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Structure and Fungicidal Activities of New Alkoxyiminoacetamide Derivatives (Part 1)
Takahiro KATAOKA, Yoshio HAYASE, Michio MASUKO, Motomu NIIKAWA, Mitsuh ...
1998 Volume 23 Issue 2 Pages
95-106
Published: May 20, 1998
Released on J-STAGE: August 05, 2010
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A number of alkoxyiminophenylacetamide derivatives were synthesized and their fungicidal activities were examined. Studies of structure-activity relationships revealed strongest fungicidal activity when the alkoxyimino moiety and the acetamide moiety were each substituted with a methyl group. When the 2-position of the benzene ring on the phenylacetamide moiety was substituted with a phenoxy or phenoxymethyl group, good fungicidal activity was obtained. Introduction of other substituents on the benzene ring of the phenylacetamide moiety resulted in decrease of the fungicidal activity. However, introduction of some substituents on the benzene ring of the 2-phenoxy group increased the activity to some extent. Between the two oxime geometrical isomers, the activity of the
E-form was much stronger than that of the
Z-form. Consequently, (
E)-2-methoxyimino-
N-methyl-2-(2-phenoxyphenyl)acetamide was selected as a candidate fungicide for rice diseases.
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Structure and Fungicidal Activities of New Alkoxyiminoacetamide Derivatives (Part 2)
Hideyuki TAKENAKA, Mitsuhiro ICHINARI, Norihiko TANIMOTO, Yoshio HAYAS ...
1998 Volume 23 Issue 2 Pages
107-112
Published: May 20, 1998
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A number of 2-(substituted phenoxymethyl)phenyl-2-methoxy iminoacetamides were synthesized and their fungicidal activities were examined. The strength of activities and fungicidal spectra varied markedly depending upon the substituents on the benzene ring of the 2-phenoxymethyl group of phenylacetamide moiety. Incorporation of either one or two substituent(s) at 2-, 3-, 4- and/or 5-positions on the benzene ring resulted in an increase of fungicidal activity compared to the unsubstituted compound. However, introduction of a bulky substituent at the 2-position or simultaneous substitution at 2- and 6-positions resulted in decrease of activity. When 2- and 4-, or 2- and 5-positions of the benzene ring were substituted with chlorine and/or methyl groups, in addition to the 2, 5-difluoro derivative (
30), the activities were excellent against wheat powdery mildew, cucumber powdery mildew, cucumber gray mold and cucumber downy mildew. Between the two geometrical isomers, the
E-form was much stronger than the
Z-form.
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Georg SCHNURR, Peter BÖGER, Gerhard SANDMANN
1998 Volume 23 Issue 2 Pages
113-116
Published: May 20, 1998
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The carotenogenic enzyme lycopene β-cyclase is found in bacteria, algae and higher plants. The only purified lycopene cyclase to date, originally from the bacterium
Erwinia uredovora, was obtained from transformed
Escherichia coli and used for cell-free inhibitor studies. Sulfuryl reagents and argininemodifying compounds did not affect enzyme activity. However, 2-(4-methylphenoxy)triethylamine (MPTA), the piperidine carboxylate AMO 1618 (2-isopropyl-4-dimethylamino-5-methylphenyl-1-piperidinecarboxylate methylchloride) and nicotine were effective inhibitors. I
50 values for MPTA and nicotine were determined as 12 and 4.8μM, respectively. The type of inhibition of lycopene cyclase by MPTA was non-competitive with respect to the substrate lycopene and also to the cofactor NADH. Except for the sensitivity against sulfuryl reagents, the results on inhibition properties of the
E. uredovora lycopene cyclase resemble qualitatively and quantitatively those of the cyanobacterial and higher plant enzyme. Consequently, the expressed and purified lycopene cyclase from this bacterium can be used as a model enzyme to assay potential herbicides which interact with the corresponding plant enzyme.
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Akiko NAKAMURA, Aki SAGISAKA, Miki SAKAGUCHI, Koichi SUZUKI, Eiichi KU ...
1998 Volume 23 Issue 2 Pages
117-122
Published: May 20, 1998
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A series of 1-(substituted phenoxyalkyl)imidazoles was prepared and evaluated for their activity to induce precocious metamorphosis in larvae of the silkworm,
Bombyx mori, and to terminate diapause in pharate first-instar larvae of the wild silkmoth,
Antheraea yamamai. Of the compounds tested, 1-[7-(4-ethylphenoxy)heptyl] imidazole (
6) and its 4-methylphenoxy analog were the most active against
B. mori larvae. Neither methoprene, a juvenile hormone mimic, nor tebufenozide, an ecdysteroid mimic, could fully counteract precocious metamorphosis induced by compound 6, but both hormone agonists were necessary for complete rescue. A variety of 1-(substituted phenoxyalkyl)imidazoles at 1μg terminated diapause of
A. yamamai at a percentage higher than 90%. 1-[5-(4-Ethylphenoxy)pentyl] imidazole (
4) was the most effective. There was no apparent correlation between the ability of 1-substituted Imidazoles to cause precocious metamorphosis in
B. mori and diapause-terminating activity in
A. yamamai.
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Kyoko KIRIBUCHI, Debra Y. DUNLAP, Fumio MATSUMURA, Isamu YAMAGUCHI
1998 Volume 23 Issue 2 Pages
123-128
Published: May 20, 1998
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Plants are known to activate specific defense mechanisms in response to invasion by pathogens and environmental stresses. We examined the possibility of utilizing the changes in the amounts of protein kinase C (PKC) and its associated components of this signal transduction pathway as a biomarker of exposure of plants to the stress factors, using young rice plants as a model and a Western blotting method as the experimental tool. Preliminary studies have shown that PKC is a consistently more sensitive marker of exposure to a variety of environmental stress factors as compared to phospholipase C (PLC) or G-protein. The titer of PKC increased as a result of exposure to herbicides, low concentrations of copper, fungicides and other chemicals. The same trend was observed when rice plants were stressed by severe physical treatment such as broken stems, deprivation of sunlight and transplantation. On the other hand, PKC levels decreased upon exposure to high winds and high concentration of copper. The most drastic rise in PKC was observed when rice plants were inoculated with the rice blast fungus
Pyricularia oryzae. As expected, several plant protectants against the fungal invasion also induce a rise in PKC.
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Fungicidal and Plant Growth Inhibitory Activities
Toshihide SAISHOJI, Atsushi ITO, Satoru KUMAZAWA, Hiroshi CHUMAN
1998 Volume 23 Issue 2 Pages
129-136
Published: May 20, 1998
Released on J-STAGE: August 05, 2010
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Enantiomers of a seed treatment fungicide, ipconazole, (1
RS, 2
SR, 5
RS; 1
RS, 2
SR, 5
SR)-2-(4-Chlorobenzyl)-5-isopropyl-1-(1
H-1, 2, 4-triazol-1-ylmethyl)cyclopentanol, and its related compounds which have no or differing alkyl groups at the fifth position on the cyclopentane ring in place of the isopropyl group were prepared, and their fungicidal and plant growth inhibitory activities were examined. Of the eighteen enantiomers tested, high fungicidal activity was observed for nine enantiomers with identical absolute configuration types. Two fungicidal enantiomers substituted with no alkyl group or a methyl group (I-B and II-B, respectively) retarded the growth of wheat and cucumber. The other enantiomers did not affect the growth of wheat or cucumber except non-fungicidal enantiomers substituted with an ethyl group, which caused growth inhibition of wheat seedlings. The morphology of plants treated with I-B or II-B was similar to that of plants treated with uniconazole, a known gibberellin biosynthesis inhibitor.
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Shinkichi TAWATA, Shigehiko TAIRA, Hirofumi KIKIZU, Naotada KOBAMOTO, ...
1998 Volume 23 Issue 2 Pages
137-140
Published: May 20, 1998
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Seiko IMAIZUMI, Atsushi TATENO, Takane FUJIMORI
1998 Volume 23 Issue 2 Pages
141-144
Published: May 20, 1998
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Its Selection Based on Stereoisomer-Activity Relationships
Shinzo KAGABU, Yoshio KURAHASHI
1998 Volume 23 Issue 2 Pages
145-147
Published: May 20, 1998
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Koichiro WATANABE, Ryuko TAKEYA, Naotaka YAMADA, Eiichi KUWANO
1998 Volume 23 Issue 2 Pages
148-150
Published: May 20, 1998
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Tomoki NISHINO, Takane FUJIMORI
1998 Volume 23 Issue 2 Pages
151-154
Published: May 20, 1998
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Ryoichi SATO
1998 Volume 23 Issue 2 Pages
155-165
Published: May 20, 1998
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Hideo OKAMURA, Isao AOYAMA
1998 Volume 23 Issue 2 Pages
166-173
Published: May 20, 1998
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Tohru KOYANAGI, Osamu IMAI, Kiyomitsu YOSHIDA
1998 Volume 23 Issue 2 Pages
174-183
Published: May 20, 1998
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Toshiaki SATO, Katsushi MORIMOTO, Shigeomi WATANABE, Richard C. DIRKS
1998 Volume 23 Issue 2 Pages
184-192
Published: May 20, 1998
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Hidemitsu TAKAHASHI, Nobuo TAKAKUSA, Junji SUZUKI, Takashi KISHIMOTO
1998 Volume 23 Issue 2 Pages
193-200
Published: May 20, 1998
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[in Japanese]
1998 Volume 23 Issue 2 Pages
201-205
Published: May 20, 1998
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Market Development, AgrEvo Japan Limited
1998 Volume 23 Issue 2 Pages
206-212
Published: May 20, 1998
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The results of studies showed that acrinathrin demonstrated low mammalian toxicity following acute oral, dermal or inhalation exposure. The results obtained support those already known for other pyrethroids in particular the cyano-pyrethroids.
No irritation was observed in the skin and eye of rabbits treated with acrinathrin technical, while very slight and reversible irritation was noted following treatment with WP formulation. No ocular irritation was observed with the diluted solution of WP formulation. Both acrinathrin technical and WP formulation were negative in skin sensitisation studies conducted by Maximization method.
Acrinathrin did not show mutagenic potential, was not oncogenic in rats and mice and did not affect reproduction of two generations in rats.
Acrinathrin exhibited no teratogenic potential in rats and rabbits.
Main effects observed in subchronic toxicity studies through chronic toxicity studies were the decrease of body weight gain and food consumption, and skin lesions seen at high dose levels in rats and mice dietary studies. The skin lesions persisted with an itching and scratching phenomenon due to paresthetic changes, which were considered to be related to the pharmacological property of acrinathrin and it seems probable that it is brought about by an action of the substance on sodium channels and depolarisation of the sensory nerves. The findings in the reproduction study indicate that the effects are reversible and result in no permanent changes.
Through these long term studies, the overall NOAEL for acrinathrin was determined to be 15ppm (2.49mg/kg/day) in the oncogenicity study in mice.
ARDENT
® 3% WP was registered by Japanese MAFF in 1995 as the insecticide with miticidal activity for various crops including vegetables, fruits, tea as well as ornamental. When used in accordance with label directions, acrinathrin and its formulation will not adversely affect human health.
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[in Japanese]
1998 Volume 23 Issue 2 Pages
213-214
Published: May 20, 1998
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[in Japanese]
1998 Volume 23 Issue 2 Pages
215-217
Published: May 20, 1998
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[in Japanese]
1998 Volume 23 Issue 2 Pages
218-220
Published: May 20, 1998
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