Journal of Pesticide Science

Synthesis and Activity of Novel Acaricidal/Insecticidal 2, 4-Diphenyl-1, 3-oxazolines

Junji SUZUKI, Tatsuya ISHIDA, Yasuo KIKUCHI, Yoshiaki ITO, Chiharu MOR ...

2002 Volume 27 Issue 1 Pages 1-8
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.1

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A series of substituted 2, 4-diphenyl-1, 3-oxazolines were synthesized and their acaricidal and insecticidal activities were examined. When either or both of the ortho-positions of the 2-phenyl group was substituted with halogen(s), an acaricidal activity against two-spotted spider mites (Tetranychus urticae) was observed as an effect on their eggs (ovicidal activity). Hydrophobic substituents at the para-position of the 4-phenyl group of 2-(2, 6-difluorophenyl)-4-phenyl-1, 3-oxazoline enhanced the acaricidal activity, and induced an insecticidal activity against green rice leafhoppers (Neophotettix cincticeps), diamondback moths (Plutella xylostella), and green peach aphids (Myzus persicae). When the 1, 3-oxazoline ring was exchanged to either 1, 3-oxazole or 4-methyl-1, 3-oxazoline, both acaricidal and insecticidal activities were significantly decreased.

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Mechanism of the Phytotoxic Action of Herbicidal N-Isobutyl-N-(4-substituted benzyl)-4-halo-2-pentenamides

Kenji MATSUNARI, Tsutomu SHIMIZU, Fumitaka YOSHIDA, Toshio FUJITA

2002 Volume 27 Issue 1 Pages 9-16
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.9

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The N-isobutyl-N-(4-substituted benzyl)-4-halo-2-pentenamides show a potent light-dependent herbicidal activity against the barnyard grasses. The herbicidal mechanism was investigated with assay systems using cotton seedlings and an enzyme preparation from them as well as cultured unicelluar microalgae. Besides the protoporphyrinogen oxidase inhibition, some other mechanism(s) inhibiting step(s) involved in the chlorophyll biosynthetic pathway were suggested as the origin of the phytotoxicity.

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Effects of Enantiomers of Inabenfide [4′-Chloro-2′-(α-hydroxybenzyl)isonicotinanilide] on Growth, Lodging and Yield Components of Rice (Oryza sativa)

Masanori FUKAZAWA, Yoshikazu KUMAGAI, Takuma MIKI, Keirou ISHIHARA, Ma ...

2002 Volume 27 Issue 1 Pages 17-23
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.17

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We examined the growth regulating activities of enantiomers of inabenfide [4′-chloro-2′-(α-hydroxybenzyl)isonicotinanilide, 82211-24-3 (CAS RN Number)], an inhibitor of gibberellin biosynthesis, on rice plants (Oryza sativa L. cv. Koshihikari) with pot and field experiments. The (S)-form of inabenfide was more effective in reducing culm length than the racemate, whereas the (R)-form showed little effect. In treatment during the tillering stage, the (S)-form was about two times as potent as inabenfide (racemate) in its dwarfing effects on culms but also reduced the spikelet density to a greater extent than did the racemate. In addition, in treatments near the heading stage, the (S)-form (0.06g/m²) reduced culm length, especially at the upper internodes, by 15% of the control and decreased the degree of lodging at maturity, whereas the racemate (0.24g/m²) showed a lesser dwarfing effect. We conclude that: (1) the (S)-form is the active ingredient of inabenfide in reducing the culm length and lodging of rice plants.; (2) the (S)-form may be absorbed and translocated to elongating upper internodes more rapidly than Inabenfide when applied near the heading stage.; and (3) treatment with the (S)-form near the heading stage will reduce the amount of ingredient required.

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Soil Core Test, a Method of Pesticide Leaching Assessment for Upland Field

Kazuhiro OGIYAMA, Yasushi KAKUTA, Kaoru TANAKA, Yoshiyuki TAKAHASHI, T ...

2002 Volume 27 Issue 1 Pages 24-30
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.24

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A vertical infiltration of pesticides in upland field was evaluated by a soil core method. Surface soil layer (0-10cm) was collected by a soil core collector (10cm diameter, stainless steel) from an upland field treated with metalaxyl (Ridmil MZ^®/WP), metolachlor (Dual^®/EC) and bromacil(Hyper X^®/WP). A steel cylinder loaded with vertically divided acrylic resin liner (5cm inner diameter, 3mm thickness) was guarded by stainless pipe (10cm inner diameter, 10cm height) and was driven to 50cm under the surface. By this sampling method, the soil core from 10cm to 50cm layers was collected to be free from the contamination with pesticides in surface soil. The soil cores in acrylic resin liner collected from 6 spots in the field were divided in 10cm soil layers, and mixed thoroughly for each layer. Soil water in each soil layer was separated by centrifugation at 11, 000rpm for 60min at 4°C. The concentration of bromacil in soil water from 40-50cm soil layer was 0.114mg/L at 105 days after the pesticide application, while metalaxyl and metolachlor were not detected in soil water below 30cm depth. No leaching water of pan-lysimeter was collected from the depth of 50cm-soil layer. The leaching water in porous-cup laid at the depth of 50cm did not contain any pesticide.

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Physiological Effects of Thiobencarb Stress in the Eel (Anguilla anguilla)

Cristina FERNÁNDEZ-VEGA, Encarna SANCHO, Dolores FERRANDO, Enri ...

2002 Volume 27 Issue 1 Pages 31-38
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.31

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The effects of thiobencarb (0.22mg/l) on the intermediary metabolism of the European eel, Anguilla anguilla, and its recovery from intoxication were evaluated. Physiological measurements were made in plasma, muscle and liver of the eels during exposure and after an 8-day recovery period in noncontaminated water. Hyperglycemia was detected during exposure, while liver and muscle glycogen levels decreased markedly. Blood lipid values increased, however, a decrease of the lipidic reserves was determined in liver tissue. Mobilization of proteins was detected specially in muscle tissue. Most of the metabolic disorders persisted after eight days in clean water. The observed effects of thiobencarb on intermediate metabolism are discussed in relation to a stress syndrome, as an indicative status of the physiological adaptability of the fish to compensate pesticide stress.

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Herbicidal Activity and Characteristics of Pyraflufen-ethyl for Controlling Broad-leaved Weeds in Cereals

Pyraflufen-ethyl: A Potent Protox Inhibiting Herbicide (Part 1)

Tsutomu MABUCHI, Yuzo MIURA, Takashi OHTSUKA

2002 Volume 27 Issue 1 Pages 39-46
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.39

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Pyraflufen-ethyl [ET-751, ethyl 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxyacetate] is a potent Protox inhibiting herbicide which is also designated as a peroxidizing or photobleaching herbicide. In this paper, we demonstrated the herbicidal activity and characteristics of pyraflufen-ethyl as a cereal herbicide. Pyraflufen-ethyl showed excellent selectivity between cereal crops (wheat and barley) and abroad range of important broad-leaved weeds in post-emergence application. Its herbicidal activity was significantly higher than that of the existing cereal herbicides such as bifenox, ioxynil and mecoprop-p and comparable or even superior to carfentrazon-ethyl and metsulfuron-methyl, which are known as low use-rate herbicides. Pyraflufen-ethyl was also characterized by the fast herbicidal action and excellent activity against Galium aparine, one of the most troublesome broad-leaved weeds infested in winter cereal fields in West Europe. Field trials conducted in U. K. and France in 1990/1991 proved that pyraflufen-ethyl possessed high potentiality as a post-emergence cereal herbicide for controlling broad-leaved weeds selectively at rates of 6-12g a. i./ha.

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Mechanisms of Selective Action of a Protoporphyrinogen IX Oxidase-Inhibiting Herbicide Pyraflufen-ethyl between Wheat (Triticum aestivum) and Cleavers (Galium aparine)

Pyraflufen-ethyl: A Potent Protox Inhibiting Herbicide (Part 2)

Shinji MURATA, Aki YAMASHITA, Yukio KIMURA, Kazuhiko MOTOBA, Tsutomu M ...

2002 Volume 27 Issue 1 Pages 47-52
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.47

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To elucidate the mechanisms of selective herbicidal action of pyraflufen-ethyl [ethyl 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxyacetate], the intrinsic activity on the target enzyme, foliar deposition and absorption, and metabolism of the compound were compared between wheat (Triticum aestivum L.) and cleavers (Galium aparine L.). Although protoporphyrinogen IX oxidase activities from wheat and cleavers chloroplasts were almost equally inhibited by pyraflufenethyl, a foliar application of the compound caused much more accumulation of protoporphyrin IX in cleavers than in wheat. The foliar deposition and absorption of the compound were much greater in cleavers than in wheat. Metabolic detoxification in wheat was much greater than that in cleavers. These differences in foliar deposition and absorption, and in the rate of metabolic detoxification would play an important role in the accumulation of protoporphyrin IX and the resulting selectivity of pyraflufen-ethyl between wheat and cleavers.

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Synthesis and Herbicidal Activity of 1H-2, 3-Benzoxazine Derivatives

Hiroyuki KAI, Minoru TOMIDA, Toru NAKAI, Yukio HORITA, Yoshito UEYAMA, ...

2002 Volume 27 Issue 1 Pages 53-58
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.53

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A series of 1H-2, 3-benzoxazine derivatives were synthesized and their herbicidal activity against upland weeds and selectivity against crops were assessed. Studies of the structure-activity relationship revealed that the strongest herbicidal activity was achieved when position-4 in the benzoxazine ring was substituted with a 3-chloro-4-fluorophenyl or a 3-bromo-4-fluorophenyl group. The treated weeds showed a strong bleaching symptom. Among the compounds examined, 4-(3-chloro-4-fluorophenyl)-1H-2, 3-benzoxazine (23) and 4-(3-bromo-4-fluorophenyl)-6-fluoro-1H-2, 3-benzoxazine (34), applied at 1.0kg a. i./ha, showed strong pre-emergence herbicidal activity against upland weeds such as Echinochloa crus-galli and Digitaria ciliaris without affecting soybean.

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Influence of Fenitrothion-Exposure on the Metabolic Activity of a Rotifer (Brachionus plicatilis) to Organophosphorus Insecticides

Shosaku KASHIWADA, Kazuo MOCHIDA, Yuriko ADACHI, Satomi KIMURA, Yoshih ...

2002 Volume 27 Issue 1 Pages 59-63
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.59

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Chemical Identification of Fusicoccins from a Japanese Isolate Niigata 2 of Peach Fusicoccum Canker Fungus (Phomopsis amygdali) and Production of 3′-Deacetylfusicoccin A by the Fungus

Naoto TAJIMA, Hiroko KUME, Satoko KANEMATSU, Nobuo KATO, Takeshi SASSA

2002 Volume 27 Issue 1 Pages 64-67
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.64

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Plant Growth-Regulating Activities of 4-Chloroindole-3-acetic Acid and Its Esters

Masato KATAYAMA, Hiroyuki HATTORI, Yasuo KAMURO

2002 Volume 27 Issue 1 Pages 68-70
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.68

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Applications of Accelerator Mass Spectrometry (AMS) to Biochemical Studies

Masahiro MIYASHITA

2002 Volume 27 Issue 1 Pages 71-76
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.71

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Useful Reactions for the Pesticide Synthesis

Esterification, Amidation, and Sulfonylation

Yoo TANABE

2002 Volume 27 Issue 1 Pages 77-80
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.77

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Biodegradation Mechanisms of Pesticide Adjuvants Studied by Mass Spectrometry

Hiroaki SATO

2002 Volume 27 Issue 1 Pages 81-83
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.81

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Background of the Studies with Carpaopamid as a Plant Resistance Inducer against Rice Blast

Yasuo ARAKI

2002 Volume 27 Issue 1 Pages 84-87
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.84

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Various Facets of Bioactive Structure (2)

Toshio FUJITA

2002 Volume 27 Issue 1 Pages 88-89
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.88

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Symposia

2002 Volume 27 Issue 1 Pages 90-91
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.90

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[title in Japanese]

[in Japanese]

2002 Volume 27 Issue 1 Pages 92
Published: February 20, 2002
Released on J-STAGE: August 05, 2010

DOIhttps://doi.org/10.1584/jpestics.27.92

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