Journal of Pesticide Science Vol. 42(2017) No. 2

The behavior of cyphenothrin (1) [(RS)-α-cyano-3-phenoxybenzyl (1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate] in an aquatic environment was investigated by using the ¹⁴C-labeled trans and cis isomers. In parallel with the rapid partition from water phase to bottom sediment, 1 was degraded with the first-order half-lives of 2.0 (trans-1) and 7.3 days (cis-1) in the water-sediment system under dark conditions. 1 underwent extensive microbial degradation via ester cleavage to form 3-phenoxybenzoic acid, finally forming bound residues and mineralizing to CO₂. Aqueous photolysis significantly accelerated the degradation of 1 with a half-life of <1 day, mainly via photo-induced oxidation at the 2-methylprop-1-enyl group and ester cleavage without cis-trans isomerization. These results strongly suggest that 1 is unlikely to persist in the actual aquatic environment due to its rapid photolysis and extensive microbial degradation.

The target site of tolprocarb has been reported to be polyketide synthase (PKS). Here, we evaluated the activities for Pyricularia oryzae PKS and melanin biosynthesis as well as the control efficacy of rice blast using a series of tolprocarb derivatives. A comparison of the inhibitory activities of PKS and melanin biosynthesis revealed a linear relationship (r²=0.90), confirming PKS as the target site of tolprocarb. A compound beyond this relationship was metabolized by P. oryzae to an inactive compound. The control efficacy of rice blast was explained using the melting point and either the inhibitory activity of PKS or melanin biosynthesis. Structure–activity analysis revealed that both end parts of tolprocarb preferred hydrophobic groups, and the chirality of the substituent in the middle part significantly influenced the activities. These relationships will provide useful information for the development of novel PKS inhibitors.

Maximum residue limits (MRLs) for pesticides in export countries from Japan often become a trade barrier for Japanese tea. The purpose of this study is to develop a probabilistic risk estimation method for pesticide residues in green tea. First, we developed a model to estimate the pesticide residue level in green tea. Second, we introduced a regression model for pesticide half-lives on plants, one of the most critical parameters in the model. Finally, we estimated the time-course change of the distribution of the residue level by setting the probability distribution to the half-lives on tea leaves. Applying the model to three pesticides, acetamiprid, dinotefuran, and thiamethoxam, we suggested that the pre-harvest interval of thiamethoxam should be increased by three weeks for export to Taiwan. For EU nations, the MRL excess probabilities of acetamiprid and dinotefuran were measured as 99.6% and 99.5%, respectively, even 28 days after spraying.

The voltammetric determination of metsulfuron-methyl, a type of pesticide, was investigated on a hanging mercury drop electrode using a differential pulse cathodic stripping voltammetry technique. The experimental parameters, such as the pH of the Britton–Robinson buffer, accumulation time, accumulation potential and initial potential were optimized for the metsulfuron-methyl determination. A well-defined reduction peak was observed at pH 2.0 to 4.0 in the potential range of −0.75 to −1.0 V. The pH of 2.0 was chosen as the optimum pH due to a good stripping signal of the reduction peak. There were no significant interfering ion effects on the electroanalysis of metsulfuron-methyl. The optimized parameters were then used to determine metsulfuron-methyl in the commercial pesticide Ally. The proposed method was highly sensitive due to the lower limit of determination (0.04 mg/L), being relatively selective, and consisting of good precision. The recovery values achieved were about 93% in water samples for this analysis.

Little information exists about pesticide availability and its effect on pest control in rural regions of developing countries. The availability of different insecticidal ingredients in rural areas of Cambodia was determined by inspecting labels on products used by farmers and in retail shops. A large number of products available in markets and used by farmers contained abamectin, emamectin benzoate, cypermethrin, and chlorpyrifos. The effects on the brown planthopper (BPH; Nilaparvata lugens (Stål)) were investigated by comparing the susceptibility of three BPH populations in Cambodia to twelve active ingredients in 2015. All populations showed high susceptibility to abamectin and cypermethrin; however, regional differences in susceptibility were observed for the other ingredients. The implication was that farmers selected the most effective products based on sellers’ opinions. It is important to monitor insecticide use and BPH susceptibility in each region of Cambodia in order to minimize the risk of high BPH population densities.

Pesticide residue levels in various parts of sweet corn ears were analyzed. For this purpose, five pesticides were sprayed on corn in two different fields, and the harvested samples were separated into four portions, namely kernels, cobs, silks, and husks. Each of these portions was then separately analyzed. Pesticide residues were predominantly distributed in the silk and husk portions, which constituted ≥91% of the whole crop, whereas relatively minimal residues remained in the kernel and cob portions. Further, residue distributions in the silks and husks were found to differ between the two fields. The calculated residue levels in kernels with the cob and silk were obviously higher than the residue levels in the kernel alone (max. >62 times different). This result suggests that the silk portion could greatly affect pesticide residue levels in the edible portion of corn.

One of the germination stimulants for root parasitic weeds produced by maize (Zea mays) was isolated and named methyl zealactonoate (1). Its structure was determined to be methyl (2E,3E)-4-((RS)-3,3-dimethyl-2-(3-methylbut-2-en-2-yl)-5-oxotetrahydrofuran-2-yl)-2-((((R)-4-methyl-5-oxo-2,5-dihydrofran-2-yl)oxy)methylene)but-3-enoate using by 1D and 2D NMR spectroscopy and ESI and EI–MS spectrometry. Feeding experiments with ¹³C-carlactone (CL), a biosynthetic intermediate for strigolactones, confirmed that 1 is produced from CL in maize. Methyl zealactonoate strongly elicits Striga hermonthica and Phelipanche ramosa seed germination, while Orobanche minor seeds are 100-fold less sensitive to this stimulant.

The nematode Phasmarhabditis hermaphrodita is the only commercial biological control agent for terrestrial slugs. We investigated whether the predicted conditions of winter warming could have any effect on its performance. In the presence of nematodes, slug damage to lettuce plants and slug survival were significantly lower under the predicted conditions of winter warming than under normal winter conditions, while in the absence of nematodes, slug damage and survival were similar under the conditions of winter warming and under current winter conditions. The data suggest that P. hermaphrodita may perform better under the predicted conditions of winter warming.