Cyantraniliprole

Structural formula
General
Surname	Cyantraniliprole
other names	3-Bromo-1- (3-chloro-2-pyridinyl) - N - [4-cyano-2-methyl-6- (methylcarbamoyl) phenyl] -1 H -pyrazole-5-carboxamide Cyazypyr Exirel
Molecular formula	C 19 H 14 BrClN 6 O 2
Brief description	white, powdery solid
External identifiers / databases
CAS number 736994-63-1 EC number 680-242-7 ECHA InfoCard 100.205.162 PubChem 11578610 ChemSpider 9753377 Wikidata Q17073330
properties
Molar mass	473.71 g · mol -1
Physical state	firmly
Melting point	224 ° C
boiling point	decomposes at 350 ° C
Vapor pressure	5.13 · 10 −15 Pa (25 ° C)
solubility	very sparingly soluble in water (14.2 mg l −1 at 20 ° C) sparingly soluble in acetone , ethyl acetate , toluene and methanol
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
Toxicological data	> 5.2 mg L −1 ( LC 50 ,  rat ,  inh. ) > 5000 mg kg −1 ( LD 50 ,  rat ,  oral ) > 5000 mg kg −1 ( LD 50 ,  rat ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyantraniliprole is an insecticide from the group of active ingredients called ryanodine receptor modulators.

It was introduced by the DuPont Crop Protection company in 2008.

Mode of action

Like all ryanoids, cyantraniliprole interacts with the ryanodine receptors , a type of calcium channel in muscle cells . Cyantraniliprole activates the receptor so that calcium ions are released. As a result, control over muscle functions is lost, leading to paralysis and death .

The relatively new active ingredient is an alternative to conventional phosphoric acid esters or neonicotinoids , to which some insects have already developed resistance .

Areas of application

Cyantraniliprole is both applied to the soil and sprayed directly onto the leaves of plants. It is also used for dressing seeds .

It has both an insecticidal and a repellent effect .

Studies have shown that cyantraniliprole is a suitable agent against pests such as the whitefly or the European corn borer .

toxicology

In animal experiments it was shown that cyantraniliprole has a low toxicity for humans and mammals . The European Food Safety Authority (EFSA) specifies a value for the permitted daily dose (ADI) of 0.01 mg / kg body weight. Furthermore, no genotoxic or carcinogenic effects could be proven.

Ecotoxicology

Cyantraniliprol is low toxic to birds , algae and aquatic plants , moderately toxic to fish and crustaceans as well as highly toxic to all insects and invertebrates aquatic organisms .

It is classified as highly toxic to bees. The LD ₅₀ of cyantraniliprole for honey bees ( Apis mellifera ) is 0.0934 µg · bee ⁻¹ . Bees showed increased lethargy below the lethal dose .

Cyantraniliprole is moderately persistent in the environment.

Analytics

Both liquid and gas chromatographic methods can be used for reliable detection and quantification of cyanotraniliprole . A mass spectrometer can be used for identification after the chromatographic separation .

Admission

Plant protection products with this active ingredient have been approved in Germany and some EU states since 2016 , but not in Austria or Switzerland.

In 2018 Cyantraniliprol in DuPont Exirel by emergency approval for the fight against cherry fruit and cherry vinegar fly allowed in fruit growing. This was also the case in 2017. At the end of March 2020, Benevia was approved by the Federal Office for Consumer Protection and Food Safety (BVL) through emergency approval against the asparagus fly in asparagus cultivation. Regular approval applications for pesticide mixtures with this active ingredient have also been submitted.

Trade names

• From FMC:
  • Exirel®
  • Benevia®
  • Verimark®

• Corteva Lumiposa®
• Syngenta Minecto® Pro (in combination with Abamectin )
• Syngenta Minecto® Duo 40WG (in combination with thiamethoxam )

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on cyantraniliprole in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on May 7, 2018.
2. ↑ ^{a b} Datasheet Cyantraniliprole PESTANAL, analytical standard at Sigma-Aldrich , accessed on May 9, 2018 ( PDF ).
3. ↑ ^{a b} Conclusion on the peer review of the pesticide risk assessment of the active substance cyantraniliprole . In: EFSA Journal . tape 12 , no. September 9 , 2014, doi : 10.2903 / j.efsa.2014.3814 .
4. ↑ ^{a b c d} World Health Organization (Ed.): Pesticide Residues in Food - 2013: Toxicological Evaluations . Geneva 2014, ISBN 978-92-4166529-2 , pp. 131-181 ( inchem.org [PDF]).
5. ↑ Siddharth Tiwari, Lukasz L. Stelinski: Effects of cyantraniliprole, a novel anthranilic diamide insecticide, against Asian citrus psyllid under laboratory and field conditions . In: Pest Management Science . tape 69 , no. 9 , February 2013, p. 1066-1072 , doi : 10.1002 / ps.3468 .
6. ↑ Shimat V. Joseph: Repellent Effects of Insecticides Against Protaphorura fimata (Collembola: Poduromorpha: Onychiuridae) . In: Journal of Economic Entomology . tape 111 , no. 2 , January 2018, p. 747-754 , doi : 10.1093 / jee / tox375 .
7. ↑ Rafael Caballero, David J. Schuster, Natalia A. Peres, Jozer Mangandi, Tomas Hasing: Effectiveness of Cyantraniliprole for Managing Bemisia tabaci (Hemiptera: Aleyrodidae) and Interfering with Transmission of Tomato Yellow Leaf Curl Virus on Tomato . In: Journal of Economic Entomology . tape 108 , no. 3 , June 2015, p. 894-903 , doi : 10.1093 / jee / tou034 .
8. ↑ Ran Wang, Wei Zhang, Wunan Che, Cheng Qu, Fengqi Li: Lethal and sublethal effects of cyantraniliprole, a new anthranilic diamide insecticide, on Bemisia tabaci (Hemiptera: Aleyrodidae) MED . In: Crop Protection . tape 91 , January 2017, p. 108–113 , doi : 10.1016 / j.cropro.2016.10.001 .
9. ↑ Rebecca A. Schmidt-Jeffris, Brian A. Nault: Anthranilic Diamide Insecticides Delivered via Multiple Approaches to Control Vegetable Pests: A Case Study in Snap Bean . In: Journal of Economic Entomology . tape 109 , no. 6 , December 2016, p. 2479-2488 , doi : 10.1093 / jee / tow219 .
10. ^ Environmental Fate and Effects Division, EPA, Environmental Fate and Ecological Risk Assessment for the Registration of the New Chemical Cyantraniliprole. Office of Pesticide Programs, April 13, 2013, accessed May 14, 2018 . 
11. ↑ Timo Schwarz, Timothy A. Snow, Christopher J. Santee, Christopher C. Mulligan, Thomas Class: QuEChERS Multiresidue Method Validation and Mass Spectrometric Assessment for the Novel Anthranilic Diamide Insecticides Chlorantraniliprole and Cyantraniliprole . In: Journal of Agricultural and Food Chemistry . tape 59 , no. 3 , February 2011, p. 814-821 , doi : 10.1021 / jf103468d .
12. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Cyantraniliprole in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.
13. ↑ Approvals for emergency situations. In: BVL - Federal Office for Consumer Protection and Food Safety. BVL - Federal Office for Consumer Protection and Food Safety, May 16, 2018, accessed on May 16, 2018 . 
14. ↑ BVL - Technical reports - BVL grants emergency approval for the plant protection product Benevia in asparagus. Retrieved April 1, 2020 . 
15. ↑ Christine Vogt: After a successful lawsuit: Authority provides information on insect poisons In: Umweltinstitut.org , June 25, 2018, accessed on June 27, 2018.