Trimethacarb

Trimethacarb is a synthetic insecticide from the active ingredient group of carbamates . It was introduced by Shell Development Co. and later marketed by Union Carbide and then by Bayer AG . Today trimethacarb is no longer made and sold.

Properties and composition

Trimethacarb is a mixture of the isomers 2,3,5-trimethacarb and 3,4,5-trimethacarb in a ratio of approximately 1: 3.5 to 1: 5.

Trimethacarb
Surname	2,3,5-trimethacarb	3,4,5-trimethacarb
other names	2,3,5-trimethylphenyl methyl carbamate	3,4,5-trimethylphenyl methyl carbamate
	Landrin Broot
Structural formula
CAS number	2655-15-4	2686-99-9
	12407-86-2 (mixture)
EC number	684-207-7	220-245-9
	602-974-8 (mixture)
ECHA info card	100.209.672	100.018.405
	100.122.160 (mixture)
PubChem	53297414	25217966
Wikidata	Q27118022	Q27118023
Molecular formula	C 11 H 15 NO 2
Molar mass	193.24 g mol −1
Physical state	firmly
Brief description	yellow-brown to brown granules
Melting point	105-114 ° C
solubility	practically insoluble in water (0.010 g l −1 at 20 ° C) Easily soluble in acetone , methanol , xylene , ethyl acetate (each> 250 g l −1 at 20 ° C)	practically insoluble in water (0.032 g l −1 at 20 ° C) Easily soluble in acetone, methanol, xylene, ethyl acetate (each> 250 g l −1 at 20 ° C)
GHS marking	danger	Caution
H-phrases	225-304-315-336-410	315-317-319
EUH phrases	no EUH phrases
P-phrases	210-273-301 + 310-331-391-403 + 235	280-305 + 351 + 338

Extraction and presentation

Trimethacarb can be obtained by reacting a mixture of 2,3,5-trimethylphenol and 3,4,5-trimethylphenol with methyl isocyanate .

Mode of action

Trimethacarb acts as a repellent as well as contact and food poison with long-lasting effects. It works like other carbamate insecticides: the enzyme acetylcholine esterase in the synapses of the nervous system is inhibited. This causes an excess of acetylcholine on the postsynaptic membrane, which results in permanent excitation of the nervous system. The nerve function comes to a standstill and the affected organism is paralyzed, which can lead to respiratory failure and death.

use

Trimethacarb is an insecticide with a broad spectrum of activity. It is mainly used to combat the larvae of the corn rootworm in maize cultivation, but can also be used against other insects and mollusks . It also acts as a repellent for birds and mammals.

toxicity

Trimethacarb is non-carcinogenic and non-irritating to the skin. It is classified as not dangerous for humans. It is highly toxic to crustaceans and moderately toxic to bees , birds , fish and mammals (LD ₅₀ rat (oral) 130 mg / kg).

The compound is not persistent in soil with a half-life of 20 days.

Admission

No pesticides containing the active ingredient trimethacarb are permitted in the European Union .

Individual evidence

1. ↑ ^{a b c d} MacBean, C. (Colin), British Crop Protection Council .: The pesticide manual: a world compendium. Sixteenth ed. Alton, Hampshire 2012, ISBN 978-1-901396-86-7 , pp. 543 f.02-19 .
2. ↑ ^{a b c} Entry on Trimethacarb in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 12, 2018.
3. ↑ Safety data sheet 2,3,5-trimethacarb. (PDF) In: HPC Standards GmbH. November 13, 2017. Retrieved July 12, 2018 . 
4. ↑ Safety data sheet 3,4,5-trimethacarb. (PDF) In: HPC Standards GmbH. November 13, 2017. Retrieved July 12, 2018 . 
5. ↑ Thomas A. Unger: Pesticide synthesis handbook . Noyes Publications, 1996, ISBN 0-8155-1401-8 , pp. 97 ( limited preview in Google Book search).
6. ↑ Kalyani Paranjape: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 , pp. 489 ( limited preview in Google Book search).
7. ↑ Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls, Jack R. Plimmer: Metabolic Pathways of Agrochemicals . Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 68 ( limited preview in Google Book search).
8. ↑ Wayland J. Hayes, Edward R. Laws: Handbook of pesticide toxicology . tape 3 : Classes of pesticides . San Diego, California 1991, ISBN 0-12-334162-0 , pp. 1176 ( limited preview in Google Book search).
9. ^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on May 26, 2018.