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
Claims 1, 3-5, 7-9, and 11-19 are pending in this office action. Claims 11-19 are new. Claims 2, 6, and 10 are cancelled. All pending claims are under examination in this application.
Priority
The current application filed on January 20, 2024 is a 371 of PCT/CN2022/109677 filed August 2, 2022. The current application claims foreign priority to CN202111677946.8 filed December 31, 2021, CN202111034823.2 filed September 4, 2021, and CN202110946153.5 filed August 18, 2021, respectively.
Information Disclosure Statement
Receipt of the Information Disclosure Statement filed on January 16, 2026 is acknowledged. Both signed documents are attached to this office action.
Claim Objections
Claims 1, 3-5, 7-9, and 11-19 objected to because of the following informalities:
Claim 1 needs the text “and” amended prior to the end of the last clause.
Dependent claims 3-5, 7-9, and 11-19 fail to cure the defect with claim 1.
Appropriate correction is required.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 3-4, 9, and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chang (US4,405,357A).
Chang is regarded as being the prior art closest to the subject matter of the present application as it teaches herbicidal 3-isoxazolidinones and hydroxamic acids (see title). Furthermore, Chang discloses novel 3-isoxazolidinone compounds and novel hydroxamic acid intermediates from which are prepared exhibiting herbicidal activity to grassy and broad-leaf plant species while leaving legumes, especially soybeans, unaffected. The preparation and herbicidal activity of the compounds is exemplified (see abstract).
Regarding instant claim 1, Chang teaches a herbicidal 3-isoxazolidinone composition. The necessary citations within Chang that correspond to instant claim 1 are compiled within Table I.
Table I
Instant Claim 1
Chang Citations
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I
wherein both Q1 and Q2 represent O; both R1 and R2 represent methyl.
Chang disclose the following claim:
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(see claim 15). This structure presented by Chang meets the instant claim 1 limitations.
[Henceforth within the office action, all elements of instant claim 1 are taught by Chang].
Regarding instant claims 3 and 11, Chang teaches wherein the composition is synthesized under the appropriate parameters (see Example 30 step C; column 19, lines 9-23).
Regarding instant claims 4 and 9, Chang teaches wherein the herbicidal composition contains (i) a herbicidally effective amount of at least one of the 3-isoxazolidinone compounds according to instant claim 1. Chang discloses the herbicidal biological evaluation of the 3-isoxazolidinone derivatives (see columns 24-42; also see abstract). This would apply directly to instant method claim 9.
Claims 1, 4-5, 8, 12, 14, 16, and 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ensminger et al. (WO92/10095A1).
Ensminger et al. teach antidoting herbicidal 3-isoxazolidinone compounds (see title). In addition, Ensminger et al. disclose compositions comprising herbicidally effective compounds corresponding to formula (I) in which R1 and R2 are independently methyl or ethyl, X is H, methyl, chlorine, bromine, fluorine; Y is chlorine, bromine, fluorine; and n is 0, 1 or 2 and a non-phytotoxic antidotally effective amount of an antidote therefor selected from the group of amides of haloalkanoic acids, including oxazolidines and thiazolidines, aromatic oxime derivatives, thiazole carboxylic acids and derivatives, substituted phenylpyrimidines, 2-(dichloroacetyl)-2-methyl-I,3-dioxolane and 2-(dichloromethyl)-2-thiazoline.
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Regarding instant claim 5, Ensminger et al. teach wherein the herbicidal composition according to instant claim 4, characterized in that further comprising (ii) a herbicidally effective amount of one or more additional herbicides and/or safeners. Ensminger et al. disclose all the instant claim 1 limitations:
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Additionally, Ensminger et al. disclose all the instant claim 4 limitations emphasizing the herbicidal composition (see Examples 1-4 and formulations; also see abstract). Ensminger et al. teaches wherein the herbicidal composition according to instant claim 4, characterized in that further comprising (ii) a herbicidally effective amount of one or more additional herbicides and/or safeners [(antidotes = safener; see PTO-892 NPL U); see Examples 1-4 and formulations; also see page 12, paragraphs 1-3].
Regarding instant claim 6, Ensminger et al. teach wherein the correct additional herbicide is selected [(butachlor and acetochlor); see page 12, paragraphs 1-3].
Regarding instant claims 8 and 12, Ensminger et al. teach wherein the herbicidal composition according to instant claim 4, characterized in that further comprising (iii) an agrochemically acceptable formulation auxiliary. Ensminger et al. disclose the use of an antidote or safener which is an agrochemically acceptable formulation auxiliary; see Examples 1-4 and formulations].
Regarding instant claims 14, 16, and 18, Ensminger et al. teach a method for controlling an undesirable plant, comprising applying the herbicidal composition according to claim 4 in a herbicidally effective amount on a plant or in its area or to soil or water to control the emergence or growth of an undesirable plant. Ensminger et al. disclose that this invention comprises novel herbicidal compositions which provide excellent protection for a variety of crops from adverse herbicidal injury which composition comprises an herbicidally effective amount of a 3-isoxazolidinone and a substantially non-phytotoxic, antidotally-effective amount of an herbicide antidote, selected from the group consisting of amides of haloalkonoic acids, aromatic oxime derivatives, thiazole carboxylic acids and derivatives and substituted phenyl pyrimidines (see page 3, paragraph 1).
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 non-obviousness.
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 and 4-5, 7, 9, and 13-19 are rejected under 35 U.S.C. 103 as being unpatentable over Chang in view of Ensminger et al. and Williams et al. (US5,256,626A) and Krause et al. (WO2019/076744A1).
[The Examiner is going to introduce the new references and then combine them where appropriate to reject the instant claims.]
1. Williams et al.
Williams et al. teach herbicidal compositions safened by 5-heterocyclic-substituted oxazolidine dihaloacetamides compounds (see title). Additionally, the Williams et al. disclosure relates to a new family of haloalkyl oxazolidinyl derivatives as antidotal compounds to reduce injury to crop plants by a variety of herbicides. The antidotal compounds are characterized particularly by having heterocyclyl or spiroheterocyclyl radicals attached to the 5-position of haloalkyl oxazolidine compounds and are especially useful as in-can antidotes against injury by acetanilide and thiocarbamate herbicides to com, sorghum, soybeans, wheat, rice and other crops (see abstract).
2. Krause et al.
Krause et al. teach aqueous [2-(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone-based suspension concentrates (see title). In addition, Krause et al. disclose that the present invention relates to aqueous 2-((2,4-dichlorophenyl)methyl)-4,4'-dimethyl-3-isoxazolidinone-based suspension concentrates, the production thereof and to the mixtures thereof with suspension concentrates and the use thereof as agrochemical formulations with low volatility and damage to adjacent cultures (see abstract).
The teachings of Chang and Ensminger et al. are disclosed above within the 35 U.S.C. § 102 Section above.
Combination of Chang, Ensminger et al., Williams et al., and Krause et al.
Regarding instant claim 7, Chang, Ensminger et al., Williams et al., and Krause et al. teach wherein the herbicidal composition according to instant claim 6, characterized in that the active ingredient (i) to the additional herbicide in (ii) in the herbicidal composition is in a correct weight ratio. Williams et al. disclose additional herbicides that can be used with the present invention (see columns 4-6 within Williams et al.). A skilled artisan (POSITA; person of ordinary skill in the art) using the Chang, Ensminger et al., and Williams et al. disclosures would afford a herbicidal composition according to instant claim 6, characterized in that the active ingredient (i) to the additional herbicide in (ii) in the herbicidal composition is in a correct weight ratio of at least 1:1000 ~ 1000:1 (broad range).
Regarding instant claims 13 and 15, Chang, Ensminger et al., Williams et al., and Krause et al. teach wherein the undesirable plant includes herbicide-resistant or -tolerant weed species. Williams et al. disclose that although [there is] no hard and fast rule, it is desirable from a commercial viewpoint that 80-85% or more of the weeds be destroyed, although commercially significant suppression of weed growth can occur at much lower levels, particularly with some very noxious, herbicide-resistant plants (see column 3, lines 50-55 within Williams et al.). Furthermore, Williams et al. disclose a discussion on herbicide resistance and the overall selectivity factor (see column 7, lines 11-20). Therefore, Williams et al. is aware of herbicide resistance and the selectivity of herbicides. A skilled artisan (POSITA) would be able to summarize and collect the necessary data on herbicide resistance under routine experimental conditions.
Regarding instant claims 17 and 19, Chang, Ensminger et al., Williams et al., and Krause et al. teach wherein the useful crop includes a transgenic crop or a crop treated by genome editing techniques, and the weed includes herbicide-resistant or -tolerant weed species. Krause et al. disclose that the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses (see page 25, paragraph 6 within Krause et al.). Furthermore, Krause et al. disclose that in the application of the herbicidal agents in transgenic crops, in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled. Application rates that can be used for the application, preferably good compatibility with the other herbicidal active ingredients to which the transgenic culture is resistant, and influencing the growth and yield of transgenic crops. The present invention thus also provides a method for controlling undesired plant growth, preferably in crops…(see page 25, paragraph 8 within Krause et al.). Moreover, a skilled artisan (POSITA) would use the teachings of Williams et al. within instant claims 13 and 15 to determine and evaluate the herbicide resistance of weed species.
Analogous Art
The combination of the Chang, Ensminger et al., and Williams et al. references are relevant for the rejection of instant claims 1 and 4-5, 7, 9, and 13-19 due to their direct application to the present invention.
Obviousness
It would have been prima face obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the herbicidal 3-isoxazolidinone disclosed by Chang, using the teachings of Ensminger et al., Williams et al., and Krause et al. to incorporate the necessary claim limitations.
The motivation to combine the Chang, Ensminger et al., Williams et al., and Krause et al. references relies on the common theme to develop an isoxazolidinone herbicide. Both Chang and Ensminger et al. support the development of a herbicidal 3-isoxazolidinone. Williams et al. is another reference example that uses multiple herbicides within the agricultural arts. Finally, Krause et al. addresses the use of transgenic crops. All four references are analogous art.
Starting with Chang, the skilled person only had to try the necessary claimed limitations disclosed by Ensminger et al., Williams et al., and Krause et al. The combination of Chang, Ensminger et al., Williams et al., and Krause et al. would allow one to arrive at the present application without employing inventive skill. This combination of the herbicidal 3-isoxazolidinone taught by Chang along with the necessary use of the claimed limitations taught by Ensminger et al., Williams et al., and Krause et al. would allow a research and development scientist (POSITA) to develop the invention taught in the instant application. It would have only required routine experimentation to modify the herbicidal 3-isoxazolidinone disclosed by Chang with the use of the necessary claimed limitations disclosed taught by Ensminger et al., Williams et al., and Krause et al. This combined modification would have led to an enhanced herbicidal 3-isoxazolidinone, and thus beneficial for consumers.
Response to Arguments
Applicant's arguments filed March 12, 2026 have been fully considered but they are not persuasive.
The instant claim amendments were sufficient to address the claim objections, 35 U.S.C. §112(b) rejections, and 35 U.S.C. §101 rejection. Therefore, they are all withdrawn from the non-final office action dated December 17, 2025.
The amendments did necessitate a new ground of rejection with the addition of the Krause et al. citation.
Applicant Argument: The Applicant argues that within the 35 U.S.C. §102 rejections neither Chang nor Ensminger et al. disclose the compound of instant claim 1 and therefore the rejection should be withdrawn.
Examiner’s Rebuttal: The Examiner respectfully disagrees. Yes, the two references do not disclose a specific example of the herbicide of instant claim 1. However, the generic claim structures within the two references inherently anticipates the herbicide. "A claim is anticipated only if each and every element as set forth in the claim is found, either expressly or inherently described, in a single prior art reference." Verdegaal Bros. v. Union Oil Co. of California, 814 F.2d 628, 631, 2 USPQ2d 1051, 1053 (Fed. Cir. 1987). "When a claim covers several structures or compositions, either generically or as alternatives, the claim is deemed anticipated if any of the structures or compositions within the scope of the claim is known in the prior art." Brown v. 3M, 265 F.3d 1349, 1351, 60 USPQ2d 1375, 1376 (Fed. Cir. 2001) (claim to a system for setting a computer clock to an offset time to address the Year 2000 (Y2K) problem, applicable to records with year date data in "at least one of two-digit, three-digit, or four-digit" representations, was held anticipated by a system that offsets year dates in only two-digit formats). See also MPEP § 2131.02. "The identical invention must be shown in as complete detail as is contained in the ... claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).
Furthermore, Chang does not teach away from modifying position 2 of the phenyl ring with a bromine. Once a synthetic organic chemist establishes that the 2,4-dichloro variation of Example 22 is classified as a lead compound, the two and four positions then become an area for structure-activity relationships. To discard the bromo variation would be a mistake [combination of the two bromo four chloro analogue would be pusued by a skilled artisan]. Moreover, the generic claim structure of both Chang and Ensminger et al. disclose the herbicide within instant claim 1.
Therefore, the 35 U.S.C. §102 rejections are maintained.
Applicant Argument: The Applicant argues that the herbicide of instant claim 1 and mixtures thereof provides unexpected results.
Examiner’s Rebuttal: The Examiner respectfully disagrees. Evidence of unexpected results must be weighed against evidence supporting prima facie obviousness in making a final determination of the obviousness of the claimed invention. In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (Claims directed to a method of effecting analgesia without producing physical dependence by administering the levo isomer of a compound having a certain chemical structure were rejected as obvious over the prior art. Evidence that the compound was unexpectedly nonaddictive was sufficient to overcome the obviousness rejection. Although the compound also had the expected result of potent analgesia, there was evidence of record showing that the goal of research in this area was to produce an analgesic compound which was nonaddictive, enhancing the evidentiary value of the showing of nonaddictiveness as an indicium of nonobviousness.). [see M.P.E.P. 716.02(c)]. In this instance, the prior art of record is stronger than the unexpected results. The prima facie case for obviousness presented within the 35 U.S.C. §103 section of this office action affords a “direct pathway” of research for a skilled artisan (POSITA) to develop and obtain similar results as observed by the inventors.
On a scale of patentability, the prima facie case of obviousness outweighs the unexpected results which have been noted by the Examiner.
Additionally, instant claim 5 has been rejected under 35 U.S.C. §102 and unexpected results do not contribute to overturning this rejection. They are only applied to 35 U.S.C. §103 rejections.
[Examiner’s Note: Applicant may also argue impermissible hindsight reasoning. However, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight [or piece-meal reasoning.] But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).]
Thus, the 35 U.S.C. §102 and §103 rejections for instant claims 1, 3-5, 7-9, and 11-19 is maintained.
Conclusion
No claims are allowed.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JOHN W LIPPERT III whose telephone number is (571)270-0862. The examiner can normally be reached Monday - Thursday 9:00 AM - 5:00 PM.
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/JOHN W LIPPERT III/Examiner, Art Unit 1615
/Robert A Wax/Supervisory Patent Examiner, Art Unit 1615
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