Chemical Identification
Common Name
Cyclanilide
中文通用名
环丙酸酰胺
IUPAC
1-(2,4-dichloroanilinocarbonyl)cyclopropanecarboxylic acid
CAS
1-[[(2,4-dichlorophenyl)amino]carbonyl]cyclopropanecarboxylic acid
CAS No.
113136-77-9
Molecular Formula
C11H9Cl2NO3
Molecular Structure
Category
Activity
Plant growth regulator.
Cyclanilide, in mixtures with ethephon, can be used to defoliate cotton, to open mature unopened cotton bolls and to reduce regrowth prior to harvesting.
CropUse
Crop uses:
cotton, rubber 

Cyclanilide will only be commercialised in combination products.
Premix

Product

Type

AI concn

Cyclanilide will only be commercialised in combination products

Suspension concentrate. Premix Parters: carbendazim triadimenol; chlorpyrifos; imidacloprid; pheromone; piperonyl butoxide propoxur tetramethrin; tebupirimfos.
Physical Properties
Molecular weight:274.1; Physical form:White powdery solid. Density:1.47 (20 °C); Melting point:195.5 °C; Vapour pressure:<0.01 mPa (25 °C); 8×10-3 mPa (50 °C); Henry constant:7.41×10-5 Pa m3 mol-1; Partition coefficient(n-octanol and water):logP = 3.25; pKa:3.5 (22 °C); Solubility:Low solubility in water. Soluble in organic solvents.; Stability:Relatively stable to photolysis. Stable to hydrolysis. Decomposes at c. 210 °C. Soluble in organic solvents.
Toxicology
Oral:Acute oral LD50 for female rats 208 mg/kg, male rats 315 mg/kg. Percutaneous:Acute percutaneous LD50 for rabbits >2000 mg/kg. Slight skin irritant. Inhalation:LC50 (4 h) for rats >5.15 mg/l. 
Environmental Profile
Ecotoxicology: 
Algae:Moderately toxic.Bees:LD50 (contact) for bees >100 μg/bee.Birds:Acute oral LD50 for bobwhite quail 216 mg/kg, mallard ducks >215 mg/kg b.w. Dietary LC50 (8 d) for bobwhite quail 2849, mallard ducks 1240 ppm. Daphnia:EC50 (48 h) >13 mg/l.Fish:LC50 (96 h) for bluegill sunfish >16 mg/l, rainbow trout >11 mg/l, sheepshead minnow 49 mg/l.Worms:Moderately toxic. Environmental fate: 
Animals:Rapidly excreted, primarily as unchanged cyclanilide.Soil:Low to moderate persistence, DT50 c. 16 d under aerobic conditions. Degrades primarily by microbial activity. Medium to low mobility (average Koc 346). Consequently little potential for leachPlant:Little degradation occurs in plants; cyclanilide is the major residue.

Mallard duck

LD50 >215 mg/kg

Rainbow trout [96 hrs]

LC50 >11 mg/litre

Bluegill sunfish [96 hrs]

LC50 >16 mg/litre

Earthworm [14 days]

LC50 469 mg/kg

Bee [contact]

LD50 >100 μg/bee

Bee [oral]

LD50 89.5 μg/bee

Daphnia magna

EC50 13 mg/L

Alga (S carpricornutum)

EC50 (cell density) 1.7 mg/L

Fate in soil:
The DT50 for soil photolysis is 151 days at 25°C.
Cyclanilide is degraded by microbes in the soil. In aerobic soil metabolism studies, the major metabolite is 2,4-dichloroaniline (2,4-DCA) at 1.5 - 16% of the applied radioactivity.
The DT50 for laboratory aerobic soil metabolism is 15-49 days (mean = 29 days) at 20°C. The corresponding DT90 is 50-162 days (mean = 96 days).
Under laboratory anaerobic conditions, the DT50 for cyclanilide at 20°C is 15 months or more.
In field dissipation studies in France and Spain, the DT50 for cyclanilide is 11-45 days (mean = 28 days) and the DT90 was 37-151 days (mean = 94 days). In the US, the DT50 was measured at 34-114 days (mean = 65 days).
The Koc for cyclanilide ranges from 194 (loamy sand) to 565 (silty loam), with Kd ranging from 1.05 - 3.83.
Cyclanilide has low to moderate soil persistance and mobility.

Fate in aquatic systems:
Cyclanilide is primarily degraded by microbes in water.
It is not hydrolysed at pH 5,7 or 9. The product does not bioaccumulate in water.
The DT50 for aqueous photostability ranges from 997 hours (pH 5, 9) to 1173 hours (pH 7).
In water / sediment studies, the DT50 for cyclanilide is 17-18 days (water layer) and 56-63 days (whole system). After 105 days, 14-18% of the parent compound is found in the water phase and 13-15% in the soil layer.

Transport Information
Signal Word:DANGER; Hazard Class:Ib(Highly hazardous)

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