pages from encyclopedia of agrochemicals v3
TRANSCRIPT
Table 1. Variation in Phosphorus Ester Types of Organophosphorus Insecticides
Structure Type Organophosphorus Insecticides
R1O
P
OR3R2O
O Phosphate Chlorfenvinphos, dichlorvos, dicrotophos, dimethylvinphos, hetenophos,mevinphos, monocrotophos, naled, phosphamidon, propaphos,tetrachlorvinphos
R1O
P
OR3R2O
S O−R1 O−R2 O−R3
Phosphorothioate∗1Phosphorothionate∗2
Chlorethoxyphos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,diazinon, ethrimfos, famphur, fenitrothion, fenthion, flupyrazofos, isazofos,isoxathion, methacrifos, parathion, parathion-methyl, phoxim,pirimiphos-ethyl, pirimiphos-methyl, pyridaphenthion, quinalphos, sulfotep,tebupirimfos, temephos, triazophos
R1O
P
SR3R2O
O O−R1 O−R2 S−R3
Phosphorothioate∗1Phosphorothiolate∗2
Azamethiphos, demeton-S-methyl, omethoate, oxydemeton-methyl, profenofos,pyraclofos, vamidothion
R1O
P
SR3R2O
S O−R1 O−R2 S−R3
Phosphorodithioate∗1Phosphorothiolothionate∗2
Azinphos-ethyl, azinphos-methyl, chlormephos, dimethoate, disulfoton, ethion,formothion, malathion, mecarbam, methidathion, phenthoate, phorate,phosalone, phosmet, prothiofos, sulprofos, terbufos, thiometon
R1O
P
SR3R2S
O O−R1 S−R2 S−R3
Phosphorodithioate∗1Phosphorodithiolate∗2
Cadusafos, ethoprophos
R1O
P
NR2O
O Phosphoramidate Phenamiphos
R1O
P
NR2O
S O−R1 O−R2
Phosphoramidothioate∗1Phosphoramidothionate∗2
Isofenphos, propetamphos
R1O
P
NR2S
O O−R1 S−R2
Phosphoramidothioate∗1Phosphoramidothiolate∗2
Acephate, fosthiazate, methamidophos
R1O
P
CR2O
O Phosphonate Trichlorfon
R1O
P
CR2O
S O−R1 O−R2
Phosphonothioate∗1Phosphonothionate∗2
EPN
R1O
P
CR2S
S O−R1 S−R2
Phosphonodithioate∗1Phosphonothiolothionate∗2
Fonofos
∗1 ‘‘Thioate’’ does not distinguish between thionate (P=S) and thiolate (P−S−);∗2However, the terms ‘‘thionate,’’ ‘‘thiolate,’’ and ‘‘thiolothionate’’ for the groupings P(S)OR, P(O)SR, and P(S)SR are superseded by the O−R S−Rphosphorothioate and phosphorodithioate terminology.
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