New chlorinated juvenile hormone analogues and their biological activity

Piccardi, P.; Bettarini, Franco; Longoni, Angelo

doi:10.1002/ps.2780110409

Cited by 13 publications

(4 citation statements)

References 22 publications

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“…In our research to find new insecticides, we focused on two known insecticidal compounds 1 and 2 (Fig 1) which have a 3,3‐dichloro‐2‐propenyloxy group in common 1, 2. This group attracted much of our attention as an interesting group to generate a new lead compound.…”

Section: Introductionmentioning

confidence: 99%

The discovery of pyridalyl: a novel insecticidal agent for controlling lepidopterous pests

Sakamoto

Saito

Hirose

et al. 2003

Pest Management Science

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Synthesis of analogues of two compounds with known insecticidal activity, both of which contain a 3,3-dichloro-2-propenyloxy group, produced 2-(trifluoromethyl)-4-phenoxyphenyl 3,3-dichloro-2-propenyl ether, which had weak activity against lepidopterous larvae. Structural modifications around this lead compound led to the development of pyridalyl [Pleo, S-1812; 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-[5-(trifluoromethyl)-2-pyridyloxy]propyl ether], which belongs to a new class of insecticides. Pyridalyl gives very good control of various lepidopterous and thysanopterous pests on cotton and vegetables, without phytotoxicity. It controls populations of Heliothis virescens F and Plutella xylostella (L) which are resistant to various currently used insecticides. It also produces unique insecticidal symptoms, so it may have a different mode of action from other existing insecticides. Pyridalyl is also less harmful than existing insecticides to various beneficial arthropods, so it should provide an important tool in IPM and insecticidal management programmes for the control of lepidopterous and thysanopterous pests. The first market introduction is expected in Japan and some Asian countries in the years between 2004 and 2005.

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Section: Introductionmentioning

confidence: 99%

The discovery of pyridalyl: a novel insecticidal agent for controlling lepidopterous pests

Sakamoto

Saito

Hirose

et al. 2003

Pest Management Science

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“…The synthesis scheme shown in Figure 3 provides moderate yields of the test compounds. The structures of all synthesized compounds were analyzed and confirmed by 1 H NMR and MS. Due to the structural similarity of compounds 8, only some representative compounds, such as 8a′-1, 8a-2, 8a′-2, 8b-2, 8e, and 8e′, were analyzed and confirmed by 13 C NMR and 8a-2, 8a′-2 and 8e by elemental analysis. Table 1 summarizes the chemical structures, MS data, and physical characteristics of compounds 8.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Dihalopropene ethers are active against a wide range of pests. − However, only one member of this group, 2,6-dichloro-4-(3,3-dichloroallyoxy)phenyl 3-[5-(trifluoromethyl)-2-pyridyloxy]propyl ether (S-1812), − has been developed as an agricultural insecticide under the trade name “Pyridalyl” by Sumitomo Chemical Co Ltd., Japan (Figure ). Although the mechanism of Pyridalyl is yet unknown or undetermined, it exhibits diverse characteristics, such as long residual activity, excellent rain fastness, no cross-resistance to other insecticide classes, and great safety to nontarget beneficial organisms especially honey bees and bumble bees.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers

Liu

et al. 2015

J. Agric. Food Chem.

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Dihalopropene ether insecticides are known for good features such as no cross-resistance to other insecticide classes and safety for mammals. Pyridalyl is the only currently commercialized dichloropropene ether insecticide; however, it contains a trifluoromethyl group, the synthesis of which requires harsh reagents and reaction conditions. To search for novel dihalopropene ethers with unique biological activities but without trifluoromethyl groups, a series of nitropyridyl-based dichloropropene ether analogues were synthesized by reacting nitro-based halopyridine with 2,6-dichloro-4-(3,3-dichloroallyloxy)phenol or 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-hydroxypropyl ether. Bioassay showed that the compounds exhibited potent insecticidal activities against various lepidopteran pests. Particularly, 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-(5-nitro-2-pyridyloxy)propyl ether (8e) was active against major agricultural pests, and its insecticidal potency was comparable to that of Pyridalyl. Besides the trifluoromethyl group in Pyridalyl, a nitro group on the 5-position of the pyridyl ring is also viable for the development of optimal insecticidal activity.

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“…102 SAR studies evaluating numerous substitution patterns around the phenyl rings coupled with screening against a range of mite and insect species ultimately led to the identification of etoxazole as a highly effective acaricide. 102 Likewise, scientists at Sumitomo noted that two different insecticidal compounds, one a potential antijuvenile hormone from Zoecon 150 and the other a juvenile hormone mimic, 151 both had a 3,3-dichloro-2-propenyloxy group as a common feature (Fig. 7).…”

Section: Bioactive Scaffoldmentioning

confidence: 99%

Innovation in insecticide discovery: Approaches to the discovery of new classes of insecticides

Sparks¹,

Bryant

2022

Pest Management Science

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The continuing demand for agrochemical insecticides that can meet increasing grower, environmental, consumer and regulatory requirements creates the need for the development of new solutions for managing crop pest insects. The development of resistance to the currently available insecticidal products adds another critical driver for new insecticidal active ingredients (AIs). One avenue to meeting these challenges is the creation of new classes of insecticidal molecules to act as starting points and prototypes stimulating further spectrum, efficacy and environmental impact refinements. A new class of insecticides is foreshadowed by the first molecule exemplifying that class (first‐in‐class, FIC) and offers one measure of innovation within the agrochemical industry. Most insecticides owe their discovery to competitor‐inspired (i.e. competitor patents/products) or next‐generation (follow‐on to a company's pre‐existing product) strategies. In contrast, FIC insecticides primarily emerge from a bioactive hypothesis approach, with the largest segment resulting from the exploration of new areas of chemistry/heterocycles and underexploited motifs. Natural products also play an important role in the discovery of FIC insecticides. Understanding the origins of these FIC compounds and the approaches used in their discovery can provide insights into successful strategies for future FIC insecticides. This review analyses information on historic and recently introduced FIC insecticides. Its main objective has been to identify the most successful discovery strategies for identifying new agrochemical solutions to meet the challenge of minimizing crop losses resulting from insects. © 2022 Society of Chemical Industry.

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New chlorinated juvenile hormone analogues and their biological activity

Cited by 13 publications

References 22 publications

The discovery of pyridalyl: a novel insecticidal agent for controlling lepidopterous pests

The discovery of pyridalyl: a novel insecticidal agent for controlling lepidopterous pests

Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers

Innovation in insecticide discovery: Approaches to the discovery of new classes of insecticides

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