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Kyo SATO
1987 Volume 12 Issue 4 Pages
589-598
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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Pentachlorophenol(PCP)-tolerance of bacterial strains isolated from percolated soil, where a bacterial flora was changed by applying PCP, was investigated. Pretreatment with PCP did not affect the tolerance of the strains. When they were cultured in media containing different concentrations of their estimated PCP-tolerance level, the strains differed in tolerance according to soil treatment. The tolerance was the highest in the strains isolated from the PCP-percolated soil, medium in those from the PCP and glycine-added soil and the lowest in those from the water-percolated soil. Taxonomical groups of the strains also seemed related with the difference in growth rate when PCP was applied to the tested medium at different concentrations. The nature of media also affected the tolerance of the strains.
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Studies on the Plant Growth Regulatory Activity of Isonicotinanilides (Part 1)
Norio SHIRAKAWA, Hiromi TOMIOKA, Masanori FUKAZAWA, Masaki TAKEUCHI, M ...
1987 Volume 12 Issue 4 Pages
599-607
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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The effects of inabenfide (0.05 to 2g per nursery box) on rice plants were: one, the lengths of the second, third and fourth leaf sheaths significantly shortened; two, the foliage dry weight per cm of plant height, which is an indicator of good rice seedlings, increased; three, both angles of erectness of rice seedlings and α-naphthylamine oxidation increased; and four, the longitudinal length of epidermal cell of the fourth leaf sheath significantly shortened. Inabenfide was most effective for control of culm length when applied 32 days before heading. The lengths of the fourth and fifth internodes greatly shortened at all application times tested. Full ripening, 1000-kernel weight and yield per hectare increased. The relation between the lodging degree and yield was investigated.
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Microbial Metabolism of Chlorinated Nitrobenzenes (Part 3)
Satoshi TAHARA, Zainuddin HAFSAH, Junya MIZUTANI
1987 Volume 12 Issue 4 Pages
609-616
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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Formation of a 2, 4-dichloro-1-nitrobenzene glutathione conjugate [
S-(5-chloro-2-nitrophenyl) glutathione,
2] was confirmed in the cell-free system of
Mucor javanicus which metabolizes 2, 3- and 2, 4-dichloro-1-nitrobenzenes into the corresponding chloro-methylthio-nitrobenzenes or chloro-methylthiobenzenamines. Further metabolisms of
2, the corresponding cysteine conjugate (
3) and 5-chloro-2-nitrobenzenethiol (
4) were investigated. Oxidation products (
S-oxides and
S-dioxides) of the formerly identified methylthio-containing metabolites were isolated from the growing cultures of the fungus administered
2.
S-(5-Chloro-2-nitrophenyl) cysteine (
3) and
N-acetyl-
S-(5-chloro-2-nitrophenyl) cysteine (
7) were newly identified as metabolites of
2 in the resting cell system of the fungus.
View full abstract
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Microbial Metabolism of Chlorinated Nitrobenzenes (Part 4)
Zainuddin HAFSAH, Satoshi TAHARA, Junya MIZUTANI
1987 Volume 12 Issue 4 Pages
617-625
Published: November 20, 1987
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A new metabolic pathway of dichloronitrobenzenes (DCNB) through a glutathione conjugate in
Mucor javanicus was established by using a radio-labeled substrate. In the fungal metabolism of 2, 4-DCNB (
1) (and probably of 2, 3-DCNB as well), the substrate was initially transformed into a corresponding benzenamine (
12) or a glutathione conjugate (
2), and the latter was further metabolized into methylthio-, methylsulfinyl- or methylsulfonyl-substituted monochloronitrobenzene (
5,
8 or
9), or similarly substituted monochlorobenzenamines (
6,
10,
11)
via a cysteine conjugate (
3) and a corresponding benzenethiol (
4). The former (
3) was found to be temporarily
N-acetylated in the fungus and reversively deacetylated. An unstable metabolic intermediate (
4) was successfully trapped by reaction with an alkylthiosulfinate and identified unambiguously.
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Toshiyuki KATAGI, Nobuyoshi MIKAMI, Tadashi MATSUDA, Junshi MIYAMOTO
1987 Volume 12 Issue 4 Pages
627-633
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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Conformations of the plant growth regulator uniconazole (ES pure) [(
S)-
E-1-(4-chlorophenyl)-4, 4-dimethyl-2-(1, 2, 4-triazol-1-yl)-1-penten-3-ol] in a lower energy state were optimized by semi-empirical molecular orbital calculations using the MNDO program. The results indicated that two conformers of uniconazole (ES pure) exist in almost equal proportion, and that they are readily converted into each other. One of the optimized conformers was supported by
1H-NMR and IR spectra, which suggested the formation of an intramolecular hydrogen bond between the hydroxy proton and the nitrogen atom at 2-position of the 1, 2, 4-triazolyl moiety. The substrate difference spectra with rat liver microsomes showed Type II binding and stoichiometrical binding of a racemic mixture of uniconazole (ES pure) to cytochrome
P-450 enzymes was observed. The binding profiles together with the MNDO calculations strongly suggested that the nitrogen atom at 4-position of the 1, 2, 4-triazolyl moiety co-ordinated to the iron atom of the prosthetic porphyrin group in cytochrome
P-450 enzymes. Interaction of uniconazole (ES pure) with cytochrome
P-450 enzymes was discussed from a viewpoint of similarity in molecular shape between uniconazole (ES pure) and (-)-kaur-16-ene, which was an intermediate in gibberellin biosynthesis.
View full abstract
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Studies on Pyrazolate Formulation (Part 2)
Kinji TANIZAWA, Masahiko FUJIMOTO, Katsuhiko KAWAKUBO, Fumito KASAI, T ...
1987 Volume 12 Issue 4 Pages
635-641
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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Relationship between the particle size and the herbicidal activity of pyrazolate was investigated under paddy field conditions. Suspensions containing pyrazolate particles classified into different sizes were tested in a greenhouse. By pre-emergence application, fractions less than 44μm in diameter were effective against
Sagittaria pygmaea at a dose of 0.5kg/ha, while particles larger than 20μm were not active enough against
Echinochloa oryzicola at the same dose. Pyrazolate larger than 10μm in diameter gave unsatisfactory efficacy against
Cyperus serotinus even at a dose of 1kg/ha. As pyrazolate got coarse, the activity decreased more remarkably by post-emergence application. Granules containing 10% pyrazolate were prepared by an extrusion method with the active ingredient pulverized into 1.36, 1.76, 2.03, 2.15, 5.13, or 7.47m
2/g of a specific surface area (
Sw) and applied into pots and paddy fields. In the pot tests, granules containing the coarsest pyrazolate were less effective than others. In the field, granules containing pyrazolate of 2.03 or 2.15m
2/g of
Sw were more effective than those containing either coarser or finer pyrazolate. The results indicate that the herbicidal efficacy of pyrazolate is affected by its particle size, and that pyrazolate should be pulverized into
ca. 2m
2/g of
Sw in order to demonstrate sufficient activity in paddy fields in granule form.
View full abstract
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Studies on Pyrazolate Formulation (Part 3)
Kinji TANIZAWA, Toyokuni HONMA, Fumito KASAI, Katsuhiko KAWAKUBO, Tosh ...
1987 Volume 12 Issue 4 Pages
643-649
Published: November 20, 1987
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The influence of pyrazolate dispersion in paddy water on the herbicidal efficacy was investigated in pot tests without leaching and run-off of paddy water. Four kinds of pyrazolate granules prepared from two different recipes by extruding through screens of 0.6 and 0.9mm∅ were tested before weed emergence. Samples with better dispersion were found to be more effective in these granule sizes. Between two samples with worse dispersion, granules of 0.9mm∅ were less effective than those of 0.6mm∅ against
Cyperus serotinus which is relatively resistant to pyrazolate. Suspensions and granules containing pyrazolate of the same particle sizes were compared in herbicidal activity by treatment before and after fertilization. Granules were inferior to corresponding suspensions, especially when pyrazolate was coarse. The dispersion of granules deteriorated under fertilized conditions. Granules showed poor activity under fertilized conditions. Three samples of pyrazolate granules with different dispersion in paddy water were tested under fertilized conditions. The herbicidal activity increased with enlargement of the dispersion area. The results indicate that the herbicidal efficacy is influenced by the dispersion of pyrazolate in paddy water. The dispersion of granules correlated with the hardness of water, and practical paddy water was considered to correspond to a hardness of less than 10 degrees.
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Studies on Pyrazolate Formulation (Part 4)
Kinji TANIZAWA, Katsuhiko KAWAKUBO, Fumito KASAI, Toshiie NAKAMURA, Mi ...
1987 Volume 12 Issue 4 Pages
651-658
Published: November 20, 1987
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Studies were carried out to investigate the relationship between change in DTP (destosylpyrazolate) concentration in paddy water and herbicidal activity after pyrazolate [4-(2, 4-dichlorobenzoyl)-1, 3-dimethyl-5-pyrazolyl
p-toluenesulfonate] treatment. Pyrazolate of technical grade was pulverized to provide water suspensions A, B and C which contained pyrazolate particles with a surface area of 1.13, 2.68 and 4.25m
2/g, respectively. Granules and microgranules were prepared by the extrusion method using suspension B. Test plots with or without drainage of paddy water were treated with the above five formulations. In paddy water DTP was found immediately after application, and only a small amount of pyrazolate remained throughout the test period, correlation was found between the change in DTP concentrations in paddy water and the herbicidal performance. DTP concentration in a plot treated with suspension A was too low to show sufficient herbicidal efficacy. Suspensions B and C released DTP so fast that the herbicidal efficacy was not persistent under the draining condition, because the active ingredient had run out. The microgranular formulation released DTP in a manner similar to suspension B. A release of DTP was delayed and sustained in the granular formulation and the loss was small enough for DTP to show persistent herbicidal efficacy even under the draining condition.
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Tadashi OHSUMI, Chiyozo TAKAYAMA, Takao MOTOKI, Toshihiko YANO, Masach ...
1987 Volume 12 Issue 4 Pages
659-664
Published: November 20, 1987
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Various kinds of pyrethroids containing a heterocycle in their alcohol moiety were synthesized and their insecticidal activity against
Musca domestica, the housefly was determined by the filter paper contact method. The activity was greatly influenced by the kinds of heterocycles introduced in the alcohol moiety. The stable conformations of these pyrethroids were calculated by the MNDO molecular orbital method and their steric resemblance was studied in the stable conformations. The hydrophobicity of these pyrethroids was also measured by reversed phase HPLC and expressed in terms of log
k′[=log(
tR-
t0)/
t0,
tR: retention time of the
trans isomer of the test compound,
t0: retention time of formamide]. The analysis of the structure-activity relationship by the use of physicochemical parameters and regression analysis showed the importance of molecular shape and hydrophobicity to the insecticidal activity.
View full abstract
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Acaricidal Activity of Chloromethanesulfonamide against Phytophagous Mites (Part 1)
Haruki OGAWA, Tomonori SHIMAZU, Tatsumi NISHIMURA
1987 Volume 12 Issue 4 Pages
665-672
Published: November 20, 1987
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Chloromethanesulfonamide (CMSA) is a systemic acaricidal compound which has stronger activity than dimethoate and disulfoton against the citrus red mite,
Panonychus citri, the two-spotted spider mite,
Tetranychus urticae and the carmine mite,
Tetranychus cinnabarinus. LC
50 values of chloromethanesulfonamide against the larvae, protonymphs, deutonymphs and female adults of
T. cinnabarinus were 74.4, 148.6, 183.1 and 286.6ppm respectively. CMSA showed a systemic acaricidal activity against
P. citri when painted on the trunk and leaf surface of a mandarin orange tree or when applied to the soil surface near the tree. Its toxicity to mammals and carp was low.
View full abstract
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Minoru YOSHIDA, Takanori IKEDA, Makoto IWASAKI, Momiko IKEDA, Takanori ...
1987 Volume 12 Issue 4 Pages
673-681
Published: November 20, 1987
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Male Fischer 344 rats were exposed to 0, 0.37, 0.67, 1.58, or 2.93ppm chloropicrin (CP) vapor for 6hr/day, 5 days/week for 13 weeks. These exposure levels were selected based on the results of a 2-week pilot study. No deaths were observed throughout the 13-week study. Mean body weights of the rats in the 2.93 and 1.58ppm groups were significantly lower than the control values throughout the treatment period. At the end of the treatment period, red blood cell count, hematocrit and hemoglobin concentration significantly increased in the rats of the 2.93ppm group. Lung weights significantly increased in the rats of the 2.93 and 1.58ppm groups. Treatment-related histological lesions were observed only in the respiratory tracts of the rats in the 2.93 and 1.58ppm groups. The major lesions comprised degeneration and necrosis of the bronchial and bronchiolar epitheliums in the rats of the 2.93ppm group, and hypertrophy of them in the rats of the 1.58ppm group. These lesions were more frequently observed in the bronchiole. There were no pronounced adverse effects on daily animal observations, ophthalmology, urinalysis, serum biochemistry and gross pathology. These results indicate that the primary target organ of CP vapor upon repeated inhalation exposure for 13 weeks is the respiratory tract, especially the bronchiole, and that the no-observedadverse-effect level is 0.67ppm.
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Yoshimi YAMADA, Toshihiko YANO, Nobushige ITAYA
1987 Volume 12 Issue 4 Pages
683-688
Published: November 20, 1987
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A new class of organosila-pyrethroids were synthesized and their insecticidal activity was examined against the tobacco cutworm (
Spodoptera litura). Among them, 4-ethoxyphenylsilane derivatives,
e. g. 4-ethoxyphenyl(3-phenoxy-4-fluorobenzyloxymethyl)dimethylsilane, were the most active.
View full abstract
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Masako KOBAYASHI, Katsura YAGI, Hitoshi MORI, Keiko ENDO, Akira K. TAN ...
1987 Volume 12 Issue 4 Pages
689-697
Published: November 20, 1987
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A procedure has been developed for the analysis of residues of benfuracarb and its metabolites, carbofuran, 3-hydroxy-carbofuran (3-OH-CF) and 3-keto-carbofuran (3-C=O-CF) in eleven crops. The crops were homogenized after addition of silver nitrate solution (or milled in a case of rice grain) and extracted with solvents. The extract was cleaned up by column chromatography and subjected to gas chromatography (GC). The silver nitrate solution was used to prevent the decomposition of benfuracarb by N-S bond cleavage during the homogenization and extraction. Of the four compounds benfuracarb and carbofuran were extracted with methanol from the crops. The extract was concentrated, water was added and the extract was again extracted with dichloromethane. The extraction of 3-OH-CF and 3-C=O-CF were accomplished by the aid of hydrolysis of conjugated 3-OH-CF and 3-C=O-CF by dipping the homogenate in 0.25N hydrochloric acid and refluxing, followed by the extraction with dichloromethane. The extract containing benfuracarb and carbofuran or 3-OH-CF and 3-C=O-CF was then subjected to a cleanup procedure using silica gel and Florisil column chromatography. The concentrated eluate was analyzed by GC employing a quartz capillary column. Recoveries from fortified samples were 75-100% for benfuracarb, 73-100% for carbofuran, 76-99% for 3-OH-CF and 76-99% for 3-C=O-CF at 0.05 and 0.5ppm levels. The overall detection limit was 0.005ppm for all compounds.
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Akimichi FURUHATA, Masachika HIRANO, Izumi FUJIMOTO, Masanao MATSUI
1987 Volume 12 Issue 4 Pages
699-704
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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Four kinds of acids generated by conceptual cleavage of a bond between C-1 and C-2 bond in 2, 2, 3, 3-tetramethylcyclopropanecarboxylic acid, the acid part of fenpropathrin, were prepared. Most of their esters with pyrethroidal alcohols did not show insecticidal activity. The insecticidally active esters of 2-isopropyl-3-methyl-3-butenoic acid (
2), a type which is cleaved at the cyclopropane ring between C-2 and C-3 bond, with 3-phenoxybenzyl (
a) and 5-benzyl-3-furylmethyl (
b) alcohols, were converted to ethers and a hydrocarbon. The former showed insecticidal activity to brown planthoppers and green rice leafhoppers, and the latter to carmine mites, while the mother esters did not show the activity to any of these insects. When alcohol part
a,
b or
c of the esters
2 was changed to 2, 4-, 2, 5- or 2, 6-dimethylbenzyl alcohol, the activity was relatively weaker than that of the mother esters.
View full abstract
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Acaricidal Activity of Chloromethanesulfonamide against Phytophagous Mites (Part 2)
Haruki OGAWA, Tomonori SHIMAZU
1987 Volume 12 Issue 4 Pages
705-709
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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An action site of chloromethanesulfonamide (CMSA) against adult females of the citrus red mite,
Panonychus citri, was investigated in laboratory tests. When the body was dipped in CMSA solution CMSA was weaker in toxicity than chlorobenzilate, while when CMSA was topically applied to the back of the hysterosona CMSA was stronger in toxicity than chlorobenzilate. CMSA's vapor action was slight. When the acaricide was painted on the surface of a leaf, on the surface of a parafilm covered leaf and between parafilm and a leaf surface, the LD
50 values of its toxicity taken through the hypostoma were 5.58, 4.26 and 6.10μg/cm
2, respectively. CMSA was also effective in inhibiting oviposition.
View full abstract
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Masanori TOKIEDA, Teruo TACHIBANA, Shigeru KOBAYASHI, Takeshi GOMYO, S ...
1987 Volume 12 Issue 4 Pages
711-719
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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Two analytical methods of determining the residual amounts of hexythiazox [
trans-5-(4-chlorophenyl)-
N-cyclohexyl-4-methyl-2-oxothiazolidine-3-carboxamide; HTZ] and its metabolites, PT-1-2, PT-cy-OH PT-cy-O in crops were investigated. One is the HTZ analytical method for HTZ only and the other the total method for HTZ and its metabolites. By the HTZ method, HTZ was extracted with methanol and purified through liquid-liquid separation and column chromatography, followed by HPLC determination. By the total method, HTZ and its metabolites were extracted with methanol and converted to a decyclohexylaminocarbonyl derivative (PT-1-3) through alkali hydrolysis, followed by column chromatography and HPLC determination. The detection limit by both methods was 0.01ppm and the fortified recovery was more than 80%. Residue analyses of nine crops (12 matrices) suggested that there was no difference in residual amount between both methods. HTZ made up most of the residue in crops and its metabolites were negligible in amount. The results showed that the HTZ analytical method, which is simple and quick, is more suitable. GC was also effective in determining the residual amount of HTZ and its metabolites.
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Naohiko ISOBE, Ayako OHE, Shigemi ITO, Koichi SAITO, Iwao NAKATSUKA, A ...
1987 Volume 12 Issue 4 Pages
721-728
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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On a single oral or subcutaneous administration of 5-methoxy-3-(2-methoxyphenyl)-1, 3, 4-oxadiazol-2(3
H)-one, metoxadiazone (Elemic
®), labeled with
14C at the benzene ring to male and female SD rats at a rate of 1mg/kg,
14C rapidly was excreted mainly into the urine. The cumulative urinary excretion of
14C amounted to 68-75% of the dose within 24hr and reached 80-90% within 7 days.
14C-Recoveries in the feces and expired air within 7 days were 7-18% and 0.1%, respectively.
14C-Levels in the liver, kidney and other tissues reached maximum 0.5-1hr after administration, which were 4.1, 2.0 and <1.0μg metoxadiazone equivalents per g tissue (ppm), respectively. The levels declined rapidly thereafter to below 1.0ppm within 24hr.
14C-Residue levels in the tissues on the 7th day were less than 0.1ppm. The
14C appeared to persist in the blood cell at very low concentrations. Nine metabolites were identified. Main metabolites in the urine were sulfates of
N′-methoxycarbonyl-2-hydroxyphenylhydrazine,
N′-carboxy-2-hydroxyphenylhydrazine and resorcinol. Unmetabolized metoxadiazone was not found either in the urine or feces. Main metabolic transformations of metoxadiazone were hydrolysis of the oxadiazolone ring, demethylation of the methoxyphenyl group and sulfuric acid conjugation.
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Takeshi GOMYO, Hajime KAWAKAMI, Masanori TOKIEDA, Katsumi SUGIOKA, Shi ...
1987 Volume 12 Issue 4 Pages
729-737
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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Two analytical methods for residues of sethoxydim [(±)2-(1-ethoxyiminobutyl)-5-[2-(ethylthio)propyl]-3-hydroxycyclohex-2-enone, STM] and its metabolites in crops, one using HPLC and the other using GC, were investigated. The results by the two method suggested that the HPLC method is more suitable. STM and its metabolites were extracted with methanol. After they were converted into three compounds M2-SO
2, M1-SO
2 and 6-OH-M2-SO
2, the derivatives cleaned up by column chromatography, followed by HPLC determination. The detection limit for STM and its metabolites was 0.05ppm. The recovery of STM and its metabolites ranged from 70 to 96%. The analyses of crops treated with STM showed that a majority of residue was metabolites unified to M2-SO
2 (mainly M-SO and M-SO
2). Hydroxylated metabolites (mainly 5-OH-M-SO
2) unified to 6-OH-M2-SO
2 were detected in a few crops. The residual amount of the metabolites unified to M1-SO
2 was negligibly small in all crops.
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Haruchika SEKIDO, Ritsuo SUGA, Osamu KODAMA, Tadami AKATSUKA, Yoshiki ...
1987 Volume 12 Issue 4 Pages
739-740
Published: November 20, 1987
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Takeshi GOMYO, Shigeo ONO
1987 Volume 12 Issue 4 Pages
741-743
Published: November 20, 1987
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An analytical method for the residue of sethoxydim [(±)2-(1-ethoxyiminobutyl)-5-[2-(ethylthio) propyl]-3-hydroxycyclohex-2-enone, STM] in crops was established using high-performance liquid chromatograph (HPLC). A chopped sample was extracted with 50% aqueous methanol (including 5% Na
2S
2O
3) and STM was transferred to
n-hexane. After extracting with 0.1N NaOH, the extract was acidified by HCl. STM in the acidic solution was extracted with dichloromethane. After concentrating to a certain volume, the solution (10μl) was injected into HPLC. HPLC analysis was carried out on a Zorbax SIL column with a 0.5%MeOH/CH
2Cl
2 elution and with a UV detection of 254nm. The lowest detection limit was 0.02ppm and the recovery was 79.3-83.6%. No STM residue was detected in any crops examined, indicating that the STM was rapidly degraded to metabolites.
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Naohiro TAKAHASHI, Ronald P. MASON
1987 Volume 12 Issue 4 Pages
745-748
Published: November 20, 1987
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Peter BÖGER
1987 Volume 12 Issue 4 Pages
749-757
Published: November 20, 1987
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Shunji TAKEDA
1987 Volume 12 Issue 4 Pages
759-768
Published: November 20, 1987
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[in Japanese]
1987 Volume 12 Issue 4 Pages
771-774
Published: November 20, 1987
Released on J-STAGE: August 05, 2010
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[in Japanese]
1987 Volume 12 Issue 4 Pages
775-779
Published: November 20, 1987
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[in Japanese]
1987 Volume 12 Issue 4 Pages
781-784
Published: November 20, 1987
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[in Japanese]
1987 Volume 12 Issue 4 Pages
785-787
Published: November 20, 1987
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[in Japanese], [in Japanese]
1987 Volume 12 Issue 4 Pages
788-790
Published: November 20, 1987
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[in Japanese], [in Japanese]
1987 Volume 12 Issue 4 Pages
791-792
Published: November 20, 1987
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