A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents

Abstract

A series of aryldifluoromethyl pyrimidine compounds containing strobilurin were synthesized through bioelectronic isometric design with azoxystrobin as the lead compound and a convenient approach to aryldifluoromethylpyrimidine intermediates was developed, which features mild reaction conditions and simple operation. The title compounds and aryldifluoromethylpyrimidine intermediates were characterized by NMR and HRMS. Both 7c and 7l of the preliminary screening tests showed 100% inhibition against Mythimna separata at 100 mg/L. At 20 mg/L, the lethal rate of 7l against Mythimna separata can be up to 80%.

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc1 Inhibitors for Novel Pesticide Discovery

“…The lead compound 24 not only showed good fungicidal activity against E. graminis but also exhibited significant insecticidal activity against Aphis fabae with LC 50 value of 6.4 μg/mL, which was much better than that of chlorfenapyr (19.4 μg/mL) and close to that of imidacloprid (4.8 μg/mL) . Compound 79 containing an aryldifluoromethyl pyrimidine as side chain could effectively inhibit M. separata at 20 mg/L with lethal rate of 80%, although it was a little less potent than insecticide abamectin (100%) …”

“…11 Compound 79 containing an aryldifluoromethyl pyrimidine as side chain could effectively inhibit M. separata at 20 mg/L with lethal rate of 80%, although it was a little less potent than insecticide abamectin (100%). 12 The structures of lead compounds 58, 24 and 79 are shown in Figure 12.…”

“…β-Methoxyacrylate derivatives bind the Qo site of cytochrome bc 1 and block electron transfer between cytochrome b and cytochrome c , which prevents oxidation of NADH and synthesis of ATP, resulting in the inhibition of energy production and thus leading to fungal death (Figure ). On the other hand, as the mitochondrial respiratory chain also widely exists in eukaryotes, the research extends to other types of pesticides, such as acaricides, , insecticides, − and herbicides, − and, drugs such as antitumor, − antimalarial, − and antimicrobial agents. , In addition, some β-methoxyacrylate derivatives could even be used as antiviral agents against plant viruses. − …”

Synthesis of potent antifungal 3,4-dichloroisothiazole-based strobilurins with both direct fungicidal activity and systemic acquired resistance

“…Therefore, the design of structurally diverse fungicides was essential for overcoming its resistance by many agrochemical companies and research institutes. [9][10][11][12] Plant elicitors, as a new type of green pesticide, show no or weak fungicidal activity in vitro and act by activating the plant's systemic acquired resistance against plant disease, which are classified by the FRAC according to their mode of action (MoA) as host plant defence induction. [13][14][15] Plant elicitors related to SA pathway are the main types of host plant defence fungicides including thiadiazole and isothiazole-containing heterocycles, such as isotianil, tiadinil and probenazole.…”

“…Therefore, the design of structurally diverse fungicides was essential for overcoming its resistance by many agrochemical companies and research institutes. 9–12…”