New Unknown Modes of Action

Maienfisch, Peter; Dekeyser, Mark A.; Saito, Shigeru; Sakamoto, Noriko; Loiseleur, Olivier; Slaats, Brigitte

doi:10.1002/9783527644179.ch33

Cited by 9 publications

(5 citation statements)

References 70 publications

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“…The pyrimidine derivative 47 and its thiadiazole analogue 48 are both discovery milestones in the invention pathway to nematicide fluensulfone (Scheme 8). 89 A special case of successful isosteric ring exchange, in which a nitrogen atom and a carbon atom change their ring positions, is the 1,3-nitrogen shift (also called 1,3-carbon−nitrogen inversion) of cyclic hydrazine derivatives, such as pyrazoles, pyrazolines, and dihydropyridazines. An important value of this scaffold hopping tool, which was introduced in agrochemistry and primarily described by Stevenson and colleagues from DuPont/FMC, is that connectivities of substituents can be shifted from a ring carbon to a ring nitrogen and vice versa; for example, urea can be turned into amide, or C-linked phenyl can be turned into N-linked phenyl.…”

Section: Replacement Of a Heterocycle By Another Heterocyclic Ringmentioning

confidence: 99%

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Lamberth

2023

J. Agric. Food Chem.

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Replacing one ring in a molecule by a different carba- or heterocycle is an important scaffold hopping manipulation, because biologically active compounds and their analogues, which underwent such a transformation, are often similar in size, shape, and physicochemical properties and, therefore, likely in their potency as well. This review will demonstrate, how isosteric ring exchange led to the discovery of highly active agrochemicals and which ring interchanges have proven to be most successful.

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Section: Replacement Of a Heterocycle By Another Heterocyclic Ringmentioning

confidence: 99%

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Lamberth

2023

J. Agric. Food Chem.

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“…However, the exact mechanism of action on PPNs remains unknown. Some hypotheses suggest that fluensulfone possibly inhibits the enzyme acyl-CoA dehydrogenase, which is key in mobilizing lipids to obtain energy [129]; however, others suggest that its mechanism of action may be related to that of fluopyram [100,103]. In insects, the difluoroalkenyl derivatives were found to inhibit β-oxidation of fatty acids in the mitochondria [130].…”

Section: Fluensulfonementioning

confidence: 99%

“…in a wide variety of crops such as tomato, potato, pepper, cabbage, squash, and strawberry, among others [100,133]. Depending on the number of nematodes (population density per gram of soil), the type of crop rotation, and the presence of resistant plants, the average application rate is between 1.9 and 3.3 kg/ha [100,129]. There are different forms of application; however, the most recommended are drip injection or broadcast by mechanical incorporation with a single application 7 days before planting [129].…”

Section: Fluensulfonementioning

confidence: 99%

“…Depending on the number of nematodes (population density per gram of soil), the type of crop rotation, and the presence of resistant plants, the average application rate is between 1.9 and 3.3 kg/ha [100,129]. There are different forms of application; however, the most recommended are drip injection or broadcast by mechanical incorporation with a single application 7 days before planting [129]. It has been estimated that its half-life in soil is 36 days, with a dissipation rate (DT 50 ) of between 20 and 50 days, which can vary depending on the type of soil and environmental conditions [134,135].…”

Section: Fluensulfonementioning

confidence: 99%

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Plant-Parasitic Nematodes and Their Management: A Focus on New Nematicides

Rey Páez

2023

Nematodes - Ecology, Adaptation and Parasitism

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Plant parasitic nematodes are microscopic organisms that inhabit soil and plant tissues. Among such organisms, those of the genera Meloidogyne, Heterodera, Globodera, and Pratylenchus spp., are the most harmful, as they affect more than 2500 different species of plants, generating worldwide economic losses of over US$100 billion per year. These nematodes constitute a notable threat to the country’s progress and food security. Almost half of the global market for nematicides, which corresponds to US$ 1 billion per year, is used to control these nematodes. Non-fumigant nematicides are the most widely used in their control; however, many of them, such as carbamates and organophosphorus, are banned by environmental protection agencies because of their undesirable effects on non-target organisms. In the last 10 years, a new series of nematicides have emerged with different mechanisms of action than the old non-fumigant nematicides. Tioxazafen and fluazaindolizine are some of the latest new-generation nematicides that have come on the market. The rational design of new nematicides through in silico approaches combined with studies of the genetics and biochemistry of these microorganisms will help to better understand their management and control, aiming to reduce the environmental impact caused by the irrational use of nematicides.

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“…Pymetrozine, a representative of pyridine azomethine compounds, is a chemical insecticide that exerts a significant control effect on specific species of stinging and sucking pest ( Maienfisch et al, 2012 ; Li et al, 2021 ). Pymetrozine can be used to control aphids, leafhoppers, Bemisia tabacis , and rice planthoppers due to its high selectivity while showing safety to biological natural enemies of rice planthoppers, such as spiders and Anagrus nilaparvataes , during the control process ( Preetha et al, 2010 ; Lin et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Synergistic and Additive Interactions of Zhongshengmycin to the Chemical Insecticide Pymetrozine for Controlling Nilaparvata lugens (Hemiptera: Delphacidae)

Zhao

Li²,

Wang³

et al. 2022

Front. Physiol.

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Management of the rice brown planthopper Nilaparvata lugens Stål is challenging because it can rapidly adapt to new pesticides within several generations. Combined use of chemical insecticides and antimicrobials was proposed as an alternative strategy to control N. lugens. Our previous experiments identified two effective agents (chemical insecticide: pymetrozine and antimicrobial: zhongshengmycin) that act on different targets in N. lugens. However, conditions and effectiveness of combinations of antimicrobials and insecticides against N. lugens are still unknown. Here, we evaluated separate and combined effects of pymetrozine and zhongshengmycin on third instar nymphs of N. lugens under laboratory and greenhouse conditions. Results showed that zhongshengmycin exerts significant inhibitory effects on the three endosymbionts Pichia guilliermondii, Cryptococcus peneaus, and Pichia anomala cultured in vitro of N. lugens. Combinations of pymetrozine and zhongshengmycin under laboratory conditions produced additive or synergistic effects on N. lugens and caused higher mortality in third instar nymphs than either of them used alone. Experiments under greenhouse conditions further demonstrated that effective component quality ratio of pymetrozine to zhongshengmycin of 1:10 and 1:40 with co-toxicity coefficients of 221.63 and 672.87, respectively, also produced significant synergistic effects against N. lugens. Our results indicated that chemical insecticides combined with antimicrobials may provide a potential novel strategy for controlling N. lugens by inhibiting its endosymbionts.

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New Unknown Modes of Action

Cited by 9 publications

References 70 publications

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Plant-Parasitic Nematodes and Their Management: A Focus on New Nematicides

Synergistic and Additive Interactions of Zhongshengmycin to the Chemical Insecticide Pymetrozine for Controlling Nilaparvata lugens (Hemiptera: Delphacidae)

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