Chemistry of Clothianidin and Related Compounds

Uneme, Hideki

doi:10.1021/jf1024938

Cited by 84 publications

(44 citation statements)

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“…1). As its biological advantages, potent activity against Diptera, Coleoptera, and Lepidoptera pests in addition to Hemiptera and Thysanoptera, long-term control effect, excellent systemic action, and a wide variety of treatment methods can be pointed out (Uneme 2011). Neonicotinoids are the most important chemical class of insecticides introduced to the global market since synthetic pyrethroids.…”

Section: Introductionmentioning

confidence: 99%

Application of Catalytic Hydrogen Evolution in the Presence of Neonicotinoid Insecticide Clothianidin

2011

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Clothianidin, a new generation of pesticide, was determined in spiked tap water, apple juice, and soil by square-wave adsorptive stripping voltammetry. The method of determination is based on the hydrogen evolution reaction catalyzed by clothianidin at the hanging mercury drop electrode. The optimal signal was detected at −1.4 V versus Ag/AgCl in citrate buffer at pH 2.2. Various parameters such as pH, buffer concentration, frequency, amplitude, step potential, accumulation time, and potential were investigated to enhance the sensitivity of the determination. The optimal results were recorded at an accumulation potential of −0.35 V, accumulation time of 7 s, amplitude of 100 mV, frequency of 200 Hz, and step potential of 7 mV. The mechanism of catalytic hydrogen evolution was considered under experimental and theoretical conditions. This electroanalytical procedure enabled to determine clothianidin in the concentration range 9×10 −9 -4×10 −6 mol L −1 in supporting electrolyte and tap water, 1×10 −7 -4×10 −6 mol L −1 in diluted apple juice, and 2× 10 −7 -1×10 −6 mol L −1 in soil. The detection and quantification limits in supporting electrolyte and diluted apple juice were found to be 2.6×10 −9 , 8.6×10 −9 and 3×10 −8 , and 1×10 −7 mol L −1 , respectively. A standard addition method was successfully used to determine clothianidin in spiked tap water, spiked apple juice, and spiked soil.

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Section: Introductionmentioning

confidence: 99%

Application of Catalytic Hydrogen Evolution in the Presence of Neonicotinoid Insecticide Clothianidin

2011

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“…2,3 Thiamethoxam is presently one of the most effective chemicals for the control of sucking pests such as aphids, whiteflies, thrips, some micro lepidoptera and a number of coleopteran species. The compound shows contact as well as exceptional systemic activity and is recommended for soil, foliar and seed treatments in most agricultural crops all over the world (Moser and Obrycki, 2009;Uneme, 2011).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of thiamethoxam 70% WS as seed treatment against early sucking pests of tomato

Maurya

Singh

2015

JANS

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The present investigation was carried out at Vegetable Research Centre, G. B. Pant University of Agriculture and Technology, Pantnagar, Uttarakhand during the 2013 and 2014 to evaluate the effectiveness of thiamethoxam, used as seed treatment against the sucking insects of tomato. The seed treatment with thiamethoxam protected tomato seedlings from aphids and thrips at the early season from the onset of seed planting. There was a fast initial effect against the pests then gradually decreased to reach a moderate effect. Data revealed that Thiamethoxam 70% WS @ 4.2 g a.i./kg of seed showed the significant pest reduction followed by Thiamethoxam 70% WS @ 3.85 g a.i./kg of seed. Highest yield was recorded by Thiamethoxam 70% WS @ 4.2 g a.i./kg of seed (28.25 t/ha) closely followed by Thiamethoxam 70% WS @ 3.85 g a.i./kg of seed (25.00 t/ha) as compared to untreated check (20.91t/ha). Percent increase in yield over control was highest (35.10%) in Thiamethoxam 70% WS @ 4.2 g a.i./kg of seed followed by Thiamethoxam 70% WS @ 3.85 g a.i./kg of seed (19.56%). The percent reductions of predators by Thiamethoxam, used as seed treatment, in both the seasons ranged from 1.65-2.58% which was very minimum. Hence, it was concluded that the seed treatment of tomato with Thiamethoxam 70% WS @ 4.20 g a.i/kg of seed reduced the early season insect-pests (aphid and thrips) and had very less effect of natural enemies population as compared to control and also increased the fruit yield significantly than other treatments.

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“…cidal test with the American cockroach, the minimum lethal dose for each compound at 24 hr after injection was 64 nmol/insect, which was close to the values for imidacloprid (8) and the thiazolyl derivative (9), suggesting regeneration of the active ingredients in vivo. The decay of the oxodioxolylmethyl group is supposed to proceed as shown in Eqs.…”

Section: Figmentioning

confidence: 62%

“…We introduced an N-(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl group into the 3N-position of imidacloprid (8) and its chlorothiazolyl analog (9) (Fig. 3).…”

Section: Cyclic Carbonatesmentioning

confidence: 99%

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Proneonicotinoid

Kagabu

2011

J. Pestic. Sci.

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Since the discovery of imidacloprid in 1986, various structural modifications have been attempted to devise molecules with favorable biological properties different from those of the first product. [1][2][3][4][5][6][7][8][9][10] A prodrug is a substance that has to be transformed in order to show or enhance activity or to lessen unfavorable properties of the original ingredient. 11) Drabek and Neumann 12) introduced the term proinsecticide for an insecticide by referring to the pharmaceutical term. This article addresses nine prodrug types of the neonicotinoid, using the term proneonicotinoid in this context. Oxadiazine and Related Cyclic AzinesAcetal, thioacetal and aminal have been frequently used as a protective group for aldehyde or ketone in synthetic chemistry. 13) The assembled framework regenerates the carbonyl group by hydrolysis after the task, leaving the individual protecting fragments (Eq. 1, Fig. 1). Oxadiazine (XϭO), thiadiazine (XϭS) or triazine (XϭNMe) structure (1), constructed by linking both the amine ends of original insecticidal molecule (2) with formaldehyde through the corresponding hetero fragment, can be viewed as a similar assembly. 14-16) The cleavage of thiamethoxam (3) into clothianidin (5) in insects and plant tissues has been reported. 17,18) Hydrolysis comparison of the three cyclic azines (1) to the corresponding diaminonitroimines (2) in a physiological salt solution showed that the half-lives of the oxadiazines were notably longer than the corresponding thiadiazines and triazines. We have attributed the stability of the oxadiazine framework to the relatively strong -NCH 2 -O-CH 2 N-linkage by comparing the bond energy for C-O of 85-91 kcal/mol with 61 kcal/mol for C-S and 69-75 kcal/mol for C-N. 19) Thus, the devised thiamethoxam displays several favorable profiles in field practice, 16) and its present sales volume worldwide ranks second in the neonicotinoid class. This prodrug development practice clearly shows that a small structural variant (only one atom in this case) leads to large differences in the success. Mannich BasesThe Mannich reaction is the condensation of a labile C-H bond with an aldehyde and a primary or secondary amine to form a so-called Mannich base. 20) This well-established synthetic protocol was applied to a proneonicotinoid construction (Eqs. 2-4, Fig. 2). 21,22) The Mannich bases (7a, b) derived from b ,b -diamino nitroethylene molecules (6a, b) can regenerate the parent component in an acidic milieu. The concentrations of Mannich bases (7a, b) to cause spontaneous neuroblocking in the excised central nerve cord of American cockroaches (Periplaneta americana L.) were 100-140 mM at the level of 140 mM of 3N-Me (6c) derivative, and far higher than the 1.6-1.9 mM of the starting molecules (6a, b). However, 24 hr after the injection the minimum lethal doses were ProneonicotinoidShinzo KAGABU* Department of Chemistry, Faculty of Education, Gifu University, Gifu 501-1193, Japan (Received January 5, 2011 Accepted February 18, 2011) Prodrug is a biologi...

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Chemistry of Clothianidin and Related Compounds

Cited by 84 publications

References 9 publications

Application of Catalytic Hydrogen Evolution in the Presence of Neonicotinoid Insecticide Clothianidin

Application of Catalytic Hydrogen Evolution in the Presence of Neonicotinoid Insecticide Clothianidin

Evaluation of thiamethoxam 70% WS as seed treatment against early sucking pests of tomato

Proneonicotinoid

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