DINOTEFURAN

Details

Stereochemistry	RACEMIC
Molecular Formula	C7H14N4O3
Molecular Weight	202.2111
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(NCC1CCOC1)=N[N+]([O-])=O

InChI

InChIKey=YKBZOVFACRVRJN-UHFFFAOYSA-N

InChI=1S/C7H14N4O3/c1-8-7(10-11(12)13)9-4-6-2-3-14-5-6/h6H,2-5H2,1H3,(H2,8,9,10)

HIDE SMILES / InChI

Description
Sources: https://www.jstage.jst.go.jp/article/jpestics/30/2/30_2_122/_pdf
Curator's Comment: Description was created based on several sources, including https://www.mitsuichemicals.com/dinotefuran.htm

Dinotefuran is a new furanicotinyl insecticide which represents the third generation of neonicotinoid group. Dinotefuran, which was developed by Mitsui Chemicals, Inc., was registered in Japan April 24, 2002 and the registration has been submitted to the Environment Protection Agency (EPA) in the USA. Dinotefuran was granted Organophosphorus Alternative and Reduced Risk Status by the EPA. Dinotefuran exhibits a insecticidal activity against Hemiptera, Lepidoptera, Coleoptera, Diptera, Dictyoptera and Thysanoptera. Furthermore, it has very low phytotoxicity so that it can be utilized for many kinds of crops. Dinotefuran is water-soluble and has excellent systemic and translaminar action in many plants. This property enables dinotefuran to be applied using various methods and various formulations. The binding assay using insect nAChRs and the electrophysiological study showed that dinotefuran acted on nAChRs as an agonist. However, in the binding study, the affinity of dinotefuran against the binding site of other neonicotinoids was very low, suggesting that this compound acts on a different site than other neonicotinoids.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
H6BDY5 (H6BDY5_PERAM) 1 Target ID: H6BDY5 (H6BDY5_PERAM) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11852645 \| https://www.jstage.jst.go.jp/article/jpestics/30/2/30_2_122/_pdf	Agonist 2678		5.02 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Flea infestations 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22883971	Curative		Approved 8429	Vectra 3D Approved Use AVAILABLE FROM LICENSED VETERINARIANS ONLY - 6-way protection, repels and kills fleas, ticks, mosquitoes, lice, biting and sand flies, and mites (excluding mange mites) - Repels and kills Brown Dog ticks, American Dog ticks, Deer ticks, and Gulf Coast ticks and Lone Star ticks for one month - Begins reducing flea feeding in 5 minutes; starts to kill fleas within 2 hours - Kills all stages of the flea life cycle - Repels and kills ticks that may cause Lyme disease, Rocky Mountain spotted fever, babesiosis, ehrlichiosis, bartonellosis, hepatozoonosis and anaplasmosis - Kills biting flies that may transmit fly strike - Convenient topical treatment that allows application down to skin - Continues to kill and repel fleas and ticks after shampooing Vectra 3D spreads over the dog’s body to provide full body protection against fleas, ticks and mosquitoes.

PubMed

Title	Date	PubMed
Interaction of dinotefuran and its analogues with nicotinic acetylcholine receptors of cockroach nerve cords.	2002 Feb	11852645
Structural effects of dinotefuran and analogues in insecticidal and neural activities.	2002 Jul	12146167
Insecticidal activity and nicotinic acetylcholine receptor binding of dinotefuran and its analogues in the housefly, Musca domestica.	2003 Oct	14561066
The discovery of dinotefuran: a novel neonicotinoid.	2003 Sep	12974353
Assessment of cross-resistance potential to neonicotinoid insecticides in Bemisia tabaci (Hemiptera: Aleyrodidae).	2005 Dec	16336702
Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides.	2006 Jan	16411654
Automated flow fluorescent immunoassay for part per trillion detection of the neonicotinoid insecticide thiamethoxam.	2006 Jun 30	17723421
Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice.	2006 Nov	17112244
A nicotinic acetylcholine receptor mutation (Y151S) causes reduced agonist potency to a range of neonicotinoid insecticides.	2006 Nov	16981889
Effect of insecticides on mealybug destroyer (Coleoptera: Coccinellidae) and parasitoid Leptomastix dactylopii (Hymenoptera: Encyrtidae), natural enemies of citrus mealybug (Homoptera: Pseudococcidae).	2006 Oct	17066788
Current status of the greenhouse whitefly, Trialeurodes vaporariorum, susceptibility to neonicotinoid and conventional insecticides on strawberries in southern California.	2007 Aug	17591729
Toxicity of systemic neonicotinoid insecticides to avocado thrips in nursery avocado trees.	2007 Sep	17654635
Application timing and efficacy of alternatives for the insecticidal control of Tipula paludosa Meigen (Diptera: Tipulidae), a new invasive pest of turf in the northeastern United States.	2008 Oct	18416446
Neonicotinoid insecticides: historical evolution and resistance mechanisms.	2010	20737790

Patents

Sample Use Guides

In Vivo Use Guide

A novel spot-on formulation combining permethrin, pyriproxifen and dinotefuran (Vectra 3D™ spot-on solution for dogs) was evaluated in adult Beagle dogs in a study to determine adulticidal efficacy, egg laying inhibition and viability of Ctenocephalides felis felis eggs (development and emergence of fleas from the collected eggs). Prior to treatment sixteen dogs were checked for their ability to keep fleas 24 hours after infestation and were allocated to treatment groups: 8 dogs served as untreated controls, and 8 dogs were treated once with the tested formulation. The spot on was administered respecting the laboratory recommendations at a dosage of 65-126 mg/kg of permethrin; 8.9-17.4 mg/kg of dinotefuran and 0.8-1.5mg/kg of pyriproxyfen.

Route of Administration: Topical

In Vitro Use Guide

The present study demonstrated the effects of dinotefuran (active ingredient of the acaricide Protetor Pet®) on the ovary and midgut cells of semi engorged R. sanguineus females exposed to different concentrations of this chemical. For this, 120 semi-engorged females were divided into four treatment groups with 30 individuals each: group I or control (distilled water), group II (5000ppm), groups III (6250ppm) and group IV (8334ppm of dinotefuran).

Name

Type

Language

DINOTEFURAN

Common Name

English

DINOTEFURAN [EMA EPAR VETERINARY]

Common Name

English

DINOTEFURAN COMPONENT OF VECTRA 3D

Brand Name

English

VENOM

Brand Name

English

VECTRA 3D COMPONENT DINOTEFURAN

Brand Name

English

DINOTEFURAN [MI]

Common Name

English

MIKEBLOCK

Brand Name

English

VECTRA FELIS COMPONENT DINOTEFURAN

Brand Name

English

ALBARIN

Brand Name

English

STARKLE

Brand Name

English

2-METHYL-1-NITRO-3-(TETRAHYDROFURAN-3-YLMETHYL)GUANIDINE

Systematic Name

English

N''-METHYL-N-NITRO-N'-((TETRAHYDRO-3-FURANYL)METHYL)GUANIDINE

Systematic Name

English

SAFARI

Brand Name

English

GUANIDINE, N''-METHYL-N-NITRO-N'-((TETRAHYDRO-3-FURANYL)METHYL)-

Systematic Name

English

(RS)-1-METHYL-2-NITRO-3-(TETRAHYDRO-3-FURYLMETHYL) GUANIDINE

Systematic Name

English

TENCHU

Brand Name

English

MTI-446

Common Name

English

1-METHYL-2-NITRO-3-((3-TETRAHYDROFURYL)METHYL)GUANIDINE

Systematic Name

English

DINOTEFURAN [ISO]

Common Name

English

DINOTEFURAN [JAN]

Common Name

English

DINOTEFURAN COMPONENT OF VECTRA FELIS

Brand Name

English

Classification Tree Code System Code

EMA VETERINARY ASSESSMENT REPORTS

VECTRA 3D [AUTHORIZED]