Synthesis of Thiochromone Formamide Derivatives and Their Antifungal Activities

doi:10.6023/cjoc202506027

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (1): 87-95.DOI: 10.6023/cjoc202506027 Previous Articles Next Articles

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硫色酮甲酰胺衍生物的合成及其抑菌活性

周蒲^a, 苏子洋^a, 崔得运^b, 程绎南^a^,^*(), 李毅^a, 周海峰^a, 孙炳剑^a, 李洪连^a

^a 河南农业大学植保学院郑州 450046
^b 河南省科学院高新技术研究中心郑州 450002

收稿日期:2025-06-20 修回日期:2025-08-18 发布日期:2025-09-23
通讯作者: 程绎南
基金资助:
河南省重点研发专项(251111111600); 河南省高等学校重点科研计划(25A210014); 以及河南省科学院高层次人才科研启动(241802037)

Synthesis of Thiochromone Formamide Derivatives and Their Antifungal Activities

Zhou Pu^a, Su Ziyang^a, Cui Deyun^b, Cheng Yi-Nan^a^,^*(), Li Yi^a, Zhou Haifeng^a, Sun Bingjian^a, Li Honglian^a

^a Plant Protection College, Henan Agricultural University, Zhengzhou 450046
^b High & New Technology Research Center of Henan Academy of Sciences, Zhengzhou 450002

Received:2025-06-20 Revised:2025-08-18 Published:2025-09-23
Contact: Cheng Yi-Nan
Supported by:
Key R&D Special Project of Henan Province(251111111600); Key Research Project Plan for Higher Education Institutions in Henan Province(25A210014); High-Level Talent Research Start-Up Project Funding of Henan Academy of Sciences(241802037)

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Abstract

13 new thiochromone formamide derivatives substituted at position 2 were synthesized and two synthetic routes for these compounds were developed using 1-(2-chlorophenyl)ethanone and 2-mercaptobenzoic acid as materials, respectively. Their antifungal activities against Gaeumannomyces graminis var. tritici were evaluated in vitro by the plate method. The results of structure-activity relationship indicated that the group at position 2 of thiochromone formamide derivatives had an important influence on their antifungal activities against Gaeumannomyces graminis var. tritici. 2-(4-Chlorophenylamino)- N,N-diethyl-4-oxo-4H-thiochromene-3-carboxamide (6f) showed a good activity. Its inhibitory rate reached up to 100% at 50 mg/L. Further results showed that the activity of isopropyl 4-(4-oxo-2-phenyl-4H-thiochromene-3-carboxamido)benzoate (13e) against Gaeumannomyces graminis var. tritici was excellent. Its inhibitory rate also reached up to 100% at 12.5 mg/L with a lower value of EC₅₀ (0.07 mg/L) than positive control Silthiopham (EC₅₀ 26.7 mg/L). The results will provide some help for design of new active compounds and development of new fungicides.

Key words: thiochromone formamide derivative, synthetic routes, Gaeumannomyces graminis var. tritici, inhibitory activity

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Zhou Pu, Su Ziyang, Cui Deyun, Cheng Yi-Nan, Li Yi, Zhou Haifeng, Sun Bingjian, Li Honglian. Synthesis of Thiochromone Formamide Derivatives and Their Antifungal Activities[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 87-95.

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Fig. & Tab. 7

References 9

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Entry	Base	T/℃	Time/h	Solvent	Yield/%
1	NaOH	130	8	DMF	13
2	NaOH	130	8	DMSO	15
3	NaOH	40	8	DMSO	35
4	NaH	130	8	DMSO	15
5	NaH	40	8	DMSO	57

Entry	Base	T/℃	Time/h	Solvent	Yield/%
1	NaOH	130	8	DMF	13
2	NaOH	130	8	DMSO	15
3	NaOH	40	8	DMSO	35
4	NaH	130	8	DMSO	15
5	NaH	40	8	DMSO	57

Entry	Promoter (1.6 equiv.)	Base (1 equiv.)	T/℃	Time/h	Solvent	Yield/%
1	—	K₂CO₃	r.t.	7	Toluene	0
2	PPh₃	—	r.t.	7	Toluene	Trace
3	PPh₃	C_S2CO₃	r.t.	7	Toluene	Trace
4	PPh₃	K₂CO₃	r.t.	7	Toluene	Trace
5	K₂CO₃	TMG	r.t.	7	Toluene	0
6	PPh₃	TMG	r.t.	7	Toluene	51
7	PPh₃	TMG	r.t.	7	DMF	Trace
8	PPh₃	TMG	r.t.	7	DMSO	Trace
9	PPh₃	TMG	50	7	Toluene	73
10	PPh₃	TMG	70	7	Toluene	57

Entry	Promoter (1.6 equiv.)	Base (1 equiv.)	T/℃	Time/h	Solvent	Yield/%
1	—	K₂CO₃	r.t.	7	Toluene	0
2	PPh₃	—	r.t.	7	Toluene	Trace
3	PPh₃	C_S2CO₃	r.t.	7	Toluene	Trace
4	PPh₃	K₂CO₃	r.t.	7	Toluene	Trace
5	K₂CO₃	TMG	r.t.	7	Toluene	0
6	PPh₃	TMG	r.t.	7	Toluene	51
7	PPh₃	TMG	r.t.	7	DMF	Trace
8	PPh₃	TMG	r.t.	7	DMSO	Trace
9	PPh₃	TMG	50	7	Toluene	73
10	PPh₃	TMG	70	7	Toluene	57

Compd.	Percent inhibition^a/% (in vitro)
Compd.	200 mg/L	100 mg/L	50 mg/L	25 mg/L	12.5 mg/L
6a	71.6	39.2	22.6	18.0	10.5
6b	87.0	80.9	67.3	50.4	41.3
6c	100	51.6	32.7	26.5	20.5
6d	99.1	62.9	39.8	20.7	3.8
6e	56.9	32.8	15.5	12.1	10.1
6f	100	100	100	70.6	29.2
6g	89.8	80.2	63.6	37.6	17.3
6h	97.4	90.8	88.6	86.6	57.6
13a	99.5	91.7	51.6	23.6	20.1
13b	58.3	44.9	28.9	23.3	17.5
13c	93.5	93.0	90.3	90.9	86.3
13d	98.6	93.0	87.0	87.8	80.6
13e	100	100	100	100	100
Silthiopham	100	92.3	66.7	40.5

硫色酮甲酰胺衍生物的合成及其抑菌活性

Synthesis of Thiochromone Formamide Derivatives and Their Antifungal Activities

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