4:24-cv-00055
FMC Corp v. Albaugh LLC
I. Executive Summary and Procedural Information
- Parties & Counsel:
- Plaintiff: FMC Corporation (Delaware)
- Defendant: Albaugh, LLC (Iowa)
- Plaintiff’s Counsel: Eckley Law PLLC; Armstrong Teasdale LLP
- Case Identification: 4:24-cv-00055, S.D. Iowa, 02/12/2024
- Venue Allegations: Venue is alleged to be proper in the Southern District of Iowa as Defendant is a limited liability company residing in Ankeny, Iowa, within the district.
- Core Dispute: Plaintiff alleges that Defendant’s agrochemical product containing chlorantraniliprole is manufactured using processes that infringe three U.S. patents covering methods for producing chlorantraniliprole and its chemical intermediates.
- Technical Context: The technology concerns chemical synthesis processes for chlorantraniliprole, an anthranilic diamide insecticide that is a commercially significant active ingredient in broad-spectrum insect-control products.
- Key Procedural History: The complaint states that on November 3, 2023, Plaintiff notified Defendant of its infringement concerns. Plaintiff alleges that its subsequent requests for information regarding Defendant's manufacturing process were refused. This refusal forms the basis for Plaintiff's invocation of 35 U.S.C. § 295, which allows a court to presume a product was made by a patented process if the patentee made a reasonable but unsuccessful effort to determine the process actually used.
Case Timeline
| Date | Event |
|---|---|
| 2002-07-31 | ’057 Patent Priority Date |
| 2003-06-12 | ’601 Patent Priority Date |
| 2004-12-07 | ’260 Patent Priority Date |
| 2007-10-02 | ’601 Patent Issue Date |
| 2008-03-04 | ’057 Patent Issue Date |
| 2009-05-05 | ’260 Patent Issue Date |
| 2023-11-03 | Plaintiff notifies Defendant of infringement concerns |
| 2024-02-12 | Complaint Filing Date |
II. Technology and Patent(s)-in-Suit Analysis
U.S. Patent No. 7,339,057 - "Method for preparing fused oxazinones from ortho-amino aromatic carboxylic acid and carboxylic acid in the presence of a sulfonyl chloride and pyridine"
The "’057 Patent," issued March 4, 2008
The Invention Explained
- Problem Addressed: The patent background identifies a general need for "additional methods for preparing fused oxazinones," which serve as important chemical intermediates in the production of agrochemicals and pharmaceuticals (’057 Patent, col. 1:15-20).
- The Patented Solution: The patent discloses methods for synthesizing fused oxazinones and related compounds. One key process described is the reaction of a benzoxazinone intermediate with an amine to produce N-phenylpyrazole-1-carboxamides, a class of compounds that includes the insecticide chlorantraniliprole (’057 Patent, Abstract; col. 65:5-62 & Scheme 29). This provides a specific chemical pathway for creating the final active ingredient from a key intermediate.
- Technical Importance: The complaint alleges that the patented synthesis routes are among the only "commercially viable processes" for manufacturing chlorantraniliprole, suggesting the invention provides a practical and efficient method for large-scale production (Compl. ¶80).
Key Claims at a Glance
- While the complaint does not specify claims, its infringement theory for the ’057 Patent maps to the process for creating a compound of "Formula III" from an intermediate of "Formula 1a," as depicted in Scheme 29 (Compl. ¶45-48). Claim 10 of the patent appears representative of this alleged process.
- Independent Claim 10 (essential elements):
- A method for preparing a compound of Formula III,
- comprising: contacting a compound of Formula 1a,
- with an amine of the formula R²(R³)NH,
- wherein Formulas 1a and III and the various R-groups define the specific chemical structures of the reactants and the final product.
U.S. Patent No. 7,276,601 - "Method and preparing fused oxazinones"
The "’601 Patent," issued October 2, 2007
The Invention Explained
- Problem Addressed: Similar to the ’057 Patent, the background section of the ’601 Patent states that a "need exists for additional methods for preparing fused oxazinones" for use as intermediates in crop protection agents and other fine chemicals (’601 Patent, col. 1:5-8).
- The Patented Solution: The patent discloses a method for preparing fused oxazinones by contacting a carboxylic acid with a sulfonyl chloride and an isatoic anhydride in the presence of a tertiary amine (’601 Patent, Abstract). The complaint focuses on the subsequent step covered by the patent: the conversion of a benzoxazinone intermediate (Formula 1a) into an anthranilamide compound (Formula III) by reacting it with an amine, a process also depicted in Scheme 29 of this patent (’601 Patent, col. 61:5-35; Compl. ¶57-59).
- Technical Importance: The complaint alleges this patent covers one of the only commercially viable methods for producing benzoxazinone intermediates used in the final reaction step to create chlorantraniliprole (Compl. ¶69, ¶80).
Key Claims at a Glance
- The complaint's infringement theory maps to the process for preparing "Formula III" from "Formula 1a" as shown in Scheme 29 (Compl. ¶57-59). Claim 7 of the patent appears representative of this alleged process.
- Independent Claim 7 (essential elements):
- A method for preparing a compound of Formula III,
- comprising: contacting a compound of Formula 1a,
- with an amine of the formula R²(R³)NH,
- wherein Formulas 1a and III and the various R-groups define the specific chemical structures of the reactants and the final product.
U.S. Patent No. 7,528,260 - "Method for preparing N-phenylpyrazole-1-carboxamides"
The "’260 Patent," issued May 5, 2009
Technology Synopsis
This patent claims a method for preparing N-phenylpyrazole-1-carboxamides (such as chlorantraniliprole) by combining a carboxylic acid compound, an aniline compound, and a sulfonyl chloride (Compl. ¶71; ’260 Patent, Claim 1). The complaint presents this as a distinct, alternative synthesis route to the final product compared to the intermediate-based reaction described for the ’057 and ’601 Patents (Compl. ¶45, ¶70).
Asserted Claims
The complaint explicitly references Claim 1 (Compl. ¶71).
Accused Features
The manufacturing process used to produce the chlorantraniliprole contained in Defendant's "Exceliprole 4SC" product is accused of infringing this patent (Compl. ¶22, ¶70).
III. The Accused Instrumentality
Product Identification
The accused product is Defendant's "Exceliprole 4SC," which the complaint alleges contains the active ingredient chlorantraniliprole (Compl. ¶22). The infringement allegation is directed at the process by which this chlorantraniliprole is manufactured, with the resulting product then being imported, used, or sold in the United States in violation of 35 U.S.C. § 271(g) (Compl. ¶30).
Functionality and Market Context
Chlorantraniliprole is an anthranilic diamide insecticide marketed by Plaintiff under the trademarks Rynaxypyr® and Coragen® (Compl. ¶17, ¶18). The complaint alleges that Plaintiff's products containing this active ingredient generate approximately $1.6 billion in annual sales, highlighting its commercial significance (Compl. ¶19). Defendant is alleged to have conducted tests and submitted resulting data to the U.S. Environmental Protection Agency in an effort to register its own chlorantraniliprole-containing products (Compl. ¶23-24). The complaint includes a marketing image for Plaintiff's Coragen® product, which contains the Rynaxypyr® active ingredient at issue (Compl. p. 5).
IV. Analysis of Infringement Allegations
The complaint's infringement theory is based on 35 U.S.C. § 271(g), which prohibits the importation or sale of a product made by a process patented in the U.S. Lacking direct evidence of the manufacturing process, the complaint attempts to show infringement by demonstrating that the chemical structure of the final product, chlorantraniliprole, matches the structure of the compound produced by the patented processes. It further alleges these patented processes are the only commercially viable routes, creating a "substantial likelihood" of infringement under 35 U.S.C. § 295 (Compl. ¶40-41, ¶80).
The complaint provides a visual comparison of the generic chemical structure from the patent's Scheme 29 and the specific structure of chlorantraniliprole (Compl. p. 10). This side-by-side view illustrates the core of the infringement allegation: that the accused product is an embodiment of the chemical entity produced by the patented method.
’057 Patent Infringement Allegations
| Claim Element (from product of process in Claim 10) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| The product of the method is a compound of Formula III, defined by substituents including... | The chlorantraniliprole in the Accused Products is alleged to satisfy the structural requirements of Formula III. | ¶48 | col. 66:1-30 |
| ...substituent X is preferably N | In the accused chlorantraniliprole, the corresponding atom X is N. | ¶49 | col. 65:1-46 |
| ...substituent Y is preferably N | In the accused chlorantraniliprole, the corresponding atom Y is N. | ¶50 | col. 65:1-46 |
| ...substituent R² is preferably H or CH₃ | In the accused chlorantraniliprole, the corresponding substituent R² is H. | ¶51 | col. 65:1-46 |
| ...substituent R³ is preferably C₁-C₄ alkyl | In the accused chlorantraniliprole, the corresponding substituent R³ is C₁ alkyl. | ¶52 | col. 65:1-46 |
| ...substituent R⁹ is preferably CF₃, OCHF₂, OCH₂CF₃, Cl, or Br | In the accused chlorantraniliprole, the corresponding substituent R⁹ is Br. | ¶56 | col. 66:42-60 |
’601 Patent Infringement Allegations
| Claim Element (from product of process in Claim 7) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| The product of the method is a compound of Formula III, defined by substituents including... | The chlorantraniliprole in the Accused Products is alleged to satisfy the structural requirements of Formula III. | ¶59 | col. 61:5-35 |
| ...substituent X is preferably N | In the accused chlorantraniliprole, the corresponding atom X is N. | ¶60 | col. 60:9-52 |
| ...substituent Y is preferably N | In the accused chlorantraniliprole, the corresponding atom Y is N. | ¶61 | col. 60:9-52 |
| ...substituent R⁴ is preferably CH₃, F, Cl, or Br | In the accused chlorantraniliprole, the corresponding substituent R⁴ is CH₃. | ¶64 | col. 60:9-52 |
| ...substituent R⁵ is preferably CF₃, CN, F, Cl, Br, or I | In the accused chlorantraniliprole, the corresponding substituent R⁵ is Cl. | ¶65 | col. 60:9-52 |
| ...substituent R⁹ is preferably CF₃, OCHF₂, OCH₂CF₃, Cl, or Br | In the accused chlorantraniliprole, the corresponding substituent R⁹ is Br. | ¶68 | col. 61:46-64 |
Identified Points of Contention:
- Evidentiary Questions: The central issue is factual: what process did Defendant use to manufacture the accused chlorantraniliprole? The complaint's reliance on 35 U.S.C. § 295 raises threshold questions for the court: (1) Has Plaintiff demonstrated a "substantial likelihood" that the product was made by a patented process? (2) Does Plaintiff's pre-suit letter and Defendant's alleged refusal to provide information constitute a "reasonable effort" by Plaintiff to determine the process, thereby shifting the burden of proof to the Defendant? (Compl. ¶40, ¶81-82).
- Technical Questions: A primary technical dispute may concern the validity of Plaintiff's assertion that the patented methods are the "only commercially viable" routes to produce chlorantraniliprole and its intermediates (Compl. ¶69, ¶80). The case may turn on evidence of alternative, economically feasible synthesis pathways that fall outside the scope of the asserted patent claims.
V. Key Claim Terms for Construction
Because the infringement allegations are based on chemical processes and structures, claim construction may focus on the scope of the chemical groups defined in the claims.
- The Term: "a sulfonyl chloride" (from Claim 1 of the ’260 Patent)
- Context and Importance: This term defines a key reactant in the chemical coupling process claimed in the ’260 Patent. The infringement analysis for this patent depends on whether the coupling agent used in Defendant’s manufacturing process falls within the definition of "a sulfonyl chloride." Practitioners may focus on this term because Defendant could argue that it uses a different class of chemical coupling agent that achieves the same result but is not technically a sulfonyl chloride.
- Intrinsic Evidence for Interpretation:
- Evidence for a Broader Interpretation: Claim 1 of the ’260 Patent uses the general term "a sulfonyl chloride" without further structural limitations, which may support an interpretation encompassing the entire chemical class as understood by a person of ordinary skill in the art (’260 Patent, col. 15:15-16).
- Evidence for a Narrower Interpretation: The ’260 Patent specification, in describing the invention, provides examples of specific sulfonyl chlorides, such as methanesulfonyl chloride and p-toluenesulfonyl chloride (’260 Patent, col. 6:49-51). This could be cited to argue that the claimed term should be construed more narrowly to cover only these or structurally similar types of sulfonyl chlorides, rather than all possible compounds in the class.
VI. Other Allegations
- Indirect Infringement: The complaint is premised on infringement under 35 U.S.C. § 271(g), which makes it an act of direct infringement to import, offer to sell, sell, or use within the United States a product which is made by a process patented in the United States (Compl. ¶29-32).
- Willful Infringement: Willfulness is alleged based on Defendant’s knowledge of the asserted patents since at least November 3, 2023, the date of Plaintiff's notice letter (Compl. ¶87). The complaint asserts that infringement subsequent to this date has been willful and deliberate (Compl. ¶87; Prayer for Relief ¶2).
VII. Analyst’s Conclusion: Key Questions for the Case
- A core issue will be one of procedural presumption: Has Plaintiff presented sufficient evidence to establish a "substantial likelihood" that Defendant's product was made by a patented process and that Plaintiff made a "reasonable effort" to determine the actual process, thereby triggering the burden-shifting presumption of infringement under 35 U.S.C. § 295?
- A key factual question will be the existence of alternative synthesis routes: Does discovery reveal that the patented methods are, as Plaintiff alleges, the only "commercially viable" ways to manufacture chlorantraniliprole, or can Defendant prove it uses a distinct and economically feasible non-infringing process?