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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 06/04/2026 has been entered.
Formal Matters
Receipt of Applicant’s response dated 06/04/2026 is acknowledged.
Claims 1-7 and 9-23 are pending.
Claim 8 is canceled.
Claim 1 is amended.
Claims 11-20 and 22-23 remain withdrawn from consideration as being drawn to a nonelected invention.
Claims 2 and 5-7 remain withdrawn from consideration as being drawn to nonelected species.
Claims 1, 3-4, 9-10, and 21 are under consideration in the instant Office action to the extent of the elected species, i.e., the at least one compound is a phenylisoxazoline compound of formula (1):
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REJECTION WITHDRAWN
Claim Rejections - 35 USC § 103
The rejection set forth in the Office action dated 03/16/2026 is hereby withdrawn in light of Applicant’s amendments to the claims and in favor of the new grounds of rejection set forth below.
NEW GROUNDS OF REJECTION
Claim Rejections - 35 USC § 112(a)
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 3-4, 9-10, and 21 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 1 has been amended to recite “An herbicidal composition, comprising…an oil-based liquid”. In Remarks dated 05/18/2026, it is stated that the amendments to claim 1 find support from Par. [0022] of the specification. However, Par. [0022] of the specification states that "The present composition is usually a formulation prepared by mixing the compound X and the compound Y with a carrier such as a solid carrier and a liquid carrier, and adding adjuvants for formulation such as surfactant as necessary. The formulation type is preferably an aqueous liquid suspension concentrate, an oil-based suspension concentrate, a wettable powder, a water dispersible granule, a granule, a water-based emulsion, an oil-based emulsion or an emulsifiable concentrate, and more preferably an emulsifiable concentrate.” This support in the disclosure regards formulation of the composition comprising a carrier such as a solid carrier and a liquid carrier and adjuvants such as surfactant and that the formulation may be of the types of an aqueous liquid suspension concentrate, an oil-based suspension concentrate, a wettable powder, a water dispersible granule, a granule, a water-based emulsion, an oil-based emulsion or an emulsifiable concentrate, but does not regard the composition comprising “an oil-based liquid”. Therefore, claim 1 is rejected for containing subject matter not described in the specification. Claims 3-4, 9-10, and 21 are rejected for depending from claim 1.
Amended claim 1 now recites limitation(s), which were not clearly disclosed in the specification as filed, and now change the scope of the instant disclosure as filed. Such limitation(s) recited in amended claim 1, which did not appear in the specification, as filed, introduces new concepts and violates the description requirement of the first paragraph of 35 U.S.C 112. Applicant is required to provide sufficient written support for the limitations recited in instant claim 1 in the specification or claims, as-filed, or remove these limitations from the claims in response to this Office Action.
Claim Rejections - 35 USC § 103
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.
Claims 1, 3-4, 9-10, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Trabold et al (WO 2020/114932, published on 06/11/2020 with an effective filing date of 12/02/2019, cited in IDS dated 05/10/2023, using its English equivalent US 2023/0032505 A1 also cited in IDS dated 05/10/2023) in view of Tohyama et al (US 2004/0254077 A1, published 12/16/2004, cited in Notice of References Cited dated 09/26/2025) as evidenced by PubChem (“Epyrifenacil”, accessed 09/16/2025, cited in Notice of References Cited dated 09/26/2025).
Trabold et al teach herbicidal compositions comprising herbicidally active compounds (A) and (B), where (A) represents one or more compounds of the general formula (I) or their agrochemically acceptable salts [component (A)],
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and (B) represents one or more herbicides [component (B)] (See entire document, e.g., Abstract).
Trabold et al teach a list of preferable compounds to be used as component (A), or agrochemically compatible salts thereof, wherein the list includes the following compounds A2, A3, and A5:
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(e.g., Table 1b, [0093]). The preferable compounds to be used as component (A) are listed by the chemical formula of the main component, this component being present in a chemical purity of preferably at least 95% by weight of the compound. The compounds can naturally also be used with lower purities. Especially when secondary components of the compounds consist entirely or predominantly of stereoisomers of the respective compounds (A), efficacies are achieved on application. Preferred herbicides (A) are therefore also mixtures of two or more compounds (A) according to the invention (e.g., [0095]). When the stereochemical orientation at a carbon atom is defined, the main component of the compound is a stereoisomer or stereoisomer mixture having the R or S configuration at the carbon atom in question (e.g., [0096]). If no stereochemistry is defined, the compound is a racemate. If there are multiple stereocenters and the configuration of each is identified as R or S, these are compounds having the stated stereochemistry at the centers in question (e.g., [0097]). If no R or S configuration is specified for multiple centers, the compounds are racemic mixtures, i.e. mirror-image stereoisomers (enantiomers of a pair of enantiomers) present therein are present in equal proportions in the mixture. Unless stated specifically the diastereomeric components are present approximately in equal proportions in the case of racemic compounds (A) having multiple stereocenters. For practical use, however, mixtures of diastereomers having different portions of the diastereomeric components exist in the case of racemic compounds having multiple stereocenters (e.g., [0098]). It is preferable here that the respective compounds listed are also present in a stereochemical purity of 60% to 100%, preferably 70-100%, especially 80% to 100% (e.g., [0099]).
Trabold et al teach that the one or more herbicides constituting component (B) may be selected from a list of suitable compounds, wherein the lists include ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (e.g., [0019]-[0030], specifically [0028]), which as evidenced by PubChem is epyrifenacil (See “2.4.2 Depositor-Supplied Synonyms” on Page 31).
Trabold et al teach that the herbicidal compositions can be combined with further herbicides, wherein the suitable further herbicides include dicamba and glyphosate, as well as all use forms, such as acids, salts, esters and isomers (e.g., [0486]-[0488]).
The compositions generally comprise from 0.1 to 99% by weight of active compounds of types (A) and/or (B) (e.g., [0589]).
The composition may additionally comprise further components, for example surfactants, and may be formulated as, for example, emulsions (EW), such as oil-in-water and water-in-oil emulsions (e.g., [0188], [0396]-[0397]).
Although Trabold et al teach that epyrifenacil is a suitable compound for use as an herbicide constituting component (B), Trabold et al do not teach a motivation for specifically selecting epyrifenacil from the list of suitable compounds.
This deficiency is made up for in the teaching of Tohyama et al.
Tohyama et al teach the following pyridine compound [d],
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, wherein R1 is a C1-C6 alkoxy group, R3 is a halogen atom, cyano group or nitro group, and R4 is a hydrogen atom or halogen atom, for which compound [d] has excellent herbicidal activity, and teach a process of preparing compound [d] (See entire document, e.g., Abstract). Tohyama et al teach 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(ethoxycarbonylmethoxy)pyridine, which as evidenced by PubChem is epyrifenacil (See “2.4.2 Depositor-Supplied Synonyms” on Page 8), as an exemplified compound [d] having excellent herbicidal activity, and teach a process of synthesizing it ( e.g., Example 2 in [0220]).
It would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to provide an herbicidal composition comprising at least one of A2, A3, and A5 as component (A), at least epyrifenacil as component (B), and comprising as further herbicides at least one of dicamba and glyphosate, as well as all use forms, such as acids, salts, esters and isomers, wherein the total amount of active compounds of types (A) and/or (B) is from 0.1 to 99% by weight, and wherein the composition is formulated as an oil-in-water emulsion or water-in-oil emulsion further comprising surfactant(s). One of ordinary skill in the art would have been motivated to use at least epyrifenacil as component (B) because Tohyama et al teach that epyrifenacil has excellent herbicidal activity and teach a process of synthesizing epyrifenacil, and there would have been a reasonable expectation of success in using at least epyrifenacil as component (B) because Trabold et al teach that epyrifenacil is a suitable compound for use as an herbicide constituting component (B).
The herbicidal composition of Trabold et al in view of Tohyama et al comprising at least one of A2, A3, and A5 as component (A) renders obvious the limitation of instant claim 1 of a phenylisoxazoline compound of formula (1) depicted on Page 2 of the Office action because each of compounds A2, A3, and A5 of Trabold et al are covered by the broader structure of a phenylisoxazoline compound of formula (1) depicted on Page 2 of the Office action which is not limited to a single stereoisomer or enantiomer.
The herbicidal composition of Trabold et al in view of Tohyama et al comprising at least one of A2, A3, and A5 as component (A) renders obvious the limitations of instant claim 3 because compound A3 of Trabold et al is the same compound as is recited in instant claim 3, i.e. (2R,4R)-4-({[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4,5-dihydroisoxazol-5-yl]carbonyl} amino)tetrahydrofuran-2-carboxylic acid methyl ester.
The herbicidal composition of Trabold et al in view of Tohyama et al comprising at least one of A2, A3, and A5 as component (A) renders obvious the limitations of instant claim 4 because although compound A3 of Trabold et al is a different isomer of the compound recited in instant claim 4, i.e. (2S,4S)-4-({[(5R)-3-(3,5-difluorophenyl)-5-vinyl-4,5-dihydroisoxazol-5-yl]carbonyl} amino)tetrahydrofuran-2-carboxylic acid methyl ester, stereoisomers are prima facie obvious. See Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007) (5(S) stereoisomer of ramipril obvious over prior art mixture of stereoisomers of ramipril.). Other structural similarities have been found to support a prima facie case of obviousness. See, e.g., In re May, 574 F.2d 1082, 1093-95, 197 USPQ 601, 610-11 (CCPA 1978) (stereoisomers). Generally, some teaching of a structural similarity will be necessary to suggest selection of the claimed species or subgenus. In Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007), the claims were drawn to the 5(S) stereoisomer of the blood pressure drug ramipril in stereochemically pure form, and to compositions and methods requiring 5(S) ramipril. The 5(S) stereoisomer is one in which all five stereocenters in the ramipril molecule are in the S rather than the R configuration. A mixture of various stereoisomers including 5(S) ramipril had been taught by the prior art. The question before the court was whether the purified single stereoisomer would have been obvious over the known mixture of stereoisomers. The record showed that the presence of multiple S stereocenters in drugs similar to ramipril was known to be associated with enhanced therapeutic efficacy. For example, when all of the stereocenters were in the S form in the related drug enalapril (SSS enalapril) as compared with only two stereocenters in the S form (SSR enalapril), the therapeutic potency was 700 times as great. There was also evidence to indicate that conventional methods could be used to separate the various stereoisomers of ramipril. The district court saw the issue as a close case, because, in its view, there was no clear motivation in the prior art to isolate 5(S) ramipril. However, the Federal Circuit disagreed, and found that the claims would have been obvious. The Federal Circuit cautioned that requiring such a clearly stated motivation in the prior art to isolate 5(S) ramipril ran counter to the Supreme Court’s decision in KSR, and the court stated requiring an explicit teaching to purify the 5(S) stereoisomer from a mixture in which it is the active ingredient is precisely the sort of rigid application of the TSM test that was criticized in KSR.
Because Trabold et al teach that each of compounds A2, A3, and A5 represent the main component present wherein the secondary components include the stereoisomers of the main component and that for racemic compounds having multiple stereocenters the diastereomeric components are present approximately in equal proportions, the herbicidal composition of Trabold et al in view of Tohyama et al comprising at least one of A2, A3, and A5 as component (A) also renders obvious the limitations of instant claim 21.
Regarding the required range of weight ratio of epyrifenacil to the phenylisoxazoline compound being from 1:0.5 to 1:4 of instant claim 1, the herbicidal composition of Trabold et al in view of Tohyama et al comprising a total amount of active compounds of types (A) and/or (B) from 0.1 to 99% by weight necessarily overlaps the recited weight ratio requirement of instant claim 1. A prima facie case of obviousness typically exists when the ranges of a claimed composition overlap the ranges disclosed in the prior art (In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003)).
Thus, the herbicidal composition of Trabold et al in view of Tohyama et al renders obvious instant claims 1, 3-4, 9-10, and 21.
Response to Applicant’s Arguments
Applicant’s arguments filed on 05/18/2026 have been considered.
Applicant argues that with the amendments to claim 1, the unexpected results submitted in the declaration under 37 CFR 1.132 dated 12/26/2025 are now commensurate in scope with the present claims.
The above argument has been fully considered by the Examiner but is not found persuasive because the composition in the declaration and the composition of instant claim 1 are still not commensurate in scope, e.g., instant claim 1 allows for any “oil-based liquid” and any “surfactant” whereas the composition of the declaration comprises specifically DMF and Tween 20, respectively. Further, if each of “an oil-based liquid” and “a surfactant” are not limited to DMF and Tween 20, respectively, the interchangeability of DMF with at least one different oil-based liquid and the interchangeability of Tween 20 with at least one different surfactant should be established. Additionally, the criticality of the weight ratio range recited in instant claim 1 has not been established. Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). The Examiner additionally notes that amended claim 1 is still taught by the prior art as Trabold et al teach the inclusion of surfactants and oils (See new grounds of rejection under 35 USC 103 above).
Conclusion
No claims are allowable.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KAELEIGH ELIZABETH OLSEN whose telephone number is (703)756-1962. The examiner can normally be reached M-F 8-5 PM.
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/K.E.O./Examiner, Art Unit 1619
/NICOLE P BABSON/Primary Examiner, Art Unit 1619
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