DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Summary
Receipt of Applicant's Remarks and Election filed on 05/29/2026 is acknowledged.
Claim 1-18 and 20 are pending.
Claims 9–10, 15–16, and 19 are withdrawn from consideration. Claim 20 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being directed to a nonelected invention.
Priority
The current application filed on 02/20/2024 is a 371 of PCT/EP2022/073602 filed 08/24/2021, which in turn claims priority to patent application EP21193044.1 filed on 08/25/2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 02/20/2024 is in compliance with the provisions of 37 CFR 1.98. Accordingly, the information disclosure statements has been considered by the examiner. Signed copies have been attached to this office action.
Election/Restrictions
Applicant's response to the Restriction Requirement filed on May 29, 2026, is acknowledged. Applicant elects Group I (claims 1–18 and Species A, wherein X is a bond and Y is Z) with traverse. Group II, claim 20 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
The traverse has been considered but is overruled. The restriction between Group I (products/compositions, claims 1–18) and Group II (method of use, claim 20) is maintained because the claimed method of use is not coextensive with the compound claims and represents a distinct statutory class of invention requiring a separate search profile directed to herbicidal methods of vegetation control.
The examiner has complied with MPEP § 1893.03(d) by identifying the compound of formula (I) as the common structural unit of claims 1–18 and explaining that claim 20, which requires applying that compound to a plant or its habitat, introduces a distinct functional and operational dimension not present in the compound/composition claims. Although Applicant contends that the method claim shares a common special technical feature with the compound claims under PCT Rule 13, the examiner finds that the method claim cannot be searched without a separate examination of herbicidal activity parameters, formulation delivery, and agronomic application conditions not disclosed or required by the compound claims alone. The restriction is therefore maintained as proper under 37 CFR 1.141 and MPEP § 806.05(e). See MPEP § 1893.03(d).
The traverse on species is overruled. Elected Species Group A (X = bond; Y = Z) is structurally and chemically distinct from Species Group B (X = divalent unit X¹; Y = substituted alkyl) and Species Group C (X-Y forming a fused bicyclic lactone or ester system defined by formulas XY1 and XY2). Each species group requires an independent search in non-overlapping structural spaces: Species A requires examination of carbocyclic and heterocyclic ring systems directly pendant to the amide nitrogen via a single bond; Species B requires examination of open-chain alkyl tethers bearing functional groups appended through a divalent X linker; and Species C requires examination of fused bicyclic lactone/ester architectures wherein the X and Y units together form a bridging cyclic group. These structural environments are sufficiently distinct that no single prior art reference or combination of references would anticipate or render obvious compounds in all three groups simultaneously.
Applicant's contention that Species Group C merely presents an alternative depiction of Species A and Species B is noted but unpersuasive. While Applicant correctly observes that certain XY1 and XY2 structures can be read as encompassing a ring Z directly attached via a bond (Species A) or via a divalent X¹ linker (Species B), the operative claim language of claims 15 and 16 expressly defines the X-Y combination as forming a fused bicyclic group through the mandatory ring-forming relationship between paired substituents (Rᴬ/Rᶜ or Rᶜ/Rᴸ, etc.). This structural requirement — that X and Y together constitute a ring system rather than a pendant substituent — is not present in elected Species A, where X is explicitly a bond and Y is a separate ring Z. The structural search space for claims 15 and 16 is accordingly distinct. The restriction as to species is maintained as proper.
Claims 1–8, 11–14, and 17–18 are examined to the extent they read on elected Species Group A. Claims 9–10 are withdrawn from consideration as being directed exclusively to non-elected Species Group B. Claims 15–16 are withdrawn from consideration as being directed to non-elected Species Group C.
Claims 1–8, 11–14, and 17–18 are pending and under examination in this application.
The election is made FINAL.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1 and 12 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 - Variables m, n, and p (Antecedent Basis): recites within the definitions of variables R7, R8, R10, R11, and R12 - R15, Y and Z, that these radicals are “each substituted by m radicals,” contain “n nitrogen/sulfur/oxygen atoms,” bear “n oxo groups,” or are substituted by “p radicals.” The numerical variables m, n, and p are first encountered as operational modifiers embedded within complex multi-layered structural definitions before any antecedent definition is provided. The separate clauses subsequently defining “each m is independently 0, 1, 2, 3, 4, or 5,” “each n is independently 0, 1, or 2,” and “each p is independently 1, 2, or 3” do not cure this deficiency because they appear only after the variables have been deployed as stoichiometric controls over substitution count and heteroatom count across multiple distinct structural environments. Because m, n, and p govern the absolute number of substituents and heteroatoms at each occurrence independently, the lack of a foundational antecedent basis renders the metes and bounds of the claimed chemical space indeterminate. See MPEP § 2173.05(e).
Claim 1 further presents ambiguity of variable “R’”: Within the definition of variable Y, the claim recites substituents selected from a group including “R’.” Within the separate definition of variable Z, the claim again recites substituents including “R’.” A subsequent clause defines “each R’ is independently (C₁–C₃)-alkyl or (C₁–C₃)-alkoxy.” The use of an identical prime-symbol variable (R’) across both the Y and Z sub-definitions, combined with its potential confusion with the primary preamble substituent R¹, renders the chemical identity of R’ structurally ambiguous. It cannot be determined with reasonable certainty whether R’ is a newly introduced variable, an alias for R¹, or a drafting error. Because the same symbol is used to potentially mean different structural entities in different structural contexts within the same claim, the metes and bounds of the chemical space encompassed by claims incorporating Y or Z cannot be determined. A person of ordinary skill in the art would be unable to ascertain the scope of the claim with reasonable certainty. See Nautilus, Inc. v. Biosig Instruments, Inc., 572 U.S. 898 (2014); MPEP § 2173.05(e). If R’ was intended to reference R¹ as defined in the preamble, the non-standard notation is inadequate to establish that identity.
Claim 12- Internal Variable Contradiction: Claim 12 introduces a subordinate definition for the case where X is a divalent unit X¹, stating that Y is (C₁–C₄)-alkyl substituted by p radicals from a specific list. Within that list, the claim specifies “Rᵇ in CO₂Rᶜ” and “Rᶜ in CONRᵇRʰ.” This creates a direct structural contradiction: the functional group CO₂Rᶜ does not contain a variable Rᵇ, and the functional group CONRᵇRʰ does not contain a variable Rᶜ. No reasonable construction can reconcile these internally contradictory variable cross-references, and the claim is therefore uninterpretable as written. A person of ordinary skill in the art could not ascertain which variable is intended to occupy which position within the respective functional groups, rendering the metes and bounds of claim 12 indeterminate. See Nautilus, Inc. v. Biosig Instruments, Inc., 572 U.S. 898 (2014); IPXL Holdings, L.L.C. v. Amazon.com, Inc., 430 F.3d 1377 (Fed. Cir. 2005).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1–8, 11–14, and 17–18 are rejected under 35 U.S.C. 103 as being unpatentable over Harris (US 3,072,473) in view of Carter et al. (WO 2004/098512 A2) hereinafter the reference is referred to as “Carter”.
Harris discloses N,N′-diarylmalonamides and related N-alkyl-N-arylmalonamic acid derivatives that exhibit herbicidal and plant growth regulating activity. Harris teaches a core malonamide scaffold of formula (I)-type architecture in which an aryl or substituted aryl group (including phenyl and naphthyl rings) is attached to each amide nitrogen of the central propanediamide unit. Harris explicitly discloses aryl ring substituents including hydrogen, halogen, and lower alkyl groups at various ring positions (col. 2, lines 10–35). Harris identifies the unsubstituted central malonyl carbon (R⁷, R⁸ = H) as its operative baseline and does not disclose gem-disubstitution at the central carbon with alkyl groups. Harris further does not disclose a terminal ring Z bearing a carboxylate or ester functional group (-CO₂Rᵉ).
Carter discloses a broad class of malonamide and malonamide derivative compounds as modulators of chemokine receptor activity, particularly CCR2. Carter teaches malonamide compounds of general formula comprising an N-aryl substituted left-side amide nitrogen, a central malonyl unit bearing gem-dialkyl substitution (R⁷, R⁸ = alkyl, including methyl), and a right-side amide nitrogen connected via an optional divalent X linker or direct bond to a pendant carbocyclic or heterocyclic ring Y/Z. Critically, Carter explicitly discloses carbocyclic ring systems bearing carboxylate ester substituents (-CO₂Rᵉ) as pendant functionality on the terminal Y ring (see, e.g., claims 1, 8, and 9, and representative examples throughout the specification). Carter thus teaches the two specific structural features absent from Harris: (1) gem-dialkyl substitution at the central malonyl carbon and (2) ester/carboxylate functionalization on the terminal carbocyclic ring Z.
Regarding claim 1, the claim recites a compound of formula (I) comprising a left-side N-aryl phenyl ring bearing substituents R¹–R⁶, a central malonyl carbon bearing R⁷ and R⁸, a right-side nitrogen bearing R⁹, a divalent linker X (or bond), and terminal group Y (which in elected Species A is ring Z). Harris discloses the core malonamide architecture of formula (I), including N-phenyl substitution on the left-side amide nitrogen with ring substituents including hydrogen, halogen, and alkyl at positions corresponding to R²–R⁶, and a right-side amide nitrogen connected via a bond (X = bond) to an aromatic ring system corresponding to Y/Z (col. 1, lines 15–40; col. 2, lines 10–35). Harris sets R⁹ = H throughout its exemplified compounds. Harris does not disclose gem-dialkyl substitution at the central malonyl carbon (R⁷, R⁸ = alkyl) or a terminal ring Z bearing a carboxylate ester group (-CO₂Rᵉ). Carter discloses malonamide compounds of the same core scaffold in which the central malonyl carbon bears gem-dialkyl substituents, including gem-dimethyl (R⁷ = R⁸ = methyl) and mixed alkyl combinations. Carter further discloses terminal carbocyclic rings bearing carboxylate ester groups (-CO₂Rᵉ) as pendant ring substituents (claims 1, 8–9; representative examples). These structural features map directly onto the R⁷/R⁸ alkyl limitation and the Z ring CO₂Rᵉ substitution requirement of elected Species A.
It would have been obvious to a person of ordinary skill in the art to modify the herbicidal malonamide scaffold of Harris by introducing gem-dialkyl substitution at the central malonyl carbon and a carboxylate ester on the terminal carbocyclic ring, as taught by Carter, to arrive at the compounds of claim 1. A skilled artisan seeking to optimize the metabolic stability, lipophilicity, and soil persistence of Harris’s herbicidal malonamides would have recognized that gem-dialkyl substitution at the central carbon is a well-established medicinal chemistry strategy for blocking enzymatic hydrolysis at the flanking amide bonds — a principle directly applicable to improving the rain-fastness and residual activity of field herbicides. Carter provides an explicit, enabling disclosure of this gem-dialkyl malonamide motif applied to compounds sharing the identical N-aryl malonamide backbone, giving the skilled artisan a concrete structural template and synthetic precedent for making this modification to Harris’s herbicidal scaffold. The incorporation of a terminal ring ester (-CO₂Rᵉ) is further motivated by the recognized utility of carboxylate groups in tuning the soil mobility, plant uptake, and systemic herbicidal activity of agrochemical compounds, and Carter confirms that this functional group is fully compatible with the malonamide scaffold and synthetically accessible. One of ordinary skill in the art would have had a reasonable expectation of success in combining these known structural modifications to produce compounds of formula (I) as recited in claim 1. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398 (2007).
Regarding claims 2-3, the dependent claims further narrow the definition of substituents on the left-side phenyl ring (R¹–R⁶). Claim 2 requires one or more of: (a) R¹ and R⁹ are hydrogen; (b) R² and R⁶ are hydrogen, halogen, or (C₁–C₃)-alkyl; (c) R³ and R⁵ are hydrogen, halogen, (C₁–C₃)-alkyl, haloalkyl, alkoxy, or haloalkoxy; and (d) R⁴ is hydrogen or halogen. Claim 3 further narrows these definitions to smaller halogen/hydrogen/small alkyl selections. Harris discloses N,N′-diarylmalonamides wherein both amide nitrogens are substituted by phenyl or substituted phenyl rings. Harris exemplifies aryl ring substituents including hydrogen, halogen (chloro, bromo), and lower alkyl (methyl) at various ring positions (col. 2, lines 10–35), which map directly onto conditions (a)–(d) of claims 2 and 3. R¹ = H (nitrogen lacks additional N-substituent beyond the aryl ring) is Harris’s standard amide nitrogen configuration. The narrowed ring substitution patterns of claims 2 and 3 thus fall within the structural scope explicitly disclosed by Harris.
Regarding claims 4, 5, and 6, these claims progressively narrow the definition of R⁷ and R⁸ at the central malonyl carbon. Claim 4 requires R⁷ and R⁸ to be independently (C₁–C₆)-alkyl or (C₂–C₆)-alkenyl. Claim 5 further requires R⁷ and R⁸ to be (C₁–C₄)-alkyl. Claim 6 requires R⁷ and R⁸ to both be methyl. Harris discloses malonamide compounds wherein R⁷ = R⁸ = H (unsubstituted central carbon) as the operative baseline but does not disclose gem-alkyl substitution at this position. Carter explicitly teaches gem-dialkyl substitution at the central malonyl carbon across a range of alkyl group sizes, including gem-dimethyl (C₁), gem-diethyl (C₂), and mixed lower alkyl combinations (see Carter, claims 1 and 8; specification examples). The gem-dimethyl central carbon species required by claim 6 is among the most specifically and repeatedly exemplified in Carter. The progressive narrowing of claims 4–6 is fully anticipated by Carter’s explicit disclosure of these alkyl substitution patterns applied to the same malonamide backbone. It would have been obvious to apply Carter’s gem-dialkyl motif, particularly the gem-dimethyl species, to Harris’s herbicidal scaffold. See In re Aller, 220 F.2d 454 (CCPA 1955) (where the prior art teaches a general condition, specific selections within that range are prima facie obvious).
Regarding claims 7-8, claim 7 requires X = bond and Y = Z, where Z is a three- to six-membered saturated, partly unsaturated, or fully unsaturated carbocyclic or oxygen-containing heterocyclic ring substituted by p radicals from the group including CO₂Rᵉ, CONRᵇRʰ, S(O)ⁿ Rᵃ, and related polar functional groups. Claim 8 further narrows Z to a five- or six-membered saturated or partly unsaturated carbocyclic ring substituted by p radicals CO₂Rᵉ, where Rᵉ is hydrogen or (C₁–C₆)-alkyl. Harris discloses malonamide compounds wherein X is a bond and Y is a cyclic ring system Z (aryl or substituted aryl) directly appended to the amide nitrogen, establishing this X=bond/Y=Z structural architecture. Harris’s terminal rings, however, carry only simple halogen, alkyl, or hydrogen substituents and do not disclose the CO₂Rᵉ ester or the broad polar functional group substitution pattern required by claim 7. Carter explicitly teaches pendant carbocyclic ring systems, including five- and six-membered rings (cyclopentyl, cyclohexyl, and related partially unsaturated analogs), bearing carboxylate ester groups (-CO₂Rᵉ) as ring substituents (Carter, claims 8–9; specification examples). Carter’s disclosure of carbocyclic rings functionalized with CO₂Rᵉ maps directly onto the Z ring limitations of claims 7 and 8. It would have been obvious to apply Carter’s terminal ring functionalization to Harris’s herbicidal X=bond/Y=Z framework to arrive at the compounds of claims 7 and 8.
Regarding claims 11, 13, and 14, claim 11 requires p = 1 or 2. Claims 13 and 14 are progressively narrowed species claims under claim 12, defining specific combinations of R¹–R⁹ (all hydrogen or small halogen/alkyl), R⁷ = R⁸ = (C₁–C₄)-alkyl or methyl specifically, X = bond with Y = Z as a five-membered partly unsaturated carbocyclic ring bearing one CO₂Rᵉ substituent, or X = X¹ divalent unit with Y = (C₁–C₄)-alkyl bearing one CO₂Rᵉ group (claim 13); and X = bond with Y = Z as a five-membered partly unsaturated carbocyclic ring bearing one CO₂Rᵉ with Rᵉ = (C₁–C₄)-alkyl (claim 14). The substitution patterns of the left-side phenyl ring recited in claims 13 and 14 are fully encompassed by Harris’s disclosed aryl substitution scope. The gem-dialkyl (specifically gem-dimethyl) central carbon of claims 13 and 14 is explicitly taught by Carter. The five-membered partly unsaturated carbocyclic ring Z bearing one CO₂Rᵉ group is among the specific terminal ring structures exemplified in Carter. The combination of these elements across claims 11, 13, and 14 would have been obvious over Harris in view of Carter for the reasons stated above with respect to claims 1 and 7–8. Regarding p = 1 specifically (claim 11, claim 13, and claim 14), Carter’s representative compounds include monosubstituted carbocyclic rings bearing a single CO₂Rᵉ group, directly satisfying this limitation.
Regarding Claim 12, as noted in the § 112(b) rejection above, claim 12 contains internally contradictory variable cross-references that render it indefinite (referencing Rᵇ within CO₂Rᶜ and Rᶜ within CONRᵇRʰ). To the extent claim 12 can be given a reasonable construction consistent with the specification, and to the extent it is examined on the merits, the broadly recited malonamide structural features of claim 12 that define the elected species (central gem-dialkyl carbon; terminal carbocyclic ring bearing CO₂Rᵉ) are taught by the combination of Harris and Carter for the reasons provided above with respect to claim 1.
Regarding claims 17 and 18, claim 17 recites a composition comprising at least one compound of claims 1–16 and at least one auxiliary customary for formulating crop protection compounds. Claim 18 further requires the composition to comprise a further herbicide. Harris explicitly discloses that its malonamide herbicidal compounds are formulated into active agricultural compositions using standard liquid or solid carriers, surface-active agents, and adjuvants customary for crop protection and vegetation control, including wettable powders, emulsifiable concentrates, and granular matrices adapted for field application (col. 4, lines 45–72). It would have been entirely obvious to a person of ordinary skill in the art to formulate the structurally optimized malonamide compound resulting from the combination of Harris and Carter into a standard herbicidal composition using the routine agricultural auxiliaries taught by Harris. The inclusion of a further herbicide in a mixed herbicidal formulation (claim 18) is a routine formulation practice explicitly contemplated by Harris and represents no inventive step beyond the combination of the references.
Prima Facie Case of Obviousness
A prima facie case of obviousness has been established based on the combination of Harris and Carter. The claimed compounds of formula (I) in elected Species A differ from the most closely related compounds of Harris solely in (1) the presence of gem-dialkyl substituents at the central malonyl carbon (R⁷, R⁸) and (2) the substitution of the terminal carbocyclic ring Z with a carboxylate ester group (-CO₂Rᵉ). Both of these structural modifications are explicitly and specifically taught by Carter as applied to the same N-aryl malonamide backbone. The combination applies known modifications (gem-dialkylation for metabolic stabilization; terminal ring esterification for physicochemical property tuning) to a known herbicidal scaffold to achieve predictable structural results. No unexpected properties have been demonstrated.
Response to Applicant's Arguments
Applicant argues in the response dated May 29, 2026, that a skilled artisan would not combine Harris and Carter (WO ’512) because these references belong to totally different technical fields — Harris relating to plant growth regulants and herbicides, while Carter discloses malonamides as modulators of chemokine receptor activity for pharmacological use in humans. Applicant further argues that a skilled person would not consider a structural motif described for pharmacological use to modify herbicidal compounds. This argument is unpersuasive for the following reasons.
First, the motivation to combine prior art references does not require that the references originate from the same field of use. Under KSR International Co. v. Teleflex Inc., 550 U.S. 398, 418 (2007), a person of ordinary skill is “a person of ordinary creativity, not an automaton,” who “looks at the references available and can identify a reason to combine them.” The relevant question is whether a skilled artisan would have been motivated to look to Carter’s structural teachings when seeking to improve the malonamide scaffold of Harris — not whether Carter was designed as a herbicide. See In re Beattie, 974 F.2d 1309, 1312 (Fed. Cir. 1992) (“As long as some motivation or suggestion to combine the references is provided by the prior art taken as a whole, the law does not require that the references be from the same field of endeavor.”).
Second, and critically, the malonamide scaffold itself is the shared technical feature bridging the two references. Harris and Carter do not disclose different compound classes — they disclose the same compound class (N,N′-diarylmalonamide derivatives) applied to different utilities. A person of ordinary skill in synthetic or agricultural chemistry, seeking to modify the Harris malonamide scaffold at the central malonyl carbon or at the terminal ring to improve stability, activity, or physicochemical properties, would necessarily survey the broader malonamide chemical literature, which includes Carter. The fact that Carter uses its compounds as chemokine receptor modulators does not diminish the relevance of its structural teachings: a gem-dialkyl group at the central carbon and a CO₂Rᵉ group on a terminal carbocyclic ring are structural features of the molecule, not pharmacological properties. Those structural features are fully transferable to a herbicidal context.
Third, gem-dialkyl substitution at a central carbon flanked by two amide bonds is a well-known medicinal and agrochemical strategy to confer metabolic stability by sterically blocking hydrolysis at the adjacent carbonyl bonds. The motivation to apply this modification to improve the field performance of Harris’s herbicides would have been immediately apparent to a skilled agrochemical researcher reviewing the malonamide literature — including Carter — without any requirement of pharmacological interest in chemokine biology.
Accordingly, Applicant’s argument that the technical field divergence between Harris and Carter renders the combination non-obvious is unpersuasive. The combination is motivated by the shared malonamide scaffold, by the routine agrochemical rationale for each individual structural modification, and by the predictable structural and synthetic outcome of their combination. The rejection is maintained.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANDRE MACH whose telephone number is (571)272-2755. The examiner can normally be reached 0800 - 1700 M-F.
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/ANDRE MACH/Examiner, Art Unit 1615
/Robert A Wax/Supervisory Patent Examiner, Art Unit 1615
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