Spirodiclofen Chemical Properties

Melting point:

101-108°

Boiling point:

550.2±50.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

vapor pressure 

0-0Pa at 20-25℃

Flash point:

4 °C

storage temp. 

0-6°C

solubility 

Chloroform (Slightly), DMSO, Methanol (Sparingly)

form 

Solid

color 

White to Off-White

Major Application

agriculture
environmental

InChI

1S/C21H24Cl2O4/c1-4-20(2,3)19(25)26-17-16(14-9-8-13(22)12-15(14)23)18(24)27-21(17)10-6-5-7-11-21/h8-9,12H,4-7,10-11H2,1-3H3

InChIKey

DTDSAWVUFPGDMX-UHFFFAOYSA-N

SMILES

CCC(C)(C)C(=O)OC1=C(C(=O)OC12CCCCC2)c3ccc(Cl)cc3Cl

LogP

5.83 at 20℃ and pH4

EPA Substance Registry System

Spirodiclofen (148477-71-8)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

43-67-65-63-48/20-38-11

Safety Statements 

36/37-62

RIDADR 

UN1294 3/PG 2

WGK Germany 

2

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Aquatic Chronic 1
Carc. 1B
Repr. 2
Skin Sens. 1B
STOT RE 2

Hazardous Substances Data

148477-71-8(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): >2500 orally; >2000 dermally (24 hr); LC50 (4 hr) in rats (mg/m3): >5000 by inhalation; LC50 (96 hr) in fish: >68 mg/l (Wachendorff)

Spirodiclofen Usage And Synthesis

Description

Spirodiclofen is a new selective, non systemic acaricide belonging to the chemical group of the spirocyclic tetronic acid derivatives. It acts by interfering with mite development, thereby controlling such pests as Panonychus spp., Phyllocoptruta spp., Brevipalpus spp., and Aculus and Tetranychus species. Spirodiclofen is active by contact to mite eggs, all nymphal stages, and adult females (adult males are not effected). Spirodiclofen is structurally similar to spiromesifen, which is also a tetronic acid insecticide. Spirodiclofen is registered worldwide for use on a variety of crops including citrus, pome fruits, stone fruits, grapes and ornamentals.

Uses

Spirodiclofen is a tetronic acid acaricide fungicide used in controlling red mites. Spirodiclofen is used in cannabis testing kits as a component of pesticide mixes (P698240).

Definition

ChEBI: Spirodiclofen is an organochlorine acaricide, a dichlorobenzene, an oxaspiro compound and a gamma-lactone. It derives from a 1,3-dichlorobenzene.

Synthesis

Spirodiclofen is commercially produced via a multi-step synthesis starting with the condensation of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum’s acid) with 3-(2,4-dichlorophenyl)propanoyl chloride under basic conditions to form an intermediate enol ester, which undergoes thermal cyclisation in the presence of 1,1,1-trichloroethane or similar solvent to yield the spirocyclic core; subsequent esterification with 2,2-dimethylbutyryl chloride and purification give the active compound.

Mode of action

Spirodiclofen is a progenitor of tetronic acid derivates (inhibitors of acetyl CoA carboxylase), characterized by an original (unique) mechanism of action which combines long-lasting protection with anthocorid safety for effective integrated pest management.
It interferes/inhibits the lipid biosynthesis of Mites, Mealybugs and Pear-psylla.

Spirodiclofen(148477-71-8)Related Product Information

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