GB1422430A - Derivatives of 3-thioallophanic acid - Google Patents

Derivatives of 3-thioallophanic acid

Info

Publication number
GB1422430A
GB1422430A GB5630973A GB5630973A GB1422430A GB 1422430 A GB1422430 A GB 1422430A GB 5630973 A GB5630973 A GB 5630973A GB 5630973 A GB5630973 A GB 5630973A GB 1422430 A GB1422430 A GB 1422430A
Authority
GB
United Kingdom
Prior art keywords
formula
methyl
compound
substituted
nitro
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
GB5630973A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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 US00325783A external-priority patent/US3852278A/en
Priority claimed from US325277A external-priority patent/US3860586A/en
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB1422430A publication Critical patent/GB1422430A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • 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
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • 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
    • C07D333/28—Halogen atoms

Landscapes

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

Abstract

1422430 3-Thioallophonic acid derivatives ROHM & HAAS CO 5 Dec 1973 [22 Jan 1973 (2)] 56309/73 Heading C2C Novel compounds have the Formula I wherein X is R<SP>1</SP>O- or R<SP>1</SP>S-, R<SP>1</SP> being: (a) alkyl, straight or branched, of 1 to 12 carbon atoms, (b) alkyl or 1 to 12 carbon atoms substituted with halo, preferably chloro, or methoxy groups, (c) alkenyl of 2 to 12 carbon atoms, (d) alkynyl of 3 to 12 carbon atoms, (e) phenyl, (f) phenyl substituted with halo (preferably chloro) methyl, methoxy or nitro, (g) benzyl or (h) benzyl substituted in the ring with halo (preferably chloro) methyl, methoxy or nitro; Y is a heterocyclic radical having 5 or 6 cyclic atoms and having as a hetero atom O, S or N or any combination of two of these wherein the total number of hetero atoms is up to three and the acetoxymethyl, chloro, methyl or nitro substituted derivatives of these; R is hydrogen or methyl; Z is halo (preferably chloro) methyl, methoxy or nitro and n is 0 to 3. The compounds of Formula I are prepared by (A) reacting a compound of formula R-CO-Y with a compound of formula or (B) reacting a compound of formula with a compound of formula the use of a base being necessary in (A) or (B) when reactions of acid-sensitive aldehydes or their Schiff bases are involved. In particular, compounds of Formula VII wherein W is hydrogen, acetoxymethyl, chloro, methyl or nitro, are obtained by reacting a compound of formula with a compound of formula, X-CO-NCS in the presence of an inert solvent and 0À5-20 mole per cent based on the heterocyclic reactant of a tertiary amine whose dissociation constant at 25‹ C. is in the range of 5 Î 10<SP>-3</SP> to 5 Î 10<SP>-5</SP> (e.g. trimethylamine, triethylamine, tripropylamine, triisobutylamine, methyldiethylamine, tetramethylethylenediamine, N,N-dimethylethanolamine and dimethylaniline). Examples prepare compounds of Formula I wherein Y is 2-furyl optionally 5-substituted by CH 3 -, CH 3 CO.OCH 2 - or NO 2 groups, 2- thienyl optionally 5-substituted by chlorine, 2-pyrryl, 2-(N-methyl)pyrryl, 5-isothiazolyl or 2-pyridyl. Other specified heterocyclic radicals Y are thiazolyl, imidazolyl, isoxazolyl, oxadiazolyl, oxazolyl, pyrimidyl, thiadiazolyl, triazinyl and triazolyl. The compounds of Formula I (and VII) are fungicides and show anthelmintic activity.
GB5630973A 1973-01-22 1973-12-05 Derivatives of 3-thioallophanic acid Expired GB1422430A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US00325783A US3852278A (en) 1973-01-22 1973-01-22 Preparation of 4-(2-(furfurylideneamino)-phenyl)-3-thioallophanates
US325277A US3860586A (en) 1973-01-22 1973-01-22 Derivatives of 4-(2-aminophenyl)-3-thioallophanic acid

Publications (1)

Publication Number Publication Date
GB1422430A true GB1422430A (en) 1976-01-28

Family

ID=26984860

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5630973A Expired GB1422430A (en) 1973-01-22 1973-12-05 Derivatives of 3-thioallophanic acid

Country Status (16)

Country Link
AR (1) AR209581A1 (en)
AU (1) AU6271173A (en)
BR (1) BR7400131D0 (en)
DD (2) DD110845A5 (en)
DE (1) DE2401388A1 (en)
ES (1) ES422691A1 (en)
FR (1) FR2318155A1 (en)
GB (1) GB1422430A (en)
IL (1) IL44040A (en)
IT (1) IT1048422B (en)
KE (1) KE2735A (en)
MY (1) MY7700210A (en)
NL (1) NL7400878A (en)
OA (1) OA04656A (en)
PL (1) PL90691B1 (en)
SU (1) SU547169A4 (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE759473A (en) * 1969-11-29 1971-05-26 Bayer Ag
JPS4832641B1 (en) * 1970-08-20 1973-10-08

Also Published As

Publication number Publication date
FR2318155A1 (en) 1977-02-11
NL7400878A (en) 1974-07-24
DD110845A5 (en) 1975-01-12
ES422691A1 (en) 1976-08-01
KE2735A (en) 1977-05-27
IT1048422B (en) 1980-11-20
FR2318155B1 (en) 1978-01-13
OA04656A (en) 1980-07-31
IL44040A (en) 1977-05-31
BR7400131D0 (en) 1974-08-22
AR209581A1 (en) 1977-05-13
IL44040A0 (en) 1974-05-16
PL90691B1 (en) 1977-01-31
DD114494A5 (en) 1975-08-12
MY7700210A (en) 1977-12-31
SU547169A4 (en) 1977-02-15
DE2401388A1 (en) 1974-07-25
AU6271173A (en) 1975-05-22

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee