Journal of Pesticide Science

Review Article

Toxicity, bioaccumulation and metabolism of pesticides in the earthworm

Toshiyuki Katagi, Keiko Ose

2015 Volume 40 Issue 3 Pages 69-81
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: June 12, 2015

DOIhttps://doi.org/10.1584/jpestics.D15-003

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The toxic effects of pesticides on earthworms, one of the most important bioindicators in the terrestrial environment, are closely related to their body burden determined by uptake, metabolism and excretion processes. Not only the passive diffusion via the outer skin from a dissolved fraction of pesticide but also the ingestion of contaminated soil and food governs the uptake process, with each contribution controlled by either the hydrophobicity of the pesticide or the soil organic matter. Although the available information is limited, earthworms are likely to metabolize pesticides via hydrolysis and oxidation (Phase I) followed by conjugation (Phase II), and low bioaccumulation is observed as a result for most pesticides. The acute toxicity in the soil exposure can be partly explained by the dissolved fraction of pesticide in pore water, but the contribution of dietary uptake and metabolism should be further studied to correctly evaluate pesticide toxicity.

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Original Articles

Dissipation kinetics of glyphosate in tea and tea-field under northwestern mid-hill conditions of India

Bandana Bandana, Neelam Sharma, Robin Joshi, Ashu Gulati, Shobha Sondh ...

2015 Volume 40 Issue 3 Pages 82-86
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: June 24, 2015

DOIhttps://doi.org/10.1584/jpestics.D14-085

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A study was conducted to determine the dissipation of glyphosate applied at three dose levels in tea crop in mid hill conditions of northwest Himalaya, India in two consecutive seasons. More than 65% of the initial residues in the soil were found to have dissipated within 30 days following application to the tea irrespective of the dose. Glyphosate persisted in the soil for up to 30, 45 and 60 days at application doses of 0.5, 1.0 and 2.0 kg/ha, respectively. Glyphosate residues in the tea leaves were detected for up to 15 days with all three treatments. Half lives of glyphosate ranged from 5.80 to 19.10 days in the soil of the tea fields and 5.82 to 7.91 days in the tea leaves at the three doses. Glyphosate concentrations in the tea leaves were found to be below the maximum residue limit (1 mg/kg).

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Decrease in the matrix enhancement effect on pesticides analysis with GC-MS using new types of solid-phase extraction column

Kuniyo Sugitate, Machiko Saka

2015 Volume 40 Issue 3 Pages 87-91
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: June 04, 2015

DOIhttps://doi.org/10.1584/jpestics.D15-010

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Matrix removal ability of several new types of Solid Phase Extraction (SPEs) column was tested. E-HyCu is made of new type of material, chemically-modified carbon fibers, and can remove food components, monoacylglycerols, tocopherols, and sterols, etc. Z-Sep+ and Z-Sep/C18 are also new types of materials that contain zirconium dioxide. Z-Sep+ and Z-Sep/C18 are used for high lipid samples as the dispersive SPE in the QuEChERS method. We evaluated these sorbents as filled up columns. In our previous study, we reported that when the analytical method based on the multiresidue method is applied, monoacylglycerols are the most significant components that cause a matrix enhancement effect on pesticides in food using GC-MS. These new types of SPEs could remove not only monoacylglycerols, but also fatty acids, tocopherols, flavonoids, and sterols. The matrix enhancement effects of approximately 260 pesticides spiked in brown rice extracts pretreated with these SPEs were dramatically reduced.

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Insecticidal activity and up-regulation of juvenile hormone response genes by juvenile hormone agonists in the western flower thrips, Frankliniella occidentalis

Youhei Suzuki, Kenjiro Furuta, Kei Maeda, Kakeru Yokoi, Ken Miura, Tos ...

2015 Volume 40 Issue 3 Pages 92-98
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: June 30, 2015

DOIhttps://doi.org/10.1584/jpestics.D14-098

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Insect juvenile hormone (JH) agonists have been utilized as insect growth regulators for pest management against several pest insect species. We investigated insecticidal activity and the induction ratios of two JH-inducible genes, Krüppel homolog 1 (Kr-h1) and broad (br), using 12 test compounds in the western flower thrips Frankliniella occidentalis (Pergande). In insecticidal assays against propupae to inhibit metamorphosis to the adult, the activities of pyriproxyfen, KF-13, ETB, and KF-31 were potent at 10 mM, while those of the other 8 test chemicals were not. In quantitative RT-PCR, these 4 chemicals up-regulated the transcript levels of Kr-h1 and br, while the induction of transcription by chemicals with lower insecticidal activities was relatively small. Thus, the induction ratios of Kr-h1 and br correlated with insecticidal activity. Assessments of the induction ratios of these genes may be a useful method in the preliminary screening of JH agonists.

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Different uptake pathways between hydrophilic and hydrophobic compounds in lateral roots of Cucurbita pepo

Kiyoshi Yamazaki, Hiroki Tsuruta, Hideyuki Inui

2015 Volume 40 Issue 3 Pages 99-105
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: June 12, 2015

DOIhttps://doi.org/10.1584/jpestics.D14-081

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From previous reports, uptake and accumulation of organic compounds by plant roots are strongly related to water solubility. However, the relation between uptake pathways and water solubility remains unclear. Here, we used confocal laser scanning microscopy to observe the uptake of fluorescent hydrophilic and hydrophobic compounds in the living roots of Cucurbita pepo. We found strong regulation of the uptake of berberine, a hydrophobic compound at the endodermal Casparian strip, as previously reported, and similar regulation was also observed in the pericycle. Berberine was loaded into and transported upward through the protoxylem. Perylene, a highly hydrophobic compound, in contrast, passed through the Casparian strip and accumulated preferentially in the endodermis and pericycle. The results of our solvent extraction suggested that perylene diffused into the non-aqueous phase. Therefore, the uptake pathways for the hydrophilic and hydrophobic compoundss are different. These results offer a new way to understand the uptake of agrochemicals and pollutants and to select host plants for phytoremediation.

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Determination of imazethapyr residues in soil and grains after its application to soybeans

Shobha Sondhia, Pramraj Jagoji Khankhane, Pradyuman Kumar Singh, Ajit ...

2015 Volume 40 Issue 3 Pages 106-110
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 24, 2015

DOIhttps://doi.org/10.1584/jpestics.D14-109

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Imazethapyr is widely used in soybean, and leguminous crops for control of wide variety of broad leaf weed species. A study was conducted to evaluate residues of imazethapyr in the soil and soybean grain at five different locations in India. Imazethapyr was applied at 100 g/ha, as a post emergence herbicide to control weeds in soybean fields. Residues of imazethapyr were found in the range from 0.006 to 0.018 µg/g in the soybean grains samples in all five locations. However in the soil, residues were found to be below 0.0010 µg/g in four locations, and 0.0015 µg/g in one location. Less residues were found in soils as compared to plant samples. Based on this study a pre-harvest interval of 90–102 days is suggested for soybean crops after imazethapyr application. This indicates the judicious use of imazethapyr by farmers in soybean fields.

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Species differences in the developmental toxicity of procymidone

—Remarkable variation in pharmacokinetics, metabolism, and excretion—

Yoshitaka Tomigahara, Hirokazu Tarui, Hirohisa Nagahori, Kenji Sugimot ...

2015 Volume 40 Issue 3 Pages 111-123
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 23, 2015

DOIhttps://doi.org/10.1584/jpestics.D15-008

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There are species differences regarding the developmental toxicity of procymidone (Sumilex®), a fungicide with a weak anti-androgenic activity. To clarify key factors of these species differences, pharmacokinetic and excretion studies in rats, rabbits, and monkeys were conducted using ¹⁴C-labeled procymidone. One hydroxylated metabolite of procymidone (Hydroxylated-PCM: very weak anti-androgen) was found to exist longer and at a much higher concentration in rat plasma than in rabbit and monkey plasma. In rabbits and monkeys, Hydroxylated-PCM was transformed into a glucuronic acid conjugate (Hydroxylated-PCM-glucuronide: non-anti-androgen) and rapidly excreted into urine as a major metabolite. On the other hand, it was a minor metabolite in rat urine. The results of biliary excretion studies indicated that these species differences were caused by the species differences in the biliary excretion of Hydroxylated-PCM-glucuronide; this variation in biliary excretion rate was concluded to be related to species differences in developmental toxicity.

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Species composition, gibberellin production and sensitivity to ipconazole of the Fusarium fujikuroi species complex isolates obtained before and after its launch

Hideaki Tateishi, Haruhisa Suga

2015 Volume 40 Issue 3 Pages 124-129
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 24, 2015

DOIhttps://doi.org/10.1584/jpestics.D14-083

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Sensitivities to ipconazole of 50 isolates of the Fusarium (Gibberella) fujikuroi species complex (Ff complex) obtained from rice in Japan before 1994 (group A: before the launch of ipconazole) and 65 isolates after 1994 (group B) were investigated. Most isolates were identified as Fusarium fujikuroi, while 5 isolates in group A and 4 isolates in group B were identified as Fusarium proliferatum with species diagnostic PCR-RFLPs. The minimum inhibitory concentration (MIC) range, profiles in sensitivity to ipconazole and gibberellin production were similar in both groups. Gibberellin production was detected in the F. fujikuroi isolates with higher sensitivity to ipconazole but not in the isolates with lower sensitivity and F. proliferatum. High efficacy of ipconazole against rice “Bakanae” disease was confirmed by using the gibberellin-producing F. fujikuroi isolates in group B. No shift in sensitivity to ipconazole was verified and this may contribute to the stable efficacy against rice “Bakanae” disease.

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Bioconcentration and metabolism of trans-tetramethrin in fish

Mitsugu Miyamoto, Shoji Saito, Takuo Fujisawa, Toshiyuki Katagi

2015 Volume 40 Issue 3 Pages 130-137
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 24, 2015

DOIhttps://doi.org/10.1584/jpestics.D15-027

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The bioconcentration and metabolism of ¹⁴C-labeled trans-isomers of tetramethrin (I) [3,4,5,6-tetrahydrophthalimidomethyl (1RS)-trans-chrysanthemate] in bluegill sunfish (Lepomis macrochirus) were examined under flow-through conditions. Ester cleavage followed by rapid liberation of a hydroxymethyl group from the alcohol moiety resulted in the formation of trans-chrysanthemic acid (VI) and 3,4,5,6-tetrahydrophthalimide (III) as primary metabolites in fish. III was either hydrolyzed to the diacid (V) or reduced at the 1,2-double bond (IV). VI and its metabolites formed through successive oxidation at the isobutenyl moiety were further conjugated with glucuronic acid or taurine. The rapid and extensive metabolism of trans-I with a short depuration half-life of 0.54–0.72 days resulted in a much lower bioconcentration factor (BCF), 180–310, than expected from its hydrophobicity (log K_ow=4.6). The BCF value of its cis-isomer was conveniently estimated to be 230–400 by taking into account the different degradation rates between both isomers evaluated through an in vitro metabolism study.

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Note

Synthesis and biological evaluation of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties

Mingzhen Mao, Yuxin Li, Qiaoxia Liu, Lixia Xiong, Xiao Zhang, Zhengmin ...

2015 Volume 40 Issue 3 Pages 138-142
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 24, 2015

DOIhttps://doi.org/10.1584/jpestics.D15-020

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Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an N-isopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 µg⁄mL indicated that some compounds exhibited moderate fungicidal activities.

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Society Awards 2015

Studies on chemical ecology of the heteropteran scent gland components

Koji Noge

2015 Volume 40 Issue 3 Pages 143-145
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 24, 2015

DOIhttps://doi.org/10.1584/jpestics.J15-03

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Heteropterans, or true bug, produce foul-smelling odors commonly composed of α,β-unsaturated aldehydes and their derivatives such as 4-oxo-(E)-2-hexenal that play important roles in chemical defense and communication. However, the defensive roles of each scent gland components are not well understood. In this study, repellent, feeding deterrent, toxic and antimicrobial effects of each scent gland component were evaluated using chemical identification and behavioral assays. (E)-2-Hexenal and (E)-2-octenal showed repellent activities against insect predators. (E)-2-Octenal also functioned as feeding deterrent agaist the predators. Our predator behavioral assays revealed that OHE was deterrent and toxic but not repellent against the predators. This compound also induced permanent locomotive impairment in crickets that correlates with free thiol depletion. All of the α,β-unsaturated aldehydes showed antimicrobial activities. Having diverse defensive components that function differently in a blend could fortify the heteropteran chemical defense system.

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Structure-activity relationship studies of insect and plant steroid hormones

Bunta Watanabe

2015 Volume 40 Issue 3 Pages 146-151
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 23, 2015

DOIhttps://doi.org/10.1584/jpestics.J15-04

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Ecdysteroids and brassinosteroids are steroid hormones that regulate insect molting and plant growth, respectively. In this study, novel ecdysteroids and brassinosteroids were designed and synthesized, and their biological activity was evaluated. Structure-activity relationship details between the structure of the steroid skeleton of ecdysteroids and their molting hormone receptor binding activity, as well as between the side chain structure of brassinosteroids and their plant hormonal activity were investigated. The results of these investigations suggested that in order to exhibit hormonal activity in insects or plants, the structure of the side chain in these hormones should be more important than that of the steroidal core skeleton.

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Study on the structure and insecticide sensitivity of the RDL GABA receptor^#

Toshifumi Nakao

2015 Volume 40 Issue 3 Pages 152-159
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 10, 2015

DOIhttps://doi.org/10.1584/jpestics.J15-01

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In this study, a novel A2′N mutation that confers fipronil resistance was found in the membrane-spanning region M2 of the RDL GABA receptor from fipronil-resistant planthoppers in the heterozygous state. Furthermore, rapid monitoring methods using polymerase chain reaction-restriction fragment polymorphism were employed to detect fipronil-resistant planthoppers carrying the A2′N mutation. It was found that 3-benzamido-N-[4-(perfluoropropan-2-yl)phenyl]benzamides (meta-diamides) comprise a distinct class of RDL GABA receptor antagonists with high insecticidal activity. A membrane potential assay demonstrated that meta-diamides acted on A2′ mutant RDL GABA receptors at the same level as the wild-type RDL GABA receptor. In addition, meta-diamides may act on the M1–M3 intersubunit pocket, whereas cyclodienes and fipronil act on the A2′ residue in the pore formed by M2s. Thus, meta-diamides are expected to be effective against cyclodiene- and fipronil-resistant pests carrying A2′ mutations. Meta-diamides also exhibited high selectivity toward insect RDL GABA receptors.

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Development of the novel formulation “MAMETSUBU” for the paddy rice

Shigeki Fujita, Manabu Hiraoka, Toshihiro Ikeuchi, Masami Kobayashi

2015 Volume 40 Issue 3 Pages 160-164
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: July 24, 2015

DOIhttps://doi.org/10.1584/jpestics.J15-02

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We tried to develop a novel easy-to-use labor-saving formulation. And we have developed the “MAMETSUBU” formulation for paddy fields. This formulation has 3 to 8 mm diameters and disperses on the surface of water. This is a highly labor-saving formulation that can be applied from the levees by various methods without the necessity of stepping into the paddy fields. The conditions that disturb diffusion of an active ingredient in the “MAMETSUBU” formulation often changes. Therefore, spreading property of an active ingredient in the formulations was evaluated not only in small experimental fields but also in the actual paddy fields. In all of the experiments, the spreading property of the active ingredient was found sufficient enough for the formulations to be practically used. The conditions of paddy fields are usually not the same, but the “MAMETSUBU” formulation is a new formulation that can be reasonably applied.

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Development and diffusion of a systematic method for determining multiple pesticide residues in agricultural products

Eiji Ueno

2015 Volume 40 Issue 3 Pages 165-172
Published: August 20, 2015
Released on J-STAGE: August 20, 2015
Advance online publication: August 05, 2015

DOIhttps://doi.org/10.1584/jpestics.J15-05

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In Japan, the Positive List System for the regulation of agricultural chemical residues in foods has been in force since May 29, 2006. Moreover, food poisoning caused by methamidophos-laced frozen gyōza dumplings came to light on Jan. 30, 2008. The news has set off alarms about the safety of not only perishables but also unexpected pesticides in processed foods. Therefore, a reliable systematic method was developed for determining pesticide residues in various foods. Firstly, ca. 200 target pesticides were selected by statistically analyzing the monitoring data in Aichi Prefecture. Secondly, a systematic method using plural separation and detection systems combining GC-MS/MS and LC-MS/MS as first priority was constructed. As the sample preparation method corresponding to the systematic method, a simple and easy acetonitrile extraction method, an auto-cleanup system combining GPC and mini-column SPE were developed. Thirdly, a new official multi-residue method that is able to determine a wide range of pesticides in various foods including fatty processed foods was developed. And finally, a comprehensive chromatographic detection system by dual-column GC-MS(/MS) and an interactive database without the use of pesticide standards was commercialized.

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Erratum

Erratum

2015 Volume 40 Issue 3 Pages 173
Published: August 20, 2015
Released on J-STAGE: August 20, 2015

DOIhttps://doi.org/10.1584/jpestics.C15-02

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