Dimethipine

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Structural formula
Structural formula of dimethipine
General
Surname Dimethipine
other names
  • 2,3-dihydro-5,6-dimethyl-1,4-dithiyne-1,1,4,4-tetraoxide
  • Harvade
  • Defanet
Molecular formula C 6 H 10 O 4 S 2
Brief description

white, crystalline solid

External identifiers / databases
CAS number 55290-64-7
EC number 259-572-7
ECHA InfoCard 100.054.138
PubChem 41385
Wikidata Q3028191
properties
Molar mass 210.28 g mol −1
Physical state

firmly

density

1.59 g cm −3

Melting point

167-169 ° C

Vapor pressure

0.051 mPa (25 ° C)

solubility
  • easily soluble in acetone (122 g l −1 at 20 ° C)
  • slightly soluble in methanol (10 g l −1 at 20 ° C)
  • sparingly soluble in water (4.6 g l −1 at 25 ° C) and xylene (3.6 g l −1 at 20 ° C)
  • practically insoluble in heptane (0.02 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimethipine is a chemical compound from the group of sulfones and dithiines . It is used as a defoliant in cotton , grapevines and rubber trees , and as a growth regulator that reduces the seed moisture in rice , rapeseed , flax and sunflower . By destroying the epidermal cells, dimethipine leads to increased perspiration and a decrease in the turgor in the leaves.

Extraction and presentation

Dimethinpin can be obtained by oxidizing 2,3-dimethyl-5,6-dihydro-1,4-dithiin with hydrogen peroxide . This can in turn be obtained by reacting 1,2-ethanedithiol or 1,1-ethanedithiol with 3-chlorobutan-2-one or 3-hydroxy-2-butanone in the presence of p -toluenesulfonic acid:

Dimethipin Synthesis V1.png

Admission

In 2007 the EU Commission decided not to include dimethidine in the list of permitted active ingredients in pesticides. No pesticides containing this active ingredient are currently approved in Germany, Austria or Switzerland. In the United States, dimethipine is approved as a growth regulator and defoliant for cotton and as a selective herbicide for cotton and non-bearing apple trees .

Individual evidence

  1. ↑ a b c d e f Entry on dimethipine in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on September 4, 2013.
  2. ↑ a b c d e p D. Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects (DOSE): Volume 03 D . Royal Society of Chemistry, 1999, ISBN 0-85404-818-9 , pp. 517 .
  3. ↑ a b Datasheet Dimethipin, analytical standard from Sigma-Aldrich , accessed on September 2, 2013 ( PDF ).
  4. ^ Bahadir, Parlar, Spiteller: Springer Umweltlexikon . Springer, 2000, ISBN 3-540-23480-2 , pp. 322 ( limited preview in Google Book search).
  5. ↑ James D. Metzger, Jenpeng Keng: Cellular basis for dimethipine-induced loss of leaf turgor and desiccation . In: Journal of Plant Growth Regulation . tape 6 , no. 1 , 1987, pp. 33-40 , doi : 10.1007 / BF02025373 .
  6. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 732 ( limited preview in Google Book search).
  7. ↑ Patent US3997323 : Herbicidal method employing substituted dithin tetroxides. Registered on March 26, 1981 , published March 9, 1982 , Applicant: Uniroyal Inc., Inventors: Arthur D. Brewer, William S. McIntire, Robert W. Neidermyer. ‌
  8. ↑ Patent US4319033 : Method of making certain 2,3-dihydro-1,4-dithiins. Applied on May 12, 1975 , published December 14, 1976 , Applicant: Uniroyal Ltd., Inventor: Arthur D. Brewer, Duncan D. Lennox, Allan KS Tsai. ‌
  9. ↑ Glen A. Russell, WC Law, Mary Zaleta: Aliphatic semidiones. 44. Spin probes derived from dithiols . In: Journal of the American Chemical Society . tape 107 , no. July 14 , 1985, p. 4175-4182 , doi : 10.1021 / ja00300a016 .
  10. ↑ Decision of the Commission of August 2, 2007 (PDF) on the non-inclusion of monocarbamide dihydrogen sulfate and dimethipine in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (2007/553 / EC).
  11. ↑ General Directorate Health and Food Safety of the European Commission: Entry on dimethipine in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.
  12. ↑ United States Environmental Protection Agency (Ed.): Reregristration Eligibility Decision For Dimethipin . August 16, 2005 ( epa.gov [PDF; 711 kB ; accessed on September 4, 2013]).