Tools to study the degradation and loss of the N-phenyl carbamate chlorpropham — A comprehensive review

Smith, Margaret J.; Bucher, Götz

doi:10.1016/j.envint.2012.08.005

Cited by 33 publications

(28 citation statements)

References 77 publications

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“…Similar reactions occur in many chemical and biochemical processes. Smith and Bucher (54) reported that chlorpropham was transformed into carbamic acid when the temperature was Ͼ45°C; however, carbamic acid is unstable and readily decarboxylates to yield m-chloroaniline (54). Sphingomonas sp.…”

Section: Resultsmentioning

confidence: 99%

Metabolic Pathway Involved in 6-Chloro-2-Benzoxazolinone Degradation by Pigmentiphaga sp. Strain DL-8 and Identification of the Novel Metal-Dependent Hydrolase CbaA

Dong

Wang

Huang

et al. 2016

Appl Environ Microbiol

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ABSTRACT6-Chloro-2-benzoxazolinone (CDHB) is a precursor of herbicide, insecticide, and fungicide synthesis and has a broad spectrum of biological activity. Pigmentiphaga sp. strain DL-8 can transform CDHB into 2-amino-5-chlorophenol (2A5CP), which it then utilizes as a carbon source for growth. The CDHB hydrolase (CbaA) was purified from strain DL-8, which can also hydrolyze 2-benzoxazolinone (BOA), 5-chloro-2-BOA, and benzamide. The specific activity of purified CbaA was 5,900 U · mg protein ؊1for CDHB, with K m and k cat values of 0.29 mM and 8,500 s ؊1 , respectively. The optimal pH for purified CbaA was 9.0, the highest activity was observed at 55°C, and the inactive metal-free enzyme could be reactivated by Mg 2؉ , Ni 2؉ , Ca 2؉ , or Zn 2؉ . Based on the results obtained for the CbaA peptide mass fingerprinting and draft genome sequence of strain DL-8, cbaA (encoding 339 amino acids) was cloned and expressed in Escherichia coli BL21(DE3). CbaA shared 18 to 21% identity with some metal-dependent hydrolases of the PF01499 family and contained the signature metal-binding motif Q 127 XXXQ 131 XD 133 XXXH 137 . The conserved amino acid residues His288 and Glu301 served as the proton donor and acceptor. E. coli BL21(DE3-pET-cbaA) resting cells could transform 0.2 mM CDHB into 2A5CP. The mutant strain DL-8⌬cbaA lost the ability to degrade CDHB but retained the ability to degrade 2A5CP, consistent with strain DL-8. These results indicated that cbaA was the key gene responsible for CDHB degradation by strain DL-8. IMPORTANCE2-Benzoxazolinone (BOA) derivatives are widely used as synthetic intermediates and are also an important group of allelochemicals acting in response to tissue damage or pathogen attack in gramineous plants. However, the degradation mechanism of BOA derivatives by microorganisms is not clear. In the present study, we reported the identification of CbaA and metabolic pathway responsible for the degradation of CDHB in Pigmentiphaga sp. DL-8. This will provide microorganism and gene resources for the bioremediation of the environmental pollution caused by BOA derivatives. 6-Chloro-2-benzoxazolinone (CDHB) is the precursor of fenoxaprop-p-ethyl (FE) and metamifop synthesis (1). FE is a postemergence aryloxyphenoxy propionate (AOPP) herbicide that is used to control annual and perennial weeds in crops, such as soybean, turf, and wheat (2, 3). Many studies have demonstrated that FE can be hydrolyzed to fenoxaprop acid (FA) and further transformed into CDHB and 2-(4-hydroxyphenoxy)-propionic acid (HPP) by soil microorganisms (4-6). Recently, the hydrolysis of FE to FA by several esterases from different microorganisms has been reported (7-9). However, the underlying genes and the metabolic pathway responsible for the degradation of CDHB in microorganisms are unknown.CDHB is a type of 2-benzoxazolinone (BOA) derivative. BOA is widely used as a synthetic intermediate of related derivatives and is an important group of allelochemicals that respond to tissue damage or pathogen attack in gramineous plants, s...

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Section: Resultsmentioning

confidence: 99%

Metabolic Pathway Involved in 6-Chloro-2-Benzoxazolinone Degradation by Pigmentiphaga sp. Strain DL-8 and Identification of the Novel Metal-Dependent Hydrolase CbaA

Dong

Wang

Huang

et al. 2016

Appl Environ Microbiol

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“…& Once CIPC enters in human/mammals, animal and plant/ potato tubers, it degrades into metabolites such as 3-CA; isopropyl N-4 hydroxy-3-chlorophenyl carbamate; isopropyl-N-5-chloro-2-hydroxyphenyl carbamate; 3, 3′-dichloro azobenzene; p-methoxy-chlorpropham; 3-chloro-4 hydroxyaniline; 3-chloro-4 methoxyaniline; 1-hydroxy-2 propyl-3-chlorocarbanilate and 3′-c h l o r o a c e t a n i l i d e ; i s o p r o p y l N -( 3 -c h l o r o -4 -methoxyphenyl) carbamate; isopropyl N-(3-chloro-4-hydroxyphenyl) carbamate etc. (Davis et al 1977;Kidd and James 1991;Carrera et al 1998;Orejuela and Silva 2005;Balaji et al 2006;Smith and Bucher 2012). These metabolites are reported to be cytolytic, highly toxic, carcinogenic, cause reduction in ATP synthesis, bring about modifications in cell permeability besides being pollutants (Davis et al 1977;Heikes 1985;Kidd and James 1991;Carrera et al 1998;Balaji et al 2006;Smith and Bucher 2012).…”

Section: Some Important Safety Issues and Environmental Concerns Relamentioning

confidence: 99%

“…Carbamates break down to aniline based derivatives which have high toxicity profile (Balaji et al 2006). One of such breakdown product of CIPC is 3-chloroaniline (3-CA) and being aniline based derivative this is considered more polluting and highly toxic than the parent compound itself (Park 2004;Orejuela and Silva 2005;Balaji et al 2006;Sihtmaee et al 2010;Smith and Bucher 2012). As per Mohammed et al (2014Mohammed et al ( , 2015, 3-CA is aromatic amine and dangerous to human and environment.…”

Section: Some Important Safety Issues and Environmental Concerns Relamentioning

confidence: 99%

“…As per Mohammed et al (2014Mohammed et al ( , 2015, 3-CA is aromatic amine and dangerous to human and environment. The potential/possible danger with respect to 3-CA can be realized from the fact that other 2 derivatives of aniline i.e., 2-chloroaniline and 4-chloroaniline are already classified as hazardous substances which are possibly carcinogenic to humans (Sihtmaee et al 2010;Smith and Bucher 2012). The big concern over 3-CA is because it is structurally similar to 4-CA but at the same time chemical structure of CIPC is such that 3-CA and not the 4-CA is produced as one of the metabolic products (Mohammed 2012).…”

Section: Some Important Safety Issues and Environmental Concerns Relamentioning

confidence: 99%

“…World over, isopropyl N-(3-chlorophenyl) carbamate (CIPC also referred as chlorpropham) is the most commonly used sprout suppressant on potatoes when stored at 8-12°C (Smith and Bucher 2012). CIPC is primarily an herbicide which was introduced in the year 1951 (Marth and Schultz 1952).…”

Section: Introductionmentioning

confidence: 99%

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Sprout suppression on potato: need to look beyond CIPC for more effective and safer alternatives

2015

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World over, potatoes are being stored at [8][9][10][11][12]. This is the most common way of long-term (up to 6 to 9 months) storage of potatoes. The benefit of storing the potatoes within the temperature range of 8-12°C is minimum accumulation of sugars in stored potato tubers. In sub-temperate, sub-tropical and tropical countries of the world, short-term (3 to 4 months) storage of potatoes is being done by non-refrigerated traditional/on-farm methods. These short-and long-term storage methods keep the stored potatoes suitable not only for table purpose but also for processing. However, once the natural dormancy period of potato is over, the prevailing temperatures in these storage methods favour sprouting and sprout growth. Therefore, use of some sprout suppressant to check the sprout growth becomes essential under these methods of potato storage. CIPC [Isopropyl N-(3-chlorophenyl) carbamate] is the most wide spread and commonly used sprout suppressant on potatoes. CIPC has been in use for more than 50 years and research carried out over such a long period use of CIPC has not only enhanced our understanding of its properties and chemistry but also about the production and toxicological status of its metabolites/ degradation products. Today, various safety issues and concerns have surfaced primarily due to continuous and longterm use of CIPC. This review presents an appraisal on CIPC and explains the reasons for the long-time dependence on this chemical as a potato sprout suppressant. Issues like maximum residue limit and acceptable daily intake limit are being discussed for CIPC. This article brings an update on practical aspects of potato storage, residue levels of CIPC, efficacy of CIPC as sprout suppressant and health and environmental safety issues linked with CIPC and its metabolites. The aim of this article is to find possible solutions, way outs and future plans that can make the sprout suppression of potatoes safer and more risk free.

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Pesticides

Abou‐Donia¹

2015

Mammalian Toxicology

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Tools to study the degradation and loss of the N-phenyl carbamate chlorpropham — A comprehensive review

Cited by 33 publications

References 77 publications

Metabolic Pathway Involved in 6-Chloro-2-Benzoxazolinone Degradation by Pigmentiphaga sp. Strain DL-8 and Identification of the Novel Metal-Dependent Hydrolase CbaA

Metabolic Pathway Involved in 6-Chloro-2-Benzoxazolinone Degradation by Pigmentiphaga sp. Strain DL-8 and Identification of the Novel Metal-Dependent Hydrolase CbaA

Sprout suppression on potato: need to look beyond CIPC for more effective and safer alternatives

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