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Masanori TOKIEDA, Michihiro OZAWA, Shigeru KOBAYASHI, Takeshi GOMYO, M ...
1999 Volume 24 Issue 2 Pages
115-122
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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Research on the actual residues for acetamiprid, (
E)-
N1-[(6-chloro-3-pyridyl)methyl]-
N2-cyano-
N1-methylacetamidine (ATP) in crops and soils was performed using two analytical methods for determining the residues of ATP and its metabolites. One is the parent analytical method for ATP determination and the other is the common moiety method for ATP and its metabolites (its degradation products) determination in crops and soils. For soil, an individual analytical method for ATP and its degradation products determination was devised. Residue analyses of 8 crops to which water soluble concentrate was applied suggested that there were no remarkable difference in residue amounts obtained from both methods so that ATP made up most of the residue in crops, and its metabolites were negligible in amount. For granule application, residue amounts of ATP and its metabolites obtained from the common moiety method (4 crops) were less than limit of detection (LOD, 0.01ppm) or near the LOD level more than 60 days after treatment. In case of soil, ATP degraded very rapidly and the half life of ATP itself was 1-2 days after treatment in container and field soils, and that of ATP and its degradation products were from 15 to 30 days after treatment in both conditions.
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Oviposition Stimulants for the Cerambycid Beetle, Monochamus alternatus
Masashi SATO, Syed Q. ISLAM, Shinobu AWATA, Toru YAMASAKI
1999 Volume 24 Issue 2 Pages
123-129
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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An oviposition stimulant for the cerambycid beetle,
Monochamus alternatus, from an aqueous acetone extract of inner bark of
Pinus densiflora, was identified as a flavanonol glucoside, (-)-2, 3-
trans-dihydroquercetin-3′-
O-β-D-glucopyranoside. Two dimeric proanthocyanidins, along with polymeric proanthocyanidins, were also isolated from the extract and identified as procyanidins B-1 [epicatechin-(4β→8′)-catechin] and B-3 [catechin-(4α→8′)-catechin]. In the presence of a fraction of the extract, a mixture of the polymers and either B-1 or B-3 stimulated oviposition of the female beetle. However, the glucoside, B-1, B-3 and the polymers were inactive alone.
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Hiroyuki KAI, Tsuneo ICHIBA, Nobuo MIKI, Akira TAKASE, Michio MASUKO
1999 Volume 24 Issue 2 Pages
130-137
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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A series of [2-(2, 5-dimethylphenoxymethyl)-α-methoxyiminobenzyl] isoxazole derivatives were synthesized and their fungicidal activities against crop diseases were assessed. Our studies of the structureactivity relationships revealed that fungicidal activities against cucumber powdery mildew and wheat powdery mildew were the strongest when the isoxazole moiety was comprised of 4, 5-dihydro-3-isoxazolyl, 3-isoxazolyl and 3-methyl-5-isoxazolyl groups. Of the two geometrical isomers at the oxime moiety, the
E-isomers of non-substituted isoxazole derivatives were more active than the
Z-isomers. On the other hand, the
Z-isomers of methyl-substituted isoxazole derivatives were more active than the
E-isomers. Further, [2-(2, 5-dimethylphenoxymethyl)-α-methoxyiminobenzyl] isoxazole derivatives exhibited highly potent respiratory inhibition.
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Nobuhiro KUBOYAMA, Kazuya KOIZUMI, Aiko OHKI, Shinpei OHKI, Hitoshi KO ...
1999 Volume 24 Issue 2 Pages
138-142
Published: May 20, 1999
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A series of 2-aralkylamino-1, 3, 5-triazine derivatives was synthesized and their photosynthetic electron transport (PET) inhibitory activity was evaluated. Investigation on the relationship between PET inhibitory activity and substituents on the triazine ring revealed that 2-benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazine exhibited a highly PET inhibitory activity. Furthermore, introduction of a halogen or a trifluoromethyl group at 3- or 4-position of the benzene ring enhanced PET inhibitory activity, exhibiting pI
50=6.91-7.29. Their PET inhibition was about 10 times stronger than that of simazine. On the absolute configuration of chiral center in 2-methyl-4-(α-methylbenzylamino)6-trifluoromethyl-1, 3, 5-triazine, (-)-enantiomer was around 100 times stronger than (+)- enantiomer. However, the PET inhibitory activity was decreased by
N-alkylation of the benzylamino group in 2-benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazine.
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Keiichi NAGATA, Emi AOYAMA, Tomoko IKEDA, Toshio SHONO
1999 Volume 24 Issue 2 Pages
143-148
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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Nitenpyram, (
E)-
N-(6-chloro-3-pyridylmethyl)-
N-ethyl-
N′-methyl-2-nitro-vinylidenediamine, is known to act on the nicotinic acetylcholine receptor-channel (AChR). We examined the effects of nitenpyram on the neuronal type of the nicotinic AChR in rat clonal phaeochromocytoma PC12 cells using a patch clamp technique to clarify the mechanisms of action at the single-channel level. Nitenpyram itself induced single-channel currents mediated by the neuronal nicotinic AChR. Co-application of ACh and nitenpyram opened the channels exhibiting the two conductance states. The proportion of main conductance levels was decreased and that of subconductance levels was increased in the presence of nitenpyram. The open time and closed time distribution, but not for the burst duration, for the main conductance state currents with co-application of ACh and nitenpyram were similar to those of ACh-induced current. These changes of single-channel kinetics result in a decrease in probability of openings of main conductance state currents explaining the effects of nitenpyram on the neuronal nicotinic AChR. The effects of nitenpyram on the acetylcholine-induced current are deemed directly responsible for the toxic actions in animals.
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Hiroyuki KAI, Tsuneo ICHIBA, Minoru TOMIDA, Michio MASUKO
1999 Volume 24 Issue 2 Pages
149-155
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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A series of 3-(α-alkoxyiminobenzyl)isoxazole derivatives were synthesized and their fungicidal activities against crop diseases were assessed. Studies of the structure-activity relationships revealed the strongest fungicidal activity when the alkoxyimino moiety was substituted with a methyl group. When the position-2 of the benzene ring on the benzyl moiety was substituted with a phenoxymethyl group, a good fungicidal activity was obtained. Among the compounds examined, 3-[2-(2, 5-dimethylphenoxymethyl)-α-methoxyiminobenzyl]isoxazole (
27) showed potent fungicidal activity against cucumber powdery mildew, wheat powdery mildew and wheat eye spot.
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Kenji HIRAI, Tomoyuki YANO, Tomoko MATSUKAWA, Sadayuki UGAI, Shoin NAG ...
1999 Volume 24 Issue 2 Pages
156-169
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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A series of new 3-(substituted phenyl)-5-alkylidene-1, 3-oxazolidine-2, 4-dione derivatives was synthesized by reacting substituted phenyl isocyanates with 2-hydroxy-3-alkenoates prepared through an acid-catalyzed isomerization of 3, 3-disubstituted glycidates, and their herbicidal activities against various weeds as well as the crop safeties were examined. The herbicidal activities of these oxazolidinedione derivatives were primarily influenced by the substituents on the phenyl group and by the structure of the alkylidene moiety. The compounds having a 2, 4-dihalo-5-alkoxyphenyl moiety exhibited relatively higher herbicidal activities while the introduction of a long chain alkylidene group at the 5-position of the oxazolidine ring reduced the activity. The crop safety was found to be markedly affected by the substituent at the 5-position of the phenyl group and a cyclopentyloxy group seemed to be the most preferable one. Among the compounds synthesized, 3-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)-5-isopropylidene-1, 3-oxazolidine-2, 4-dione (KPP-314) was selected as a promising paddy rice herbicide. In green-house pot tests, KPP-314 exhibited an excellent activity against annual lowland weeds by pre- and post-emergence soil treatments at 150 to 450g a.i./ha with a wide safety margin between rice plant and
Echinochloa oryzicola.
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Masato KATAYAMA, Satoko TANAKA
1999 Volume 24 Issue 2 Pages
170-176
Published: May 20, 1999
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N-Phthaloyl-L-threonines (P-Thrs) and their dehydrated phthalimides (2-phthalimido-2-butenoic acids, P-BTEAs) were readily synthesized and showed a strong root growth-promoting activity for rice seedlings. Of the synthetic P-Thrs and P-BTEAs, (Z)-2-phthalimido-2-butenoic acid (P-BTEA,
6a), (Z)-2-(4-chlorophthalimido)-2-butenoic acid (4-ClP-BTEA,
6b) and (Z)-2-(3-fluorophthalimido)-2-butenoic acid (3-FP-BTEA,
6c), in particular, had a strong root growth-promoting activity for rice seedlings. This activity at 1×10
-4M was 3.3- to 3.7-fold the control value. The root growth-promoting activities for rice seedlings of all the dehydrated phthalimides (P-BTEAs) were greater than those of the mother compounds (P-Thrs). For lettuce seedlings 4-ClP-BTEA (
6b) and 4-MeP-BTEA (
6e) alone had a weak root growth-promoting activity at 1×10
-4M. Some P-Thrs and BTEAs caused severe necrosis of lettuce seedling roots and hypocotyls at the high concentration of 1×10
-3M. Nitro-substituted Thrs and BTEAs with strong electron withdrawing group, however, have no root growth-promoting activity.
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Koji IWAYA, Muneyuki MARUYAMA, Hideaki NAKANISHI, Tomoomi ENOMOTO
1999 Volume 24 Issue 2 Pages
177-180
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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Masanori TOKIEDA, Michihiro OZAWA, Takeshi GOMYO
1999 Volume 24 Issue 2 Pages
181-185
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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Satoko UCHIDA, Hajime TANAKA, Koichi FUJIE, Arata KATAYAMA
1999 Volume 24 Issue 2 Pages
186-188
Published: May 20, 1999
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Hiroto TAMURA, Akira MIZUTANI
1999 Volume 24 Issue 2 Pages
189-196
Published: May 20, 1999
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Hideo OHKAWA, Hisae TSUJII, Miyuki SHIMOJI, Yoshiro IMAJUKU, Hiromasa ...
1999 Volume 24 Issue 2 Pages
197-203
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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Cytochrome P450 monooxygenases play an important role in detoxification and/or activation of xenobiotics including agrochemicals as well as in the modes of action of agrochemicals including fungicides, plant growth regulators, insecticide synergists and herbicide safeners. Current genome sequencing revealed that P450 genes are distributed into the five kingdoms of life: bacteria, protoctista, plants, animals and fungi, and a large number of P450 genes occur in animal and plant species. Particularly, Arabidopsis is estimated to have around 400 genes. Biochemical characterization of these P450 enzymes is important for understanding their physiological functions. In higher plants, Arabidopsis T-DNA mutant lines appear to be useful for analysis of their physiological functions. In addition, the yeast expression system is practically important for analysis of their enzymatic functions. Engineering of transgenic plants expressing certain P450 species is also important for crop breeding with useful traits including selective herbicide tolerance and phytoremediation.
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Yoshio KURAHASHI, Shin KUROGOCHI, Noboru MATSUMOTO, Shinzo KAGABU
1999 Volume 24 Issue 2 Pages
204-216
Published: May 20, 1999
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Yukio NEZU, Yoshihiro SAITO, Satoru TAKAHASHI, Yoshinobu TOMODA
1999 Volume 24 Issue 2 Pages
217-229
Published: May 20, 1999
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Takuo WADA, Motohiro HIRAMATU, Mitsuaki TAKENAKA, Yojiro HIROTA
1999 Volume 24 Issue 2 Pages
230-240
Published: May 20, 1999
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Sankyo Company, Limited, Ube Industries, Limited
1999 Volume 24 Issue 2 Pages
241-244
Published: May 20, 1999
Released on J-STAGE: August 05, 2010
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A lot of toxicology studies were carried out in order to investigate toxicological properties of technical pyrimidifen and it's formulation (4%-SC). The results of acute toxicity tests indicate that pyrimidifen technical displays moderate toxicity and it's formulation display much lower toxicity than pyrimidifen technical. Pyrimidifen should be handled carefully because of eye irritation and inhalation toxicity. In chronic toxicity studies, some effects as depression of body weight gain, lower food consumption and small changes in organs were generally observed at higher dose levels. In dogs, clinical signs of liquid faeces and vomiting were also observed at higher dose. In any test and any animal, the NOELs were confirmed.
Pyrimidifen is not genotoxic or oncogenic and does not interfere with normal reproduction and development.
When the rules for usage of pyrimidifen are kept, it is not only an effective acaricide and insecticide but a safe one.
Pyrimidifen is considered to be one of the most useful agricultural materials.
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Technical Department, Cyamamid (Japan) Ltd.
1999 Volume 24 Issue 2 Pages
245-249
Published: May 20, 1999
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Shingo MARUMO
1999 Volume 24 Issue 2 Pages
250
Published: May 20, 1999
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[in Japanese]
1999 Volume 24 Issue 2 Pages
251-252
Published: May 20, 1999
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1999 Volume 24 Issue 2 Pages
e1
Published: 1999
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