Spirotetramat

Spirotetramat
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
CAS Number	203313-25-1;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.106.958
EC Number	606-523-6;
PubChem CID	9969573;
UNII	4G7KR034OX;
CompTox Dashboard (EPA)	DTXSID7044342 ;
	InChI 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;
	SMILES CCOC(=O)OC1=C(C(=O)NC12CCC(CC2)OC)C3=C(C=CC(=C3)C)C;
Properties
Chemical formula	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)
Solubility in water	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:
Signal word	Warning
Hazard statements	H317, H319, H335, H361, H410
Precautionary statements	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). Infobox references

Spirotetramat (ISO Name) is a keto-enol insecticide developed by Bayer CropScience under the brand names Movento^[2] and Ultor.^[3]

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. It is a systemic insecticide that penetrates plant leaves when sprayed on. It is ambimobile, being transported both upwards and downwards through vascular bundles.^[4] 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.^[5]^[6] It was recognized by the European Union May 1, 2014.^[7]

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.^[8] In Denmark, it is listed as harmful to aquatic invertebrates, but not dangerous to bees.^[9]

References

^ "Biological Buffers". Sigma-Aldrich.
^ "Movento". Crop Science.
^ "US EPA, Pesticide Produce Label, ULTOR, 05/06/2011" (PDF). EPA.
^ 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.
^ 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.
^ Agropages: New insecticide spirotetramat granted first regulatory approval." (15 November 2007)
^ COMMISSION IMPLEMENTING REGULATION (EU) No 1177/2013. (23 January 2018)
^ "EPA Pesticide Fact Sheet, juni 2008" (PDF).
^ "Merit Gran - Produktoplysninger - Middeldatabasen". middeldatabasen.dk.

[1] "Biological Buffers". Sigma-Aldrich.

[2] "Movento". Crop Science.

[3] "US EPA, Pesticide Produce Label, ULTOR, 05/06/2011" (PDF). EPA.

[4] 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.

[5] 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.

[6] Agropages: New insecticide spirotetramat granted first regulatory approval." (15 November 2007)

[7] COMMISSION IMPLEMENTING REGULATION (EU) No 1177/2013. (23 January 2018)

[8] "EPA Pesticide Fact Sheet, juni 2008" (PDF).

[9] "Merit Gran - Produktoplysninger - Middeldatabasen". middeldatabasen.dk.

[2]

[3]

[1]

[4]

[5]

[6]

[7]

[8]

[9]

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
CAS Number	203313-25-1
3D model (JSmol)	Interactive image
ECHA InfoCard	100.106.958
EC Number	606-523-6
PubChem CID	9969573
UNII	4G7KR034OX
CompTox Dashboard (EPA)	DTXSID7044342
InChI 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
SMILES CCOC(=O)OC1=C(C(=O)NC12CCC(CC2)OC)C3=C(C=CC(=C3)C)C
Properties
Chemical formula	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)
Solubility in water	Practically insoluble (0.03 g/L at 20 °C and pH 7)
Solubility in dichloromethane	Easily soluble
Acidity (pK_a)	6.9^[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Irritant
GHS labelling:
Signal word	Warning
Hazard statements	H317, H319, H335, H361, H410
Precautionary statements	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). Infobox references