Design and Synthesis of 1,2,4-Oxadiazine Derivatives as Promising Fungicide and Insecticide Lead Compound

doi:10.6023/cjoc202101029

Abstract

Oxadiazine is an active fragment and usually is used for modification and conformation restriction of small molecules, meanwhile, it can be considered as an ideal and completely competent surrogate for the amide group. Based on the general framework of marketed succinate dehydrogenase inhibitors, twenty-four 1,2,4-oxadiazine compounds were designed and synthesized. The bioactivity test results showed that most of compounds exhibited good activities against Pseudoperonospora cubensis at 400 mg/L. In addition, the oxadiazine compounds have a 100% mortality against armyworms at 600 mg/L, which illustrates that oxadiazine structure is worth to be a lead compound and further modification to discover novel active with practical potentials.

Key words: oxadiazine, synthesis, bioisosterism, biological activities

Cite this article

Letian Zhang, Jiayuan Su, Xiaoyong Xu. Design and Synthesis of 1,2,4-Oxadiazine Derivatives as Promising Fungicide and Insecticide Lead Compound[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3539-3549.

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Compd.	R¹	R²	Inhibitory rate/%
Compd.	R¹	R²	P.C.^a	B.G.^a	P.S.^a	C.O ^a	P.O.^b	B.C.^b
A1	H	H	85	0	0	0	0	0
A5	H	4-CF₃	78	0	0	0	0	0
A6	H	4-OCF₃	90	0	0	30	50	0
A7	H	3-CH₃	85	0	0	0	0	0
A11	H	3-NO₂- 4-CH₃	98	0	0	0	50	0
CK	—	—	0	0	0	0	0	0
Mancozeb	—	—	100	—	—	—	—	—
Azoxystrobin	—	—	—	100	100	100	100	—
Pyrisoxazole	—	—	—	—	—	—	—	100

Compd.	R¹	R²	Inhibitory rate/%
Compd.	R¹	R²	P.C.^a	B.G.^a	P.S.^a	C.O ^a	P.O.^b	B.C.^b
A1	H	H	85	0	0	0	0	0
A5	H	4-CF₃	78	0	0	0	0	0
A6	H	4-OCF₃	90	0	0	30	50	0
A7	H	3-CH₃	85	0	0	0	0	0
A11	H	3-NO₂- 4-CH₃	98	0	0	0	50	0
CK	—	—	0	0	0	0	0	0
Mancozeb	—	—	100	—	—	—	—	—
Azoxystrobin	—	—	—	100	100	100	100	—
Pyrisoxazole	—	—	—	—	—	—	—	100

Compd.	R¹	R²	Inhibitory rate/%
Compd.	R¹	R²	100 mg/L	25 mg/L
A1	H	H	10	10
A2	H	2-F	30	0
A3	H	3-Br	0	0
A4	H	4-NO₂	10	0
A5	H	4-CF₃	0	0
A6	H	4-OCF₃	10	0
A7	H	3-CH₃	10	10
A8	H	4-CH₃	10	0
A9	H	4-OCH₃	20	0
A10	H	4-OPh	10	0
A11	H	3-NO₂-4-CH₃	20	0
A12	4-Cl	H	0	0
A13	4-Cl	2-F	0	0
A14	4-Cl	4-F	0	0
A15	4-Cl	3-Br	0	0
A16	4-Cl	3-CH₃	10	0
A17	4-Cl	4-CH₃	0	0
A18	4-Cl	3-NO₂-4-CH₃	0	0
A19	4-CH₃	H	50	0
A20	4-CH₃	2-F	70	0
A21	4-CH₃	4-F	0	0
A22	4-CH₃	3-Br	20	0
A23	4-CH₃	3-CH₃	0	0
A24	4-CH₃	4-CH₃	50	0
CK	—	—	0	0
Cyazofamid	—	—	100	100
Fluopyram	—	—	0	0

Compd.	R¹	R²	Inhibitory rate/%
Compd.	R¹	R²	100 mg/L	25 mg/L
A1	H	H	10	10
A2	H	2-F	30	0
A3	H	3-Br	0	0
A4	H	4-NO₂	10	0
A5	H	4-CF₃	0	0
A6	H	4-OCF₃	10	0
A7	H	3-CH₃	10	10
A8	H	4-CH₃	10	0
A9	H	4-OCH₃	20	0
A10	H	4-OPh	10	0
A11	H	3-NO₂-4-CH₃	20	0
A12	4-Cl	H	0	0
A13	4-Cl	2-F	0	0
A14	4-Cl	4-F	0	0
A15	4-Cl	3-Br	0	0
A16	4-Cl	3-CH₃	10	0
A17	4-Cl	4-CH₃	0	0
A18	4-Cl	3-NO₂-4-CH₃	0	0
A19	4-CH₃	H	50	0
A20	4-CH₃	2-F	70	0
A21	4-CH₃	4-F	0	0
A22	4-CH₃	3-Br	20	0
A23	4-CH₃	3-CH₃	0	0
A24	4-CH₃	4-CH₃	50	0
CK	—	—	0	0
Cyazofamid	—	—	100	100
Fluopyram	—	—	0	0

作为杀菌和杀虫先导的1,2,4-噁二嗪衍生物的设计与合成研究