The antimycotic activity of 16 o-nitrophenylhydrazones against strains of Hansenula anomala, Saccharomyces cerevisiae, Candida parapsyliosis, and Cryptococcus albidus was tested. All 16 compounds inhibited growth of the yeast strains. The inhibitory activity of the 4 methyl-derivatives substituted on the aromatic nucleus was particularly significant

Asproni, Battistina

Boatto, Gianpiero

Cerri, Riccardo

Farris, Giovanni Antonio

Palomba, Michele Francesco Luigi

Pau, Amedeo

Pintore, Giorgio Antonio Mario

English

UnissResearch

/L FARMACO. 51 (1). 79-84 (1996) 
FUNGICIDAL ACTIVITY OF SOME o-NITROPHENYL-HYDRAZONES 
MICBELE PALOMBA. GiO.RGIO PINTORE, GIANPIERO BOATTO. BATTISTINA AsP.RONI. RICCA.RDO CERlU (*), AMEnEO PAU, 
GIOV ANN! ANTONlO F A.RRIS (**) . 
Istituto di Analitica Farmaceutica. Universita deg/i stud; di Sassari. Via Muroni 23. (J7100 Sassari 
(**) Dipartimento di Scienze Ambientali Agrarie e Biotecnologie Agro-Alimentari, sez. Microbioiogia. 'University df Sassar;. 
. , 
Summary - The antimycotic activity of 16 o.nitrophenylhydrazones against strains of Hansenula 
anomala. Saccharomyces cerevisiae. Candida parapsylosis. and Cryptococcus albidus was tested. All 16 
compounds inhibited growth of the yeast strains. The inhibitory activity of the 4 methyl-derivatives 
substituted on the aromatic nucleus was particularly significant~ 
INTRODUCTION 
The activity of nitrophenylhydrazones as inhibitors 
of the growth of some pathogenic microorganisms in 
plants has already been described!·2. More recently, 
other Authors3 reported the effective fungicidal 
activity of o-derivatives of phenylpyridylamines with . 
general formula (A). which are compounds similar to 
'the 0- nitrophenylhydrazones prepared by us (B). 
NOR 
11 
~ 
Q = Pyridyl 
Phenyl 
x = H. CH3• Cf. OCH3 
R1 = H; R2 = (CHW CH3• (CH2h-CH3 
R1 = CH~ R2 = CHrCH3• (CHzh-CH3 
These findings encouraged us to prepare and screen 
. a series of 16 new o-nitrophenylhydrazones of aldehydes 
and aliphatic ketones for antimycotic activity . 
These assays (worked out at the Dipartimento di 
Scienze Ambientali Agrarie e Biotecnologie Agro-
A1imentari, sez. Microbiologia, University of Sas sari) 
provided some interesting results. All the prepared 0-
nitrophenylhydrazones assayed at concentrations 
ranging between 50 aIld 400 "g/ml showed inhibitory 
activity. Compounds 2, 6, 10 and 12 (Table I) were 
particularly active, being able to inhibit growing 
colonies at concentrations lower than 50 "g/ml. 
A correlation between structure and inhibitory 
activity can be hypothesized. The linear chains R2 (see 
Table I) were more active than the corresponding 
branched ones. Concerning the substituent X of the 
aromatic nucleus, the best pharmacological effects were 
obtained when CH3 was present, whereas when Cl was 
present compounds were inactive. 
CHEMISTRY 
All products used m the tests were synthesized as 
shown in Scheme 1, starting from 4-substituted 0-
nitroanilines (C) which were transformed into 
hydrazines (D) and condensed with aldehydes and 
ketones to obtain the corresponding derivatives. 
Yields were generally good. The prepared compounds 
are listed in Table 1. For all the unknown compounds 
the spectroscopic and mass data useful for their 
characterization are reported in Table 11. 
'~H-NH.z O· 
. 0:2 snCl:l 
x = H. CH3. Cl, OCH:3 
(*) To whom correspondence should be addressed 
R1 = H; R2 = (CHili-CH3• (C~:rCH3 
R1 = CH3; R2 = CHrCH3. (CH2b-CH3 
80 M. Palomba, G. Pintore, G. Boatto, B. Asproni, R. Cerri, A. Pau, G. A. Farris 
TABLE I - List of the, prepared compounds 
~ N<l.2 'R2 
N° X R1 ~ yeld% pJ.oC 
1 H H' -(C~)rCH, 81 59-Q0 
2 CH3 H -(CH2)rCH3 81 ~9 
3 Cl H -(CH2)rCH3 74 63-64 
4 OCH, H -(CH2)rCH3 78 102-103 
5(4) H H -(CH2h-CH, 74 39-40 
6 CH, H -(CH2h-CH3 79 57-58 
. 
7 Cl H -(CH2)rCH3 82 71-72 
8 OCH3 H -(C~h-CH3 85 70-71 
9';>) H CH, -CHrCH, 78 73' 
10") CH, CH, -CHrCH3 93 81-82 
1111} Cl CH, -CHrCH3 74. 70-71 
12 OCH3 C~ -CHrCH3 72 75-:76 
13(11) H CH3 -(CH2)x-CH3 83 51-52 
14 CH, CH,' -(CH2)x-CH, 64 33 
15'" Cl CH3 -(CH2)rCH, 76 82-83 
16 OCH3 CH, -(C~)x-CH3 68 54-55 
Reference numbers are given for compounds already reported 
in the literature. 
FUNGICIDAL ACTIVITY 
The compounds were tested for inhibition of the 
growth of the pathogenic strains: 1) 201 Hansenula 
anomala 2) 1090 Saccharomyces cerevisiae 3) 2813 
Candida parapsy/osis 4) 3053 Cryptococcus a/bidus. 
All strains were obtained from the Dipartimento di 
Scieme Agrarie e Biotecnologie Agro-Alimentari, sez. 
Microbiologia, University of Sassari. 
Solutions of the products to be assayed were prepared 
in eight different concentrations (50, lOO, 150,200, 250, 
300, 350 and 400 p.g/ml). GYEP culture medium was 
used for fungal growth. 
. Blank and inhibition tests with a 50 p.g/ml 
concentration of miconazole were also carried out; 
counting the Colony Forming Units (CFU) 48 h after 
having inoculated the culture medium. The results are 
shown in Tables Ill, IV, V and VI. They give the CFU 
expressed as exponential notations for each compound 
at each. concentration (fLg/ml). The data are 
summarized in Table VII. 
At the maximum dose (400 ",g/ml), the formation 
of yeast colonies was strongly inhibited. The growth 
reduction factor was calculated as follows: 
100- (CFU-comp.)-{CFU + comp.) 
(CFU-comp.) 
It was over 99.90/0 in almost all cases. 
Table VII shows the concentrations in ",g/ml which 
caused growth inhibition in the strains tested t giving 
a result between 0+ 1()2 CFU, compared with 1()9 in 
the blank test. Two (6 and 10) of the most active 
compounds were tested at concentrations between 5 and 
25 ",g(inl. The results are reported in Table VIII. Both 
TABLE II - Physical and spectrometric properties of the new. compounds 
. , 
Comp. Formula M.W. GC-MS IR(cm' ) 1HNMR (6) 
M+Jz 
·NH C=N ·NO? COCI.. 
1 C10H1:\NlIO, 207.2 Compatible 3300-1630-1500 1.00 (t. H. -CH:\l; 1.60 (m. 2H .CH~_CH:\l; 2.37 (q. 2H -miTCH,.CHlI>; 
1340 7.33 (m 5H 4H arom. +1H methyleniC); 10.70(s 1H NH> 
2 C11H1!iNlIO, 221.2 Compatible 3300-1630-1500 1.00 (t. H. -CH:\l; 1.62 (m. 2H -CHn<!:b-CH:\l; 2.28 (s. 3H Ar-CHlI>;2.33 (q. 
1330 I~ -CH,.c.J;b-CH:\l; 7.36 (m. 4H. 3H arom. HH melhylenic); 10.64 (s. 1H 
3 C, oH, ,Nao,c' 241.7 Compatible 3300-1630-1500 1.00 (t. 3H. -CH:\l; 1.61 (m. 2H. -CH:nd:b-C~; 2.34 (q. 2H. -9!,-CH,. 
1330 CH,,): 7.37-8.13 (in. 4H 3H arom. +1H methylentC); 10.66 (s 1H. NH) 
4 Cu!'iv;N:\Oll 237.2 Compatible 3285-1630-1500 0.99 (t. H. -CH:\l; 1.59 (m. 2H -CH,.gj,-CH:\l; 2.32 (q. 2H. -gtb-CH,.cHlI>; 
1320 3.79 (5. 3H. Ar-OCH:ll; 7.15-1.19 (m. 4H. 3H aram. +1H rnethylenic); 10.66 (s 1H,NH)' . 
6 C,?H17N:\O, 235.3 Compatible 3300-1630-1510 0.94 (t, 3H. -CH:\l; 1.41 (m. 2H. -CH,.); 1.55 (m. 2H. -CH,.); 2.28 {s, 3H Ar-
1330 CH3l;2,35 (q. 2H -CH,); 1.34 (m. 4H. 3H 8lOm. ""H methy\enic); 10.64 (5, 
1H~H). 
7 C11H,4N:\O,CI 255.7 Compatible 3300-1820-1500 0.94 (t. 3H, -CH:\l; 1.41 (m,2H. -CH,.); 1,56 (m.2H. -CH,.); 2,37 (q. 2H, • 
1330 CH?); 7.37-8.13 (m. 4H 3H arom. ",'H methytenlC); 10.66 cs. 1H. NH) 
8 C,?1'i17N:\O:\ 251.3 Compatible 3290-1625-'''95 0,93 (t, H. -CH:\l; 1 . .tO (rn. 2H. -CH,.); 1.55 (m. 2H. -CH,.); 2.33 (q, 2H. -
1325 CH,.) .3.79 (5. 3H. At-OCH3>; 7,16-7,18 (m. 4Ho 3H arom. ... 1H methylenic); 
10.68 (5 1H NH) 
12 C11H1!'iN:\O:\ 237.2 Compatible 3315-1620-1510 1.18 (t. H. -CH3>;1.98 (5. 3H. C~); 2.39 (q. 2H. -9::!?-CH,.cH:\l; 3.81 (S, 3H. 
1335 Ar-OCH~:7.17-7.86 Cm 3H aroni.); 10,61~ 1H NH> . 
14 C"H17NlIO? 235,3 Compatible 3300-1830-1500 0.99 (t, H. -CH:\l: 1.64 (m,2H -CH:r9::b-CH:!>; 1.98~. 3H.CHa); 2.29 (s, 3H 
1330 ;~CH:\); 2.35 (t. 2H ~H,.cHa); 7.3!>-7,92 (m. H atOm.); 10.59 (s. 1H. 
16 C"H17N:\°a 251,3 Compatible 3310-1630-1500 0.96 (t. 3H. -CH:V; 1.63 (m. 2H. -CH'-c-':b-CH;V; 1.97 (s. 3H CHlI>;2.34 (t, 
1335 2H -Q::b-CH,-CH:\l; 3.80 (5. 3H. Ar-OCHa); 7.11-7.64 (m. 3H. atOm.); 10.60 
'(S 1H NH) 
Fungic:ida/ ac:tivity of some o-nitrophenyl-hydrazones 
TABLE III - Growth inhibitory activity of compounds 1. 2. 3 and 4 
~N=CI+-(CH2l2~ 
COMPOUND 1(R = H) 
YEASTS CONCENTRATIONS (pg/ml) 
0 50 100 150 200 -250 
201 4.10" 2.10" 2.10~ 2.10 0 0 
1090 6.10" 4.10' 8.10' 4.10' 6.10~ 0 
2813 6.10" 2.10" 810 4.10 0 0 
3053 2.10" ".10~ 0 0 0 0 
COMPOUND 2 (R = CH3) 
YEASTS CONCENTRATIONS (IIQIml) 
0 50 100 150 200 250 
201 4.10" 4.10" 6.10 0 0 0 
1090 6·tO" 2.10' 6.10' 4.10" 2.10 0 
2813 6.10" 6.1~ 4.10" 6.10' 0 0 
3053 2.10" 2.10 6.1~ 2.10' 0 0 
COMPOUND 3 (R = Cl) 
YEASTS CONCENTRATIONS~wml) 
0 50 100 150 200 250 
201 4.1It 6.10· 4.10" 8.10' 6.10' 0 
1090 6.10" 4.10" 4.10" 6.10" 6.10" 4.10" 
2813 6.10" 6.10 ".10 6.10" 2.10" 6.10" 
3053 2.10" 6.1 a> 4.10 2.10 0 0 
COMPOUND 4 (R = OCHa) 
YEASTS CONCENTRATIONS (pg/ml) 
0 50 100 150 200 250 
201 4.1~ 4.10 4.10 0 0 0 
1090 6.10" 4.HI" 4.10' 6.10' 2.1a> 8.10" 
2813 6.10" 4.10" 2.10" 4.1 a> 4.10' 4.10 
3053 2.10' 6.10" 2.10' 0 0 0 
TABLE IV - Growth inhibitory activity of compounds 5, 6, 7 and 8 
~-
COMPOUND 5 (R = H) 
YEASTS CONCENTRATIONS (IIQIml) 
0 50 ' 100 150 200 250 
201 10' 10" 10' 10' 10' 10' 
1090 10· 10" 10" - W 1a> 10~ 
2813 10· 10" 10' 10" -10' 10 
3053 10" 10" 10" 10" 10 10" 
COMPOUND 6 (R = CHa) 
YEASTS CONCENTRATIONS (1IQIm1) 
0 50 100 .150 200 250 
201 10· 0 0 0 0 0 
1090 10" 11f 0 0 0 0 
2813 10· 10" 10' 0 0 0 
3053 10· 11f 0 0 0 0 
COMPOUND 7 (R :: Cl) 
YEASTS CONCENTRATIONS (JIO/ml) . 
0 50 100 150 200 250 
201 10" 10· 10" 10" 10 10' 
1090 10" 10' 10" 10" 10" 10:. 
2813 10" ~ 10" 10 10" 10" 
3053 10" 10·- 10" 10" 10" 10" 
COMPOUND 8 (R = OCHa) 
YEASTS CONCENTRATIONS ~ml) 
0 50 100 150 200 250 
201 10" 10 10' 11f 10" 10" 
1090 10" 10 10· 10' 10" - Hr 
2813 10· 10 10' 10' 10" 0 
3053 10" 1Il 10" 10' 10" 10" 
300 
0 
0 
0 
0 
300 
0 
0 
0 
0 
, 
300 
0 
6.10' 
8.10 
0 
300 
0 
6.10 
o . 
0 
300 
,10' 
W 
10' 
10· 
300 
0 
0 
0 
0 
300 
10" 
10" 
10" 
10" 
300 
10' 
10' . 
0 
10' 
81 
350 400 
0 0 
0 0 
0 '0 
0 0 
350 400 
0 0 
0 0 
'0 0 
0 0 
350 400 
0 0 
2.10" 8.1a> 
6.10 4.10 
0 0 
350 400 
0 0 
0 0 
0 0 
0 0 
350 400 
10' 10 
11f 1a> 
10' 10' 
10" 10· 
350 400 
0 0 
0 0 
0 0 
0 0 
350 400 
10" 10' 
10" 1t 
10" le 
10a 1e, 
350 400 
10' 0 
10' 0 
0 0 
10' 0 
82 M. Polombo. O. Pintore, O. Bootto, B. Asproni. R. Cerri. A. Pou. G. A. Fortis 
TABLE V ~ Growth inhibitory activity of compounds 9, 10, 11 and 12 
COMPOUND 9 R = H) 
~_~STS 
0 50 
201 10' 10" 
1090 10· 10" 
2813 10· 10" 
3053 10" 10" 
COMPOUND 10 (R = CH3) 
YEASTS 
0 50 
201 10 0 
1090 10 10" 
2813 11l 10' 
3053 10 1Cf 
COMPOUND 11 eR = Cl) 
YEASTS 
~ ~N=C-cHz~ 
CONCENTRATIONS (IJO/ml) 
100 150 200 '250 
Hl" 10~ 10" 10 
1~ 10~ 1~ 10" 
10" 10" 10" 0 
10' 10' 10 W' 
CONCENTRATIONS (ualml) 
100 150 . 200 250 
0 0 0 0 
0 0 0 0 
10" 0 0 0 
0 0 0 0 
CONCENTRATIONS (I'Q/ml) 
t 
0 , 50 100 150 200 250 . I 
201 10' 10" 10" 10" 10" 10" 
1090 10" 10' 10" 10' 10' 1~ 
2813 10" 10" 10' 1~ 1~ 10" 
3053 10· 10" 10" 10 10 10· 
COMPOUND 12 (R = OCH3) 
YEASTS CONCENTRATIONS (IIQIml) 
0 50 100 150 I 200 250 
201 10' 10' 10" 10" 10" 10" 
1090 10' . .10" 10' 10" 10" 10" 
2813 10" 10" 1~ 10" 10" 0 
3053 10· 10' 1~_· . 10'_ 10" 10" 
TABLE VI - Growth inhibitory activity of compounds 13, 14, 15 and 16 
. ~ 
~~-cH:s o . ~ 
COMPOUND 13 (R = H) 
YEASTS CONCENTRATIONS MIIml) . 
0 50 100 150 200 250 
201 10' 10" 10" 10" 10' 10" 
1090 10" 10" 10 10 10' 10' 
2813 10' 10" 10' 10' '10' 10' 
3053 10' 10" 10"_ 10" 10 10' . 
COMPOUND 14(R = CH3} 
YEASTS CONCENTRATIONS_C!!!JIml) 
0 50 _ 100 150 200 250 
201 10" 10' 10' 1~ 10"' 10" 
1090 10 10" 10" 10" 1Q"' 10~ 
2813 10 10" 1~ 1~ 10' 10" 
3053 11l 10 10 10" 10' 10" 
COMPOUND 15 (R = Cl) 
YEASTS CONCENTRATIONS fiiglml) 
a 50 100 150 200 250 
201 10' 10" 10" 10· 10· 10" 
1090 10' 10" 10" 10 10 10" 
2813 10' 10" 10" 10 10 10' , 
3053 10" 10" 10' 10 10' 1~ 
COMPOUND 16 (R = OCH3) 
YEASTS 
--0- --50- - 100 CONCENTRATIONS (/IQ/ml) .----- 150 200 250 
201 10" 10" 10" 10" 10 10" 
1090 10" 10· 10" 10' 10 10" 
2813 10" 10" 10" 10" 10" 10' 
3053 10" 10" 10" 10· 10" 10~ 
300 350 T 400-
10 10 10 
10" 10" 10". 
0 0 0 
1~ 10" . 0 
I 
300 350 400 
0 0 0 
0 0 0 
0 0 0 
0 0 0 
i 
300 350 400 
11t 1Cf 1Cf 
1(f 10~ 1(f 
10" 10" 10" 
10" 10" 10" 
300 350 400 
10" 10" 10" 
10" 10" 10" 
0 0 0 
10" 10 10 
300 350 400 
10" 10" 10" 
1~ 1~ 10~ 
10' 10" 10 
10" 10" 10' 
300 350 ..00-
10" 10" 10" 
10" 10" 10" 
10" 10" 10" 
10" 1Jr_ 10 
300 350 400 --
11t 11t 10 
10" 10" 10 
10' 0 0 
1(f Ht' 10' 
360-r--350 - '400--
1ete .10' 10" 
10" 10~ 10" 
1(f 10" 10" 
10~ 1(f 1~ 
Fungicidal activity of some o-nitrophenyl-hydrozones 83 
TABLE VIl- Concentrations of compoun~ tested (J.tg/ml) producing less than 1()2 CFU after 48 h 
Corn ound$ Yeasts tested 
201 Hans. an. 3053 Saa:. car. 2813 Cand par, 1090 Crypt alb 
1 100 100 
2 100 150 
3 200 100 
4 100 100 
5 150 >400 
.6 <50 100 
7 >400 >400 
8 250 300 
9 200 250 
10 <50 100 
11 >400 >400 
12 100 150 
13 300 >400 
14 200 300 
15 >400 >400 
16 >400 400 
Miconazole <50 <50 
TABLE VIII - Growth inhibitory activity of compounds 
6 and 10 at concentrations of 5-25 I'g/ml 
COMPOUND 6 
YEASTS CONCENTRATIONS (J.IQImIl 
0 5 15 25 
201 3.10" . 2.10"_ 8.10 3.104 
1090 5.10" 6.10" . 3.10 2.1W . 
2813 2.10". 5.10" 3.10" . 6.1ct 
3053 2.10" 3.10" 6.10" 7.10" 
COMPOUND 10 
YEASTS CONCENTRATIONS (J.IO/mI) 
0 5 15 25 
201 3.10" 2.10Q 4.104 0 
1090 5.10" 5.10" 6.10" 2.10" . 
2813 2.1~ 3.10" 2.10' 3.10" 
3053 2.10" 6.10" 3.1 et' 7.10" 
MICONAZOLE 
YEASTS CONCENTRATIONS (uo ml) 
0 5 15 25 
201 0 0 0 0 
1090 0 0 0 0 
2813 0 0 0 0 
3053 0 0 0 0 
they have a CH3 in 4 on the aromatic nucleus and a 
linear alkyl chain of 4 or 5 C atoms on hydrazone N; 
the best results were shown by compound 6 (CH3 in 
4 and linear chains of Se). 
It is probable that these substituents play an essential 
role in crossing the cell m~mbranes of the yeasts. as 
confIrmed by the relatively higher resistance to 
inhibition of Saccharomyces cerevisiae strain) 1090 
150 250 
100 150 
150 >400 
200 250 
350 >400 
100 100 
400 >400 
100 250 
150 350 
100 100 
250 >400 
100 150 
350 >400 
200 150 
350 350 
350 >400 
<50 <50 
. which has thicker membranes than the other strains 
tested. 
Future research will assess any other effects produced 
by longer (and therefore more lipophilic) alkyl chains 
inserted in the position 4 of the aromatic system. Our 
research will be extended to include inhibitory activity 
against bacterial strains pathogenic for human beings. 
CHEMICAL EXPERIMENTAL SECTION 
PREPARATION .oF Q-NITROPHENYLHYDRAZINES 
The reaction was performed in alcohol bath at a temperature 
between -5°C and 0 °C using 0.3 moles of the appropriate 0-
nitroaniline suspended in concentrated HCI (Scheme 1). The 
cooled suspension was slowly added with NaN02 solution (20 
g in 60 mlof H20). Following. a SnCb.2H20 in Ha solution 
(125 g in lIS ml of cone. HCI) was dropped. 
The resulting crude product was filtered under vacuum, 
washed with cold H20, and dissolved in boiling H20. To the 
filtered warm solution CH3COONa was added. The 
precipitated o-nitrophenylhydrazine was filtered and dried. For 
each compound yield was about 60-65010. 
PREPARATION OF o-NlTROPBENYLHYDRAZONES 
A solution of the appropriate o-nitrophenylhydrazine in 
ethanol (w/v 1:5-1:10) was added with 1-2 drops of conc. HCI 
and a stoichiometric quantity. plus a 10010 excess, of the 
appropriate ketone or purified aldehyde. The hydrazone 
crystallized directly from the cooled alcohol solution and was 
recovered by ftltration. . 
The products were analyzed by TLC and melting point 
determined using a Kofler apparatus. Molecular structures were 
assigned by IR spectroscopy IH-NMR and confirmed by GS-
MS analysis (see Table 2). 
MICROBIOLOGICAL EXPERIMENTAL SECTION 
The following yeasts were used: strain 1090 of Saccharomyces 
cerevisiae. strain 201 of Hansenula anomola, strain 2813 of 
Candida parapsylosis, strain 3053 of Cryptococcus albidus. All 
84 M. Pa/omba, G, Pintore, G. Boatto. B. Asproni. R. Cerri, A • .Pau, G. A. ForTis 
strains were obtained from, the Dipartimento di Scienze 
Ambientali-Agrarie e Biotecnologie Agro.-Alimentari; sez. 
Microbiologia, University of Sassari. ' 
GYEP culture medium (21170 glucose, 0.5% yeast extract, 1 % 
bacteriological peptone. 2% agar, in aqueous solution) was 
sterilized at 115°C for 30 min. Mother solutions of 0-
nitrophenylhydrazones in ethanol at a concentration of 10 mglml 
were prepared and added to the GYEP in order to obtain 
concentrations of 50, lOO, 150,200,250,300.350,400 "glml 
of o-phenylhydrazones.The solutions were then placed in fetri 
dishes and inoculated with eight different concentrations (10-
10-8) of appropriate precultures of yeast strain. Precultures of 
the yeast strains were grown.in liquid GYEP (as above but 
without the agar). The same procedure was used for comparison 
with miconazole at a single concentration of 50 I'glml. Ablank 
test was also carried out, using the same culture medium without 
the addition of the tested compounds. Colony Forming Unit 
(CFU) counts were made after 48 h. The results are shown in 
Tables Ill, IV, V. and VI and summarized in Table VII. 
ACKNOWLEDGMENTS 
We kindly appreciate Ms. Luisanna Lecis and Ms. 
Carla Sotgiu for their collaboration. 
REFERENCES 
(1) Kururay Co. Ltd., .Jpn. Koka; Takio, 80. 118,434 (1980) C.A. 
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(4) R. CERRI, G.BoATro, A. PAU, F. SPARATOllE, P. MANCA,II 
Farmaco Ed. Sc;., 43, 113 (1988). ' 
(S) H. BAUER. E. STRAUSS, Be,.., 65. 308 (1932). 
(6) Z. J. VEJEDELElC., Chem. Listy, 51.1338 (1957) C.A.51, 17874i 
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Received July 15, 1995; accepted .July 31, 1995. 


PESCE SCHlTO,

Fungicidal activity of some o-nitrophenyl-hydrazones

Fungicidal activity of some o-nitrophenyl-hydrazones

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