Journal of Pesticide Science
Online ISSN : 1349-0923
Print ISSN : 1348-589X
ISSN-L : 0385-1559
Volume 8, Issue 4
Displaying 1-32 of 32 articles from this issue
  • Takayuki SUZUKI
    1983 Volume 8 Issue 4 Pages 419-428
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    Metabolism of pentachlorophenol (PCP) by Mycobacterium sp. which was isolated from soil, and converted PCP to pentachloroanisole (PCA) and partly to tetrachloro-1, 4-dimethoxybenzene (TCHD) was further studied. When washed cell suspension of the isolate was incubated with PCP in a mineral salt medium, tetrachlorocatechol (TCC), tetrachlorohydroquinone (TCHQ), tetrachloro-2-methoxyphenol (TCCM), and tetrachloro-4-methoxyphenol (TCHM) were detected in the benzene extracts from the incubation medium by GC after acetylation, besides PCA and TCHD. Tetrachloro-1, 2-dimethoxybenzene (TCCD) was also detected in the eluates after column chromatography from the benzene extracts. These metabolites were confirmed by mass spectra with GC-MS and by IR spectra after separation and purification by column and/or thin layer chromatography. Mycobacterium sp. converted TCHQ to TCHD via TCHM by successive methylation. TCC was also converted to TCCD via TCCM by this isolate. It was concluded from these results that Mycobacterium sp. metabolized PCP mostly through the methylation and at the same time part of PCP was hydroxylated at ortho and para positions to the hydroxyl group followed by successive methylation. Maximum rate of the methylation was observed between pH 6.5 and 7.0. The hydroxylation, however, was dominant below pH 6.0. The addition of nutrients into the incubation medium resulted in enhancement of the methylation and exclusive formation of PCA as a sole metabolite. Toxicity of PCA for Mycobacterium sp. and for germinating rice seeds was significantly low compared with PCP.
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  • Herbicidal Activity of N-Benzylbutanamides (Part 5)
    Osamu KIRINO, Yukio SUZUKI, Kazunori YANAGI, Akemi SOGABE, Masao MINOB ...
    1983 Volume 8 Issue 4 Pages 429-436
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    Optically active N-benzylbutanamides were prepared and their herbicidal activity against Scirpus juncoides and Echinochloa crus-galli was determined by the vial test. The crystal structure of N-(1′-methyl-1′-phenylethyl)-2-bromo-3, 3-dimethylbutanamide (S-47) and (2R, 1′S)-(-)-N-(1′-phenylethyl)-2-bromo-3, 3-dimethylbutanamide (S-44) was shown to have smooth shape by X-ray analysis and the absolute configuration of (-)-2-bromo-3, 3-dimethylbutanoic acid has been assigned as R. The activity of the (R)-(+)-isomer of S-47 was about 10 times higher than that of the (S)-(-)-isomer against a sensitive plant, S. juncoides, but the difference in the activity against a less sensitive plant, E. crus-galli, was only slight. The R-configuration at the acid moiety and the S-configuration at the amine moiety of S-44 were essential to the high activity.
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  • Tadao YAMADA, Takayuki SUZUKI
    1983 Volume 8 Issue 4 Pages 437-443
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Dwarf symptom of rice plants was generated with dechlorinated thiobencarb formed in soil, when a herbicide thiobencarb (benthiocarb, S-4-chlorobenzyl N, N-diethylthiocarbamate) was applied at a high rate to the paddy field which have been incorporated with a high rate of rice straws and grains. In order to compare the reductive dechlorination of CNP (chlornitrofen, 4-nitrophenyl 2, 4, 6-trichlorophenyl ether) which was applied to the field in combination with thiobencarb, CNP-amino (4-aminophenyl 2, 4, 6-trichlorophenyl ether) and its dechlorinated analogs were extracted from the soil samples which were treated with hot alkaline solution, trifluoroacetylated, identified and determined by GC and GC-MS, wherefore, a group of compounds including CNP are comprehensively dealt in the lump of the amino analogs, in this study. By these methods, 4-aminophenyl 2, 6-dichlorophenyl ether was detected in the soils since 34 days after the application of CNP, and the maximum content was 1.50ppm/dry soil. Subsequently, 4-aminophenyl 2-chlorophenyl ether and 4-aminophenyl phenyl ether were detected to lesser extents. However, 2, 4-dichlorophenyl and 4-chlorophenyl analogs were not detected more than a trace amount in the soils. The results reveal that the reductive dechlorination pathways, preceded by the replacement of the para-chlorine of the trichlorophenyl group, took place in the soils. It is suggested that the dechlorination of CNP in soil was rather slower and the products were more stable than that of thiobencarb.
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  • Koichiro KOMAI, Jun-ichi IWAMURA
    1983 Volume 8 Issue 4 Pages 445-450
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Biological activities of steviol-glucosides such as stevioside, rebaudioside B, stevioside A3, dulcoside A and rebaudioside C were tested by the rice seedling assay using one usual variety, Nihonbare and one dwarf variety, Tan-ginbozu. At the dosage of 100μM by root treatment method, 6 tested compounds were active in the leaf sheath elongation of Tanginbozu. But normal variety, Nihonbare showed no response to all glucoside at dosage tested. On the other hand, treatment of coleoptile application method indicated that a degree of activity of glucoside for the Tan-ginbozu is approximately the same as that by the root treatment method, at a dosage of 10μg per plant. These compounds also promoted the elongation of the hypocotyl and radicle of lettuce at concentration higher than 200μM. However, growth response to glucoside in seedling tests was at lower activity than that by steviol, aglycone of them.
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  • Naohiko ISOSE, Masatoshi MATSUO, Junshi MIYAMOTO
    1983 Volume 8 Issue 4 Pages 451-465
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    With single oral administration of 14C-carbonyl- or 14C-phenyl-labeled bromobutide, N-(1-methyl-1-phenylethyl)-2-bromo-3, 3-dimethylbutanamide to male and female rats at the rate of 5mg/kg b. w., the radiocarbon was excreted rapidly and completely into the feces and urine. Residue levels of 14C in tissues and organs were less than 0.11μg bromobutide eq/g tissue in male and 0.07μg bromobutide eq/g tissue in female on the 7th day after administration. The bromobutide dosed was mainly metabolized by phenyl- and t-butyloxidation, debromination, and glucuronidation. In particular, the metabolites which had received the oxidation reactions accounted for 32-40% and 58-63% of the bromobutide dosed, respectively and the debrominated products including debromo-bromobutide amounted to more than 50% forming the major metabolic pathways. In contrast, the hydroxylated products of the methyl group in amine moiety were found only in small quantity and little amide hydrolysates, sulfate- and amino acid-conjugates were detected in feces and urine. When male rats were treated with higher dose (125mg/kg b. w.) of 14C-carbonyl-bromobutide, the less oxidized metabolites were excreted to higher extents, but little changes were observed in the members of metabolites.
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  • Studies on the Residue of Mepronil Fungicide in Crops and Soils (Part 1)
    Yuzuru ASANO, Kanji ISHIKAWA
    1983 Volume 8 Issue 4 Pages 467-474
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    For microdetermination of mepronil fungicide, derivatization into a halogenated compound sensitive to electron capture detection was investigated. By a simple procedure it could be brominated to form dibromomepronil which was stable and highly sensitive to the detection. Mepronil reacted with bromine in benzene: methanol (99:1) media under cooling and the reaction completed within 30min. Several mepronil derivatives and other pesticides could also be easily brominated, although numbers of substituted bromine atoms of products varied by compound, indicating that this condition could be applied for the bromination of many other aromatic compounds. Besides, this reaction was more available than those of trifluoroacetylation and pentafluorobenzoylation. It was found that mepronil was very stable against acid and base hydrolysis.
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  • Studies on the Residue of Mepronil Fungicide in Crops and Soils (Part 2)
    Yuzuru ASANO, Toshiharu OISHI, Katsuo ANMA, Hiroshi ABE, Kanji ISHIKAW ...
    1983 Volume 8 Issue 4 Pages 475-482
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    A highly sensitive method for analysis of mepronil in soil was established by ECD-gas chromatography. The method consisted of sequential procedures of extraction by refluxing soil samples, liquid-liquid partition, bromination, silicagel column chromatography, and determination. Extraction efficiency was investigated using soil samples prepared by allowing to stand under the submerged or the upland condition for a long time over 2 months after application of mepronil. A mixture of methanol and 12N potassium hydroxide (3+1, v/v) was the best solvent for extraction of mepronil among several solvents tested. Refluxing with the solvent raised the efficiency. Recovery was more than 90% for 5 soils under the flooded condition, when mepronil was added at concentrations from 0.03 to 6.0ppm, and above 80% for 4 soils under the unflooded condition, when added at concentrations from 0.6 to 6.0ppm. The lower detection limit of mepronil in soil is calculated as 0.005ppm.
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  • Nobuyoshi MURAKAMI, Matazaemon UCHIDA, Kunihiro YABUTANI, Michinori OK ...
    1983 Volume 8 Issue 4 Pages 483-491
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    The radiocarbon in [aniline ring-14C(U)]flutolanil, 3′-isopropoxy-2-(trifluoromethyl)-benzanilide, orally administered to male rats at the dose of 20 (or 100)mg/kg was rapidly and almost completely excreted into urine and feces, 69 and 26 (or 67 and 30)% of the dose, respectively, within 72hr, although no radiocarbon was found in the expired CO2. Radiocarbon level in the blood reached the maximum of 4.2 (or 12.5)μg 14C-flutolanil equivalent/ml 2hr after administration, and then rapidly decreased. None of the tissues examined had a high residual radioactivity 72hr after administration (20mg/kg). Small amounts of flutolanil were recovered from both of urine and feces (2.3 and 1.2% of the dose 20mg/kg, respectively). In the case of 20mg/kg, four metabolites identified were 3′-(1-hydroxycarbonylethoxy)-2-(trifluoromethyl)benzanilide (3), 4′-hydroxy-3′-isopropoxy-2-(trifluoromethyl)-benzanilide (4), 3′-hydroxy-2-(trifluoromethyl)benzanilide (5) and 4′-hydroxy-3′-methoxy-2-(trifluoromethyl)benzanilide (8). Their D-glucuronide and/or sulfate conjugates were also detected. The major metabolites were free and conjugated 5, which accounted for 57.5% of the dose (51% in urine and 6.5% in feces). Those in bile accounted for 20% of the dose (20mg/kg), much exceeding the fecal level. This should indicate the deconjugation, reabsorption and resulting exclusive excretion into urine as the sulfate. Metabolism of flutolanil in rats occurs through oxidative O-dealkylation and following conjugation. 4′-Hydroxylation also occurs but is not predominant. There was no evidence for cleavage of the aniline bond or hydroxylation on the 2-(trifluoromethyl)benzoyl ring.
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  • Herbicidal Activity of N-Benzylbutanamides (Part 6)
    Shunichi HASHIMOTO, Osamu KIRINO, Kunihiko FURUZAWA, Hiromichi OHSHIO
    1983 Volume 8 Issue 4 Pages 493-498
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    The herbicidal properties of four N-(α, α-dimethylbenzyl)butanamides including herbicidal spectrum, effect on treatment site, and movement in soil were examined. The herbicidal activity of optically active N-(α, α-dimethylbenzyl)butanamides against purple nutsedge, Cyperus rotundus, was determined by the pot test. N-(1-Methyl-1-phenylethyl)-2-bromo-3, 3-dimethylbutanamide (S-47) showed a broad herbicidal spectrum suppressing purple nutsedge, yellow nutsedge, barnyardgrass, corn, soybean and cotton in the pot test with pre-plant soil incorporation method. The p-methyl derivative of S-47 and N-(1-methyl-1-phenylethyl)-2-ethyl-3, 3-dimethylbutanamide (PEB) exhibited the strong herbicidal activity only against purple nutsedge and did not show any phytotoxicity on crops. All compounds showed considerably large movement in soil. The activity of the d-isomer was higher than that of the l-isomer and the d-isomer of the p-methyl derivative of PEB possessed the highest activity.
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  • Studies on Antiviral Substances for Plant Virus (Part 1)
    Tetsuo NAKAJIMA, Toru TERAOKA, Taichiro SHIGEMATSU, Hiroshi KASUGAI
    1983 Volume 8 Issue 4 Pages 499-503
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    Various kinds of surfactants, polyanions and polycations were tested for their inhibitory activities against TMV infection on tobacco plants (Nicotiana tabacum L. cvs. Xanthi-nc and Bright Yellow). Chemicals were applied on Xanthi-nc before TMV inoculation. Among surfactants tested, α-olefine sulfonate (AOS) showed high activity without causing phytotoxicity. Polyanions other than sodium alginate and sodium polyacrylate (SPA) were less effective. Among polycations tested, poly (2-methacryloxyethyl trimethylammonium chloride) (MEOA·TMC) showed the highest activity without causing phytotoxicity. MOEA·TMC showed higher inhibitory activity against TMV infection on Bright Yellow through infested soil. It was suggested that cationic quaternary ammonium polymers had excellent properties as antiviral substances.
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  • Studies on Antiviral Substances for Plant Virus (Part 2)
    Tetsuo NAKAJIMA, Masatsugu ODA, Toru TERAOKA, Taichiro SHIGEMATSU
    1983 Volume 8 Issue 4 Pages 505-511
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Cationic quaternary ammonium polymers were tested for their antiviral activities against TMV infection on tobacco plants (Nicotiana tabacum L. cvs. Xanthi-nc and Bright Yellow). Chemicals were applied onto leaves of Xanthi-nc prior to TMV inoculation or with TMV inoculum. Among polymethacryloxyalkyl ammonium salts, poly (3-methacryloxy-2-methylpropyl-2-trimethylammonium methylsulfate) (MOBA·TMMS) showed the highest inhibitory activity. Copolymer of dimethyldiallylammonium chloride (MAA) and (3-chloro-2-hydroxy)-propyldiallylammonium hydrochloride (PAA) (MAA/PAA=6, CMPA) was the most effective among polydiallyl ammonium salts. CMPA showed the highest inhibitory activity on Bright Yellow tobacco to TMV infection through the infested soil. It was observed that the degree of flocculation of TMV by CMPA was significantly greater than that by sodium alginate, a known antiviral substance. Furthermore, CMPA was proved to be a stronger antiviral agent than sodium alginate in mixed inoculation method. Whereas, both polymers showed nearly equal antiviral activity in pre-treatment method.
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  • Yoshio HAYASE, Tetsuya TAKAHASHI
    1983 Volume 8 Issue 4 Pages 513-517
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    An aqueous solution of 3-(5-tert-butyl-3-isoxazolyl)-1, 1-dimethylurea at 100μg/ml remained unchanged even when exposed to sunlight or a combination of black light and fluorescent light. However, in the presence of acetone as a sensitizer, more than 60% and 80% of isouron was lost on exposure to sunlight and artificial light for 32hr, respectively. Two products, 3-(5-tert-butylisoxazolyl)-1-methyl-1-formylurea and 3-(5-tert-butylisoxazolyl)-1-methylurea, were isolated and identified by comparison of their nmr and mass spectra with those of synthetic standards. Also, formaldehyde was identified in the photolysis solution by preparing methylenebisdimedone. The formation of formaldehyde suggests that unstable 3-(5-tert-butylisoxazolyl)-1-hydroxymethyl-1-methylurea is an intermediate in the formation of 3-(5-tert-butylisoxazolyl)-1-methylurea. The photolysis of 3-(5-tert-butylisoxazolyl)-1-formyl-1-methylurea also yielded 3-(5-tert-butylisoxazolyl)-1-methylurea.
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  • Paul N. P. CHOW, Alex W. MacGregor
    1983 Volume 8 Issue 4 Pages 519-527
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    The effect of adjuvants including ammonium sulfate and non-ionic surfactants, each at 0.5% of total spray, on sethoxydim {2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)-propyl]-3-hydroxy-2-cyclohexen-1-one} (0.1kg/ha) for controlling wild oat seedlings was examined. Addition of both ammonium sulfate and surfactant (Atplus 411F or Citowett Plus) to sethoxydim gave better control than each one added separately. Of five ammonium and six sulfate ions at 0.04M added to the spray solution, ammonium sulfate with a surfactant gave the best wild oat control by sethoxydim. It was also more effective than ammonium thiocyanate at equivalent concentrations (0.005 to 0.04M). Acidic solutions (pH 4.0 and 6.0) of sethoxydim tended to increase the efficiency of wild oat control compared to slightly alkaline solutions (pH 8.0). However, this pH effect on the activity of sethoxydim disappeared when both ammonium sulfate and Atplus 411F surfactant at 0.5% were added to the herbicide solution. There was a noticeable interaction of ammonium sulfate and sethoxydim on wild oat control. Without addition of Renex-36, ammonium sulfate at high concentrations (0.5 to 2.5%) reduced wild oat control by sethoxydim (0.1kg/ha). When the concentrations of Renex-36 increased from 0.1 to 2.5%, the antagonistic effect of ammonium sulfate on sethoxydim was reduced. Overall, the combination of 0.5% ammonium sulfate and 0.5% Renex-36 with sethoxydim at 0.1kg/ha gave the maximum wild oat control. Increased permeability of corn leaf discs may be associated with increased activity of sethoxydim in the presence of adjuvants. Deposit of epicuticular wax on wild oat leaves was altered when either ammonium sulfate, Atplus 411F or the combination was applied with sethoxydim.
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  • Matazaemon UCHIDA, Yuji OHORI, Tatsuyoshi SUGIMOTO, Hiroyasu AIZAWA
    1983 Volume 8 Issue 4 Pages 529-535
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    [Aniline ring-14C(U)] flutolanil, 3′-isopropoxy-2-(trifluoromethyl) benzanilide, in soils was considerably stable under laboratory conditions, showing the half life of 160-300 days in three soils under flooded condition and 190-320 days under upland condition. Flutolanil decomposition proceeded more rapidly in Tochigi soil of high organic matter content than in Saitama and Okayama soils of low organic matter content and was attributable mainly to the formation of bound residues and 14CO2, which accounted for 9-27% and 3-7%, respectively, of the applied radioactivity after 180 days. Three degradation products in the soils under flooded condition were detected and identified as 4′-hydroxy-3′-isopropoxy-2-(trifluoromethyl)benzanilide, 3′-(hydroxymethyl) ethoxy-2-(trifluoromethyl)benzanilide and 3′-hydroxy-2-(trifluoromethyl)benzanilide. Two additional products such as 3′-methoxy-2-(trifluoromethyl)benzanilide and 4′-hydroxy-3′-methoxy-2-(trifluoromethyl)benzanilide were detected in upland soils.
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  • Matazaemon UCHIDA, Kunihiko OGAWA, Tatsuyoshi SUGIMOTO, Hiroyasu AIZAW ...
    1983 Volume 8 Issue 4 Pages 537-544
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    After [aniline ring-14C(U)] flutolanil [3′-isopropoxy-2-(trifluoromethyl)benzanilide] was applied to paddy water, radioactivity in rice plants increased with time to reach the maximum concentration (93.7ppm 14C-flutolanil equivalent on the basis of dry weight) in the leaf blades within 27 days. Then, it gradually decreased until the leaf blades and the hulled rice contained 83.0 and 0.50ppm 14C-flutolanil equivalent after 81 days. The concentrations of unchanged flutolanil in the leaf blades and hulled rice were 3.14 and 0.03ppm, respectively. Five identified metabolites in rice plants were 4′-hydroxy-3′-isopropoxy-2-(trifluoromethyl)-benzanilide (2), 3′-(hydroxymethyl)ethoxy-2-(trifluoromethyl)benzanilide (3), 3′-hydroxy-2-(trifluoromethyl)benzanilide (4), 4′-hydroxy-3′-methoxy-2-(trifluoromethyl)benzanilide (6) and 3′-methoxy-2-(trifluoromethyl)benzanilide (7). In the aqueous extracts, there existed the conjugates of 2, 3, 4 and 6, among which the conjugated 4 was a major metabolite of flutolanil in rice plants. 14C-Flutolanil applied topically on the leaves of cucumber hardly penetrated into the plant so that 70% of 14C-flutolanil was recovered as the surface wash even after 13 days. Although only 10% of the applied radioactivity was found in cucumber, the metabolites similar to those in rice plants were obtained but in less amounts.
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  • Isamu YAMAGUCHI, Shigeko SEKIDO, Haruo SETO, Tomomasa MISATO
    1983 Volume 8 Issue 4 Pages 545-550
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Scytalone and 2-hydroxyjuglone (2-HJ) are metabolites which greatly accumulate in the culture of Pyricularia oryzae due to the blocking of allo-melanin biosynthesis by such chemicals as tricyclazole or CGA 49104 (pyroquilon). Scytalone was found to be less effective than 2-HJ in reducing the viability of P. oryzae. Thus, effects of 2-HJ on the fungal respiration system and macromolecular syntheses were investigated by using the spheroplasts of P. oryzae. Incorporation of 14C-precursors into acid-precipitable material as well as respiration was inhibited by the compound non-specifically. In contrast, no such inhibitory effects were observed with CGA 49104. While inhibition by 2-HJ was particularly significant in RNA, protein and lipid syntheses, uptake of 14C-uridine or 14C-phenylalanine by spheroplasts was also inhibited by 2-HJ quite markedly, as was seen in the uptake of 14C-glucose. These results suggest that 2-HJ acts on essential biochemical processes and on membrane systems in P. oryzae. Since the fungal appressoria accumulate significant amount of 2-HJ during their maturation in the presence of tricyclazole or pyroquilon, such a metabolite may possibly play a part in the deterioration of the blast fungus pathogenicity.
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  • Naohiko ISOBE, Masatoshi MATSUO, Junshi MIYAMOTO
    1983 Volume 8 Issue 4 Pages 551-559
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Metabolism study of N-(1-methyl-1-phenylethyl)-2-bromo-3, 3-dimethylbutanamide (bromobutide) in mice was carried out as single oral administration (5mg/kg) of 14C-carbonyl labeled bromobutide, and the results were compared with those of rats. Dosed 14C was rapidly excreted into urine (major) and feces (minor) in mice, while in rats dosed 14C was mainly excreted into feces. Levels of 14C-residues in tissues examined in mice were less than 0.1μg bromobutide equivalents per gram tissue and lower than those in rats on the 7th day after administration. The major biotransformations of bromobutide at the initial stage were aromatic hydroxylation in mice and ω-hydroxylation of t-butyl group and aromatic hydroxylation in rats. A glucuronide of p-hydroxylated product of bromobutide, was formed as a common and major product in liver of both species, but was excreted into blood and urine in mice and into bile in rats. These differences in species were presumably derived from different molecular selectivities in mice and rats for biliary secretion of the glucuronide. Judging from the higher quantity of polar metabolites in rats, compounds in bile were subjected to further biotransformation, e. g. debromination in the course of enterohepatic circulation observed. The major bioreaction of bromobutide at the initial stage was suggested to be oxidation, however, ca. 12.4% of bromobutide was estimated to be converted to oxidation products after debromination.
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  • Hikaru KAZANO, Shoichi KOYAMA, SUTRISNO
    1983 Volume 8 Issue 4 Pages 561-565
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Propaphos was metabolized by the green rice leafhopper, Nephotettix cincticeps Uhler and the common cutworm, Spodoptera litura Fabricius to form propaphos sulfoxide, propaphos sulfone, 4-methylsulfinylphenol, 4-methylsulfonylphenol, and unidentified aqueous metabolites. Most of the solvent-soluble metabolites consisted of propaphos, propaphos sulfoxide and propaphos sulfone in the green rice leafhopper. In a case with the common cutworm, formation of hydrolyzed metabolites of propaphos and aqueous metabolites was dominant. Inhibitory activity of propaphos sulfoxide and sulfone to the acetylcholinesterase (AChE) of the green rice leafhopper and the common cutworm larvae homogenates were large enough to exhibit insecticidal effects. However, AChE of the common cutworm topically applied with propaphos was as active as that of untreated insects whereas in a case with the green rice leafhopper, activity of AChE of treated insects decreased compared with that of untreated ones. Thus, insecticidal selectivity of propaphos between two insect species resides in the metabolic difference: Propaphos degraded to non-insecticidal substances in a case with the common cutworm, while the formation of oxidative metabolites which were AChE inhibitors was dominant in the green rice leafhopper.
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  • Decomposition of Organophosphorus Pesticide (Part 4)
    Takayoshi MAEDA, Misako KAWASHIMA, Fumio HORIDE, Kozo TSUJI
    1983 Volume 8 Issue 4 Pages 567-574
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Salithion rearranges thermally into two kinds of isomers, S-methyl-salithion and S-benzyl-salithion, which generate, by further heating, corresponding sulfides such as gaseous dimethyl sulfide and benzyl sulfide derivatives. Thermal degradation of salithion in a closed system proceeds more easily than that in an open system. It was found that these sulfides catalyzed isomerization reaction, and dimethyl sulfide was more effective. Autocatalytic degradation mechanism in which dimethyl sulfide gas is produced from S-methyl-salithion, plays the most important role in a closed system. Successful methods to stabilize salithion against thermal degradation are shown. Their properties are discussed on the basis of their assumed mechanism of stabilization. (i) Storage in a paper bag rather than in a gas-barrier film is suitable, possibly as a result of reduction of dimethyl sulfide accumulation. (ii) Inclusion with β-cyclodextrin is also effective to hinder bimolecular reaction of salithion to produce isomers. (iii) β-Naphtylphenylamine, a stabilizer of salithion, is assumed to be a scavenger of the isomers, which are sources of the active sulfides.
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  • Hirotaka TAKANO, Yukio OGURI, Toshiro KATO
    1983 Volume 8 Issue 4 Pages 575-582
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    The new fungicide, S-3308 [(E)-1-(2, 4-dichlorophenyl)-4, 4-dimethyl-2-(1, 2, 4-triazol-1-yl)-1-penten-3-ol] inhibited sporidial multiplication and caused morphological changes in Ustilago maydis. Sporidia were branched, swollen and multicellular in the presence of 2μg/ml fungicide. Increase in dry weight was inhibited 66% during 8hr incubation. Both endogenous and exogenous respirations were inhibited by S-3308 but a high concentration (100μg/ml) was required for complete inhibition. Syntheses of protein, DNA and RNA were only slightly affected by the fungicide. A relative amount of ergosterol severely decreased in the treated sporidia and the concomitant accumulation of 24-methylenedihydrolanosterol, obtusifoliol and 14α-methyl-Δ8, 24(28)-ergostadienol was observed. Incorporation of 14C-acetate into C-4-desmethyl sterols and sterol esters was inhibited more than 80%. On the contrary, the accumulation of radioactivities in the fractions of 4, 4-dimethyl sterols and C-4-methyl sterols was observed. These results indicate that S-3308 particularly inhibits the demethylation at the C-14 position of 24-methylenedihydrolanosterol in the sterol biosynthetic pathway.
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  • Biological Activity of Cyclic Imide Compounds (Part 7)
    Chiyozo TAKAYAMA, Haruo IMAJO, Osamu KIRINO, Yoshikatsu MIYASHITA, Shi ...
    1983 Volume 8 Issue 4 Pages 583-586
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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  • Shozo ENDO, Takeo MASUDA
    1983 Volume 8 Issue 4 Pages 587-590
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
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    Concentrations of cartap and monocrotophos in rice plants treated with granular formulations at different growth stages were measured, and toxicity of each insecticide, applied to rice plants by root dipping method, to rice leafroller larvae was evaluated. Cartap concentrations in the leaf blades of rice plants at the boot stage and the panicle formation stage reached a maximum of 3.2 and 2.1ppm 3 days after application, respectively, while the concentration of the maximum tillerring stage reached a maximum of 0.94ppm 15 days after application. Concentrations of monocrotophos in the leaf blades of the three stages reached a maximum of 1.4, 2.3 and 2.1ppm 3 days after application, respectively. LC50 values were calculated from mortality and insecticide concentration in the leaf blades, and LC50 (24hr) values in 1st, 3rd and 5th instar larvae for cartap were 0.68, 1.4 and 5.6ppm, and those for monocrotophos 0.60, 1.2 and 4.0ppm, respectively. Periods of exceeding LC50 (24hr) levels for 1st instar larvae of cartap and monocrotophos in the leaf blades were 27 and 10 days at the boot stage, 25 and 9 days at the panicle formation stage and 21 and 11 days at the maximum tillerring stage, respectively.
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  • Mode of Action of Antifeeding Compounds in the Larvae of the Tobacco Cutworm, Spodoptera litura (F.) (Lepidoptera: Noctuidae) (Part 5)
    Alice Girgis ANTONIOUS, Tetsuo SAITO, Tadashi MIYATA
    1983 Volume 8 Issue 4 Pages 591-593
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    Chlordimeform hydrochloride and clerodin showed no inhibitory activity against acetyl-cholinesterase (AChE) from the heads of the 5th instar larvae of the tobacco cutworm when measured radiometrically in vitro. In vivo anti-AChE estimation using a leaf disc method also showed that both antifeeding compounds had no anti-AChE activity. Monoamine oxidase (MAO) activity was not observed in the homogenate of the insect heads. Therefore, it is doubtful that the symptoms caused by the antifeeding compounds are derived from the inhibition of AChE and MAO.
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  • Virapong NOPPUN, Tadashi MIYATA, Tetsuo SAITO
    1983 Volume 8 Issue 4 Pages 595-599
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    As the first step to clarify the mechanism of insecticide resistance, the susceptibility of 4 strains of the diamondback moth against 4 organophosphorus and 2 carbamate insecticides, cartap and fenvalerate were assessed by the topical application method. The results showed that the resistant strains were highly resistant to 3 organophosphorus compounds (phenthoate, prothiophos and cyanophos), moderately to 2 carbamate insecticides (acephate and methomyl) and cartap, but no obvious resistance was observed for dichlorvos and fenvalerate.
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  • Yoshihisa OZOE, Kazuo MOCHIDA, Toshiie NAKAMURA, Atsushi SHIMIZU, Mori ...
    1983 Volume 8 Issue 4 Pages 601-605
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
  • Yuh-Lin CHEN, Tien-Chi WU, Houng-Jaan YEN, Yei-Shung WANG
    1983 Volume 8 Issue 4 Pages 607-611
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    Uptake of isouron by sugarcane plants from soil was more rapid during the first 7 weeks than during the later stage. Specific activity in plants reached a maximum in 4-7 weeks. More than 83% of the radioactivity translocated to leaves after 2 weeks. Larger amount of radioactivity was detected in the young leaves at the earlier stage, but most of the activity was found in the old leaves at the late stage after 7 weeks. Up to 7 weeks, 97.7 to 94.4% of the radioactivities were extractable with methanol-water (2:1) from the leaves. Among them, dichloromethane extractable parts decreased from 73.4 to 26.3%, while water soluble fractions increased from 24.6 to 69.4% as the time elapsed. Since 5.4 to 17.7% of the radioactivities in the aqueous phase were extractable with dichloromethane after acid hydrolysis, the existence of metabolites in conjugated form was suggested.
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  • Toru MIYAMOTO, Kazuki TOEDA, Izuru YAMAMOTO
    1983 Volume 8 Issue 4 Pages 613-617
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    In vitro metabolism of S-(4-chlorophenyl) diethyl phosphorodithioate by rat liver microsomal mixed-function oxidase system gave the metabolites, S-(4-chlorophenyl) S-ethyl ethyl phosphorodithiolate and 4-chlorophenyl diethoxyphosphinyl disulfide, in addition to the oxon. An analytical procedure was developed for analyzing these metabolites which included the derivatization of the unstable phosphinyl disulfide with diazomethane and UV irradiation. Such S-alkyl isomer and phosphinyl disulfide compounds must be considered as the potential bioactive metabolites of thiophosphorus pesticides.
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  • Hideki MORI, Gary M. WILLIAMS
    1983 Volume 8 Issue 4 Pages 619-625
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    Many organochlorine pesticides exert a specific carcinogenic effect on rodent liver, particularly in strains with a high spontaneous background of liver neoplasms. None have been demonstrated to be genotoxic. In contrast, DDT is a liver neoplasm promoter and recently several have been found to inhibit intercellular communication, a property associated with neoplasm promoters. Therefore, it is proposed that these agents produce their liver carcinogenicity through an epigenetic mechanism involving neoplasm promotion. A number of considerations indicate that the hazards of epigenetic carcinogenic agents are distinct from genotoxic carcinogens. Accordingly, the organochlorine pesticides are suggested not to represent a human cancer risk at low levels of exposure.
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  • Izuru YAMAMOTO
    1983 Volume 8 Issue 4 Pages 627-633
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
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  • [in Japanese]
    1983 Volume 8 Issue 4 Pages 635-636
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
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  • [in Japanese], [in Japanese]
    1983 Volume 8 Issue 4 Pages 637
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
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  • [in Japanese]
    1983 Volume 8 Issue 4 Pages 638-641
    Published: November 20, 1983
    Released on J-STAGE: August 05, 2010
    JOURNAL FREE ACCESS
    Download PDF (488K)
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