GB1494877A - Heterocyclic compounds and plant growth regulating compositions - Google Patents

Heterocyclic compounds and plant growth regulating compositions

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Publication number
GB1494877A
GB1494877A GB515/76A GB51576A GB1494877A GB 1494877 A GB1494877 A GB 1494877A GB 515/76 A GB515/76 A GB 515/76A GB 51576 A GB51576 A GB 51576A GB 1494877 A GB1494877 A GB 1494877A
Authority
GB
United Kingdom
Prior art keywords
formula
compounds
compound
cor
prepared
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
GB515/76A
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.)
Commonwealth Scientific and Industrial Research Organization CSIRO
Original Assignee
Commonwealth Scientific and Industrial Research Organization CSIRO
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 Commonwealth Scientific and Industrial Research Organization CSIRO filed Critical Commonwealth Scientific and Industrial Research Organization CSIRO
Publication of GB1494877A publication Critical patent/GB1494877A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—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
    • 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
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (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)

Abstract

1494877 Diphenyl heterocyclic compounds COMMONWEALTH SCIENTIFIC & INDUSTRIAL RESEARCH ORGANIZATION 7 Jan 1976 [10 Jan 1975] 515/76 Heading C2C The invention comprises compounds of general Formula I wherein each of R<SP>1</SP> to R<SP>10</SP>, which may be the same or different, is hydrogen, lower alkyl, halogen, amino, nitro, cyano or -COR<SP>11</SP> wherein R<SP>11</SP> is hydroxy, lower alkoxy, aralkoxy, aryloxy, substituted or unsubstituted amino or -O<SP>#</SP>] n M<SP>n#</SP> or -S#] n M<SP>n#</SP> wherein M<SP>n#</SP> is an ammonium, alkali metal or alkaline earth metal ion and n is 1 or 2 accordingly, R<SP>1</SP> or R<SP>10</SP> being -COR<SP>11</SP>, and wherein Q is a heterocyclic ring of general formula (A) or (B) wherein X is oxygen, sulphur, or substituted or unsubstituted secondary amino nitrogen, and each of Y and Z, which may be the same or different, is imino nitrogen or unsubstituted methine, subject to the proviso that, when Q is a ring of general formula (B) wherein Y is unsubstituted methine and X is substituted or unsubstituted secondary amino nitrogen, then Z is other than imino nitrogen. Compounds of Formula I in which Q is 1,2,4- triazole, 1,3,4-oxadiazole or 1,3,4-thiadiazole may be prepared by oxidizing a compound of Formula I in which R<SP>1</SP> or R<SP>10</SP> is alkyl to convert the latter to -COR<SP>11</SP>. Compounds of Formula I in which Q is isooxazole may be prepared by cyclizing a compound of formula (which itself may be obtained from the corresponding diketone and hydroxylamine). Compounds of Formula I in which Q is isooxazole and R<SP>5</SP> is -COR<SP>11</SP> may be obtained by reacting with hydroxylamine a compound of Formula III where X<SP>1</SP> is halogen. Compounds of Formula I where Q is 1,3,4-oxadiazole may be prepared by cyclizing a compound of Formula IV Compounds of Formula I where Q is thiazolyl may be prepared by reacting together the two compounds The precursor of Formula III, X = Br and all R's = H, is obtained by bromination of the corresponding compound (α-phenacyl phthalide) in which X=H, which is obtained from 2- carboxybenzaldehyde and acetophenone. (IV), R<SP>5</SP> = -COOH and other R's=H, is obtained from benzyl hydrazide and 2-carboxybenzaldehyde. o-Carboxyphenacyl bromide (obtained by bromination of o-carboxyacetophenone) with thiobenzamide in ethanol gives 2-phenyl-4-(oethoxycarbonylphenyl)-thiazole the ester group of which is then hydrolysed to the corresponding acid group. o-Toluylhydrazide with benzonitrile gave 3-o-tolyl-5-phenyl-1,2,4-triazole, the methyl group of which is oxidized to the carboxyl group. Compounds of Formula I, may be used to regulate the growth of plants.
GB515/76A 1975-01-10 1976-01-07 Heterocyclic compounds and plant growth regulating compositions Expired GB1494877A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AUPC023575 1975-01-10

Publications (1)

Publication Number Publication Date
GB1494877A true GB1494877A (en) 1977-12-14

Family

ID=3766094

Family Applications (1)

Application Number Title Priority Date Filing Date
GB515/76A Expired GB1494877A (en) 1975-01-10 1976-01-07 Heterocyclic compounds and plant growth regulating compositions

Country Status (13)

Country Link
AU (1) AU497898B2 (en)
BE (1) BE837454A (en)
BR (1) BR7600132A (en)
CA (1) CA1066708A (en)
CH (1) CH603044A5 (en)
DE (1) DE2600655A1 (en)
FR (1) FR2332705A1 (en)
GB (1) GB1494877A (en)
IL (1) IL48803A0 (en)
IT (1) IT1054759B (en)
NL (1) NL7600152A (en)
NZ (1) NZ179684A (en)
ZA (1) ZA7638B (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4197405A (en) * 1979-02-22 1980-04-08 Monsanto Company Thermolysis of 3'-(Aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one
US4208510A (en) * 1978-12-20 1980-06-17 Monsanto Company Preparation of 3-aryl-isoxazol-5-yl benzoates
US4209629A (en) * 1978-12-20 1980-06-24 Monsanto Company 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones
US4210762A (en) * 1978-08-17 1980-07-01 Monsanto Company 2[5-(3-Trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl] benzoates
US4223154A (en) * 1979-03-09 1980-09-16 Monsanto Company Preparation of 2-(3-aryl-5-isoxazol) benzoyl halide
US4230866A (en) * 1979-05-17 1980-10-28 Monsanto Company Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof
US4268299A (en) * 1978-08-17 1981-05-19 Monsanto Company Method and composition for plant growth regulation containing trifluoromethyl 1,3,4 oxadiazol benzoates
US4401457A (en) 1980-06-18 1983-08-30 Monsanto Company 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as herbicides
JP2008515985A (en) * 2004-10-13 2008-05-15 ピーティーシー セラピューティクス，インコーポレーテッド Nonsense-inhibiting compounds and methods of use
JP2011525534A (en) * 2008-06-24 2011-09-22 アイアールエム・リミテッド・ライアビリティ・カンパニー Compounds and methods for modulating G protein coupled receptors
CN114773330A (en) * 2022-05-24 2022-07-22 贵州医科大学 Butylphthalide-oxa/thiadiazole compound and preparation method and application thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1579352A (en) * 1977-05-06 1980-11-19 Lepetit Spa 3,5-disubstituted-1h-1,2,4-triazoles
US4135910A (en) 1977-05-12 1979-01-23 Monsanto Company Oxadiazol-3-yl-benzoates as plant growth regulants
US4140515A (en) 1977-05-12 1979-02-20 Monsanto Company Aryl-3-isoxazole benzoates as plant growth regulants and herbicides
US4229204A (en) * 1978-12-04 1980-10-21 Monsanto Company Trifluoromethylphenyl isoxazolyl benzoates
DE3623302A1 (en) * 1985-11-09 1987-05-14 Bayer Ag NICOTINE ACID DERIVATIVES

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1024971B (en) * 1956-11-05 1958-02-27 Bayer Ag Process for the preparation of 2,5-diaryl-1,3,4-oxdiazoles
FR1368390A (en) * 1963-07-25 1964-07-31 Basf Ag Process for the production of chlorides of heterocyclic carboxylic acids and of heterocyclic carboxylic acids

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4268299A (en) * 1978-08-17 1981-05-19 Monsanto Company Method and composition for plant growth regulation containing trifluoromethyl 1,3,4 oxadiazol benzoates
US4210762A (en) * 1978-08-17 1980-07-01 Monsanto Company 2[5-(3-Trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl] benzoates
US4208510A (en) * 1978-12-20 1980-06-17 Monsanto Company Preparation of 3-aryl-isoxazol-5-yl benzoates
US4209629A (en) * 1978-12-20 1980-06-24 Monsanto Company 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones
US4364768A (en) 1978-12-20 1982-12-21 Monsanto Company 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as plant growth regulants
US4197405A (en) * 1979-02-22 1980-04-08 Monsanto Company Thermolysis of 3'-(Aryl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-one
US4223154A (en) * 1979-03-09 1980-09-16 Monsanto Company Preparation of 2-(3-aryl-5-isoxazol) benzoyl halide
US4230866A (en) * 1979-05-17 1980-10-28 Monsanto Company Preparation of 3-aryl-isoxazol-5-yl-benzoic acid and salts thereof
US4401457A (en) 1980-06-18 1983-08-30 Monsanto Company 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones and their use as herbicides
JP2008515985A (en) * 2004-10-13 2008-05-15 ピーティーシー セラピューティクス，インコーポレーテッド Nonsense-inhibiting compounds and methods of use
US9611230B2 (en) 2004-10-13 2017-04-04 Ptc Therapeutics, Inc. 1,3,4-oxadiazole benzoic acid compounds and their use for nonsense suppression and the treatment of disease
JP2011525534A (en) * 2008-06-24 2011-09-22 アイアールエム・リミテッド・ライアビリティ・カンパニー Compounds and methods for modulating G protein coupled receptors
CN114773330A (en) * 2022-05-24 2022-07-22 贵州医科大学 Butylphthalide-oxa/thiadiazole compound and preparation method and application thereof
CN114773330B (en) * 2022-05-24 2024-03-15 贵州医科大学 Butylphthalide-oxa/thiadiazole compound and preparation method and application thereof

Also Published As

Publication number Publication date
NL7600152A (en) 1976-07-13
BR7600132A (en) 1976-08-03
IL48803A0 (en) 1976-03-31
FR2332705A1 (en) 1977-06-24
AU1007876A (en) 1977-07-14
CH603044A5 (en) 1978-08-15
AU497898B2 (en) 1979-01-18
NZ179684A (en) 1978-04-03
ZA7638B (en) 1976-12-29
CA1066708A (en) 1979-11-20
IT1054759B (en) 1981-11-30
BE837454A (en) 1976-07-09
DE2600655A1 (en) 1976-07-15

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Legal Events

Date Code Title Description
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
SP Amendment (slips) printed
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee