Carbamates acaricides

Carbamates such as Aldicarb undergo degradation under both aerobic and anaerobic conditions. Indeed the oxidation of the sulfur moiety to the sulfoxide and sulfone is part of the activation of the compound to its most potent form. Subsequent aerobic metaboHsm can completely mineralize the compound, although this process is usually relatively slow so that it is an effective iasecticide, acaricide and nematocide. Anaerobically these compounds are hydrolyzed, and then mineralized by methanogens (61). 

Cinnamyl—sesamol ethers, eg (35), are useful as insect chemosterilants (111). 3,4-Methylenedioxyphenyl-3-halo-2-propynyl ethers (36, X = halogen) are synergists for carbamate insecticides (112). HaloaLkyl or haloalkenyl ethers, eg (37), show acaricidal and insect juvenile hormone activity (113). The first total synthesis of gibbereUic acid was from 2-methoxy-6-aLkoxyethyl-l,4-benzoquinone, a derivative of hydroxyhydroquinone (114). 

Paraquat Pesticides (includes acaricides, avicides, bactericides, insecticides, molluskicides, nematocides, piscicides, rodenticides) L S Chlorinated hydrocarbons (q.v.) Carbamates (q.v.) Organophosphorus compounds (q.v.) Herbicide... 

A wide range of insecticides (and acaricides and nematicides) show this mode of action. In the 11th Edn of Pesticide Manual there are 71 organophosphorus and 18 carbamate insecticides listed.5... 

Uses acaricide, citrus, fruit, vegetables Tradenames Carzol, Dicarzol (Schering) Type carbamate, amidine... 

AChE (carbamoylates — forms carbamoyl ester with active site Serine) [acaricide, most potent market carbamate insecticide, nematocide, toxic (atropine antidote)]... 

Caibamate pesticides are used as insecticide, acaricide, and herbicide. Various subclasses can be distinguished. Aryl V-methyl carbamates (1), such as caibaiyl, carbofuran, propoxur, and oxime V-methyl carbamates(2), such as aldicaib, methomyl, oxamyl, have most widely been studied. LC-MS is the method-of-choice for carbamates, since their thermal lability prohibits GC analysis. 

Synonyms 2,3-Dihydro-2,2-dimethyl-7-benzofur-anyl-N-methylcarbamate Brifur Crisfuran Curaterr Furadan Pillarfuran Yaltox FMC 10242 Bay 70143 Cbinufur Niagra NIA-10242 QMS 864 NIOSH/RTECS FB 9450000 NA 2757 STCC 4921525 Chemical/Pharmaceutical/Other Class N-Me-tbyl carbamate insecticide Acaricide Nematocide Chemical Structure ... 

Typically, insecticides represent about 30% of the market in agrochemicals. Activity depends on the ability to penetrate insects rapidly and reach sites of action in membranes of nerve cells. Insecticides are more soluble in fats than in water. The aryl amine insecticides include carbamic esters, such as pirimicarb (104), a diazine derivative (Scheme 23). It is of short-to-moderate persistence, but more selective than organophosphorus compounds. Acylation of A-methyl-l-naphthylamine, or reacting the chloroacetamido derivative with potassium fluoride in glycerol, affords the insecticide and acaricide known as nissol (105). 

Aldicarb is an insecticide, acaricide and nematocide with a very broad spectrum of action. At the same time, it shows the highest toxicity of all the known carbamate insecticides to warm-blooded animals. Its lDj, for rats is 0.93 mg/kg. 

A special example of the oxime carbamates is exo-3-chloro-endb-6-cyano-2-norbornanone-O-methylcarbamoyl oxime (UC 20047 A, Tranid , 53) (Kils-heimer and Manning, 1961 Payne et ai, 1965). It has a contact insecticidal and acaricidal action. It is also a strong poison for warm-blooded animals. 

The acaricidal activity of these formamidines is based on a mechanism which is entirely different from that of the chlorinated hydrocarbons, organophosphates and carbamates. Some of them are more toxic to organophosphate-resistant mites than to organophosphate susceptible ones (Dittrich, 1969). 

AT-(l-Acyl-l/f-2,l,4-benzothiadiazine-3-yl)carbamates (102) (see Section 6.15.6.1) and their 2-oxides are reported to have fungicidal and acaricidal activity <71GEP2108461>, whereas the 7-acyl (103 X = RCO) <72GEP2215733,75GEP2332486), 7-arylsulfonyloxy (103 X = ArSOjO) <77GEP2541742>, and 7-arylthio (103 X = ArS) <76GEP2438099> derivatives are notable anthelmintics. 

Insecticides accounted for 74% of the total agrochemical market value. Within this sector, organophosphates have 41% of the market by value, pyretliroids 20%, organochlorines 6% and carbamates 5%. Tlie remainder of the agrochemical market was represented by herbicides 14%, fungicides 9%, acaricides 2% and fumigants 1 %. 

Neurotoxic compounds have been traditionally the largest category of acaricides, with several representatives from the organophosphate, carbamate, and pyreth-roid classes. Several new pyrethroid compounds such as acrinathrin, lubrocythri-nate and halfenprox and an analog of the macrolide abamectin milbemectin were recently introduced as acaricides. A completely new acaricidal chemistry has been found with carbazate chemistry [1]. 

The carbamate and urea derivatives used as pesticides are commonly prepared with phosgene. The substituted ureas are mainly used as herbicides, while carbamates are used as insecticides and acaricides. It is estimated that 93% of all carbamates and 92% of all urea-based herbicides on the U.S. market are commercially synthesized with phosgene [206]. Of the substituted ureas, Monuron and Diuron are the most important pesticides in volume terms, and of the carbamates. Car-baryl (Sevin) is the single most important chemical. Eptam (S-ethyl-N,N-dipropyl... 

Carbofuran (1967) is a systemic heterocyclic carbamate which has a wide range of insecticidal, acaricidal and nematicidal activities. It is therefore active against a wide variety of soil and foliar pests. 

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