GB1497189A - Substituted 4-phenylurazoles and their use in agricultural fungicide compositions - Google Patents

Substituted 4-phenylurazoles and their use in agricultural fungicide compositions

Info

Publication number
GB1497189A
GB1497189A GB5027775A GB5027775A GB1497189A GB 1497189 A GB1497189 A GB 1497189A GB 5027775 A GB5027775 A GB 5027775A GB 5027775 A GB5027775 A GB 5027775A GB 1497189 A GB1497189 A GB 1497189A
Authority
GB
United Kingdom
Prior art keywords
formula
reacting
dichlorophenyl
compound
urazole
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
GB5027775A
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.)
Mitsubishi Kasei Corp
Original Assignee
Mitsubishi Kasei Corp
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 JP49140224A external-priority patent/JPS5167728A/en
Priority claimed from JP49143183A external-priority patent/JPS5170820A/en
Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp
Publication of GB1497189A publication Critical patent/GB1497189A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
    • 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
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1497189 Substituted phenyl urazoles MITSUBISHI CHEMICAL INDUSTRIES Ltd 8 Dec 1975 [6 Dec 1974 13 Dec 1974] 50277/75 Heading C2C The invention comprises compounds of the formula wherein X and Y are each O or S, R 1 and R 2 are H, alkyl, alkenyl, alkynyl, aryl which may be substituted by halogen or alkyl; alkanoyl, alkylcarbamoyl, alkoxycarbonyl, alkylthiocarbamoyl or (alkylthio)thiocarbonyl (provided that R 1 and R 2 are not both H when X and Y are both oxygen) or R 1 and R 2 together form a (C 3 -C 8 ) alkylene radical which may have CH 3 substituents as branches. They may be obtained by (a) reacting an alkali metal, alkaline earth metal or NH 4 salt of 4-(3<SP>1</SP>,5<SP>1</SP>-dichlorophenyl) urazole with a halide of formula RHal wherein R is R<SP>1</SP> or R<SP>2</SP> to give either a product in which R<SP>1</SP> and R<SP>2</SP> are the same, or a product in which R<SP>1</SP> is R and R<SP>2</SP> is H and, if required, further reacting with a different halide of formula RHal to give a product in which R<SP>1</SP> and R<SP>2</SP> are different; (b) reacting 4-(3<SP>1</SP>,5<SP>1</SP>-dichlorophenyl) urazole in one or more stages with an isocyanate or isothiocyanate of the formula R<SP>4</SP>NCX wherein R<SP>4</SP> is alkyl and X is O or S; (c) when one or both of X and Y is S, reacting a compound of Formula I in which X and Y are both O with P 2 S 5 ; (d) reacting a 1,2-disubstituted-1-alkoxycarbonyl hydrazine of the formula wherein R 5 is lower alkyl, with 3,5-dichlorophenyl isocyanate or isothiocyanate, and cyclizing the resulting carbamoyl- or thiocarbamoyl - hydrazine by treating the carbamoyl-hydrazine with KOH or NaOC 2 H 5 and heating the thiocarbamoyl-hydrazine; (e) Diels-Alder condensation of 4-(3<SP>1</SP>,5<SP>1</SP>-dichlorophenyl)urazole with a diene of the formula wherein R<SP>6</SP>, R<SP>7</SP>, R<SP>8</SP> and R<SP>9</SP> are each H or CH 3 , to give a compound of the formula and then hydrogenating this compound to give a compound of the formula or (f) when R 1 and R 2 together form a (C 3 -C a ) alkylene radical which may have CH 3 substituents, reacting a monovalent or bivalent metal salt of amine salt of 4-(3<SP>1</SP>,5<SP>1</SP>-dichlorophenyl)urazole with an alkylene dihalide. A fungicidal composition comprises a compound of Formula I above together with a carrier or diluent. It is useful in preventing rice sheath blight disease, Botrysis gray mould disease, rice brown spot disease, Altemaria leaf spot and Sclerotinia spot disease.
GB5027775A 1974-12-06 1975-12-08 Substituted 4-phenylurazoles and their use in agricultural fungicide compositions Expired GB1497189A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP49140224A JPS5167728A (en) 1974-12-06 1974-12-06 Noengeiyosatsukinzai
JP49143183A JPS5170820A (en) 1974-12-13 1974-12-13 Noengeiyosatsukinzai

Publications (1)

Publication Number Publication Date
GB1497189A true GB1497189A (en) 1978-01-05

Family

ID=26472819

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5027775A Expired GB1497189A (en) 1974-12-06 1975-12-08 Substituted 4-phenylurazoles and their use in agricultural fungicide compositions

Country Status (9)

Country Link
AU (1) AU503321B2 (en)
BR (1) BR7508049A (en)
CA (1) CA1047399A (en)
DE (1) DE2554866A1 (en)
ES (6) ES443296A1 (en)
FR (1) FR2293147A1 (en)
GB (1) GB1497189A (en)
IT (1) IT1051334B (en)
NL (1) NL7514191A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4866058A (en) * 1988-07-27 1989-09-12 Izydore Robert A Method for control of hyperlipidemia
US5034528A (en) * 1988-07-27 1991-07-23 North Carolina Central University Compositions for the control of hyperlipidemia

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4276420A (en) * 1978-05-24 1981-06-30 Chevron Research Company Herbicidal and plant-growth-regulating 1,2,4-trisubstituted-1,2,4-triazolidin-3-one-5-thione
US4326878A (en) * 1979-02-09 1982-04-27 Chevron Research Herbicidal and plant-growth-regulating 1,2,4-trisubstituted-1,2,4-triazolidin-3,5-dithiones
IT1113389B (en) * 1979-05-11 1986-01-20 Montedison Spa ANTIBOTRITIC PYRAZOL-TRIAZOLE-TRIONI
DE3027551A1 (en) * 1980-07-21 1982-02-18 Bayer Ag, 5090 Leverkusen NEW HYDROXIALKYL-1,2,4-TRIAZOLIDINE-3,5-DIONE AND A METHOD FOR THEIR PRODUCTION
JP2016526539A (en) 2013-06-20 2016-09-05 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Aryl sulfide and aryl sulfoxide derivatives as acaricides and insecticides
JP2016526538A (en) 2013-06-20 2016-09-05 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Aryl sulfide and aryl sulfoxide derivatives as acaricides and insecticides
ES2728531T3 (en) 2013-07-08 2019-10-25 Bayer Cropscience Ag Six-membered arylsulfide and C-N-linked arylsulfoxide derivatives as agents to fight parasites
AR102942A1 (en) 2014-12-11 2017-04-05 Bayer Cropscience Ag DERIVATIVES OF ARILSULFIDE AND ARILSULPHOXIDE OF FIVE C-N-CONNECTED MEMBERS, AS PESTICIDES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4866058A (en) * 1988-07-27 1989-09-12 Izydore Robert A Method for control of hyperlipidemia
US5034528A (en) * 1988-07-27 1991-07-23 North Carolina Central University Compositions for the control of hyperlipidemia

Also Published As

Publication number Publication date
FR2293147A1 (en) 1976-07-02
AU8716075A (en) 1977-06-09
ES458721A1 (en) 1978-11-16
ES462304A1 (en) 1978-05-16
ES458720A1 (en) 1978-08-01
NL7514191A (en) 1976-06-09
ES458719A1 (en) 1978-07-16
FR2293147B1 (en) 1978-05-12
ES443296A1 (en) 1977-09-01
DE2554866A1 (en) 1976-06-16
IT1051334B (en) 1981-04-21
ES462305A1 (en) 1978-05-16
CA1047399A (en) 1979-01-30
AU503321B2 (en) 1979-08-30
BR7508049A (en) 1976-08-24

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee