GB1215066A - Acrylamides and their use as fungicides - Google Patents

Acrylamides and their use as fungicides

Info

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
Application number
GB1419868A
Inventor
Pieter Ten Haken
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB1419868A priority Critical patent/GB1215066A/en
Priority to NL6904465A priority patent/NL169183C/en
Priority to FR6908564A priority patent/FR2004656A1/fr
Priority to DE19691914954 priority patent/DE1914954C3/en
Priority to DK160369A priority patent/DK125505B/en
Priority to SE405969A priority patent/SE385262B/en
Priority to CH440269A priority patent/CH507650A/en
Priority to BE730347D priority patent/BE730347A/xx
Priority to ES365156A priority patent/ES365156A1/en
Publication of GB1215066A publication Critical patent/GB1215066A/en
Priority to SE7311762A priority patent/SE416808B/en
Expired legal-status Critical Current

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

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.
GB1419868A 1968-03-25 1968-03-25 Acrylamides and their use as fungicides Expired GB1215066A (en)

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
SE405969A SE385262B (en) 1968-03-25 1969-03-24 USE AS GROWTH SYSTEMIC FUNGICIDES OF CERTAIN 2-ALKYL-SUBSTITUTED HETEROCYCLIC AMIDES
FR6908564A FR2004656A1 (en) 1968-03-25 1969-03-24
DE19691914954 DE1914954C3 (en) 1968-03-25 1969-03-24 Fungicides containing at least one oxygen heterocyclic amide as active ingredient
DK160369A DK125505B (en) 1968-03-25 1969-03-24 Fungicide with plant systemic effect.
NL6904465A NL169183C (en) 1968-03-25 1969-03-24 PROCESS FOR PREPARING FUNGICIDE PREPARATIONS AND PROCESS FOR PREPARING ACRYLAMIDE DERIVATIVES SUITABLE FOR THIS
CH440269A CH507650A (en) 1968-03-25 1969-03-24 Pesticides, especially fungicides, containing acrylamide compounds
BE730347D BE730347A (en) 1968-03-25 1969-03-24
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
DE2019535B2 (en) * 1970-04-23 1973-04-05 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen 2,5-DIMETHYLFURAN-3-CARBONIC ACID CYCLOALKYLAMIDE AND FUNGICIDES CONTAINING THESE COMPOUNDS
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
AU5970799A (en) * 1998-09-01 2000-03-21 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

Cited By (12)

* Cited by examiner, † Cited by third party
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
NL169183B (en) 1982-01-18
DK125505B (en) 1973-03-05
BE730347A (en) 1969-09-24
NL169183C (en) 1987-01-16
FR2004656A1 (en) 1969-11-28
CH507650A (en) 1971-05-31
NL6904465A (en) 1969-09-29
ES365156A1 (en) 1971-02-01
DE1914954B2 (en) 1977-08-18
DE1914954C3 (en) 1979-10-25
SE416808B (en) 1981-02-09
DE1914954A1 (en) 1969-10-23

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