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 .
Formal Matters
Receipt of Applicant’s response, dated 12/26/2025, is acknowledged.
Claims 1-7 and 9-23 are pending.
Claim 8 is canceled.
Claim 23 is new.
Claims 1, 3-4, 9-10, and 21 are amended.
Claims 11-20 and 22 remain withdrawn from consideration as being drawn to a nonelected invention.
Claims 2 and 5-7 remain withdrawn from consideration as being drawn to nonelected species.
New claim 23 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claims 1, 3-4, 9-10, and 21 are being examined 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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OBJECTIONS/REJECTIONS WITHDRAWN
Specification
The objections to the abstract and to the specification set forth in the Office action dated 09/26/2025 are hereby withdrawn in light of Applicant’s amendments to the abstract and to the specification.
Claim Objections
The objection to claim 1 set forth in the Office action dated 09/26/2025 is hereby withdrawn in light of Applicant’s amendments to the claims.
Claim Rejections - 35 USC § 112(b)
The indefiniteness rejections of claims 9-10 set forth in the Office action dated 09/26/2025 is hereby withdrawn in light of Applicant’s amendments to the claims.
Claim Rejections - 35 USC § 103
The obviousness rejection of claims 1, 3-4, 8-10, and 21 over Trabold et al in view of Tohyama et al set forth in the Office action dated 09/26/2025 is hereby withdrawn in light of Applicant’s amendments to the claims and in favor of the new grounds of rejection set forth below as necessitated by Applicant’s amendments to the claims.
NEW GROUNDS OF REJECTION
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]).
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. 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 renders obvious instant claims 1, 3-4, 9-10, and 21.
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)).
Response to Applicant’s Arguments
Applicant’s arguments filed on 12/26/2025 have been considered.
Applicant argues that Tohyama is not analogous art because Tohyama is not in the same field of endeavor. Applicant argues, regarding the first test defining the scope of analogous art i.e. “whether the art is from the same field of endeavor, regardless of the problem addressed”, that Tohyama focuses on producing a single pure compound and not on compositions and the field of invention of Tohyama is in organic synthetic chemistry of pyridine compounds, where on the other hand, the field of the present application is herbicidal compositions for controlling weeds and not directed to a process for synthesizing compounds and, therefore, the field of endeavor of Tohyama is not the same as that of the claimed invention. Applicant argues, regarding the second test defining the scope of analogous art i.e. “if the reference is not within the field of the inventor’s endeavor, whether the reference still is reasonably pertinent to the particular problem with which the inventor is involved”, that Tohyama is not related to the problem to be solved by the present claims, i.e., the present application is directed to providing an herbicidal composition with an excellent weed controlling effect and the problem addressed by Tohyama “is to provide a beneficial process for producing the pyridine compounds [d] having a specific pattern of substituents and starting compounds for the process”, and thus, the objective of Tohyama and the problem it seeks to solve is not reasonably pertinent to the present application. Applicant argues that Tohyama only teaches that epyrifenacil has excellent herbicidal activity and discloses a process of synthesizing epyrifenacil, which is merely general information/background knowledge without specific guidance leading to the claimed invention and therefore, Tohyama does not supply sufficient teaching to support an obviousness rejection.
The above arguments have been fully considered by the Examiner but are not found persuasive because, firstly, "same field of endeavor" and "reasonably pertinent" are two separate tests for establishing analogous art; it is not necessary for a reference to fulfill both tests in order to qualify as analogous art. See Bigio, 381 F.3d at 1325, 72 USPQ2d at 1212. See MPEP 2141.01(a). As can be seen above, the rejection under 35 USC 103 applied in the instant Office action relies on the teaching of Trabold et al in view of Tohyama et al, for which the teaching of Trabold et al is in the same field of endeavor as the present application i.e. herbicidal compositions for controlling harmful plants (Trabold et al) and herbicidal compositions for controlling weeds (present application) and the teaching of Tohyama et al is reasonably pertinent to the problem of the present application, i.e. excellent herbicidal activity (Tohyama et al) and excellent weed controlling effect (present application). From Trabold et al, which teach that epyrifenacil is a suitable compound for use as an herbicide constituting component (B) alongside a list of other suitable compounds, a person of ordinary skill in the art would have been motivated to look to the teaching of Tohyama et al and select epyrifenacil as component (B) because Tohyama et al teach that epyrifenacil has excellent herbicidal activity and teach a process of synthesizing epyrifenacil. Regarding the argument of Tohyama “not supplying sufficient teaching to support an obviousness rejection”, the Examiner reminds Applicant that the instant rejection is based on the combined teachings of Trabold et al and Tohyama et al and not the individual teaching of Tohyama et al. Applicant is reminded that the reason or motivation to modify the reference may often suggest what the inventor has done, but for a different purpose or to solve a different problem. It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by applicant. See, e.g., In re Kahn, 441 F.3d 977, 987, 78 USPQ2d 1329, 1336 (Fed. Cir. 2006). Further, Applicant is reminded that one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
Applicant argues unexpected results of the composition of the instant claims that would not be expected from the combination of Trabold and Tohyama and these unexpected improvements distinguish the invention as non-obvious over the prior art. Applicant points to a submitted Declaration under 37 CFR 1.132 which Applicant argues shows the herbicidal effects of epyrifenacil and “icafolin-methyl” being applied individually or in combination.
The above arguments have been fully considered by the Examiner but are not found persuasive because, in the declaration the composition argued to be that of the instant claims is not commensurate in scope with the composition of instant claim 1, i.e., Page 2 of the declaration states that the sample compositions are “Epyrifenacil spray liquid, which was prepared by diluting an emulsifiable concentrate of epyrifenacil with water”, Icafolin-methyl spray liquid, which was prepared by diluting an experimental formulation consisting of icafolin-methyl (8 parts), DMF (1000 parts), and Tween20 (20 parts) with water”, and “Mixtures of Epyrifenacil spray liquid and icafolin-methyl spray liquid.” Mixtures of the epyrifenacil spray liquid and the icafolin-methyl spray liquid comprise water, DMF, and Tween20, none of which are ingredients required by the composition of instant claim 1. 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).
Conclusion
No claims are allowable.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/K.E.O./Examiner, Art Unit 1619
/NICOLE P BABSON/Primary Examiner, Art Unit 1619