Chemical Papers (2021) 75:2121–2133
2123
Synthesis of: 2‑amino‑N’‑(2‑cyano‑2‑(arylhydrazono)
extracted in 80% acetone. The homogenates were trans-
ferred quantitatively to centrifuge tube, and centrifuged at
1
3
acetyl)‑benzohydrazide derivatives (B; H L ‑H L )
2
2
1
000 rpm for 3 min. The remaining was washed many times
According to our previous preparation (Katouah et al. 2019),
in which 0.005 mol of NaNO (0.345 g in 5 ml H O) was
by acetone, ꢁltered oꢀ, and then, the ꢁltrate was completed
to deꢁnite volume (8 ml). The absorbance of clear extracts
was recorded at 480, 644, and 663 nm, and the concentra-
tions of photosynthetic pigments (chlorophyll a, chlorophyll
b, and cartenoids) were calculated (ug/ml) as described pre-
viously (Metzner et al. 1965).
2
2
added slowly to 0.005 mol aniline derivatives suspension
(
p-nitroaniline, p-acetylaniline, or p-anisidine), which cold
at 0-5ºC in 1.5 ml HCl (conc.). Each diazonium chloride
solution (freshly prepared) was added slowly to cold solution
of compound A, (0.005 mol, 1.081 g) in ethanol/ sodium
acetate (15 ml/3 g). The mixture of each reaction was stirred
for 2 h at 0-5ºC till precipitation. The products (Scheme.
Estimation of sucrose and total sugar (TSS)
1
) were ꢁltered oꢀ, washed, and recrystallized from ethyl
Using powdered dry leaves, the extraction of sugar was
carried out. Known weights of powdered leaves (0.1 g),
were mixed with alcohol and then shacked over-night. Each
mixture was ꢁltered oꢀ and washed, and then, the ꢁltrates
were completed (by alcohol) to known volume (10 ml) and
kept in refrigerator. The sucrose was evaluated by 5.4 N
KOH (0.1 ml), and 0.1 ml from extracts was hydrolyzed at
97 °C for 10 min. 3 ml fresh anthrone (150 mg in 100 ml
H SO , 72%) were added to extracts. The mixtures were
1
−3
alcohol to produce the derivatives (H L ). All deriva-
2
tives were characterized and reported (Katouah et al. 2019),
2
-Amino-N’-(2-cyano-2-(4-acetylphenylhydrazono)acetyl)
1
benzohydrazide (H L ) is red powder derivative, and has
2
1
yield of=74%, m.p.=205–207 °C. Its H NMR (DMSO-d )
6
spectrum showed; /ppm=3.81 (s, 3H, OCH ), 6.72 (s, 2H,
3
NH ), 6.90–7.85 (m, 8H, Ar–H), 10.22 (s, 1H, NH), 10.85
2
(
s, 1H, NH), 11.15 (s, 1H, NH). 2-Amino-N’-(2-cyano-2-(4-
2
4
2
nitrophenylhydrazono)acetyl) benzohydrazide(H L ) is a
heated at 97 °C for 5 min. After cooling, the intensity of
developed green color was spectrophotometrically deter-
mined at 620 nm (Handel 1968). The amount of sucrose
was estimated using standard curve prepared by pure sugar.
The sucrose concentrations were expressed as mg/g dry
weight. TSS was evaluated in alcoholic extracts by mix-
ing 0.1 ml with 3 ml fresh anthrone solution. The mixture
was boiled in water both for 10 min and then cooled. The
intensity was determined based on absorption at 625 nm.
The amounts of TSS were evaluated using standard curve
prepared using pure glucose (Yemm and Willis 1954). The
data were statistically analyzed using COHORT/COSTAT
program (798 Lighthouse Ave. PMB 329, Monterey, CA,
93,940, USA). The least signiꢁcant diꢀerence (LSD) test
was used to compare means with significance level at
P ≤ 0.05.
2
derivative, by yield=68% and m.p.=205–207 °C. 2-Amino-
N’-(2-cyano-2-(4-anisylhy drazono) acetyl) benzohydrazide
3
(
H L ) is a reddish-brown derivative, by yield of=57% and
2
m.p.=205–207 °C (Katouah et al. 2019). High similarity in
spectral features of divers’ derivatives may refer to the fara-
way position of substituents, which leads to non-remarkable
eꢀect on functional groups.
Synthesis of Zn(II)–HL1−3 complexes
5
mmol of Zn(NO ) ·6H O were dissolved in absolute
3 2 2
ethanol and then added to ethanolic solution of ligand
(
2.5 mmol) as 2 M:1L molar ratio. Each reaction mixture
was heated under reꢂux for 4–8 h, which varied from com-
plex to another. The precipitates were ꢁltered oꢀ, washed,
and dried over anhydrous CaCl .
2
Measurements techniques
Application of proposed fertilizer
Elemental content was determined using Perkin-Elmer 2400
CHN Elemental Analyzer, while zinc content was evaluated
by complexometric titration (Vogel 1986). Molar conductiv-
ity of complexes was recorded upon JENWAY model 4070
First, the corn hybrid plant has been cultivated in three boxes
that irrigated by water for a few days. Then, one from boxes
2
was irrigated by a suspension from Zn(II)–H L complex
2
1
(
0.5 mmol, 0.409 g) and ammonia by 0.5 mmol (0.400 g).
conductance bridge. IR spectra for solid KBr disc and H,
1
3
6
The second box was irrigated by free ammonia (NH NO ,
CNMR (DMSO-d ) were recorded on JASCO FT-IR-4100
4
3
−
1
1
mmol), while the third by water only.
spectrophotometer (400–4000 cm ) and Burker 500 MHz,
respectively. Electronic spectra were conducted on UV
2
Estimation of photosynthetic pigments
Unicam UV/Vis spectrophotometer in DMSO solvent. XRD
patterns were obtained (10˚ < 2θ < 90˚ range) using X-ray
diꢀractometer (GNR, APD2000PRO, Italy) with graphite
Using an ice-cold porcelain mortar, the photosynthetic pig-
ments in a known weight of fresh leaves were grinded and
−
1
mono-chromator (0.03° min , Cu/Kα1 radiation). SEM
1
3