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 edit

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 edit

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 edit

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 edit

^ "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