Fungicidal compositions

Patent No. US9314022 (titled "Fungicidal compositions") on Sep 19, 2013. The application was issued on Apr 19, 2016.

What is this patent about?

’022 is related to the field of agricultural chemistry, specifically focusing on fungicidal compositions designed to protect crops from phytopathogenic diseases. The background context involves the increasing threat of aggressive fungal infections, such as soybean rust caused by Phakopsora pachyrhizi, which have historically led to significant yield losses. Traditional fungicides often fall short in terms of crop tolerance or raw efficacy against these specific pathogens, necessitating more potent and broader-spectrum chemical solutions.

The underlying idea behind ’022 is the discovery of a powerful synergistic interaction between a specific class of pyrazole-4-carboxylic acid amides and established fungicidal agents. By combining a benzonorbornene derivative—characterized by a dihalomethylidene group at the 9-position—with secondary fungicides like azoles, the inventors found they could achieve a level of pathogen control that exceeds the purely additive effects of each chemical used alone. This synergy allows for lower application rates while simultaneously broadening the range of fungi that can be effectively suppressed.

The claims of ’022 focus on compositions that pair a compound of Formula I, where the pyrazole ring is substituted with a difluoromethyl or trifluoromethyl group, with at least one azole fungicide. The independent claims specifically protect the use of these mixtures in synergistically effective amounts. Particular emphasis is placed on combinations where the primary compound is 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-difluoromethylidene-benzonorbornene-5-yl) amide, used alongside specific azoles such as cyproconazole, propiconazole, or tebuconazole.

In practice, the invention works by applying these multi-component mixtures to plants, seeds, or the surrounding soil to inhibit or destroy fungal microorganisms. The composition can be delivered through various agricultural formats, including emulsifiable concentrates, suspension concentrates, or seed dressings. The mechanism relies on the complementary modes of action provided by the pyrazole amide and the azole partner, which together disrupt the life cycle of fungi like powdery mildew, rusts, and molds more effectively than prior art treatments.

This approach differentiates itself from previous solutions by specifically addressing the high-resistance profiles of modern pathogens like Asian soybean rust. While prior tricyclic amine derivatives showed some biological activity, the ’022 compositions provide a documented super-additive effect (calculated via the Colby formula) that enhances degradability and plant vigor. By optimizing the weight ratios between the pyrazole amide and the azole, the invention provides a more robust defense system for high-value crops compared to the single-agent applications common in earlier agricultural practices.

How does this patent fit in bigger picture?

Technical Landscape

In the late 2000s when ’022 was filed, the protection of crops against phytopathogenic fungi was typically implemented using single-active ingredient fungicidal agents from established chemical classes such as azoles or strobilurins. At a time when agricultural systems commonly relied on these conventional treatments, the emergence of highly aggressive pathogens, such as Phakopsora pachyrhizi in soybean cultures, made effective disease management non-trivial due to the limited action or insufficient crop tolerance of existing solutions. Hardware and software constraints in the era's precision application systems further necessitated the development of highly potent chemical mixtures that could achieve broad-spectrum control at lower total application rates.

Prosecution Position

The disclosed invention represents a meaningful technical advancement through the integration of a specific tricyclic amine derivative—a pyrazole-4-carboxylic acid benzonorbornene-5-yl amide—with a secondary fungicidal or insecticidal component to create a synergistic composition. This architectural shift from single-agent applications to specific binary or ternary mixtures enables a super-additive fungicidal effect, where the combined activity exceeds the sum of the individual components' performance. This capability allows for the effective control of a wider spectrum of pathogens, particularly soybean rust, while simultaneously overcoming the technical constraint of high application rates by maintaining efficacy at lower concentrations of active ingredients.

Claims

The patent contains a total of 23 claims, with claims 1, 16, and 17 serving as the independent claims. These independent claims focus on synergistic fungicidal compositions comprising a specific pyrazole-4-carboxylic acid compound combined with various azole fungicides to control phytopathogenic diseases. The dependent claims serve to further narrow the chemical structures of the primary components, specify particular azole selections, define effective weight ratios, and outline methods for applying these compositions to protect plants and crops, such as soybeans, from fungal pathogens.

Key Claim Terms New

Definitions of key terms used in the patent claims.

Term (Source)Support for SpecificationInterpretation
3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-difluoromethylidene-benzonorbornene-5-yl) amide
(Claim 17)
A preferred embodiment of the invention is represented by those compositions which comprise as component A) a compound of formula (I), wherein R1 is difluoromethyl. Further preferred compounds of formula (I) are: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-difluoromethylidene-benzonorbornene-5-yl)amide (compound A-1.2). Example 5 illustrates the preparation of 9-difluoromethylidene-5-nitro-benzonorbornene, a precursor for this compound.A specific pyrazole amide compound identified as Compound A-1.2, used as the primary active component (A).
Azole fungicide
(Claim 1, Claim 16, Claim 17)
An azole fungicide selected from azaconazole (40), bromuconazole (96), cyproconazole (207), difenoconazole (247), diniconazole (267), diniconazole-M (267), epoxiconazole (298), fenbuconazole (329), fluquinconazole (385), flusilazole (393), flutriafol (397), hexaconazole (435), imazalil (449), imibenconazole (457), ipconazole (468), metconazole (525), myclobutanil (564), oxpoconazole (607), pefurazoate (618), penconazole (619), prochloraz (659), propiconazole (675), prothioconazole (685), simeconazole (731), tebuconazole (761), tetraconazole (778), triadimefon (814), triadimenol (815), triflumizole (834), triticonazole (842), diclobutrazol (1068), etaconazole (1129), furconazole (1198), furconazole-cis (1199) and quinconazole (1378).A class of fungicidal compounds characterized by a five-membered nitrogen-containing ring, used as component (B) in the composition.
Compound of formula I
(Claim 1, Claim 16, Claim 17)
The compounds of formula I occur in two different stereoisomers, which are described as the single enantiomers of formulae I_I and I_II. The invention covers all such stereoisomers and mixtures thereof in any ratio. According to the invention 'racemic compound of formula (I)' means a racemic mixture of compounds of formula I_I and I_II.A pyrazole-4-carboxylic acid benzonorbornene amide derivative where R1 is a difluoromethyl or trifluoromethyl group and X is a chloro, fluoro, or bromo substituent.
Synergistically effective amount
(Claim 1, Claim 16, Claim 17)
A synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components. This synergistic activity is apparent from the fact that the fungicidal activity of the composition comprising component (A) and component (B) is greater than the sum of the fungicidal activities of component (A) and of component (B). The action to be expected E for a given active ingredient combination obeys the so-called COLBY formula.An amount of active ingredients (A) and (B) that produces a biological effect greater than the sum of the individual effects of each component.

Litigation Cases New

US Latest litigation cases involving this patent.

Case NumberFiling DateTitle
1:25-cv-01520Sep 11, 2025SYNGENTA CROP PROTECTION AG v. UPL Limited
3:25-cv-00735Sep 11, 2025Syngenta Crop Protection AG v. UPL Limited, et al.

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US9314022

Application Number
US14031538A
Filing Date
Sep 19, 2013
Publication Date
Apr 19, 2016
External Links
Slate, USPTO , Google Patents