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Synthese neuer 4-Hydroxybenzonitrilderivate und deren herbizide Eigenschaften

Synthesis of new 4-hydroxybenzonitrile derivatives and their herbicidal properties

  • Organische Chemie Und Biochemie
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Abstract

The synthesis of several new derivatives of 2-amino-4-hydroxybenzonitrile2 and their herbicidal screening data are described. Thus, halogenation and furtherSandmeyer-Reaction of2 leads to the 2,3,5-trihalogenated derivatives5 a–e. Reaction of ethyl chloroformate with the amino group of2 gives6 a, acylation7 a, b and8. The 3,5-dihalogenated compounds10 a–e are obtained from6 a and7 a, b by bromination or iodation. The hydroxyl group of6 a, 7 a, b and10 a, c, e reacts with N,N-disubstituted carbamyl chlorides to give6 c, d, 9 a, b, 11, 12 and13 a, b.

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Literatur

  1. Heywood B (1966) Chem and Ind 2: 1946

    Google Scholar 

  2. May & Baker Ltd (1964) French Patent 1375311; Ray & Baker Ltd (1965) C.A. 62: 3982 g

  3. Wegler R (1977) Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel, vol 5. Springer, Berlin Heidelberg New York, S 70

    Google Scholar 

  4. The pesticide manual (1983) 7th edn. The British Crop Protection Council, pp 166, 430

  5. Boroschewski G,Arndt F,Rusch R (1965) DOS 1 567 151;Boroschewski G,Arndt F,Rusch R (1966) Niederl Anm 6 604 363;Boroschewski G,Arndt F,Rusch R (1967) CA 66: 104813 w

  6. siehe Lit 3, p 424;

  7. Wegler R (1982) Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel, vol 8. Springer, Berlin Heidelberg New York, pp 58, 170

    Google Scholar 

  8. Schmidt HW (1985) Synthesis 1985: 778

    Google Scholar 

  9. Schmidt HW, Junek H (1979) Liebigs Ann Chem 1979: 2005

    Google Scholar 

  10. Arndt F, Boroschewski G (1977) DOS 2 608 473;Arndt F, Boroschewski G (1977) CA 87: 201134s

  11. FMC Corp (1967) Niederl Anm 6 614 472; FMC Corp (1968) CA 68: 77962 b

  12. Stauffer Chemical Co (1967) Niederl Anm 6 612 360; Stauffer Chemical Co (1968) CA 68: 29438 p

  13. Raiford LC, Alexander K (1940) J Org Chem 5: 306

    Google Scholar 

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  1. Institut für Organische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Austria

    Hans-Werner Schmidt

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  1. Hans-Werner Schmidt
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Schmidt, HW. Synthese neuer 4-Hydroxybenzonitrilderivate und deren herbizide Eigenschaften. Monatsh Chem 118, 217–228 (1987). https://doi.org/10.1007/BF00810055

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  • DOI: https://doi.org/10.1007/BF00810055

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