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Home > Security > Penetration Testing > Python Penetration Testing Essentials
Python Penetration Testing Essentials
Python Penetration Testing Essentials

Python Penetration Testing Essentials: Employ the power of Python to get the best out of pentesting

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Python Penetration Testing Essentials

Chapter 1. Python with Penetration Testing and Networking

Penetration (pen) tester and hacker are similar terms. The difference is that penetration testers work for an organization to prevent hacking attempts, while hackers hack for any purpose such as fame, selling vulnerability for money, or to exploit vulnerability for personal enmity.

Lots of well-trained hackers have got jobs in the information security field by hacking into a system and then informing the victim of the security bug(s) so that they might be fixed.

A hacker is called a penetration tester when they work for an organization or company to secure its system. A pentester performs hacking attempts to break the network after getting legal approval from the client and then presents a report of their findings. To become an expert in pentesting, a person should have deep knowledge of the concepts of their technology. In this chapter, we will cover the following topics:

  • The scope of pentesting
  • The need for pentesting
  • Components to be tested
  • Qualities of a good pentester
  • Approaches of pentesting
  • Understanding the tests and tools you'll need
  • Network sockets
  • Server socket methods
  • Client socket methods
  • General socket methods
  • Practical examples of sockets
  • Socket exceptions
  • Useful socket methods

Introducing the scope of pentesting

In simple words, penetration testing is to test the information security measures of a company. Information security measures entail a company's network, database, website, public-facing servers, security policies, and everything else specified by the client. At the end of the day, a pentester must present a detailed report of their findings such as weakness, vulnerability in the company's infrastructure, and the risk level of particular vulnerability, and provide solutions if possible.

The need for pentesting

There are several points that describe the significance of pentesting:

  • Pentesting identifies the threats that might expose the confidentiality of an organization
  • Expert pentesting provides assurance to the organization with a complete and detailed assessment of organizational security
  • Pentesting assesses the network's efficiency by producing huge amount of traffic and scrutinizes the security of devices such as firewalls, routers, and switches
  • Changing or upgrading the existing infrastructure of software, hardware, or network design might lead to vulnerabilities that can be detected by pentesting
  • In today's world, potential threats are increasing significantly; pentesting is a proactive exercise to minimize the chance of being exploited
  • Pentesting ensures whether suitable security policies are being followed or not

Consider an example of a well-reputed e-commerce company that makes money from online business. A hacker or group of black hat hackers find a vulnerability in the company's website and hack it. The amount of loss the company will have to bear will be tremendous.

Components to be tested

An organization should conduct a risk assessment operation before pentesting; this will help identify the main threats such as misconfiguration or vulnerability in:

  • Routers, switches, or gateways
  • Public-facing systems; websites, DMZ, e-mail servers, and remote systems
  • DNS, firewalls, proxy servers, FTP, and web servers

Testing should be performed on all hardware and software components of a network security system.

Qualities of a good pentester

The following points describe the qualities of good pentester. They should:

  • Choose a suitable set of tests and tools that balance cost and benefits
  • Follow suitable procedures with proper planning and documentation
  • Establish the scope for each penetration test, such as objectives, limitations, and the justification of procedures
  • Be ready to show how to exploit the vulnerabilities
  • State the potential risks and findings clearly in the final report and provide methods to mitigate the risk if possible
  • Keep themselves updated at all times because technology is advancing rapidly

A pentester tests the network using manual techniques or the relevant tools. There are lots of tools available in the market. Some of them are open source and some of them are highly expensive. With the help of programming, a programmer can make his own tools. By creating your own tools, you can clear your concepts and also perform more R&D. If you are interested in pentesting and want to make your own tools, then the Python programming language is the best, as extensive and freely available pentesting packages are available in Python, in addition to its ease of programming. This simplicity, along with the third-party libraries such as scapy and mechanize, reduces code size. In Python, to make a program, you don't need to define big classes such as Java. It's more productive to write code in Python than in C, and high-level libraries are easily available for virtually any imaginable task.

If you know some programming in Python and are interested in pentesting this book is ideal for you.

Defining the scope of pentesting

Before we get into pentesting, the scope of pentesting should be defined. The following points should be taken into account while defining the scope:

  • You should develop the scope of the project in consultation with the client. For example, if Bob (the client) wants to test the entire network infrastructure of the organization, then pentester Alice would define the scope of pentesting by taking this network into account. Alice will consult Bob on whether any sensitive or restricted areas should be included or not.
  • You should take into account time, people, and money.
  • You should profile the test boundaries on the basis of an agreement signed by the pentester and the client.
  • Changes in business practice might affect the scope. For example, the addition of a subnet, new system component installations, the addition or modification of a web server, and so on, might change the scope of pentesting.

The scope of pentesting is defined in two types of tests:

  • A non-destructive test: This test is limited to finding and carrying out the tests without any potential risks. It performs the following actions:
    • Scans and identifies the remote system for potential vulnerabilities
    • Investigates and verifies the findings
    • Maps the vulnerabilities with proper exploits
    • Exploits the remote system with proper care to avoid disruption
    • Provides a proof of concept
    • Does not attempt a Denial-of-Service (DoS) attack
  • A destructive test: This test can produce risks. It performs the following actions:
    • Attempts DoS and buffer overflow attacks, which have the potential to bring down the system

Approaches to pentesting

There are three types of approaches to pentesting:

  • Black-box pentesting follows non-deterministic approach of testing
    • You will be given just a company name
    • It is like hacking with the knowledge of an outside attacker
    • There is no need of any prior knowledge of the system
    • It is time consuming
  • White-box pentesting follows deterministic approach of testing
    • You will be given complete knowledge of the infrastructure that needs to be tested
    • This is like working as a malicious employee who has ample knowledge of the company's infrastructure
    • You will be provided information on the company's infrastructure, network type, company's policies, do's and don'ts, the IP address, and the IPS/IDS firewall
  • Gray-box pentesting follows hybrid approach of black and white box testing
    • The tester usually has limited information on the target network/system that is provided by the client to lower costs and decrease trial and error on the part of the pentester
    • It performs the security assessment and testing internally

Introducing Python scripting

Before you start reading this book, you should know the basics of Python programming, such as the basic syntax, variable type, data type tuple, list dictionary, functions, strings, methods, and so on. Two versions, 3.4 and 2.7.8, are available at python.org/downloads/.

In this book, all experiments and demonstration have been done in Python 2.7.8 Version. If you use Linux OS such as Kali or BackTrack, then there will be no issue, because many programs, such as wireless sniffing, do not work on the Windows platform. Kali Linux also uses the 2.7 Version. If you love to work on Red Hat or CentOS, then this version is suitable for you.

Most of the hackers choose this profession because they don't want to do programming. They want to use tools. However, without programming, a hacker cannot enhance his2 skills. Every time, they have to search the tools over the Internet. Believe me, after seeing its simplicity, you will love this language.

Understanding the tests and tools you'll need

As you must have seen, this book is divided into seven chapters. To conduct scanning and sniffing pentesting, you will need a small network of attached devices. If you don't have a lab, you can make virtual machines in your computer. For wireless traffic analysis, you should have a wireless network. To conduct a web attack, you will need an Apache server running on the Linux platform. It will be a good idea to use CentOS or Red Hat Version 5 or 6 for the web server because this contains the RPM of Apache and PHP. For the Python script, we will use the Wireshark tool, which is open source and can be run on Windows as well as Linux platforms.

Learning the common testing platforms with Python

You will now perform pentesting; I hope you are well acquainted with networking fundamentals such as IP addresses, classful subnetting, classless subnetting, the meaning of ports, network addresses, and broadcast addresses. A pentester must be perfect in networking fundamentals as well as at least in one operating system; if you are thinking of using Linux, then you are on the right track. In this book, we will execute our programs on Windows as well as Linux. In this book, Windows, CentOS, and Kali Linux will be used.

A hacker always loves to work on a Linux system. As it is free and open source, Kali Linux marks the rebirth of BackTrack and is like an arsenal of hacking tools. Kali Linux NetHunter is the first open source Android penetration testing platform for Nexus devices. However, some tools work on both Linux and Windows, but on Windows, you have to install those tools. I expect you to have knowledge of Linux. Now, it's time to work with networking on Python.

Network sockets

A network socket address contains an IP address and port number. In a very simple way, a socket is a way to talk to other computers. By means of a socket, a process can communicate with another process over the network.

In order to create a socket, use the socket.socket() function that is available in the socket module. The general syntax of a socket function is as follows:

s = socket.socket (socket_family, socket_type, protocol=0)

Here is the description of the parameters:

socket_family: socket.AF_INET, PF_PACKET

AF_INET is the address family for IPv4. PF_PACKET operates at the device driver layer. The pcap library for Linux uses PF_PACKET. You will see more details on PF_PACKET in Chapter 3, Sniffing and Penetration Testing. These arguments represent the address families and the protocol of the transport layer:

Socket_type : socket.SOCK_DGRAM, socket.SOCK_RAW,socket.SOCK_STREAM

The socket.SOCK_DGRAM argument depicts that UDP is unreliable and connectionless, and socket.SOCK_STREAM depicts that TCP is reliable and is a two-way, connection-based service. We will discuss socket.SOCK_RAW in Chapter 3, Sniffing and Penetration Testing.

protocol

Generally, we leave this argument; it takes 0 if not specified. We will see the use of this argument in Chapter 3, Sniffing and Penetration Testing.

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Description

If you are a Python programmer or a security researcher who has basic knowledge of Python programming and want to learn about penetration testing with the help of Python, this book is ideal for you. Even if you are new to the field of ethical hacking, this book can help you find the vulnerabilities in your system so that you are ready to tackle any kind of attack or intrusion.

Who is this book for?

If you are a Python programmer or a security researcher who has basic knowledge of Python programming and want to learn about penetration testing with the help of Python, this book is ideal for you. Even if you are new to the field of ethical hacking, this book can help you find the vulnerabilities in your system so that you are ready to tackle any kind of attack or intrusion.

What you will learn

  • Monitor the Ethernet IP and TCP traffic over the network
  • Explore wireless traffic with the help of various programs
  • Perform wireless attacks with Python programs
  • Check live systems and distinguish between the operating system and services of a remote machine
  • Broaden your concepts in pentesting right from the basics of the client/server architecture in Python
  • Gather passive information from a website using automated scripts
  • Perform XSS, SQL injection, and parameter tampering attacks
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Publication date : Jan 28, 2015
Length: 178 pages
Edition : 1st
Language : English
ISBN-13 : 9781784398583
Category :
Security
Languages :
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Concepts :
Penetration Testing

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Length: 178 pages
Edition : 1st
Language : English
ISBN-13 : 9781784398583
Category :
Security
Languages :
Python
Concepts :
Penetration Testing

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Table of Contents

8 Chapters
1. Python with Penetration Testing and Networking Chevron down icon Chevron up icon
1. Python with Penetration Testing and Networking
Introducing the scope of pentesting
Approaches to pentesting
Introducing Python scripting
Understanding the tests and tools you'll need
Learning the common testing platforms with Python
Network sockets
Server socket methods
Client socket methods
General socket methods
Moving on to the practical
Summary
2. Scanning Pentesting Chevron down icon Chevron up icon
2. Scanning Pentesting
How to check live systems in a network and the concept of a live system
What are the services running on the target machine?
Summary
3. Sniffing and Penetration Testing Chevron down icon Chevron up icon
3. Sniffing and Penetration Testing
Introducing a network sniffer
Implementing a network sniffer using Python
Learning about packet crafting
Introducing ARP spoofing and implementing it using Python
Testing the security system using custom packet crafting and injection
Summary
4. Wireless Pentesting Chevron down icon Chevron up icon
4. Wireless Pentesting
Wireless SSID finding and wireless traffic analysis by Python
Wireless attacks
Summary
5. Foot Printing of a Web Server and a Web Application Chevron down icon Chevron up icon
5. Foot Printing of a Web Server and a Web Application
The concept of foot printing of a web server
Introducing information gathering
Information gathering of a website from SmartWhois by the parser BeautifulSoup
Banner grabbing of a website
Hardening of a web server
Summary
6. Client-side and DDoS Attacks Chevron down icon Chevron up icon
6. Client-side and DDoS Attacks
Introducing client-side validation
Tampering with the client-side parameter with Python
Effects of parameter tampering on business
Introducing DoS and DDoS
Summary
7. Pentesting of SQLI and XSS Chevron down icon Chevron up icon
7. Pentesting of SQLI and XSS
Introducing the SQL injection attack
Types of SQL injections
Understanding the SQL injection attack by a Python script
Learning about Cross-Site scripting
Summary
Index Chevron down icon Chevron up icon
Index

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Kindle Customer Mar 25, 2015
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Although the subject of security is not my area of expertise I bought this book with the idea of grasping the principles of systems / networks penetration in order to become more familiar with the tools used for such purposes.This is the kind of book that not only teaches you something new but does it in a refreshing way. I made me wonder: why would anyone rewrite some well known script in bash (or even a bat file for that matter) in Python ? because we can ! I can hear a lot of voices saying it outloud. But what if I told you that you can rewrite complete tools to sniff a network ? or how about using sockets directly from the command line ? If you ever wondered that too, well this is the book for us.Below you can see an image of my (Enthought Canopy) command line trying to get through the office's Proxy Server using one of the book's scripts.
Amazon Verified review Amazon
perceive Mar 15, 2015
Full star icon Full star icon Full star icon Full star icon Empty star icon 4
We have another Python book, this time dedicated to Penetration Testing.The book itself is as much as use case scenario for using Python as a guide to Pen Testing, so if you are expecting a pen testing education I'd suggest more than this book here.However, if what you are after is how to use Python with real world examples this book may suit your needs. The provided code examples (you can download the code as well from Packt) are all very helpful in understanding where Python can be used in this field.If you have some experience in Pen testing already, the code will be more useful than nearly anything else.The main reason that I reduced the mark to 4 stars was that the books examples are all Python 2, not 3. For a book published in 2015 I'd like to know that the future proofing of my learning was in place. While there is an abundance of Python 2 code out there and it will not be going away anytime soon, the general python community is showing signs that the schism between 2 and 3 are reducing with more and more python 3 code being written. This is a minor issue for me, as most OS that I use will be maintaining support for both as far as I can see into the future.
Amazon Verified review Amazon
Tim Crothers Mar 16, 2015
Full star icon Full star icon Full star icon Full star icon Empty star icon 4
Solid introduction to using Python for Pentesting applications. The book doesn't go into an extreme amount of depth but then this is an "essentials" book. Topic was covered logically and the included sample code makes for a good baseline for crafting your own penetration related tools in Python. The book could use some more editing to clean up errors but they were all minor in nature so I only dinged one star as a result. Overall very good starting place if you wish to learn to craft some of your own tools for doing pentesting in Python. Well worth the purchase price.
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Finn M Glas Jan 14, 2019
Full star icon Full star icon Full star icon Full star icon Empty star icon 4
Good but long read that tought me a lot
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WagesOfSin Jul 08, 2017
Full star icon Full star icon Full star icon Empty star icon Empty star icon 3
Its a pretty good book, I'm half way through and using it to prep me for other Python Pentest books which delve into the topic deeply. I thought a good strategy would be to use this lighter book as an intro for deeper books such as Violent Python. My biggest concern though is the editing! I have have to correct lines in the code which had typos all through out the book.
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About the author

Profile icon Mohit Raj
Mohit Raj
Mohit Raj is a Python programmer with a keen interest in the field of information security. He completed his bachelor's degree in technology in computer science from Kurukshetra University, Kurukshetra, and his masters in engineering (2012) in computer science from Thapar University, Patiala. He is a C|EH, ECSA from EC-Council USA and a former IBMer. Mohit currently works at Sapient, and has published several articles in national and international magazines. He is the author of Python Penetration Testing Essentials and Python: Penetration Testing for Developers, also by Packt Publishing.
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What is the digital copy I get with my Print order? Chevron down icon Chevron up icon

When you buy any Print edition of our Books, you can redeem (for free) the eBook edition of the Print Book you’ve purchased. This gives you instant access to your book when you make an order via PDF, EPUB or our online Reader experience.

What is the delivery time and cost of print book? Chevron down icon Chevron up icon

Shipping Details

USA:

'

Economy: Delivery to most addresses in the US within 10-15 business days

Premium: Trackable Delivery to most addresses in the US within 3-8 business days

UK:

Economy: Delivery to most addresses in the U.K. within 7-9 business days.
Shipments are not trackable

Premium: Trackable delivery to most addresses in the U.K. within 3-4 business days!
Add one extra business day for deliveries to Northern Ireland and Scottish Highlands and islands

EU:

Premium: Trackable delivery to most EU destinations within 4-9 business days.

Australia:

Economy: Can deliver to P. O. Boxes and private residences.
Trackable service with delivery to addresses in Australia only.
Delivery time ranges from 7-9 business days for VIC and 8-10 business days for Interstate metro
Delivery time is up to 15 business days for remote areas of WA, NT & QLD.

Premium: Delivery to addresses in Australia only
Trackable delivery to most P. O. Boxes and private residences in Australia within 4-5 days based on the distance to a destination following dispatch.

India:

Premium: Delivery to most Indian addresses within 5-6 business days

Rest of the World:

Premium: Countries in the American continent: Trackable delivery to most countries within 4-7 business days

Asia:

Premium: Delivery to most Asian addresses within 5-9 business days

Disclaimer:
All orders received before 5 PM U.K time would start printing from the next business day. So the estimated delivery times start from the next day as well. Orders received after 5 PM U.K time (in our internal systems) on a business day or anytime on the weekend will begin printing the second to next business day. For example, an order placed at 11 AM today will begin printing tomorrow, whereas an order placed at 9 PM tonight will begin printing the day after tomorrow.


Unfortunately, due to several restrictions, we are unable to ship to the following countries:

  1. Afghanistan
  2. American Samoa
  3. Belarus
  4. Brunei Darussalam
  5. Central African Republic
  6. The Democratic Republic of Congo
  7. Eritrea
  8. Guinea-bissau
  9. Iran
  10. Lebanon
  11. Libiya Arab Jamahriya
  12. Somalia
  13. Sudan
  14. Russian Federation
  15. Syrian Arab Republic
  16. Ukraine
  17. Venezuela
What is custom duty/charge? Chevron down icon Chevron up icon

Customs duty are charges levied on goods when they cross international borders. It is a tax that is imposed on imported goods. These duties are charged by special authorities and bodies created by local governments and are meant to protect local industries, economies, and businesses.

Do I have to pay customs charges for the print book order? Chevron down icon Chevron up icon

The orders shipped to the countries that are listed under EU27 will not bear custom charges. They are paid by Packt as part of the order.

List of EU27 countries: www.gov.uk/eu-eea:

A custom duty or localized taxes may be applicable on the shipment and would be charged by the recipient country outside of the EU27 which should be paid by the customer and these duties are not included in the shipping charges been charged on the order.

How do I know my custom duty charges? Chevron down icon Chevron up icon

The amount of duty payable varies greatly depending on the imported goods, the country of origin and several other factors like the total invoice amount or dimensions like weight, and other such criteria applicable in your country.

For example:

  • If you live in Mexico, and the declared value of your ordered items is over $ 50, for you to receive a package, you will have to pay additional import tax of 19% which will be $ 9.50 to the courier service.
  • Whereas if you live in Turkey, and the declared value of your ordered items is over € 22, for you to receive a package, you will have to pay additional import tax of 18% which will be € 3.96 to the courier service.
How can I cancel my order? Chevron down icon Chevron up icon

Cancellation Policy for Published Printed Books:

You can cancel any order within 1 hour of placing the order. Simply contact customercare@packt.com with your order details or payment transaction id. If your order has already started the shipment process, we will do our best to stop it. However, if it is already on the way to you then when you receive it, you can contact us at customercare@packt.com using the returns and refund process.

Please understand that Packt Publishing cannot provide refunds or cancel any order except for the cases described in our Return Policy (i.e. Packt Publishing agrees to replace your printed book because it arrives damaged or material defect in book), Packt Publishing will not accept returns.

What is your returns and refunds policy? Chevron down icon Chevron up icon

Return Policy:

We want you to be happy with your purchase from Packtpub.com. We will not hassle you with returning print books to us. If the print book you receive from us is incorrect, damaged, doesn't work or is unacceptably late, please contact Customer Relations Team on customercare@packt.com with the order number and issue details as explained below:

  1. If you ordered (eBook, Video or Print Book) incorrectly or accidentally, please contact Customer Relations Team on customercare@packt.com within one hour of placing the order and we will replace/refund you the item cost.
  2. Sadly, if your eBook or Video file is faulty or a fault occurs during the eBook or Video being made available to you, i.e. during download then you should contact Customer Relations Team within 14 days of purchase on customercare@packt.com who will be able to resolve this issue for you.
  3. You will have a choice of replacement or refund of the problem items.(damaged, defective or incorrect)
  4. Once Customer Care Team confirms that you will be refunded, you should receive the refund within 10 to 12 working days.
  5. If you are only requesting a refund of one book from a multiple order, then we will refund you the appropriate single item.
  6. Where the items were shipped under a free shipping offer, there will be no shipping costs to refund.

On the off chance your printed book arrives damaged, with book material defect, contact our Customer Relation Team on customercare@packt.com within 14 days of receipt of the book with appropriate evidence of damage and we will work with you to secure a replacement copy, if necessary. Please note that each printed book you order from us is individually made by Packt's professional book-printing partner which is on a print-on-demand basis.

What tax is charged? Chevron down icon Chevron up icon

Currently, no tax is charged on the purchase of any print book (subject to change based on the laws and regulations). A localized VAT fee is charged only to our European and UK customers on eBooks, Video and subscriptions that they buy. GST is charged to Indian customers for eBooks and video purchases.

What payment methods can I use? Chevron down icon Chevron up icon

You can pay with the following card types:

  1. Visa Debit
  2. Visa Credit
  3. MasterCard
  4. PayPal
What is the delivery time and cost of print books? Chevron down icon Chevron up icon

Shipping Details

USA:

'

Economy: Delivery to most addresses in the US within 10-15 business days

Premium: Trackable Delivery to most addresses in the US within 3-8 business days

UK:

Economy: Delivery to most addresses in the U.K. within 7-9 business days.
Shipments are not trackable

Premium: Trackable delivery to most addresses in the U.K. within 3-4 business days!
Add one extra business day for deliveries to Northern Ireland and Scottish Highlands and islands

EU:

Premium: Trackable delivery to most EU destinations within 4-9 business days.

Australia:

Economy: Can deliver to P. O. Boxes and private residences.
Trackable service with delivery to addresses in Australia only.
Delivery time ranges from 7-9 business days for VIC and 8-10 business days for Interstate metro
Delivery time is up to 15 business days for remote areas of WA, NT & QLD.

Premium: Delivery to addresses in Australia only
Trackable delivery to most P. O. Boxes and private residences in Australia within 4-5 days based on the distance to a destination following dispatch.

India:

Premium: Delivery to most Indian addresses within 5-6 business days

Rest of the World:

Premium: Countries in the American continent: Trackable delivery to most countries within 4-7 business days

Asia:

Premium: Delivery to most Asian addresses within 5-9 business days

Disclaimer:
All orders received before 5 PM U.K time would start printing from the next business day. So the estimated delivery times start from the next day as well. Orders received after 5 PM U.K time (in our internal systems) on a business day or anytime on the weekend will begin printing the second to next business day. For example, an order placed at 11 AM today will begin printing tomorrow, whereas an order placed at 9 PM tonight will begin printing the day after tomorrow.


Unfortunately, due to several restrictions, we are unable to ship to the following countries:

  1. Afghanistan
  2. American Samoa
  3. Belarus
  4. Brunei Darussalam
  5. Central African Republic
  6. The Democratic Republic of Congo
  7. Eritrea
  8. Guinea-bissau
  9. Iran
  10. Lebanon
  11. Libiya Arab Jamahriya
  12. Somalia
  13. Sudan
  14. Russian Federation
  15. Syrian Arab Republic
  16. Ukraine
  17. Venezuela