Drugs & pesticides by dr. pramod r. padole

By
Dr. P. R. Padole
Department of Chemistry
Shri Shivaji Science College, Amravati.

Contents of Unit-IV:
Dyes:1
Drugs:2
Pesticides:3
Unit Test4

Drugs:
Q.1) What is drug? (W-13, 1-2 Mark)
Q.2) What are drugs? (W-14, 1-2 Mark)
Q.3) What are drugs? What requirements should ideal drug satisfy.
The term ‘drug’ is derived from a French word: ‘drogue’ – a dry herb.
Defination:
According to World Health Organisation (WHO, in 1966),
“Drug is any substance or product that is used to
prevent or cure diseases in human beings or animals”.
OR
“Drug is defined as “any substance or product that is
used to modify or explore physiological systems or
pathological states for the benefit of recipient.”
OR
Drugs are also defined as, “synthetic or
natural substances or product which are used to
relieve discomfort and restore a state of well being.”

A drug is any substance
that, alters normal
bodily function,
resulting any
psychological or
behavioral change.
OR
 Drug is a substance
used to treat an illness.
Drugs:

pramodpadole@gmail.com Dr P. R. Padole
Requirements for An ideal drug :
First Second Third Fourth
Action
should be
localized
at the site
where
it is
desired to
act
Act on a
system
with
efficiency
and
safety
Not be
toxic
Minimum
side
effects

LOGO
pramodpadole@gmail.com
ANALGESICS
&
ANTIPYRETICS:

LOGO
ANTIPYRETICS:
Q.1) What are antipyretic drugs? (S-11, W-11, W-14 & W-17, 1-2 Mark)
Q.2) What are analgesics & antipyretics?
Q.3) Substances which reduce body temperature in high fever are called antipyretic.
ANTIPYRETICS:
Defination:
The substances which reduce body
temperature in high fever are called as antipyretics.
Antipyretics are also analgesics.

LOGO
ANALGESICS:
ANALGESICS:
 The substances (compounds) which
relieves pain are called analgesic.
Or
 The compounds which reduce the pain are
called as analgesic.
Q.1) What are analgesic drugs? (W-11, 1-2 Mark)
Q.2) The compounds which relieve the pain are called as analgesic.
Q.3) Narcotics are the substances which produce sleep and unconsciousness.
Q.4) The compounds which reduce the pain are called as __________. (W-15, ½ Mark)

Types of ANALGESICS:
Narcotics:
are chemical
substances which
produce sleep
and
unconsciousness.
ANALGESICS:
Pain Relief
Non-
norcotics:
do not cause
addiction
e.g.
Phenylbutazone

My student still waiting about Non-norcotics:
Non-norcotics:
do not cause addiction.
The most important non-norcotic
analgesic is Phenylbutazone
(Butazolidine)
Bali
Amravati

B.Sc.-II (Sem-IV) Unit No. – III
B) REACTIVE METHYLENE COMPOUNDS:
CH3 C CH2 C OC2H5
O O
CH2 C OC2H5
O
Ethylaceto acetate or
Acetoacetic ester (AAE)
Diethylmalonate or
Malonic ester
C2H5O C
O
Active
Methylene Groups
EWGEWG
Acetyl gp Ester gp
EWG
( - Hydrogens)
When methylene group (-CH2-) is present between two strongly electron
withdrawing groups (EWG) such as -COCH3, -COOC2H5 or -CN; then
hydrogens of methylene group are acidic and reactive, called as reactive
methylene group.
Compound containing reactive methylene group is called as reactive methylene compound.

Phenylbutazone (Butazolidine)
 Preparation or Synthesis of Phenyl-butazone (Butazolidine):
Q.1) Give synthesis and uses of Phenylbutazone. (S-16, W-16 & S-18, 4 Mark)
Q.2) What kind of Phenylbutazone drug is?
Q.3) Phenylbutazone is a non-norcotic type of analgesic.
Q.4) Phenylbutazone is___________
a) Antimalarial b) Sulpha drug c) Antipyretic d) Non-norcotic analgesic
Q.5) Describe synthesis and uses of Phenylbutazone. (S-19, 4 Mark)
HC
C OC2H5
O
C
O
OC2H5
Diethyl Malonate
C2H5ONa
C4H9 Br CH
C OC2H5
O
C
O
OC2H5
C4H9
Diethyl butyl Malonate
N-HC6H5
N-HC6H5
Diphenyl hydrazine
C6H5 N
N
C
O
C6H5
C
O
C
H
C4H9
Phenyl butazone
(Butazolidine)
H+ + HBr
n-butyl bromide
C
CC2H5O
O
C
O
C2H5O
C4H9
Diethyl butyl Malonate
+ + 2 C2H5OH
Step-1) Preparation of Diethyl butyl malonate from Diethyl malonate & n-butyl bromide
Step-2) Preparation of Phenyl butazone from Diethyl butyl malonate & Diphenyl hydrazine
H

Uses of Phenylbutazone :
Uses
of
Phenylbutazone
More than one week because it is toxic
Therapy of acute attack of gout
Treatment of spondylites
with aspirin is used as a strong medicine
to cure rheumatoid arthritis (Joints deformities)
Mild analgesic & antipyretic
Toe & foot caused by defects in Uric acid metabolism

By Dr. P. R. Padole
SULPHA DRUGS:
SULPHA DRUGS:
‘Sulfa drugs’ were some of the original antibiotics,
and are still in use today.
These are substituted sulphanilamides.
These contain sulphonamide (─SO2NH2)
group in their structure.
These were used to cure bacterial infections in
human beings.
Q.1) What are sulpha drugs? (W-11, W-12, W-13, S-17 & W-18, 1-2 Mark)
Q.2) What are sulpha drugs? Which structural unit these contain?

SULPHA DRUGS:
 They have played an important role in curing diseases like
pneumonia, dysentery, etc.
 They may be prescribed to treat urinary tract infections
(UTIs), bronchitis, eye infections, bacterial meningitis, pneumonia,
ear infections, severe burns, traveler's diarrhea, and other conditions.

Types of SULPHA DRUGS:
1. Sulphanilamide
2. Sulphaguanidine
3. Sulphapyridine
4. Sulphathiazole
5. Sulphadiazine

LOGO
Do you know?
Sulphanilamide

LOGO
Sulphanilamide:
 Preparation or Synthesis of Sulphanilamide:
Q.1) Give the preparation and uses of Sulphanilamide.
(W-09, W-11, S-12, W-13, S-15 & W-18, 4 Mark)
Q.2) Sulphanilamide is _____________.
a) Antibacterial b) Antimalarial c) Analgesic d) Antipyretic
Q.3) How sulphanilamide is prepared? (S-17, 4 Mark)
Uses:
Sulphanilamide has antibacterial power and is used in medicine against
“cocci – infections” such as streptococci, gonococci and pneumococci.
It is cheapest sulpha drug.
N
Acetanilide
H
C
O
CH3 N
N4 - Acetyl sulphanilyl
chloride
H
C
SO2-Cl
O
CH3 N
N4 - Acetyl sulphanilyl
amide
H
C
SO2NH2
CH3
H+
/ HOH
N
Sulphanilamide
H
H
SO2NH2
Cl SO3H
Chlorosulphonic acid
Chlorosulphonation + NH3
O
Acid Hydrolysis
H HO-SO2-Cl
- H2O
H-NH2
- HCl
1
2
3
4
H OH
+ CH3COOH
Sulphanilamide (p- amino benzene sulphonamide)

Sulphadiazine:
Q.1) Give the preparation and uses of Sulphadiazine. (W-15, S-17 & S-18, 4 Mark)
Q.2) For what purpose the sulphadiazine drug is used?
Q.3) Sulphadiazine can be synthesized by oxidation of 2-aminopyrimidine with p- acetylsulphanilyl chloride
followed by alkaline hydrolysis.
Q.4) Sulphadiazine is synthesized from___________.
a) Acetanillide b) Quinoline c) Dithiocarbamate d) Anthranilic acid
Q.5) Sulphadiazine is synthesized from___________. (S-17, ½ Mark)
a) Acetanillide b) Quinoline c) Sulphanilamide d) Acetone
Q.6) How the drug sulphadiazine is prepared? Give its uses. (W-17, 4 Mark)
Sulphanilamide
(p- amino benzene sulphonamide):
Sulphadiazine:
H2N SO2NH
N
N
Sulphadiazine
Pyrimidine

Preparation of Sulphadiazine:
Uses:
1) Sulphadiazine is eight times active than sulphanilamide and is used for the
cure of bacterial infections.
2) It is much less toxic, absorbed slowly by intestinal tract and also excreted slowly.
H3C C
O
NH
Cl-SO3H
-HOH
H3C C
O
NH SO2-Cl
Acetanilide N4-acetyl sulphanilyl chloride
N
N
H-HN
2-amino pyrimidine
Pyridine
H3C C
O
H
N SO2 NH
N
N
aq. NaOH
H2N SO2-NH
N
N
Sulphadiazine
H + HO-SO2-Cl
or
Chlorosulphonic acid
+
Condensation
-HCl
HO H
Alkaline hydrolysis
+ CH3COOH

Digestive SystemCB/V/1718 of 1031
Uses of Sulphadiazine:
Mouth
Anus
Oesophagus
Pharynx (throat)
Stomach
Small
Intestine
Large
Intestine
Alimentary
Canal
or
Digestive
Tract
It is much less toxic, absorbed slowly by intestinal tract and also excreted slowly.
H2N SO2NH
N
N
Sulphadiazine

www.themegallery.com
ANTIMALARIALS:
Antimalarials are chemical substances
used to lower down malarial fever.
Examples: Chloroquine, quinine,plasmochin etc.
Q.1) What are antimalarial drugs? (W-18, 1 Mark)
Q.2) What are antimalarials?
Q.3) What are antimalarials? Give synthesis of Chloroquine from 4,7- dichloroquinoline? Give
uses of chloroquine.
Q.4) How chloroquine is useful as an antimalarial?
Q.5) What are the two reactants which on condensation give chloroquine drug?
Q.6) The chemical substances used to lower down malarial fever are called antimalarial.
Q.7) Chloroquine is a drug which is active against all species of plasmodia.
Q.8) 4,7-dichloroquinoline is used in the synthesis of Chloroquine drug.
Q.9) 4,7-Dichloroquinoline is used for the synthesis of ______________
a) Phenylbutazone b) Sulphadiazine c) Chloroquine d) Sulphanilamide
Q.10) Chloroquine is used for the following treatment _____________.
a) To reduce malarial fever . b) To relieve Pain c)To kill Plasmodium species d) To produce sleep
Q.11) Give the synthesis of Chloroquine from 4,7- dichloroquinoline. (S-16 & W-17, 4 Mark)
Q.12) How the drug chloroquine is synthesized ? Give its uses. (W-16, 4 Mark)
a) Acetanillide b) Quinoline c) Sulphanilamide d) Acetone
Q.13) What are antimalarial drugs? Give synthesis of Chloroquine. (W-18, 4 Mark)
Q.14) Write synthesis and uses of Chloroquine. (S-19, 4 Mark)

Preparation of Chloroquine:
Step-1) Preparation of 4,7-dichloroquinoline:
NH-HCl
3-Chloro aniline
C2H5
O
C
C
O
C
HO
Ethyl ester of
formyl acetic acid
Cl
N
CH
CH
C
O
O
C2H5
Enamine
250 0
C
NCl
O H
7-Chloro-4-hydroxy
Quinoline
- POCl3
NCl
Cl
4,7-Dichloro Quinoline
1
2
3
H
H - H2O
H
H
(1) - C2H5OH
PCl3-ClCl
+ PCl5
- HCl1
2
3
4
5
6
7
(2) Aromatization
CH3 C CH2 C OC2H5
O O
Ethylaceto acetate or
Acetoacetic ester (AAE)
EWG
Acetyl gp
EWG

 Step-2) Preparation of 4-diethylamino-1-methylbutylamine
from AAE:
O
C
C
C
C2H5 O
O
CH3
Acetoacetic ester
(AAE)
Cl CH2 CH2 N
C2H5
C2H5
N,N-diethyl-2-chloro ethane
Na
O CH
C
C2H5 - O
O
CH3
C
C
N
C2H5
C2H5
2-Diethyl amino ethyl acetoacitic ester
i) Hydrolysis by
O
C
C
CH3
C
C
N
C2H5
C2H5
1-Diethyl amino-4-pentanone
H2N
CH
C
H2
CH3
H2
C
C
H2
N
C2H5
C2H5
4-Diethyl amino-1-methyl buthyl amine
-CO2
H
H 12 - HCl
H2
H2
HCl
ii) Decarboxylation
HO-H
(- C2H5OH)
H2
H2
H2
i) Reduction by Raney Ni
(- H2O)
(i.e., >C=O >CH2)
ii) Reaction with NH3
(i.e., >CH-H >CH-NH2)1
2
3
4
(Note that: AAE
CH3-C-CH2-C-OC2H5)
O O

 Step-1) Preparation of 4,7-dichloroquinoline:
 Step-2) Preparation of 4-diethylamino-1-methylbutylamine from AAE:
 Step-3) Condensation of these two
compounds; to form Chloroquine as a product:
Step-1 Step-2
HN
CH
C
H2
CH3
H2
C
C
H2
N
C2H5
C2H5
4-Diethyl amino-1-methyl buthyl amine
1
2
3
4
NCl
Cl
4,7-Dichloro quinoline
N
HN
CH
CH3
C
H2
H2
C
C
H2
N
C2H5
C2H5
Cl
Chloroquine
H
- HCl

Uses of Chloroquine:
First use Third useSecond use
Exhibiting
the
antimalarial
activity
Treatment
of malaria
during
pregnancy
Prevention &
treatment
of Malaria
exhibiting the
antimalarial activity
exhibiting the
antimalarial activity

Company
LOGO C) Pesticides:

Pesticides:
Q.1) What are pesticides? How are they classified? (W-12, W-13, W-16 & W-17, 4 Mark)
Q.2) What are pesticides? (S-13, S-14 & S-18, 1-2 Mark)
Q.3) Explain the terms: Pesticides. (W-15 & S-17, 2 Mark)
Q.4) What are the merits and demerits of using pesticides?
Q.5) Chemicals which are used to kill insects, fungi and weeds are called pesticides.
Defination:
Chemicals which are used
to kill insects, fungi and weeds
are called pesticides.
C
C
C
C
C
C
H
H
H
H
H
H
Benzene
+ 3 Cl2
C
C
C
C
C
C
H
H
H
H
H
H
Cl
Cl
Cl
Cl
Cl
Clsun light
Benzene hexa-chloride (B.H.C.)
(or Hexachloro-cyclohexane)
B.H.C. is insecticides, rarely used, harmful effects

Classification of Pesticides:
A
INSECTICIDES:
B
HERBICIDES:
C
FUNGICIDES:
D
RODENTICIDES:
Pesticides
I H F R

Dr. P. R. Padole
INSECTICIDES:
Organic
Insecticides:
stable to light and heat
Examples:
D.D.T.,
B.H.C.
Insecticides
Insects killer
Pesticides which destroy insects
are called as insecticides.
Phosphate
Insecticides:
poisonous to insects
Examples:
? ? ?

Malathion:
MALATHION (Insecticide):
Q.1) Give the method of preparation and uses of Malathion. (S-13, S-14, W-16, W-18 & S-19, 4 Mark)
Q.2) Write down the preparation of Malathion.
Q.3) Give method of preparation of Malathion, its importance to farmers and show how it is better than D.D.T.
Q.4) Write examples of organophosphate insecticide with formula and what is the mode of its action.
Q.5) Give any two uses of Malathion.
Q.6) Malathion is a organophosphate insecticide.
Q.7) What is Malathion? (W-15, 1/2 Mark)
a) Insecticide b) Herbicide c) Fingicide d) Rodenticide
+ P2S5 (CH3O)2 P2 SH
S
+ H2S
Methyl
Alcohol
Phosphorous
Pentasulphide O,O'-Dimethyl dithiophosphate
4 CH3OH
Step-1) Preparation of O,O'- dimethyl dithiophosphate from Methyl alcohol & P2S5:
Step-2) Preparation of Malathion from O,O'- dimethyl dithiophosphate:
(CH3O)2 P S H
S
CH-COOC2H5
CH-COOC2H5
O,O'-Dimethyl dithiophosphate
Diethyl maleate
CH3O
P S
S
CH.COOC2H5
Malathion
CH2.COOC2H5
CH3O

Uses of Malathion:
Malathion is a potent and effective
insecticide against insects, fungi and
weed. It has the merit of being less
toxic to mammals.
It is not hard insecticide. It can be
easily degraded by environmental
conditions. Thus it leaves no ill
effects.
It is a real boon to the farmers to
protect the crops from pests and
insects.

LOGO HERBICIDES:
 2,4-D is a synthetic auxin herbicide:
 2, 4 Dichloro-phenoxy-acetic acid (Herbicide):
Q.1) What are Herbicides? Give uses of [2, 4-D].
Q.2) Write the formula and name of [2, 4-D].
Q.3) What are herbicides? (S-17, 1 Mark)
Q.4) Pesticides which are used to destroy unwanted weeds in the crop are called herbicides.(S-16 & W-17, ½ M)
Q.5) What are herbicides? Give example. (S-17 & S-18, 2 Mark)
Q.6) Complete the following reaction and name the product formed in each of the reaction: (S-15, 2 Mark)
Q.7) Draw the structure of : 2, 4-D.(W-14, 1 Mark)
Q.8) Draw the correct structures of 2, 4D. (S-15, 2 Mark)
Q.9) Give any one method of preparation of [2, 4-D].
Q.10) Give any two uses of 2,4-D.
Q.11) 2,4-dichlorophenol with chloroacetic acid gives 2,4-D (2, 4 Dichloro-phenoxyacetic acid).
Q.12) Chlorination of phenoxyacetic acid gives 2,4-D (2, 4 Dichloro-phenoxyacetic acid).
Q.13) What is 2,4- D?
a) Insecticide b) Herbicide c) Fungicide d) Rodenticide
Q.14) How will you prepare [2, 4-D] from 2,4-dichlorophenol? (S-16 & S-18, 4 Mark)
Q.15) What are the different uses of [2, 4-D]? (W-15, 4 Mark)
Defination:
Pesticides which are used to destroy unwanted weeds in
the crop are called herbicides.
Cl
OH
Cl
2, 4- dichlorophenol
Cl CH2 C OH
Chloroacetic acid
O
?

Preparation of [2, 4-D]
(2, 4 Dichloro-phenoxyacetic acid) :
Method-1) When phenol is reacted with chlorine (two moles); to form
2, 4-dichlorophenol, which is further reacted with chloroacetic acid; to form
2, 4-D (2, 4 Dichloro-phenoxyacetic acid).
Cl
C
H2
O
OH
C
Cl
O
2, 4-Dichloro-phenoxy-acetic acid
[2, 4-D]
1
2
3
4
O-H
Cl
2, 4- dichloro-phenol
Cl CH2 C OH
Chloroacetic acid
O
OH
Phenol
Chlorine
2 Cl2
H Cl(-2 HCl)
H
+
-HClCl--Cl
Cl-Cl

Preparation of [2, 4-D]
(2, 4 Dichloro-phenoxyacetic acid) :
Method-2) When phenol is reacted with chloroacetic acid; to form
phenoxyacetic acid, which is further reacted with chlorine (two moles);
to form 2, 4-D (2, 4 Dichloro-phenoxy-acetic acid).
Cl--Cl
Cl-Cl
O
Phenol
H2C C OH
OH Cl O
O
OH
Phenoxy-acetic acid
Cl
C
H2
O
OH
C
Cl
O
2, 4-Dichloro-phenoxy-acetic acid
[2, 4-D]
+ 2Cl2
+ 2 HCl
H
H
- HCl
Chloroacetic acid
1
2
3
4

By Dr. P. R. Padole
Uses of [2, 4-D]:
First
Control of broadleaf
weeds BENZOIC ACID
2
2,4-D used as a
Herbicide in the world
Third
In laboratory for
plant research
synthetic auxin (plant hormone)

Do you know?
FUNGICIDES:
Q.1) What are fungicides?
Q.2) Chemicals which destroy fungi are called fungicides.
Q.3) Explain the term: Fungicides. (W-15 & W-18, 2 Mark)
Q.5) What are fungicides? Give example. (S-17, 2 Mark)
Q.6) Tea tee oil can be used as: (S-19, ½ Mark)
(a) Insecticide (b) Herbicide (c) Fungicide (d) Rodenticide

Chemicals which destroy such fungi
are called fungicides.

LOGO
THIRAM (Fungicide):
Q.1) Give any one method of preparation or synthesis of Thiram and its uses. (S-16, 4 Mark)
Q.2) What is the name of Thiram? (W-18, 1 Mark)
Q.3) Which chemical is used to prevent fungal diseases in seed and crops?
Q.4) Give any two uses of Thiram.
Q.5) Tetramethyl Thirum disulfide is also known as Thiram.
Q.6) What is Thiram?
a) Insecticide b) Fungicide c) Herbicide d) Rodenticide
Q.7) Tetramethyl thirum disulfide is____________.
a) Insecticide b) Herbicide c) Fungicide d) Rondenticide
Q.8) Which one of the following is used in the synthesis of Thiram?
a) Phenol b) Anthranilic Acid c) Phenolphthalein d) N,N-dimethyldithiocarbamate salt
Q.9) Which one of the following is used to prevent fungal diseases in the seed and crops?
a) D.D.T. b) 2,4-D c) Thiram d) Malathion
Q.10) Thiram has been used in the treatment of human scabies and as sun screen and as
bactericide applied directly to the skin.
Q.12) Give the method of preparation of Thiram. (S-19, 4 Mark)

LOGO
Preparation of THIRAM:
(Tetramethyl thiuram disulphide)
 Oxidation of N,N-dimethyl dithiocarbamate with H2O2 / Cl2 / I2
/ air; to form THIRAM (Tetramethyl thiuram disulphide).
OR
S
C
S
N
H3C
H3C
Na
Sodium salt of
N,N-Dimethyl dithio carbamate
Careful oxidation with
H2O2 / Cl2 / I2 / air
H3C
N
H3C
C
S
S S
C
S
N
CH3
CH3
Thiram
(Tetra methyl thiuram disulfide)
S
C
S
N
CH3
CH3
Na
+
Cl
Cl
Sodium salt of
N,N-Dimethyl dithio carbamate
- 2 NaCl
+

Uses of Thiram:
Accelerator and vulcanizing agent
Prevent fungal diseases in seed and crops
Treatment of human scabies,
as a sun screen
Animal repellent to protect
fruit trees

LOGO
Do you know?
RODENTICIDES:

LOGO
RODENTICIDES:
Rodenticides are pest control chemicals which
are used to kill rodents.

RODENTICIDES:
Q.1) Rodenticides are pest control chemicals which are used to kill rodents. (W-16, ½ Mark)
Q.2) Explain the term: Rodenticides. (S-17 & W-18, 2 Mark)
Q.3) What is meant by Rodenticides? (S-18, 1 Mark)

Drugs & pesticides by dr. pramod r. padole

Drugs & pesticides by dr. pramod r. padole

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