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GREEN CROSS

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Triforine

ClyC.CH.NH.CHO

i
C150. CH.NH.CHO

T6N DNTJ AYMVHXGGG DYMVHXGGG CroHsClN,O, (435-0)

Nomenclature and development. The common name triforine is approved by BSI, ISO and
ANSI. The IUPAC name is 1,4-bis(2,2,2-trichloro-|-formamidoethyl)piperazine
previously known as 1,1'-piperazine- 1,4-diyldi-[V-(2,2,2-trichloroethyl)formamide],
in Cia. usage N.N'-(1,4-piperazinediylbis(2,2,2-trichioroethylidene)|bisformamide
[26644-46-2]. This compound, first synthesised by C.H. Boehringer Sohn in 1967
(DOS 1901421), was introduced in 1969 by Cela GmbH under the code number
‘Cela W524", Its fungicidal properties were described by P. Schicke & K.H. Veen, Proc.

r. Insectic, Fungic. Conf., 5th, 1969, 2, 569.

Manufacture and properties, Produced by the reaction of piperazine with N-~(1.2,2,2-
tetrachloroethyl)formamide, it forms colourless crystals, m.p. 155°, v.p.2x 10-7 inmHg
at 25°. Its solubility at room temperature is 27-29 ma2/l water; it is of low solubility in
acetone, benzene, carbon tetrachloride, chloroform, dichloromethane, light petroleum;
slightly soluble in dioxane or cyclohexanone; soluble in tetrahydrofuran; readily soluble
in dimethylformamide, dimethyl sulphoxide or |-methyl-2-pyrrolidone.

It is rapidly decomposed to trichloroacetaldehyde and piperazine salts by
concentrated H,SO, or HCl; slowly decomposed to chloroform and piperazine by strong
alkalies. It is non-persistent in soil. The pathways of its photochemical and metabolic
breakdown have been established: H. Buchenauer, Pestic. Sci, 1975, 6, $3: A. Fuchs et
al., ibid., 1976, 7, 115, 127; S. Darda eral., ibid., 1977, 8, 183; S. Darda, idid., 9.173;
J.P. Rouchard er al., ibid, p.65, 1978, 9, 74, 139, 587; J.P. Rouchard, Buil. Environ.
Contam. Toxicol., 1977, 18, 184.

Uses. Triforine is a systemic fungicide effective against: powdery mildew, scab and other
diseases of fruit and berries at 20-25 g/1001; powdery mildew, rust and black spot on
ornamentals at 15 2/100!; powdery inildew and other diseases cf vegetables at 25 g/1001:
powdery mildew and other leaf diseases on cereals at 200-250 g/ha, rust on cereals at
300 e/ha. [t is active against storage diseases of fruit and suppresses red spider mite
activity.

Toxicology. The acute oral LD 50 for rats, mice and quail is > 6000 mg/kg, it is non-tozic
to guppies at 50 me]; non-toxic to honey bees,

Formulation. ‘Saprol’, ¢.c. (200 g a.ivl); ‘Nimrod T, e.c, (62-5 g bupirimate + 62:5 g triforine/l);
‘Funginex’,
Analysis. Product and residue analysis is by polarography or GLC (a‘ter degradation);

particulars from Celamerck. Ses also R, Darskus & D. Eichler, daal. Methods Pestic.
Plant Growth Regul., 1978, 10, 243.

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