IE41140B1 - Fungicidal n-substituted furoic amide derivatives - Google Patents

Fungicidal n-substituted furoic amide derivatives

Info

Publication number
IE41140B1
IE41140B1 IE708/75A IE70875A IE41140B1 IE 41140 B1 IE41140 B1 IE 41140B1 IE 708/75 A IE708/75 A IE 708/75A IE 70875 A IE70875 A IE 70875A IE 41140 B1 IE41140 B1 IE 41140B1
Authority
IE
Ireland
Prior art keywords
formula
acid
prepared
compound
reacting
Prior art date
Application number
IE708/75A
Other versions
IE41140L (en
Original Assignee
Ciba Geigy Ag
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
Priority claimed from CH457274A external-priority patent/CH590608A5/en
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of IE41140L publication Critical patent/IE41140L/en
Publication of IE41140B1 publication Critical patent/IE41140B1/en

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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro 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
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
    • C07D307/24—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
    • C07D307/02—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
    • 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
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • 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
    • C07D333/26—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 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
    • C07D333/38—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)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

1448810 Furan derivatives CIBA-GEIGY AG 1 April 1975 [2 April 1974 10 Feb 1975] 13332/75 Heading C2C The invention comprises compounds of the Formula (I) in which R is H or methyl. They may be prepared by (a) acylating a compound of Formula (II) with furan (2)-carboxylic acid or an acid halide, anhydride or ester thereof, or (b) reacting a compound of Formula (III) with either an α-halopropionic acid methyl ester in the presence of an alkali metal carbonate, or with butyl lithium or sodium hydride to give the corresponding alkali metal salt, followed by reaction with an α-halopropionic acid methyl ester. The enantiomeric D-form of the compound of Formula (I) may be prepared by reacting the racemic compound of Formula (IV) in known manner with a nitrogen-containing optically active base to give the corresponding salt followed by fractional crystallization and liberation of the acid of Formula IV which is enriched with the optical D-antipode. The D- form of the ester of Formula (II) may then be prepared in conventional manner from the D form of the acid of Formula (IV), followed by acylation as in step (a) above, to give the D- form of the compound of Formula (I). The D- form of the acid of Formula (IV) may also be prepared by replacing the hydroxy group in L(+) lactic acid by halogen and reacting this product with 2,6-dimethylaniline or 2,3,6-trimethylaniline with reversal of the configuration. The compounds of Formula (II) may be prepared by reacting 2,6-dimethylaniline or 2,3,6- trimethylaniline with 2-bromopropionic acid methyl ester. The compounds of Formula (I) are used in fungicidal compositions. [GB1448810A]
IE708/75A 1974-04-02 1975-04-02 Fungicidal n-substituted furoic amide derivatives IE41140B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH457274A CH590608A5 (en) 1974-04-02 1974-04-02 N-Furoyl-N-aryl-alanine esters - prepd. e.g. by reacting N-aryl-alanine esters with 2-furoic acid or its derivs.
CH159175A CH603041A5 (en) 1974-04-02 1975-02-10 N-Furoyl-N-aryl-alanine esters

Publications (2)

Publication Number Publication Date
IE41140L IE41140L (en) 1975-10-02
IE41140B1 true IE41140B1 (en) 1979-10-24

Family

ID=25688094

Family Applications (2)

Application Number Title Priority Date Filing Date
IE709/75A IE41777B1 (en) 1974-04-02 1975-04-02 Fungicidal agents
IE708/75A IE41140B1 (en) 1974-04-02 1975-04-02 Fungicidal n-substituted furoic amide derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
IE709/75A IE41777B1 (en) 1974-04-02 1975-04-02 Fungicidal agents

Country Status (31)

Country Link
JP (3) JPS6042202B2 (en)
AR (2) AR205189A1 (en)
AT (2) AT343407B (en)
AU (1) AU465906B2 (en)
BG (2) BG26356A3 (en)
CA (2) CA1050546A (en)
CH (1) CH603041A5 (en)
CS (2) CS183789B2 (en)
DD (3) DD124733A5 (en)
DE (2) DE2560591C2 (en)
DK (2) DK141168B (en)
EG (2) EG12263A (en)
ES (2) ES436174A1 (en)
FI (2) FI750921A (en)
FR (2) FR2265747B1 (en)
GB (2) GB1498199A (en)
HU (2) HU172935B (en)
IE (2) IE41777B1 (en)
IL (2) IL46988A (en)
IT (2) IT1049394B (en)
LU (2) LU72174A1 (en)
NL (2) NL7503755A (en)
NO (2) NO141340C (en)
OA (2) OA04916A (en)
PH (2) PH11792A (en)
PL (2) PL98627B1 (en)
RO (3) RO73181A (en)
SE (2) SE419218B (en)
SU (4) SU743561A3 (en)
TR (2) TR18508A (en)
YU (2) YU39026B (en)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5845433B2 (en) * 1975-02-10 1983-10-08 チバ・ガイギ− アクチエンゲゼルシヤフト 2↓-Production method of furancarboxylic acid anilides
US4147792A (en) * 1977-02-04 1979-04-03 Ciba-Geigy Corporation Fungicidal compositions
CH629939A5 (en) * 1977-03-29 1982-05-28 Ciba Geigy Ag MICROBICIDAL AGENT.
DE2724785A1 (en) * 1977-05-27 1978-12-14 Schering Ag FURANCARBONIC ANILIDES, FUNGICIDALS CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PREPARATION
BG28977A3 (en) 1978-02-02 1980-08-15 Montedison Spa Fungicide means and method for fungus fighting
CH637368A5 (en) * 1978-10-27 1983-07-29 Ciba Geigy Ag ANILINE DERIVATIVES AND Pesticides Manufactured From Them.
EP0010673B1 (en) * 1978-10-31 1982-01-27 Bayer Ag Substituted n-propargyl anilines, process for their preparation and their use as fungicides
CH641760A5 (en) * 1978-11-27 1984-03-15 Ciba Geigy Ag PEST CONTROL.
CH639940A5 (en) * 1978-12-05 1983-12-15 Ciba Geigy Ag Substituted N-alkoxycarbonylethyl-N-acylanilines, microbicides containing them, and process for the preparation of the compounds
DE2948734A1 (en) * 1978-12-07 1980-06-19 Ciba Geigy Ag PEST CONTROL
DE2940189A1 (en) * 1979-10-04 1981-04-16 Basf Ag, 6700 Ludwigshafen ISOXAZOLYLCARBONIC ACID ANILIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES
MA19111A1 (en) * 1979-10-26 1981-12-31 Ciba Geigy Ag HOMOSERIN DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MICROBICIDES
DE3013908A1 (en) * 1980-04-11 1981-10-22 Basf Ag, 6700 Ludwigshafen 2- (N-ARYL-, N-ISOXAZOLYLCARBONYL) -AMINOBUTYROLACTONE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM
MA19215A1 (en) * 1980-07-25 1982-04-01 Ciba Geigy Ag NOVEL ARYLAMINE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND USE AS MICROBICIDES.
DE3030736A1 (en) 1980-08-14 1982-03-25 Basf Ag, 6700 Ludwigshafen N-DISUBSTITUTED ANILINE DERIVATIVES, THEIR PRODUCTION, THEIR USE AS MICROBICIDES AND AGENTS THEREFOR
EP0061836B1 (en) * 1981-03-19 1986-12-30 Imperial Chemical Industries Plc Amide derivatives, processes for preparing them, their use as fungicides and pesticidal compositions containing them
DE3133418A1 (en) * 1981-08-24 1983-03-10 Basf Ag, 6700 Ludwigshafen THIAZOLYL AND ISOTHIAZOLYLCARBONIC ACID ANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES
JPH0326906U (en) * 1989-07-26 1991-03-19
DE4011172A1 (en) * 1990-04-06 1991-10-10 Degussa COMPOUNDS FOR CONTROLLING PLANT DISEASES
DE4304172A1 (en) 1993-02-12 1994-08-25 Bayer Ag Fungicidal active ingredient combinations
US5723491A (en) * 1994-07-11 1998-03-03 Novartis Corporation Fungicidal composition and method of controlling fungus infestation
DE4429014A1 (en) 1994-08-16 1996-02-22 Basf Ag Process for the preparation of cyclic amines
AR011515A1 (en) * 1996-12-25 2000-08-30 Agrogene Ltd DERIVED FROM AMINOBUTIRIC ACID FOR THE PROTECTION OF PLANTS FROM FUNGAL DISEASES AND A METHOD TO PROTECT A CROP AGAINST FUNGAL DISEASES, FOR EXAMPLE, TOMATOES AND POTATOES AGAINST LATE, EARLY MILK, VINEYARD ELVIO, AND
DE10347090A1 (en) 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistic fungicidal drug combinations
DE10349501A1 (en) 2003-10-23 2005-05-25 Bayer Cropscience Ag Synergistic fungicidal drug combinations
DE102004049761A1 (en) 2004-10-12 2006-04-13 Bayer Cropscience Ag Fungicidal drug combinations
DE102005026482A1 (en) 2005-06-09 2006-12-14 Bayer Cropscience Ag Active substance combination, useful e.g. for combating unwanted phytopathogenic fungus, comprises herbicides e.g. glyphosate and active substances e.g. strobilurin, triazoles, valinamide and carboxamide
CA2916460C (en) 2005-06-09 2017-10-03 Klaus Stenzel Combinations comprising prothioconazole and gulfosinate
DE102006023263A1 (en) 2006-05-18 2007-11-22 Bayer Cropscience Ag Synergistic drug combinations
JP2010503642A (en) 2006-09-18 2010-02-04 ビーエーエスエフ ソシエタス・ヨーロピア Ternary pesticide mixture
CN101605461A (en) 2007-02-06 2009-12-16 巴斯夫欧洲公司 Pesticide combination
EP2000028A1 (en) 2007-06-06 2008-12-10 Bayer CropScience Aktiengesellschaft Fungicidal active agent compounds
EP2000030A1 (en) 2007-06-06 2008-12-10 Bayer CropScience AG Fungicidal active agent compounds
DE102007045920B4 (en) 2007-09-26 2018-07-05 Bayer Intellectual Property Gmbh Synergistic drug combinations
IN2012DN01345A (en) 2009-07-16 2015-06-05 Bayer Cropscience Ag
EP2910126A1 (en) 2015-05-05 2015-08-26 Bayer CropScience AG Active compound combinations having insecticidal properties
CN115557887A (en) * 2022-11-10 2023-01-03 南京林业大学 Synthesis of trifluoromethyl pyridine derivative based on Ugi reaction and biological activity research of trifluoromethyl pyridine derivative

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3959481A (en) * 1969-02-13 1976-05-25 Uniroyal Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives
JPS5345364A (en) * 1976-10-06 1978-04-24 Daiahoiru Kk Device for controlling extrusion molding die bolt

Also Published As

Publication number Publication date
DK135975A (en) 1975-10-03
DK141168C (en) 1980-07-14
IT1048806B (en) 1980-12-20
DE2513788A1 (en) 1975-10-09
BG26356A3 (en) 1979-03-15
DE2513732C2 (en) 1988-04-14
NL7503755A (en) 1975-10-06
ES436175A1 (en) 1977-04-16
PH11792A (en) 1978-07-05
TR18508A (en) 1977-03-04
DE2513732A1 (en) 1975-10-16
FI750920A (en) 1975-10-03
NO751084L (en) 1975-10-03
FR2265747A1 (en) 1975-10-24
YU82775A (en) 1982-08-31
JPS5345364B2 (en) 1978-12-06
SU743561A3 (en) 1980-06-25
CS183789B2 (en) 1978-07-31
DD118785A5 (en) 1976-03-20
BG24651A3 (en) 1978-04-12
HU173317B (en) 1979-04-28
FR2265748B1 (en) 1978-02-03
IE41777L (en) 1975-10-02
JPS50135226A (en) 1975-10-27
NO751086L (en) 1975-10-03
ATA244875A (en) 1977-09-15
LU72175A1 (en) 1977-02-01
RO84021A (en) 1984-05-12
JPS53135964A (en) 1978-11-28
IL46988A (en) 1977-12-30
SE7503517L (en) 1975-10-03
EG11640A (en) 1977-10-31
RO84021B (en) 1984-06-30
TR18339A (en) 1977-05-10
SU626690A3 (en) 1978-09-30
YU40259B (en) 1985-12-31
DK141995B (en) 1980-08-04
SU628812A3 (en) 1978-10-15
DE2513788B2 (en) 1977-06-30
YU82875A (en) 1982-05-31
PH13072A (en) 1979-11-23
NO142714C (en) 1980-10-01
YU39026B (en) 1984-02-29
LU72174A1 (en) 1976-03-02
NL160821B (en) 1979-07-16
OA04916A (en) 1980-10-31
IL46989A0 (en) 1975-06-25
AR205189A1 (en) 1976-04-12
GB1498199A (en) 1978-01-18
DD124733A5 (en) 1977-03-09
FI750921A (en) 1975-10-03
AU7964175A (en) 1976-09-30
PL98627B1 (en) 1978-05-31
JPS6042202B2 (en) 1985-09-20
IT1049394B (en) 1981-01-20
DD118510A5 (en) 1976-03-12
CA1050558A (en) 1979-03-13
JPS50135225A (en) 1975-10-27
JPS5740829B2 (en) 1982-08-30
FI63567B (en) 1983-03-31
FI63567C (en) 1983-07-11
IE41777B1 (en) 1980-03-26
NO141340C (en) 1980-02-20
AU7964075A (en) 1975-10-09
SE418086B (en) 1981-05-04
AU465906B2 (en) 1975-10-09
ATA244675A (en) 1978-01-15
DK135875A (en) 1975-10-03
EG12263A (en) 1978-12-31
SU682096A3 (en) 1979-08-25
AR224602A1 (en) 1981-12-30
FR2265748A1 (en) 1975-10-24
AT345614B (en) 1978-09-25
CH603041A5 (en) 1978-08-15
PL97786B1 (en) 1978-03-30
SE7503518L (en) 1975-10-03
RO73181A (en) 1982-10-11
FR2265747B1 (en) 1977-04-15
DE2560591C2 (en) 1989-06-08
AT343407B (en) 1978-05-26
OA04918A (en) 1980-10-31
DK141168B (en) 1980-01-28
ES436174A1 (en) 1977-04-16
NL7503754A (en) 1975-10-06
IL46988A0 (en) 1975-06-25
RO79677A (en) 1982-08-17
NL160821C (en) 1979-12-17
CS183788B2 (en) 1978-07-31
CA1050546A (en) 1979-03-13
GB1448810A (en) 1976-09-08
HU172935B (en) 1979-01-28
NO142714B (en) 1980-06-23
SE419218B (en) 1981-07-20
IL46989A (en) 1978-06-15
IE41140L (en) 1975-10-02
NO141340B (en) 1979-11-12
DK141995C (en) 1980-12-15

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