ISO Common Name Chemical Name Empirical Formula RMM M.P. V.P. Solubility

TRIADIMENOL 398
TRIADIMENOL
398
ISO common name Triadimenol

Chemical name 1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-
triazol-1-yl)butan-2-ol (IUPAC); (CA; 55219-65-3)
Empirical formula C14H18ClN3O2
RMM 295.8
m.p. 138.2 °C
v.p. 4.1 × 10-8 Pa at 20°C
Solubility In water: 0.095 g/l at 20°C; n-hexane: less than 1
g/l; dichloromethane: 100 - 200 g/l; 2-propanol: 10
– 100 g/l; toluene: 10 - 30 g/l; all at 20°C
Description The pure material is a colourless crystalline solid
Stability Stable for at least 18 months at 50°C
Formulations Water dispersible powders and emulsifiable
concentrates
Note Triadimenol is a mixture of the two diastereomeric
forms A (RS + SR; CA: 89482-17-7) and B (RR +
SS; CA: 88200-72-4); each of which is present as a
pair of enantiomers
224
TRIADIMENOL 398
TRIADIMENOL TECHNICAL
*
398/TC/M/-
1 Sampling. Take at least 100 g.
2 Identity tests
2.1 GLC. Use the GLC method below. The difference between the retention
times of triadimenol and the internal standard for the sample solution should not
deviate by more than 10 s from that for the calibration solution.
2.2 Infrared. Prepare potassium bromide discs from the sample and from a
corresponding standard using 1 mg of material and 300 mg potassium bromide.
Scan the discs from 4000 to 400 cm-1 (2.50 to 25 µm). The spectrum produced
from the sample disc should not differ significantly from that from the reference
standard.
3 Triadimenol
OUTLINE OF METHOD The sample is dissolved in, or extracted with toluene,

di-(2-ethylhexyl) phthalate is added as internal standard, and the content of
triadimenol is determined by capillary gas chromatography with on-column cold
injection.
REAGENTS
Toluene
Triadimenol standard of known purity, at least 950 g/kg
Di-(2-ethylhexyl) phthalate internal standard
Calibration solution. Prepare in duplicate calibration solutions. Weigh (to the
nearest 0.1 mg) about 200 mg of triadimenol (s mg) and 200 mg of di-(2-ethyl-
hexyl) phthalate (r mg) into a 20 ml volumetric flask, fill to the mark with
toluene and dissolve. Transfer with a pipette exactly 1.0 ml of the solution to a
100 ml volumetric flask, fill to the mark with toluene and homogenize.
APPARATUS
Gaschromatograph with flame ionization detector and on-column capillary

column accessory
Integrator Lab Data System, e.g. Hewlett Packard 3357 or equivalent
Column quartz capillary, 30 m × 0.53 (i.d.) mm, coated with silicone OV 1, 1 µm.
*
CIPAC method 1989. Prepared by the German Committee (DAPA). Chairman: Dr W Dobrat.
Based on a method supplied by Bayer AG (FRG)
225
TRIADIMENOL 398
PROCEDURE
(a) Preparation of sample solution. Weigh (to the nearest 0.1 mg) about 200 mg
of sample (w mg) into a 20 ml volumetric flask, add 200 mg of internal standard
di-(2-ethylhexyl)phthalate (q mg), fill to the mark with toluene and dissolve.
Transfer with a pipette exactly 1.0 ml of the solution to a 100 ml volumetric
flask, fill to the mark with toluene and homogenize. Prepare two solutions for
each sample.
(b) Operating conditions (typical):

Column temperature 2 min at 100°C, then 10°C/min up to 280°C
Injection port temperature cold on column injection
Detector temperature 280°C
Flow rate carrier gas helium: 5 ml/min
Flow rate make up gas nitrogen: 30 ml/min
Flow rate air and hydrogen as recommended by the manufacturer
Retention time triadimenol: about 18 min
di-(2-ethylhexyl) phthalate: about 23 min
(c) Determination. Inject at least two times 1 µl aliquots of each calibration

solution and calculate the single response factors fi using the formula below.
The individual values should agree within 2%, otherwise repeat the calibration.
If the response is satisfactory, inject 1 µl aliquots of each sample solution
bracketing them by injections of the calibration solutions as follows: calibration
solution 1, sample solution 1, sample solution 2, calibration solution 2. Measure
the relevant peak areas. Calculate the mean value f of each pair of response
factors bracketing two sample injections and use this value for evaluating the
two bracketed sample runs.
(d) Calculation
Ir  P  s
Response factor fi 
Hs  r
where:
fi = single response factors of triadimenol
Ir = peak area of the internal standard in the calibration solution i
P = purity of triadimenol (g/kg)
s = mass of triadimenol in the calibration solution i (mg)
Hs = peak area of triadimenol in the calibration solution i
r = mass of the internal standard in the calibration solution i (mg)
226
TRIADIMENOL 398
f  Hw  q
Triadimenol content  g/kg
Iq  w
where:
f = average response factor
Hw = peak area of triadimenol in the sample solution
q = mass of internal standard in the sample solution
Iq = peak area of internal standard in the sample solution (mg)
w = mass of sample taken (mg)
The content of triadimenol (sum of both diasteriomeric forms) is the mean value
of the results of the two solutions.
Repeatability r = 12.4 g/kg at 967 g/kg active ingredient content

Reproducibility R = 26.5 g/kg at 967 g/kg active ingredient content
TRIADIMENOL WATER DISPERSIBLE POWDERS

*
398/WP/M/-
1 Sampling. Take at least 500 g.
2 Identity tests
2.1 GLC. As for 398/TC/M/2.1.
2.2 Infrared
APPARATUS
Membrane-filter e.g. ACRO LC 25 from Gelman Sciences, Prod. no 4409
PROCEDURE Weigh an amount of the formulation containing about 50 mg of

active ingredient into a 10 ml flask and add tetrachloromethane. Warm up to
beginning boiling and let cool down for 1 min under shaking. Suck the
suspension into a 2 ml one-way-syringe and press it through a 0.45 µm
membrane filter into a 10 ml bottle. Fill a KBr cell with the clear red filtrate (w
= 0.1 mm) and scan the IR-spectrum. Verify the identity by comparing it with
the spectrum of triadimenol standard.
*
227
TRIADIMENOL 398
3 Triadimenol. As for 398/TC/M/3 except:
(a) Preparation of sample solutions. Weigh (to the nearest 0.1 mg) into a 20 ml
volumetric flask enough sample (w mg) to contain about 200 mg of pure
triadimenol, add 200 mg of internal standard (q mg). Fill to the mark with
toluene and dissolve. Transfer with a pipette exactly 1.0 ml of the solution to a
100 ml volumetric flask, fill to the mark with toluene, and homogenize. Let
material settle and inject 1 µl aliquots of the supernatant liquid. The
concentration of triadimenol should be similar to its concentration in the
calibration solutions. Prepare two solutions of each sample.

4 Suspensibility. (Draft method)
(a) Preparation of suspension MT 15.1 (i)

(b) Determination of sedimentation MT 15.1 (ii)
(c) Determination of triadimenol in the bottom 25 ml of suspension. After
removal of the top 225 ml of suspension add to the remaining 25 ml in the
cylinder 75 ml N,N-dimethylacetamid containing an amount of internal standard
that corresponds to the amount of active ingredient. Analyze according to
method 398/TC/M/3 using an injection port temperature of 160°C.
TRIADIMENOL EMULSIFIABLE CONCENTRATES

*
398/EC/M/-
1 Sampling. Take at least 500 ml.
2 Identity tests
2.1 GLC. As for 398/TC/M/2.1.

2.2 Infrared
APPARATUS
Disposable extraction column octadecyl type, 6 ml, J.T.Baker Art. no 7020-06,

or equivalent
*
228
TRIADIMENOL 398
PROCEDURE
Wash and activate the disposable extraction column with 10 ml

water/methanol 9 + 1. Put 0.5 ml of the sample containing about 100 mg of
active ingredient onto the humid column filling and let penetrate. Press
(within about 4 min) 20 ml water/methanol 9 + 1 slowly through the column
and remove the eluent. Then elute slowly with little pressure (within about 1
min) with 10 ml water/methanol 4 + 6 and collect the eluent. Dry with an air
stream on the water bath. Press the solid residue together with KBr to a disc
and scan the IR-spectrum. Verify the identity by comparing if with the
spectrum of triadimenol standard.
3 Triadimenol. As for 398/TC/M/3 except:
(a) Preparation of sample solutions. Thoroughly shake the sample container

to ensure that the emulsion is homogeneous. Immediately weigh (to the nearest
0.1 mg) enough sample (w mg) to contain about 200 mg of pure triadimenol
into a 20 ml volumetric flask, add 200 mg of internal standard (q mg), fill to
the mark with toluene and dissolve. Transfer with a pipette exactly 1.0 ml of
the solution to a 100 ml volumetric flask, fill to the mark with toluene, and
homogenize. Inject 1 µl aliquots of the supernatant liquid. The concentration
of triadimenol should be similar to its concentration in the calibration
solutions. Prepare two solutions of each sample.

229

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TRIADIMENOL 398

ISO common name Triadimenol

1 Sampling. Take at least 100 g.

OUTLINE OF METHOD The sample is dissolved in, or extracted with toluene,

Gaschromatograph with flame ionization detector and on-column capillary

(b) Operating conditions (typical):

(c) Determination. Inject at least two times 1 µl aliquots of each calibration

Repeatability r = 12.4 g/kg at 967 g/kg active ingredient content

TRIADIMENOL WATER DISPERSIBLE POWDERS

1 Sampling. Take at least 500 g.

Membrane-filter e.g. ACRO LC 25 from Gelman Sciences, Prod. no 4409

PROCEDURE Weigh an amount of the formulation containing about 50 mg of

3 Triadimenol. As for 398/TC/M/3 except:

Repeatability r = 3.29 g/kg at 148 g/kg active ingredient content

4 Suspensibility. (Draft method)

(a) Preparation of suspension MT 15.1 (i)

TRIADIMENOL EMULSIFIABLE CONCENTRATES

1 Sampling. Take at least 500 ml.

2.1 GLC. As for 398/TC/M/2.1.

Disposable extraction column octadecyl type, 6 ml, J.T.Baker Art. no 7020-06,

Wash and activate the disposable extraction column with 10 ml

3 Triadimenol. As for 398/TC/M/3 except:

(a) Preparation of sample solutions. Thoroughly shake the sample container

Repeatability r = 4.6 g/kg at 217 g/kg active ingredient content

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