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Organophosphorus compounds (OPs) are a large and diverse class of chemicals that have been synthesized, since the XIX century for several purposes like chemical weapons, flame-retardants, ectoparasiticides and investigational new drugs, but mainly as agrochemicals in agriculture and indoor. Although the amount of OP pesticides being used is declini...
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... as chemical weapons can be divided into two general types: the G and V agents. The most known G agents: sarin (GB), soman (GD) and tabun (GA), were developed in Germany shortly before or during WWII and possess two oxygen atoms bonded to phosphorus (Table 1). The most known V type agent, VX, is an alkylphosphonothiolate developed in 1952, by the British chemist Ranajit Ghosh, and contains sulfur, as well as two oxygens, bonded to phosphorus. ...
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... OPs are esters of phosphoric acid and its derivatives with varying combinations of oxygen, carbon and sulfur or with nitrogen attached. The general chemical structure of an OP (Table 1) comprises a central phosphorus atom with a double bound to oxygen or sulfur, where R 1 and R 2 are commonly alkyl or aryl groups bound to the phosphorus atom either through an oxygen or sulfur (phosphrothioates) or directly (phosphonates or phosphinates). Symbol X represents a variety of groups and is called the leaving group, which is replaced (usually by nucleophilic substitution) by the oxygen of the serine residue at the target protein active site. ...
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... X represents a variety of groups and is called the leaving group, which is replaced (usually by nucleophilic substitution) by the oxygen of the serine residue at the target protein active site. There are at least 13 types of OPs (summarized in Table 1). 37 Table 1 (line 1) shows the basic structure of a typical OP, where R 1 and R 2 are equaling methyl, ethyl or isopropyl. ...
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... 1958 three dozen compounds were cited to be commercial from that the phosphate and phosphinate esters can give rise to 1,250 potential compounds, while, for making the thionate analogues, the number is doubled. [40][41][42] Thus, OPs vary extremely in chemical structure and also in chemical properties (Table 1). OPs can be miscible with water, but more typically are miscible with organic solvents; Table 1 also shows the octanol-water partitioning coefficients of some OPs. ...
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... Thus, OPs vary extremely in chemical structure and also in chemical properties (Table 1). OPs can be miscible with water, but more typically are miscible with organic solvents; Table 1 also shows the octanol-water partitioning coefficients of some OPs. [43][44][45] ...
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... main current focus in the development of oximes is to improve the blood-brain-barrier penetration for a more efficacious reactivation of inhibited brain AChE. 61 Table 1. Types of the most common organophosphorus compounds (OPs) used as pesticides and chemical weapons (cont.) Figure 1. ...
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Phosphorus monoxide (PO • ) was the first compound with a P–O bond to be spectroscopically detected in interstellar space. On Earth, PO • , and related functionalized molecules such as R–P = O (R = OH, CH 3 , OCH 3 , Ph), have been studied in inert gas matrices at ultralow temperatures (3–15 K). These species are believed to be key intermediates in...
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... Los compuestos organofosforados (OP) representan una gran cantidad de productos químicos que se han sintetizado desde el siglo XIX para diversos fines, como ectoparasiticidas, agente de guerra químicas, productos farmacéuticos, aditivos del petróleo, solventes y aislantes eléctricos, sin embargo, se sintetiza principalmente como un plaguicida controlado por vectores de la higiene sanitaria (Mangas, Vilanovab, Estévezc, & França, 2016). ...
Los plaguicidas organofosforados son agentes de control de plagas y enfermedades utilizados en todo el mundo para mejorar los procesos agrícolas. La acetilcolinesterasa eritrocitaria es el biomarcador de elección para el seguimiento biológico de la población en edad laboral expuesta a plaguicidas organofosforados porque la combinación de productos químicos agrícolas con una enzima en las terminaciones nerviosas del cerebro y el sistema nervioso impide la transmisión de los impulsos nerviosos, provocando intoxicaciones. El objetivo de este estudio es determinar los efectos neurotóxicos asociados a la exposición crónica a plaguicidas y fertilizantes en una muestra de 103 trabajadores mediante un cuestionario neuropsicológico y análisis de personal. Este estudio mostró una disminución significativa en la acetilcolinesterasa de los eritrocitos, lo que indica signos y síntomas de exposición excesiva a pesticidas y probable envenenamiento crónico en trabajadores bananeros. En conclusión, la mayoría de los trabajadores exhibieron signos y síntomas indicativos de exposición excesiva a pesticidas y probable envenenamiento crónico.
... 7 O fósforo elementar é essencial na constituição dos componentes vitais da célula, a exemplo das membranas celulares fosfolipídicas, da ferramenta de transferência energética intracelular que é a ATP, e do DNA e RNA pela ligação de fosfodiéster entre nucleotídeos. 5,6,11,12 Além disso, a deficiência de P desencadeia o surgimento de uma coloração azul-verde nas folhas, além de fraqueza e retardamento de crescimento na flora. No caso da fauna, ocorre diminuição da taxa de desenvolvimento e, pelo fato do fosfato de cálcio compor ossos e dentes, esses seres vivos sofrem com estrutura óssea quebradiça na carência de fósforo. ...
SUSTAINABILITY IN PHOSPHORUS USE: A BIBLIOGRAPHIC REVIEW FOCUSING ON THE CURRENT SITUATION IN THE STATE OF SÃO PAULO, BRAZIL. Phosphorus is a non-renewable element essential for the existence of life and also for food security. This resource has the property of limiting plant growth, becoming a fundamental part of agricultural production. On the other hand, when this element is present in high concentrations in aquatic environments, it can start a phenomenon called eutrophication, which causes a series of changes in biological succession processes and strongly negative impacts on species’ biodiversity and wealth. In this context, this work aimed, from an extensive bibliographical review, to gather strategic and essential information related to phosphorus sustainability, provoking a reflection regarding scenarios that involve this indispensable nutrient, focusing on the current situation of the State of São Paulo, Brazil, an important case study, both for the Brazilian and international scenario, by a gathering of data on the current situation of two of the main watersheds in the corresponding region. Relevant technologies used for phosphorus removal in eutrophicated environments are also addressed. Finally, the possibility of reusing the nutrients present in eutrophicated water bodies as an alternative source of phosphate fertilizer for agriculture is demonstrated.
... Organophosphorus (OP) compounds tend to be associated with synthetic products arising from agrochemical, chemical, or pharmaceutical industries (Mangas et al., 2016). However, it should be remembered that OP compounds have also evolved naturally as essential components of life (e.g., DNA, RNA, phospholipids, metabolic intermediates, signaling molecules, and regulators of protein function) (Berg et al., 2019;Walsh, 2021). ...
Organophosphorus (OP) compounds include trivalent and pentavalent phosphorus; this article covers only the more
common pentavalent phosphorus compounds. These chemicals are often thought of as insecticides or nerve agents whose acute toxicity arises from inhibition of acetylcholinesterase (AChE), but OP compounds are also widely used as flame retardants, fuel additives, lubricants, plasticizers, and pharmaceuticals. In addition to their acute effects, some anti-AChE OP compounds have been associated with the intermediate syndrome. Finally, OP compounds that inhibit and age neuropathy target esterase produce OP compound-induced delayed neurotoxicity, a distal degeneration of sensory and motor axons in peripheral nerves and spinal cord.
... The distal degeneration of some PNS and CNS axons is a characteristic of OP-induced delayed neuropathy (OPIDN), which occurs after a single or short-term exposure (Lotti and Moretto 2005). OPIDN is a neurodegenerative condition that affects nerves with long fiber tracts in both the PNS and CNS (Mangas et al. 2016). A systematic review found that there was permanent damage after acute exposure, which resulted in deficits in cognitive and psychomotor performance, as well as dysfunction in the motor and sensory nerves (Karami-Mohajeri et al. 2014). ...
... OP pesticides can damage all the regions of the brain, but the most significantly affected area is the hippocampus, the part of the brain responsible for controlling memory and learning (Farkhondeh et al. 2020). Review studies on the neurotoxic effects of organophosphorus compounds have shown that farmers who were exposed to OP pesticides in the short term also had longterm effects (Karami-Mohajeri et al. 2014;Mangas et al. 2016). They stated that the permanent damage includes deficits in cognitive and psychomotor performance. ...
Farmers are regarded as a high-risk population for pesticide exposure because of the frequency of their occupational exposure to organophosphate (OP) pesticides. The purposes of this study were 1) to compare urinary OP metabolites, nerve conduction, and neurobehavioral (NB) performance between farmers and a control group, as well as between baseline measurement and after spraying OP pesticides; 2) to investigate the factors associated with increased urinary OP metabolites after spraying OP pesticides; and 3) to investigate the effects of OP metabolites on changes in nerve conduction and NB performance after spraying OP pesticides. This study was conducted with a sample size of 71 farmers and a control group of 26. The findings showed that after spraying OP pesticides total dialkylphosphate (DAP) levels were significantly higher than baseline levels. Multiple linear regression showed that increased urinary OP metabolites among farmers after spraying pesticides were negatively associated with wearing a mask when spraying OP pesticides and positively associated with the number of years of farm work and type of sprayer equipment. The results also showed a positive association between the increased urinary total diethylphosphate (DEP) levels and the decreased amplitude of motor nerve conduction. Furthermore, a positive correlation was observed between increased urinary total DEP and decreased right amplitude of sympathetic skin response (SSR). An increase in urinary total DMP was positively associated with a decrease in raw score and a standard score of visual-motor integration (VMI). Our findings provide evidence that exposure to OP pesticides can cause a deficit in nerve conduction and NB performance in farmers. These findings may contribute to the early detection of neurological disease and inform strategies to prevent damage to the peripheral and central nervous systems.
... These agents lead to more potent inhibition of NTE than acetylcholinesterase (AchE) with subsequent aging of NTE. 11 Inhibition of NTE results from phosphorylation and aging occurs when the lateral side chain leaves the phosphorylated NTE. 12 Seventy to ninety percent of NTE should be inhibited for the neuropathic effects to appear. Chlorpyrifos poisoning, as in our case, produces an active metabolite that has a ratio of anti-AchE to anti-NTE equal to 0.07 and is known to cause OPIDN. ...
Organophosphate-induced delayed neuropathy, a central-distal axonopathy, passes through latent, progressive, static and improvement phases. During the improvement phase, the peripheral nerves regenerate unmasking the spinal cord lesion with myelopathic features. We report a case of a 16-year-old male who developed myelopathy 6 weeks following chlorpyrifos poisoning. He had a motor weakness of 4/5 in bilateral hips and 3/5 in bilateral knees and ankles. Spasticity and exaggerated reflexes with ankle clonus were present in the lower limbs. Sensory and the upper limb motor examinations were all normal. Pertinent blood, cerebrospinal fluid and nerve conduction tests were normal. Magnetic resonance imaging of the spine showed features of cord atrophy. Three months following physiotherapy, his power improved to 5/5 in bilateral knee and hip joints and 4/5 in bilateral ankles with spasticity. Organophosphate-induced delayed neuropathy can present as earlier as 6 weeks with myelopathy. Previous history of organophosphorous exposure is important in myelopathy or peripheral neuropathy.
... Depending on the route of exposure and the bioavailability, OP compounds enter the blood following their absorption. Because of their lipophilic property, OP agents are usually distributed in the body, particularly within fatty tissues [15]. The mechanism of toxicity and pharmacological target of OP pesticides arise by the inhibition of AChE. ...
... The mechanism of toxicity and pharmacological target of OP pesticides arise by the inhibition of AChE. After this inhibition, ACh accumulates in synapses, which stimulates the cholinergic receptors, leading to muscarinic, nicotinic and CNS manifestations [15]. ...
Background: Diazinon (Dzn), an Organophosphorus (OP) pesticide, is extensively used in agriculture. Acetylcholinesterase inhibition is linked to OP toxicity, and there are major mental health concerns associated with the use of pesticides. The objective of this study was to assess the depressive behavior in an animal model following their exposure to Dzn and the effect on the Brain-Derived Neurotrophic Factor (BDNF) as a critical neurotropic factor.
Methods: Male Swiss mice (N=42; 25±3g each) were used and their behaviors were eamined on including the locomotor, Forced Swimming (FST), and Sucrose Preference (SP) tests. These tests were performed the day after a single daily Dzn administration by gavage (2.5-20 mg/kg). Specific animal groups were exposed to Dzn daily (2.5-10 mg/kg) for 14 days, and a test was performed on days 7 and 15.
Results: Following the acute exposure to Dzn, the animals’ locomotor activity did not change significantly. During the FST, Dzn at 20 mg/kg significantly increased the animals’ immobility time, indicating despair behavior. Imipramine, injected intraperitoneally at 10 mg/kg, did not cause the depressive behavior. The subacute exposure to Dzn induced less locomotor activity than that of the controls. The 7-day exposure to Dzn at 10 mg/kg significantly prolonged the immobility period compared to that of the controls. The 14-day Dzn exposure at 2.5, 5, or 10 mg/kg increased the immobility time significantly compared to that of the controls. None of the treatment groups showed SP, clearly showing animal anhedonia. The BDNF levels significantly decreased not only by subacute exposures to Dzn but also following a single exposure to this this pesticide.
Conclusion: The acute and subacute exposure to Dzn induced depressive behavior and increased the BDNF levels in the hippocampus of Swiss male mice following exposure to Dzn at varying doses of 2.5, 5, or 10 mg/kg.
... Organophosphates are esters of phosphoric acid and its derivatives, which inhibit acetylcholinesterase in nerve endings. They are liposoluble and volatile, which facilitates their absorption (Mangas et al., 2016). Their application is increasing in onion crops despite its toxicity (De Silva & Samayawardhena, 2002). ...
The Otún river basin, located in the Colombian coffee region, supplies water to more than 700,000 inhabitants of the department of Risaralda. Onion (Allium fistulosum) has been cultivated in this area since 1960, and currently represents an important economic contribution to local farmers who have assimilated intensive agricultural production models with the common use of chemical inputs. The objective of this research work is to identify management practices and their potential impact on the quality of water for human supply in the Otún River. Through surveys conducted among local producers, a general group of farmers with primary education was identified, who were not members of any producer association (≤9.1). Inadequate agricultural practices were identified on farms, where up to 1449 L ha -1 of diluted agrochemical inputs. Up to 70 different products with a great variety of toxicological categories (from a class of slightly toxic products (III) to extremely toxic products (Ia)), for the management of pests and diseases of onion crops. With the PIRI tool (Pesticide Impact Rating Index), a high impact of the mobility of pesticides towards water sources and the risk for the ecosystem and human beings was identified. Ten organochlorine pesticides and 16 organophosphate pesticides were detected in the water sources sampled.
... The data on neurotoxicity of OPs come from accidental human poisonings, epidemiological studies and animal models. In terms of the dose, it is considered low dose when no clinical manifestation is observed and the biomarker, serum cholinesterase level, is at more than 50% of its normal value, a medium dose is achieved when some clinical manifestations are observed like fatigue, headache, dizziness, numbness of extremities, nausea and vomiting, and the serum cholinesterase levels is between 10-50% of the normal value, high levels of exposure triggers severe clinical manifestations like marked miosis and loss of pupillary reflex to light, muscle fasciculation, flaccid paralysis, pulmonary rales, respiratory distress, cyanosis and unconsciousness which usually happens when the serum cholinesterase level is less than 10% of the normal value (Mangas et al. 2016) (Figure 2). ...
... Most insecticides are formulated in the form of phosphorothionates since they are more stable than the corresponding oxon forms such as parathion, chlorpyrifos and diazinon. Once the thiophosphate (with reduced capability to phosphorylate esterases) has been absorbed by the organism it is bioactivated and becomes the corresponding oxon form, with a high capability to phosphorylate esterases (toxic bioactivation) (Mangas et al. 2016). The reactions of phosphorothioates are catalyzed by either cytochrome P450 (CPY) yielding alkyl phosphates and phosphorothioates (Figure 4) or by NADPH-dependent enzymes involving the hydroxylation at the a-carbon atom of an alkyl group. ...
... The main enzymatic systems involved in the hydrolysis of OPs are phosphotriesterases (PTEs), carboxylesterases (CarbEs) and glutathione-S-transferases (GSTs). Several studies have reported that the OPs chlorpyrifos-oxon, diazoxon, O-hexyl O-2,5-dichlorophenyl phosphoramidate (HDCP), paraoxon and soman may be hydrolyzed by serum albumins from different species which is based on the phosphorylation of tyrosine 411 (Mangas et al. 2016). ...
Pesticides have a number of significant benefits to humans with improved crop yield and controlled vector populations. The pesticides such as organochlorines, organophosphates and carbamates cause toxicity by either targeting the nervous system of the prospective pests or by generating reactive oxygen species (ROS). Because humans are also exposed to them in the runaway process, there is an increasing risk of toxicity such as neurotoxicity or carcinogenicity. Apart from altering signal transduction pathways, disruption of protein phosphorylating pathways, hormonal impairment, etc., the pesticides interact with proteins, which may lead to various unexplored physiological consequences. Focusing on pesticides induced neurotoxicity, the interaction of pesticides with human serum albumin (HSA) and anti-proteinase alpha-2-macroglobulin (α2M) has been discussed in the review article. The article presents a possible unexplored mechanism of neurotoxicity of pesticides and their interaction with α2M, as it has a defensive role in the clearance of beta amyloid plaques in brain. This review also focuses on the possibilities of pesticide interaction with other non-plasma proteins leading to unknown biological consequences yet to be investigated.
... Organic P (Po) solubilization plays an essential role in P cycling in agroecosystems (Stamenković et al. 2018 (Mangas et al. 2016). Synthetic OCPs is highly toxic to animals (e.g. ...
... Organic P (Po) solubilization plays an essential role in P cycling in agroecosystems (Stamenković et al. 2018 (Mangas et al. 2016). Synthetic OCPs is highly toxic to animals (e.g. ...
This volume concentrates on the recent scientific advancements in agricultural biotechnology and reintegrates it with socio-economic, industrial and intellectual property aspects of agricultural biotechnology and its implications for accomplishing the sustainable development goals. Adopting a unique approach, this book amalgamates science and business perspectives from an insider’s viewpoint on the agro-biotech industry, laying the foundations for students and professionals alike.
