Cyclanilide

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Chemical Identification | General Product Information | Physical & Safety Data

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

General Product Information

Category

Plant growth regulators > Unclassified plant growth regulators

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 & Safety Data

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 K_oc 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.