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Triforine

Publication Date: 9/95

TRADE OR OTHER NAMES

The active ingredient triforine is found in a variety of commercial fungicides. Some trade names for products containing triforine include Brolly, Denarin, Funginex, Nimrod T, Saprol, and Triforine DC (1, 2, 4, 8). Triforine is in mixed formulations with carbendazim, permethrin, mancozeb, and bupirimate (1).

REGULATORY STATUS

In the United States, triforine is marketed for use on almonds, apples, asparagus, blueberries, cherries, hops, ornamentals, peaches and roses. Triforine is a "restricted use" pesticide (RUP) with an EPA toxicity classification of I (highly toxic). Check with specific state regulations for local restrictions which may apply. Products containing triforine must bear the Signal Word "Danger" on their label (4, 5).

Outside the U. S. triforine is used on the previously mentioned commodities plus beans, cereals, cotton, cucurbits, grapes, hops, mangoes, mushrooms, sugar beets, tobacco and vegetables. It is also marketed on ornamentals in the home and garden market (5).

INTRODUCTION

Triforine is a piperazine derivative used as a systemic fungicide with protectant, eradicant and curative characteristics. It is used for control of powdery mildew, rusts, black rot and scab on cereals, fruit, ornamentals, and vegetables (1, 2, 4, 5). Triforine is also active against storage diseases of fruit and suppresses red spider mite activity (2). Because of it's low hazard to beneficial insects, triforine may be used in Integrated Pest Management (IPM) programs.

Triforine comes in emulsifiable concentrates, liquid seed treatments, and wettable powder formulations (1). Triforine is miscible with common insecticides and herbicides in the recommended manner of use (1).

TOXICOLOGICAL EFFECTS

ACUTE TOXICITY

Triforine and the formulated product Saprol have a low acute and dermal toxicity and have a moderate acute inhalation toxicity.

The acute oral LD50 for triforine in rats is greater than 16,000 mg/kg body weight. The acute percutaneous LD50 for rats is greater than 10,000 mg/kg. Acute dermal LD50 for rats is greater than 10,000 mg/kg body weight. The one hour acute inhalation LC50 for triforine in rats is greater than 4.5 mg/l air (1, 2, 3, 4, 5). This compound is rapidly absorbed and metabolized by the rat (6).

The acute oral LD50 for the formulated product Saprol in rats is 5,273 mg/kg body weight. The acute dermal LD50 for Saprol in rats is 4,186 mg/kg body weight. The acute inhalation LC50 for Saprol in rats is greater than 5,288 mg/m3. Saprol is considered an irritant to the skin (3).

The acute oral LD50 for triforine in mice is greater than 6,000 mg/kg; and greater than 2,000 mg/kg in dogs. The acute dermal LD50 for rabbits is greater than 10,000 mg/kg body weight (1, 2, 3, 4, 5).

CHRONIC TOXICITY

In two-year feeding studies, the No-effect-level (NEL) for triforine in dogs was 100 mg/kg diet and 625 mg/kg diet for rats (1, 2).

Reproductive Effects

A decreased number of fetuses and an increased number of resorptions were observed in a study of pregnant rats fed triforine at a dietary level of 1,600 mg/kg (6). The formulated product Saprol does not affect reproduction and development (3).

In another developmental study, rabbits were fed doses of 0, 5, 25 and 125 mg/kg/day of triforine. The maternal No-observable-effect-level (NOEL) was 5 mg/kg/day; the maternal Lowest-effect-level (LEL ) was 25 mg/kg/day, rabbits exhibited reduced food intake and loss of body weight. The fetotoxic NOEL was 5 mg/kg/day; the fetotoxic LEL was 25 mg/kg/day, decreased average relative weight was observed (7).

Teratogenic Effects

In a developmental study, rabbits were fed doses of 0, 5, 25 and 125 mg/kg/day of triforine. The teratogenic NOEL was greater than 125 mg/kg/day (7). The formulated product Saprol is not considered a teratogen (3).

Mutagenic Effects

The formulated product Saprol is not considered a mutagen (3).

Carcinogenic Effects

In short and long-term studies of the formulated product Saprol, no irreversible or carcinogenic effects were observed (3).

Organ Toxicity

High dosages in subchronic animal studies demonstrated adverse effects on red blood cells and deposition of iron in several organs (6). If triforine is ingested, the main hazard is aspiration of the solvent carrier into the lungs resulting in chemical pneumonitis (3).

Fate in Humans and Animals

In a metabolism study of triforine fed to rats, 94% was excreted after 48 hours and 96% was excreted after 168 hours; 18% by fecal excretion and 78% by renal excretion. Two metabolites were found in urine, one of which was chloralformamide (7).

ECOLOGICAL EFFECTS

Effects on Birds

The acute oral LD50 for triforine in bobwhite quail is greater than 5,000 mg/kg (2, 8). The formulated product Saprol is practically non-toxic to birds by acute oral exposure and only slightly toxic by dietary exposure. The acute oral LD50 for Saprol in bobwhite quail is greater than 5,000 mg/kg. The dietary LC50 for bobwhite quail is 1,850 ppm in the diet. Mallard ducks had a dietary LC50 of greater than 4,640 ppm in the diet (3).

Effects on Aquatic Organisms

At 50 mg/l in water, there are no signs of poisoning in Lebistes reticulatus. Rainbow trout and bluegill sunfish tolerate 1,000 mg/l in water for 96 hours without symptoms (1, 8). The 96- hour LC50 for rainbow trout and bluegill sunfish is greater than 1,000 mg/l (2).

The formulated product Saprol is of low hazard to fish and aquatic invertebrates. Both rainbow trout and bluegill sunfish had a 96-hour LC50 of greater than 500 mg/l. The aquatic invertebrate Daphnia (water flea) had a 48-hour EC50 of greater than 25 mg/l (3).

Saprol was also noted to be of low hazard to Scenedesmus subspicatus (aquatic algae). The 96-hour EC50 was greater than 380 mg/l (3).

Effects on Other Animals (Nontarget species)

No toxic effect was observed in honeybees at less than or equal to 1,000 mg/kg diet (2). Triforine and the formulated product Saprol are considered of low hazard to honeybees and to the predatory mite Typhlodromus pyrii. It is also of low hazard to earthworms at recommended dose rates (1, 3, 4).

ENVIRONMENTAL FATE

Breakdown of Chemical in Soil and Groundwater

The half-life of triforine in soil is approximately 3 weeks. A range of non-fungitoxic metabolic end-products are formed, presumably including piperazine. It is considered non-persistent in soil (1, 2, 5).

Breakdown of Chemical in Surface Water

No information currently available.

Breakdown of Chemical in Vegetation

Triforine is translocated in plants upward through the root system. Triforine is phytotoxic to some varieties of pears (5).

PHYSICAL PROPERTIES AND GUIDELINES

Triforine decomposes when it comes in contact with concentrated sulfuric acid, hydrochloric acid, or alkali. Thermal decomposition may release toxic and/or hazardous gases (6).

Physical Properties:

CAS No.: 26644-46-2
Chemical name: 1,4-bis(2,2,2-trichloro-1-formamidoethyl)piperazine; 1,1'-piperazine-1,4-diyldi-[N-(2,2,2-trichloroethyl)formamide];
N,N'-[1,4-piperazinediylbis(2,2,2-trichloro-ethylidene)]bisformamide (1, 2)
Chemical Class/Use: Systemic fungicide (1)
Solubility in water: at room temperature, ca. 30 mg/l (1); 6 mg/l water (2)
Solubility in other solvents: Readily soluble in dimethylformamide, dimethyl sulphoxide and N-methyl-pyrrolidone;
soluble in tetrahydro-furan; slightly soluble in cyclo-hexanone and dioxane;
practically insoluble in benzene, methylene chloride, petroleum ether and cyclohexane (1, 2, 6)
Melting point: ca. 155 degrees C (with decomposition) (1, 2, 3); 311 degrees F (6)
Vapor pressure: 2.6 x 10 to the minus 7 mbar at 25 degrees C (1, 3); 26 uPa at 25 degrees C (3); 0.0000002 mmHg at 25 degrees C (6)

BASIC MANUFACTURER

American Cyanamid Company
Agricultural Research Division
P. O. Box 400
Princeton, NJ 08543-0400
Telephone: 609-799-0400

Review by Basic Manufacturer:

Comments solicited: October, 1994
Comments received:

REFERENCES

  1. The Agrochemicals Handbook. 1983. The Royal Society of Chemistry, The University, Nottingham, England.
  2. Worthing, C. R. (ed.) 1983. The Pesticide Manual: A World Compendium. Seventh edition. Published by The British Crop Protection Council.
  3. The Saprol Fungicide Fact File. Shell Agrichemicals.
  4. Farm Chemicals Handbook. 1994. Meister Publishing Co. Willoughby, OH.
  5. Thomson, W. T. Agricultural Chemicals. Book IV: Fungicides. 1990. Thomson Publications, Fresno, CA.
  6. OHS Database. Occupational Health Services, Inc. 1994. MSDS for Triforine. OHS Inc., Secaucus, NJ.
  7. U.S. Environmental Protection Agency. 1993. Office of Pesticides. TOX Oneliners -- Triforine. April, 1993.
  8. Pesticide Management and Education. An on-line pesticide information database in CENET, Cornell Cooperative Extension Network. Cornell University, Ithaca, NY.