1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as Potential New Insecticides

Kagabu, Shinzo; Moriya, Keiichi; Shibuya, Katsuhiko; Hattori, Yoshikazu; Tsuboi, Sadao; Shiokawa, Kohzoh

doi:10.1271/bbb.56.362

Cited by 87 publications

(42 citation statements)

References 2 publications

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“…Neonicotinoids such as those shown in Figure 1 are relatively new insecticides structurally related each other, and are originated from imidacloprid, which has been put on the market since 1992 [1–3]. Neonicotinoid insecticides are similar to nicotinoids in binding to the nicotinic acetylcholine receptor of insects [4,5].…”

Section: Introductionmentioning

confidence: 99%

Development of Immunoassay Based on Monoclonal Antibody Reacted with the Neonicotinoid Insecticides Clothianidin and Dinotefuran

Uchigashima

Watanabe

Ito

et al. 2012

Sensors

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Enzyme-linked immunosorbent assay (ELISA) based on a monoclonal antibody (MoAb) was developed for the neonicotinoid insecticide clothianidin. A new clothianidin hapten (3-[5-(3-methyl-2-nitroguanidinomethyl)-1,3-thiazol-2-ylthio] propionic acid) was synthesized and conjugated to keyhole limpet hemocyanin, and was used for monoclonal antibody preparation. The resulting MoAb CTN-16A3-13 was characterized by a direct competitive ELISA (dc-ELISA). The 50% of inhibition concentration value with clothianidin was 4.4 ng/mL, and the working range was 1.5–15 ng/mL. The antibody showed high cross-reactivity (64%) to dinotefuran among the structurally related neonicotinoid insecticides. The recovery examinations of clothianidin for cucumber, tomato and apple showed highly agreement with the spiked concentrations; the recovery rate was between 104% and 124% and the coefficient of variation value was between 1.8% and 15%. Although the recovery rate of the dc-ELISA was slightly higher than that of HPLC analysis, the difference was small enough to accept the dc-ELISA as a useful method for residue analysis of clothianidin in garden crops.

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Section: Introductionmentioning

confidence: 99%

Development of Immunoassay Based on Monoclonal Antibody Reacted with the Neonicotinoid Insecticides Clothianidin and Dinotefuran

Uchigashima

Watanabe

Ito

et al. 2012

Sensors

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“…After 8 h of stirring, the solution was treated with 100 mL of water, and extracted with chloroform (3 × 30 mL). The organic layer was dried over Na 2 SO 4 and concentrated to afford compound 5 as a yellow liquid (Kagabu et al, 1992), which was directly used in the next step (yield 3.34 g, 90%); GC-MS: m/z 185 [M] + , 155, 126, 99, 90.…”

Section: Methodsmentioning

confidence: 99%

Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids

Liu¹,

Yi²,

Zhang

2012

Heterocyclic Communications

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“…To the reaction mixture Baylis-Hillman acetate2a-s (1.0 mmol) in 5 mL THF was added and stirred at room temperature for 2-4 h. Completion of the reaction was monitored by TLC. After completion of the reaction, the mixture was poured in to NH 4 Cl solution and extracted with ethyl acetate. Combined organic layers were washed with brine solution and dried over Na 2 SO 4 , evaporated and purified by silica gel column chromatography to obtain the desired products; Baylis-Hillman derived N-cinnamyl substituted nitro methylene imidazole derivatives 4a-s. methyl3-(4-bromophenyl)-2-(((E) -2 -(nitro methylene) imidazolidin-1-yl) methyl 3 -(3-chlorophenyl)-2 -(((E)-2-(nitro methylene) imidazolidin-1yl) -1-yl) zolidin-1-yl) methyl)-3-(4-nitrophenyl) …”

Section: International Journal Of Pharmaceutical Sciences and Researcmentioning

confidence: 99%

Untitled

2015

IJPSR

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ABSTRACT:A series of Baylis-Hillman derived N-cinnamyl substituted nitro methylene imidazole derivatives 4a-swere synthesizedfrom BaylisHillman acetates and nitro methylene imidazole compoundsand characterised by 1 H NMR, IR, Mass and HRMS spectroscopy. Their insecticidal activities were evaluated against T. Castaneum and compared with a standard insecticide Permethrane. Preliminary biological activity tests showed that most of the compounds exhibited good insecticidal activity against T. Castaneum at 100µg/cm 2 especially compounds 4b, 4g, 4i, 4l, 4n and 4r showed good insecticidal activity against T. castaneum, interestingly compound 4b with p-fluoro substitution displayed 75% activity. The structure-activity relationship showed that compounds with electron-with drawing substitutions like -F, -Br, -Cl, -NO 2 , -CF 3 at the para position havinggood insecticidal activity and compounds with electron-with drawing groups like -F, -Br at the meta position have shown moderate activity.This work provides some hints for further structural modifications on the Baylis-Hillman derivatives and the enhancement of insecticidal activity.

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1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as Potential New Insecticides

Cited by 87 publications

References 2 publications

Development of Immunoassay Based on Monoclonal Antibody Reacted with the Neonicotinoid Insecticides Clothianidin and Dinotefuran

Development of Immunoassay Based on Monoclonal Antibody Reacted with the Neonicotinoid Insecticides Clothianidin and Dinotefuran

Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids

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