DCT

1:15-cv-00274

Syngenta Crop Protection LLC v. Willowood LLC

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I. Executive Summary and Procedural Information

  • Parties & Counsel:
  • Case Identification: 1:15-cv-00274, M.D.N.C., 03/27/2015
  • Venue Allegations: Venue is alleged based on Defendants having committed acts of patent infringement, maintaining systematic and continuous contacts, and regularly transacting business within the Middle District of North Carolina, including offering the accused products for sale in the district.
  • Core Dispute: Plaintiff alleges that Defendant’s azoxystrobin-based fungicide products infringe patents related to the azoxystrobin chemical compound itself and to specific processes for its manufacture.
  • Technical Context: The technology lies in the field of agricultural chemistry, specifically concerning the breakthrough fungicide azoxystrobin, which is a widely used active ingredient for controlling fungal growth and enhancing yields in a variety of crops.
  • Key Procedural History: The complaint details extensive pre-suit correspondence between the parties, including letters from Syngenta to Willowood dated January 30, 2014, and August 25, 2014, providing notice of the patents-in-suit. This correspondence is alleged to establish Defendant’s knowledge of the patents prior to the lawsuit, forming a basis for the willfulness allegations.

Case Timeline

Date Event
1987-04-17 ’076 Patent Priority Date
1987-04-17 ’256 Patent Priority Date
1990-11-16 ’138 Patent Priority Date
1997-02-11 ’076 Patent Issue Date
1997-05-27 ’256 Patent Issue Date
1998-12-08 ’138 Patent Issue Date
2005-04-26 ’761 Patent Priority Date
2012-02-28 ’761 Patent Issue Date
2013-08-13 Willowood files EPA application for Azoxy 2SC
2014-01-30 Syngenta sends letter notifying Willowood of ’076 and ’256 Patents
2014-06-16 Willowood announces EPA approval for accused products
2014-08-25 Syngenta sends letter notifying Willowood of ’138 and ’761 Patents
2015-03-27 Complaint Filing Date

II. Technology and Patent(s)-in-Suit Analysis

U.S. Patent No. 5,602,076 - "Certain Fungicides, Pesticides and Plant Growth Regulants"

  • Patent Identification: U.S. Patent No. 5,602,076, "Certain Fungicides, Pesticides and Plant Growth Regulants," issued February 11, 1997 (Compl. ¶22).

The Invention Explained

  • Problem Addressed: The patent addresses the need in agriculture for chemical compounds useful as fungicides, pesticides, and plant growth regulators to combat fungal infections in plants and control pests (’076 Patent, Abstract).
  • The Patented Solution: The invention provides a class of chemical compounds derived from acrylic acid, defined by a general chemical structure (Formula I), that exhibit these beneficial agricultural properties (’076 Patent, Abstract; col. 1:21-29). The core structure involves a substituted pyridinyl or pyrimidinyl group linked via an oxygen or sulfur atom to a phenyl acrylate moiety, with the patent claiming a broad genus of related molecules (’076 Patent, col. 1:30-47).
  • Technical Importance: The claimed genus of compounds includes azoxystrobin, which the complaint describes as a "break-through fungicidal chemical" that effectively controls fungal growth and enhances the yield of a wide variety of plants (Compl. ¶20).

Key Claims at a Glance

  • The complaint asserts infringement of at least independent claim 1 (Compl. ¶90).
  • Claim 1 recites a chemical compound defined by a Markush structure (Formula I), the essential elements of which are:
    • A substituted pyrimidinyl or pyridinyl group (W)
    • Linked by an oxygen or sulfur atom (A)
    • To a phenyl acrylate structure with various specified substituents (X, Y, Z) and ester/ether groups (R¹ and R²)
  • The complaint does not specify assertion of dependent claims but reserves rights by alleging infringement of claim 1 "among others" (Compl. ¶90).

U.S. Patent No. 5,633,256 - "Certain Pyrimidinyloxy-Phenyl Acrylates, Derivatives Thereof and Their Fungicidal Use"

  • Patent Identification: U.S. Patent No. 5,633,256, "Certain Pyrimidinyloxy-Phenyl Acrylates, Derivatives Thereof and Their Fungicidal Use," issued May 27, 1997 (Compl. ¶23).

The Invention Explained

  • Problem Addressed: The patent, like the related ’076 Patent, is directed to chemical compounds useful as agricultural fungicides (’256 Patent, Abstract).
  • The Patented Solution: The invention claims a genus of pyrimidinyloxy-phenyl acrylate compounds, defined by a general chemical structure, and their use in fungicidal compositions (’256 Patent, Abstract; col. 1:10-18). This patent appears to claim a more specific sub-genus of the chemical family disclosed in the ’076 Patent, focusing on compounds where a pyrimidinyl group is linked via an oxygen atom to the phenyl acrylate core.
  • Technical Importance: The technology claimed is part of the intellectual property portfolio covering the commercially significant azoxystrobin fungicide (Compl. ¶20, ¶62).

Key Claims at a Glance

  • The complaint asserts infringement of at least independent claim 1 (Compl. ¶95).
  • Claim 1 recites a chemical compound defined by a Markush structure, the essential elements of which include:
    • A substituted pyrimidinyl group (W)
    • Linked by an oxygen atom (A)
    • To a phenyl acrylate structure with specified substituents
  • The complaint alleges infringement of claim 1 "among others," thereby reserving the right to assert other claims (Compl. ¶95).

U.S. Patent No. 5,847,138 - "Chemical Process"

  • Patent Identification: U.S. Patent No. 5,847,138, "Chemical Process," issued December 8, 1998 (Compl. ¶24).
  • Technology Synopsis: The patent relates to processes for manufacturing azoxystrobin and its chemical intermediates (Compl. ¶68). The invention provides a method for preparing phenoxypyrimidine compounds, which are key precursors, by reacting a 3-(a-methoxy)methylenebenzofuranone with a dihalopyrimidine (’138 Patent, Abstract).
  • Asserted Claims: At least claim 6 is asserted (Compl. ¶100).
  • Accused Features: The complaint alleges on information and belief that the process used by Willowood to manufacture its azoxystrobin-containing products infringes this patent (Compl. ¶74, ¶77).

U.S. Patent No. 8,124,761 - "Process for the Preparation of Azoxystrobin Using DABCO as a Catalyst and Novel Intermediates Used in the Process"

  • Patent Identification: U.S. Patent No. 8,124,761, "Process for the Preparation of Azoxystrobin Using DABCO as a Catalyst and Novel Intermediates Used in the Process," issued February 28, 2012 (Compl. ¶25).
  • Technology Synopsis: The patent discloses a specific chemical process for preparing azoxystrobin that utilizes 1,4-diazabicyclo[2.2.2]octane (DABCO) as a catalyst (’761 Patent, Abstract). This process is alleged to be an improvement for manufacturing the compound (Compl. ¶68).
  • Asserted Claims: At least claim 1 is asserted (Compl. ¶105).
  • Accused Features: The complaint alleges on information and belief that Willowood’s manufacturing process for its azoxystrobin-containing products uses the claimed catalytic method (Compl. ¶74, ¶77).

III. The Accused Instrumentality

Product Identification

  • The accused instrumentalities are Defendant’s "Azoxy 2SC" and "AzoxyProp Xtra" products (Compl. ¶1).

Functionality and Market Context

  • The accused products are agricultural fungicides that contain the chemical compound azoxystrobin as their active ingredient (Compl. ¶37). The complaint alleges that these products are sold and offered for sale throughout the United States, including in North Carolina, as generic alternatives to Syngenta's own branded azoxystrobin products (Compl. ¶14, ¶63).
  • No probative visual evidence provided in complaint.

IV. Analysis of Infringement Allegations

5,602,076 Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A compound having the formula (I)...or a stereoisomer thereof... The accused Azoxy 2SC and AzoxyProp Xtra products are alleged to comprise the chemical compound azoxystrobin. ¶90 col. 1:21-29
wherein W is a substituted pyrimidinyl group... In azoxystrobin, the W group is a pyrimidinyl ring substituted with a 2-cyanophenoxy group. ¶90 col. 2:30-32
A is either an oxygen atom or S(O)n... In azoxystrobin, the A group is an oxygen atom linking the pyrimidinyl and phenyl rings. ¶90 col. 2:32-33
X, Y and Z...are hydrogen... In azoxystrobin, the phenyl ring is unsubstituted, such that X, Y, and Z are hydrogen atoms. ¶90 col. 2:33-35
R¹ and R²...are optionally substituted alkyl groups... In azoxystrobin, R¹ and R² are both methyl groups. ¶90 col. 2:40-44

5,633,256 Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A compound of formula (I)... The accused Azoxy 2SC and AzoxyProp Xtra products are alleged to comprise the chemical compound azoxystrobin. ¶95 col. 1:20-27
wherein W is a substituted pyrimidinyl group... In azoxystrobin, the W group is a pyrimidinyl ring substituted with a 2-cyanophenoxy group. ¶95 col. 2:30-31
A is an oxygen atom... In azoxystrobin, the A group is an oxygen atom linking the pyrimidinyl and phenyl rings. ¶95 col. 2:31-32
X, Y and Z...are hydrogen... In azoxystrobin, the phenyl ring is unsubstituted, such that X, Y, and Z are hydrogen atoms. ¶95 col. 2:32-34
  • Identified Points of Contention:
    • Composition Patents (’076 and ’256): The core infringement theory is straightforward: the accused products are alleged to contain the chemical compound azoxystrobin, which Syngenta alleges falls within the scope of the asserted claims (Compl. ¶90, ¶95). The primary factual question is whether chemical analysis of the accused products confirms they contain a compound meeting all structural limitations of the asserted claims. A potential legal dispute may concern the validity of the patents, which falls outside the scope of infringement analysis.
    • Process Patents (’138 and ’761): The infringement allegations for the manufacturing process patents are made "upon information and belief," as the defendant's process is proprietary (Compl. ¶74, ¶77). A central point of contention will be evidentiary: what proof can be adduced through discovery to demonstrate that Willowood’s confidential manufacturing process for azoxystrobin practices the specific steps recited in the asserted claims of the ’138 and ’761 patents. The complaint notes that Willowood previously refused to provide its manufacturing specifications (Compl. ¶69).

V. Key Claim Terms for Construction

  • The Term: "a substituted pyrimidinyl group" (’076 Patent, Claim 1; ’256 Patent, Claim 1)
  • Context and Importance: The definition of this term is critical because the specific identity of the substituent on the pyrimidinyl ring determines the final chemical compound. The infringement allegation rests on the "2-cyanophenoxy" moiety found in azoxystrobin qualifying as a valid substituent under the claim's language. Practitioners may focus on this term to determine if the claim properly covers the specific commercial embodiment at issue.
  • Intrinsic Evidence for Interpretation:
    • Evidence for a Broader Interpretation: The specifications of both patents provide extensive lists of possible substituents for the pyrimidinyl ring. These lists include broad chemical classes such as "optionally substituted aryloxy" and "optionally substituted heteroaryloxy" (’076 Patent, col. 3:28-31; ’256 Patent, col. 3:28-31). This language may support an interpretation where "substituted" encompasses a wide variety of chemical groups, including the 2-cyanophenoxy group of azoxystrobin.
    • Evidence for a Narrower Interpretation: A party might argue that the scope of "substituted" should be interpreted in light of the specific examples and embodiments disclosed in the patent. However, the patents' text explicitly defines substituents to include broad categories like "aryloxy," and further states that aryl moieties themselves can be substituted with groups including "cyano" (’076 Patent, col. 3:1-12; ’256 Patent, col. 3:1-12).

VI. Other Allegations

  • Indirect Infringement: The complaint alleges induced infringement of the ’076 and ’256 patents. The factual basis is the allegation that Willowood "contracted with, and instructed, Analytical & Regulatory Chemistry, Inc. to use and analyze infringing azoxystrobin in connection with submissions to the EPA," which is alleged to constitute an affirmative act of encouragement with knowledge of the patents (Compl. ¶91, ¶96).
  • Willful Infringement: Willfulness is alleged for all four patents-in-suit (Compl. ¶93, ¶98, ¶103, ¶108). The allegations are based on pre-suit knowledge established through multiple notice letters sent by Syngenta to Willowood, specifically citing the patents, on January 30, 2014, and August 25, 2014 (Compl. ¶60, ¶67).

VII. Analyst’s Conclusion: Key Questions for the Case

  • A central evidentiary issue will be one of process discovery: what evidence can Syngenta obtain to demonstrate that Willowood's proprietary manufacturing methods for azoxystrobin practice the specific steps claimed in the '138 and '761 process patents, particularly given the allegations are pled on information and belief?
  • A key legal and factual question will be one of infringing composition: assuming the accused products are confirmed to contain azoxystrobin, the dispute may shift to the validity of the '076 and '256 patents, questioning whether the claimed genus of compounds was non-obvious and adequately described at the time of invention.
  • Given the detailed pre-suit correspondence alleged in the complaint, a significant question for trial will be one of subjective intent: did Willowood's alleged conduct, following receipt of multiple notice letters identifying the patents-in-suit, constitute objective recklessness rising to the level of willful infringement?