GB1334015A - Substituted thiophenes and their use as herbicides - Google Patents

Substituted thiophenes and their use as herbicides

Info

Publication number
GB1334015A
GB1334015A GB1334015DA GB1334015A GB 1334015 A GB1334015 A GB 1334015A GB 1334015D A GB1334015D A GB 1334015DA GB 1334015 A GB1334015 A GB 1334015A
Authority
GB
United Kingdom
Prior art keywords
atoms
alkyl
reacting
substituted
halogen
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
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
Publication of GB1334015A publication Critical patent/GB1334015A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

Abstract

1334015 Substituted thiophenes SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 26 Aug 1971 40036/71 Heading C2C The invention comprises compounds of the formula wherein either (a) W is -NHC(O)R and each of X, Y and Z which may be the same or different is hydrogen or halogen or (b) Z is -NHC(O)R, X is halogen, Y is hydrogen or halogen and W is halogen or R<SP>1</SP>S(O) n -; R<SP>1</SP> being alkyl of 1-4 C atoms, or cycloalkyl of 3 or 4 C atoms, or alkyl of 1-4 C atoms substituted by chlorine; n being 0, 1 or 2 and R being (i) alkyl of 1-6 C atoms or (ii) alkyl of 1-6 C atoms substituted by chlorine or bromine or (iii) cycloalkyl of 3-6 C atoms or (iv) -NR<SP>2</SP>R<SP>3</SP> wherein each of R<SP>2</SP> and R<SP>3</SP>, which may be the same or different, is hydrogen, alkyl of 1-4 C atoms, or alkyl of 1-4 C atoms substituted by chlorine, or (v) -OR<SP>4</SP>, wherein R<SP>4</SP> is is alkyl of 1-6 C atoms, or alkenyl of 1-6 C atoms, or one of these substituted by chlorine, or cycloalkyl of 3-6 C atoms. The thienyl amide compounds are prepared by reacting a thiophene, optionally substituted by halogen and/or R<SP>1</SP>S(O) n -, with H 2 SO 4 /HNO 3 , reducing the resulting nitrothiophene with tin dust to the corresponding aminothiophene and then reacting the latter with an acyl halide (e.g. R.CO.Cl). The thienyl urea compounds are prepared by reacting the aminothiophenes with phosgene in ethyl acetate to give the corresponding thiophene isocyanate and then reacting the latter with an amine, i.e. HNR<SP>2</SP>R<SP>3</SP>. The thienyl carbamates are obtained by reacting the corresponding thiophene isocyanates with alcohols, i.e. R<SP>4</SP>OH. Alternatively, the thiophene isocyanates may be prepared by reacting the corresponding acid chloride with sodium azide. The invention also comprises herbicidal compositions comprising the substituted thiophenes together with an adjuvant therefor.
GB1334015D 1971-08-26 1971-08-26 Substituted thiophenes and their use as herbicides Expired GB1334015A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4003671 1971-08-26

Publications (1)

Publication Number Publication Date
GB1334015A true GB1334015A (en) 1973-10-17

Family

ID=10412848

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1334015D Expired GB1334015A (en) 1971-08-26 1971-08-26 Substituted thiophenes and their use as herbicides

Country Status (1)

Country Link
GB (1) GB1334015A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4187232A (en) * 1975-06-05 1980-02-05 Lilly Industries Limited Acylamino derivatives
AT382870B (en) * 1982-02-09 1987-04-27 Sandoz Ag Process for the preparation of novel chloroacetamides
EP0273602A1 (en) * 1986-12-05 1988-07-06 Eli Lilly And Company 3-Cyano-4-arylthiophenes
US5158598A (en) * 1988-08-04 1992-10-27 Basf Aktiengesellschaft Bithienyl derivatives, and herbicidal use for agents containing them
WO2010126167A1 (en) * 2009-04-30 2010-11-04 住友化学株式会社 Thiophene derivative

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4187232A (en) * 1975-06-05 1980-02-05 Lilly Industries Limited Acylamino derivatives
AT382870B (en) * 1982-02-09 1987-04-27 Sandoz Ag Process for the preparation of novel chloroacetamides
EP0273602A1 (en) * 1986-12-05 1988-07-06 Eli Lilly And Company 3-Cyano-4-arylthiophenes
US5158598A (en) * 1988-08-04 1992-10-27 Basf Aktiengesellschaft Bithienyl derivatives, and herbicidal use for agents containing them
WO2010126167A1 (en) * 2009-04-30 2010-11-04 住友化学株式会社 Thiophene derivative
EP2426117A1 (en) * 2009-04-30 2012-03-07 Sumitomo Chemical Company, Limited Thiophene derivative
CN102459221A (en) * 2009-04-30 2012-05-16 住友化学株式会社 Thiophene derivative
EP2426117A4 (en) * 2009-04-30 2012-09-19 Sumitomo Chemical Co Thiophene derivative

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees