Journal of Pesticide Science
Online ISSN : 1349-0923
Print ISSN : 1348-589X
ISSN-L : 0385-1559
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Volume 33, Issue 1
Displaying 1-21 of 21 articles from this issue
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Special Topic: Recent advances in studies on actions of pesticides and bioactive molecules
Review
  • Insecticide interactions with γ-aminobutyric acid and nicotinic receptors: predictive aspects of structural models
    John E. Casida, Motohiro Tomizawa
    Article type: Review
    2008 Volume 33 Issue 1 Pages 4-8
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-07
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    An insecticide binding site may be blocked by widely diverse chemicals, as with the γ-aminobutyric acid receptor (GABAR), or accept only closely related compounds, as illustrated by the nicotinic acetylcholine (ACh) receptor (nAChR). The human GABAR β3-homopentamer resembles the insect receptor in sensitivity and specificity for noncompetitive antagonists (NCAs), prompting exhaustive site-directed mutagenesis (cysteine scanning), which pinpointed the critical active site as pore-facing residues Ala-2′, Thr-6′ and Leu-9′ and led to a binding site model which fits several classes of insecticidal NCAs. The nAChR agonist site was approached with an ACh binding protein (AChBP) by photoaffinity labeling and neonicotinoid docking. Chloropyridinyl chlorine contacts Ile-106/Met-116 and nitrogen is directed to Ile-118/Trp-147 via a solvent bridge(s). The guanidine/amidine plane undergoes π-stacking with Tyr-188, and the nitro/cyano pharmacophore interacts with Ser-189/Cys-190, thereby defining the binding pocket that models AChBP and possibly nAChR potency and selectivity.
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Commentaries
  • Pharmacophore of neonicotinoid insecticides
    Shinzo Kagabu
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 9-13
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-05
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    Our recent study related to neonicotinoid pharmacophore was presented. The first topic described on the QSAR study with 17 variants of 2-nitroiminoimizolidine. The insect neuroblocking potency is proportionally related both to the Mulliken charge on the nitro oxygen atom and log P. The second raised the functional possibility of the 3-fluoropropyl group as an H-bond acceptor for the neonicotinoid skeleton. Its 2-nitroiminoimidazolidine derivative actually showed the insecticidal tendency common to the neonicotinoids bearing a 6-chloro-3-pyridylmethyl group, although the activating strength was not as high as expected. The third introduced a new type of neonicotinoid compounds of alkylene-tethered twin-structure. The insecticidal activity against American cockroaches was dependent on the tether length and maximized at the hexamethylene with the minimum lethal dose of 2.2 nmol/insects, comparable to that of imidacloprid.
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  • Synthesis and biological activity of novel anti-juvenile hormone agents
    Eiichi Kuwano, Norihiro Fujita, Kenjiro Furuta, Naotaka Yamada
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 14-16
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-08
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    Ethyl 4-[2-(tert-butylcarbonyloxy)butoxy]benzoate (ETB) is a partial juvenile hormone (JH) antagonist which targets larval epidermis. We converted ETB to ethyl 4-(2-substituted alkyloxy)benzoates. These compounds induced precocious metamorphosis in the silkworm, Bombyx mori, which is a clear sign of JH deficiency, and their activity was completely counteracted by the simultaneous application of a JH agonist, methoprene. Among these novel compounds, ethyl 4-(2-benzylhexyloxy)benzoate (KF-13) showed high precocious metamorphosis-inducing activity at low doses, but its activity decreased with increasing dose, probably due to their JH-like activity. KF-13 is an enantiomeric compound. The (S)-enatiomer of KF-13 was more active than the (R)-enantiomer at low doses, but at high doses the activity was reversed (R>S). Hemolymph JH esterase activity, which is indispensable for the initiation of pupation in normal last-instar larvae, was induced in 4th-instar larvae by treatment with KF-13. 2-(6-Methyl-3-pyridyloxy)hexyl and 2-phenoxyhexyl analogs showed JH activity when topically applied to allatechtomized 4th-instar larvae.
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  • Epoxyalkenyl sex pheromones produced by female moths in highly evolved groups: biosynthesis and its endocrine regulation
    Tetsu Ando, Takeshi Kawai, Kanae Matsuoka
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 17-20
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-06
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    Polyunsaturated hydrocarbons with a C17-C23 straight chain and the epoxy derivatives constitute a second major class of lepidopteran sex pheromones and are referred to as Type II pheromones. While regionspecific epoxidation proceeds in a pheromone gland, the hydrocarbons are biosynthesized from dietary polyunsaturated fatty acids outside the pheromone gland and transported into the gland after association with lipophorin. In vivo as well as in vitro experiments using Japanese giant looper (Ascotis selenaria cretacea, Geometridae) demonstrated that pheromone biosynthesis-activating neuropeptide (PBAN) accelerated precursor uptake by the gland but not the biosynthetic step, which was contrast with the biosynthesis of Type I pheromones. The neuropeptide of A. s. cretacea, Assc-PBAN, was characterized to clarify its mode of unique action.
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  • Regulation of bombykol production by tyramine and octopamine in Bombyx mori
    Akinori Hirashima
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 21-23
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-12
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    The relationship between bombykol production and biogenic amines in brain–suboesophageal ganglion (SOG) complexes in Bombyx mori was investigated using reversed-phase high-performance liquid chromatography (HPLC) with electrochemical detection (ECD). Changes in octopamine (OA), dopamine (DA) and tyramine (TA) levels in brain–SOG complexes relative to mating stimuli were examined. TA increased significantly after mating, whereas there were no significant differences in OA and DA levels in brain–SOG complexes between virgin and mated females. Receptors can either inhibit or activate adenylate-cyclase activity by TA or OA in the central nervous system. Involvement of TA and OA in insect sex-pheromone production is discussed. The present studies could provide useful information for the characterization and differentiation of TA and OA receptors, and may help to point the way towards developing extremely potent and relatively specific TA or OA ligands, leading to potential insecticides, although further research is necessary.
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  • Bombyx mori phenolamine receptors: a comparative molecular biological study
    Yoshihisa Ozoe, Jia Huang
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 24-27
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-09
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    The cDNAs coding for two biogenic amine receptors were cloned from the silkworm Bombyx mori and stably expressed in HEK-293 cells; these receptors were identified as an α-adrenergic-like octopamine (OA) receptor, which is linked to elevations of intracellular Ca2+ and cAMP levels, and a tyramine (TA) receptor, which is linked to an attenuation of intracellular cAMP production. The respective amino acid residues of OA and TA receptors involved in interactions with OA and TA were identified by functional assays of mutant receptors generated by site-directed mutagenesis. An activation mechanism of the OA receptor was proposed based on the assumption of three conformational states.
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  • Efficacious syntheses of alkylphenol ethoxylates and ethoxycarboxylates with long and single length PEG chain and their application to environmental fate study
    Yayoi Ichiki, Toshie Ishimoto, Hiromichi Yoshikawa
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 28-32
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-15
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    The Williamson alkylation of a phenolic hydroxyl group of a 4-tert-octylphenol by 2-[2-(2-chloroethoxy)ethoxy]ethanol in the presence of potassium carbonate afforded the corresponding 9-(4-tert-octylphenyl)-3,6,9-trioxanonan-1-ol (OP3EO) quantitatively. Using powdered sodium hydroxide in place of potassium carbonate in the presence of phase transfer catalyst, alkylation of the terminal hydroxyl group occurred to give a mixture of OP3EO, 18-(4-tert-octylpheny)-3,6,9,12,15,18-hexaoxaoctadodecan-1-ol (OP6EO), 27-(4-alkylphenyl)-3,6,9,12,15,18,21,24,27-nonaoxaheptacosan-1-ol (OP9EO) and so on. Many types of OPkEO (k=4, 5, 6…) could be obtained by using OP1EO and OP2EO as starting materials. The use of OPkEO with a long and single length polyethylene glycol (PEG) chain was effective for studying the environmental fate of APEOs.
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  • Endocrine disruptors that disrupt the transcription mediated by androgen receptor
    Hiroto Tamura, Akifumi Hosoda, Miki Akamatsu
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 33-39
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-11
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    The Ministry of Environment in Japan (formerly the Japan Environment Agency) has made a priority list of compounds, SPEED 98, to preferentially examine whether they act as endocrine active chemicals and conducted a project to scientifically address endocrine disruptor issues. Out of around 100 compounds listed in SPEED 98 and related compounds, thirty-six acted as pure androgen receptor (AR) antagonists, whereas 13 showed both AR agonist and antagonist activities based on an in vitro reporter gene assay. The structural difference between AR agonists and antagonists was explained by Comparative Molecular Field Analysis (CoMFA). The precise structural requirements for AR agonists and/or antagonists are described as follows: in the case of AR agonist, the distance between two functional groups with H-bonding ability corresponding to 3-keto and 17β-OH groups should be near 10 Å to maintain a favorable H-bond position while the length axis of antagonists should be less than or more than 10 Å so as not to make an H-bond by interaction with Asn705 and Thr877 in the steroid D ring anchoring pocket, preventing the correct positioning of helix 3 (H3) and helix 12 (H12). This hypothetical general rule is named “Near 10 Å polar Interaction Rule”.
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  • Total utilization of tropical plants Leucaena leucocephala and Alpinia zerumbet
    Shinkichi Tawata, Masakazu Fukuta, Tran Dang Xuan, Farah Deba
    Article type: Commentary
    2008 Volume 33 Issue 1 Pages 40-43
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.R07-10
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    In Okinawa, leucaena (Leucaena leucocephala de Wit) has great potential as animal feed for its high protein content, but its use has been limited owing to the presence of mimosine (β-[N-(3-hydroxy-4-pyridone)]-α-aminopropionic acid) which, when ingested, causes diseases in animals. A detoxifying enzyme, mimosinase, was purified from leucaena leaves and cDNA was cloned based on the amino acid sequence. During essential oil production and fiber isolation from alpinia (Alpinia zerumbet), large volumes of solid and squeezed wastes are produced and subsequently discarded. An extraction protocol to obtain essential oils, dihydro-5,6-dehydrokawain (DDK) and enriched antioxidant phenolic extracts from fresh leaves or rhizomes of alpinia and its waste was developed.
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Original Articles
  • Insecticidal properties of bistrifluron against sycamore lace bug, Corythucha ciliata (Hemiptera: Tingidae)
    Changmann Yoon, Jeong-Oh Yang, Shin-Ho Kang, Gil-Hah Kim
    Article type: Original Article
    2008 Volume 33 Issue 1 Pages 44-50
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.G07-09
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    Bistrifluron, a member of the benzoylphenylurea (BPU) class, was developed in the Republic of Korea as an inhibitor of chitin synthesis. This study examined the effect of bistrifluron on insecticidal activity, adult longevity, fecundity and ovarian development in the sycamore lace bug, Corythucha ciliata. The results showed that bistrifluron had no direct effect on the egg, but produced 100% mortality in larvae hatched within 24 hr with a similar effect regardless of the instars of the larvae (LC50=0.01–0.06 ppm). When the final instar was treated with bistrifluron, the emergence rate, adult longevity and reproduction decreased with increasing concentration (up to 100 ppm). With the passage of time after the final larvae had emerged, chemical treatment delayed the preoviposition period of the adults at high concentrations, and decreased adult longevity, fecundity and the hatching rate. Ovarian development of the adult was also inhibited.
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  • Application of commercially available fenitrothion-ELISA kit for soil residue analysis
    Sonny Conde, Kousuke Suyama, Kazuhito Itoh, Hiroki Yamamoto
    Article type: Original Article
    2008 Volume 33 Issue 1 Pages 51-57
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.G07-21
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    A commercially available fenitrothion-ELISA kit, designed for residue analysis of crop samples, was applied in a method development study using 10 different soils spiked with the target pesticide. Recoveries determined by gas chromatography (GC) were compared to those in ELISA analysis. Recoveries in ELISA were biased high in six soil samples which had low pH and high sand content. The range of recoveries in 10 soils was from 87 to 163% while, in contrast, GC recovery was 72–86%. Soil matrix, such as high-molecular-weight organics and divalent cations, influenced the ELISA reaction to cause an overestimation of recovery.
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  • Insecticidal and neuroblocking potencies of variants of the thiazolidine moiety of thiacloprid and quantitative relationship study for the key neonicotinoid pharmacophore
    Shinzo Kagabu, Keiichiro Nishimura, Yuji Naruse, Ikuya Ohno
    Article type: Original Article
    2008 Volume 33 Issue 1 Pages 58-66
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    Advance online publication: December 28, 2007
    DOIhttps://doi.org/10.1584/jpestics.R07-25
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    The pharmacophore of the neonicotinoid insecticide thiacloprid, cyanoiminothiazolidine, was modified to heterocycles such as imidazolidine, pyrrolidine and oxazolidine (the central ring hereafter). Their 6-chloro-3-pyridylmethyl or 5-chloro-3-thiazolylmethyl derivatives were examined for insecticidal activity against the American cockroach by injection and neuroblocking activity using the cockroach ganglion. The derivatives showed strong insecticidal activity with the minimum lethal dose (MLD) of about 10 nmol, which were however mostly weaker than the corresponding nitromethylene or nitroimine compounds. The activity was enhanced in the presence of synergists. The neuroblocking effect of cyanoimino compounds was at the micromolar level. Quantitative analysis for 23 variants of the key pharmacophore, constructed with the central ring conjugated to an NCN, CHNO2, or NNO2, showed that the neuroblocking potency is proportional to the Mulliken charge on the nitro oxygen atom or cyano nitrogen atom. The optimum log P value was evaluated as 1.19. The equation for the insecticidal- vs. the neuroblocking-potencies indicated that both potencies are related proportionally with each other when the other factors are the same.
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  • Role of ethylene in abnormal shoot growth induced by high concentration of brassinolide in rice seedlings
    Nguyen Minh Chon, Naoko Nishikawa-Koseki, Yasutomo Takeuchi, Hiroshi A ...
    Article type: Original Article
    2008 Volume 33 Issue 1 Pages 67-72
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    Advance online publication: December 28, 2007
    DOIhttps://doi.org/10.1584/jpestics.G07-20
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    A high concentration of brassinolide (BL) induced abnormal shoot shape in rice seedlings, that is, the newly developed leaf sheath was shorter than the old sheath, and increased the number of leaves. The involvement of ethylene and cyanide, co-metabolites during ethylene biosynthesis, in abnormal shoot growth was analyzed by comparing the action mechanism of BL with that of quinclorac in barnyard grass seedlings. BL strongly stimulated ethylene production, and the amount of ethylene and the third leaf sheath length in rice seedlings were negatively correlated. Exogenously applied ethephon also induced abnormal growth of rice seedlings. L-α-amino-ethoxyvinyl-glycine (AVG), an ethylene biosynthetic inhibitor, partially reversed abnormal shoot growth. The level of endogenous cyanide was low in rice seedlings, because of the high level of β-cyanoalanine synthase (CAS) activity, and exogenously applied KCN did not induce abnormal shoot growth. The results indicate that BL-induced abnormal shoot growth of rice seedlings was probably mediated by ethylene production.
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Note
  • Improvement of ELISA analysis for soil residue analysis by reducing soil matrix effects
    Sonny Conde, Kousuke Suyama, Kazuhito Itoh
    Article type: Note
    2008 Volume 33 Issue 1 Pages 73-75
    Published: February 25, 2008
    Released on J-STAGE: February 20, 2008
    DOIhttps://doi.org/10.1584/jpestics.G07-37
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    Improvement of the commercially available fenitrothion-ELISA kit for soil residue analysis was examined. Recovery trials were conducted with 5 soils spiked at 0.5 μg/g soil. Interference of soil matrix was not adequately removed by the addition of synthetic zeolite in extraction, although it reduced Ca2+ concentration. Ultrafiltration at 9 kDa after dilution of the soil extracts gave enough results to compare with those obtained by gas chromatography. It was suggested that overestimation in ELISA was caused by high-molecular-weight humus-like compounds in soil extracts.
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PART II (IN JAPANESE)
Original Article (with Abstract English)
  • Fate and behavior of fenitrothion in the atmosphere after application on a paddy field
    Takashi Watanabe
    Article type: Original Article
    2008 Volume 33 Issue 1 Pages 77-86
    Published: February 20, 2008
    Released on J-STAGE: December 07, 2013
    DOIhttps://doi.org/10.1584/jpestics.33.77
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    Fenitrothion was aerially sprayed onto a paddy field, and transformed by photolysis to fenitrooxon to increase its toxicity. The concentration of fenitrooxon was measured in rice foliage and the atmosphere. The concentration in rice foliage ranged 0.1–0.5 mg in 1 m2 of paddy area, and the concentration in the atmosphere ranged <0.02–0.07 μg/m3, varying in a constant range. The concentration of fenitrooxon in rice foliage was predicted by phototransformation of fenitrothion on rice leaves, and the predicted values were almost equal to the observed values. The concentration of fenitrooxon in the atmosphere was predicted by volatilization from rice leaves, and the predicted values were equal to the observed values with an error range; however, the predicted concentrations transformed by photodecomposition of fenitrothion in the atmosphere were extremely lower than the observed values. The ratio of fenitrooxon and fenitrothion on rice leaves was correlated with that in the atmosphere.
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Abstracts of Articles in Part I
Commentaries
Symposia
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