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

Wakita, Takeo; Kinoshita, K.; Kodaka, Kenji; Yasui, Naoko; Naoi, Atsuko; Banba, Sinichi

doi:10.1584/jpestics.29.356

Cited by 13 publications

(4 citation statements)

References 13 publications

(11 reference statements)

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“…DIN is unique in having a TFM moiety, which sets it apart from other aromatic CPM and CTM neonicotinoids. The TFM conformation for DIN overlays well with those for the CPM of IMI and the CTM of CLO, and the tetrahydrofuryl oxygen may function as the hydrogen acceptor, similar to the nitrogen of the pyridine or thiazole (33). Although not specifically considered here, the (S)-(+)-and (R)-(-)-enantiomers of DIN have different potencies, but (S)-(+)-and (RS)-(()-enantiomers show almost equal effectiveness in binding and toxicity evaluations (16,17).…”

Section: Discussionmentioning

confidence: 64%

Insect Nicotinic Acetylcholine Receptors: Neonicotinoid Binding Site Specificity Is Usually but Not Always Conserved with Varied Substituents and Species

Honda

Tomizawa

Casida

2006

J. Agric. Food Chem.

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The diversity of neonicotinoid insecticides acting as insect nicotinic acetylcholine (ACh) receptor (nAChR) agonists is illustrated by imidacloprid (IMI) with chloropyridinylmethyl (CPM) and N-nitroimine substituents, dinotefuran (DIN) with tetrahydrofurylmethyl (TFM) and N-nitroimine moieties, and acetamiprid (ACE) with CPM and N-cyanoimine groups. These three neonicotinoids are used here as radioligands to test the hypothesis that they all bind to the same site in the same way in both fruit flies (Drosophila melanogaster) and a leafhopper pest (Homalodisca coagulata): that is, neonicotinoid binding site specificity is conserved in the insect nAChRs. Multiple approaches show that [3H]IMI and [3H]ACE interact with an identical site in both species. However, although [3H]DIN binds with high affinity in both insects, its pharmacological profile in Homalodisca is surprisingly unique, with high sensitivity to some TFM-containing compounds and ACh. The TFM moiety of DIN may bind in a different orientation compared to the CPM group of IMI and ACE.

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Section: Discussionmentioning

confidence: 64%

Insect Nicotinic Acetylcholine Receptors: Neonicotinoid Binding Site Specificity Is Usually but Not Always Conserved with Varied Substituents and Species

Honda

Tomizawa

Casida

2006

J. Agric. Food Chem.

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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

1,353

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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“…Moreover, the THF moiety of 1 was substituted with methyl and ethyl groups ( 27 − 31 ) and was replaced by bicyclic ( 32 ) and tetrahydropyran ( 33 ) rings. The 4-methyl ( 27 ) and 5-methyl ( 28 ) THF analogues retained some potency of the unsubstituted 1 , whereas other analogues completely lost potency, except for 33 with some activity (Table ) . The SAR of the acyclic nitroguanidine moiety of 1 was also examined with nine compounds ( 34 − 42 ) (Table ).…”

Section: Structure−activity Relationshipsmentioning

confidence: 99%

Molecular Design of Dinotefuran with Unique Insecticidal Properties

Wakita

2010

J. Agric. Food Chem.

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Dinotefuran, (RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine, is a neonicotinoid insecticide developed by Mitsui Chemicals Agro. Dinotefuran provides a tetrahydrofuran (THF) moiety distinct from other neonicotinoids with a chloropyridine or chlorothiazole ring, which is considered to be an essential structural element for the neonicotinoid action. The molecular design strategy based on acetylcholine ester moiety as a lead structure has successfully led to the discovery of dinotefuran with the cyclic ether THF functional group. The unique chemical and excellent biological properties and favorable toxicological profile make dinotefuran available for pest management in wide range of crops with a variety of application methods.

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

Cited by 13 publications

References 13 publications

Insect Nicotinic Acetylcholine Receptors: Neonicotinoid Binding Site Specificity Is Usually but Not Always Conserved with Varied Substituents and Species

Insect Nicotinic Acetylcholine Receptors: Neonicotinoid Binding Site Specificity Is Usually but Not Always Conserved with Varied Substituents and Species

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

Molecular Design of Dinotefuran with Unique Insecticidal Properties

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