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Chemistry

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Also known as: 1-(2-methylcyclohexyl)-3-phenylurea, 1982-49-6, Tupersan, Trey, Urea, n-(2-methylcyclohexyl)-n'-phenyl-, Du pont herbicide 1,318
Molecular Formula
C14H20N2O
Molecular Weight
232.32  g/mol
InChI Key
JXVIIQLNUPXOII-UHFFFAOYSA-N
FDA UNII
513S964LJO

Siduron
1 2D Structure

Siduron

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(2-methylcyclohexyl)-3-phenylurea
2.1.2 InChI
InChI=1S/C14H20N2O/c1-11-7-5-6-10-13(11)16-14(17)15-12-8-3-2-4-9-12/h2-4,8-9,11,13H,5-7,10H2,1H3,(H2,15,16,17)
2.1.3 InChI Key
JXVIIQLNUPXOII-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1CCCCC1NC(=O)NC2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
513S964LJO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(2-methylcyclohexyl)-3-phenylurea

2.3.2 Depositor-Supplied Synonyms

1. 1-(2-methylcyclohexyl)-3-phenylurea

2. 1982-49-6

3. Tupersan

4. Trey

5. Urea, N-(2-methylcyclohexyl)-n'-phenyl-

6. Du Pont Herbicide 1,318

7. Du Pont 1318

8. N-phenyl-n'-(2-methylcyclohexyl)urea

9. Urea, 1-(2-methylcyclohexyl)-3-phenyl-

10. 1-(2-methylcycohexyl)-3-phenylurea

11. H 1318

12. Nsc 131951

13. Chebi:81744

14. 513s964ljo

15. Nsc-131951

16. Urea,n-(2-methylcyclohexyl)-n'-phenyl-

17. Caswell No. 733a

18. Dupont 1318

19. Siduron [ansi:bsi:iso]

20. Siduron [iso]

21. Hsdb 1764

22. Einecs 217-844-2

23. Epa Pesticide Chemical Code 035509

24. N-(2-methylcyclohexyl)-n'-phenylurea

25. Unii-513s964ljo

26. Siduron [mi]

27. Dsstox_cid_12474

28. Dsstox_rid_78952

29. Dsstox_gsid_32474

30. Schembl66323

31. Wln: L6tj Amvmr& B1

32. Chembl1902120

33. Dtxsid7032474

34. Tox21_301425

35. Nsc131951

36. Akos001192124

37. Ncgc00163937-01

38. Ncgc00163937-02

39. Ncgc00255363-01

40. N-(2-methylcyclohexyl)-n'-phenylurea #

41. Cas-1982-49-6

42. Siduron, Pestanal(r), Analytical Standard

43. C18435

44. N-(2-methylcyclohexyl)-n'-phenylurea [hsdb]

45. Q27155591

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 232.32 g/mol
Molecular Formula C14H20N2O
XLogP33.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass232.157563266 g/mol
Monoisotopic Mass232.157563266 g/mol
Topological Polar Surface Area41.1 Ų
Heavy Atom Count17
Formal Charge0
Complexity249
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

Most readily absorbed through root system; less so through foliage and stems. ... Experimental evidence indicates that Siduron is translocated in the xylem.

Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 427


4.2 Metabolism/Metabolites

Urine from a dog receiving 2500 ppm siduron in the diet was collected and analyzed for the parent compound and metabolites using a colorimetric method, and mass, IR, and NMR spectrometry, and a metabolic pathway was proposed; none of the parent compound was found, but three glucuronide conjugates of hydroxysubstituted siduron were isolated and identified, one substituted on the phenyl ring, one substituted on the cyclohexyl ring, and another substituted in both locations; it appears that siduron is first hydroxylated at either location, then both of these mono-hydroxylated compounds are hydroxylated again to form 1-(4-hydroxy-2-methylcyclo-hexyl)-3-p-hydroxyphenylurea; comparison of urine from the dog with that from a rat on a similar 2500 ppm diet, showed that the rat formed slightly less of the cyclohexyl-substituted compound than the dog; 800-1000 ppm of total siduron metabolites was bound in the urine of these two animals.

California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Siduron (1982-49-6). Available from, as of May 13, 2009: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


In studies with (14)C-labeled siduron, no metabolites ... were detectable in barley plants after an 8 day absorption period.

Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 427


... Both phenyl and cyclohexyl rings are subjected to hydroxylation in the dog. ... The pathways proposed ... show that siduron is either hydroxylated at para position of phenyl nucleus or at 4 position of 2-methylcyclohexyl moiety. Both metabolites are further hydroxylated to form 1-(4-hydroxy-2-methylcyclohexyl)-3-(p-hydroxyphenyl)urea.

Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 246


When urine samples of both dogs and rats were subjected to hydrolysis and analyzed for aminophenol /as well as/ aniline, it was observed that hydroxylation of the phenyl moiety was more prominent in the rat than in dog. Apparently rats exhibit particular efficiency in hydroxylating the aromatic nucleus of phenylureas. In another study in which (14)C- carbonyl-labeled compound was applied ... microbial degradation was major route of siduron disappearance in soil. Metabolites separated on thin-layer plates had same characteristics as those identified in urine, and /it was/ ... concluded that ring hydroxylation was also operative in soil environment.

Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 246


For more Metabolism/Metabolites (Complete) data for SIDURON (6 total), please visit the HSDB record page.


4.3 Mechanism of Action

Unlike other substituted urea herbicides, siduron is not a potent inhibitor of photosynthesis; phytotoxic symptoms appear to be associated with root growth inhibition.

Weed Science Society of America. Herbicide Handbook. 5th ed. Champaign, Illinois: Weed Science Society of America, 1983., p. 427


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PharmaCompass offers a list of Siduron API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Siduron manufacturer or Siduron supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Siduron manufacturer or Siduron supplier.

PharmaCompass also assists you with knowing the Siduron API Price utilized in the formulation of products. Siduron API Price is not always fixed or binding as the Siduron Price is obtained through a variety of data sources. The Siduron Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Siduron

Synonyms

1-(2-methylcyclohexyl)-3-phenylurea, 1982-49-6, Tupersan, Trey, Urea, n-(2-methylcyclohexyl)-n'-phenyl-, Du pont herbicide 1,318

Cas Number

1982-49-6

Unique Ingredient Identifier (UNII)

513S964LJO

Siduron Manufacturers

A Siduron manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Siduron, including repackagers and relabelers. The FDA regulates Siduron manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Siduron API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Siduron Suppliers

A Siduron supplier is an individual or a company that provides Siduron active pharmaceutical ingredient (API) or Siduron finished formulations upon request. The Siduron suppliers may include Siduron API manufacturers, exporters, distributors and traders.

Siduron GMP

Siduron Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Siduron GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Siduron GMP manufacturer or Siduron GMP API supplier for your needs.

Siduron CoA

A Siduron CoA (Certificate of Analysis) is a formal document that attests to Siduron's compliance with Siduron specifications and serves as a tool for batch-level quality control.

Siduron CoA mostly includes findings from lab analyses of a specific batch. For each Siduron CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Siduron may be tested according to a variety of international standards, such as European Pharmacopoeia (Siduron EP), Siduron JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Siduron USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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