Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part

Wakita, Takeo; Kinoshita, K.; Yasui, Naoko; Yamada, Eiichi; Kawahara, Nobuyuki; Kodaka, Kenji

doi:10.1584/jpestics.29.348

Cited by 21 publications

(7 citation statements)

References 7 publications

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“…The insecticidal activity of dinotefuran and its derivatives is better correlated to nerve-blocking activity than to nerve-excitatory activity, a characteristic also observed with other neonicotinoids (Kagabu et al 2008 ). Both the nitroguanidine and the terahydro-3-furylmethyl parts of the molecule are important for the insecticidal activity of dinotefuran (Wakita et al 2004a ; Wakita et al 2004b ; Wakita 2010 ). However, compared to imidacloprid and acetamiprid, dinotefuran appears more effective in inducing depolarizing currents in terms of current amplitude and concentration dependence (Le Questel et al 2011 ).…”

Section: Mode Of Action On Invertebratesmentioning

confidence: 99%

Systemic insecticides (neonicotinoids and fipronil): trends, uses, mode of action and metabolites

Simon‐Delso

Amaral-Rogers

Belzunces

et al. 2014

Environ Sci Pollut Res

1,404

881

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Since their discovery in the late 1980s, neonicotinoid pesticides have become the most widely used class of insecticides worldwide, with large-scale applications ranging from plant protection (crops, vegetables, fruits), veterinary products, and biocides to invertebrate pest control in fish farming. In this review, we address the phenyl-pyrazole fipronil together with neonicotinoids because of similarities in their toxicity, physicochemical profiles, and presence in the environment. Neonicotinoids and fipronil currently account for approximately one third of the world insecticide market; the annual world production of the archetype neonicotinoid, imidacloprid, was estimated to be ca. 20,000 tonnes active substance in 2010. There were several reasons for the initial success of neonicotinoids and fipronil: (1) there was no known pesticide resistance in target pests, mainly because of their recent development, (2) their physicochemical properties included many advantages over previous generations of insecticides (i.e., organophosphates, carbamates, pyrethroids, etc.), and (3) they shared an assumed reduced operator and consumer risk. Due to their systemic nature, they are taken up by the roots or leaves and translocated to all parts of the plant, which, in turn, makes them effectively toxic to herbivorous insects. The toxicity persists for a variable period of time—depending on the plant, its growth stage, and the amount of pesticide applied. A wide variety of applications are available, including the most common prophylactic non-Good Agricultural Practices (GAP) application by seed coating. As a result of their extensive use and physicochemical properties, these substances can be found in all environmental compartments including soil, water, and air. Neonicotinoids and fipronil operate by disrupting neural transmission in the central nervous system of invertebrates. Neonicotinoids mimic the action of neurotransmitters, while fipronil inhibits neuronal receptors. In doing so, they continuously stimulate neurons leading ultimately to death of target invertebrates. Like virtually all insecticides, they can also have lethal and sublethal impacts on non-target organisms, including insect predators and vertebrates. Furthermore, a range of synergistic effects with other stressors have been documented. Here, we review extensively their metabolic pathways, showing how they form both compound-specific and common metabolites which can themselves be toxic. These may result in prolonged toxicity. Considering their wide commercial expansion, mode of action, the systemic properties in plants, persistence and environmental fate, coupled with limited information about the toxicity profiles of these compounds and their metabolites, neonicotinoids and fipronil may entail significant risks to the environment. A global evaluation of the potential collateral effects of their use is therefore timely. The present paper and subsequent chapters in this review of the global literature explore these risks and show a growing body of evidence t...

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Section: Mode Of Action On Invertebratesmentioning

confidence: 99%

Systemic insecticides (neonicotinoids and fipronil): trends, uses, mode of action and metabolites

Simon‐Delso

Amaral-Rogers

Belzunces

et al. 2014

Environ Sci Pollut Res

1,404

881

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“…The 2-methyl derivative (xiii) was prepared by the reduction of oxime, which was synthesized from xii 8) and a 2-methoxy derivative (xv) was prepared by the reduction of amide which was synthesized from xiv. 9) Acyclic and cyclic (tetrahydro-3-furyl)methyl compounds (xvi and xvii) were synthesized according to published procedures, 3) using amines (v, viii, xi, xiii and xv) and mesylates (iv, vii and x). Typical procedures are described as follows.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Tetrahydro-3-furylmethyl Part

et al. 2004

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The (Ϯ)-tetrahydro-3-furylmethyl moiety, which is a characteristic part of the novel neonicotinoid dinotefuran, was found by research in which acetylcholine was selected as the lead compound. SAR (structure-activity relationships) for the tetrahydrofuran part indicated that the non-substituted moiety showed the highest level of activity, 4-and 5-substituted moieties showed intermediate levels, and 2-and 3-substituted moieties lost the activity. Conformational analysis of these compounds indicated that the substituents changed little the hypothetical active conformation of dinotefuran. Computational analysis proved that dinotefuran, a methoxypropyl compound and other neonicotinoids well overlapped, and dinotefuran adopts the active conformation more easily than the methoxypropyl compound.

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“…It is also commercialized in the racemic form. To our best knowledge, many works of dinotefuran up to now have been mostly focused on chemical synthesis [10,12,13], achiral analysis and the residue determinations of its racemate by ELISA [14] or by HPLC [15] or HPLC/MS/MS [16][17][18]. There are also some reports about its toxicity to target and non-target pests [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective separation and determination of the dinotefuran enantiomers in rice, tomato and apple by HPLC

Chen

Dong

Liu

et al. 2012

J of Separation Science

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An effective chiral analytical method was developed for the resolution and determination of dinotefuran enantiomers in rice, tomato and apple samples. Dinotefuran enantiomers were baseline-separated and determined on a novel chiral column, ChromegaChiral CCA, with n-hexane-ethanol-methanol (85:5:10, v/v/v) as the mobile phase at a flow rate of 1.0 mL/min with UV detection at 270 nm. The resolution of dinotefuran enantiomers was about 1.8. The first eluted enantiomer was (+)-dinotefuran and the second eluted one was (-)-dinotefuran. The effects of mobile-phase composition and column temperature on the enantioseparation were evaluated. The method was validated for linearity, repeatability, accuracy, LOD and LOQ. LOD was 0.15 mg/kg in rice and tomato, 0.05 mg/kg in apple, with an LOQ of 0.5 mg/kg in rice and tomato, 0.2 mg/kg in apple. The average recoveries of the pesticide from all matrices ranged from 75.8 to 92.9% for all fortification levels The precision values associated with the analytical method, expressed as RSD values, were <16.5% for the pesticide in all matrices. The methodology was successfully applied for the enantioselective analysis of dinotefuran enantiomers in real samples, indicating its efficiency in investigating the environmental stereochemistry of dinotefuran in food matrix.

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Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part

Cited by 21 publications

References 7 publications

Systemic insecticides (neonicotinoids and fipronil): trends, uses, mode of action and metabolites

Systemic insecticides (neonicotinoids and fipronil): trends, uses, mode of action and metabolites

Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Tetrahydro-3-furylmethyl Part

Enantioselective separation and determination of the dinotefuran enantiomers in rice, tomato and apple by HPLC

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