Studies In the Synthesis of Betti’S Products Rhoda Nine As Pharmacological Activities and Potential Fungicides

Fungicidal activities of Betti’s products Rhodanine, Quinolinols and Arylidene in a large variety of these compounds has been found to the Therapeutic value. Previously fungal infection was regarded as an uncommon disease. Now in recent years fungal infections are worldwide in nature and are systemic as well as local and rural or remote area of all ages. The well-known fungal diseases are candidiasis, dermatomycosis, mycosis and tineaversi colour. Organic compounds with rhodanine and quinoline moiety are of much interest to research worker’s in the field of synthetic analytical and pharmacological activities. A large number of hydrazide, hydrazone’s have shown significant ameobicidal activities. Many remedies have been used against infections and research still continues which would lead one to conclude that the ideal topical antifungal agent has not yet been found. The Betti’s products 2-thio-4-Keto thiazolidenes, 8-quinolinols and lactones have been found to be effective as antifungal activities. 2-Thio-4-Keto-Thiozolidine, known as rhodanine, is an important five membered heterocyclic compound which possesses a reactive methylene group at position five sulphur containing compounds are known for their pharmacological activities, antimicrobial activity has been found to be associated with thiazolidenone and Arylidene rhodanines are also used for analytical applications.

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In recent work of Thesis further investigation of related compounds synthesized in laboratory and found anti-fungicidal activities. It is intended to persure the present work along the following lines. First phase of the work proposed in synthesis or preparation of some 2- mercapto-4- keto-thiazolidene and its derivatives to condensed some newly synthesized aromatic aldehyde to assess their analytical and fungicidal activity.

The pharmaceutical industry started to show great interest for the preparation of newly Betti’s products. Fungicidal activities of Betti’s products rhodanine, and quinolinols derivatives or aromatic aldehyde in a large variety of these compounds has been found to the therapeutic value. The Betti’s products 2-Thio-4-Keto-thiazolidene and cyano ethyl aromatic aldehyde. With condensed and formation of some Betti’s products. Substituted rhodanine are well known for their analytical application 5-Arylidene rhodanine and p-dimethylamino benzylidene rhodanine is among the more important analytical reagents for the detection of metals and their fungicidal activity of newly synthesized rhodanine derivatives with following aldehyde.

In the present Investigation p-dimethylamino benzaldehyde and five newly synthesized aldehyde have been condensed with rhodanine in presence of glacial acetic acid and freshly fused sodium acetate and newly 5-arylidene rhodanine have been obtained and investigated antifungal activity of 5-(4-NN-BIS-2-carboxy ethylamino-2-methyl Benzylidene) rhodanine. Chemistry of rhodanine :- Due to presence of reactive methylene group at position five and replaceable hydrogen atom at position three, it has been thought to synthesized some new derivatives for studying their fungicidal activity.

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The reaction of 5-arylidene rhodanine with primary aromatic amine and formaldehyde in presence of ethanol is known as arylamino methylation. The Newly synthesized 5-(4-NN-bis -2’-carboxy ethylamino-2-methyl-benzylidene) rohdanine (R=CH3, R’=H) has been condensed with formaldehyde and ten aromatic primary amine under the reaction condition of mannich. Ten arylamino methylated rhodanines of the type 3-( - substituted aniline methyl) -5- (4-NN – BIS –2’ – carboxy – ethylamino -2- methyl – Benzylidene) rhodanine. Compounds were tested for Their antifungal activity against CURVULARIA LUNATE and HELMINTHOSPORIUM ORYZAE following the disc diffusion and Hanging drop method and tested antifungal activity of aniline-methylated rhodanine has been found to be most effective against fungi and show good fungicidal activity of compounds (IV,V,VI.VII, VIII). The Fungicidal activity of these compounds has given in table.

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All the Products No. 1 to 6 Table were screened in VITRO Against Curvularia Lunate and Helmenthosporium oryzae by disc diffusion and hanging drop methods. Table No.1 show fungicidal activity quite comparable to commercial fungicide chloromy cetin.

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2- condensation of primary aromatic amines with 5-arylidene rhodanine. The reaction of aromatic amines with rhodanine was performed first of all by grancher [12] recently bux and shukla [15] have synthesized a series of such products and found anti-amoebical activity.

In the present investigation ten primary aromatic amines have been condensed with 5-arylidene-rhodanine (r=ch3 r’=h) by the procedure as recomonded by bux and shukla [15] new products of rhodanine derivatives have been obtained. 2-(imino-substituted-phenyl) – 5 - (4-nn-bis-2’carboxy ethyl-amino-2-methyl benzylidene) 4-thiazolidinones. Table no.02

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2-9imino-substituted-phenyl)-5-(-4-nn-bis-2’-carboxy ethyl amino -2-methyl-benzylidene)-4-thiazolidinones Table no.03 I.r.absorption frequencies of -2-(iminophenyl)-5-(-4nn-bis-2’-carboxy ethyl amino-2-methyl-benzylidene)-4-thiazolidinone

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All this compound table no.04 were tested for their fungicidal activity against curvularia lunate and helminthosporium oryzae. Chloro and methoxy group at position 4 in benzene nucleus increase the toxicity to both the species of fungi.

Reaction of phenyl hydrazine with rhodanine has been studied by grancher[12] . The reaction of semicarbazide with rhodanine in aqueous solution (alcoholic) presence of barium carbonate, rhodanine derivatives of semicarbazide are obtained in good yield.

In the present investigation it was thought worthwhile to synthesized some new rhodanine derivatives by the condensation of malonanilic acid hydrazide and 5-arylidene rhodanine in presence of barium carbonates in ethanol medium on water bath products of 2 (substituted malonanilic acid hydrazide) 5-(4-nn-bis -2’- carboxy ethyl –amino 2-methyl – benzylidene) 4-thiazolidinones.

Funglcidal activity of all the campounds table no.05 there tested for their antifungal activity against same fungi in table no.05 Table no.05

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2-(substituted malonanilic acid hydrazido)-5-(-4-nn-bis-2’-carboxy ethyl amino-2-methyl-benzylidene)-4-thiazolidinones

FUNGICIDAL ACTIVITY:-

All the compounds (table no.5) were tested for their antifungal activity against curvularia lunate and helminthosporum oryzae by the disc diffusion and hanging drop method. The result has been compared with commercial fungicide chloromycetin. The highest fungicidal activity has been showed by the compound. The result of fungicidal activity has been recorded in table no.5 Table no.06 Antifungal activity of 2-(substituted malonanilic acid hydrazido)-5-(4-nn-bis-2’-carboxy ethyl amino-2- methyl-benzylidene)-4-thiazolidinones

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In the present investigation it was thought worthwhile to synthesize some condensation products of dapsone with 5-arylidene rhodanine for testing their antifungal activity. In the present study 5-arylidene rhodanine have been condensed with. Dapsone in an oil bath at 1800 – 2000c adopting the procedure of Bux and Shukla[15] and six New products of 4-4-BIS-Amino-5(p-di-methyl amino benzylidene rhodanine diphenyl sulphone) were obtained. All the New synthesized compounds were tested for their fungicidal activity against Curvularia Lunate and Helminthosporium oryzae.

The fungitoxicity data obtained indicate that all the compounds table no.7 are promising fungicides. The activities vary from strong to moderates on both the fungal species. All the compounds table 7 were tested for their fungicidal activity against curvularia lunat and helminthosporium oryzae by the disc diffusion and hanging drop methad. Synthesised new campound show highest fungicidal activity .

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The results have been compared with commercial fungicide chloromycetine fungicidal data of these compounds are recorded in table no.7 (a) Table no.07 Condensation products of 5-arylidene-rhodanines and dapsone Table no.07 Condensation products of 5-arylidene-rhodanines and dapsone

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Table no. 7(a) Fungicidal activity of the products

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