Document:

EX-10.9

 

Exhibit 10.9

J.P. MORGAN CHASE & CO.

STOCK OPTION PLAN

Effective January 18, 2001

Purposes.

The purposes of the J. P. Morgan Chase & Co. Stock Option Plan (the “Plan”) are to encourage key
employees of the Company to acquire a proprietary and vested interest in the growth and performance
of the Company, to retain their services, and to generate an increased incentive to contribute to
the Company’s future success and prosperity, thus enhancing the value of the Company for the
benefit of stockholders.

The purposes of the Plan are to be achieved through grants of stock options to be awarded to
Employees of the Company.

Article 1. Definitions.

For purposes of the Plan, the following terms shall have the meanings set forth below:

1.1 “Award” shall mean a stock option or stock appreciation right granted pursuant to the Plan.

1.2 “Board” shall mean the Board of Directors of the Corporation; provided that any action
taken by a duly authorized committee of the Board within the scope of authority delegated to such
committee by the Board shall be considered an action of the Board for purposes of this Plan.

1.3 “Code” shall mean the Internal Revenue Code of 1986, as from time to time amended.

1.4 “Committee” shall mean the Compensation and Management Development Committee of the Board or
any subcommittee thereof or any other Committee of the Board or subcommittee thereof performing
substantially similar duties.

1.5 “Common Stock” shall mean the common stock of the Corporation, $1 par value.

	 	6.	 	“Company” shall mean the Corporation and its Subsidiaries.

1.7
“Corporation” shall mean J. P. Morgan Chase & Co., and, except as otherwise specified in this
Plan in a particular context, any successor thereto, whether by merger, consolidation, purchase of
all or substantially all its assets or otherwise.

 

 

1.8 “Employee” shall mean any employee of the Company who is receiving compensation for services
rendered to the Company as an employee. By way of clarification, individuals who are not classified
as employees of the Company for purposes of the Company’s human resources information and payroll
systems on the actual date of an Award, including, without limitation, individuals employed by
temporary help firms or other staffing firms or who are treated as independent contractors by the
Company (whether or not deemed to be common law employees or leased employees), are not
“Employees.” In addition, in the event that any individual is re-classified as an employee for any
purpose by any action of any third party or as a result of any lawsuit, action or administrative
proceeding, such individual shall not be deemed an “Employee” under the Plan.

1.9 “Executive Officer” shall mean an Employee who is subject to the requirements of Sections 16(a)
and 16(b) of the Securities Exchange Act of 1934.

1.10 “Fair Market Value” shall mean, for each share of Common Stock, the average of high and low
sale prices of the Common Stock as reported on the New York Stock Exchange (the “NYSE”) composite
tape on the applicable date, or, if there are no such sale prices of Common Stock reported on the
NYSE composite tape on such date, then the average price of the Common Stock on the last previous
day on which high and low sale prices are reported on the NYSE composite tape; provided that
notwithstanding the foregoing, the Committee can select such other method of establishing “Fair
Market Value” as it deems reasonable and appropriate.

1.11 “Participant” shall mean an Employee who is selected by the Committee or its designatee to
receive an Award under the Plan; provided that no Award may be made to any Employee who is
an Executive Officer on the date of grant.

1.12 “Subsidiary” shall mean any corporation which at the time qualifies as a subsidiary of the
Corporation under the definition of “subsidiary corporation” in Section 424(f) of the Code, as
amended from time to time.

	 	13.	 	“Total Disability” shall mean a physical or mental incapacity, which would entitle the
individual to benefits under the long term disability program sponsored by a Subsidiary
employing such individual; provided that if an individual has not elected coverage
under the applicable program, the Committee shall determine, utilizing the criteria of such
program, whether the individual has incurred a Total Disability.

Article 2. Shares Subject to the Plan.

2.1 Shares of Common Stock which may be issued under the Plan may be authorized and unissued shares
of Common Stock or authorized and issued shares of Common Stock held in Treasury. Subject to
adjustment as provided in Article 10, the number of shares of Common Stock that may be granted
under the Plan shall be the number specified by the Committee from time to time.

 

 

Article 3. Award Dates; Eligibility.

	 	1.	 	Awards may be made on such dates as the Committee specifies.

3.2 The Committee shall designate the Employees eligible for an Award hereunder and number of
options awarded each such individual who shall be a Participant following delivery of the Award
agreement; provided that, the Committee may designate that the Director Human Resources or
other officers of the Corporation shall determine the Employee who are to be recipients of Awards
and the number of options to be awarded hereunder; provided that the Committee or its
designatee may specify different levels of Awards for different Employees; provided,
further, that no Executive Officer shall receive an Award under this Plan.

Article 4. Administration.

4.1 The Committee shall administer the Plan. The Committee may operate through subcommittees
established by it, consisting of not fewer than two members of the Committee. The Committee may
delegate any or all of its responsibilities and authorities hereunder to one or more officers or
employees of the Company. The Director Human Resources of the Corporation shall be deemed to have
been delegated all of the Committee’s responsibilities and authorities hereunder until such time,
if any, as the Committee shall determine to withdraw such delegation.

4.2 The Committee is authorized to interpret the Plan, to establish, amend, and rescind any rules
and regulations relating to the Plan, to determine the terms and provisions of any agreements
entered into hereunder, and to make all other determinations necessary or advisable for the
administration of the Plan. The Committee may correct any defect, supply any omission or reconcile
any inconsistency in the Plan or in any Award in the manner and to the extent it shall deem
desirable to carry the Plan or any such Award into effect. The determinations of the Committee or
its designatee in the administration of the Plan, as described herein, shall be final and
conclusive.

4.3 The validity, construction and effect of the Plan and any rules and regulations relating to the
Plan shall be determined in accordance with the laws of the State of New York and applicable laws
of the United States of America.

Article 5. Stock Options.

5.1 Any stock options granted under the Plan shall be in such form as the Committee may from time
to time approve and shall be subject to the terms and conditions provided herein and such
additional terms and conditions, as the Committee shall deem desirable. In particular, the
Committee may establish performance criteria that relate to the exercise of any award.

5.2 Stock options (other than incentive stock options) may be granted to any Participant. The
Committee shall establish the option price at the time each stock option is granted, which price in
the case of a nonqualified stock option shall not be less than 100% of the Fair Market Value of the
Common Stock on the date of grant.

5.3 Stock options under an Award may not be exercisable later than 10 years after their date of
grant. The option price of each share of Common Stock as to which a stock option is exercised shall
be paid in full at the time of such exercise. Such payment may be made at the sole discretion of
the Committee, pursuant to and in accordance with criteria and guidelines established by the
Committee as the same may be modified from time to time, (i) in cash, (ii) by tender of shares of
Common Stock already owned by the Participant, valued at Fair Market Value as of the date of
exercise, (iii) if authorized by the Committee, by withholding pursuant to the election of the
Participant from those shares that would

 

 

otherwise be obtained upon exercise of the option a number
of shares having a Fair Market Value equal to the option price, (iv) if authorized by the
Committee, by delivery of a properly executed exercise notice together with irrevocable
instructions to a securities broker (or, in the case of pledges, lender) approved by the Committee
(or telephonic instructions to the Company, having the same effect) to, (a) sell shares of Common
Stock subject to the option and to deliver promptly to the Corporation a portion of the proceeds of
such sale transaction on behalf of the exercising Participant to pay the option price, or (b)
pledge shares of Common Stock subject to the option to a margin account maintained with a broker or
lender, as security for a loan, and such broker or lender, pursuant to irrevocable instructions,
delivers to the Corporation the loan proceeds, at the time of exercise to pay the option price, or
(v) by any combination of (i), (ii), (iii) or (iv) above.

Article 6. Award Agreements.

6.1 Each Award under the Plan shall be evidenced by an agreement (which agreement need not be
executed by the option holder) setting forth the terms and conditions, as determined by the
Committee, which shall apply to such Award.

Article 7. Withholding.

7.1 The Company shall have the right to deduct from all amounts paid to any Participant in cash
(whether under this Plan or otherwise) any taxes required by law to be withheld therefrom. In the
case of payments of Awards in the form of Common Stock, at the Committee’s discretion the
Participant may be required to pay to the Company the amount of any taxes required to be withheld
with respect to such Common Stock, or, in lieu thereof, the Company shall have the right to retain
the number of shares of Common Stock the Fair Market Value of which equals the amount required to
be withheld. Without limiting the foregoing, the Committee may, in its discretion and subject to
such conditions as it shall impose, permit share withholding to be done at the Participant’s
election.

Article 8. Nontransferability.

8.1 No Award shall be assignable or transferable, and no right or interest of any Participant in
any Award shall be subject to any lien, obligation or liability of the Participant, except as
otherwise set forth in the Award agreement; provided that with respect to Awards, the
Committee may, in its sole discretion, permit certain Participants to transfer Awards to such
individuals or entities as the Committee may specify.

Article 9. No Right to Employment or Continued Participation in Plan.

9.1 No person shall have any claim or right to the grant of an Award prior to the date that an
Award agreement is delivered to such person and the satisfaction of the appropriate formalities
specified in the Award agreement, and the grant of an Award shall not be construed as giving a
Participant the right to be retained in the employ of the Company or to be eligible for any
subsequent Awards. Further, the Company expressly reserves the right to dismiss at any time a
Participant free from any liability or any claim under the Plan, except as provided herein or in
any agreement entered into hereunder.

Article 10. Adjustment of and Changes in Common Stock.

10.1 In the event of any change in the outstanding shares of Common Stock by reason of any stock
dividend or split, recapitalization, issuance of a new class of common stock, merger,
consolidation, spin-off, combination or exchange of shares or other similar corporate change, or
any distributions to

 

 

stockholders of Common Stock other than regular cash dividends, the Committee
may make such substitution or adjustment, if any, as it deems to be equitable, as to the number or
kind of shares of Common Stock or other securities issued or reserved for issuance pursuant to the
Plan, adjustments (including the number of shares and the exercise price) to outstanding Awards.

Article 11. Amendment.

11.1 The Board or the Committee may amend, suspend or terminate the Plan or any portion hereof at
any time.

Article 12. Unfunded Status of Plan.

	 	1.	 	The Plan is intended to constitute an “unfunded” plan for long-term incentive compensation.
Nothing herein shall be construed to give any Participant any rights that are greater than
those of a general unsecured creditor of the Corporation.

Article 13. Non-United States Locations.

13.1 Notwithstanding anything to the contrary in the Plan, the Plan as applied to Employees located
outside the United States and all Awards granted to such Employees shall be subject to applicable
laws, rules, regulations, orders and requirements from time to time in effect in such
jurisdictions, including those that may limit, restrict or prevent such Awards or the exercise of
any Award. The Corporation shall have no obligation to take any action required to comply with any
such laws, rules, regulations, orders or requirements in order to grant any Award to, or to make
any stock option exercisable by, any Employee. Notwithstanding anything herein to the contrary, the
Committee, in its discretion, may issue stock appreciation rights in lieu of options to Employees
located outside the United States when, in the opinion of the Committee, the grant of an option
would be in violation of local law or be administratively burdensome.

Article 14. Effective Date.

14.1 This Plan shall be effective on January 18, 2001.EX-4.1

 

Exhibit 4.1

AMENDED AND RESTATED FIFTH SUPPLEMENTAL INDENTURE

     AMENDED AND RESTATED FIFTH SUPPLEMENTAL INDENTURE (the “Fifth Supplemental
Indenture”), initially dated as of October 6, 2006, as amended and restated as of February 7,
2007, by and among PETROBRAS INTERNATIONAL FINANCE COMPANY, an exempted company incorporated with
limited liability under the laws of the Cayman Islands, having its principal office at
4th Floor, Harbour Place, 103 South Church Street, George Town, Grand Cayman, Cayman
Islands (the “Company”), THE BANK OF NEW YORK, a New York banking corporation, as successor
to JPMorgan Chase Bank, N.A., as Trustee hereunder (the “Trustee”), and PETRóLEO BRASILEIRO
S.A. — PETROBRAS, a mixed capital company (sociedade de economia mista) organized under the laws
of Brazil, having its principal office at Avenida República do Chile, 65, 20035-900 Rio de Janeiro
— RJ, Brazil (“Petrobras”).

WITNESSETH:

     WHEREAS, the Company and the Trustee previously have entered into an indenture, dated as of
July 19, 2002 (the “Original Indenture”, and as supplemented by this amended and restated
Fifth Supplemental Indenture and any further supplements thereto, the “Indenture”),
providing for the issuance from time to time of secured or unsecured debentures, notes or other
evidences of indebtedness of the Company to be issued in one or more series as provided in the
Indenture;

     WHEREAS, Section 9.01 of the Indenture provides that, subsequent to the execution of the
Original Indenture and subject to satisfaction of certain conditions, the Company and the Trustee
may enter into one or more indentures supplemental to the Original Indenture to add to, change or
eliminate any of the provisions of the Indenture in respect of one or more series of Securities (as
defined in the Indenture);

     WHEREAS, the Company issued pursuant to its Registration Statement on Form F-3 (File No.
333-118644) (the “Registration Statement”), originally dated August 30, 2004 and as amended
on September 7, 2004, November 8, 2004 and July 15, 2005, the Prospectus Supplement dated September
29, 2006 and related Base Prospectus dated July 28, 2005 (collectively, the “Offering
Document”) and the Indenture, U.S. $500,000,000 of its 6.125% Global Notes due 2016 (the
“Original Notes”), having the terms and conditions contemplated in the Offering Document as
provided for in the Original Indenture, as supplemented by the fifth supplemental indenture dated
October 6, 2006 (the “Original Fifth Supplemental Indenture”);

     WHEREAS, the Company has duly authorized the execution and delivery of this amendment and
restatement of the Original Fifth Supplemental Indenture, to supplement the Original Indenture and
provide for the issuance of an additional U.S. $399,053,000 principal amount of 6.125% Global
Notes due 2016 in the form attached as Exhibit A hereto (the “Re-Opening Notes” and,
together with the Original Notes, the “Notes”) in connection with an exchange offer for up
to $500,000,000 aggregate principal amount of the series of notes listed in Schedule A to the
Dealer Manager Agreement dated as of January 4, 2007 between the Company and Petrobras and UBS
Securities LLC and Morgan Stanley & Co., Incorporated, as dealer managers, having terms and
conditions contemplated in the Exchange Offering Document and the Indenture;

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     WHEREAS, as contemplated in the Offering Document, Petrobras and the Trustee intend, in
connection with the issuance of the Notes, to (i) enter into an Amended and Restated Standby
Purchase Agreement, dated as of the date hereof in the form attached as Exhibit B hereto (the
“Standby Purchase Agreement”), to provide the holders of the Notes (the “Holders”)
with assurances that, if the Company shall fail to make all required payments of principal,
interest or other amounts due in respect of the Notes and the Indenture, Petrobras will purchase
the rights of the Holders to receive such amounts in consideration of the payment by Petrobras of
an amount of funds equal to the amounts then owed under the Indenture and the Notes, subject to the
provisions thereof and (ii) grant Holders of the Notes direct rights against Petrobras in respect
of the Standby Purchase Agreement by Petrobras being a party to the Indenture as provided herein;

     WHEREAS, the Trustee has provided to the Company and Petrobras Statements of Eligibility under
the Trust Indenture Act of 1939, as amended, with respect to each of the Companies which have been
filed as exhibits to the Registration Statement;

     WHEREAS, any and all conditions and requirements necessary to make this Fifth Supplemental
Indenture a valid, binding, and legal instrument in accordance with the terms of the Indenture have
been performed and fulfilled and the execution and delivery of this Fifth Supplemental Indenture
have been in all respects duly authorized;

     WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee is authorized to execute and
deliver this Fifth Supplemental Indenture; and

     WHEREAS, the Company and Petrobras have requested that the Trustee execute and deliver this
Fifth Supplemental Indenture;

     NOW, THEREFORE, for and in consideration of the premises and the mutual covenants contained
herein and in the Indenture and for other good and valuable consideration, the receipt and
sufficiency of which are herein acknowledged, the Company, Petrobras and the Trustee hereby agree,
for the equal and ratable benefit of all Holders, as follows:

ARTICLE 1

DEFINITIONS

     Section 1.01. Defined Terms. All capitalized terms used but not defined herein shall have the
meanings ascribed to such terms in the Indenture, as supplemented and amended hereby. All
definitions in the Original Indenture shall be read in a manner consistent with the terms of this
Fifth Supplemental Indenture.

     Section 1.02. Additional Definitions. (a) For the benefit of the Holders of the Notes,
Section 1.01 of the Original Indenture shall be amended by adding the following new definitions:

“Closing Date” means February 7, 2007.

“Comparable Treasury Issue” means the United States Treasury security or securities
selected by an Independent Investment Banker as having an actual or

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interpolated maturity comparable to the remaining term of Notes to be redeemed that
would be utilized, at the time of selection and in accordance with customary
financial practice, in pricing new issues of corporate debt securities of a
comparable maturity to the remaining term of such Notes.

“Comparable Treasury Price” means, with respect to any Redemption Date, (1) the
average of the Reference Treasury Dealer Quotations for such Redemption Date, after
excluding the highest and lowest such Reference Treasury Dealer Quotation or (2) if
the Trustee obtains fewer than four such Reference Treasury Dealer Quotations, the
average of all such quotations.

“Default Rate” has the meaning set forth in Section 2.01(f) herein.

“Denomination Currency” has the meaning set forth in Section 2.04(e) herein.

          “Independent Investment Banker” means one of the Reference Treasury Dealers appointed by the
Company.

          “Interest Period” means the period beginning on an Interest Payment Date and ending on the day
before the next Interest Payment Date, except that the first Interest Period shall be the period
beginning on the Original Closing Date and ending on the day before the next Interest Payment Date.

          “Judgment Currency” has the meaning set forth in Section 2.04(e) herein.

          “Lien” means any mortgage, pledge, lien, hypothecation, security interest or other charge or
encumbrance on any property or asset, including, without limitation, any equivalent created or
arising under applicable Law.

          “Make Whole Amount” has the meaning set forth in Section 2.01(k) herein.

          “Material Subsidiary” means, as to any Person, any Subsidiary of such Person which, on any
given date of determination, accounts for more than 10% of Petrobras’ total consolidated assets, as
such total assets are set forth on the most recent consolidated financial statements of Petrobras
prepared in accordance with U.S. GAAP (or if Petrobras does not prepare financial statements in
U.S. GAAP, consolidated financial statements prepared in accordance with Brazilian generally
accepted accounting principles).

          “Offering Document” shall have the meaning set forth in the recitals to the Fifth Supplemental
Indenture.

          “Original Closing Date” means October 6, 2006.

          “Payment Account” has the meaning set forth in Section 2.01(g) herein.

          “Permitted Lien” means a:

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     (a) Lien arising by operation of law, such as merchants’, maritime or other similar
Liens arising in the Company’s ordinary course of business or that of any Subsidiary or Lien
in respect of taxes, assessments or other governmental charges that are not yet delinquent
or that are being contested in good faith by appropriate proceedings;

     (b) Lien arising from the Company’s obligations under performance bonds or surety
bonds and appeal bonds or similar obligations incurred in the ordinary course of business
and consistent with the Company’s past practice;

     (c) Lien arising in the ordinary course of business in connection with Indebtedness
maturing not more than one year after the date on which such Indebtedness was originally
incurred and which is related to the financing of export, import or other trade
transactions;

     (d) Lien granted upon or with respect to any assets hereafter acquired by the Company
or any Subsidiary to secure the acquisition costs of such assets or to secure Indebtedness
incurred solely for the purpose of financing the acquisition of such assets, including any
Lien existing at the time of the acquisition of such assets as long as the maximum amount so
secured shall not exceed the aggregate acquisition costs of all such assets or the aggregate
Indebtedness incurred solely for the acquisition of such assets, as the case may be;

     (e) Lien granted in connection with the Indebtedness of a Wholly-Owned Subsidiary
owing to the Company or another Wholly-Owned Subsidiary;

     (f) Lien existing on any asset or on any stock of any Subsidiary prior to the
acquisition thereof by the Company or any Subsidiary as long as such Lien is not created in
anticipation of such acquisition;

     (g) Lien existing as of the date of the Indenture;

     (h) Lien resulting from the Transaction Documents;

     (i) Lien incurred in connection with the issuance of debt or similar securities of a
type comparable to those already issued by the Company, on amounts of cash or cash
equivalents on deposit in any reserve or similar account to pay interest on such securities
for a period of up to 24 months as required by any Rating Agency as a condition to such
Rating Agency rating such securities investment grade or as is otherwise consistent with
market conditions at such time, as such conditions are satisfactorily demonstrated to the
Trustee;

     (j) Lien granted or incurred to secure any extension, renewal, refinancing, refunding
or exchange (or successive extensions, renewals, refinancings, refundings or exchanges), in
whole or in part, of or for any Indebtedness secured by Lien referred to in paragraphs (a)
through (i) above (but not paragraph (c)), provided that such Lien does not extend to any
other property, the principal amount of the Indebtedness secured by such Lien is not
increased, and in the case of paragraphs (a), (b) and (c), the obligees meet the
requirements of such paragraphs; and

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     (k) Lien in respect of Indebtedness the principal amount of which in the aggregate, together
with all Liens not otherwise qualifying as the Company’s Permitted Liens pursuant to clauses (a)
through (j) of this definition, does not exceed 15% of the Company’s consolidated total assets (as
determined in accordance with U.S. GAAP) at any date as at which the Company’s balance sheet is
prepared and published in accordance with applicable Law.

          “Reference Treasury Dealer” means each of UBS Securities LLC and Morgan Stanley & Co.
Incorporated or their affiliates which are primary United States government securities dealers and
two other leading primary United States government securities dealers in New York City reasonably
designated by the Company; provided, however, that if any of the foregoing shall cease to be a
primary United States government securities dealer in New York City (a “Primary Treasury Dealer”),
the Company shall substitute therefore another Primary Treasury Dealer.

          “Reference Treasury Dealer Quotation” means, with respect to each Reference Treasury Dealer
and any Redemption Date, the average, as determined by the Trustee, of the bid and asked prices for
the Comparable Treasury Issue (expressed in each case as a percentage of its principal amount)
quoted in writing to the Trustee by such Reference Treasury Dealer at 3:30 pm New York time on the
third business day preceding such redemption date.

          “Taxing Jurisdiction” shall mean, Brazil, the jurisdiction of the Company’s incorporation or
any other jurisdiction in which the Company appoints a paying agent hereunder or any political
subdivision or any taxing authority thereof or therein.

          “Treasury Rate” means, with respect to any Redemption Date, the rate per annum equal to the
semiannual equivalent yield to maturity or interpolated maturity (on a day count basis) of the
Comparable Treasury Issue, assuming a price for the Comparable Treasury Issue (expressed as a
percentage of its principal amount) equal to the Comparable Treasury Price for such Redemption
Date.

ARTICLE 2

TERMS OF THE NOTES

     Section 2.01. General. In accordance with Section 3.01 of the Original Indenture, the
following terms relating to the Notes are hereby established:

          (a) Title: The Notes shall constitute a series of Securities having the title “6.125% Global
Notes due 2016.”

          (b) Aggregate Amount: The aggregate principal amount of the Notes that may be initially
authenticated and delivered under the Fifth Supplemental Indenture shall be U.S.$899,053,000. As
provided in the Original Indenture, the Company may, from time to time, without the consent of the
Holders of Notes, issue Add On Notes having identical terms (including CUSIP, ISSN and other
relevant identifying characteristics as the Notes), so long as, on the date of issuance of such Add
On Notes: (i) no Default or Event of Default shall have occurred and then be continuing, or shall
occur as a result of the issuance of such Add On Notes,

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(ii) such Add On Notes shall rank pari passu with the Notes and shall have identical terms,
conditions and benefits as the Notes and be part of the same series as the Notes, (iii) the Company
and the Trustee shall have executed and delivered a further supplemental indenture to the Indenture
providing for the issuance of such Add On Notes and reflecting such amendments to the Indenture as
may be required to reflect the increase in the aggregate principal amount of the Notes resulting
from the issuance of the Add On Notes, (iv) Petrobras and the Trustee shall have executed and
delivered an amended Standby Purchase Agreement reflecting the increase in the aggregate principal
amount of the Notes resulting from the issuance of the Add On Notes and (v) the Trustee shall have
received all such opinions and other documents as it shall have requested, including an Opinion of
Counsel stating that such Add On Notes are authorized and permitted by the Indenture and all
conditions precedent to the issuance of such Add On Notes have been complied with by the Company
and Petrobras. All Add On Notes issued hereunder will, when issued, be considered Notes for all
purposes hereunder and will be subject to and take the benefit of all of the terms, conditions and
provisions of this Indenture.

          (c) Ranking: The Notes (including the Add On Notes) shall be general senior unsecured and
unsubordinated obligations of the Company and shall at all times rank pari passu among themselves
and at least equal in right of payment with all of the Company’s other present and future unsecured
and unsubordinated obligations from time to time outstanding that are not, by their terms,
expressly subordinated in right of payment to the Notes.

          (d) Maturity: The entire outstanding principal of the Notes shall be payable in a single
installment on October 6, 2016 (the “Stated Maturity”). No payments in respect of the
principal of the Notes shall be paid prior to the Stated Maturity except in the case of the
occurrence of an Event of Default and acceleration of the aggregate outstanding principal amount of
the Notes, upon redemption prior to the Stated Maturity pursuant to Section 11.08 of the Indenture
or pursuant to Sections 2.01(k) and 2.01(l) hereof.

          (e) Interest: Interest shall accrue on the Notes at the rate of 6.125% per annum from the
Original Closing Date until all required amounts due in respect of the Notes have been paid. All
interest shall be paid by the Company to the Trustee and distributed by the Trustee in accordance
with this Indenture semiannually in arrears on April 6 and October 6 of each year (or, as provided
in the Original Indenture, if such date is not a Business Day, the next succeeding Business Day
following such day) during which any portion of the Notes shall be Outstanding (each, an
“Interest Payment Date”), commencing on April 6, 2007, to the Person in whose name a Note
is registered at the close of business on the preceding Regular Record Date (which shall mean, with
respect to any payment to be made on an Interest Payment Date, the Business Day that is ten
Business Days prior to such Interest Payment Date.) As provided in the Original Indenture, (i)
interest shall be calculated based on a 360-day year of twelve 30-day months, (ii) payment of
principal and interest and other amounts on the Notes will be made at the Corporate Trust Office of
the Trustee in New York City, or such other paying agent office in the United States as the Company
appoints, in the form provided for in Section 10.17 of the Indenture, (iii) all such payments to
the Trustee shall be made by the Company by depositing immediately available funds in U.S. dollars
one Business Day prior to the relevant Interest Payment Date to the Payment Account and (iv) so
long as any of the Notes remain Outstanding, the Company shall maintain a paying agent in New York
City.

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          (f) Default Rate: Upon the occurrence and during the continuation of an Event of Default, (i)
interest on the outstanding principal amount of the Notes shall accrue on the Notes at a rate equal
to 1.0% per annum above the interest rate on the Notes at that time (the “Default Rate”)
and (ii) to the fullest extent permitted by law, interest shall accrue on the amount of any
interest, fee, Additional Amounts, or other amount payable under the Indenture and the Notes that
is not paid when due, from the date such amount was due until such amount shall be paid in full,
excluding the date of such payment, at the Default Rate.

          (g) Payment Account: On the Original Closing Date, the Trustee established (and promptly
notified the Company of the establishment of such account, including the relevant account numbers
and other relevant identifying details) and, until the Notes and all accounts due in respect
thereof have been paid in full, shall maintain a special purpose non-interest bearing trust account
(the “Payment Account”) into which all payments required to be made by the Company under or
with respect to the Notes shall be deposited. The Company agrees that the Payment Account shall be
maintained in the name of the Trustee and under its sole dominion and control (acting on behalf of
the Holders of the Notes) and used solely to make payments of principal, interest and other amounts
from time to time due and owing on, or with respect to, the Notes. No funds contained in the
Payment Account shall be used for any other purpose or in any manner not expressly provided for
herein nor shall the Company or any other Person have an interest therein or amounts on deposit
therein. All amounts on deposit in the Payment Account on any Interest Payment Date after the
Trustee has paid all amounts due and owing to the holders of the Notes as of such Interest Payment
Date shall be retained in the Payment Account and used by the Trustee to pay any amounts due and
owing to the Holders of the Notes on the next succeeding Interest Payment Date.

          (h) Form and Denomination: The Notes shall be issuable in whole in the registered form of one
or more Global Notes (without coupons), in minimum denominations of U.S.$2,000 and integral
multiples of U.S.$1,000 in excess thereof, and shall be transferable in integral multiples of
U.S.$2,000 and integral multiples of U.S.$1,000 in excess thereof and the Depository for such
Global Notes shall be The Depository Trust Company, New York, New York.

          (i) Standby Purchase Agreement: The Notes shall have the benefit of the Standby Purchase
Agreement in the manner provided in Article 3 of this Fifth Supplemental Indenture.

          (j) Rating: The Notes can be issued without the requirement that they have any rating from a
nationally recognized statistical rating organization.

          (k) Optional Early Redemption: The Notes are subject to redemption at the Company’s option
before the Stated Maturity in whole or in part, upon not less than 30 but no more than 60 days’
notice, at a redemption price equal to the greater of (A) 100% of the principal amount of such
Notes and (B) the sum of the present values of the remaining scheduled payments of principal and
interest thereon (exclusive of interest accrued to the date of redemption) discounted to the
Redemption Date on a semiannual basis (assuming a 360-day year consisting of twelve 30-day months)
at, in each case, the Treasury Rate plus 25 basis points (the

7

 

“Make Whole Amount”), plus in each case, accrued interest on the principal amount of such
Notes to (but not including) the date of redemption.

          (l) Early Redemption Solely for Tax Reasons. Pursuant to Section 11.08 of the Original
Indenture, the Notes may be redeemed at the option of the Company, in whole but not in part, at any
time at a Redemption Price equal to the principal amount thereof plus accrued interest to the date
fixed for redemption if as a result of any change in or amendment to the laws or regulations or
ruling promulgated thereunder of the jurisdiction in which the Company is incorporated (or, in the
case of a successor Person to the Company, of the jurisdiction in which such successor Person is
organized or any political subdivision or taxing authority thereof or therein) or any change in the
official application or interpretation of such laws, regulations or rulings, or any change in the
official application of or interpretation of, or any execution of or amendment to, any treaty or
treaties affecting taxation to which such jurisdiction or such political subdivision or taxing
authority (or such other jurisdiction or political subdivision or taxing authority) is a party,
which change, execution or amendment becomes effective on or after the date specified pursuant to
the terms of Section 3.01 of the Original Indenture (or in the case of a successor Person to the
Company, the date on which such successor Person became such pursuant to Section 8.01 and 8.02 of
the Original Indenture). For purposes of Section 11.08 of the Original Indenture, the
reincorporation of the Company shall be treated as the adoption of a successor entity, provided,
however, that redemption under Section 11.08 of the Original Indenture shall not be available if
the reincorporation was performed in anticipation of a change in, execution of or amendment to any
laws or treaties or the official application or interpretation of any laws or treaties of such new
jurisdiction of incorporation that would result in an obligation to pay Additional Amounts.

          (m) Conversion: The Notes will not be convertible into, or exchangeable for, any other
securities.

     Section 2.02. Amendments to Article Five Relating to Events of Default. (a) Restated
Events of Default: As it applies to the Notes, Section 5.01 of the Original Indenture shall be
amended to read in its entirety as follows:

          “Section 5.01 Events of Default

     “Event of Default,” wherever used herein with respect to the Notes, means any one of
the following events (whatever the reason for such Event of Default and whether it shall be
voluntary or involuntary or be effected by operation of law or pursuant to any judgment,
decree or order of any court or any order, rule or regulation of any administrative or
governmental body):

     1. The Company shall fail to make any payment in respect of principal on any of the
Notes whether on the Stated Maturity, upon redemption or prior to the Maturity or otherwise
in accordance with the terms of the Notes and this Indenture, non-payment of which shall
continue for a period of three calendar days and the Trustee shall not have otherwise
received such amounts from Petrobras under the Standby Purchase Agreement, or otherwise by
the end of such three calendar day period;

8

 

     2. The Company shall fail to make any payment in respect of any interest or other
amounts due on or with respect to the Notes (including Additional Amounts, if any) in
accordance with the terms of the Notes and this Indenture, non-payment of which shall
continue for a period of 30 calendar days and the Trustee shall not have otherwise received
such amounts from Petrobras under the Standby Purchase Agreement, or otherwise by the end of
such 30 calendar day period;

     3. The Company or Petrobras shall fail to perform, or breach, any term, covenant,
agreement or obligation contained in this Indenture or the Standby Purchase Agreement and
such failure (other than any failure to make any payment under the Standby Purchase
Agreement, for which there is no cure) is either incapable of remedy or continues for a
period of 60 calendar days (inclusive of any time frame contained in any such term,
covenant, agreement or obligation for compliance thereunder) after there has been received
by the Company or Petrobras from the Trustee or the Holders of at least 25% in principal
amount of the Outstanding Securities of that series a written notice specifying such default
or breach and requiring it to be remedied and stating that such notice is a “Notice of
Default” hereunder;

     4. The maturity of any Indebtedness of the Company, Petrobras or any Material
Subsidiary in a total aggregate principal amount of U.S.$100,000,000 or more is accelerated
in accordance with the terms of that Indebtedness, it being understood that prepayment or
redemption by the Company, Petrobras or the relevant Material Subsidiary of any Indebtedness
is not acceleration for this purpose;

     5. One or more final and non-appealable judgments or final decrees is entered against
the Company, Petrobras or any Material Subsidiary thereof involving in the aggregate a
liability (not theretofore paid or covered by insurance) of U.S.$100,000,000 (or its
equivalent in another currency) or more, and all such judgments or final decrees shall not
have been vacated, discharged or stayed within 120 calendar days after the rendering
thereof;

     6. The Company, Petrobras or any Material Subsidiary thereof stops payment of, or is
generally unable to pay, its debts as and when they become due except (i) as is otherwise
expressly provided under this Indenture or the Standby Purchase Agreement, or (ii) in the
case of a winding-up, dissolution or liquidation for the purpose of and followed by a
consolidation, merger, conveyance or transfer, the terms of which shall have been approved
by a resolution of a meeting of the Holders;

     7. Proceedings are initiated against the Company, Petrobras or any Material Subsidiary
thereof under any applicable bankruptcy, reorganization, insolvency, moratorium or
intervention law or law with similar effect, or under any other law for the relief of, or
relating to, debtors, and any such proceeding is not dismissed or stayed within 90 days
after the entering of such proceeding, or an administrator, receiver, trustee, manager,
fiduciary, statutory manager, intervener or assignee for the benefit of creditors (or other
similar official) is appointed to take possession or control of, or a distress, execution,
attachment or sequestration or other process is levied, enforced upon, sued out or put in
force against, all or any material part of the undertaking, property,

9

 

assets or revenues of the Company, Petrobras or any Material Subsidiary thereof and is
not discharged or removed within 90 days;

     8. The Company, Petrobras or any Material Subsidiary thereof commences voluntarily or
consents to judicial, administrative or other proceedings relating to it under any
applicable bankruptcy, reorganization, insolvency, moratorium or intervention law or law
with similar effect, or under any other law for the relief of, or relating to, debtors, or
makes or enters into any composition, concordata or other similar arrangement with its
creditors, or appoints or applies for the appointment of an administrator, receiver,
trustee, manager, fiduciary, statutory manager, intervener or assignee for the benefit of
creditors (or other similar official) to take possession or control of the whole or any
material part of its undertaking, property, assets or revenues, or takes any judicial,
administrative or other similar proceeding under any law for a readjustment or deferment of
its Indebtedness or any part of it;

     9. An effective resolution is passed for, or any authorized action is taken by any
court of competent jurisdiction, directing the winding-up, dissolution or liquidation of the
Company, Petrobras or any Material Subsidiary thereof (other than in any of the
circumstances referred to as exceptions in paragraph (6) above);

     10. Any event occurs that under the laws of any relevant jurisdiction has substantially
the same effect as any of the events referred to in any of paragraphs (6), (7), (8) or (9)
of this Section 5.01;

     11. This Indenture, the Notes, the Standby Purchase Agreement or any part thereof shall
cease to be in full force and effect or binding and enforceable against the Company or
Petrobras, it becomes unlawful for the Company or Petrobras to perform any material
obligation under this Indenture, the Notes or the Standby Purchase Agreement, or the Company
or Petrobras shall contest the enforceability of this Indenture, the Notes or the Standby
Purchase Agreement or deny that it has liability under this Indenture, the Notes or the
Standby Purchase Agreement;

     12. Petrobras fails to retain at least 51% direct or indirect ownership of the
outstanding voting and economic interests (equity or otherwise) of and in the Company.”

     Section 2.03. Amendments to Article 8.01 Relating to Consolidation, Merger, Conveyance,
Transfer of Lease. (a) As it applies to the Notes, Section 8.01 of the Original Indenture shall be
amended to read in its entirety as follows:

          “Section 8.01 Limitation on Consolidation, Merger, Sale or Conveyance.

          (a) The Company will not, in one or a series of transactions, consolidate or
amalgamate with or merge into any corporation or convey, lease or transfer substantially all
of its properties, assets or revenues to any person or entity (other than a direct or
indirect Subsidiary of Petrobras) or permit any person (other than a direct or indirect
Subsidiary of the Company) to merge with or into it unless:

10

 

     (1) either the Company is the continuing entity or the Person (the “Successor
Company”) formed by the consolidation or into which the Company is merged or that acquired
or leased the property or assets of the Company will assume (jointly and severally with the
Company unless the Company will have ceased to exist as a result of that merger,
consolidation or amalgamation), by a supplemental indenture (the form and substance of which
will be previously approved by the Trustee), all of the Company’s obligations under the
Indenture and the Notes;

     (2) the Successor Company (jointly and severally with the Company unless the Company
will have ceased to exist as part of the merger, consolidation or amalgamation) agrees to
indemnify each Holder against any tax, assessment or governmental charge thereafter imposed
on the Holder solely as a consequence of the consolidation, merger, conveyance, transfer or
lease with respect to the payment of principal of, or interest, the Notes;

     (3) immediately after giving effect to the transaction, no Event of Default, and no
Default has occurred and is continuing;

     (4) the Company has delivered to the Trustee an Officers’ Certificate and an
Opinion of Counsel, each stating that the transaction and the fifth supplemental
indenture, comply with the terms of the Indenture and that all conditions precedent
provided for in the Indenture and relating to the transaction have been complied with; and

     (5) the Company must deliver a notice describing that transaction to Moody’s to the
extent that Moody’s is at that time rating the Notes.

     Notwithstanding anything to the contrary in the foregoing, so long as no Default
or Event of Default under the Indenture or the Notes will have occurred and be continuing
at the time of the proposed transaction or would result from the transaction:

     (6) the Company may merge, amalgamate or consolidate with or into, or convey,
transfer, lease or otherwise dispose of all or substantially all of its properties, assets
or revenues to a direct or indirect Subsidiary of the Company or Petrobras in cases when
the Company is the surviving entity in the transaction and the transaction would not have
a material adverse effect on the Company and its Subsidiaries taken as a whole, it being
understood that if the Company is not the surviving entity, the Company will be required
to comply with the requirements set forth in the previous paragraph; or

     (7) any direct or indirect Subsidiary of the Company may merge or consolidate with or
into, or convey, transfer, lease or otherwise dispose of assets to, any person (other than
the Company or any of its subsidiaries or affiliates) in cases when the transaction would
not have a material adverse effect on the Company and its subsidiaries taken as a whole;
or

11

 

     (8) any direct or indirect Subsidiary of the Company may merge or consolidate with or
into, or convey, transfer, lease or otherwise dispose of assets to, any other direct or
indirect Subsidiary of the Company or Petrobras; or

     (9) any direct or indirect Subsidiary of the Company may liquidate or dissolve if the
Company determines in good faith that the liquidation or dissolution is in the best
interests of Petrobras, and would not result in a material adverse effect on the Company
and its Subsidiaries taken as a whole and if the liquidation or dissolution is part of a
corporate reorganization of the Company or Petrobras.”

     Section 2.04. Amendments to Article 10 Relating to Covenants. (a) Use of Proceeds:
As it applies to the Notes, Section 10.12 of the Original Indenture shall be amended to read in its
entirety as follows:

          “Section 10.12 Use of Proceeds.

     The Company will use the proceeds from the offer and sale of the Notes after the
deduction of any commissions principally for general corporate purposes, including the
financing of the purchase of oil product imports and the repayment of existing trade-related
debt and intercompany loans. The Company may lend a portion of the proceeds to Petrobras.”

          (b) Statement of Officers as to Default and Notices of Events of Default: As it
applies to the Notes, Section 10.13 of the Original Indenture shall be amended by deleting the
second sentence in its entirety and replacing it with the following:

     “Within 10 calendar days (or promptly with respect to Events of Default pursuant to
Sections 5.01(4), 5.01(5), 5.01(6), 5.01(7), 5.01(8), 5.01(9) and 5.01(10) hereunder and in
any event no later than 10 calendar days) after the Company becomes aware or should
reasonably become aware of the occurrence of an Event of Default pursuant to Section 5.01
hereunder, the Company shall provide notice to the Trustee of such occurrence, accompanied by
an Officer’s Certificate of the Company setting forth the details thereof.”

          (c) Provision of Financial Statements and Reports: As it applies to the Notes,
Section 10.14 of the Original Indenture shall be amended by deleting the second paragraph in its
entirety and replacing it with the following:

     “The Company will provide, together with each of the financial statements delivered
pursuant to this Section, an Officer’s Certificate stating (A) that a review of the
Company’s activities has been made during the period covered by such financial statements
with a view to determining whether the Issuer has kept, observed, performed and fulfilled
its covenants and agreements under this Indenture and (B) that no Default or Event of
Default has occurred during such period or, if one or more have actually occurred,
specifying all such events and what actions have been taken and will be taken with respect
to such Event of Default.”

12

 

          (d) Additional Amounts: As it applies to the Notes, Section 10.19 of the Original
Indenture shall be amended by:

     (i) deleting the word “Brazil” throughout such Section 10.19 and replacing it with the
expression “Taxing Jurisdiction” (as defined in Section 1.02 of this Fifth Supplemental Indenture);

     (ii) adding the phrase, “, levies” after the phrase, “deduction or withholding for any present
or future taxes” in the first sentence of such Section 10.19;

     (iii) deleting the phrase, “who, with respect to any such tax, assessment or other
governmental charge, is not resident in Brazil” in the first sentence of such Section 10.19;

     (iv) deleting the proviso to the first sentence of such Section 10.19 that includes clauses
(1)-(7) thereof and ends with the phrase, “who would not have been entitled to such Additional
Amounts had it been the Holder or beneficial owner, as the case may be, of such Security” and
replacing such proviso with the following:

     “; provided, however, that the Company shall not be required to make any payment of
Additional Amounts that is imposed due to any of the following:

     (1) such Holder or the Trustee has a connection with the Taxing Jurisdiction other than
merely holding the Notes or receiving principal or interest payments on the Notes (such as
citizenship, nationality, residence, domicile, or existence of a business, a permanent
establishment, a dependent agent, a place of business or a place of management present or
deemed present within the Taxing Jurisdiction);

     (2) any tax imposed on, or measured by, net income;

     (3) such Holder or the Trustee fails to comply with any certification, identification
or other reporting requirements concerning its nationality, residence, identity or
connection with the Taxing Jurisdiction, if (x) such compliance is required by applicable
law, regulation, administrative practice or treaty as a precondition to exemption from all
or a part of the tax, levy, deduction or other governmental charge, (y) such Holder or the
Trustee is able to comply with such requirements without undue hardship and (z) at least 30
calendar days prior to the first payment date with respect to which such requirements under
the applicable law, regulation, administrative practice or treaty will apply, the Company
has notified all Holders that they will be required to comply with such requirements;

     (4) such Holder or the Trustee fails to present (where presentation is required) its
Note within 30 calendar days after the Company has made available to such Holder or the
Trustee a payment under the Notes and this Indenture, provided that the Company will pay
Additional Amounts which a Holder or the Trustee would have been entitled to had the Note
owned by such Holder or the Trustee been presented on any day (including the last day)
within such 30 calendar day period;

13

 

     (5) any estate, inheritance, gift, value added, use or sales taxes or any similar
taxes, assessments or other governmental charges; or

     (6) such taxes, levies, deductions or other governmental charges are imposed on a
payment on the Notes to an individual and are required to be made pursuant to any European
Union Council Directive implementing the conclusions of the ECOFIN Council meeting of
November 26-27, 2000 on the taxation of savings income, or any law implementing or complying
with, or introduced in order to conform to, such directive;

     (7) where such Holder or the Trustee could have avoided such taxes, levies, deductions
or other governmental charges by requesting that a payment on the Notes be made by, or
presenting the relevant notes for payment to, another paying agent of the Company located in
a member state of the European Union; or

     (8) where the Holder or the Trustee would have been able to avoid the tax, levy,
deduction or other governmental charge by taking reasonable measures available to such
Holder or the Trustee .”

     (v) adding the following new paragraph at the end of Section 10.19:

     “The Company shall promptly pay when due any present or future stamp, court or
documentary taxes or any other excise or property taxes, charges or similar levies that are
imposed by a Taxing Jurisdiction that arise from any payment under the Notes or under any
other document or instrument referred herein or therein or from the execution, delivery,
enforcement or registration of each Note or any other document or instrument referred to
herein or therein. The Company shall indemnify and make whole the Holders of the Notes for
any present or future stamp, court or documentary taxes or any other excise or property
taxes, charges or similar levies payable by the Issuer as provided in this paragraph paid by
such Holder of the Notes. The Company shall, if European Council Directive 2003/48/EC or
any other Directive implementing the conclusions of the ECOFIN council meeting of November
26-27, 2000 is brought into force, ensure that it maintains a paying agent hereunder in a
member state of the European Union that will not be obliged to withhold or deduct tax
pursuant to such Directive.”

          (e) Additional Covenants Applicable to the Notes: As it applies to the Notes, Article
10 of the Original Indenture shall be amended to include the following:

          “Section 10.20 Negative Pledge

     So long as any Note remains Outstanding, the Company will not create or permit any
Lien, other than a Permitted Lien, on any of the Company’s assets to secure (a) any of the
Company’s Indebtedness or (b) the Indebtedness of any other Person, unless the Company
contemporaneously creates or permits such Lien to secure equally and ratably the Company’s
obligations under the Notes and this Indenture or the Company provides such other security
for the Notes as is duly approved by a resolution of the Holders of the Notes in accordance
with this Indenture. In addition, the Company will not allow any of the Company’s
Subsidiaries to create or permit any Lien, other than a Permitted Lien, on any of its assets
to secure (a) any of the Company’s Indebtedness, (b) any of its own

14

 

Indebtedness or (c) the Indebtedness of any other Person, unless it contemporaneously
creates or permits the Lien to secure equally and ratably the Company’s obligations under
the Notes and this Indenture or the Company provides such other security for the Notes as is
duly approved by a resolution of the Holders of the Notes.

     Section 10.21 Currency Rate Indemnity. (a) The Company shall (to the extent
lawful) indemnify the Trustee and the Holders of the Notes and keep them indemnified
against:

     (i) in the case of nonpayment by the Company of any amount due to the Trustee, on
behalf of the Holders of the Notes, under the Indenture any loss or damage incurred by any
of them arising by reason of any variation between the rates of exchange used for the
purposes of calculating the amount due under a judgment or order in respect thereof and
those prevailing at the date of actual payment by the Company; and

     (ii) any deficiency arising or resulting from any variation in rates of exchange
between (i) the date as of which the local currency equivalent of the amounts due or
contingently due under the Indenture or in respect of the Notes is calculated for the
purposes of any bankruptcy, insolvency or liquidation of the Company, and (ii) the final
date for ascertaining the amount of claims in such bankruptcy, insolvency or liquidation.
The amount of such deficiency shall be deemed not to be increased or reduced by any
variation in rates of exchange occurring between the said final date and the date of any
bankruptcy, insolvency or liquidation or any distribution of assets in connection therewith.

     (b) The Company agrees that, if a judgment or order given or made by any court for the
payment of any amount in respect of its obligations hereunder is expressed in a currency
(the “Judgment Currency”) other than U.S. dollars (the “Denomination
Currency”), it will indemnify the relevant Holder against any deficiency arising or
resulting from any variation in rates of exchange between the date at which the amount in
the Denomination Currency is notionally converted into the amount in the Judgment Currency
for the purposes of such judgment or order and the date of actual payment thereof.

     (c) The above indemnities shall constitute separate and independent obligations of the
Company from its obligations under the Indenture, will give rise to separate and independent
causes of action, will apply irrespective of any indulgence granted from time to time and
will continue in full force and effect notwithstanding any judgment or the filing of any
proof or proofs in any bankruptcy, insolvency or liquidation of the Company for a liquidated
sum or sums in respect of amounts due under the Indenture or the Notes.”

          (f) Covenants not Applicable to the Notes. As it applies to the Notes, and no other
outstanding series of notes, Article 10 of the Original Indenture is hereby amended by deleting
sections 10.02, 10.04, 10.05, 10.06, 10.07, 10.08, 10.09 and 10.15 in their entirety.

15

 

     Section 2.05. Application of the Article of the Indenture Regarding Defeasance and Covenant
Defeasance. The provisions of Sections 14.01, 14.02 and 14.03 of the Original Indenture shall
apply to the Notes.

ARTICLE 3

STANDBY PURCHASE AGREEMENT

     Section 3.01. Execution. The Trustee is hereby authorized and directed to execute and deliver
the Standby Purchase Agreement and to perform all of its duties and obligations thereunder.

     Section 3.02. Enforcement. The Trustee shall enforce the provisions of the Standby Purchase
Agreement against Petrobras in accordance with the terms thereof and the terms of the Indenture and
Petrobras, by execution of this Fifth Supplemental Indenture, and by so agreeing to become a party
to the Indenture, agrees that each Holder of the Notes shall have direct rights under the Standby
Purchase Agreement as if it were a party thereto.

     Section 3.03. Petrobras hereby (i) acknowledges and agrees to be bound by the provisions of
Sections 1.08 and 3.14 of the Indenture and (ii) confirms that (A) its obligations under the
Standby Purchase Agreement shall be issued pursuant to the Indenture and (B) it intends for the
Holders of the Notes, in addition to those rights under the Standby Purchase Agreement as provided
therein, to be entitled to the benefits of the Indenture with respect to their rights against
Petrobras under the Standby Purchase Agreement.

     Section 3.04. Definition of the Term “Securities.” For all purposes relating to the Notes,
the term “Securities” in Section 1.01 of the Original Indenture shall be amended by inserting the
following at the end thereof: “All references herein to any Securities shall be deemed to include
the rights of the Holder thereof under any standby purchase agreement or guarantee arrangement
entered into by Petrobras with the Trustee in connection with the issuance of such Securities
pursuant to Section 3.14 hereof, which are an integral part of such Securities.”

ARTICLE 4

MISCELLANEOUS

     Section 4.01. Effect of the Fifth Supplemental Indenture. This Fifth Supplemental Indenture
supplements the Indenture and shall be a part, and subject to all the terms, thereof. The Original
Indenture, as supplemented and amended by this Fifth Supplemental Indenture, is in all respects
ratified and confirmed, and the Original Indenture and this Fifth Supplemental Indenture shall be
read, taken and construed as one and the same instrument. All provisions included in this Fifth
Supplemental Indenture supersede any conflicting provisions included in the Original Indenture
unless not permitted by law. The provisions of this Fifth Supplemental Indenture are intended to
apply solely to the Notes and the Holders thereof and shall not apply to any future issuance of
securities by the Company (other than any Add On Notes as provided herein) and all references to
provisions of the Original Indenture herein amended and restated or otherwise modified shall have
effect solely with respect to the Notes contemplated in this Fifth Supplemental Indenture. The
Trustee accepts the trusts created by the Original Indenture, as

16

 

supplemented by this Fifth Supplemental Indenture, and agrees to perform the same upon the
terms and conditions of the Original Indenture, as supplemented by this Fifth Supplemental
Indenture.

     Section 4.02. Governing Law. This Fifth Supplemental Indenture shall be governed by, and
construed in accordance with, the laws of the State of New York.

     Section 4.03. Trustee Makes No Representation. The Trustee shall not be responsible in any
manner whatsoever for or in respect of the validity or sufficiency of this Fifth Supplemental
Indenture or for or in respect of the recitals contained herein, all of which are made solely by
the Company and Petrobras.

     Section 4.04. Effect of Headings. The section headings herein are for convenience only and
shall not affect the construction of this Fifth Supplemental Indenture.

     Section 4.05. Counterparts. The parties may sign any number of copies of this Fifth
Supplemental Indenture. Each signed copy shall be an original, but all of them shall represent the
same agreement.

[SIGNATURE PAGE TO FOLLOW IMMEDIATELY]

17

 

Exhibit 4.1

          IN WITNESS WHEREOF, the parties have caused this Fifth Supplemental Indenture to be duly
executed by their respective officers thereunto duly authorized as of the day and year first above
written.

	 	 	 	 	 
	 	PETROBRAS INTERNATIONAL FINANCE COMPANY

 	 
	 	By:  	/s/ Theodore M. Helms
 	 
	 	 	Name:  	Theodore M. Helms 	 
	 	 	Title:  	Attorney-In-Fact 	 
	 
	 	PETRÓLEO BRASILEIRO S.A. — PETROBRAS

 	 
	 	By:  	/s/ Theodore M. Helms
 	 
	 	 	Name:  	Theodore M. Helms 	 
	 	 	Title:  	Attorney-In-Fact 	 
	 
	 	WITNESSES:

 	 
	 	1.  	/s/ Jo Dean Adams
 	 
	 	 	Name:  	Jo Dean Adams 	 
	 	 	 	 
	 	2.  	     /s/ Manuel Silva
 	 
	 	 	Name:  	Manuel Silva 	 
	 	 	 	 

1

 

	 	 	 	 	 

	 	 	 	 	 
	 	THE BANK OF NEW YORK, as Trustee

 	 
	 	By:  	/s/ John T. Needham
 	 
	 	 	Name:  	John T. Needham, Jr. 	 
	 	 	Title:  	Vice President 	 
	 
	 	WITNESSES:

 	 
	 	1.  	/s/ Kevin F. Binnie
 	 
	 	 	Name:  	Kevin F. Binnie 	 
	 	 	 	 
	 	2.  	     /s/ Lucia Jaklitch
 	 
	 	 	Name:  	Lucia Jaklitch 	 
	 	 	 	 

2

 

	 	 	 	 	 

	 	 	 	 	 	 	 
	STATE OF NEW YORK

     

	 	 	)

)	 	 	     
ss:
	COUNTY OF NEW YORK

	 	 	)	 	 	 

          On this 7th day of February, 2007 before me, a notary public within and for said county,
personally appeared John T. Needham, Jr., to me personally known who being duly sworn,
did say that he is a Vice President of The Bank of New York, one of the persons described
in and which executed the foregoing instrument, and acknowledge said instrument to be the free act
and deed of said corporation.

          On this 7th day of February, 2007, before me personally came Kevin F. Binnie and
Lucia Jaklitsch to me personally known, who being by me sworn, did depose and say that
they signed their names to the foregoing instrument as witnesses.

	 	 	 
	     

	Emily Fayan	 
	 

	 	 
	 

	Notary Public	 
	 

	COMMISSION EXPIRES Dec. 31, 2009	 

3

 

	 	 	 	 	 	 	 
	STATE OF NEW YORK

     

	 	 	)

)	 	 	     
ss:
	COUNTY OF NEW YORK

	 	 	)	 	 	 

          On this 7th day of February, 2007, before me personally came Theodore M.
Helms, to me known, who, being by me duly sworn, did depose and say that he is the
Attorney-in-Fact of Petrobras International Finance Company — PIFCo, a corporation described in and
which executed the foregoing instrument and acknowledge that said instrument to be the free act and
deed of said entity.

          On this 7th day of February, 2007, before me personally came Theodore M.
Helms, to me known, who, being by me duly sworn, did depose and say that he is the
Attorney-in-Fact of Petróleo Brasileiro S.A. — Petrobras, a corporation described in and which
executed the foregoing instrument and acknowledge that said instrument to be the free act and deed
of said entity.

          On this 7th day of February, 2007, before me personally came Jo Dean
Adams and Manuel Silva to me personally known, who being by
me sworn, did depose and say that they signed their names to the foregoing instrument as witnesses.

[Notarial Seal]

	 	 	 
	     

	Lauren A. Roberts	 
	 

	 	 
	 

	Notary Public	 
	 

	COMMISSION EXPIRES 2010	 

4

 

Exhibit A

Form of 6.125% Global Note due 2016

GLOBAL NOTE

THIS NOTE IS A GLOBAL NOTE WITHIN THE MEANING OF THE INDENTURE HEREINAFTER REFERRED TO AND IS
REGISTERED IN THE NAME OF A DEPOSITORY OR A NOMINEE THEREOF. THIS NOTE MAY NOT BE EXCHANGED IN
WHOLE OR IN PART FOR A NOTE REGISTERED, AND NO TRANSFER OF THIS NOTE IN WHOLE OR IN PART MAY BE
REGISTERED, IN THE NAME OF ANY PERSON OTHER THAN SUCH DEPOSITORY OR ITS NOMINEE EXCEPT IN THE
LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE.

UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST
COMPANY TO THE ISSUER OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT AND SUCH
CERTIFICATE ISSUED IN EXCHANGE FOR THIS CERTIFICATE IS REGISTERED IN THE NAME OF CEDE & CO., OR
SUCH OTHER NAME AS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY, ANY TRANSFER,
PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL, SINCE THE
REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.

5

 

PETROBRAS INTERNATIONAL FINANCE COMPANY

6.125% GLOBAL NOTES DUE 2016

No. 2

CUSIP No.: 71645WAL5

ISIN No.: US71645WAL54

Common Code: 027057390

Principal
Amount: U.S.$399,053,000

Initial Issuance Date: February 7, 2007

          This Note is one of a duly authorized issue of notes of PETROBRAS INTERNATIONAL FINANCE
COMPANY, an exempted company with limited liability organized under the laws of the Cayman Islands
(the “Issuer”), designated as its 6.125% Global Notes Due 2016 (the “Notes”),
issued in an initial aggregate principal amount of U.S.$399,053,000 under the Amended and Restated
Fifth Supplemental Indenture (the “Amended and Restated Fifth Supplemental Indenture”),
effective as of February 7, 2007, by and among the Issuer, The Bank of New York, a New York banking
corporation, as successor to JPMorgan Chase Bank, N.A, as Trustee (the “Trustee”), and
Petróleo Brasileiro S.A. — PETROBRAS, a mixed capital company (sociedade de economia mista)
organized under the laws of Brazil (“Petrobras”), to the Indenture, dated as of July 19,
2002 (the “Original Indenture”, and as supplemented by the Amended and Restated Fifth
Supplemental Indenture and any further supplements thereto with respect to the Notes, the
“Indenture”), by and among the Issuer and the Trustee. Reference is hereby made to the
Indenture for a statement of the respective rights, limitations of interests, benefits, obligations
and duties thereunder of the Issuer, the Trustee and the Holders, and of the terms upon which the
Notes are, and are to be, authenticated and delivered. All capitalized terms used in this Note
which are defined in the Indenture and not otherwise defined herein shall have the meanings
assigned to them in the Indenture.

          The Issuer, for value received, hereby promises to pay to Cede & Co. or its registered
assigns, as nominee of The Depository Trust Company (“DTC”) and the Holder of record of
this Note, the principal amount specified above in U.S. dollars on October 6, 2016 (or earlier as
provided for in the Indenture) upon presentation and surrender hereof, at the office or agency of
the Trustee referred to below.

          As provided for in the Indenture, the Issuer promises to pay interest on the outstanding
principal amount hereof, from the Closing Date, semi-annually on April 6 and October 6 of each year
(or if such date is not a Business Day, the next succeeding Business Day following such day),
commencing April 6, 2007 (each such date, an “Interest Payment Date”), at a rate equal to
6.125% per annum. Interest payable, and punctually paid or duly provided for, on this Note on any
Interest Payment Date will, as provided in the Indenture, be paid in U.S. dollars to the Person in
whose name this Note (or one or more predecessor Notes) is registered at the close of business on
the relevant Regular Record Date for such interest payment.

          Payment of the principal of and interest on this Note will be payable by wire transfer to a
U.S. dollar account maintained by the Holder of this Note as reflected in the Security Register of
the Trustee. In the event the date for any payment of the principal of or

6

 

interest on any Note is not a Business Day, then payment will be made on the next Business Day
with the same force and effect as if made on the nominal date of any such date for such payment and
no additional interest will accrue on such payment as a result of such payment being made on the
next succeeding Business Day. Interest accrued with respect to this Note shall be calculated based
on a 360-day year of twelve 30-day months.

          The Notes are subject to redemption by the Issuer on the terms and conditions specified in the
Indenture.

          This Note does not purport to summarize the Indenture, and reference is made to the Indenture
for information with respect to the respective rights, limitations of interests, benefits,
obligations and duties thereunder of the Issuer, the Trustee and the Holders.

          If an Event of Default shall occur and be continuing, the outstanding principal amount of all
the Notes may become or may be declared due and payable in the manner and with the effect provided
in the Indenture.

          Modifications of the Indenture may be made by the Issuer and the Trustee only to the extent
and in the circumstances permitted by the Indenture.

          The Notes shall be issued only in fully registered form, without coupons. Notes shall be
issued in the form of beneficial interests in one or more global securities in denominations of
U.S. $2,000 and integral multiples of U.S.$1,000 in excess thereof.

          Prior to and at the time of due presentment of this Note for registration of transfer, the
Issuer, the Trustee and any agent of the Issuer or the Trustee may treat the Person in whose name
this Note is registered as the owner hereof for all purposes, whether or not this Note is overdue,
and neither the Issuer, the Trustee nor any agent thereof shall be affected by notice to the
contrary.

[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]

7

 

          Unless the certificate of authentication hereon has been duly executed by the Trustee by
manual signature, this Note shall not be entitled to any benefit under the Indenture, or be valid
or obligatory for any purpose.

          THIS NOTE SHALL BE CONSTRUED IN ACCORDANCE WITH, AND GOVERNED BY, THE LAWS OF THE STATE OF NEW
YORK.

          IN WITNESS WHEREOF, the Issuer has caused this Note to be duly executed.

	 	 	 	 	 
	 	PETROBRAS INTERNATIONAL FINANCE COMPANY

 	 
	 	By  	 	 
	 	 	Name:  	 	 
	 	 	Title:  	 	 
	 
	 	WITNESSES:

 	 
	 	1.  	 	 
	 	 	Name:  	 	 
	 	 	 	 
	 	2.  	
 	 
	 	 	Name:  	 	 
	 	 	 	 

8

 

	 	 	 	 	 

	 	 	 	 	 	 	 
	STATE OF NEW YORK

     

	 	 	)

)	 	 	     
ss:
	COUNTY OF NEW YORK

	 	 	)	 	 	 

On this 7th day of February, 2007, before me personally came ___, to me known, who, being by
me duly sworn, did depose and say that he is the ___ of Petrobras International Finance
Company, a corporation described in and which executed the foregoing instrument and acknowledges
that said instrument to be the free act and deed of said entity.

On this 7th day of February, 2007, before me personally came ___ and ___
to me personally known, who being by me sworn, did depose and say that they signed their names to the forgoing instrument as witnesses.

          [Notarial Seal]

	 	 	 
	     

	 

Notary Public	 
	 

	COMMISSION EXPIRES	 

9

 

CERTIFICATE OF AUTHENTICATION

     This is one of the Securities of the series designated therein referred to in the within
mentioned Indenture.

Dated: February 7, 2007

	 	 	 	 	 
	 	The Bank of New York 
As Trustee

 	 
	 	By:  	 	 
	 	 	Name:  	 	 
	 	 	Title:  	Authorized Officer 	 

10

 

	 	 	 	 	 

ASSIGNMENT FORM

For value received

hereby sells, assigns and transfers unto

(Please insert social security or

other identifying number of assignee)

(Please print or type name and address,

including zip code, of assignee:)

the within Note and does hereby irrevocably constitute and appoint Attorney to transfer the Note on
the books of the Note Registrar with full power of substitution in the premises.

	 	 	 	 	 
	Date:

	 	Your Signature:
	 	     
	 

	 	 	 	(Sign exactly as your name

	 

	 	 	 	appears on the face of this Note)

11

 

Exhibit B

Form of Standby Purchase Agreement

[To Come]

12

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