CHAPTER 3 INSECTICIDAL ACTIVITY OF QUINOLINE DERIVATIVESshodhganga.inflibnet.ac.in/bitstream/10603/43587/7/07_chapter_03.pdf · Chapter 3: Insecticidal activity of quinoline derivatives

Chapter 3: Insecticidal activity of quinoline derivatives

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CHAPTER 3

INSECTICIDAL ACTIVITY OF QUINOLINE DERIVATIVES

3.1 Introduction

Some people are concerned about the use of pesticides. Like all other

chemicals, pesticides should be treated with respect and not injured, but the

risks associated with pesticide use are often exaggerated out of all section,

especially when compared with those of the many domestic products and foods

we use or consume. Broad tests are performed throughout the development

stages of pesticides to minimize hazard to humans, animals and the

environment. Legislation covering development as well as the marketing,

selling, storage and use of pesticides are very strict and wide-ranging.

Many household refining agents are strong irritants. Alcohol may cause

birth defects. Many fruits and vegetables enclose toxins which are far more

potent than garden chemicals. Our body has evolved so that it can cope with a

certain amount of natural and man-made toxins and, provided we eat a

balanced and reasonable diet, there is no need to be excessively concerned

about what we eat. These comparisons should demonstrate that pesticides, used

sensibly, should not give rise to unnecessary concern.

The public are often concerned about the use of pesticides and not

always presented with a balanced view. It is important to be able to provide

reassurance about research and safety aspects (covered later) and to remind

ourselves of the need to keep pests under control. If left to their own devices,

weeds, pests and diseases will damage the health or appearance of cultivated

plants, to a greater or lesser amount. The situation tends to be made poorer by

the way in which we grow plants as gardeners by crowding a mixture of plants

into a small plot, or farmers by raising a large area of the same crop.

Insects are distinguished from other arthropods by having segmented

bodies, jointed legs, and external skeletons (exoskeletons), their body is

divided into three major regions:

1. The head, which having the parts of mouth, eyes, and a pair of antennae.


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2. The three-segmented thorax, which usually has three pairs of legs (hence

“Hexapoda”) in adults and usually one or two pairs of wings.

3. The many-segmented abdomen, which enclose the digestive, excretory,

and reproductive structure.

Humans consider certain insects as pests, and attempt to control using

insecticides and a host of other techniques. Some insects injure crops by

feeding on cell sap, leaves or fruits. The few bite humans and livestock to feed

on blood and some are capable of transmitting diseases to humans, pets and

livestock. The insects play a great role in pollination of flowering plants as a

many organisms rely on flowering plants. The insects are considered

ecologically beneficial as predators and a few provide direct economic benefit.

The silkworms and bees have been used widely by humans for the production

silk and honey respectively.

Problems likely to be come across by growers if pests are uncontrolled

include the following:

1. Reduced yields. Pest attack can severely reduce the yields of vegetable,

fruit and flower crops; sometimes the entire crop is obliterated. Along

with feeding on the plants, pests can, throughout spoilage, reduce yields

considerably and spread virus diseases.

2. Reduced quality. Even a minor reduction in quality can make all the

difference to commercial growers. To the gardener, quality aspects may

not be so important but it is still soul destroying to spend time and

money growing plants and then have your efforts ruined.

3. Competition. Weeds will deprive cultivated plants of water, space, light

and nutrients. They will also spoil the overall appearance of the garden.

4. Public health. Pesticides are used extensively throughout the world

against insects bearing potentially life-threatening diseases.

In this country they protect public health by controlling rodents which

can spread disease as well as spoil stored food. They are also used against flies.

Pests such as wasps and lice can spread diseases, and nuisance. Pesticides are


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not the only solution to these problems. However, combined with good

growing conditions, attention to hygiene and other cultural practices, they are

an effective and labor saving tool in the war against pests.

The present chapter divided into two sections:

� Section I: Insecticidal activity against stored product pest.

� Section II: Insecticidal activity against mosquitoes and aphids.


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Section I

INSECTICIDAL ACTIVITY AGAINST

STORED PRODUCT PEST

3. I.1 Introduction

The pulses are staple food throughout the world. The Cow pea Vigna

unguiculata (L.) crop is major source of protein for peoples in the Asia region.

The limiting factor in the production of pulses is qualitative and quantitative

losses caused by insect pest in field and storage [1]. Among them widest spread

and destructive primary pest of stored food product in India is Callosobruchus

chinensis [2].

The bruchids are most destructive pest having genus Callosobruchus,

family Bruchidae, and order Coleoptera. The Pulse beetle attack on pulses and

damage to seed is so serious that grubs destroy endosperm completely and

leaving only seed coat with empty cavities [3]. They are also responsible for

increasing heat through their respiratory and metabolic functions. The Pulse

beetles contaminate the rest food with undesirable odor. Alternatively, pest

infested food also causes major health hazards to human being [4]. The C.

chinensis breeds rapidly on different varieties of pulses having short life span

with great reproductive potential. The warm season and high moisture content

of the grain increases the rapid multiplication of the pest.

3. I.2 Review of Literature

The control of this insect pest is mainly depending on continued use of

organophosphorus, pyrethroid insecticides, fumigant methyl bromide and

phosphine [5]. These are still effective, but their constant use results in the

development of resistance [6-7]. They have very harmful effect on non-target

organisms and accountable for health and environmental problems. The use of

methyl bromide causes ozone deflection with high toxicity [8]. Therefore there

are alternatives to organophosphorus compounds for the control of storage

mites [9]. The cow pea seeds are generally used for family consumption,

therefore fumigant application is not suitable. There are some of the additional


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possibilities such as storage in plastic or steel containers, gamma irradiation, or

freezing to protect the pulses. However, most of these methods require high

inputs. Sometimes they are unaffordable for poor farmers and are often

unavailable [10]. An insecticidal compounds having oviposition and adult

deterrent activity exhibited a good control for insect pest in today’s agriculture

economy [11]. There is effect of some essential oils on the oviposition and

emergence of callosobruchus species [12].

Insecticidal and antifeedant activities of medicinal plant extracts against

Attagenus unicolor japonicas were also reported [13]. Also the insecticidal and

antifeedant effects of Junellia aspera, triterpenes and derivatives on Sitophilus

oryzae show good results [14]. The chemical pesticides are valuable in

controlling insect population both in field and storage. Insecticidal effect of

spinosad dust against four stored product insect species in different grain

commodities is observed [15-16]. The majority of agricultural products are

protected by using different heterocyclic compounds. Among them one of the

important heterocycle is quinoline [17-18]. Quinoline has diverse biological

active potential such as antibacterial [19], antituberculosis [20], anticancer [21],

antimalarial [22]. Some diphenyl quinolines and isoquinolines showed good

biological activities [23]. The 8-Hydroxyquinoline derivatives were proving to

be effective against plant hopper species [24]. The aminoquinoline Derivatives

are good against cockroaches [25]. There are some other examples for

quinoline acts as pesticides [26-28]. Therefore they have become the synthetic

targets of many organic and agricultural chemistry groups. The synthesis of 2,

3, 4-trisubstituted quinoline derivatives [29] through trans-esterfication were

done. Most of the reported compounds are new entities in heterocycles library

and interpretated on the basis of their spectroscopic data. With continuation our

previous success in bioscience [30] and above result in synthesis of new

quinoline derivatives motivated us to check the insecticidal activity of the said

compounds. With this vision, the details of the insecticidal, oviposition asnd

deterrent activities of new quinoline derivatives against pulse beetle on cow

pea seeds are given.


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3. I.3 Materials and Methods

The tri-substituted quinoline derivatives were synthesized by previously

reported method [29]. The following synthesized compounds have been

selected for insecticidal activities against Callosobruchus chinensis are shown

in the (Fig. 3. 1).

(Fig. 3.1) Structures of compounds The different structures of the tri-

substituted quinoline derivatives preliminary tested for insecticidal activity

against Callosobruchus chinensis.

These entire compounds preliminary tested for their insecticidal activity

against stored product pest. It has been observed that only dimethyl 6-chloro-4-

phenylquinoline-2,3-dicarboxylate (DCPQD-1) has shown excellent results.

Therefore only DDPQD-1 is selected for further investigation.


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3. I.4 Biological Assay

The biological assay was performed against a representative test

organism reared under the laboratory conditions.

3. I.4.1 Mass Rearing of Callosobruchus chinensis

Nucleus cultures of Callosobruchus were obtained from the Entomology

department of College of Agriculture, Pune and subsequent generations was

reared in humidity and temperature controlled laboratory conditions. Insect

rearing was carried out in 65 ± 5% relative humidity, 28 ± 2oC temperature and

10 hrs. Light: 14 hrs. dark. To obtain newly emerged pulse beetles of same

generation, 25 insects were released in a plastic container having 250 g of

cowpea seeds covered by a muslin cloth. After 24 hrs all the adults were

removed and egg laid seeds was maintained at required temperature and

humidity. The insects emerged after four weeks was used for entire

experiments. Insect eggs were counted by using hand lens.

3. I.4.2 Insecticidal Activity against Callosobruchus chinensis

3. I.4.2.1 Film Residue Method

Controlling adult is also another important step to protect post harvest

production. Film residue method [31] was used to test the mortality of C.

chinensis. To obtain test dosages individual quinoline compounds at dose 50

and 200 µg/mL was dissolved in acetone in vials of size 5 x 7.5 cm (W/L).

These were kept open to evaporate all solvent for 1 hr. The test solutions were

coated on inner surface of vials and freshly emerged (one day old) 20 adult

brucids were gently placed in vials. With each experiment, a set of control

sample containing only acetone solution (Qualigens) was run for comparison.

Each treatment was prepared in triplicate. Treated adults were held for 24 hrs

similar to the conditions used for maintaining the C. chinensis in the laboratory.

Mortalities were recorded after 24 hrs exposure, during which no food was

given to the adults. A simple microscope was used to verify each beetle by

tracing natural movement of its organs. Adults incapable of rising to the

surface or not showing the characteristic movement were considered moribund


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and added to the dead adult for calculating percentage of mortality. After the

preliminary screening, (DCPQD-1) is subjected to dose response bioassay to

determine lethal concentrations.

3. I.4.2.2 Dose -response Bioassay

Twenty Callosobruchus brucids at dose 25 to 400 µg/mL were used for

all the treatments. Commonly used insecticide Malathion® 50EC, India was

treated standard tested at 0.05% as positive control. Acetone is used as control.

The test is replicated thrice for each treatment and control. The results of

experiment with mortality percentage are given in the (Fig. 3.2).

(Fig. 3.2) Mortality data The percentage mortality of compound (DCPQD-1)

against Callosobruchus chinensis at different concentrations (µg/ml) showing

mortality rate increases with increase in concentration at 24, 48 and 72 hrs after

treatments.

3. I.4.2.3 Probit Analysis

The probit analysis was done on the probit program (Version 1.5) by

ecological monitoring division, environmental monitoring system laboratory,

U.S., environmental protection agency, Cincinnati, Ohio 45268. The regression


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equation for the compound (DCPQD-1) at 72 hrs after treatment is shown in

the (Fig. 3.3).

(Fig. 3.3) Regression equation The dose response relationship of toxicity data

of (DCPQD-1) against Callosobruchus chinensis showing regression equation

of probit mortality verses log of concentration.

3. I.4.3 Oviposition and Adult Deterrency

The 10 gm Vigna unguiculata (Cow pea) seeds treated separately with

each treatment of quinoline compounds at dose 25 to 100 µg/mL. These were

kept separately in small plastic containers of size 8.5 x 10 cm (W/L) covered

with muslin cloth. The seeds will be allowed to evaporate acetone for 1 hr and

used for the further experiment. Five pairs of adult bruchids of either sex were

released in each container. All the adults were removed after 5 days of release

and number of eggs laid was recorded. The oviposition deterrence activity (%

reduction in oviposition) was calculated using formula [32]. Total number of

adults emerged in each treatment was counted after 28 days of their release. A

control set was also maintained without any treatment of test solution well as


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with standard Neemarch® 50EC treatment with 100 µg/mL concentrations. The

percent adult emergence was calculated by reported formula [33].

3. I.4.4 Formulae

Oviposition deterrence = No. of eggs laid in control – No. of eggs laid in

treatment / No. of eggs laid in control x 100

Percent emergence = 100 x adult emergence / No. of eggs lay down.

Percent deterrence = 100 - Percent emergence

3. I.5. Results

3. I.5.1 Insecticidal Activity against C. chinensis (Complete Randomized

Block Design)

The efficacy of the compounds tested against Pulse beetle indicated that

all the treatments exhibited significantly superior over untreated solvent

control. When the observations recorded after 72 hrs after treatments

(DCPQD-1) shows 81.67% excellent mortality indicated superiority among the

other concentrations. The significant difference did not exist among the

concentration tested at 100 and 50µg/mL concentrations. The insecticidal

activity against C. chinensis were arranged in complete randomized block

design is listed in (Table 3.1).

(Table 3.1) Insecticidal Activity The insecticidal activity of synthesized

compound (DCPQD-1) at different concentrations against Callosobruchus

chinensis adults was shown in complete randomized block design. The Mean

percentage SE mortality was shown at 24, 48, and 72 hrs after treatments.

Sr.

No.

Treatments

(µg/ml)

Mortality (%) hrs after treatment

24* 48* 72*

1 25 0.00

(0.00)

0.00

(0.00)

21.67

(27.71)

2 50 5.00

(6.15)

8.33

(16.6)

36.67

(37.26)


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3 100 11.67

(19.89)

23.33

(25.30)

41.67

(40.20)

4 200 26.67

(31.07)

43.33

(41.16)

71.67

(57.86)

5 400 36.67

(37.26)

63.33

(52.74)

81.67

(64.70)

6 Malathion (0.05%) 51.67

(45.95)

71.67

(58.93)

91.67

(73.40)

7 Control (Solvent) 0.00

(0.00)

0.00

(0.00)

0.00

(0.00)

8 SE ± 1.16 1.54 1.75

9 CD @ 5% 3.96 5.22 5.96

* Mean of three replications

**Figures in parenthesis are Arcsin transformation

3. I.5.2 Probit Analysis

The (DCPQD-1) has shown 96.47 µg/mL LC50 value at 72 hrs after

treatments against the C. chinensis by probit analysis technique as shown in the

(Table 3.2).

(Table 3.2) Dose response study Probit analysis results of (DCPQD-1)

compound against Callosobruchus chinensis showing the LC50 value, upper

fugicidal limit, lower fugicidal limit and chi-square value.

Sr. No. HAT* Conc. (µg/ml) Regression

equation χ

2 LC 50 LFL UFL

1 24 556.08 417.14 903.81 Y=1.41x+2.21 2.84

2 48 250.91 213.53 305.05 Y=1.89x+0.45 3.08

3 72 96.47 79.40 116.95 Y=1.48x+0.87 4.65

* Hours after treatments


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3. I.5.3 Oviposition Deterrence

The results indicate that oviposition activity decreases with increase in

concentration as shown in (Fig. 3.4).

(Fig. 3.4) Oviposition deterrence The oviposition deterrent activity of

synthetic (DCPQD-1) against Callosobruchus chinensis at different

concentrations

Among the four concentrations, the 100µg/ml concentration shows the

significant oviposition deterrency is 80.00% as evidence from lowest number

of eggs laid by the female. The detail results have been given in (Table 3.3).

(Table 3.3) Oviposition deterrence The oviposition deterrent activity of

(DCPQD-1) against Callosobruchus chinensis at different concentrations

Sr. No. Concentration (µg/mL) Oviposition deterrence* (%)

1 25 32.21±3.51

2 50 51.28±5.13

3 75 64.10±4.04

4 100 80.00±3.21

5 Neemarch® EC 50 (100) 87.17±4.93

*±SD. Mean of the three replications


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3. I.5.4 Adult Deterrence

The adult deterrency shown by (DCPQD-1) at concentration of

100µg/ml is 64.63%. At the concentration of 75µg/ml, it shows 44.33% adult

deterrency. For the concentrations 50 and 25µg/ml the value for adult

deterrency is 28.70 and 27.30 respectively as shown in the (Table 3.4) and

(Fig. 3.5).

(Table 3.4) Adult deterrence The percentage of adult deterrence is against

Callosobruchus chinensis, for compound (DCPQD-1).

Sr. No. Concentration (µg/mL) Adult deterrence* (%)

1 25 27.34±3.79

2 50 38.70±2.51

3 75 44.33±4.04

4 100 64.63±2.52

5 Neemarch® EC 50 (100) 76.00±4.04

*±SD. Mean of the three replications

(Fig. 3.5) Adult deterrence The adult deterrent activity of the (DCPQD-1)

against Callosobruchus chinensis is at different concentrations showing the

increase in activity with increase in the concentration.


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The arrangement of experiment is shown in as shown in the (Fig. 3.6)

below.

(Fig. 3.6) Experimental set for activity against stored product pest

Callosobruchus chinensis.

3. I.6 Conclusions

We have reported the insecticidal activity of new quinoline derivatives.

The different concentration of (DCPQD-1) is found to be significantly effective

against Pulse beetle as compared to untreated control. It responded 81.67%

excellent mortality at 72 hrs after treatment. According to Probit analysis, LC50

value for the compound (DCPQD-1) is 96.47µg/ml. Along with insecticidal

activity, it also showed the 80.00% oviposition deterrent and 64.63% adult

deterrent activity at low concentrations is the main finding of this research

communication for future.


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Section II

INSECTICIDAL ACTIVITY AGAINST

MOSQUITO (Anopheles stephensi)

AND APHID (Myzus persicae)

3. II.1 Introduction

Insects have been major pests of humankind at least since the

beginning of recorded history. For this there are continuous efforts on structural

modification of pesticides useful for non target organisms but exhibiting good

pesticidal activities to target organism. To this day insects continue to cause

problems in domestic, agricultural, and health situations. It no wonders that

people have continually sought new solutions to controlling insect pests. Even

when new control methods are discovered and established, insects evolve into

resistance species so that the method is only of real value for a few brief years.

Modern science and technology are now enabling scientists to find

physiological and biochemical events critical to insects. Armed with this new

knowledge, researchers should be able to develop novel control strategies that

focus on key events such that they can be altered, influenced, disrupted, and/or

inhibited the biological process.

In the 21th century, pesticide must have the characteristics of high

efficiency, low toxicity, economy and friendly environmental profile.

Medicament and pesticide researchers pay greatly attention to amide

compounds because of their high-efficiency, low toxicity and safety to

environment, in recent years, amide compounds have become the mainstream

in new pesticide discovery. Amide compounds also have broad biological

activities such as insecticide, acaricide, fungicide and herbicide, and amide

substructure is often used as pharmacophore in new pesticide discovery.

The evolvement of discovery, varieties, action mechanism and structure-

activity relationship of amide compounds were introduced in detail. And

phenoxy acetamide has the role of inhibition of cell division, and to some


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extent to enhance the role of antineoplastic agents, and has a good fungicidal

activity. Oxygen and nitrogen containing heterocycles are getting immense

importance in the area of pharmaceuticals and agrochemicals. Pesticides belong

to agrochemical area, which includes insecticides, fungicides, rodenticides,

herbicides and fumigants. Among pesticides, insecticides are widely used

chemicals by Indian farmers to control various diseases caused by different

insects. Indiscriminate usage of pesticides in the fields is causing resistance

development by insects resulting lower yields of the crops. Ultimately the

farmer is at receiving end with enormous financial loss.

To overcome this problem an intense research is currently in progress to

develop pyrethroids, nicotinoids where the usage of chemical is at gross level;

however, the insect based diseases are well controlled. This is the emerging

area with a lot of potential and there is a need to synthesize a new class of

pyrethroids, nicotinoids and subjected to bio-evaluation in order to find a

promising candidate. In addition, quinolines as a very important class of

nitrogen -containing heterocyclic compounds, are widely used in health care

and plant protection.

Man knows that he will die some day, still his desire to live as long as

possible. Diseases are our main enemies because they prevent us not only from

enjoying happy and healthy life but also cut short our stay on this earth. The

race has been going on between the diseases and scientific investigations. The

majority of pharmaceutical products that mimic natural products with

biological activity are heterocycles. Among them one of the important

heterocycle is quinoline. Quinoline has diverse biological activities such as

antibacterial [34], antituberculosis [35], anticancer [36], antimalarial [37],

antifungal [38] and antimicrobial [39]. Due to their enormous importance they

have become the synthetic targets of many organic and medicinal chemistry

groups [40]. The structural diversity of quinolines has been based on the

various conventional name reactions [41].


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When we say undesirable organisms, we are referring to organisms

(plants, animals, insects, etc.) that are harmful to us. The pests eat our crops,

while others spread diseases. Weeds can be considered a pest for just growing

in the wrong places (our yards). The chemicals which used for controlling pests

are calls pesticides. In addition to applications in agriculture, pesticides have

uses. Many pests transmit diseases which are very dangerous to us. For

example, in the past, malaria was once a serious disease that killed millions of

people worldwide. To overcome this problem, we used DDT, to kill the

mosquitoes. It was victorious, and the number of people who died from malaria

minimize drastically.

3. II.2 Review of Literature

The identification of novel larvicidal and insecticidal compounds

requires the bioassay tests. Malaria is one of the most common vector-borne

diseases extensive in tropical and subtropical regions, including America, Asia,

and Africa [42]. It is a complex disease caused by plasmodial species and is

vectored by female anopheline mosquitoes in which Anopheles stephensi is

responsible in urban areas [43]. Vector mosquitoes control is an essential and

effective part for reducing transmission of vector-borne diseases [44].

Successful method of reducing mosquito densities to an appreciable level for

which malaria epidemics can be controlled is by attacking the larval breeding

places by the use of larvicides [45-46]. In many parts of the world chemical

insecticides have continued to be used for controlling mosquitoes. However,

control of malaria and other mosquito borne diseases becoming more difficult

because the development of resistance in mosquitoes against currently used

synthetic insecticides [47-49].

Aphid is a polyphagus pest and is one of the most serious pests

due to their high population reduces the yield and quality of crop due to sap

sucking and transmission of the numerous viruses of plant [50-51]. Potato leaf

roll virus (PLRV) is transmitted by few aphid species in which M. persicae is

the most efficient and persistent [52]. Control of the spread of PLRV relies


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mainly on planting healthy seed potatoes and on the timely application of

insecticides to suppress aphid populations [53]. However, insecticides rapidly

select for insecticide resistant M. persicae and other aphid species [54-57]. This

has been possible through the continued discovery and commercialization of

new insecticide chemistries. Therefore, it is critically necessary to discover new

insecticidal candidates with different chemistries and with varying modes of

action [58].

4. II.3 Materials and Methods

The synthetic approach of 2, 3, 4-trisubstituted quinolines by previously

reported method [59] were done through trans-esterification are as selected for

insecticidal activities are shown in the (Fig. 3. 1).

(Fig. 3.1) Structures of compounds The selected compounds of the tri-

substituted quinoline derivatives tested for insecticidal activity against

mosquitoes and aphids.

Most of the reported compounds were new entities in heterocycle library

and interpretated on the basis of their spectroscopic data. With continuation

our previous success in bioactive compounds [60] and above result in the

synthesis of new quinoline derivatives moved us to check an insecticidal

activity of the said quinoline derivatives. The following compounds have been

selected to investigate an insecticidal activity against mosquito and aphids on

the basis of their structure and primary test.


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3. II.3.1 Biological Assay

All bioassays were performed on representative test organisms. The

bioassay was repeated at 27 ± 2°C according to statistical requirements.

Assessments were made on a dead or alive basis. The mortality rates were

corrected using Abbott’s formula. Evaluations are based on a percentage scale

of 0-100 in which 0 % no activity and 100 % total kill.

3. II.3.2 Larvicidal activity against mosquito, Anopheles stephensi (Liston)

3. II.3.2.1 Solution preparation

The specific derivatives of quinoline, 250 mg was placed in a standard

measuring flask and dissolved in 0.9 ml of acetone and 0.1 ml of Tween 80 was

added as an emulsifier. This mixture was diluted to 250 ml using tap water to

prepare the stock solution, which was as a stock solution (1000 µg/ml). From

stock solution, 100 ml was diluted with water up to 250 ml to prepare 400

µg/ml test solution.

This sequential method was used to prepare 200, 100, 50 and 25 µg/ml

solutions. A mixture of 0.9 ml of acetone and 0.1 ml of Tween 80 was made up

to 250 ml in a standard measuring flask by adding tap water to serve as the

control solution. An insecticidal activity was determined according to the

guidelines of WHO and Yankanchi et al and Patil et al, [61-62]. Bioassays

were conducted for 24 hrs in glass beakers of 250 ml of test solutions with

three replicates [Fig. 3.8a and 3.8b].

(Fig. 3.8a) The Experimental Set for Larvicidal activity against mosquitoes,

Anopheles stephensi


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(Fig. 3.8b) Larvicidal activity against mosquitoes, Anopheles stephensi at two

concentrations 100(µg/ml) and 200(µg/ml) of 1a

Twenty-five third instar larvae of Anopheles stephensi were introduced

into each test solution with the appropriate control solution. The results were

observed after 24 hrs and the percentage mortality was corrected by using

Abbott’s formula [63]. The LC50 values are calculated using the computation

program of probit analysis [64]. The mortality data were recorded in the (Table

3.5) as follows.

(Table 3.5) Insecticidal activity of quinoline derivatives 1a-d against mosquito

Sr. No.

Conc. (µg/ml)

Percentage mortality 1a 1b 1c 1d

1 25 23 20 17 23

2 50 37 37 27 30

3 100 47 50 43 33

4 200 53 73 67 53

5 400 67 87 87 70


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3. II.3.3 Insecticidal activity against Green peach Aphid, Myzus persicae

(Sulzer)

The insecticidal activities of the tri-substituted quinolines (1a-d) were

evaluated using a previously reported procedure [65-66]. The insecticidal

activity was tested against aphid, Myzus persicae by leaf-dip method [Fig 3.9a]

(Fig. 3.9a) Insecticidal activity against Green peach Aphids, Myzus persicae

Tobacco (Nicotiana tabacum) leaves of 5 cm area were dipped in 1ml of

test solution and allowed to dry. The leaves were placed on moistened pieces of

filter paper in petri dishes. The dishes were infested with 25 aphid adults with

three replicates [Fig. 3.9b]. The controls used acetone instead of insecticide

solution.

(Fig. 3.9b) Insecticidal activity against Green peach Aphids, Myzus persicae at

concentration 100(µg/ml) of 1b


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Percentage mortalities were evaluated 24 hrs after treatment [Fig.

3.9c]. The aphids which are dead and which are not moves after touch by

painting brush are considered as dead.

(Fig. 3.9c) Dead Green peach Aphids, Myzus persicae after application of 1b

The data were corrected and subjected to probit analysis and LD50

values were determined. The mortality data are summarized in (Table 3.6).

(Table 3.6) Insecticidal activity of quinoline derivatives (1a-d) against Aphid

Sr. No.

Conc. (µg/ml)

Percentage mortality 1a 1b 1c 1d

1 25 27 43 36 33

2 50 47 50 50 47

3 100 63 67 63 50

4 200 70 77 73 63

5 400 83 90 87 77

3. II.4 Results and Discussion

All the tested compounds have been prepared according to our reported

procedure. The percentage mortality of mosquito (Anopheles stephensi) and

green peach aphid, (Myzus persicae) of the target compounds are summarized

in the (Table 3.5) and (Table 3.6). Compound 1b found to be high larvicidal


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activity against mosquito with an LC50 value of 85.74µg/ml as shown in the

(Table 3.7).

(Table 3.7) The 24 hrs LC50 values (ppm) and their 95 % fiducidal (upper and

lower) limits, regression equation and Chi-square (χ2) values of quinoline

derivatives for the late 3rd instar larvae of Anopheles stephensi.

Sr.

No. Comp.

Conc. (µg/ml) Regression equation χ

2* LC 50 LFL UFL

1 1a 137.03 102.95 192.62 Y = 2.9813 + 0.9433 X 1.02 2 1b 85.74 71.74 101.73 Y = 1.8607 + 1.6267 X 1.00

3 1c 107.20 91.18 126.52 Y = 0.6800 + 2.0900 X 2.74

4 1d 164.14 126.99 226.46 Y = 2.7000 + 1.0400 X 4.27

*at (0.05) significance level

The compound 1b revealed high insecticidal activity against aphids with

LD50 value of 83.58µg/ml as shown in the (Table 3.8).

(Table 3.8) The 24 hrs LD50 values (ppm) and their 95 % fiducidal (upper and

lower) limits, regression equation and Chi-square (χ2) values of quinoline

derivatives for the adult of Myzus persicae.

Sr.

No. Compds.

Conc. (µg/ml) Regression equation χ

2* LC 50 LFL UFL

1 1a 130.75 101.12 162.63 Y = 1.7807 + 1.4667 X 1.81

2 1b 83.58 58.96 108.07 Y = 2.6500 + 1.2200 X 1.74

3 1c 102.93 75.51 130.97 Y = 2.3957 + 1.0967 X 0.64

4 1d 151.90 108.78 202.28 Y = 2.9863 + 0.9233 X 1.77

*at p= (0.05) significance level

Our results are coinciding with the previous results [67] that the

introduction of a hydrophilic factor, such as the use of heterocyclic rings

including oxygen and/or nitrogen might benefit the bioactivity of compounds.

The increase of electronegative atoms in the molecule that is application of an

electronegative atom (i.e., chlorine, fluorine) encouraged better bioactivity as

shown in the (Fig. 3.10).


112

(Fig. 3.10) Insecticidal efficacy (LC50) against Mosquitoes and (LD50)

against Aphids.

3. II.5 Conclusions

In conclusion, the different 2, 3, 4-trisubstituted quinoline derivatives

have been tested for their insecticidal activities against mosquitoes and aphids.

Among the tested compounds, diethyl-4-phenyl-6-chloroquinoline-2,3-

dicarboxylate 1b is found to be potential insecticide for protection of animals

and plants with lowest LC50 and LD50 from mosquito and aphid respectively.


113

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