Design, Synthesis and Fungicidal Activities of Pyridyl Oxazoamide Compounds

doi:10.6023/cjoc202007009

Abstract

Thirteen novel pyridyl oxazoamide compounds were synthesized using pyridine-2-formaldehyde as the starting material through cyclization, oxidation, substitution, hydrolysis, chlorination and ammonolysis reactions via the disclosed intermediate derivatization method (IDM). The structures of title compounds were characterized by ¹H NMR and HRMS. Preliminary bioassay results indicated that at 100 mg/L, 7 compounds exhibited 100% fungicidal activities against Botrytis cinerea, and N-(4-fluorophenyl)-2-(pyridin-2-yl)oxazole-4-carboxamide (7b) exhibited 100% fungicidal activities against Rhizoctonia solani. Further fungicidal activity test results suggested that some of the target compounds had better fungicidal activity than azoxystrobin, which was worthy of further study.

Key words: oxazole, amide, pyridine, fungicide activity

Cite this article

Shu Chen, Chaoli Ren, Xiaoyu Tian, Donglin Zhang, Sen Yang, Shaoqing Yuan, Xiaohua Du, Chengxia Tan. Design, Synthesis and Fungicidal Activities of Pyridyl Oxazoamide Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 842-848.

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Entry	Oxidant	Yield/%
1	K₂S₂O₈/H₂SO₄	24
2	H₂O₂/H₂SO₄	12
3	CCl₃Br/DBU	68

Entry	Oxidant	Yield/%
1	K₂S₂O₈/H₂SO₄	24
2	H₂O₂/H₂SO₄	12
3	CCl₃Br/DBU	68

Compd.	R	黄瓜灰霉病菌 (B. cinerea)	水稻纹枯病菌 (R. solani)
7a	2-F	100	90
7b	4-F	100	100
7c	2,4-F₂	100	80
7d	2,6-F₂	100	80
7e	3-Cl	100	90
7f	3,5-Cl₂	85	60
7g	3-Cl-2-CH₃	90	80
7h	3-Br	90	80
7i	3-CF₃	90	80
7j	4-CH₃	100	70
7k	2,4-(CH₃)₂	100	90
7l	4-OC₂H₅	90	80
7m	4-tert-C₄H₉	90	70
嘧菌酯		100	100

Compd.	R	黄瓜灰霉病菌 (B. cinerea)	水稻纹枯病菌 (R. solani)
7a	2-F	100	90
7b	4-F	100	100
7c	2,4-F₂	100	80
7d	2,6-F₂	100	80
7e	3-Cl	100	90
7f	3,5-Cl₂	85	60
7g	3-Cl-2-CH₃	90	80
7h	3-Br	90	80
7i	3-CF₃	90	80
7j	4-CH₃	100	70
7k	2,4-(CH₃)₂	100	90
7l	4-OC₂H₅	90	80
7m	4-tert-C₄H₉	90	70
嘧菌酯		100	100

Compd.	黄瓜灰霉病菌(B. cinerea)			水稻纹枯病菌(R. solani)
Compd.	50 mg?L^–1	25 mg?L^–1	12.5 mg?L^–1	50 mg?L^–1	25 mg?L^–1	12.5 mg?L^–1
7a	45.88	12.36	—	47.06	29.31	17.69
7b	52.06	41.18	30.08	51.77	41.71	31.77
7c	63.83	40.30	29.71	79.12	18.24	16.77
7d	62.06	49.41	32.94	50.00	42.06	20.06
7e	66.47	14.71	—	57.90	18.83	11.77
7f	42.06	14.41	6.77	—	—	—
7g	65.00	44.71	17.36	66.77	36.77	6.18
7h	50.59	11.76	0.88	68.83	8.82	1.47
7i	51.77	27.06	24.12	—	—	—
7j	41.76	7.65	3.83	—	—	—
7k	64.41	28.83	7.06	55.30	34.41	4.41
7l	67.35	38.21	29.71	49.12	25.30	19.12
7m	47.65	30.30	9.71	—	—	—
嘧菌酯	40	20	0	60	20	0

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