Chloramben's herbicidal action is primarily mediated through the inhibition of acetolactate synthase (ALS), a key enzyme in the biosynthesis of branched-chain amino acids (valine, leucine, and isoleucine). It binds to the active site of ALS, preventing the synthesis of these essential amino acids. This inhibition leads to the accumulation of toxic intermediates, ultimately causing cell death. Chloramben also interferes with the shikimate pathway, which is crucial for the biosynthesis of aromatic amino acids, and affects proteins involved in cell wall synthesis.

In vitro, Chloramben exerts significant effects on plant cells by inhibiting cell division and elongation. It interferes with hormone signaling, particularly auxins, which are crucial for plant growth and development. The compound also influences gene expression by altering the transcription of genes involved in cell cycle regulation and stress responses. Prolonged exposure to Chloramben can lead to the accumulation of reactive oxygen species, resulting in oxidative stress and cellular damage.

In vivo, Chloramben acts as a pre-emergence herbicide, preventing the growth of weeds as they emerge from the soil. It inhibits root and shoot development during seed germination, reducing competition for nutrients and water. Animal studies have shown that at low doses, the compound exhibits minimal toxicity, but at high doses, it can induce toxic effects, including liver and kidney damage. Chloramben can cause oxidative stress, inflammation, and apoptosis in various tissues in animal models.

In vitro enzyme assays for Chloramben typically measure its inhibition of acetolactate synthase (ALS) activity. The enzyme is incubated with its substrate (pyruvate) and the compound at varying concentrations, and the production of acetolactate is quantified. The IC50 value is determined from dose-response curves. Alternatively, the compound's effects on the shikimate pathway can be assessed by measuring the accumulation of shikimic acid in plant tissues. These assays confirm Chloramben's mechanism of action as an ALS inhibitor.

In vitro cell-based assays for Chloramben are conducted using plant cell cultures or seedlings. Plant cells or seedlings are treated with Chloramben at various concentrations, and cell division and elongation are assessed microscopically. The compound's effects on hormone signaling can be studied by measuring the expression of auxin-responsive genes. Oxidative stress markers, such as reactive oxygen species (ROS) levels, can be measured using fluorescent probes. These assays confirm the compound's herbicidal activity and its effects on plant cell physiology.

In vivo animal experiments for Chloramben have been conducted to assess its toxicity profile. In a typical study, rodents are administered Chloramben orally at various doses. The animals are observed for signs of toxicity, and organ weights and histopathology are examined. Blood samples are collected for clinical chemistry analysis. The compound's effects on oxidative stress, inflammation, and apoptosis are assessed in various tissues. These studies provide data on the compound's safety and potential toxic effects.

Absorption, Distribution and Excretion
A study on a lactating cow showed that over a 4-day period, dietary chlorobenzene (5 ppm daily) was rapidly excreted via urine (88%) and feces (5%). No residues were detected in the milk. Approximately 18% of the chlorobenzene in the urine was present in the form of unknown conjugates. Unpublished canine feeding studies… showed that dietary chlorobenzene (5 ppm) was rapidly excreted via urine and feces, and no residues were detected in collected tissue samples… Acidic compounds, such as 3-amino-2,5-dichlorobenzoic acid, bind to bovine serum albumin. The ratio of (14)C in the blood/tissue of rats treated with labeled acids was highly correlated with the logarithm of the binding affinity constant.

---

Metabolism/Metabolites
In tolerant and susceptible plant species, the major metabolic pathway of chloramphenicol appears to be the rapid formation of methanol-soluble conjugates and “bound” insoluble residues.
In plants, aniline is converted to N-glucosamine. An enzyme isolated from soybean… was found to be specific for uridine diphosphate-5'-glucose and its corresponding thymidine analogues.
…The long-term stability, immobility, and accumulation of N-glucosamine conjugates in vivo in susceptible and tolerant plants strongly suggest that N-glucosamine biosynthesis is a major detoxification mechanism.
3-Amino-2,5-dichlorobenzoic acid-N-glucosamine is produced in soybean, barley, beet, tomato, and cucumber. /Excerpt from Table/
Metabolism of Chloraniline in Plants. According to reported, the chlorobenzene-X conjugate was identified as methyl 3-amino-2,5-dichlorobenzoate (chlorobenzene methyl ester), a product formed during the purification of the methanol extract from the Florisil column by transesterification of an unknown ester metabolite.

---

Chloramben has a molecular weight of 206.02 g/mol and a molecular formula of C7H5Cl2NO2. It is a solid compound. For research use, it is typically supplied as a powder. It is soluble in organic solvents. For storage, it is recommended to keep the powder at -20°C. Detailed pharmacokinetic properties such as absorption, distribution, metabolism, and excretion (ADME) have not been extensively characterized for research purposes, as it is primarily used as a herbicide.

Toxicity Data
LC50 (Rat) > 200,000 mg/m³/1hr Interactions ...Caffeine and chlorobenzene react in the rat stomach to form an insoluble complex. Reduced gastrointestinal absorption of caffeine at 14°C is associated with incomplete dissociation of the chlorobenzene-caffeine complex in the intestine. Non-human Toxicity Values Oral LD50 in rats: 3,500 to 5,620 mg/kg Dermal LD50 in rabbits: 3,136 mg/kg

---

Chloramben is a herbicide and its toxicity has been studied in animal models. At low doses, the compound exhibits minimal toxicity and does not cause significant adverse effects. At high doses, Chloramben can induce toxic effects, including liver and kidney damage. Animal studies have shown that the compound can cause oxidative stress, inflammation, and apoptosis in various tissues. The threshold for toxic effects varies depending on the species and duration of exposure. As a research chemical, it should be handled with appropriate safety precautions.

[1]. On the performance of electrocatalytic anodes for photoelectro-Fenton treatment of synthetic solutions and real water spiked with the herbicide chloramben. J Environ Manage. 2018 Oct 15;224:340-349.

purplish-white powder or light purple solid. (NTP, 1992) Chloroaniline is a chlorobenzoic acid. It is used as a herbicide for various crops. Information on the health effects of chloroaniline is limited. Acute (short-term) exposure to high concentrations of chloroaniline in humans can cause mild to moderate skin irritation. There is currently no information on the chronic (long-term) effects of chloroaniline in humans. Animal studies report that long-term oral administration of chloroaniline can affect the liver. A study by the U.S. National Toxicology Program reported that oral administration of chloroaniline caused liver tumors in mice but did not infect rats. The U.S. Environmental Protection Agency has not listed chloroaniline as a potential carcinogen.

---

Chloramben is a pre-emergence herbicide belonging to the benzoic acid family. It is used for managing a wide range of weeds in vegetable and field crops. Its mechanism of action involves inhibiting seedling root development, primarily through the inhibition of acetolactate synthase (ALS). Chloramben is typically applied to soil before planting or crop emergence. It is a research compound used to study herbicide mechanisms and plant physiology. Chloramben is not approved for human or veterinary therapeutic use.

C7H5CL2NO2

204.02

204.969

133-90-4

1076-46-6 (ammonium salt);1954-81-0 (hydrochloride salt);28283-88-7 (aluminum salt)

8630

COLORLESS CRYSTALLINE SOLID

1.6±0.1 g/cm3

373.2±42.0 °C at 760 mmHg

200 °C

179.5±27.9 °C

0.0±0.9 mmHg at 25°C

1.658

2.52

2

3

1

12

188

0

C1=C(C=C(C(=C1C(=O)O)Cl)N)Cl

HSSBORCLYSCBJR-UHFFFAOYSA-N

InChI=1S/C7H5Cl2NO2/c8-3-1-4(7(11)12)6(9)5(10)2-3/h1-2H,10H2,(H,11,12)

3-amino-2,5-dichlorobenzoic acid

Amiben DS Amoben Amibin

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~250 mg/mL (~1213.42 mM)

Solubility in Formulation 1: ≥ 2.08 mg/mL (10.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

---

Solubility in Formulation 2: ≥ 2.08 mg/mL (10.10 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

---

View More

Solubility in Formulation 3: ≥ 2.08 mg/mL (10.10 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

---

 (Please use freshly prepared in vivo formulations for optimal results.)