Green Chemistry and the Ten Commandments

P O NO 2

H 3 CO S

H 3 CO

Methyl  parathion

Carbamic    acid

H

N

H

C

O

OH

N

N

C

C C

CH 3

H

H H

H

H

H

Nicotine

Organochlorine compounds

Organophosphates

Carbamates

Carbofuran

C

O

CH 3

H 3 C

O C

O

N

H

CH 3

H

H

Insecticides from plants

C

OC

H 3 CO

C

C

O

O

O

OCH 3

H H

C

H CC H 3

H

H

H

H

H

Rotenone

DDT

C

Cl C Cl

Cl

Cl

H

Cl

C C

C

Cl

Cl

Cl

Cl

C

C

C

H

H

H

H

H

Cl

Cl

ClCCl

Chlordane

H 3 C

O C 2 H 5

S C

O

S

O P H

C C

CH 3 O

C O C 2 H 5

H

H O

Malathion

Hydrolizable bonds

Carbaryl

C

O

N

H

O CH 3

H 3 C

H H

CO

HC

H

C C

C

C C

H

H

H HH

C

H 3 C

C CCC

CH 3

H CH^3

C

H

OCO C

H 3 C

H

C H

H

Pyrethrin   I

Figure 7.7. Some examples of insecticides that are, or have been, potential water pollutants.

Carbamates, in which various hydrocarbon groups are substituted for H on
carbamic acid, largely replaced phosphates, and several carbamates are still widely used.
Carbaryl (Sevin) is used to kill insects on lawns or gardens and, because of its low
toxicity to mammals, can be sprinkled on pets in (usually futile) attempts to rid them of
flea infestations. Highly water-soluble carbofuran is a plant systemic insecticide that is
taken up by roots and leaves and distributed through the plants, killing insects that feed
on the plants. Like organophosphates, carbamates are acetylcholinesterase inhibitors,
but are not highly toxic to animals other than insects. They are very biodegradable and
are not generally serious water pollutants.

Chap. 7. Water, The Ultimate Green Solvent 181