13C NMR spectra and biological activity of N-(1H-benzimidazol-2- yl)benzamides

Article abstract of DOI:10.1134/S1070363206100264

Derivatives of 1H-benzimidazol-2-amine and halo-, nitro-, methoxy-, and hydroxy-substituted benzoic acids were synthesized, and their fungicide activity against pure Fusarium culmorum and Helminthosporium sativum cultures and pathogenic microflora of wheat and barley seeds in laboratory and field tests was studied. Some compounds were found to exhibit a strong fungicide activity. Nauka/Interperiodica 2006.

Full text of DOI:10.1134/S1070363206100264

ISSN 1070-3632, Russian Journal of General Chemistry, 2006, Vol. 76, No. 10, pp. 1653 1659.
Pleiades Publishing, Inc., 2006.
Original Russian Text V.S. Pilyugin, Yu.E. Sapozhnikov, A.M. Davydov, G.E. Chikisheva, T.P. Vorob’eva, E.V. Klimakova, G.V. Kiseleva, S.L. Kuzne-
tsova, R.D. Davletov, N.A. Sapozhnikova, R.Kh. Yumadilov, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 10, pp. 1725 1731.
13C NMR Spectra and Biological Activity
of N-(1H-Benzimidazol-2-yl)benzamides
V. S. Pilyugin, Yu. E. Sapozhnikov, A. M. Davydov, G. E. Chikisheva,
T. P. Vorob’eva, E. V. Klimakova, G. V. Kiseleva, S. L. Kuznetsova,
R. D. Davletov, N. A. Sapozhnikova, and R. Kh. Yumadilov
Research Technological Institute of Herbicides and Plant Growth Regulators,
Academy of Sciences of Bashkortostan Republic,
ul. Ul’yanovykh 65, Ufa, 450029 Bashkortostan, Russia
Received January 27, 2006
Abstract Derivatives of 1H-benzimidazol-2-amine and halo-, nitro-, methoxy-, and hydroxy-substituted
benzoic acids were synthesized, and their fungicide activity against pure Fusarium culmorum and Helminthos-
porium sativum cultures and pathogenic microflora of wheat and barley seeds in laboratory and field tests was
studied. Some compounds were found to exhibit a strong fungicide activity.
DOI: 10.1134/S1070363206100264
Benzimidazole derivatives constitute a large and
chemically versatile class of compounds. Their bio-
logical action is not limited to helminths but extends
to pathogenic fungi, viruses, and bacteria [1 25]. An
interesting group of benzimidazole derivatives con-
sists of various 1H-benzimidazol-2-ylcarbamic acid
esters (derivatives of 1H-benzimidazol-2-amine)
which have found wide application as fungicides. The
simplest benzimidazole derivative of this kind is
methyl 1H-benzimidazol-2-ylcarbamate (I, Carbend-
azim); it is widely used in agriculture as systemic
fungicide.
stituted benzoyl chlorides in toluene or acetone we
obtained a series of new derivatives at the nitrogen
atom in position 1 of the benzimidazole ring or at the
exocyclic amino group in position 2 (compounds III
XLI). It should be noted that the acylation of 1H-
benzimidazol-2-amine with acid chlorides under mild
conditions initially occurs at the N1 atom. Heating of
the reaction mixture (or a solution of preliminarily
isolated isomer A in an appropriate solvent) promotes
migration of the acyl group to the exocyclic nitrogen
atom to give isomer B (Scheme 1). The rearrangement
process was monitored by HPLC and 13C NMR
spectroscopy.
Analysis of available published data shows that
many acyl derivatives of 1H-benzimidazol-2-amine at
the exocyclic amino group in the 2-position exhibit
strong biological activity, whereas data on the activity
of analogous derivatives at the ring nitrogen atom are
considerably fewer in number. The goal of the present
study was to develop methods of synthesis of a series
of amides derived from substituted 2-hydroxy- and
2-methoxybenzoic acids and 1H-benzimidazol-2-
amine (II) (at the endo- or exocyclic nitrogen atom)
and examne their fungicide activity under comparable
conditions.
The structure of the resulting amides, derivatives
of 1H-benzimidazol-2-amine and substituted benzoic
acids, was confirmed by the 13C NMR spectra (Tab-
le 1). The position of the acyl group was determined
taking into account that structures with a substituted
exocyclic amino group give a simpler spectral pattern
due to fast proton exchange between the N1 and N3
atoms in the heteroring. The presence of an acyl group
at the exocyclic nitrogen atom induces a considerable
upfield shift of the C2 signal ( = 5 8 ppm), while
C
shielding of the C3a and C7a atoms is weaker.
The syntheses of methyl ester I used as reference in
biological tests, some acyl derivatives of 1H-benz-
imidazol-2-amine, halo- and nitro-substituted salicylic
acids, and the corresponding acyl chlorides, as well
as the structure of these compounds according to the
13C NMR data, were described by us previously [26].
By acylation of 1H-benzimidazol-2-amine with sub-
All substituents in the examined compounds ex-
hibit weaker or stronger electron-withdrawing pro-
perties (except for 4-aminobenzamide XXX, guani-
dine derivative XXIII, and octanamide XV) and
reduce electron density on the heteroring. On the basis
of the NMR data we compared the substituent effects
with variations in magnetic shielding on protonation
1653

1654
PILYUGIN et al.
Scheme 1.
O
C N C R
H
N
N
N
C NH2
C NH2 + RCOCl
N
H
N
N
H
=O
C
R
II
A
B
V, VII, X, XXIV,
XXXIII, XLI
III, IV, VI, IX, XI XXII,
XXV XXXII, XXXIV, XXXV
NH
N
N
C NHCOOCH3
N
C NHC NH2
N
H
H
Cl
XXIII
XXXVI
H
O
N
Cl
Cl
N
+
C N C OCH3
C NH2 OC(O)R
N
H
N
H
H
XXXVII
XXXVIII XL
III, R = MeO; IV, R = 2-MeO-3,5-Cl2C6H2; V, R = 2-MeO-3,5,6-Cl3C6H; VI, R = 2-HO-3,5-Cl2C6H2; VII, XXXV,
XXXIX, R = 2-MeO-3,5-Cl2C6H2; VIII, XL, R = C6H5; IX, R = 2-HO-3,5-Br2C6H2; X, R = 2-MeO-3,6-Cl2C6H2; XI,
R = 2-HO-5-BrC6H3; XII, R = 2-HO-5-ClC6H3; XIII, R = 2-HO-5-O2NC6H3; XIV, R = 2-HO-3,5-I2C6H3; XV, R =
C7H15; XVI, R = 2-MeO-5-ClC6H3; XVII, R = 2-MeO-5-BrC6H3; XVIII, R = 3-IC6H4; XIX, R = 2-Cl-5-O2NC6H3; XX,
R = 4-O2NC6H4; XXI, R = 3-BrC6H4; XXII, R = 2-BrC6H4; XXIV, R = 2-MeO-3,5-Cl2C6H2; XXV, R = ClCH2CH
(OH)CH2; XXVI, R = 3,5-(O2N)2C6H3; XXVII, R = 2,4-Cl2C6H3; XXVIII, R = 2-Cl-4-O2NC6H3; XXIX, R = C6F5;
XXX, R = 4-H2NC6H4; XXXI, R = 3-ClC6H4; XXXII, R = 2-HOC6H4; XXXIII, XXXIV, XXXVIII, R = 2-MeOC6H4;
XLI, R = 3-BrC6H4.
of the heteroring. As follows from the data of [27, 28],
protonation of benzimidazole ring leads to an upfield
shift of the C2, C4, C7, C7a, and C3a signals by 5
8 ppm. This is consistent with our data for compounds
in the protonated form in organic acid solutions. The
observed variations of the protonation-induced
chemical shifts are comparable with the substituent
effects.
substituted benzoic acid, this is the result of formation
of an intramolecular hydrogen bond with participation
of the hydroxy proton and carbonyl oxygen atom.
The chemical shift of C2 in benzamide VIII is
C
149.4 ppm. Introduction of an electron-withdrawing
substituent (Cl, NO2, Br) into the benzene ring leads
to displacement of the C2 signal to
153.6 ppm
C
(XVIII). In the 13C NMR spectra of structures acy-
lated at the endocyclic nitrogen atom (N1), the C2
Magnetic shielding of the amide carbonyl carbon
atom (C8) in the series of the examined compounds
was found to depend on the substitution pattern in the
aromatic ring. The chemical shift of C8 does not
signal is located in the
range from 146.8 (XXXIII)
to 154.7 ppm (VII). AsCa result of asymmetric sub-
stitution of the benzimidazole fragment, a slight dif-
ference in the magnetic shielding of the C7 and C4
exceed
165.6 ppm (VII) for structures containing
nuclei is observed [ (C7, C4)
2 3 ppm].
a methoxCy group in the ortho position with respect to
the carbonyl group. Considerable deshielding of C8 is
produced by the neighboring hydroxy group: the
Fungicide activity of the compounds under study
was estimated at a concentration of 0.003% against
Fusarium culmorum and Helminthosporium sativum
signal shifts downfield to
171.8 ppm (XI). As with
C
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13C NMR SPECTRA AND BIOLOGICAL ACTIVITY
1655
Table 1. 13C NMR spectra and yields of 1H-benzimidazol-2-amine derivatives
3
4
3a N
5
6
2
H
C NH2
10 11
14 13
N
8
7a
C N C 9
O
N1
7
12
8
=O
C
9
N
H
10
11
14
13
C
12
A
Chemical shifts C, ppm
CH3,
O Alk
a
a
C2
C4
C5
C6
C7
C7
C3
C8
C9
C10
C11
C12
C13
C14
I
II
99 143.5 112.7 125.3 125.3 112.3 127.7 127.7 152.8
150.2 112.1 124.4 124.4 112.1 128.9 128.9
54.3
III
IV
V
VI
VII
VIII
IX
X
XI
XIII
XIV
XV
99 144.5 113.0 124.4 124.4 113.0 128.8 128.8 172.0
22.4
90 148.4 114.1 122.3 122.3 114.1 134.8 134.8 152.8 129.0 131.8 134.8 122.3 152.8 128.6 62.5
98 153.0 111.5 122.8 126.5 113.9 127.1 128.9 164.2 127.1 153.0 126.6 133.3 129.5 134.2 61.9
48 156.5 112.7 124.1 124.1 112.7 132.9 132.9 170.7 121.6 150.9 122.1 128.4 122.8 129.5
82 154.7 112.7 120.4 125.3 116.7 127.6 129.3 165.6 132.4 152.0 130.0 133.5 127.0 129.3 62.7
77 149.4 114.0 122.3 122.3 114.0 134.8 134.8 169.2 132.8 129.0 129.0 134.0 129.0 129.0
33 150.8 112.6 124.1 124.1 112.6 131.8 131.8 170.5 122.5 157.6 112.6 138.1 109.1 129.4
89 152.9 111.7 123.6 125.6 113.9 127.2 129.0 164.3 133.0 153.8 126.6 134.5 126.7 129.4 62.1
57 151.5 112.6 123.8 123.8 112.6 129.7 129.7 171.8 122.1 160.4 120.2 136.3 109.7 132.4
31 150.7 112.7 123.9 123.9 112.7 128.9 128.9 170.5 119.7 167.8 119.1 129.7 138.9 126.6
67 150.8 112.6 123.9 123.9 112.6 129.5 129.5 170.3 122.1 160.6 80.6 149.0 89.5 138.6
55 144.2 114.0 125.7 125.7 114.0 129.2 129.2
152.8
68.0,
31.8,
25.7,
28.9,
28.7,
22.6,
14.7
XVIII
XIX
XX
80 153.6 111.8 122.7 122.7 111.8 131.0 131.0 169.2 132.6 138.4 94.8 140.3 132.6 129.1
72 150.5 113.4 123.0 123.0 113.4 132.7 132.7 169.1 138.3 138.8 132.3 126.0 146.6 125.3
87 152.5 112.8 123.9 123.9 112.8 131.4 131.4 170.8 143.8 130.3 123.1 149.7 123.1 130.1
79 151.4 113.2 122.8 122.8 113.2 131.7 131.7 169.9 139.0 132.7 122.1 134.8 131.1 128.0
61 147.9 114.5 122.5 122.5 114.5 133.5 133.5 168.8 135.8 119.7 132.2 138.5 128.7 129.8
61 159.2 112.5 120.5 120.5 112.5 137.8 137.8
XXI
XXII
XXIII
XXVI
159.4
54.6
89 153.5 112.4 123.7 123.7 112.4 129.9 129.9 165.9 131.7 128.7 148.8 120.9 148.8 128.7
XXVII 80 148.5 114.2 122.5 122.5 114.2 135.7 135.7 168.0 132.2 131.4 130.5 134.8 127.9 130.0
XXVIII 91 150.0 113.5 123.0 123.0 113.5 133.0 133.0 169.5 143.9 131.9 125.3 148.7 123.0 131.0
XXXI
79 152.4 113.5 122.7 122.7 113.5 138.3 138.3 169.5 132.2 139.0 132.2 146.2 132.6 126.8
XXXIII 34 146.8 112.8 121.9 121.9 112.8 131.0 131.0 165.1 121.4 157.8 114.8 134.2 121.4 137.0
XXXVI 61 144.3 114.2 125.8 130.5 112.9 128.7 126.8 152.8
a
Yields, %: XII, 71; XVI, 21; XVII, 63; XXIV, 76; XXV, 26; XXIX, 25; XXX, 32; XXXII, 44; XXXIV, 32; XXXV, 70; XXXVII,
35; XXXVIII, 95; XXXIX, 94; XL, 93; XLI, 79.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 10 2006

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PILYUGIN et al.
Table 2. Toxicity of 1H-benzimidazol-2-amine derivatives at a concentration of 0.003% against pure fungi cultures
Inhibition of growth of pathogenic
fungi, %
Inhibition of growth of pathogenic
fungi, %
Compound no.
(A: B molar
ratio)
Compound no.
(A: B molar
ratio)
Fusarium
culmorum
Helminthosporium
sativum
Fusarium
culmorum
Helminthosporium
sativum
I
III
IV
V
VI
VII
VIII
IX
X
XI
100
36.3
28.5
47.5
68.5
12.1
100
34.0
54.6
8.7
22.9
7.6
7.7
25.7
30.5
XXIII
XXIV
XXIV
XXV
XXV
XXVI
11.2
32.8
15.7
35.3
36.1
26.4
12
18.4
22.7
0
0
22.9
73
17.6
23.5
0
XXVII
XXVIII
XXIX
2.8
5.1
19
24.1
15.6
7
XII
32.1
77.3
16.8
0
11.2
41.7
28.3
86.1
0
XXX
29
1
XIII
XIV
XVI
XVII
XVIII
XX
28.7
20.3
19
XXXII
XXXIII
XXXIV
XXXV
XXXVI
XXXVII
XXXVIII
XXXIX
XL
15.9
75.8
51.4
12.1
87.3
63.5
15.0
31.7
30.2
90.1
4.6
25
17
19.8
14.7
6.8
10.9
20.0
XX
(50.0: 50.0)
XXI
XXII
84.7
17.6
15.6
16.2
XLI
34.4
pathogenic fungi as pure cultures (Table 2) and in-
fected seeds (Tables 3 7).
XXXVII, and XLI are toxic for phytopathogenic
fungi. These compounds were recommended for
further testing. As follows from the data in Table 2,
their fungicide activity is fairly strong; however, most
of them are slightly less toxic than Carbendazim (I)
Primary laboratory tests showed that compounds
VI, VIII, XIII, XX, XXI, XXXIII, XXXVI,
Table 3. Fungicide activity of some 1H-benzimidazol-2-amine derivatives against pathogenic infections of Voronezhskaya
wheat seeds
Pathogenic microflora
Compound
no.
Dose,
kgton
Germination
capacity, %
Weight of
100 germs, g
1
efficiency with respect
to control, %
affected, %
Control
I
79
83
77
69
14.6
14.7
1.0
10
(Carbendazim)
III
IV
V
VI
VII
1.0
1.0
1.0
1.0
1.0
87
81
82
78
80
48
67
68
67
68
38
13
12
13
12
13.7
14.2
14.6
14.5
10.8
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13C NMR SPECTRA AND BIOLOGICAL ACTIVITY
1657
Table 3. (Contd.)
Pathogenic microflora
Compound
no.
Dose,
kgton
Germination
capacity, %
Weight of
100 germs, g
1
efficiency with respect
affected, %
to control, %
VIII
IX
X
XI
XII
XIII
XIV
XV
XXIII
XXXVI
XXXVII
XLI
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
82
76
75
86
84
84
80
80
81
85
82
84
45
78
87
42
49
32
69
64
48
46
51
49
42
0
0
14.4
14.6
14.0
14.5
14.3
15.0
14.2
13.4
13.9
13.9
13.4
13.8
47
36
58
11
19
38
40
34
36
Table 4. Efficiency of 1H-benzimidazol-2-amine derivatives XXXIII and XXXIX
Compound
no.
Dose,
kgton
Laboratory germination
capacity, %
Affection of seeds by
fungi, %
Weight of 100 germs,
g
1
Control
I
87
88
59
37
13.7
14.2
0.5
(Carbendazim)
1.0
0.5
1.0
0.5
1.0
90
91
93
84
86
44
9
7
12
4
14.1
13.5
13.8
13.8
12.2
XXXIII
XXXIX
Table 5. Selective toxicity of 1H-benzimidazol-2-amine derivatives toward spring wheat seeds
Compound
no.
Dose,
l ton
Laboratory germination
capacity, %
Affection of seeds by
root rot, %
Weight of 100 germs,
g
1
Control
I
89
94
43
32
14.0
13.7
2.5
(Carbendazim)
Raxil
XLI
0.5
2.0
2.0
90
93
95
5
26
22
13.4
13.8
13.7
XXXVI
with respect to Fusarium culmorum. Benzamide VIII
showed the highest activity against both Fusarium
culmorum and Helminthosporium sativum and was
superior to Carbendazim (I). The above-listed com-
pounds attract interest for studying their toxicity with
respect to other fungi species, as well as components
of binary fungicide compositions.
The fungicide activity of some compounds was esti-
mated by the reduction of affection of seeds produced
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1658
PILYUGIN et al.
Table 6. Efficiency of 1H-benzimidazol-2-amine derivatives against root rot during vegetation of spring wheat
Root rot
Compound
no.
Dose,
l ton
Field germination
capacity, %
1
affection, %
biological efficiency, %
70.6
Control
I
64.8
80.2
40.1
11.8
2.5
(Carbendazim)
XXXVI
XLI
2.0
2.0
84.6
78.0
11.2
11.5
72.1
71.3
Table 7. Effect of 1H-benzimidazol-2-amine derivatives on the crop yield of spring wheat
Number of Weight of
Gain in
crop yield,
g/m2 10
Compound
no.
Dose,
l ton
Number of
Stem
Ear
Crop yield,
g/m2 10
seeds in
an ear
1000 seeds,
g
1
stems/m2 length, cm length, mm
1
1
Control
I
218
270
81.7
84.0
72.3
76.4
23.9
23.6
7.3
7.9
14.2
17.8
2.5
3.6
(Carbendazim)
XXXVI
XLI
2.0
2.0
295
286
82.6
79.2
75.7
69.1
24.2
23.8
7.2
7.0
19.4
18.4
5.2
4.2
by root rot. This procedure ensures estimation of
integral fungicide activity, for root rot is caused by a
set of pathogenic Fungi imperfecti belonging to dif-
ferent stems (Helmintosporium, Fusarium, etc.).
Infection persists on the seed surface and develops
upon germination under moist conditions. The phyto-
toxicity of compounds can be estimated concurrently
by the germination capacity and change in the weight
of germs relative to control. From the compounds to
be tested we prepared 30% film-forming free-flowing
pastes, and seeds were treated with these pastes. The
results of treatment of seeds of Voronezhskaya wheat
are given in Table 3. It is seen that some compounds
exhibit fungicide activity at a dose of 1.0 kg (cal-
culated on the active substance) per ton of seeds, i.e.,
the effect is higher than or similar to that of widely
used Carbendazim (I). Specifically, the following
compounds must be noted: N-(1H-benzimidazol-2-yl)-
acetamide (III), N-(1H-benzimidazol-2-yl)-3,5-di-
chloro-2-hydroxybenzamide (VI), N-(1H-benzimida-
zol-2-yl)benzamide (VIII), N-(1H-benzimidazol-2-yl)-
5-chloro-2- hydroxybenzamide (XII), N-(1H-benz-
imidazol-2-yl)-2-hydroxy-5-nitrobenzamide (XIII),
N-(1H-benzimidazol-2-yl)guanidine (XXIII), methyl
(5-chloro-1H-benzimidazol-2-yl)carbamate (XXXVI),
methyl (5,6-dichloro-1H-benzimidazol-2-yl)carbamate
(XXXVII), and (2-aminobenzimidazol-1-yl)(3-bro-
mophenyl)methanone (XLI), whose technical ef-
ficiency considerably exceeded that of ester I.
Field tests were performed to estimate the efficiency
of seed protectants against root rot and their influence
on the sowing of seeds and crop yield. The data given
in Tables 4 7 indicate that further studies on the
above compounds, specifically 1H-benzimidazol-2-
amine derivatives XXXVI and XLI (unfortunately,
field tests of benzamide VIII were not performed), are
promising. Moreover, studies on the fungicide activity
of compositions for seed treatment should be extended
to estimate their toxicity with respect to Ustilaginales
and other fungi species inducing plant affections
during seed germination and vegetation.
EXPERIMENTAL
The 13C NMR spectra were recorded on a Bruker
CXP-100 Fourier-transform spectrometer at a frequency
of 22.63 MHz; the spectra were measured both with
and without decoupling from protons. Dimethyl
sulfoxide was used as solvent, and hexamethyldisil-
oxane, as reference. Signals were assigned (Table 1)
by analyzing the chemical shifts, coupling constants,
multiplicities, and signal intensity ratios; the data for
model compounds and the results of calculation of
magnetic shielding in the benzene ring were taken into
account.
Primary tests for fungicide activity were performed
by inoculation of a dense nutrient medium with
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13C NMR SPECTRA AND BIOLOGICAL ACTIVITY
1659
phytopathogenic fungi in the presence of a compound
to be tested. All compounds were tested as a concen-
tration of 0.003%. To ensure uniform distribution over
the substrate, compounds were preliminarily dissolved
in acetone (1:150) or thoroughly powdered. Potato
glucose agar was used as nutrient medium. Com-
pounds to be tested were added to the substrate before
its congelation (at 45 50 C), and the medium was
transferred onto Petri dishes in a volume of 15 cm3.
Fusarium culmorum and Helminthosporium sativum
mycelia were sown into each Petri dish at three sites
simultaneously. In a blank sample, were sown into
the same nutrient medium containing no fungicide.
Samples were incubated for 72 h at 25 26 C, and
average diameters of the fungi colonies were mea-
sured. Carbendazim (I) (a 30% suspension) was tested
under the same conditions for comparison. The
fungicide activity was calculated by the known
formula [29].
12. FRG Patent no. 2348120, 1975; Ref. Zh., Khim., 1975,
no. 24O111P.
13. FRG Patent no. 2164690, 1973; Ref. Zh., Khim., 1974,
no. 18N389P.
14. Khokhlov, P.S., Sokolova, G.D, Burmakin, N.M., and
Zhemchuzhin, S.G., Khim. Geterotsikl. Soedin., 1974,
no. 11, p. 1547.
15. US Patent no. 3929823, 1975; Ref. Zh., Khim., 1976,
no. 20O119P.
16. US Patent no. 3929824, 1975; Ref. Zh., Khim., 1976,
no. 21O100P.
17. US Patent no. 3915986, 1975; Ref. Zh., Khim., 1976,
no. 16O100P.
18. FRG Patent no. 2441201, 1976; Ref. Zh., Khim., 1976,
no. 21O105P.
19. FRG Patent no. 2441202, 1976; Ref. Zh., Khim., 1976,
no. 21O106P.
20. US Patent no. 4076825, 1978; Ref. Zh., Khim., 1987,
REFERENCES
no. 20O139P.
21. Ireland Patent no. 37855, 1977; Ref. Zh., Khim., 1978,
1. Pilyugin, V.S., Sintez i biologicheskaya aktivnost’
proizvodnykh 2-aminobenzimidazola (Synthesis and
Biological Activity of 2-Aminobenzimidazole Deri-
vatives), Moscow: Khimiya, 2003.
no. 18O108P.
22. US Patent no. 4046908, 1981; Ref. Zh., Khim., 1978,
no. 9O191P.
2. Bessonov, A.S., Veterinariya, 1990, no. 4, p. 3.
23. US Patent no. 4138493, 1979; Ref. Zh., Khim., 1979,
no. 19O133P.
3. Mel’nikov, N.N., Novozhilov, K.V., and Belan, S.R.,
Pestitsidy i regulyatory rosta rastenii. Spravochnik
(Pesticides and Plant Growth Regulators. Reference
Book), Moscow: Khimiya, 1995.
24. Burton, D., N’yubold, G., Persivall, A., Lemti, A., and
Sepsnol, A., USSR Inventor’s Certificate no. 249315,
1967; Byull. Izobret., 1969, no. 24.
4. Systemic Fungicides, Marsh, R.W., Byrde, R.J.W.,
25. Sweden Patent no. 490010, 1970; Ref. Zh., Khim.,
and Woodcock, D., Eds., New York: Wiley, 1972.
1971, no. 4N726.
5. Heterocyclic Compounds, Elderfield, R.C., Ed., New
York: Wiley, 1957, vol. 5. Translated under the title
Geterotsiklicheskie soedineniya, Moscow: Inostran-
naya Literatura, 1961, vol. 5, p. 211.
26. Pilyugin, V.S., Sapozhnikov, Yu.E., and Sapozhni-
kova, N.A., Russ. J. Gen. Chem., 2004, vol. 74, no. 5,
p. 738.
27. Lopyrev, V.A., Larina, L.I., Vakulskaja, T.A., La-
rin, M.F., Nefedova, O.B., Shibanova, E.F., and Vo-
ronkov, M.G., Org. Magn. Reson., 1981, vol. 15,
no. 3, p. 219.
6. Pozharskii, A.F., Granovskii, A.D., and Simo-
nov, A.M., Usp. Khim., 1966, vol. 35, no. 2, p. 261.
7. Katritzky, A. and Yates, F., J. Chem. Soc., Perkin.
Trans. 1, 1976, no. 3, p. 309.
28. Lopyrev, V.A., Larina, L.I., Vakulskaja, T.A., Shi-
banova, E.F., Titova, I.A., Voronkov, M.G., and
Liepinsh, E.E., Org. Magn. Reson., 1982, vol. 20,
no. 4, p. 212.
8. Simonov, A.M. and Anisimova, V.A., Khim. Getero-
tsikl. Soedin., 1979, no. 7, p. 867.
9. Rastogi, R. and Sharma, S., Int. J. Meth. Synth. Org.
Chem., 1983, no. 11, p. 861.
29. Metodicheskie rekomendatsii po ispytaniyu khimi-
cheskikh veshchestv na fungitsidnuyu aktivnost’
(Recommendations for Testing of Chemical Sub-
stances for Fungicide Activity), Cherkassy:
NIITEKhIM, 1990, p. 5.
10. Mishra, L., Singh, V. and Dubey, N., Biosci. Biotech.
Biochem., 1993, vol. 57, no. 6, p. 989.
11. US Patent no. 3480641, 1969; Ref. Zh., Khim., 1971,
no. 1N377P.
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