2582-16-3

Basic information

• Product Name: 2,2,5,5-tetramethylimidazolidine-4-thione
• Synonyms: 2,2,5,5-tetramethylimidazolidine-4-thione
• CAS NO: 2582-16-3
• Molecular Formula: C₇H₁₄N₂S
• Molecular Weight: 158.26
• Mol File: 2582-16-3.mol

Chemical Properties

• Boiling Point: 199.7°Cat760mmHg
• Flash Point: 74.6°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 0.338mmHg at 25°C
• CAS DataBase Reference: 2,2,5,5-tetramethylimidazolidine-4-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,5,5-tetramethylimidazolidine-4-thione(2582-16-3)
• EPA Substance Registry System: 2,2,5,5-tetramethylimidazolidine-4-thione(2582-16-3)

Safety Data

• Hazardous Substances Data: 2582-16-3(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
2,2,5,5-tetramethylimidazolidine-4-thione is used as a fungicide for protecting crops from fungal diseases, ensuring a healthy and productive yield. Its application helps in controlling various fungal infections that could otherwise damage or destroy crops.
Used in Horticultural Industry:
In horticulture, 2,2,5,5-tetramethylimidazolidine-4-thione is used as a pesticide to maintain the health and appearance of plants. It is particularly effective in preventing and treating fungal infections that can affect the growth and aesthetic appeal of ornamental plants.
Used as a Seed Treatment:
2,2,5,5-tetramethylimidazolidine-4-thione is used as a seed treatment to prevent seed rot and damping-off, which are common issues that can affect the germination and early growth of plants. By applying thiram to seeds, it helps to create a protective barrier against fungal pathogens, promoting healthy seedling establishment.

InChI:InChI=1/C7H14N2S/c1-6(2)5(10)8-7(3,4)9-6/h9H,1-4H3,(H,8,10)/p+1

Upstream product

• 13922-03-7 2,2'-iminobis(2-methylpropionitrile) 
• 19355-69-2 2-amino-2-cyanopropane 
• 67-64-1 acetone 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 773837-37-9 sodium cyanide 
• 50846-36-1 2-amino-2-methylpropanenitrile monohydrochloride 
• 5496-10-6 1-amino-1-cyanocyclohexane 

Downstream Products

• 16256-42-1 2,2,5,5-tetramethyl-4-oxoimidazolidine 
• 1310681-37-8 C₁₈H₂₈N₂O₂*ClH 
• 1310681-36-7 BrH*C₁₈H₂₈N₂O₂ 
• 62-57-7 2-Aminoisobutyric acid 
• 5448-29-3 N-(2-aminoisobutyl)isopropylamine 

Relevant articles and documents

Prebiotically Plausible Organocatalysts Enabling a Selective Photoredox α-Alkylation of Aldehydes on the Early Earth

Organocatalysis is a powerful approach to extend and (enantio-) selectively modify molecular structures. Adapting this concept to the Early Earth scenario offers a promising solution to explain their evolution into a complex homochiral world. Herein, we present a class of imidazolidine-4-thione organocatalysts, easily accessible from simple molecules available on an Early Earth under highly plausible prebiotic reaction conditions. These imidazolidine-4-thiones are readily formed from mixtures of aldehydes or ketones in presence of ammonia, cyanides and hydrogen sulfide in high selectivity and distinct preference for individual compounds of the resulting catalyst library. These organocatalysts enable the enantioselective α-alkylation of aldehydes under prebiotic conditions and show activities that correlate with the selectivity of their formation. Furthermore, the crystallization of single catalysts as conglomerates opens the pathway for symmetry breaking.

Dynamic Exchange of Substituents in a Prebiotic Organocatalyst: Initial Steps towards an Evolutionary System

All evolutionary biological processes lead to a change in heritable traits over successive generations. The responsible genetic information encoded in DNA is altered, selected, and inherited by mutation of the base sequence. While this is well known at the biological level, an evolutionary change at the molecular level of small organic molecules is unknown but represents an important prerequisite for the emergence of life. Here, we present a class of prebiotic imidazolidine-4-thione organocatalysts able to dynamically change their constitution and potentially capable to form an evolutionary system. These catalysts functionalize their building blocks and dynamically adapt to their (self-modified) environment by mutation of their own structure. Depending on the surrounding conditions, they show pronounced and opposing selectivity in their formation. Remarkably, the preferentially formed species can be associated with different catalytic properties, which enable multiple pathways for the transition from abiotic matter to functional biomolecules.

Novel N-chloroheterocyclic antimicrobials

Antimicrobial compounds with broad-spectrum activity and minimal potential for antibiotic resistance are urgently needed. Toward this end, we prepared and investigated a novel series of N-chloroheterocycles. Of the compounds examined, the N-chloroamine series were found superior over N-chloroamide series in regards to exhibiting high antimicrobial activity, low cytotoxicity, and long-term aqueous stability.

Process for production of additives for lubricating oils

A method for making a compound of formula (I) wherein bonds a and b are single or double bonds, provided that one of a and b is a single bond and the other is a double bond; one of B1 and B2 is -CHR5-CHR6-C(Y)ZR7, -CR10R11-NHR12 or hydrogen and the other is absent; B3 is -C(W)NHR8 or hydrogen; provided that one of B1, B2 and B3 is not hydrogen; Y and W are O or S; Z is O, S or NR9; R5 is hydrogen or C1-C4 alkyl; R6 is hydrogen or C1-C4 alkyl; R7, R9, R10 and R11 are independently hydrogen, alkyl, alkenyl, aryl or aralkyl; and R8 and R12 independently are alkyl, alkenyl, aryl or aralkyl. The method comprises steps of: (a) preparing an imidazolidinethione having formula and (b) adding to the imidazolidinethione, without isolation of the imidazolidinethione, one of: (i) CHR5=CHR6-C(Y)ZR7; (ii) R10R11C=O and R12NH2; (iii) R10R11C=NR12; and (iv) R8N=C=W.

Imidazolidinone derivatives

A compound of the formula (IA) or (IB) wherein G1, G2, G3 and G4 are independently of one another C1-C18alkyl or C5-C12cycloalkyl or the radicals G1 and G2 and the radicals G3 and G4 form independently of one another, together with the carbon atom they are attached to, C5-C12cycloalkyl; R is hydrogen C1-C18alkyl, C1-C18hydroxyalkyl, C2-C18alkenyl, C5-C12cycloalkyl, C7-C12phenylalkyl unsubstituted or substituted on the phenyl radical by C1-C4alkyl and/or C1-C4alkoxy; or C1-C18alkanoyl; R* is hydrogen, C1-C18alkyl, oxyl, —OH, —CH2CN, C3-C6alkenyl, C3-C8alkynyl, C7-C12phenylalkyl unsubstituted or substituted on the phenyl radical by C1-C4alkyl and/or C1-C4alkoxy; C1-C8acyl, C1-C18alkoxy, C1-C18hydroxyalkoxy, C2-C18alkenyloxy, C5-C12cycloalkoxy, C7-C12phenylalkoxy unsubstituted or substituted on the phenyl radical by C1-C4alkyl and/or C1-C4alkoxy; C1-C18alkanoyloxy, (C1-C18alkoxy)carbonyl, glycidyl or a group —CH2CH(OH)(G) with G being hydrogen, methyl or phenyl; n is 1, 2, 3 or 4; n* is 1, 2 or 3; X is an organic radical of a valency equal to n; and X* is a triazinic radical with a valency equal to n*; with the proviso that when n is 1, R is methyl, ethyl, propyl, C1-C18hydroxyalkyl, C2-C18alkenyl, C5-C12cycloalkyl or C1-C18alkanoyl. The compounds described above are useful for stabilizing an organic material against degradation induced by light, heat or oxidation.

Thioimidazolidine derivatives as light stabilizers for polymers

A compound of the formula (I) wherein G1, G2, G3 and G4 are independently of one another C1-C18alkyl or C5-C12cycloalkyl or the radicals G1 and G2 and the radicals G3 and G4 form independently of one another, together with the carbon atom they are attached to, C5-C12cycloalkyl; R is hydrogen, C1-C18alkyl, oxyl, —OH, —CH2CN, C3-C6alkenyl, C3-C8alkynyl, C7-C12phenylalkyl unsubstituted or substituted on the phenyl radical by C1-C4alkyl and/or C1-C4alkoxy; C1-C8acyl, C1-C18alkoxy, C1-C18hydroxyalkoxy, C2-C18alkenyloxy, C5-C12cycloalkoxy, C7-C12phenylalkoxy unsubstituted or substituted on the phenyl radical by C1-C4alkyl and/or C1-C4alkoxy: C1-C18alkanoyloxy, (C1-C18alkoxy)carbonyl, glycidyl or a group —CH2CH(OH)(G) with G being hydrogen, methyl or phenyl; n is 1, 2, 3 or 4; and X is an organic radical of a valency equal to n; and when n is 2, 3 or 4, each of the radicals G1, G2, G3, G4 and R can have the same or a different meaning in the units of the formula (II), is useful for stabilizing an organic material against degradation induced by light, heat or oxidation.

Thioimidazolidine derivatives as oil-soluble additives for lubricating oils

A compound of formula I: ???wherein W represents O, S-A2, or two groups, R3 and R4; bonds a and b are single or double bonds, provided that one of a and b is a single bond and the other is a double bond; c is a single or double bond, and d is a single bond, double bond, or two single bonds, provided that d is a single bond when c is a double bond, d is not a single bond when c is a single bond, and W is R3 and R4 when d is two single bonds; ???A1, A2, B1 and B2 are independently hydrogen, alkyl, alkenyl, aralkyl or one of the groups depicted in Scheme 1: useful as oil-soluble additives for lubricating oils.

N,N'-dihaloimidazolidin-4-ones

Substituted N-halo derivatives of imidazolidin-4-ones having substituents at the 2 and 5 positions of the imidazolidin-4-one ring are described. More particularly, there are described N-chloro, N-bromo, N,N'-dichloro, N,N'-dibromo, and N,N'-bromochloro derivatives of imidazolidin-4-ones having substituents selected from hydrogen, alkyl, alkoxy, hydroxy, phenyl, substituted phenyl, or spiro-substitution at the 2 and 5 positions on the ring. These N-halo compounds are stable, noncorrosive biocides which are resistant to direct sunlight, and are useful as disinfectants, sanitizers, and algae inhibitors.

Preparation of α-aminothioamides from aldehydes

The conversion of aldehydes into α-aminonitriles and thence into imidazolidin-4-thiones has been studied.Hydrolysis of the appropriate imidazolidin-4-thiones gave thioamides of nine naturally occuring α-amino acids.The possible pre-biotic significance of these compounds is discussed.