112636-83-6

Usage

Uses

Used in Veterinary Medicine:
Dicyclanil is used as a veterinary medication for the protection against early season myiasis in sheep. It acts as an insect development inhibitor, preventing blowfly strike by targeting the growth and development of insects.
Used in Analytical Chemistry:
Dicyclanil may be employed as an analytical reference standard for the quantification of the analyte in various biological samples. It is particularly useful in the analysis of bovine, porcine, and chicken muscle using different chromatography techniques, such as high-performance liquid chromatography (HPLC) or gas chromatography (GC). This application aids in the accurate measurement and monitoring of Dicyclanil residues in the meat industry, ensuring the safety and quality of animal products for human consumption.

Pharmacokinetics

Dicyclanil has a long lasting action which interferes with moulting and pupation in dipteran species. However, the precise mode of action of Dicyclanil on ectoparasites is not known. A variety of in vitro and in vivo pharmacodymanic tests were performed with dicyclanil in rats, mice and guinea pigs. In vitro, dicyclanil was devoid of significant effects on the neuromuscular junction at concentrations below 3 mM. Slight antagonistic effects on smooth muscle were reported at concentration levels above 0.1 mM. Dicyclanil caused a statistically significant increase in heart rate, tidal volume and minute volume at a dose level of 100 mg/kg bw in studies on the cardiovascular and respiratory systems in the rat. In various in vivo studies, dicyclanil was devoid of significant effects on behavior at a dose level of 1 mg/kg bw in mice.

Toxicity evaluation

Dicyclanil was investigated in a series of acute toxicity studies. The acute LD50 by the oral route in the rat was 520 mg/kg bw. The acute LD50 by the dermal route was greater than 2000 mg/kg bw in the rat. An acute inhalation toxicity study also conducted in the rat showed the acute LC50 to be 3,184 mg/m3 of air. The toxic effects were dyspnoea and reduced locomotor activity.

InChI:InChI=1/C8H10N6/c9-3-5-6(10)13-8(14-7(5)11)12-4-1-2-4/h4H,1-2H2,(H5,10,11,12,13,14)

Synthetic route

4,6-diamino-5-fluoro-2-cyclopropylaminopyrimidine + potassium ferrocyanide → 2-cyclopropylamino-4,6-diamino-5-cyanopyrimidine (112636-83-6)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 3.5h; Temperature; Large scale;	80%

4,6-diamino-2-chloro-5-cyanopyrimidine (18340-56-2) + Cyclopropylamine (765-30-0) → 2-cyclopropylamino-4,6-diamino-5-cyanopyrimidine (112636-83-6)

Conditions	Yield
With potassium hydroxide In acetonitrile for 5h; Reagent/catalyst; Solvent; Reflux;	68.7%

dimethyl N-cyanodithioiminocarbonate (10191-60-3) + Cyclopropylamine (765-30-0) + malononitrile (109-77-3) → 2-cyclopropylamino-4,6-diamino-5-cyanopyrimidine (112636-83-6)

Conditions	Yield
Stage #1: malononitrile With sodium methylate In methanol at 0 - 5℃; for 0.5h; Stage #2: dimethyl N-cyanodithioiminocarbonate In methanol at 0 - 5℃; for 12h; Stage #3: Cyclopropylamine Further stages;	80 g

2-cyclopropylamino-4,6-diamino-5-cyanopyrimidine (112636-83-6) → 2,4,6-triamino-pyrimidine-5-carbonitrile + 3-amino-N-(4,6-diamino-pyrimidine-5-carbonitrile)-acetamide + 3-amino-N-(4,6-diamino-pyrimidine-5-carbonitrile)-3-ol-propionaldehyde

Conditions	Yield
With water pH=6.2; Product distribution; Further Variations:; Reagents; var. time; UV-irradiation;

Upstream product

• 18340-56-2 4,6-diamino-2-chloro-5-cyanopyrimidine 
• 765-30-0 Cyclopropylamine 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 
• 109-77-3 malononitrile 

Related news

Wohlfahrtiosis in sheep and the role of Dicyclanil (cas 112636-83-6) in its prevention07/23/2019

Wohlfahrtia magnifica is the main agent of traumatic myiasis in the southern Palaearctic zone. It was recorded in outbreak situations in Crete, Greece, for the first time in 1999, causing widespread production losses and considerable concern in the livestock sectors. Most commonly applied curati...detailed

Relevant academic research and scientific papers

Synthetic method of dicyclanil

The invention discloses a synthetic method of dicyclanil. The sodium dicyandiamide and malononitrile are used as initial raw materials, a crude dicyandiamide product is obtained through condensation,cyclization and amination reactions, and a refined dicyandiamide product is obtained through decoloration and refining. The synthetic route is short, the process is green and environment-friendly, andmethyl mercaptan is not generated; the method has the advantages of mild reaction conditions, no need of pressurized ammonification, low equipment requirements and simple operation, and is suitable for domestic industrial production. The total yield reaches 65% or above, and the product purity reaches 99% or above.

Dicyclanil preparation method

The invention relates to the field of insecticides, in particular to a dicyclanil preparation method. The method comprises the steps as follows: 500 g of absolute methanol and 270 g of a sodium methylate methanol solution are added to a 2 L four-neck flask, the obtained solution is cooled to 0-5 DEG C in an ice-water bath, 72.8 g of malononitrile is added, stirring is performed for 30 min, the temperature is kept at 0-5 DEG C, 146.5 g of N-cyanoimido-S, S-dimethyl-dithiocarbonate is added in batches, the obtained mixture is stirred at 0-5 DEG C to react for 12 h, filtration is performed afterthe reaction, a filter cake is washed with 100 mL of cold absolute methanol, and the filter cake is drained and directly used in the next reaction without drying; the wet product is dissolved in 860 gof water, the obtained solution is added to a four-neck flask and stirred to be dissolved, the temperature is decreased to 0-5 DEG C in an ice-water bath, 1,200 g of industrial hydrochloric acid is dropwise added for about 4-5 h, the obtained mixture is stirred at 0-5 DEG C and stays overnight after addition, filtration is performed after complete reaction, a filter cake is washed with water andwashed twice with 10% sodium carbonate, the washed filter cake is dried in a drying oven after being drained, and 157 g of a dried product is obtained. The process is simple, the reaction is safe, theproduction cost is greatly reduced, and the product purity is improved.

A preparation method of ground past Neil

The invention discloses a preparation method of dicyclanil, belongs to the field of preparation of growth regulators, and solves the problem that the existing dicyclanil production process is high in synthetic condition, great in toxicity of synthetic raw materials and low in reaction yield. The preparation method comprises the following steps: carrying out substitution reaction on guanidine hydrochloride and bromocyclopropane; carrying out closed-ring reaction on the product obtained from the former step and 2-fluoropropiondiamide; and finally substituting florine on aromatic rings by providing cyan groups from potassium ferrocyanide to obtain a dicyclanil product. The preparation method disclosed by the invention is simple in operating step, low in price of materials and high in yield, and the obtained product is high in purity and shallow in color, and dicyanomethane which is relatively great in toxicity is not used in the production process.

Active agent combinations

The novel active compound combinations of extracts from seeds of the neem tree and the active compounds of groups (B) to (F) listed in the description have very good insecticidal and acaricidal properties.