amino radical or, when R 1 is H, R 2 may also be a substituted carbocyclic group; A is an optionally substituted carbocyclic or heterocyclic group; B is H or alkyl or A and B, together with the vinylene group to which they are attached, form a carbocyclic group, an optionally substituted furan ring in which the O-atom is adjacent to the C-atom bearing the group R or an optionally substituted benzofuran, oxazole, thiadiazole, triazole, pyran, thiapyran, or pyridine ring system or partially hydrogenated derivatives of these ring systems, with the proviso that when A is CH 3 , R 1 is H and B is alkyl, are prepared by the halogenation of the compound followed by reaction of the acyl halide produced with an amine R 1 R 2 NH. The reaction is preferably performed in benzene or chloroform using thionyl chloride as halogenating agent. Alternative methods for producing the novel compounds are (1) reacting an ester of the acid of Formula II with a metallo-derivative of an amine R 1 R 2 NH, e.g. a Mg Grignard reagent, and (2) reacting a carboxylic acid of Formula II with phenyl phosphazoanilide (giving R 2 = phenyl). Amongst numerous examples are the compounds 2,3 - dimethyl crotonanilide, 2- methyl - furan - 3 - carboxanilide, 3 - trifluoromethyl crotonanilide, 5 - methyl - 1,2,3 - hiadiazole - 4 - carboxanilide, 2 - methyl - 5,6 - dihydro - (4H) - 3 - (N - (4,5 - methylenedioxyphenyl) - carboxamide) and 2 - methyl - 5,6 - dihydro - (4H) - 3 - (N - phenylcarboxhydrazide). 2 - Methyl - 4,5 - dihydrofuran - 3 - carboxylic acid chloride is obtained by treating the corresponding acid with thionyl chloride. 2 - Methyl - 5,6 - dihydro - (4H) - thiapyran- 3-carboxanilide is obtained by reacting thionyl chloride and aniline with the corresponding acid.
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1419868A GB1215066A (en) | 1968-03-25 | 1968-03-25 | Acrylamides and their use as fungicides |
BE730347D BE730347A (en) | 1968-03-25 | 1969-03-24 | |
NL6904465A NL169183C (en) | 1968-03-25 | 1969-03-24 | PROCESS FOR PREPARING FUNGICIDE PREPARATIONS AND PROCESS FOR PREPARING ACRYLAMIDE DERIVATIVES SUITABLE FOR THIS |
DK160369A DK125505B (en) | 1968-03-25 | 1969-03-24 | Fungicide with plant systemic effect. |
FR6908564A FR2004656A1 (en) | 1968-03-25 | 1969-03-24 | |
SE6904059A SE385262B (en) | 1968-03-25 | 1969-03-24 | USE AS GROWTH SYSTEMIC FUNGICIDES OF CERTAIN 2-ALKYL-SUBSTITUTED HETEROCYCLIC AMIDES |
CH440269A CH507650A (en) | 1968-03-25 | 1969-03-24 | Pesticides, especially fungicides, containing acrylamide compounds |
DE19691914954 DE1914954C3 (en) | 1968-03-25 | 1969-03-24 | Fungicides containing at least one oxygen heterocyclic amide as active ingredient |
ES365156A ES365156A1 (en) | 1968-03-25 | 1969-03-24 | Acrylamides and their use as fungicides |
SE7311762A SE416808B (en) | 1968-03-25 | 1973-08-29 | FURAN-RESPECTIVE DIHYDROFURAN-CARBOXANILIDE DERIVATIVES WITH VEGETABLE SYSTEMIC, FUNGICIDIC ACTIVITY |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1419868A GB1215066A (en) | 1968-03-25 | 1968-03-25 | Acrylamides and their use as fungicides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1215066A true GB1215066A (en) | 1970-12-09 |
Family
ID=10036828
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1419868A Expired GB1215066A (en) | 1968-03-25 | 1968-03-25 | Acrylamides and their use as fungicides |
Country Status (9)
Country | Link |
---|---|
BE (1) | BE730347A (en) |
CH (1) | CH507650A (en) |
DE (1) | DE1914954C3 (en) |
DK (1) | DK125505B (en) |
ES (1) | ES365156A1 (en) |
FR (1) | FR2004656A1 (en) |
GB (1) | GB1215066A (en) |
NL (1) | NL169183C (en) |
SE (1) | SE416808B (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5006658A (en) * | 1986-11-28 | 1991-04-09 | The Wellcome Foundation Ltd. | Pestidical pyridyloxy-dodeca-2,4-dienoates and phosphorimidates thereof |
US5380732A (en) * | 1986-11-28 | 1995-01-10 | Roussel-Uclaf | Pesticidal compounds |
US5416103A (en) * | 1992-09-21 | 1995-05-16 | Basf Aktiengesellschaft | N-cyclohex(en)yl-pyridine carboxamides and compositions containing them for controlling fungal pests |
US6107336A (en) * | 1996-07-24 | 2000-08-22 | Bayer Aktiengesellschaft | Dihydrofuran carboxamides |
WO2004018438A2 (en) * | 2002-08-22 | 2004-03-04 | Syngenta Participations Ag | Microbiocidal (e.g. fungicidal) 1,2,3-triazole derivatives |
WO2006094666A1 (en) * | 2005-03-05 | 2006-09-14 | Bayer Cropscience Ag | Heterobicyclic acrylamides |
US8785662B2 (en) | 2010-05-12 | 2014-07-22 | Sds Biotech K.K. | Anilide-based compounds for preserving wood and method of use thereof |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA932334A (en) * | 1969-02-13 | 1973-08-21 | Kulka Marshall | Furan-3-carboxamide derivatives and method of preparing same |
US3959481A (en) * | 1969-02-13 | 1976-05-25 | Uniroyal | Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives |
DE2019535C3 (en) * | 1970-04-23 | 1987-02-12 | Basf Ag, 6700 Ludwigshafen | 2,5-Dimethyl-furan-3-carboxylic acid cyclohexylamide and fungicidal agents containing this compound |
GB8726735D0 (en) * | 1987-11-14 | 1987-12-16 | Wellcome Found | Pesticidal compounds |
IL103614A (en) * | 1991-11-22 | 1998-09-24 | Basf Ag | Carboxamides for controlling botrytis and certain novel such compounds |
WO2000012495A1 (en) * | 1998-09-01 | 2000-03-09 | Basf Aktiengesellschaft | Use of dihydropyran carboxylic acid amides as herbicides and new dihydropyran carboxylic acid amides |
CN114031581B (en) * | 2021-12-27 | 2023-01-17 | 河南师范大学 | Method for synthesizing 2, 3-dihydrofuran compound |
-
1968
- 1968-03-25 GB GB1419868A patent/GB1215066A/en not_active Expired
-
1969
- 1969-03-24 FR FR6908564A patent/FR2004656A1/fr active Pending
- 1969-03-24 DE DE19691914954 patent/DE1914954C3/en not_active Expired
- 1969-03-24 BE BE730347D patent/BE730347A/xx not_active IP Right Cessation
- 1969-03-24 CH CH440269A patent/CH507650A/en not_active IP Right Cessation
- 1969-03-24 ES ES365156A patent/ES365156A1/en not_active Expired
- 1969-03-24 NL NL6904465A patent/NL169183C/en not_active IP Right Cessation
- 1969-03-24 DK DK160369A patent/DK125505B/en not_active IP Right Cessation
-
1973
- 1973-08-29 SE SE7311762A patent/SE416808B/en unknown
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5006658A (en) * | 1986-11-28 | 1991-04-09 | The Wellcome Foundation Ltd. | Pestidical pyridyloxy-dodeca-2,4-dienoates and phosphorimidates thereof |
US5380732A (en) * | 1986-11-28 | 1995-01-10 | Roussel-Uclaf | Pesticidal compounds |
US5416103A (en) * | 1992-09-21 | 1995-05-16 | Basf Aktiengesellschaft | N-cyclohex(en)yl-pyridine carboxamides and compositions containing them for controlling fungal pests |
US6107336A (en) * | 1996-07-24 | 2000-08-22 | Bayer Aktiengesellschaft | Dihydrofuran carboxamides |
WO2004018438A2 (en) * | 2002-08-22 | 2004-03-04 | Syngenta Participations Ag | Microbiocidal (e.g. fungicidal) 1,2,3-triazole derivatives |
WO2004018438A3 (en) * | 2002-08-22 | 2004-08-26 | Syngenta Participations Ag | Microbiocidal (e.g. fungicidal) 1,2,3-triazole derivatives |
JP2006502244A (en) * | 2002-08-22 | 2006-01-19 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | Compound |
US7531559B2 (en) | 2002-08-22 | 2009-05-12 | Syngenta Crop Protection, Inc. | Fungicidal 1,2,3 triazole derivatives |
CN100548992C (en) * | 2002-08-22 | 2009-10-14 | 辛根塔参与股份公司 | The 1,2,3-triazoles derivative of microbicidel (for example sterilization) |
US7956194B2 (en) | 2002-08-22 | 2011-06-07 | Syngenta Crop Protection, Inc. | Microbiocidal (E.G. fungicidal) 1,2,3-triazole derivatives |
WO2006094666A1 (en) * | 2005-03-05 | 2006-09-14 | Bayer Cropscience Ag | Heterobicyclic acrylamides |
US8785662B2 (en) | 2010-05-12 | 2014-07-22 | Sds Biotech K.K. | Anilide-based compounds for preserving wood and method of use thereof |
Also Published As
Publication number | Publication date |
---|---|
FR2004656A1 (en) | 1969-11-28 |
DE1914954C3 (en) | 1979-10-25 |
DE1914954A1 (en) | 1969-10-23 |
NL169183B (en) | 1982-01-18 |
DK125505B (en) | 1973-03-05 |
BE730347A (en) | 1969-09-24 |
SE416808B (en) | 1981-02-09 |
NL6904465A (en) | 1969-09-29 |
NL169183C (en) | 1987-01-16 |
DE1914954B2 (en) | 1977-08-18 |
CH507650A (en) | 1971-05-31 |
ES365156A1 (en) | 1971-02-01 |
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