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ACHIEVEMENTS

Market driven technologies

ACEPHATE

O,S-dimethyl acetyl phosphoramidothioate, commonly known as Acephate belongs to the class of organo phosphorous group of insecticides. This systemic insecticide controls wide range of insect pests in crops like cotton, rice, peanut, groundnut and other ornamentals.

Keeping the prevailing market potential in view, IICT has developed a cost-effective process for its preparation at 3kg/batch. This process technology is available for commercial licensing.

PROFENOFOS

O-ethyl-S-propyl-O-(4-bromo-2-chlorophenyl)phosphorothioate,commonly known as Profenofos is a non-systemic insecticide and acaricide with both contact and stomach action.

It was first introduced into world market under the trade name CURACRON by Ciba Geigy. It's considered the potential substitute for monocrotofos,(a product under review) for the control of whitefly menace in cotton. Realizing the potential IICT has developed an innovative environmentally benign bench scale process. This avoids the formation of ethyl mercaptan effluent. The process is available for licensing.

GLYPHOSATE

Glyphosate (N-phosphonomethyl glycine) is the world ’s largest selling herbicide. It is a pre emergent herbicide, controls the entire broad-leaved annual and perennial grasses in commercially important crops such as rice, wheat, soybeans, barley and sugarcane.

A process for its manufacture was worked out based on iminodiacetic acid as the starting material and successfully demonstrated to the sponsor M/s Lupin Agrochemicals Ltd, Mumbai, on a pilot scale.

Subsequently a non-IDA approach using ethanolamine as the raw material was worked out.

Oxidative dehydrogenation of N-phosphonomethyl ethanolamine yields glyphosate tribasic salt followed by electrodialysis produces free base of glyphosate.

An Indian process patent has been filed.

MONOCROTOFOS

Monocrotofos is highly versatile insecticide with systemic action, active against a wide range of insect pests. A new and innovative low temperature chlorination approach involving direct

chlorination of mono methyl aceto acetamide (MMA)in aqueous medium at moderate low temperatures was developed and passed on to several sponsors. This state of art technology produces 78% pure MCP. During the period IICT has helped in commissioning the commercial plants of M/s Pioneer products Ltd, New Delhi and also an integrated plant for the manufacture of chlorpyriphos and monocrotofos of M/s Tantech Industries limited, Chennai.

1,2,4-TRIAZOLE

1,2,4-Triazole is an important intermediate for triazole based agricultural fungicides and pharmaceutical anti-fungals. Realizing the importance, IICT has developed a single step effluent free approach for 1,2,4-triazole.The process is ready for commercial exploitation and licensing.

IMIDACLOPRID

Imidacloprid is the largest-selling insecticide belonging to neo-nicotinoid type of insecticides. This systemic insecticide acts on the nervous system of the insect causing irreversible blockage of post synaptic icotinergic acetylcholine receptor.

It controls effectively whiteflies, thrips, aphids, rice hoppers and sucking insects and soil insects like termites and biting insects. Imidacloprid is also used for seed dressing and soil/foliar treatment in a variety of crops like rice, cotton, cereals, maize, sugarbeet, potatoes, citrus and vegetables.

Attractive bio-efficacy and huge market potential emboldened IICT to develop a bench scale process for Imidacloprid.

An Indian process patent for the manufacture of intermediate (2-Nitroimino-1,3-)diazacycloalkanes)for Imidacloprid has been filed.

As an offshoot of this effort, IICT also filed a product patent(s) US 6479664,2002 (2-chloro-5-methyl-pyridine-3-carbaldehyde),an intermediate, US 6566528 (2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine)an analog of imidacloprid, which may find an application in agrochemical or pharma industries.

Technology for the manufacture of imidacloprid is available for licensing.

ESFENVALERATE

Esfenvalerate (S,S-Fenvalerate), a homo chiral single optical isomer is biologically more potent (4-times more active than Fenvalerate) synthetic pyrethroid.

M/s Sudershan Chemical Industries Ltd, Pune and M/s RPG Life Sciences ltd, Mumbai have entered into an agreement with IICT for the process know-how.

The complete technology package developed by IICT involved crystallization induced kinetic resolution method for the separation of S,S- isomer from fenvalarate-A. The IICT process comprises recovery and recycle of the entire undesired optical isomers as well as resolving agent apart from generating minimum effluents. The process has been successfully demonstrated at 3kg/batch to M/s RPGLS ltd,Mumbai.

A process patent for the preparation of (+)-2-(4-chlorophenyl)-3-methylbutanoic acid has been filed with PCT (483/02).Similarly,processfor the preparation of (S)-a-cyano-3-phenoxybenzyl-(S)-4-chlorophenylisovalerate has been filed with PCT. Racemisation studies on the unwanted R-isomer (acid) has been protected in the form of an Indian Patent

M/s Bharat Rasayan Ltd, New Delhi has been provided with process know-how package for the manufacture of Esfenvalerate.

1R-CIS-CYPERMETHRIN AND ANALOGUES FOR FMC (Hong Kong)

IICT and FMC (Hongkong) have entered bilateral agreement to deliver following 2 technologies on bench scale.

1R-CIS- (S)CYPERMETHRIN

Biologically the most active constituent of the eight optical isomers of cypermethrin, is a potent synthetic pyrethroid.

IICT process for the desired isomer consists of CRYSTALLISATION INDUCED KINETIC RESOLUTION using 1R-Cis-Permethric acid. The process has been successfully completed and the know-how package submitted in the month of March 2001.

RESOLUTION OF CIS-DV ACID

Resolution of cis-DV Acid (1-RS-CIS-DV-ACID)with different resolving agents has been studied. A result of the study was passed on to the sponsorer.

LAMBDA CYHALOTHRIN

Lambda cyhalothrin is a broad-spectrum insecticide belonging to pyrethroid group of insecticides. It is very effective for the control of variety of insect pests on cotton, rice and groundnuts.

This systemic insecticide exists as 1:1 mixture of the (Z)-(1R,3R),S-ester and (Z)-(1S,3S)R-ester of á -cyano-3-phenoxy benzyl-3-(2-chloro-3,3,3-trifluoro propenyl)-2,2-dimethyl cyclopropane carboxylate.

M/s ISAGRO ASIA Ltd, (Formerly RPGLS Ltd,Mumbai) entered agreement for the technology package. In response, IICT has worked out the complex technology for the manufacture of active CIS isomers by crystallization induced kinetic resolution technique. The process also comprises recovery and recycle of other undesired isomers thus improving the economy of the process.

Finally, the process was successfully demonstrated to the sponsorer on 1 kg/batch of active isomer

CHLORPYRIPHOS

An innovative process for the manufacture of chlorpyriphos based on trichloroacetylchloride and acrylonitrile was developed and transferred to 13 clients. Many clients commercialized the first of its kind technology in the world. IICT process generates 2,3,5,6-tetrachloropyridine (TCP) as a useful by-product along with 3,5,6-trichloropyridinol (HTCP), the intermediate required for CPP manufacture.

During the period an efficient and simple method was worked out for the recovery and conversion of 2,3,5,6-tetrachloropyridine at pilot plant level resulting in extra pure HTCP which in turn produced high quality CPP or CPP methyl. This process apart from solving storage of huge amounts of hazardous recycle streams, helped the various clients to improve upon their economy  by way of value addition in the form of rather difficult to produce chlorpyriphos methyl utilizing high quality HTCP obtained from the process.

A NEW BEGINNING

CONSORTIUM APPROACH OF INDIAN PESTICIDE MANUFACTURERS TO MEET CONSORTIUM APPROACH OF INDIAN PESTICIDE MANUFACTURERS TO MEET POST 2005 SCENARIO:TECHNOLGY FOR   INDOXACARB

Indoxacarb belongs to a new class of insecticides. It was introduced by DUPONT (USA) under the trade name AVUANT. It has excellent toxicological and ecotoxicological profile and controls the HELOTHIS pest in cotton in a shortest possible time of 2-4 hrs. It has a novel mode of  action and is relatively safe to beneficial insects.

  It thus qualifies as a component of IPM. All these attributes coupled with great degree of acceptance by the farming community of India, played a key role in the consortium of pesticide manufacturer association of India signing an agreement with the IICT for the technology development to meet the post 2005 product regime.

                Realising the importance, the IICT has developed a lab scale process for the preparation of indoxacarb. Work is in progress for scale-up of the process know-how for chiral product.

NEW MOLECULAR ENTITIES FOR AGROCHEMICAL APPLICATIONS

IICT-DUPONT (USA) COLLABORATIVE PROJECT ON NEW AGROCHEMICAL ENTITIES

IICT entered into an agreement with Dupont (USA) in 1995 for search of new chemical entities with potential pesticidal activity. During the period of 3 years (1995-98) IICT had synthesized and sent around 500 compounds for screening. Many a type of compounds from natural sources as well as synthetic origin belonging to various heterocycles like oxadiazines, triazoles, pyridines,  pyrazoles and pyridopyrimidines and CF 3 substituted pyridones have been sent for the screening program. The primary screening indicated 28 leads consisting of 17 herbicidal, 9-fungicidal and 2-insecticidal compounds.

PESTICIDES FROM PLANT SOURCES

Extracts of Azadiractha Indica (neem) and Annona squamosa (custard apple –seethaphal) are traditionally known sources of various bioactive principles.

After extensive efforts, IICT has developed new biopesticides based on neem and Annona squamosa along with their stable formulations.

A process patent on the dry powder formulation of neem enriched in azadirachtin content (upto 88%)and an emulsifiable concentrate with 30%of azadirachtin along with an appropriate process of their manufacture from neem seeds and kernels has been granted by US (No.5,856,526). Similar patents have been granted in Europe (EP 0834254)Canada (CA.2188110) Australia (AU 718883)and Japan (JP 3369413).

The process for the manufacture of emulsifiable concentrate of dry azadirachtin powders (from neem seeds and kernels) having purity upto 88% has been awarded with an Indian Patent (IN.182919) and a process patent (IN.184305)has also been granted for the dry powder.

A process patent for the manufacture of novel compounds based on isosquamosim from the seeds of custard apple (seethaphal) has been filed in US (NF 298/2000).

Going beyond this and to counter resistance problems, a technical grade biopesticide and stable formulations obtained from the seeds of neem and custard apple have been developed.

The bioefficacy of the single and mixed seed formulations were found effective in controlling the insect pests of several crops with performance superior to Endosulfan.

Pure acetogenins have been isolated from the technical material of custard apple in order to test their bio-efficacy.

LYCOPENE

Lycopene is an acylic carotenoid pigment. Lycopene is a powerful anti-oxidant that has shown results in neutralizing free radicals, especially those derived from oxygen, thereby conferring protection against prostate cancer, breast cancer, atherosclerosis and associated coronary artery diseases. It also reduces LDL oxidation and helps reduce cholesterol levels in the blood. It is considered to be a powerful nutrient in the human dietary system.

A process has been worked out to isolate Lycopene enriched oleoresin from tomato fruits followed by purification to yield Lycopene of  92%purity.Further work is in progress.