932
T3D0928
Benomyl
Benomyl (also marketed as Benlate) is a fungicide introduced in 1968 by DuPont. It is a systemic benzimidazole fungicide that is selectively toxic to microorganisms and invertebrates, especially earthworms. Benomyl binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation. The selective toxicity of benomyl as a fungicide is possibly due to its heightened effect on fungal rather than mammalian microtubules. Due to the development and worldwide prevalence of resistance of parasitic fungi to benomyl, it and similar pesticide compounds became largely ineffective.
17804-35-2
28780
C14H18N4O3
290.137890
White powder.
140°C
0.0038 mg/mL at 20°C
Inhalation (L793) ; oral (L793); dermal (L793)
Benomyl targets beta tubulin in actively dividing cells. It binds to microtubules, interfering with cell functions, such as meiosis and intracellular transportation (A15332). Benomyl binds to brain tubulin with a dissociation constant of 11.9 +/- 1.2 microM. Further, benomyl binds to a novel tubulin beta binding site, distinct from the well-characterized colchicine and vinblastine binding sites. Benomyl inhibits the polymerization of brain tubulin into microtubules, with 50% inhibition occurring at a concentration of 70-75 microM (A15103)
Benomyl is of such a low toxicity to mammals, it has been impossible to administer doses large enough to establish an LD50. It has an arbitrary LD50 of "greater than 10,000 mg/kg/day for rats".
No indication of carcinogenicity to humans (not listed by IARC).
It is a systemic fungicide that is selectively toxic to microorganisms and invertebrates. It is also employed as a casting worm control agent in amenity turf situations such as golf greens and tennis courts. It is also used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, pineapples, and pomes.
The Occupational Safety and Health Administration has set a permissible exposure limit of 15 mg/m3 for total exposure over an eight-hour time-weighted average.
Skin irritation may occur through industrial exposure, and florists, mushroom pickers and floriculturists have reported allergic reactions to benomyl. Benomyl is a potential teratogen. Studies have shown eye defects can occur at relatively high doses. A test in which rats were dosed orally demonstrated evidence of microphthalmia at dose levels of 62.5 mg/kg and above. In 1996, a Miami jury awarded US$ 4 million to a child whose mother was exposed in pregnancy to Benomyl. The child was born without eyes. The mother had been exposed to an unusually high dose of Benomyl through her occupation, during pregnancy.
Skin redness and skin irritation. Fetuses exposed to high levels may exhibit microphthalmia (small eyes) or anaphthalmia (no eyes).
For acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
2009-06-17T23:53:01Z
2014-12-24T20:22:57Z
C10896
3015
D001542
Benomyl
5798
true
CCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12
C14H18N4O3
InChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)
InChIKey=RIOXQFHNBCKOKP-UHFFFAOYSA-N
290.3177
290.137890462
Exogenous
Solid
2.12
HMDB31767
CHEMBL327919
26771