Investigations on herbicides III: 2,4‐Disubstituted 6‐chloro‐1,3,5‐triazines

Koopman, H.; Daams, J.

doi:10.1002/recl.19600790109

Cited by 9 publications

(4 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2,6-Dichlorothiobenzamide (Prefix) (Yates, 1961) and 2,6-dichlorobenzonitrile (Belgian Patent, 1957) are promising herbicides with interesting biological properties (Barnsley, 1960; Koopman & Daams, 1960). Prefix is useful as a selective herbicide in transplanted rice.…”

mentioning

confidence: 99%

See 1 more Smart Citation

The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

Griffiths¹,

Moss²,

Rose³

et al. 1966

Biochemical Journal

View full text Add to dashboard Cite

1. A single oral dose of either [(14)C]Prefix or 2,6-dichlorobenzo[(14)C]nitrile to rats is almost entirely eliminated in 4 days: 84.8-100.5% of (14)C from [(14)C]Prefix is excreted, 67.3-79.7% in the urine, and 85.8-97.2% of (14)C from 2,6-dichlorobenzo-[(14)C]nitrile is excreted, 72.3-80.7% in the urine. Only 0.37+/-0.03% of the dose of [(14)C]Prefix and 0.25+/-0.03% of the dose of 2,6-dichlorobenzo[(14)C]nitrile are present in the carcass plus viscera after removal of the gut. Rats do not show sex differences in the pattern of elimination of the respective metabolites of the two herbicides. The rates of elimination of (14)C from the two compounds in the 24hr. and 48hr. urines are not significantly different (P >0.05) from one another. 2. After oral administration to dogs, 85.9-106.1% of (14)C from [(14)C]Prefix is excreted, 66.6-80.9% in the urine, and 86.8-92.5% of (14)C from 2,6-dichlorobenzo[(14)C]nitrile is excreted, 60.0-70.1% in the urine. Dogs do not show sex differences in the pattern of eliminating the metabolites of either Prefix or 2,6-dichlorobenzonitrile. 3. Dogs and rats do not show species differences in the patterns of elimination of the two herbicides. 4. Prefix and 2,6-dichlorobenzonitrile are completely metabolized; unchanged Prefix and 2,6-dichlorobenzonitrile are absent from the urine and faeces, and from the carcasses when elimination is complete. In the hydrolysed urine of rats dosed with either [(14)C]Prefix or 2,6-dichlorobenzo[(14)C]nitrile, 2,6-dichloro-3-hydroxybenzonitrile accounts for approx. 42% of the (14)C, a further 10-11% is accounted for by 2,6-dichlorobenzamide, 2,6-dichlorobenzoic acid, 2,6-dichloro-3- and -4-hydroxybenzoic acid and 2,6-dichloro-4-hydroxybenzonitrile collectively, and 25-30% by six polar constituents, of which two are sulphur-containing amino acids. 5. In the unhydrolysed urines of rats dosed with either [(14)C]Prefix or 2,6-dichlorobenzo[(14)C]nitrile, there are present free 2,6-dichloro-3- and -4-hydroxybenzonitrile, their glucuronide conjugates, ester glucuronides of the principal aromatic acids that are present in the hydrolysed urines, and two sulphur-containing metabolites analogous to mercapturic acids or premercapturic acids. 6. Prefix is thus extensively transformed into 2,6-dichlorobenzonitrile: R.CS.NH(2)-->R.CN+H(2)S, where R=C(6)H(3)Cl(2). However, the competitive reaction: R.CS.NH(2)+H(2)O-->R.CO.NH(2)+H(2)S takes place to a very limited extent.

show abstract

mentioning

confidence: 99%

“…MATERIALS 2,6-Dichlorobenzonitrile. This was prepared by dehydration in boiling acetic anhydride of anti-2,6-dichlorobenzaldoxime (Koopman, 1961), which was itself prepared by reaction of 2,6-dichlorobenzaldehyde (Fierz-David & Blangey, 1952; Reich, 1917) with hydroxylamine monosulphonate (Koopman, 1961). 2,6-Dichlorobenzonitrile had m.p.…”

mentioning

confidence: 99%

The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

Griffiths¹,

Moss²,

Rose³

et al. 1966

Biochemical Journal

View full text Add to dashboard Cite

show abstract

“…2,4‐Diallyloxy‐6‐chloro‐1,3,5‐triazine (4): Allyl alcohol (4.10 mL, 60.3 mmol) and ethyldiisopropylamine (10.5 mL, 60.3 mmol) were added to a solution of cyanuric chloride (3.69 g, 20.0 mmol) in CH 2 Cl 2 (40 mL) at –10 °C. The reaction mixture was warmed to room temperature and stirred for 24 h. The reaction mixture was poured into saturated aqueous NaHCO 3 (100 mL) and then extracted with CH 2 Cl 2 (3 × 20 mL).…”

Section: Methodsmentioning

confidence: 99%

Preparation of Alkyl Ethers with Diallyltriazinedione‐Type Alkylating Agents (ATTACKs‐R) Under Acid Catalysis

et al. 2019

View full text Add to dashboard Cite

Diallyltriazinedione‐type acid‐catalyzed alkylating agents (ATTACKs‐R) with 10 different alkyl groups (R), including benzyl, substituted benzyl, allyl, and methyl groups were synthesized. The palladium‐catalyzed intramolecular O‐to‐N allylic rearrangement of 2,4‐bis(allyloxy)‐6‐chloro‐1,3,5‐triazine was developed to introduce various alkoxy groups into the N,N′‐dialkylated triazinedione skeleton. O‐Alkylation of alcohols with ATTACKs‐R was carried out in 1,4‐dioxane in the presence of 2,6‐di‐tert‐butylpyridinium trifluoromethanesulfonate or trifluoromethanesulfonic acid as a catalyst. Six selected ATTACKs‐R bearing benzylic R groups were employed to prepare alkyl ethers from primary, secondary, and tertiary alcohols. The reactions of ATTACKs‐R bearing an o‐nitro‐substituted benzyl group tended to afford low yields. Comparison of four different triazinedione‐based benzylating reagents suggested that the N,N′‐substituents affected the reactivity.

show abstract

“…(5 g, 88 %). 1 Hydrazine monohydrate (0.64g, 12.75 mmol) was added dropwise to a suspension of 2-chloro-4,6-bis(ethylthio)- [1,3,5]triazine [33] (6.0g, 25.5 mmol) and NaOH (1.9g, 47.5 mmol) in toluene (50 mL). The mixture was stirred at 80 °C for 3 h. After cooling the mixture to ambient temperature, it was extracted twice with water (25 mL …”

Section: General Considerationsmentioning

confidence: 99%

Preparation and characterization of bis‐[1,3,5]triazinyl diazenes and their utilization as flame retardants in polypropylene films

Tirri

Aubert

Pawelec

et al. 2014

J of Applied Polymer Sci

View full text Add to dashboard Cite

A series of bis- [1,3,5]triazinyl diazenes and two metal complexes thereof were synthesized and tested as new flame retardants in polypropylene films. It was observed that electron withdrawing triazinyl ring substituents (i.e. Cl and phenyl moieties) improved the thermal stability of diazene compounds, whereas electron donating groups (i.e. methoxy, dimethylamino and ethylthio moieties) had a destabilizing effect. TGA, DTA/DSC, NMR and ATR-FTIR were used for the characterization. Quantum mechanical modeling (Gaussian 09) was also utilized to facilitate the interpretation of the NMR data. Bis-(4,6-dichloro-[1,3,5]triazin-2-yl)-diazene 1 and bis-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-diazene 2 were found to be effective flame retardants in polypropylene films and DIN4102-1 B2 classification was reached already at a loading of 0.5 wt%. Interestingly, the copper complex of 2 showed even higher fire retardant activity than its precursor 2, whereas the corresponding zinc complex exhibited lower flame retardant efficacy than its precursor.

show abstract

Investigations on herbicides III: 2,4‐Disubstituted 6‐chloro‐1,3,5‐triazines

Cited by 9 publications

References 5 publications

The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

Preparation of Alkyl Ethers with Diallyltriazinedione‐Type Alkylating Agents (ATTACKs‐R) Under Acid Catalysis

Preparation and characterization of bis‐[1,3,5]triazinyl diazenes and their utilization as flame retardants in polypropylene films

Contact Info

Product

Resources

About