Dinotefuran

Dinotefuran is a systemic insecticide from the third-generation neonicotinoid class, widely used in agriculture for the control of sucking pests in various crops.

Common name: dinotefuran

Number CAS: 165252-70-0

Gross chemical formula: C7H14N4O3

Chemical class: Third-generation neonicotinoid (furanicotinyl), nitroguanidine subclass. It belongs to IRAC Group 4A (competitive modulators of nicotinic acetylcholine receptors). It differs from first- and second-generation neonicotinoids by the presence of a tetrahydrofuran ring instead of halogenated chloropyridine or chlorothiazole rings.

Main names of commercial products in Brazil: Dinno, Zeus and others. The product was registered in Brazil in August 2019.

Development history: Discovered and developed by Mitsui Chemicals, Inc. (Japan) in the 1990s (around 1993), based on rational molecular design using acetylcholine ester as the lead structure. The unique tetrahydrofuran ring structure was optimized for insecticidal activity and lower relative mammalian toxicity. Registered in Japan in April 2002. In the US, registered in 2004.

Mechanism of action: It acts as an agonist of nicotinic acetylcholine receptors (nAChR) in the central nervous system of insects. It causes continuous overstimulation of neurons, resulting in paralysis, cessation of feeding within a few hours, and death. It exhibits systemic action (translocation within the plant), contact and ingestion, with translaminar activity. Its furanic structure confers a slightly different binding mode from other neonicotinoids, which may contribute to its effectiveness against some resistant populations. It does not inhibit cholinesterase nor interfere with sodium channels (unlike organophosphates, carbamates, and pyrethroids).

Control spectrum: Broad spectrum, with activity against aphids, whiteflies, bed bugs, leafhoppers, mealybugs and thrips. Also controls some coleopterans (beetles) and others. Less effective against caterpillars compared to other groups.

Compatibilities and interactions: Generally compatible in tank mixes with many fungicides and insecticides from other groups. The synergist PBO (piperonyl butoxide) increases toxicity in resistant populations (indicating P450 involvement). Avoid mixing with strongly alkaline products. In IPM, the impact on natural enemies should be monitored (toxic to bees and some predators/parasitoids; use within safe application windows). High water solubility favors systemic action, but requires attention to drift and leaching.

Agronomic positioning: Fast-acting insecticide with systemic residual effect. In Brazil, it is positioned for use on rice, soybeans, corn, sugarcane, and vegetables. Rotation with other modes of action (e.g., Group 28 diamides, spinosyns) is recommended for resistance management. Low doses (generally 50–200 g ai/ha depending on the formulation and crop). Predominantly foliar application; potential for drench or seed treatment. Special attention should be paid to pollinators (avoid flowering) and aquatic organisms (due to solubility).

Other information:

Dinotefuran is a neonicotinoid insecticide developed by Mitsui Chemicals Agro. Dinotefuran features a tetrahydrofuran (THF) group, distinct from other neonicotinoids, with a chlorpyridine or chlorothiazole ring, considered an essential structural element for neonicotinoid action. The molecular design strategy based on the acetylcholine ester group as the main structure successfully led to the discovery of dinotefuran with the THF cyclic ether functional group. Its unique chemical properties, excellent biological properties, and favorable toxicological profile make dinotefuran available for pest management in a wide range of crops, with diverse application methods. DOI: 10.1021/jf1030778

Monitoring revealed a field population of whitefly (Bemisia tabaci) with high resistance to dinotefuran (255,6 times). The resistance is incompletely recessive, polygenic, and mediated primarily by P450 enzymes (especially CYP6DW5). The synergist PBO increased toxicity, and silencing the CYP6DW5 gene restored sensitivity. Evidence of cross-resistance with other neonicotinoids. DOI: 10.1002/ps.7251