Bendiocarb

Bendiocarb (Ficam, Garvox, Seedox, Dycarb, Multamat) 

IUPAC name 2,3-isopropylidenedioxyphenyl methylcarbamate Molecular formula C11H13NO4 Toxicity class USEPA II WHO II 

Uses Bendiocarb is an odorless, white crystalline solid. It is stable under normal temperatures and pressures, but should not be mixed with alkaline preparations. Thermal decomposition products may include toxic oxides of nitrogen. It is noncorrosive. Formulations of bendiocarb are classified as general use pesticides (GUP), with the exception of Turcam and Turcam 2.5 G, which are classified as restricted use pesticides (RUP). In view of this, the chemical should be purchased and used only by certified and trained applicators. 

Toxicity Bendiocarb is moderately toxic if it is ingested or absorbed through the skin. Skin absorption is the most likely route of exposure. It is a mild irritant to the skin and eyes.4 Like other carbamate insecticides, bendiocarb is a reversible inhibitor of cholinesterase, an essential nervous system enzyme. Symptoms of bendiocarb poisoning include weakness, blurred vision, headache, nausea, abdominal cramps, chest discomfort, constriction of pupils, sweating, muscle tremors, and decreased pulse. 

Bendiocarb is absorbed through all the normal routes of exposure (oral, dermal, and inhalation), but dermal absorption is especially rapid. Carbamates generally are excreted rapidly and do not accumulate in mammalian tissue. If exposure does not continue, cholinesterase inhibition and its symptoms reverse rapidly. In nonfatal cases, the illness generally lasts less than 24 hours.7 Bendiocarb is moderately toxic to birds. The LD50 in mallard ducks is 3.1 mg/kg, and in quail is 19 mg/kg.8 Bendiocarb is moderately to highly toxic to fish. The LC50 (96 hours) for bendiocarb in rainbow trout is 1.55 mg/L.2 

Synonyms 2,2-dimethyl-1,3 -benzdioxol-4-yl-A-methylcarbamate methylcarbamic acid 2,3 -(isopropylidenedioxy)phenyl 

Colorless crystals mp 130°C (266°F) density 1.25 at 20°C (68°F) slightly soluble in water, 40 mg/L at 20°C (68°F) readily soluble in acetone, methylene chloride, ethanol and benzene poor solubility in hexane [280 mg/L at 20°C (68°F)] octanol-water partition coefficient 50. 

LDso oral (rat) 40 mg/kg LDso oral (rabbit) 35 mg/kg LDso skin (rat) 600 mg/kg 

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Anthrahydroquinones have been patented in Japan as bird repeUents (73), and anthraquinone [84-65-1] (qv) is used widely in Europe as a spray to protect growing crops and as a wood dressing. The synthetic pyrethroid deltamethrin [52918-63-5] (27) was evaluated (74), as were other materials, including bendiocarb (20) (75) and 20,25-dia2ocholesterol dihydrochloride [1249-84-9] (Omitrol) (28), a steroid that inhibits embryo development when adsorbed or ingested as a seed treatment of bait com (55,76). 

White, P.F. 1986. Effects of bendiocarb and diflubenzuron on mushroom cropping. Am. Appl. Biol. 108 11-20. 

IV-Isopropyl-3-hydroxyoxindole, see Propachlor 2,3-Isopropylidenedioxyphenol, see Bendiocarb Ispropylisocyanate, see Iprodione 2 Isopropyl-4-methyl-6-hydroxypyrimidine, see Diazinon... 

Irradiation of isoprocarb and promecarb resulted in PFR to ortho- andpara-hydroxybenzamides. The photodegradation of analogous carbamate pesticides (bendiocarb, bendiocarb, ethiofencarb,furathiocarb,fenoxycarb, and pirimicarb) has also been examined, but in these cases, the most general result was formation of the corresponding phenols [298]. 

Carbofuran (90) is the most widely used heterocyclic carbamate, with applications as a soil and systemic insecticide. It is made (65NEP6500340) via a Claisen rearrangement of l-methylallyloxy-2-nitrobenzene (Scheme 14). Replacement of the carbon in the 3-position by oxygen gives 2,2-dimethylbenzo-l,3-dioxol-4-yl methylcarbamate, known as bendiocarb (68SAP6800736), which has also achieved some success. Dimethylcarbamates are usually preferred for heterocyclic insecticides, since the methylcarbamates are often very unstable. 

Fig. 3 HPLC chromatogram of spiked apple extract. Peaks (1) folpet, (2) dimehoate and benomyl, (3) aldicarb, (4) bendiocarb and pirimicarb, (5) carbaryl, (6) tolylfluanid and thiram, (7) propham, (8) cap-tan and azinphos methyl, (9) chlorpropham, (10) iprodione, (11) procymidone, (12) vinclozolyne, (13) parathyon ethyl, (14) endosulfan sulfate, (15) toclophos methyl and chlorpyriphos methyl, (16) dico-fol, (17) /3-endosulfan, (18) tetradifon, (19) a-endosulfan, (20) chlorpyriphos and dieldrin, (21) />,p -DDT, (22) p,p -DDT. 0.1 AUF concentrations 10-20 ng/20/tl injected volume 20pi. (From Ref. 57.)...

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