Spirotetramat

Spirotetramat
Chemical structure of spirotetramat
Chemical structure of spirotetramat
Chemical structure of spirotetramat 3D
Chemical structure of spirotetramat 3D
Names
IUPAC name
cis-3-(2,5-Xylyl)-4-(ethoxycarbonyloxy)-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one
Other names
Spirotetramat, Movento, Ultor, cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.106.958 Edit this at Wikidata
EC Number
  • 606-523-6
KEGG
UNII
  • InChI=1S/C21H27NO5/c1-5-26-20(24)27-18-17(16-12-13(2)6-7-14(16)3)19(23)22-21(18)10-8-15(25-4)9-11-21/h6-7,12,15H,5,8-11H2,1-4H3,(H,22,23)
    Key: CLSVJBIHYWPGQY-UHFFFAOYSA-N
  • CCOC(=O)OC1=C(C(=O)NC12CCC(CC2)OC)C3=C(C=CC(=C3)C)C
Properties
C21H27NO5
Molar mass 373.449 g·mol−1
Density 1.23 g/cm3
Melting point 142 °C (288 °F; 415 K)
Boiling point 235 °C (455 °F; 508 K) (decomposes)
Practically insoluble (0.03 g/L at 20 °C and pH 7)
Solubility in dichloromethane Easily soluble
Acidity (pKa) 6.9
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
GHS labelling:
Warning
H317, H319, H335, H361, H410
P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P333+P313, P337+P313, P363, P391, P403+P233, P405, P501
Flash point Non-flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Spirotetramat (ISO Name) is a keto-enol insecticide developed by Bayer CropScience under the brand names Movento and Ultor.

Mechanism

Spirotetramat is active against piercing-sucking insects, such as aphids, mites, and white flies, by acting as an ACC inhibitor, interrupting lipid biosynthesis in the insects, and is in IRAC group 23. It is a systemic insecticide that penetrates plant leaves when sprayed on. It is ambimobile, being transported both upwards and downwards through vascular bundles. In plants, it is hydrolyzed to the enol form by cleavage of the central ethoxycarbonyl group. This enol is more stable due to double bond being in a ring and the conjugation with the amide group and the benzene ring.

Regulation

Bayer obtained spirotetramat's first regulatory approval in Tunisia in 2007. It was recognized by the European Union May 1, 2014.

Toxicology and safety

Spirotetramat has moderate to low acute toxicity, is irritating to eyes and potentially sensitizing to skin. When tested on rats, it was not shown to be carcinogenic. In Denmark, it is listed as harmful to aquatic invertebrates, but not dangerous to bees.

References

  1. ↑ "Biological Buffers". Sigma-Aldrich.
  2. 1 2 Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "32.4 Inhibitors of Lipid Synthesis: Acetyl-CoA Carboxylase Inhibitors.". Modern Crop Protection Compounds (3rd ed.). Wiley-VCH. pp. 1202–1222. doi:10.1002/9783527699261. ISBN 9783527699261.
  3. ↑ "Movento". Crop Science.
  4. ↑ "US EPA, Pesticide Produce Label, ULTOR, 05/06/2011" (PDF). EPA.
  5. ↑ Bruck E, et al. (Oct 2009). "Movento, an innovative ambimobile insecticide for sucking insect pest control in agriculture: Biological profile and field performance". Crop Protection. 28 (10): 838–844. doi:10.1016/j.cropro.2009.06.015.
  6. ↑ Braham M, Glida-Gnidez H, Hajji L (7 Aug 2012). "Management of the tomato borer, Tuta absoluta in Tunisia with novel insecticides and plant extracts". EPPO Bulletin. 42 (2): 291–296. doi:10.1111/epp.2572.
  7. ↑ Agropages: New insecticide spirotetramat granted first regulatory approval."[link removed] (15 November 2007)
  8. ↑ COMMISSION IMPLEMENTING REGULATION (EU) No 1177/2013. (23 January 2018)
  9. ↑ "EPA Pesticide Fact Sheet, juni 2008" (PDF).
  10. ↑ "Merit Gran - Produktoplysninger - Middeldatabasen". middeldatabasen.dk.