GB1357154A - Alkylthio-nitro-aniline compounds and herbicidal 'ompositions containing them - Google Patents

Alkylthio-nitro-aniline compounds and herbicidal 'ompositions containing them

Info

Publication number
GB1357154A
GB1357154A GB4444871A GB4444871A GB1357154A GB 1357154 A GB1357154 A GB 1357154A GB 4444871 A GB4444871 A GB 4444871A GB 4444871 A GB4444871 A GB 4444871A GB 1357154 A GB1357154 A GB 1357154A
Authority
GB
United Kingdom
Prior art keywords
dinitro
dialkyl
alkyl
alkylthio
carbon atoms
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
GB4444871A
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 GB1357154A publication Critical patent/GB1357154A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
    • A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1357154 Nitroaniline derivatives SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 23 Sept 1971 [25 Sept 1970 (2)] 44448/71 Heading C2C Nitroaniline derivatives of a general formula in which R is lower alkyl of 1 to 3 carbon atoms , R<SP>1</SP> and R<SP>11</SP> are each the same or different and represent alkyl of 1 to 7 carbon atoms, alkenyl of 2 to 7 carbon atoms or cycloalkyl with 3 to 7 carbon atoms with the proviso that R<SP>1</SP> and R<SP>11</SP> combined do not contain more than 8 carbon atoms, and n is zero or one are prepared when n is 0 by (a) reacting a 4-(alkylthio)phenol with a dialkyl sulphate to form a 4-hydroxyphenyl dialkyl sulphonium alkyl sulphate; (b) dinitrating the resulting 4-hydroxyphenyl dialkyl sulphonium alkyl sulphate with nitric acid in the presence of sulphuric acid to form a (3,5- dinitro - 4 - hydroxyphenyl)dialkyl sulphonium alkyl sulphate; (c) reacting the (3,5-dinitro-4- hydroxyphenyl)dialkyl sulphonium alkyl sulphate with an aqueous alkali metal halide to form a 2,6 - dinitro - 4 - (alkylthio)phenol; (d) reacting 2,6 - 6 - dinitro - 4 - (alkylthio)- phenol with a chlorinating agent selected from the group consisting of thionyl chloride, phosgene or phosphorus oxychloride in carbon tetrachloride in the presence of a catalytic amount of dimethylformamide to form a 4 - chloro - 3,5 - dinitro - phenyl alkyl sulphide; and (e) treating the 4-chloro-3,5-dinitrophenyl alkyl sulphide with a dialkyl amine to form a 4 - (alkylthio) - 2,6 - dinitro - N,N - dialkylaniline; when n is 1 the compound formed in (e) above is oxidized to form 4-(alkylsulphinyl)- 2,6 - dinitro - N,N - dialkyl - aniline. There is also described the preparation of 4-(methylsulphonyl) - 2,6 - dinitro - N,N - dipropyl aniline by oxidizing the 4-(methylthio-2,6- dinitro - N,N dipropylaniline and the 4- (methylsulphinyl) - 2,6 - dinitro - N,N - dipropyl aniline with hydrogen peroxide.
GB4444871A 1970-09-25 1971-09-23 Alkylthio-nitro-aniline compounds and herbicidal 'ompositions containing them Expired GB1357154A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7568370A 1970-09-25 1970-09-25
US7568470A 1970-09-25 1970-09-25

Publications (1)

Publication Number Publication Date
GB1357154A true GB1357154A (en) 1974-06-19

Family

ID=26757153

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4444871A Expired GB1357154A (en) 1970-09-25 1971-09-23 Alkylthio-nitro-aniline compounds and herbicidal 'ompositions containing them

Country Status (3)

Country Link
DE (1) DE2147610A1 (en)
FR (1) FR2112978A5 (en)
GB (1) GB1357154A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0026307A1 (en) * 1979-08-15 1981-04-08 Merck & Co. Inc. Organic sulfoxides, process for preparing the same and pharmaceutical enzyme inhibiting compositions comprising the same
US4388475A (en) 1979-08-15 1983-06-14 Merck & Co., Inc. Allylsulfoxide enzyme inhibitors
US4558071A (en) * 1979-08-15 1985-12-10 Merck & Co., Inc. Phenyl, trihalomethyl or heteroaryl sulfoxides having a latent allyl group bound to sulfur as enzyme inhibitors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0026307A1 (en) * 1979-08-15 1981-04-08 Merck & Co. Inc. Organic sulfoxides, process for preparing the same and pharmaceutical enzyme inhibiting compositions comprising the same
US4388475A (en) 1979-08-15 1983-06-14 Merck & Co., Inc. Allylsulfoxide enzyme inhibitors
US4558071A (en) * 1979-08-15 1985-12-10 Merck & Co., Inc. Phenyl, trihalomethyl or heteroaryl sulfoxides having a latent allyl group bound to sulfur as enzyme inhibitors

Also Published As

Publication number Publication date
DE2147610A1 (en) 1972-06-08
FR2112978A5 (en) 1972-06-23

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Legal Events

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