Synthesis and Fungicidal Activities of 2,3-Dimethyl-4-(1-acyloxy)alkoxy-6-tert-butyl-8-fluoroquinolines

Article abstract of DOI:10.1002/jhet.3515

A series of 2,3-dimethyl-4-(1-acyloxy)alkoxy-6-tert-butyl-8-fluoroquinolines were synthesized by 4-(tert-butyl)aniline as the starting material via acylation, substitution, and hydrolysis, and their structures were characterized by ¹H NMR,

Full text of DOI:10.1002/jhet.3515

Month 2019 Synthesis and Fungicidal Activities of 2,3-Dimethyl-4-(1-acyloxy)alkoxy-
6-tert-butyl-8-fluoroquinolines
a
Dan Pei,a Fan Zhang,a Jie Liu,a Dong-Lin Zhang,a Ren Yang,a Liang-Kun Zhong,a,b Cheng-Xia Tan,
and
*
b
*
Tian-Ming Xu
aCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
bSinochem Lantian Zhejiang Research Institute of Chemical Industry Co. Ltd., Hangzhou 310023, China
*E-mail: tanchengxia@zjut.edu.cn; xutianming@sinochem.com
Received July 11, 2018
DOI 10.1002/jhet.3515
Published online 00 Month 2019 in Wiley Online Library (wileyonlinelibrary.com).
A series of 2,3-dimethyl-4-(1-acyloxy)alkoxy-6-tert-butyl-8-fluoroquinolines were synthesized by 4-(tert-
butyl)aniline as the starting material via acylation, substitution, and hydrolysis, and their structures were
1
characterized by H NMR, 13C NMR, and HRMS. The fungicidal activity showed that compounds 6c, 6e,
and 6f had excellent activity against Sphoaerotheca fuliginea with EC50 values of 38.62, 6.77, and
50.35 mg/L, respectively. The results suggest that this chemotype of compounds warrant further studies as
promising fungicide.
J. Heterocyclic Chem., 00, 00 (2019).
INTRODUCTION
an active intermediate and possess excellent activity
(93%) against rice blast at 3 mg/L [23]. In our previous
work [13–15], a series of quinoline compounds were
designed and synthesized; the bioassay results indicated
that the quinoline compounds containing fluorine atom
showed better fungicidal activity than other halo
atom. Hence, a series of 2,3-dimethyl-4-(1-alkyl acetoxy)-
6-tert-butyl-8-fluoroquinolines were designed, and their
fungicidal activities were evaluated.
Heterocyclic compounds have become the mainstream of
new pesticide research due to their wide range of biological
activities, low toxicity, high efficiency, environmental
friendliness, and structural diversity [1–3]. Heterocyclic
agrochemicals containing nitrogen has better activity,
including insecticidal [4,5], antimicrobial [6], antiviral [7],
fungicidal [8–11], and herbicidal [12]. Quinolines are one
of the most important compounds in nitrogen-containing
heterocycles and exhibited appreciable fungicidal activity
[13–15]. For example, Quioxyfen is an effective anti-
powdery mildew agent. Quinoline compounds are more
important for discovery new pesticidal lead compounds.
In recent years, several compounds containing quinoline
structures have been put on the market as commercial
pesticide, and pesticidal chemists still discover novel
pesticides with high effective and low toxic [16].
The fluorine atom with a small radius and strong
electronegativity has simulation, electronic, blocking, and
penetration effects. Fluorine atom is frequently
introduced into heterocycles, which increase their
biological activity [17–21]. For example, Tebufloquin
[22] is a novel fungicide that provides outstanding
control effective against rice blast, which exhibited better
activity after introducing fluorine atom into quinoline
ring. Actually, the metabolite of Tebufloquin, 6-tert-butyl-
8-fluoro-2,3-dimethyl-4(1H)-quinolinone (M1, Fig. 1) is
RESULTS AND DISCUSSION
Chemistry.
The detailed synthetic route for the
preparation of synthesis of 2,3-dimethyl-4-(1-alkyl
acetoxy)-6-tert-butyl-8-fluoroquinolines is summarized in
Scheme 1. Starting from 4-(tert-butyl)aniline, the key
intermediate 6-(tert-butyl)-8-fluoro-2,3-dimethylquinolin-
4-ol 5 [24–27] was synthesized in four steps including
acylation, substitution, hydrolysis, and cyclization
reaction. Subsequently, the 6-(tert-butyl)-8-fluoro-2,3-
dimethylquinolin-4-ol 5 and 1-chloroalkyl acylate were
converted into their corresponding new compounds
6a–6g by elimination reaction, using sodium carbonate as
the acid scavenger and sodium iodide as the catalyst. All
1
the structures were characterized by H NMR, 13C NMR,
and HRMS. In the 13C NMR spectra, the chemical shift
at 177.4–169.4 ppm confirmed the existence of C═O.
© 2019 Wiley Periodicals, Inc.

D. Pei, F. Zhang, J. Liu, D.-L. Zhang, R. Yang, L.-K. Zhong, C.-X. Tan, and T.-M. Xu
Vol 000
Among all the compounds, compounds 6c, 6e, and 6f
exhibited excellent fungicidal activity with the inhibition
rates of 100%, 100%, and 90% at the concentration of
200 mg/L. Furthermore, compound 6c showed 10%
fungicidal activity against B. cinerea.
Figure 1. Tebufloquin
Preliminary biology results were listed in Table 2
and indicated that compounds 6e and 6f exhibited
comprehensive fungicidal activities against S. fuliginea
with the high inhibition rates of 92.59% and 96.30% at
the concentration of 50 mg/L, respectively. Given the
aforementioned results, this kind of compounds could be
further investigated as promising fungicides.
Based on the preliminary bioassays, the EC50 values of
compounds 6c, 6e, and 6f as well as Tebuconazole
were summarized in Table 2. Notably, compounds
6c and 6f exhibited low fungicidal activities against
S. fuliginea, with EC50 values of 38.62 and 50.35 mg/L,
Fungicidal activity. Poison plate technique was used to
examine the fungicidal activity of the target compounds
(6a–6g) against four fungi (Sphoaerotheca fuliginea,
Pseudoperonospora
cubensis,
Botrytis
cinerea,
and Rhizoctonia lsolani). While Tebuconazole was
chosen as the control agent for the bioactivity.
The fungicidal activity results of all target compounds
are listed in Table 1. The bioassays indicated that several
target compounds showed certain inhibition bioactivity
against S. fuliginea in the dosage of 200 mg/L (Table 1).
Scheme 1. The synthetic route of compounds 6a–6g.
Table 1
The test of bactericidal activity.
Inhibition rate (%)
Concentration
Sphoaerotheca
fuliginea
Pseudoperonospora
cubensis
Botrytis
cinerea
Rhizoctonia
solani
Compound
R1
R2
(mg/L)
6a
6b
6c
CH3
H
H
─CH3
─C(CH3)2CH2CH3
200
200
200
0
0
100
0
0
0
0
0
10
0
0
0
6d
6e
6f
CH3 ─C(CH3)2CH2CH3
200
200
200
0
100
90
0
0
0
0
0
0
0
0
0
H
─C(CH3)3
H
6g
H
─CH(CH3)2
200
30
0
0
0
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DOI 10.1002/jhet

Month 2019
Fluorinated Quinolines with Antifungal Activity
Table 2
Powdery mildew rescreening results of compounds 6c, 6e, and 6f.
Concentration
(mg/L)
Regression equation
(A + BX)
Confidence interval
Compound
Inhibition (%)
R
EC50 (mg/L)
38.62
(mg/L)
6c
50
25
12.5
6.25
3.125
50
66.67
22.22
7.41
0
À0.1606 + 3.2521X
0.98
33.7093–46.4850
0
6e
92.59
77.78
66.67
44.45
33.33
96.30
87.04
59.26
7.41
0
87.04
51.85
25.92
11.12
0
3.7455 + 1.5108X
À1.2606 + 3.6784X
1.5845 + 2.5762X
0.99
0.97
0.98
6.77
50.35
21.17
5.2516–8.2796
25
12.5
6.25
3.125
200
100
50
25
12.5
50
6f
35.4736–63.5773
18.6731–24.2994
Tebuconazole
25
12.5
6.25
3.125
respectively. Moreover, compound 6e showed excellent
fungicidal activity against S. fuliginea, with EC50 value
of 6.77, which were better than that of Tebuconazole
(21.17).
EXPERIMENTAL
Instruments.
Melting points were determined by an
1
X-4 apparatus and uncorrected. H NMR and 13C NMR
spectra were measured on a Bruker AV-400 or 600
instrument (Bruker, Switzerland) by using tetramethylsilane
as an internal standard and CDCl3 as the solvent. Mass
spectra were determined on an LCQ Advantage LC/mass
detector instrument (Thermo Fisher, Waltham, MA).
All the reagents are analytical grade or freshly prepared.
As an extension of this approach, it was found that
the type of R1-substituted groups has significant effect
on fungicidal activities of the target compounds.
When R1 is H, the corresponding compounds exhibited
excellent fungicidal activities against S. fuliginea. On
the other hand, when R1 is CH3, the corresponding
title compounds exhibited low fungicidal activities
against S. fuliginea. Interestingly, it was noted that
when R1 is CH3, the corresponding compound also
showed unsatisfactory fungicidal activities against
B. cinerea.
General
procedure. N-(4-(tert-Butyl)phenyl)acetamide
To a solution of 4-(tert-butyl)aniline (100 g,
2.
0.67 mol) in dichloromethane (100 mL), acetic anhydride
(70 mL, 0.75 mmol) was added dropwise at room
temperature. Thin-layer chromatography (TLC) was used
for monitoring. After the reaction was completed, the
mixture was poured into water, which gave substantial
CONCLUSION
amount of solids. After being dried at 259–261°C, 70 g
of solid resulted, indicating a yield of 54.7%.
In summary, eight novel compounds were obtained after
acylation, substitution, and hydrolysis with 4-(tert-butyl)
aniline as raw material. All compounds were
N-(4-(tert-Butyl)-2-fluorophenyl)acetamide 3. Selectfluor
were (120.7 g, 340.6 mmol) dissolved in acetonitrile
(400 mL), then N-(4-(tert-butyl)phenyl)acetamide (50 g,
261 mmol) was added. The mixture was heated to reflux.
TLC was used for monitoring. After the reaction was
completed, the reaction mixture was poured into water, then
extracted with ethyl acetate; the organic layer was washed
with brine and dried over MgSO4; the mixture was filtered
and evaporated, yielding a yellow solid (30.07 g, 55.6%).
1
characterized by H NMR, 13C NMR, and HRMS, and
the fungicidal activities of the target compounds were
tested. The bioassay results revealed that the compounds
6c, 6e, and 6f exhibited high activity against cucumber
powdery mildew with the inhibition rates of 100%,
100%, and 90% at the concentration of 200 mg/L,
respectively. The results indicated that this kind of
structures could be further studied to improve the
fungicidal activity.
6-(tert-Butyl)-8-fluoro-2,3-dimethylquinolin-4-ol 5.
In a
250 mL three neck bottom flask, the 4-(tert-butyl)-2-
fluoroaniline (13 g, 72 mmol), ethyl 2-methyl-3-
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

D. Pei, F. Zhang, J. Liu, D.-L. Zhang, R. Yang, L.-K. Zhong, C.-X. Tan, and T.-M. Xu
Vol 000
oxobutanoate (10.3 g, 72 mmol) and polyphosphoric acid
(30 g) was stirred at 150°C. TLC was used to monitor the
reaction. After the reaction was completed, the mixture
was poured into water, which gave substantial amount of
solids; 16.2 g of solid resulted, indicating a yield of 91.1%.
1.80 (d, 3H, J = 6 Hz, CHCH3), 1.48 (s, 2H, CH2CH3),
1.41 (s, 9H, C(CH3)3), 0.90 (s, 3H, C(CH3)2), 0.84 (s, 3H,
C(CH3)2), 0.41 (t, 3H, J = 6 Hz, CH2CH3); 13C NMR
(CDCl3, 150 MHz) δ: 176.6, 160.2, 148.5, 124.4, 122.5,
112.7, 111.9, 111.8, 111.2, 97.1, 42.6, 352, 32.9, 31.0,
24.9, 24.3, 24.1, 20.8, 13.1, 9.5, 8.7; HRMS Calcd for
General procedure for preparation of compounds 6a to 6g.
To a solution of 6-(tert-butyl)-2,3,8-trimethylquinolin-4-ol
(0.3 g, 1.2 mmol), Na2CO3 (0.18 g, 1.7 mmol), and NaI
(0.02 g, 0.12 mmol) in acetonitrile (25 mL), the
1-chloroalkyl acylate (1.3 mmol) was added dropwise. The
reaction was monitored by TLC. After the reaction was
completed, the mixture was filtered and evaporated. The
target compound was purified by chromatography on a
silica gel using petroleum ether and ethyl acetate (V (PE):
V (EA) = 6:1) as the eluent to afford compounds 6a to 6g.
The physical data of these compounds are as follows.
C23H33FNO3 [M + H]+ 390.2366, found 390.2452.
((6-(tert-Butyl)-8-fluoro-2,3-dimethylquinolin-4-yl)oxy)
methylpivalate (6e). White solid; mp 64–65°C; yield 92%;
1H NMR (CDCl3, 600 MHz) δ: 7.68 (s, 1H, Ph─H), 7.42
(d, 1H, J = 13.2 Hz, Ph─H), 5.82 (s, 2H, OCH2), 2.72
(s, 3H, Ph─CH3), 2.41 (s, 3H, Ph─CH3), 1.40 (s, 9H,
C(CH3)3), 1.11 (s, 9H, OC(CH3)3); 13C NMR (CDCl3,
150 MHz) δ: 177.4, 160.3, 158.3, 157.2, 157.2, 156.6,
149.1, 149.1, 136.2, 136.1, 123.8, 123.8, 122.2, 112.2,
112.2, 112.0, 111.9, 89.4, 38.78, 35.3, 31.1, 26.9, 24.3,
13.1; HRMS Calcd for C21H29FNO3 [M + H]+ 362.2053,
((6-(tert-Butyl)-8-fluoro-2,3-dimethylquinolin-4-yl)oxy)
found 362.2136.
((6-(tert-Butyl)-8-fluoro-2,3-dimethylquinolin-4-yl)oxy)
ethylacetate (6a). Yellow oily liquid; yield 80%; 1H NMR
(CDCl3, 600 MHz) δ: 7.75 (s, 1H, Ph─H), 7.42 (t, 1H,
J = 13.2 Hz, Ph─H), 6.38 (q, J = 5.4 Hz, 1H, CH), 2.71 (s,
3H, Ph─CH3), 2.40 (s, 3H, Ph─CH3), 1.82 (s, 3H, OCH3),
1.81 (d, 3H, J = 5.4 Hz, CHCH3), 1.41 (s, 9H, C(CH3)3);
13C NMR (CDCl3, 150 MHz) δ: 169.4, 160.3, 158.2,
156.8, 156.5, 148.8, 148.7, 136.2, 122.7, 112.6, 111.8,
111.7, 111.1, 97.0, 35.2, 31.2, 24.3, 20.8, 12.9; HRMS
Calcd for C19H25FNO3[M + H]+ 334.174, found 334.1811.
((6-(tert-Butyl)-8-fluoro-2,3-dimethylquinolin-4-yl)oxy)
methylcyclopropanecarboxylate (6f).
Yellow solid; mp
1
57–58°C; yield 82%; H NMR (CDCl3, 600 MHz) δ: 7.69
(s, 1H, Ph─H), 7.43 (d, 1H, J = 13.2 Hz, Ph─H), 5.77
(s, 2H, CH2), 2.72 (s, 3H, Ph─CH3), 2.39 (s, 3H,
Ph─CH3), 1.58 (t, 1H, J = 6 Hz, CH), 1.40 (s, 9H,
C(CH3)3), 0.94 (s, 2H, CHCH2), 0.87 (d, 2H, CHCH2);
13C NMR (CDCl3, 150 MHz) δ: 173.9, 160.3, 158.3,
157.5, 157.4, 156.6, 149.2, 149.1, 136.2, 136.1, 123.9,
123.9, 122.4, 112.3, 112.2, 112.0, 111.8, 88.8, 35.2, 31.1,
24.3, 12.9, 12.8, 9.1; HRMS Calcd for C20H25FNO3
methyl 2,2-dimethylbutanoate (6b).
White solid; mp
1
54–55°C; yield 85%; H NMR (CDCl3, 600 MHz) δ: 7.70
(s, 1H, Ph─H), 7.42 (d, 1H, J = 12.6 Hz, Ph─H), 5.82 (s,
2H, OCH2), 2.72 (s, 3H, Ph─CH3), 2.41 (s, 3H, Ph─CH3),
1.47 (q, 2H, J = 12 Hz, CH2CH3), 1.40 (s, 9H, C(CH3)3),
1.07 (s, 6H, C(CH3)2), 0.69 (t, 3H, J = 12 Hz, CH2CH3);
13C NMR (CDCl3, 150 MHz) δ: 176.9, 160.3, 158.3,
157.1, 156.6, 149.1, 149.0, 136.2, 123.8, 122.3, 112.3,
112.0, 111.9, 42.7, 35.3, 33.0, 31.1, 24.3, 13.1, 9.0; HRMS
Calcd for C22H31FNO3[M + H]+ 376.2210, found 376.2289.
((6-(tert-Butyl)-8-fluoro-2,3-dimethylquinolin-4-yl)oxy)
[M + H]+ 346.1740, found 346.1818.
((6-(tert-Butyl)-8-fluoro-2,3-dimethylquinolin-4-yl)oxy)
methylisobutyrate (6g).
White solid; mp 57–58°C; yield
1
80%; H NMR (CDCl3, 600 MHz) δ: 7.69 (s, 1H, Ph─H),
7.42 (d, 1H, J = 12.6 Hz, Ph─H), 5.80 (s, 2H, CH2), 2.72
(s, 3H, Ph─CH3), 2.50 (q, 1H, J = 6 Hz, CH), 2.40 (s, 3H,
Ph─CH3), 1.40 (s, 9H, C(CH3)3), 1.09 (s, 3H, CHCH3),
1.08 (s, 3H, CHCH3); 13C NMR (CDCl3, 150 MHz) δ:
175.9, 160.3, 158.3, 157.3, 157.2, 156.6, 149.1, 149.1,
136.2, 136.1, 123.9, 123.8, 122.3, 112.3, 112.2, 112.0,
111.9, 89.1, 35.2, 33.9, 31.1, 24.3, 18.6, 13.0; HRMS
Calcd for C20H27FNO3 [M + H]+ 348.1897, found 348.1977.
methylcyclohexanecarboxylate (6c).
White solid; mp
1
55–58°C; yield 77%; H NMR (CDCl3, 600 MHz) δ: 7.69
(s, 1H, Ph─H), 7.42 (d, 1H, J = 13.2 Hz, Ph─H), 5.80
(s, 2H, OCH2), 2.72 (s, 3H, Ph─CH3), 2.39 (s, 3H,
Ph─CH3), 2.23 (t, 1H, J = 12 Hz, CH), 1.78 (m, 6H,
CH(CH2)5), 1.40 (s, 9H, C(CH3)3), 1.31 (m, 2H,
CH(CH2)5), 1.20 (m, 2H, CH(CH2)5); 13C NMR (CDCl3,
150 MHz) δ: 174.8, 160.3, 158.3, 157.3, 157.3, 156.6,
149.1, 149.0, 136.2, 122.3, 112.3, 112.3, 112.0, 111.9,
89.0, 43.0, 35.2, 31.1, 28.7, 25.6, 25.3, 24.3, 13.0; HRMS
Calcd for C23H31FNO3[M + H]+ 388.2210, found 388.2290.
Acknowledgments. This work was supported financially by the
Zhejiang University of Technology. Thanks to Dr. Li Xingcong
from the University of Mississippi for his guidance.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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Fluorinated Quinolines with Antifungal Activity
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Additional supporting information may be found online
in the Supporting Information section at the end of the
article.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet