F0RM 2
THE PATENT ACT, 1970
(39 of 1970)
&
The Patents Rules, 2003
COMPLETE SPECIFICATION
(See section 10 and rule 13)
1. TITLE OF THE INVENTION
"AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZINE DERIVATIVE USED AS AN INSECTICIDE"
2. APPLICANT
NAME : LASA LABORATORY PVT. LTD.
NATIONALITY: INDIAN
ADDRESS : PLOT NO. C-105, MAHAD M.I.D.C.,
. INOL AREA, MAHAD, DIST- RAIGAD, PIN-402309, MAHARASHTRA, INDIA.
The following specification particularly describes the invention and the manner in which it is to be performed.

TITLE
AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZINE DERIVATIVE USED AS AN INSECTICIDE
FIELD OF THE INVENTION
Present invention relates to an improved process for the preparation of triazine derivative compound of formula I shown below, used as an insecticide.

BACKGROUND OF INVENTION
Triazine derivative compound of formula I, chemically designated as N-cyclopropyl-1,3,5-triazine-2,4,6-triamine was disclosed in US patent no. 4,225,598. It was discovered by Ciba-Giegy Ltd. and originally developed under the trade name of' VETRAZINE ' a blow-fly control agent. It is a new class of insect growth regulator used as an insecticide. In veterinary medicine triazine derivative compound of formula 1, is used as an ectoparasiticide and is added to animal feed to prevent fly from the manure. It is also applied topically to control house fly larvae in manure, so as to improve the hygiene control of animal housing environments. Further, it is used on a broad range of vegetable crops. It acts by inhibiting the molting processes, particularly in Dipteran insects.
US patent no. 4,225,598 disclosed the process for preparation of triazine derivative compound of formula I, as shown below in scheme I.


However, the aforementioned prior art process is not suitable for commercial scale as the yield obtained in only 48%. Also the cyclopropylamine addition step is carried out at -10°C which needs special chilling arrangement resulting in operational difficulties and additional cost. The U.S. Environmental Protection Agency classifies dioxane as a probable human carcinogen. This compound is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. Accidental worker exposure to 1,4-dioxane has resulted in several deaths. Also, like some other ethers, dioxane combines with atmospheric oxygen upon prolonged exposure to air to form potentially explosive peroxides. Dioxane is a hazardous solvent and not environment friendly for the preparation of triazine derivative compound of structural formula I.
An alternative method of synthesis of compound of structural formula I is disclosed in Chinese patent document CN1166648 in which cyanuric chloride is aminated in acetone solvent and then the intermediates are converted to compound of structural formula I in a base catalyzed reaction of cyclopropylamine at reflux temperature in water. However, the reaction product needs further purification to obtain 99% purity and in spite of using base catalyst the yield of the process is only 59%. Also, the reaction time for base catalyzed reaction step is seven hours. Due to these short comings this process is not preferable at commercial scale.

Accordingly there is need to develop a process for the preparation of triazine derivative compound of structural formula I, which overcomes the prior art problems.
Present inventions provide a process for preparation of compound of structural formula I in which the product is obtained with significantly high yield and with superior quality. It is safe and cost effective. The process time is faster and more than 99.00% purity is achieved without extra purification.
SUMMARY OF THE INVENTION
The invention provides a process for preparing N-cyclopropyl-l,3,5-triazine-2,4,6-triamine comprising amination of 2,4,6-trichloro-l,3,5-triazine to obtain aminated intermediates and reacting obtained aminated intermediates with cyclopropylamine in presence of activated carbon to get N-cycIopropyI-l,3,5-triazine-2,4,6-triamine.
More preferably, the invention "provides a process for preparation of N-cyclopropyl-1,3,5-triazine-2,4,6-triamine comprising aminating 2,4,6-trichloro-l,3,5-triazine with aqueous ammonia to obtain aminated intermediates and reacting obtained aminated intermediates with cyclopropylamine in presence of activated carbon in water within the temperature range of 100°C to 110°C to get N-cyclopropyl-l,3,5-triazine-2,4,6-triamine.
BRIEF DESCRIPTION OF THE DRAWINGS
For more complete understanding of the features and advantages of the present invention, . reference is now made to the detailed description of the invention along with the accompanying figure and in which:
Figure I depicts IR of N-cyclopropyl-l,3,5-triazine-2,4,6-triamine
Figure II depicts HPLC Chromatogram of N-cyclopropyl-1, 3,5-triazine-2,4,6-triamine

DETAILED DESCRIPTION OF INVENTION
The discussion of documents, acts, materials, devices, articles and the like is included in this specification solely for the purpose of providing a context for the present invention. It is not suggested or represented that any or all of these matters formed part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date of each claim of this application.
In first aspect, invention provides a process for preparing N-cyclopropyl-l,3,5-triazine-2,4,6-triamine comprising amination of 2,4,6-trichloro-l,3,5-triazine to obtain aminated intermediates . and reacting obtained aminated intermediates with cyclopropylamine in presence of activated carbon to get N-cyclopropyl-1,3,5-triazine-2,4,6-triamine.
According to first embodiment of the inventive process, the amination of 2,4,6-trichIoro-l,3,5-triazine is done by treating 2,4,6-trichloro-l,3,5-triazine with an aminating agent. While any suitable aminating agent can be employed in this step, preferably aminating agents are selected from the group consisting of ammonia gas, aqueous ammonia solution, alcoholic ammonia and any combination thereof. Solvent/s may be employed as per suitability with 2,4,6-trichloro-l,3,5-triazine and aminating agent. Preferably suitable solvent/s for this reaction includes but not limited to water, hydrocarbons, halogenated hydrocarbons, alcohols and mixtures thereof.
According to second embodiment of the inventive process, these obtained aminated intermediates are reacted with cyclopropylamine in presence of activated carbon. Preferably suitable solvent(s) for this reaction includes but not limited to water, hydrocarbons, halogenated hydrocarbons, alcohols and mixtures thereof. Preferably reaction is carried out at temperature range of 100°C to 110°C with water. Preferably, 1% to 3% activated carbon with respect to aminated intermediates is employed in this reaction. Activated .carbon has uniform porosity and high surface area. More preferably activated carbons having methylene blue adsorption value at least 5g/100g or more are suitable for this reaction. Commercially available activated carbons include Norit® carbon series from Cabot Corporation. The rate of this reaction step is faster and

the product is obtained around within 4 hours. The loss of cyclopropylamine is prevented as it is entrapped within and adsorbed on the activated carbon, thus process becomes more efficient.
The reaction mass is then filtered and the pH of the filtrate may be made basic to precipitate the product.
This process gives high' yield product with superior quality. It gives more than 76% yield with HPLC purity of at least 99.00%. Cyclopropylamine is made available for reaction at elevated temperatures and thus optimum utilization of cyclopropylamine makes the process cost efficient.
EXAMPLES:
The present invention is further described with the help of the following examples, which are given by way of illustration and should not be construed to limit the scope of the invention in any manner.
Example 1: Preparation of aminated intermediate
In clean reactor liquor ammonia (0.0083 mmoles) charged, cooled to 30°C. Then slowly added 2,4,6-trichloro-l,3,5-triazine (0.0018 mmoles). Temperature was maintained at temperature below 30°C for 6 hours. After adding purified water (700 liters) the reaction mass was filtered and unloaded the wet cake. Yield: 99%
Example 2: N-cyclopropyl-l,3,5-triazine-2,4,6-triamine
Purified water (5.5 liters), obtained material of example 1 i.e. 6-chloro-l,3,5-triazine-2,4-diamine (0.0068 moles), cyclopropyl amine (0.0072 moles) and activated carbon (2%) was added in a clean reactor. Reaction mass was heated and maintained up to temperature of 105°C for 4 hours. Cooled to 100°C and filtered thorough hot sparkler filter with hyflow bed. Cooled to room temperature and pH was adjusted to 6.5 to 7.0 with 20 to 25%) ammonia solution. Finally,

reaction mass filtered, unloaded and dried at below 80°C to get N-cyclopropyl-l,3,5-triazine-
2,4,6-triamine.
Yield: 77%
Melting Point: 219°C to 222°C
Purity: 99.98% (By HPLC)
IR: As depicted in Figure I.
HPLC Chrpmatogram: As depicted in Figure II.

WE CLAIM,
1. A process for preparation of N-cyclopropy!-l,3,5-triazine-2,4,6-triamine comprising
amination of 2,4,6-trichIoro-l,3,5-triazine to obtain animated intermediates and reacting obtained
aminated intermediates with cyclopropylamine in presence of activated carbon to get N-
cyc!opropyl-l,3,5-triazine-2,4,6-triamine.
2. The process of claim 1, wherein the amination of 2,4,6-trichloro-l,3,5-triazine is done by treating 2,4,6-trichloro-l,3,5-triazine with an aminating agent.
3. The process of claim 2, wherein the aminating agent is selected from the group consisting of ammonia gas, aqueous ammonia solution, alcoholic ammonia and any combination thereof.
4. The process of claim 1, wherein amination of 2,4J6-trichloro-l,3,5-triazine is done by treating 2;4,6-trichloro-l?3,5-triazine with aqueous ammonia solution.

5. The process of claim 1, wherein reaction of obtained aminated intermediates with cyclopropylamine in presence of activated carbon is carried out in at least one of solvent selected from water, hydrocarbons, halogenated hydrocarbons, alcohols or mixtures thereof.
6. The process of claim 1, wherein reaction of obtained aminated intermediates with cyclopropylamine in presence of activated carbon is carried out in water.
7. The process of claim 6, wherein reaction of obtained aminated intermediates with cyclopropylamine in presence of activated carbon is carried out in water at temperature range of 100°C to 110°C.
8. The process of claim 7, wherein activated carbon is present in an amount of 1% to 3% of
aminated intermediates.

9. A process for preparation of N-cyclopropyl-l,3,5-triazine-2,4,6-triamine comprising aminating 2,4,6-trichloro-l,3,5-triazine with aqueous ammonia to obtain aminated intermediates and reacting obtained aminated intermediates with cydopropylamine in presence of activated carbon in water within the temperature range of 100°C to 1I0°C to get N-cydopropyi-1,3,5-triazine-2,4,6-triamine.
10. The process of claim 9, wherein activated carbon is present in an amount of 1% to 3% of aminated intermediates.