DCT

1:18-cv-00268

BASF Corp v. Willowood LLC

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Key Events
Complaint

I. Executive Summary and Procedural Information

  • Parties & Counsel:
  • Case Identification: 1:18-cv-00268, D. Colo., 02/01/2018
  • Venue Allegations: Venue is alleged to be proper in the District of Colorado because Defendants have committed acts of patent infringement, engaged in systematic and continuous contacts, and regularly transact business in the state, including the marketing and sale of agrochemical products.
  • Core Dispute: Plaintiff alleges that Defendant’s pyraclostrobin-based fungicide products infringe one patent covering a specific crystalline form of the active ingredient and a second patent covering a method for manufacturing an intermediate used to produce that ingredient.
  • Technical Context: The dispute is in the field of agricultural chemicals, specifically fungicides, where the physical form of an active ingredient can be critical for creating stable and effective product formulations.
  • Key Procedural History: The complaint alleges a history of pre-suit communications, asserting that Defendant had actual knowledge of the ’392 patent as of July 15, 2016, and the ’451 patent as of September 15, 2017. These allegations of pre-suit notice form the basis of the willfulness claims.

Case Timeline

Date Event
1997-07-30 Priority Date for U.S. Patent No. 6,133,451
2000-10-17 U.S. Patent No. 6,133,451 Issued
2005-06-20 Priority Date for U.S. Patent No. 7,816,392
2010-10-19 U.S. Patent No. 7,816,392 Issued
~2015 Willowood allegedly directs testing of its pyraclostrobin products
2016-05-24 EPA issues registration for Willowood Pyrac 2SC
2016-07-15 Date by which Willowood allegedly had knowledge of '392 Patent
2016-08-18 EPA issues registration for Willowood Pyraclostrobin Technical
2016-11-18 Willowood sends letter regarding the '392 Patent
2017-04-03 Willowood sends letter stating intent to sell Pyrac 2EC in the U.S.
2017-09-15 Date by which Willowood allegedly had knowledge of '451 Patent
2017-10-03 Willowood sends letter allegedly conceding use of a process step from the '451 Patent
2017-12-14 Date by which Colorado approved registration for Willowood Pyrac 2EC
2018-02-01 Complaint Filed

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

U.S. Patent No. 7,816,392, "Crystalline Modifications to Pyraclostrobin," Issued Oct. 19, 2010

The Invention Explained

  • Problem Addressed: The patent explains that commercially available pyraclostrobin, an active fungicidal compound, exists as an "amorphous substance" with a low melting point. This "tackiness" makes it unsuitable for preparing conventional aqueous suspension concentrates, a common and economically important type of agricultural product formulation (US 7,816,392 B2, col. 1:15-28).
  • The Patented Solution: The patent discloses new, stable crystalline forms (polymorphs) of pyraclostrobin. The invention centers on "modification IV," a specific crystalline structure that is not tacky and permits the creation of stable suspension concentrates with improved storage characteristics (US 7,816,392 B2, col. 1:47-51; col. 10:55-58).
  • Technical Importance: This innovation enabled the formulation of pyraclostrobin into stable, high-concentration liquid products, potentially enhancing its commercial utility and allowing it to be combined with other active ingredients in desirable formulations (US 7,816,392 B2, col. 1:21-28).

Key Claims at a Glance

  • The complaint asserts claims 1-3 (Compl. ¶70).
  • Independent Claim 1 defines a composition of matter:
    • A crystalline modification IV of pyraclostrobin, which
    • in an X-ray powder diffractogram at 25° C.,
    • shows at least three of five specific, enumerated reflexes (peaks) at given "d" spacings.
  • The complaint notes the right to assert dependent claims, such as claim 2, which adds a specific melting point range, and claim 3, which adds a minimum purity level (Compl. ¶39).

U.S. Patent No. 6,133,451, "Method For Producing 2-(3-Pyrazolyl-Oxymethylene) Nitrobenzenes," Issued Oct. 17, 2000

The Invention Explained

  • Problem Addressed: The patent addresses safety and handling problems in the industrial production of o-nitrobenzyl bromide (Formula III), an intermediate chemical used to make pyraclostrobin. This intermediate is described as a "lachrymatory and mucosal-irritant" and possessing "low thermal stability," making its isolation and handling on an industrial scale difficult and hazardous (US 6,133,451, col. 2:31-34).
  • The Patented Solution: The patent claims a process where the hazardous o-nitrobenzyl bromide intermediate is generated and then immediately reacted with the next chemical in the synthesis pathway (a 3-hydroxypyrazole) within the same solvent, without being isolated. This "in-situ" or "one-pot" approach avoids the dangerous handling step (US 6,133,451, col. 2:45-50).
  • Technical Importance: The invention provides an "industrially applicable" manufacturing process that resolves significant safety issues while still producing the desired downstream compound in "good yield and in excellent purity" (US 6,133,451, col. 2:38-44, 2:51-53).

Key Claims at a Glance

  • The complaint asserts at least claim 1 (Compl. ¶89).
  • Independent Claim 1 defines a multi-step chemical process:
    • A process for preparing 2-(3-pyrazolyloxymethylene) nitrobenzene derivatives (Formula I),
    • by brominating an o-nitrotoluene (Formula II) to form an o-nitrobenzyl bromide (Formula III) in a nonpolar, aprotic solvent,
    • and subsequently reacting the resulting solution of Formula III with a 3-hydroxypyrazole (Formula IV) in the presence of a base,
    • wherein the solution of Formula III is reacted directly with Formula IV in the same solvent "without intermediate isolation of" Formula III.

III. The Accused Instrumentality

  • Product Identification: The accused instrumentalities are "Willowood Pyraclostrobin Technical," "Willowood Pyrac 2SC," and "Willowood Pyrac 2EC" (Compl. ¶¶9, 27, 52).
  • Functionality and Market Context: "Willowood Pyraclostrobin Technical" is a technical grade product containing approximately 99.0% pyraclostrobin, which is intended "For Use In Formulating Fungicides Only" (Compl. ¶30). The complaint alleges that this technical product is used to formulate the end-use products, Willowood Pyrac 2SC and Willowood Pyrac 2EC (Compl. ¶58). These end-use products are fungicides sold for "disease control and plant health in a variety of crops" (Compl. ¶¶52, 54).

IV. Analysis of Infringement Allegations

No probative visual evidence provided in complaint.

’392 Patent Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A crystalline modification IV of pyraclostrobin which, in an X-ray powder diffractogram at 25° C., shows at least three of the following reflexes: d=6.02±0.01 Å d=4.78±0.01 Å d=4.01±0.01 Å d=3.55±0.01 Å d=3.01±0.01 Å. The complaint alleges on information and belief that the pyraclostrobin contained in Defendants' "Willowood Pyraclostrobin Technical," "Willowood Pyrac 2SC," and "Willowood Pyrac 2EC" products possesses this specific crystalline structure. ¶70, ¶79, ¶80 col. 25:11-20
  • Identified Points of Contention:
    • Technical Question: The central dispute appears to be factual: does the pyraclostrobin in Defendants' products exhibit the specific X-ray diffraction pattern of "modification IV" as claimed? The complaint's allegations rely on "information and belief" and an alleged statement from Defendant that its testing had "not demonstrated... that it avoids the claim limitations" (Compl. ¶66, ¶70). This raises the evidentiary question of what physical form of pyraclostrobin is actually present in the accused products, which will likely require expert testing during discovery.

’451 Patent Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
...wherein the solution of the o-nitrobenzyl bromide III resulting from the bromination is reacted further with IV, in the solvent used, directly without intermediate isolation of the o-nitrobenzyl bromide III. Plaintiff alleges the process used to make the pyraclostrobin in the accused products performs this step. The allegation is based on the presence of a specific impurity ("MMC") in a tested sample of Willowood Pyrac 2EC, which allegedly "evidences" that the reaction was performed "directly without intermediate isolation of Formula III." ¶75, ¶89 col. 14:3-5
  • Identified Points of Contention:
    • Technical Question: A key issue is whether the presence of the identified "MMC" impurity serves as a definitive "fingerprint" of the patented process. The infringement analysis may turn on whether the MMC impurity can only be formed when the reaction is conducted "without intermediate isolation," as claimed, or if it could also be a byproduct of other, non-infringing manufacturing processes.

V. Key Claim Terms for Construction

  • The Term: "directly without intermediate isolation" (from '451 Patent, Claim 1)
  • Context and Importance: This term is the core of the inventive concept of the ’451 patent, distinguishing it from prior art processes that involved handling a hazardous intermediate. The entire infringement allegation under 35 U.S.C. § 271(g) hinges on proving, likely through circumstantial evidence like the MMC impurity, that the accused products were made using a process containing this specific step.
  • Intrinsic Evidence for Interpretation:
    • Evidence for a Broader Interpretation: The patent's background focuses on solving the "difficult operating and safety problems in handling [Formula] III," including its irritant effect and thermal instability (US 6,133,451, col. 2:31-41). A party could argue the term should be construed broadly to cover any process that avoids the discrete step of separating, purifying, and storing the intermediate, as these are the activities that create the "handling" problems the patent sought to solve.
    • Evidence for a Narrower Interpretation: The claim language states the reaction occurs "in the solvent used" (US 6,133,451, col. 14:4). A party could argue this requires a strict "one-pot" reaction where the intermediate is generated and consumed in the very same vessel. Any transfer to a different reactor, even without purification, might be argued to constitute a form of "isolation" that falls outside the claim scope.

VI. Other Allegations

  • Indirect Infringement: The complaint's infringement counts focus on direct infringement under 35 U.S.C. § 271(a) for the ’392 patent and importation of a product made by a patented process under 35 U.S.C. § 271(g) for the ’451 patent (Compl. ¶¶81, 90).
  • Willful Infringement: The complaint explicitly alleges that Defendants' infringement has been willful for both patents (Compl. ¶86, ¶93). This allegation is supported by claims of pre-suit knowledge, citing specific dates ("no later than July 15, 2016" for the '392 patent and "no later than September 15, 2017" for the '451 patent) and correspondence between the parties discussing the patents (Compl. ¶¶65-66, 72-73).

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

  • A central issue will be one of factual evidence: What is the actual physical and chemical nature of Defendants' products? The case will likely turn on competing expert analyses regarding (1) whether the accused pyraclostrobin possesses the specific crystalline structure defined by the '392 patent, and (2) whether the presence of a specific impurity is conclusive proof that the product was made using the "without intermediate isolation" process of the '451 patent.
  • A second core issue will be one of causation: Assuming the "MMC" impurity is present in the accused product, does its presence uniquely and necessarily result from the practice of the claimed method in the '451 patent? The court may need to resolve whether alternative, non-infringing manufacturing routes could also produce the same chemical byproduct.
  • A final question will concern culpability: Based on the alleged pre-suit communications detailed in the complaint, did Defendants' alleged infringement of one or both patents rise to the level of willfulness, which could expose them to enhanced damages if found liable?