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)
|
|
ECHA InfoCard | 100.106.958 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 [1] |
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 [2] and Ultor. [3]
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.
Bayer obtained spirotetramat's first regulatory approval in Tunisia in 2007. [5] [6] It was recognized by the European Union May 1, 2014. [7]
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]
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)
|
|
ECHA InfoCard | 100.106.958 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 [1] |
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 [2] and Ultor. [3]
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.
Bayer obtained spirotetramat's first regulatory approval in Tunisia in 2007. [5] [6] It was recognized by the European Union May 1, 2014. [7]
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]