Spinetoram

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Spinetoram is an insecticide of the Spinosyne group , which is obtained from fermentation products of the actinomycete Saccharopolyspora spinosa . It consists of Spinetoram-J and Spinetoram-L. The active ingredient was launched in 2007 by Dow AgroSciences .

Properties and composition

Spinetoram is a mixture of Spinetoram-L and Spinetoram-J in a ratio of approximately 1: 1 to 9: 1. The two compounds are not isomers as the Spinetoram-J contains an additional methyl group . The connections are structurally related to the spinosyns of the spinosad .

Spinetoram
Surname Spinetoram-J Spinetoram-L
other names
  • (2 R , 3a R , 5a R , 5b S , 9 S , 13 S , 14 R , 16a S , 16b R ) -2- (6-Deoxy-3- O -ethyl-2,4-di- O - methyl-α- L -mannopyranosyloxy) -13 - [(2 R , 5 S , 6 R ) -5- (dimethylamino) tetrahydro-6-methylpyran-2-yloxy] -9-ethyl-2,3,3a, 4 , 5,5a, 5b, 6,9,10,11,12,13,14,16a, 16b-hexadecahydro-14-methyl-1 H -as-indaceno [3,2- d ] oxacyclododecine-7,15- dion
  • XDE-175-J
  • (2 S , 3a R , 5a S , 5b S , 9 S , 13 S , 14 R , 16a S , 16b S ) -2- (6-Deoxy-3- O -ethyl-2,4-di- O - methyl-α- L -mannopyranosyloxy) -13 - [(2 R , 5 S , 6 R ) -5- (dimethylamino) tetrahydro-6-methylpyran-2-yloxy] -9-ethyl-2,3,3a, 5a , 5b, 6,9,10,11,12,13,14,16a, 16b-tetradecahydro-4,14-dimethyl-1 H -as-indaceno [ 3,2- d ] oxacyclododecine-7,15-dione
  • XDE-175-L
Structural formula Spinetoram-j.svg Spinetoram-l.svg
CAS number 187166-40-1 187166-15-0
935545-74-7 (mixture)
PubChem 53297414 25217966
Molecular formula C 42 H 69 NO 10 C 43 H 69 NO 10
Molar mass 748.011 g mol −1 760.022 g mol −1
Physical state firmly
Brief description White dust white-yellow crystals
Melting point 143.4  ° C 70.8 ° C
boiling point decomposes at 297.8  ° C decomposes at 290.7 ° C
solubility
  • 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
labeling
08 - Dangerous to health 09 - Dangerous for the environment 07 - Warning
Caution
H-phrases 317-373-410
EUH phrases no EUH phrases
P-phrases 260-273-280-321-333 + 313-501
Tox data

Extraction and presentation

In the early 1980s, the actinomycete Saccharopolyspora spinosa was discovered in soil samples . These microorganisms have been found to form fermentation products that are toxicologically effective against Lepidoptera . The isolated active ingredients were then examined for their activity as insecticides, with Spinosyn A and Spinosyn D being identified as the most potent representatives of these substances. The naturally occurring mixture of these two spinosyns was called spinosad .

In the search for even stronger spinosyns, an artificial neural network coupled with the analysis of the quantitative structure-activity relationship was used, which greatly reduced the time and material expenditure. The researchers discovered that spinosyn A analog with a tri- Ο -methyl- L - rhamnose residue has a potentially better effect. Further investigations showed that the 3'- O -ethyl group on rhamnose is responsible for the strongest effect on the nicotinic acetylcholine receptor in insects. Other studies have shown that the hydrogenation of the 5,6 double bond makes the molecule less sensitive to light. The combination of both findings produced the Spinetoram-J.

Mode of action

The effect of the Spinetoram is analogous to that of the Spinosad. Unlike other insecticides, spinosyne act on the nicotinic acetylcholine receptor , which activates it allosterically . This distinguishes them in their mode of action from the neonicotinoids , whose function is based on the action as an agonist of this receptor. This disrupts the nerve functions , resulting in paralysis , respiratory failure and ultimately death . It is a relatively new mode of action of pesticides, so resistance is still very rare. In addition, the compounds act on GABA receptors, which has a similar effect.

toxicology

human

The European Food Safety Authority specifies a permitted daily dose (ADI value) of 0.025 mg / kg body weight and an acute reference dose (ARfD) of 0.1 mg / kg body weight for Spinetoram . The compound is not acutely toxic to mammals and is neither skin nor eye irritant.

Ecotoxicology

Spinetoram is not very toxic to birds and fish . For bees , it is highly toxic with an LD 50 of 0.039 ug / bee. However, field studies have shown that there are no negative effects on bees if the active ingredient is applied seven days before the bees fly. An increased mortality of the bees was only found when the insecticide was sprayed during flowering and bee flight.

proof

The reliable detection and quantification of Spinetoram can be carried out using liquid chromatographic methods. A mass spectrometer can be used for identification after the chromatographic separation .

Admission

Spinetoram is approved in the European Union until June 30, 2024. In some EU countries, plant protection products with the active ingredient spinetoram are approved, but not in Germany and Austria. In contrast to the Spinosad, Spinetoram may not be used in organic farming . In Switzerland, a preparation with Spinetoram called Zorro is available, which can be used against pests of pome fruit .

Trade names

  • Dow radians
  • Dow delegate
  • Sumitomo DIANA
  • Rallis Summit

Individual evidence

  1. ↑ a b Pesticide Fact Sheet - Spinetoram. (PDF) United States Environmental Protection Agency EPA, October 2009, accessed May 30, 2018 .
  2. ↑ a b c d e f g h i Conclusion on the peer review of the pesticide risk assessment of the active substance spinetoram . In: EFSA Journal . tape 11 , no. 5 , May 2013, ISSN  1831-4732 , p. 3220 , doi : 10.2903 / j.efsa.2013.3220 ( europa.eu [PDF; accessed on May 30, 2018]).
  3. ↑ Safety data sheet Spinetoram. (PDF) In: LGC Standards. July 6, 2017, accessed June 5, 2018 .
  4. ↑ James Dripps, Brian Olson, Thomas Sparks, Gary Crouse: Spinetoram: How Artificial Intelligence Combined Natural Fermentation with Synthetic Chemistry to Produce a New Spinosyn Insecticide. Retrieved June 5, 2018 .
  5. ^ Development of the Novel Insecticide Spinetoram (DIANA®). (PDF) In: www.sumitomo-chem.co.jp. Sumitomo Chemical Co., Ltd., 2012, accessed June 1, 2018 .
  6. ^ Mark J. Miles et al .: Effects of spinosad on honey bees ( Apis mellifera ): Findings from over ten years of testing and commercial use . In: Julius Kühn Archive (Ed.): No. 437 (2012): Hazards of pesticides to bees - 11th International Symposium of the ICP-BR Bee Protection Group . October 2, 2012, ISSN  2199-921X , p. 107–114 , doi : 10.5073 / jka.2012.437.032 ( openagrar.de [accessed June 1, 2018]).
  7. ↑ Farag Mahmoud Malhat: Simultaneous Determination of Spinetoram Residues in Tomato by High Performance Liquid Chromatography Combined with QuEChERS Method . In: Bulletin of Environmental Contamination and Toxicology . tape 90 , no. 2 , November 15, 2012, ISSN  0007-4861 , p. 222–226 , doi : 10.1007 / s00128-012-0885-3 ( springer.com [accessed June 1, 2018]).
  8. ↑ Implementing Regulation (EU) No. 540/2011 of the Commission of May 25, 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances , accessed on June 4, 2018
  9. ↑ Regulation (EC) No. 889/2008 of the Commission of September 5, 2008 with implementing provisions for Regulation (EC) No. 834/2007 of the Council on organic production and the labeling of organic products with regard to organic Production, labeling and control .
  10. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Spinetoram in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on June 1, 2018.