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Discovery of a novel acaricide, acynonapyr.

ABSTRACT: Acynonapyr, discovered by Nippon Soda Co., Ltd., is a novel acaricide with N-pyridyloxy azabicycle as a unique core structure. Acynonapyr exhibits high activity against the spider mite species in the genera Tetranychus and Panonychus, with good efficacy at all life stages. Early in this research, cyclic amines substituted with (hetero)aryl(oxy) moieties were designed as target molecules and diversely synthesized, and 4-[4-(trifluoromethyl)phenoxy]-1-[5-(trifluoromethyl)-2-pyridyl]piperidine was found to show weak acaricidal activity. The structural optimization of this acaricidal active piperidine as the first lead compound led to the discovery of acynonapyr. In this report, our research process that led to the discovery of acynonapyr is described.

SUBMITTER: Hamamoto I

PROVIDER: S-EPMC10710939 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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Discovery of a novel acaricide, acynonapyr.

Hamamoto Isami I Kawaguchi Masahiro M Nakamura Takehiko T Yano Makio M Koizumi Keiji K Takahashi Jun J

Journal of pesticide science 20231101 4

Acynonapyr, discovered by Nippon Soda Co., Ltd., is a novel acaricide with N-pyridyloxy azabicycle as a unique core structure. Acynonapyr exhibits high activity against the spider mite species in the genera Tetranychus and Panonychus, with good efficacy at all life stages. Early in this research, cyclic amines substituted with (hetero)aryl(oxy) moieties were designed as target molecules and diversely synthesized, and 4-[4-(trifluoromethyl)phenoxy]-1-[5-(trifluoromethyl)-2-py ...[more]

PMID: 38090213

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Project description:BackgroundChemical analysis shows that honey bees (Apis mellifera) and hive products contain many pesticides derived from various sources. The most abundant pesticides are acaricides applied by beekeepers to control Varroa destructor. Beekeepers also apply antimicrobial drugs to control bacterial and microsporidial diseases. Fungicides may enter the hive when applied to nearby flowering crops. Acaricides, antimicrobial drugs and fungicides are not highly toxic to bees alone, but in combination there is potential for heightened toxicity due to interactive effects.Methodology/principal findingsLaboratory bioassays based on mortality rates in adult worker bees demonstrated interactive effects among acaricides, as well as between acaricides and antimicrobial drugs and between acaricides and fungicides. Toxicity of the acaricide tau-fluvalinate increased in combination with other acaricides and most other compounds tested (15 of 17) while amitraz toxicity was mostly unchanged (1 of 15). The sterol biosynthesis inhibiting (SBI) fungicide prochloraz elevated the toxicity of the acaricides tau-fluvalinate, coumaphos and fenpyroximate, likely through inhibition of detoxicative cytochrome P450 monooxygenase activity. Four other SBI fungicides increased the toxicity of tau-fluvalinate in a dose-dependent manner, although possible evidence of P450 induction was observed at the lowest fungicide doses. Non-transitive interactions between some acaricides were observed. Sublethal amitraz pre-treatment increased the toxicity of the three P450-detoxified acaricides, but amitraz toxicity was not changed by sublethal treatment with the same three acaricides. A two-fold change in the toxicity of tau-fluvalinate was observed between years, suggesting a possible change in the genetic composition of the bees tested.Conclusions/significanceInteractions with acaricides in honey bees are similar to drug interactions in other animals in that P450-mediated detoxication appears to play an important role. Evidence of non-transivity, year-to-year variation and induction of detoxication enzymes indicates that pesticide interactions in bees may be as complex as drug interactions in mammals.

Project description:Globally, the prevalence of Rhipicephalus microplus resistance to various acaricides has increased, and there is a need for the identification of molecular markers that can predict phenotypic resistance. These markers could serve as alternatives to the larval packet test (LPT), enabling rapid and accurate monitoring of resistance in these ticks against multiple acaricides. However, many of the historically identified markers are present in isolates from specific countries and their role in acaricide resistance remains unclear. This study aimed to assess these mutations by sequencing genomic regions encoding proteins historically associated with acaricide target site insensitivity and increased acaricide detoxification and comparing resistant and susceptible isolates from eight different countries. Employing a novel multiplex PCR setup developed during the study, the coding regions of 11 acaricide-resistant targets were amplified and sequenced across 37 R. microplus isolates from different locations. The identified mutations, both previously reported and novel, were compared between acaricide-susceptible and acaricide-resistant isolates, phenotypically characterized using the larval packet test or larval immersion test across five acaricide classes. Genotypes were then correlated with available phenotypes, and protein modelling of novel nonsynonymous mutations was conducted to assess their potential impact on acaricide resistance. Previously reported resistance-associated mutations were detected, some of which were present in both resistant and susceptible isolates. Novel mutations emerged from the 11 targets, but distinctions between susceptible and resistant isolates were not evident, except for the prevalent kdr mutation in synthetic pyrethroid-resistant isolates. The quest for predictive molecular markers for monitoring acaricide resistance remains challenging. Nevertheless, by utilizing a representative group of isolates, we determined that several historical mutations were present in both resistant and susceptible isolates. Additionally, the study provides valuable genetic data on acaricide-resistant and susceptible isolates from different geographical regions, focusing on genomic regions implicated in resistance. This baseline data offers a critical foundation for further research and the identification of more reliable molecular markers.

Project description:ObjectiveTetranychus cinnabarinus (Boisduval) is an agricultural mite pest threatens crops throughout the world, causing serious economic loses. Exploring the effects of acaricides on predatory mites is crucial for the combination of biological and chemical control of T. cinnabarinus. Neoseiulus californicus (McGregor) is one of the principal natural enemies of T. cinnabarinus, which can be applied in protected agriculture. In this study, the effects of sublethal concentrations of a new acaricide, SYP-9625 on two mite species, and the effects of the application concentration on predatory mite, N. californicus were assessed. The aim of the present study was to evaluate the effect of SYP-9625 on life parameters and predation capacity of N. californicus based on the concentration-response bioassay of T. cinnabarinus to explor the application of the new acaricide with natural enemy N. californicus.MethodAll of the experiments were conducted under laboratory conditions [25 ± 1°C, 16: 8 h (L: D) and 75 ± 5% RH]. The sublethal concentrations LC10 (0.375μg/mL) and the LC30 (0.841μg/mL) against T. cinnabarinus and the application concentration (100μg/mL) against N. californicus were used to evaluate the effects of SYP-9625 on population parameters of N. californicus based on an age-stage, two-sex life table and its predation capacity by functional response.Resultcinnabarinus females treated with LC30 exhibited significantly reduced net reproductive rates (R0 = 11.02) in their offspring compared with females treated with LC10 (R0 = 14.96) and untreated females (R0 = 32.74). However, the intrinsic rate of increase (rm) and the finite rate of increase (λ) of N. californicus indicated that the application concentration of SYP-9625 had no significant negative effect on N. californicus eggs (rm = 0.277, λ = 1.319) compared to the control (rm = 0.292, λ = 1.338). Additionally, most population parameters of N. californicus showed a dose-dependent manner with the increase of the concentration of SYP-9625 against T. cinnabarinus. SYP-9625 also stimulated the control efficiency of N. californicus against immobile stages including eggs and larvae.ConclusionThis study demonstrated that sublethal concentrations of SYP-9625 can inhibit the population growth of T. cinnabarinus. In addition, the sublethal concentrations and the application concentration showed no effect on the population growth of N. californicus. These two advantages described above showed great commercial potential of this new acaricide based on population parameters of the two mite species and predation capacity of the predatory mite under laboratory conditions.

Dataset Information

Discovery of a novel acaricide, acynonapyr.

Publications

Discovery of a novel acaricide, acynonapyr.

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