Synthesis Spectral and Antimicrobial Studies

SYNTHESIS SPECTRAL AND ANTIMICROBIAL STUDIES OF SOME THIAZOLE DERIVATIVES

A SUMMARY Submitted to the M.J.P. Rohilkhand University, Bareilly For the Degree Of DOCTOR OF PHILOSOPHY

in CHEMISTRY Supervisor : DR. A.K. AGARWAL Reader, Department of Chemistry Hindu College, Moradabad Submitted By :

NITIN ARYA

2007 SUMMARY Synthesis, Spectral and Antimicrobial Studies of some Noble Thiazole Derivatives

Submitted by :- Nitin Arya Supervisor :- Dr. A.K. Agrawal

The existence of thiazole ring system in nature was first demonstrated by Williams1 et.al. in 1935

2 while working on Vitamin B1, thiamine. It is also present in the well known class of antibiotics, the penicillins and another antibiotic, 4-oxathiazolidine3. Recently an antineoplastic cyclic peptide containing fused oxazole-thiazole units has been isolated from the marine tunicate, Lissoclinum patella4. In view of these findings, synthesis of bioactive thiazole derivatives developed during the past few decades.

Various 2-acylamino 5-nitrothiazole preparations in the form of gel are useful in treatment of

Trichomonas vaginalis infections5. Some thiazole carboxylic acid derivatives have been used against variety of fungus and bacterial infections6-8. 2-Aryl 3-acylthaizolidines have been found to show anti-inflamatory, analgesic, tranqualizer and antipyretic activities9, Sing et.al.10 have also reported anti inflamatory activity of some pyrazolyl-thiazole derivatives. In addition to this, some fluorinated thiazolo [3,2] pyrimidines and imidazothiazoles have also been reported as analgesic and anti inflamatory agents11,12. Hayashi13 et.al. have reported insecticidal activity of O,O dimethyl S-[(5-chloro-2 thiazolyl)methyl] phosphorodithioate. 4,5 Bis(d-methoxy phenyl) 2-(trifluoromethyl) thiazole have exhibited antiplatelet activity at very low concentration14. 2-(2 Amino 4-thiazolyl methyl) benzothiazoles or benzoxazoles and their pharma- cologically acceptable salts have been found to inhibit lipoxygenase and are useful as allergy inhibitors 15. A number of 2- arylamino-4 fluoro aryl thiazoles16 possessing antiartheritic effect have been synthesised by the cyclo-condensation of methyl ketones with appropriate thiourea. Many antidepressant and antianxiety thiazole derivatives have been synthesised by refluxing 2-formyl-aminothiazole formamide, hydrazine and treating the resulting solution with fumaric acid17. Thiazolylphenothiazines obtained by the condensation of 2-chloroacetyl phenothiazines with thio-amides and thiourea have anti-inflammatory activity18. Cysteamine derivatives which exhibited inhibition of adjuvant arthritis have been synthesised from 2-aminothiazoline19. 2-Amino 4(heterocyclylalkyl) 2-thioenyl thiazoles exhibiting antiulcer activity have been prepared by refluxing a mixture of 2-amino 4(5-amino alkyl 2-thienyl) thiazole, (ClCH 2CH2)2 O, Patassium iodide and potassium carbonate20. A series of 4-substituted 2-guanidino thiazoles inhibiting gastric proton pump enzyme have also been reported21. 2 Amino 4-aryl 5-arylazo thiazoles and 5-(Chlomanylazo) thiazoles possessing antibacterial activity 22,23,

2-Amino 4-methyl 5-thiazolyl phenyl sulphides and sulphones prepared by nucleophilic displacement of bromine in 2- amino 4-methyl 5-bromothiazole by a thiophenoxide followed by its oxidation and hydrolysis exhibited antibacterial activity against staphylococcus aureus and E.Col.24 2-(2-propenyl amino) thiazole prepared by the reaction of thiourea with ,  dibromo ethylacetate was found to be an effective bactericide for agriculture and horticulture. 2 Amino-4-chromanyl thiazoles possessing bactericidal activity were prepared by brominating and addition of thioureas with 6-acetyl chromoans26. 5-Chloro-2 aminothiazoles were found active against perculari oryzae (fungus) have been synthesised by the chlorination of 2-aminothiazole27. 2-Arylamino 4-aryl thiazoles exhibiting fungicidal activity against various fungi have been prepared by the condensation of appropriate ketones with arylthiourea28. The schiff bases exhibiting fungicidal activity have been prepared by the condensation of 2-amino thiazoles with aromatic aldehydes 29,30. Thiazolyl isoxazolines and thiazolyl pyrazolines exhibiting activity against penicillium notatum have been obtained by the Claisen-Schmidt

condensation of 5-acetyl 2-arylamino 4-methyl thiazoles followed by the reaction of the product with NH2OH and N2H4

respectively31. Haloureidothiazoles are effective broad spectrum herbicides32. The schiff bases of thiazoles with quinoline

were also found to exhibit herbicidal effect33. 2-Amino 1,3 dithiethane 2-thiazole useful insecticide has been synthesised

from 2-aminothiazole by reaction with carbon disulphide34,35. 4-Halo 5-nitro 2-arylaminothiazoles are useful pesticides

have been obtained by the reaction of 2,4-dihalo 5-nitrothiazole with appropriate aniline36.

The detailed study of literature revealed that most of the substituted thiazole derivatived have been

studied but still their is a scope to prepare some more substituted derivatives and screened them as antibacterial,

fungicidal and insecticidal activities.

The work may include the synthesis, spectral and antimicrobial studies of following thiazole

derivatives :-

(1)- 2-Amino 4-Aryl thiazoles :-

These may be synthesised by the reaction of suitable acetophenone, thiourea and iodine by direct

fusion method. The hydrogen iodide salt thus obtained on decomposition with ammonia solution may give the

required compound37. This time of fusion was varied depending on the number and nature of the groups

attached to the phenyl ring. The reaction employed is illustrated in scheme-I.

R R N COCH3 H2NCSNH2 I2

IH.H2N S

NH3 Soln. R N

Where R = 2-fluoro, 3-chloro 4-fluoro, 2-chloro 4-fluoro,

-3fluoro 4-methoxy, 2,3 difluoro, 2,4 difluoro, 2,3,4,5,6 penta fluoro, 4-fluoro 3-methyl etc. The name of the

parepared compounds are listed below :-

Table – 1 : 2-Amino-4-arylthiazoles Derivatives :-

Compd. No. Name M.P. (°C) 1a 2-Amino-4-(2-fluorophenyl) thiazole 95-6 1b 2-Amino-4-(3-chloro-4-fluorophenyl) thiazole 125-27 1c 2-Amino-4-(2-chloro-4-fluorophenyl) thiazole 131-32 1d 2-Amino-4-(3-fluoro-4-methoxyphenyl) thiazole 180-82 1e 2-Amino-4-(4-fluoronaphthyl) thiazole 158-60 1f 2-Amino-4-(2,3-difluorophenyl) thiazole 122-23 1g 2-Amino-4-(2,4-difluorophenyl) thiazole 108-9 1h 2-Amino-4-(2,3,4,5,6-penta fluorophenyl) thiazole 142-43 1i 2-Amino-4-(4-fluorophenyl) thiazole 110-12 1j 2-Amino-4-(4-fluoro-3-methylphenyl) thiazole 97-98 1k 2-Amino-4-phenylthiazole 151-2

With a view to study th effect of the fluorine atom on bioactivity various 2-Amino-4-arylthiazoles

synthesised were screened for their antimicrobial activities. None of the compounds were found active against gram

positive bacteria, S. aureus where as only compound 1a exhibited promising activity against gram negative bacteria, E.

Coli which may be attributed to the presence of fluorine on phenyl ring. Fungicidal activity of 2-Amino-4-aryl thiazoles

derivatives shows that the compound 1a to 1c and 1f to 1i exhibit activity against A. Flavus A. niger and C. Lunate where

as the non flurinated analog shows hardly any activity. Compound 1a and 1i are higly active against C. Lunata indicating the presence of only fluorine on aryl ring is effective. Compound 1d and 1e are totally inactive due to the naphthyl ring

instead of phenyl ring which inhibits the activity.

(2)- N, N' [(4aryl)-2-thiazolyl] Phosphorodiamido chloridates and N,N' di-[(4-aryl)-2-thiazolyl]

phosphorodiamido chlorothioates :-

These may be synthesised by the reaction of appropriate 2-amino 4-aryl thiazoles with

phosphoryl or thiophosphoryl chloride in ether. The reaction sequance is illustrated in scheme-2.

R R N N PXCl3+2

H2N S –2HCl Cl – P NH S

NH S Scheme-2 Where X= O or S, R= as given in Scheme-1.

The names of the compounds prepared are recorded in Table– 2.

Table – 2 : N,N'-Di-[(4-aryl)-2-thiazolyl] phosphorodiamido chloridates/ chlorothioates :-

Compd. No. Name M.P. (°C) 2a N,N’-Di-[4-phenyl)-2-thiazolyl] phosphorodiamido chloridate 100 2b N,N’-Di-[4-(4-fluorophenyl)-2-thiazolyl] phosphorodiamido chloridate 129-30 2c N,N’-Di-[4-(4-fluoro-3-methylphenyl)-2-thiazolyl] phosphorodiamido chloridate 125-27 2d N,N’-Di-[4-(3-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido chloridate 130-32 2e N,N’-Di-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido chloridate 80-2 2f N,N’-Di-[4-phenyl)-2-thiazolyl] phosphorodiamido chlorothioate 110 2g N,N’-Di-[4-(4-fluorophenyl)-2-thiazolyl] phosphorodiamido chlorothioate 158-60 2h N,N’-Di-[4-(4-fluoro-3-methylphenyl)-2-thiazolyl] phosphorodiamido chlorothioate 145 2i N,N’-Di-[4-(3-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido chlorothioate 154-6 2j N,N’-Di-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido chlorothioate 105-7

The organophosphorus derivatives are found to exhibit pronouncede pesticidal activity. Therefore few

compounds were screened for their insecticidal and fungicial activities Screening data of N,N’ Di-(4-aryl) 2- thiazoly

phospharomido chloridates indicates that most of the compounds are inactive against plutella. Sp. Only compound 2a

having a fluoro and methyl group on the phenyl ring showed promising activity.

(3)- N,N'-Di[(4-aryl)-2-thiazolyl] Phosphorodiamido fluoridates and N,N'-di-[(4-aryl)-2-thiazolyl]

phosphorodiamido fluorothioates :-

These may be synthesised by the reaction of N-N'-Di-[(4-aryl)-2-thiazolyl] phosphorodiamino

chloridates or chloro-thioates with potassium fluoride in benzene.

R R N N H H N N S S Cl – P = X KF F– P = X

R R N N

N S N S H Scheme – 3 H The value of R & X may be as given in Scheme 1 & 2.

All the compounds synthesised are given in Table – 3.

Table – 3 : N,N'-Di-[(4-aryl)-2-thiazolyl] phosphorodiamido fluoridates/ fluoro-thioates :-

Compd. No. Name M.P. (°C) 3a N,N’-Di-[4-phenyl)-2-thiazolyl] phosphorodiamido fluoridate 140 3b N,N’-Di-[4-(4-fluorophenyl)-2-thiazolyl] phosphorodiamido fluoridate 110-2 3c N,N’-Di-[4-(3-methyl-4-flurophenyl)-2-thiazolyl] phosphorodiamido fluoridate 158 3d N,N’-Di-[4-(3-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido fluoridate 162-4 3e N,N’-Di-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido fluoridate 100-2 3f N,N’-Di-[4-phenyl)-2-thiazolyl] phosphorodiamido fluorothioates 150 3g N,N’-Di-[4-(4-fluorophenyl)-2-thiazolyl] phosphorodiamido fluorothioates 117-20 3h N,N’-Di-[4-(3-methyl-4-fluorophenyl)-2-thiazolyl] phosphorodiamido fluorothioates 180-2 3i N,N’-Di-[4-(3-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido fluorothioates 135 3j N,N’-Di-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl] phosphorodiamido fluorothioates 172

Compound 3b and 3c and their corresponding thioanalogs 3f and 3g having only fluorine and methyl groups on the phenyl ring are quite active. Insecticide compound 3c shows 100% mortality indicating its possible use as an insecticide. Compound 3a and 3b exhibit promising activity indicating a better fungicidal effect of P = O compounds in comparision to those having P=S (3f).

(4)- O,O-Dialkyl N [(4-Aryl)2-Thiazolyl] Phosphorodamido Thioates :-

It may be prepared by adding cold etherial solution of 2-amino 4-aryl thiazole to appropriate O,O-

dialkyl phosphorochloridothioates and keeping the rection mixture at 0°C for 24 hours. The latter may obtained

by the reaction of dry alcohol on thiophosphoryl chloride in presence of sodium metal in benzene38.

Na RO

2R  OH + PSCl3 P  Cl RO R S N Condensation

H2N S R

N R’ O P H N S R’ O S

Scheme - 4

The value of R' may be ethyl or isopropyl while the value of R would be as in scheme 1.

By this method we synthesise a large seeries of compounds given in Table 4.

Table–4 : O,O-Dialkyl-N-[(4-aryl)-2-thiazolyl] phosphoramidothioates :-

Compd. No. Name M.P. (°C) 4a O,O-Diethyl-N-[(4-phenyl)-2-thiazolyl] phosphoramidothioate 145 4b O,O-Diethyl-N-[4-(4-fluorophenyl)-2-thiazolyl] phosphoramidothioate 211 4c O,O-Diethyl-N-[4-(4-fluoro-3-methylphenyl)-2-thiazolyl] phosphoramidothioate 95-97 4d O,O-Diethyl-N-[4-(2-fluoro-5-methylphenyl)-2-thiazolyl] phosphoramidothioate 116-18 4e O,O-Diethyl-N-[4-(3-chloro-4-fluorophenyl)-2-thiazolyl] phosphoramidothioate 160 4f O,O-Diethyl-N-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl] phosphoramidothioate 120 4g O,O-Diisopropyl-N-[(4-phenyl)-2-thiazolyl] phosphoramidothioate 97 4h O,O-Diisopropyl-N-[4-(4-fluorophenyl)-2-thiazolyl] phosphoramidothioate 93-94 4i O,O-Diisopropyl-N-[4-(4-fluoro-3-methylphenyl)-2-thiazolyl] phosphoramidothioate 86-8 4j O,O-Diisopropyl-N-[4-(3-chloro-4-fluorophenyl)-2-thiazolyl] phosphoramidothioate 155-57 4k O,O-Diisopropyl-N-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl] phosphoramidothioate 104-6

With a view of finding new insecticide and fungicide some of the above compound were tested. As

insecticide activity, compounds 4a and 4f are found to be totally inactive. Increased activity of compounds 4c, 4d, 4h and

4i indicates that the presence of additional group with fluorine increases the activity. Compound 4i shows maximum

mortality indicates that activity increases with the size and branching of the alkyl group and also that the presence of both chlorine and fluorine on aryl ring. The fungicidal activity of compound 4c having fluoro and methyl group attached to

phenyl ring shows largest activity.

(5)-(a).3-[4-Aryl)-2-Thiazolyl] imino 1,3 Dihydro 2H-Indol 2-ones :-

3-[4-Aryl)-2-Thiazolyl] imino 1,3 Dihydro 2H-Indol 2-ones may be prepared by the condensation of

indole 2-3 dione (1.47g) with appropriate 2-amino 4-aryl thiazoles (1.76g) in absolute alcohol and catalytic

amount of glacial acetic acid. The reaction sequence is shown in scheme - 5(a).

R R N O N N + S H2N S N O N O R R Scheme - 5(a)

The series of compounds prepared are listed in Table 5(a).

Table–5(a): 3-[(4-Aryl)-2-thiazolyl] imino-1, 3-dihydro-2H-indol-2-ones:-

Compd. No. Name M.P. (°C) 5(a)a 1,3-Dihydro-3-[(4-phenyl)-2-thiazolyl]-imino-2H-indol -2-one 200-2 5(a)b 3-[4-(2-Fluorophenyl)-2-thiazolyl] imino-1,3-dihydro-2H-indol-2-one 241 5(a)c 3-[4-(4-Fluorophenyl)-2-thiazolyl] imino-1,3-dihydro-2H-indol-2-one 185 5(a)d 3-[4-(4-Fluoro-3-methylphenyl)-2-thiazolyl] imino-1,3-dihydro-2H-indol-2-one 260 5(a)e 3-[4-(3-chloro-4-fluorophenyl)-2-thiazolyl] imino-1,3-dihydro-2H-indol-2-one 220-22 5(a)f 3-[4-(2-Chloro-4-fluorophenyl)-2-thiazolyl] imino-1,3-dihydro-2H-indol-2-one 327(d) 5(a)g 3-[4-(3-Fluoro-4-methoxylphenyl)-2-thiazolyl] imino-1,3-dihydro-2H-indol-2-one 230-32 5(a)h 3-[4-(4-Fluorophenyl)-2-thiazolyl] imino-1,3-dihydro-1-methyl-2H-indol-2-one 170-72 5(a)i 3-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl] imino-1,3-dihydro-1-methyl-2H-indol-2- 229-30 one

5(b). 1-[(4-Aryl)-2-Thiazolyl] spiro Aziridine 2,3'[3-H] Indol] 2-ones :-

1-[(4-Aryl)-2-Thiazolyl] spiro Aziridine 2,3'[3-H] Indol] 2-ones. The compound 5(a) can change into

compound 5(b) by treating it with etherial solution of diazomethane.

N N S N O R R CH2N2 N O N N + S H2N S N O N O Scheme - 5 (b) R The series of compounds prepared are listed in Table 5(b).

Table–5(b) : 1-[(4-Aryl)-2-thiazolyl] spiro [aziridine-2, 3'-[3h] indol]-2' (1'H)-ones :-

Compd. No. Name M.P. (°C) 5(b)a 1-[(4-phenyl)-2-thiazolyl] spiro [aziridine-2,3'-[3H] indol]-2' (1'H)-one 170 5(b)b 1-[4-(4-Fluorophenyl)-2-thiazolyl] spiro [aziridine-2,3'-[3H] indol]-2' (1'H)-one 195 5(b)c 1-[4-(4-Fluoro-3-methyl)-2-thiazolyl] spiro [aziridine-2,3'-[3H] indol]-2' (1'H)-one 178-80 5(b)d 1-[4-(3-chloro-4-fluoro)-2-thiazolyl] spiro [aziridine-2,3'-[3H] indol]-2' (1'H)-one 186 5(b)e 1-[4-(2-chloro-4-fluoro)-2-thiazolyl] spiro [aziridine-2,3'-[3H] indol]-2' (1'H)-one 300(d) 5(b)f 1-[4-(3-fluoro-4-methoxy)-2-thiazolyl] spiro [aziridine-2,3'-[3H] indol]-2' (1'H)-one 285 5(b)g 1-[4-(4-fluorophenyl)-2-thiazolyl]-1'-methyl-spiro [aziridine-2,3'-[3H] indol]-2' (1'H)- 200-2 one 5(b)h 1-[4-(2-chloro-4-fluorophenyl)-2-thiazolyl]-1'-methyl- spiro [aziridine-2,3'-[3H] 265-67 indol]-2' (1'H)-one Only componds 5(a)d and 5(b)d exhibits insecticidal effect may be due to the presence of fluorine and

methyl groups on the phenyl ringh. Compound 5(a)h shows 60% mortality may be due to the presence of

methyl group on indolyl nitrogen atom.

(6)(a).Spiro [2H-1, 3 Benzothiazine - 2-3' (3H) Indole] - 2', 4 (1H, 3H) diones :

(b).Spiro (3H-Indole-3, 2' thiazolidine] 2,4' (1-H) – diones :

Synthesis of Compound 6(a) :-The compound 5(a) 3-[(4-Aryl)- 2-thiazolyl] imino 1,3 dihydro 2-H-indole-2-ones

on treatment with o-mercaptobenzoic acid in acidic ethanol will give spirocompound 6(a), the spiro [2H-1,3

benzothiazine-2,3' (3H) indole] 2',4(1H, 3H) - diones.

N R N S N O R R S =O N Compd. 5(a) SH N + S COOH N O N O R Compd. 6(a) Scheme - 6(a)

Synthesis of Compound 6(b) :-

Synthesis of Spiro [3-H-indole 3,2'-thiazolidine] 2,4' (1H) diones involved the cyclocondensation of

compound 5(a) with mercaptoacetic acid in dry benzene.

R N N S N O R Dry HSCH2COOH Benzene

O R S N N S N O R

Scheme - 6(b)

The synthesized spiro compounds are listed in Table – 6.

Table – 6 : Spiro (3H-indole-3,2'-thiazolidine]-2,4' (1H)-diones :-

Compd. No. Name M.P. (°C) 6a 3-[(4-Phenyl)-2-thiazolyl] spiro [3H-indole-3,2'-thiazol idine]-2, 4' (1H) – dione 189-90 6b 3-[4-(4-Fluorophenyl)-2-thiazolyl] spiro [3H-indole-3, 2'-thiazolidine]-2, 4' (1H) - 220 dione 6c 3-[4-(4-Fluoro-3-methyl)-2-thiazolyl] spiro [3H-indole-3, 2'-thiazolidine]-2, 4' (1H) – 208 dione 6d 3-[4-(2-Chloro-4-Fluoro)-2-thiazolyl] spiro [3H-indole-3, 2'-thiazolidine]-2, 4' (1H) - 194 dione 6e 3-[4-(3-Chloro-4-Fluoro)-2-thiazolyl] spiro [3H-indole-3, 2'-thiazolidine]-2, 4' (1H) - 353-55 dione 6f 3-[4-(3-Fluoro-4-methoxy)-2-thiazolyl] spiro [3H-indole-3, 2'-thiazolidine]-2, 4' (1H) 176 - dione 6g 3-[4-(2-Fluorophenyl)-2-thiazolyl] spiro [3H-indole-3, 2'-thiazolidine]-2, 4' (1H) – 219-20 dione 6h 3-[4-(4-Fluorophenyl)-2-thiazolyl]-1'-methyl spiro [3H-indole-3, 2'-thiazolidine]-2, 4' 200-2 (1H) - dione 6i 3-[4-(2-Chloro-4-Fluorophenyl)-2-thiazolyl]-1'-methyl spiro [3H-indole-3, 2'- 270-9 thiazolidine]-2, 4' (1H) - dione

The compounds 6(b) i.e. (6a to 6i) were screened for their insecticidal activity against the larvae of

Hypera postica. Only compounds 6b, 6c, 6f and 6h showed conciderable activity by leaf feeding method showing thereby

that the nature of alkyl group does not effect the activity. Datas indicates that the presence of fluorine along with methyl or

methoxy groups enhances the activity whereas the presence of chlorine along with fluorine decreases the activity.

(7)- Synthesis of 2[1,1,1-trifluoro ethane sulphanamido] 4-aryl thiazoles :-

The compound may be prepared by refluxing equimolar quantity of 2-amino-4 arylthiazoles,

trifluoromethane-sulphonic anhydride which would be prepared by the dehydration of triflic acid by phosphorus

penta oxide.

2CF3SO3H + P2O5 [(CF3SO2)2O) + H2O

R (CF3SO2)2O + N NR

H2N S S (C2H5)3N NH2

N + (C2H5)3 NH.SO2CF3 S NHSO2CF3

Scheme - 7

The synthesised compounds are listed in Table – 7.

Table – 7 : 4-Ary-2-[1,1,1-trifluoromethanesulfonamido] thiazoles :-

Compd. No. Name M.P. (°C) 7a 2-[1,1,1-trifluoromethanesulfonamido]-4-phenylthiazole 110-12 7b 2-[1,1,1-trifluoromethanesulfonamido]-4-(4-fluorophenyl) thiazole 130-32 7c 2-[1,1,1-trifluoromethanesulfonamido]-4-(4-fluoro-3-methylphenyl) thiazole 98-100 7d 2-[1,1,1-trifluoromethanesulfonamido]-4-(3-chloro-4-fluorophenyl) thiazole 251 7e 2-[1,1,1-trifluoromethanesulfonamido]-4-(2-chloro-4-fluorophenyl) thiazole 120-22 7f 2-[1,1,1-trifluoromethanesulfonamido]-4-(3-fluoro-4-methoxyphenyl) thiazole 179 7g 2-[1,1,1-trifluoromethanesulfonamido]-4-(3, 4-difluoro phenyl) thiazole 92-95 7h 2-[1,1,1-trifluoromethanesulfonamido]-4-(1,2,3,4,5-penta fluorophenyl) thiazole 109-10

From the synthesised compounds, the compounds 7b to 7h were screened for their Herbicidal

activity. The compounds 7b and 7h are found to be active against the plants triticale vulgare and cicer arietinum where the

plant leaves becomes yellow indicating that the effect of these compounds was as photosynthetic inhibitors.

The Compounds 7b to 7h were tested against E. Coli and S. Aureus for their bactericidal activity. All

of these compounds are found to be active against gram negative bacteria, E. Coli whereas only a few of them show

slight activity against the gram +ve bacteria. Compound 7b, 7c and 7f exhibit promising activity against E. Coli which may

be due to the presence of fluorine and methyl group present on the phenyl ring of these componds.

Most of the above listed compounds were prepared through the above schemes (the details of the

methods are given in thesis). The purity of the compounds were checked by T.L.C. and the structure were proved by

elemental analysis, molecular weight determination, i.r., n.m.r. and mass spectrograph methods (The details are given in

thesis).

R E F E R E N C E S :-

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