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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 10/15/25 has been entered.
Examiner Suggestions
The examiner suggests that Claim 13 should recite “an additional herbicide” instead of “a further herbicide”. The examiner also suggests that claim 15 should recite “seeds thereof, and/or habitat thereof” instead of “its seed, and/or its habitat”.
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.
Claim(s) 1, 10, 12-13, and 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Willms et al. (US20140100108 and the megatable cited in the document and found at https://seqdata.uspto.gov/?pageRequest=docDetail&DocID=US20140100108A1 table can also be found in WO2012130798 which is PCT/WO document from which US20140100108 claims priority), and further in view of Koyanagi (Ch. 2: Bioisosterism in Agrochemicals, 1995).
Determination of the scope and content of the prior art
(MPEP 2141.01)
Regarding claims 1, 10, and 12, Willms teaches bioisosteric herbicidal compounds to those instantly claimed, specifically for instance at least compounds 6.029-6.032, etc. which only differ from the claimed compounds in that it has a CH2 group in place of the instantly claimed O atom in formula I (see entire document; e.g. abstract; [0007-0043]; [0397]; [0429], claims; [0115-154]; [0387-0388]; compounds 6.029-6.032, etc.). Specifically, with respect to claim 10, at least compounds 6.029-6.032, have all of the claimed variables which overlap those instantly claimed and specifically have as Z the claimed cyclobutyl or cyclopentyl groups which are unsubstituted as m=0, and wherein R2, R4, and R6 are all H, R3 and R5 are both halogen, R1 is hydrogen, R7 is methyl, X is a bond, Y is Z, and Z is cyclobutyl or cyclopentyl, etc. (see compounds 6.029-6.032 in megatable (also can be found in the WO2012130798 which is PCT from which US20140100108 claims priority; see entire document; e.g. abstract; [0007-0043]; [0397]; [0429], claims; [0115-154]; [0387-0388]).
Regarding claim 12, Willms teaches a composition comprising their bioisosteric compounds to those instantly claimed and at least one auxiliary that is customary for formulating crop protection compounds ([0258-0275]; [0276-0278]; Claims; abstract; [0007-0043]).
Regarding claim 13, Willms teaches wherein their composition of comprising their bioisosteric compounds to those instantly claimed can further comprise an additional herbicide ([0258-0275]; [0276-0278]; Claims).
Regarding claim 15, Willms teaches a method for controlling unwanted vegetation comprising applying/allowing an herbicidally effective amount of their bioisosteric compounds to act on/applied to the unwanted vegetation/plants and/or its habitat ([0232-0242]; [0298-0302]; [0315]; [0001]; [0258]; Claims).
Ascertainment of the difference between prior art and the claims
(MPEP 2141.02)
As discussed above Willms teaches structurally similar, specifically bioisosteric compounds to those instantly claimed but does not specifically teach the claimed compounds. However, it would have been obvious to replace the CH2 group in the 1,2-oxazole ring of Willms for the instantly claimed O atom to form the dioxazoline ring because Koyanagi teaches that CH2 and O are known classical bioisosteres of one another for use in forming agrochemical compounds (See Table 1), and Koyanagi teaches that bioisosterism is a known optimization technique useful for designing/developing agrochemicals that is known in the art to be useful as demonstrated by large number of successes in molecular optimization (See first two paragraphs, e.g. abstract and first intro paragraph).
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
It would have been obvious to one of ordinary skill in the art at the time of the instant filing to have formed the claimed compounds, compositions and methods instantly claimed when looking to Willms in view of Koyanagi because Willms already teaches that the structurally similar and biosisoteric 1,2-oxazole containing compounds exhibit herbicidal activity and it is known in the art to substitute the CH2 group of Willms in their 1,2-oxazole ring containing compounds for the instantly claimed O atom in the claimed dioxazoline ring because CH2 and O are known classical bioisosteres of one another are routinely substituted in order to form additional agrochemically active compounds having the same/similar biological activity as is taught by Koyanagi as this is a known useful technique in designing agrochemicals. Further, the courts have found, “Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious.” In rePayne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979), In re Merck & Co., Inc., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986) (claimed and prior art compounds used in a method of treating depression would have been expected to have similar activity because the structural difference between the compounds involved a known bioisosteric replacement).
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the above claims would have been obvious to one of ordinary skill in the art within the meaning of 35 USC 103(a).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Additional Prior art of relevance
WO2014048882 (for the same reasons discussed above), WO2018228985 (for the same reasons discussed above), etc. all from IDS.
Response to Arguments/Remarks
Applicant’s amendments to the claims have prompted the new/revised grounds of rejection presented herein. Applicant’s arguments with respect to the 103 rejections have been fully considered and insofar as they pertain to the revised grounds of rejection are addressed herein.
Applicants argue that there is no suggestion to arrive at the claimed compounds with any reasonable expectation that they would retain herbicidal activity. They argue that there would have been no reason to make the substitution argued by the examiner in the previous office action to have the dioxazoline ring in place of the isooxazoline ring of Willms. The examiner respectfully disagrees. It would have been obvious to substitute the corresponding CH2 group to an O atom in the structurally similar and biosisoteric 1,2-oxazole/isooxazoline ring containing compounds of Willms which exhibit herbicidal activity in order to form the claimed dioxazoline ring because CH2 and O are known classical bioisosteres of one another are routinely substituted in order to form additional agrochemically active compounds having the same/similar biological activity as is taught by Koyanagi as this is a known useful technique in designing agrochemicals. Further, the courts have found, “Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious.” In rePayne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979), In re Merck & Co., Inc., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986) (claimed and prior art compounds used in a method of treating depression would have been expected to have similar activity because the structural difference between the compounds involved a known bioisosteric replacement).
Applicants argue that bioisosterism does not permit any definitive prediction with respect to observable effects. The examiner respectfully points out that the instant rejection is an obviousness rejection and definitive success or a definitive prediction of activity is not required. The legal standard for an obviousness rejection is a reasonable expectation of success, and in the instant case based on the combined teachings of the prior art one of ordinary skill in the art would have a reasonable expectation that the substitution of a CH2 group for the second O atom in the dioxazoline which provides the difference from the biosisoteric herbicidal 1,2-oxazole (isooxazoline) containing compounds of Willms would have had a reasonable expectation of success in leading to herbicidal compounds and as such the combination of the prior art is appropriate and still renders the instant invention obviousness for the reasons discussed above and herein.
Applicants then argue that there is no indication that the isoxazoline ring of ‘108 should be replaced by the claimed dioxazoline. The examiner respectfully points out that the addition of an additional O atom in the ring of the isoxazoline would have been obvious based on the teachings of Koyanagi, especially in the absence of evidence to the contrary for the reasons discussed above and herein. Applicant’s then argue why this position on the ring. The examiner respectfully point out that any position on the ring changed from CH2 to O would be expected to lead to additional herbicidal compounds. And dioxazoline rings are known in the art to be structurally similar to isooxazoline rings and as such would be an obvious substitution for one of ordinary skill in the art to make in effort to form additional bioisosteric compounds with herbicidal activity just as applicants have done.
Applicants then argue that their compounds surprisingly demonstrate an excellent herbicidal activity in pre- and post-emergence applications at low application rates (i.e. 250 g/ha) and that these results could not have been expected. The examiner first respectfully points out that these results are not commensurate in scope with the instant claims which allow for a much broader substituent scope on the core ring structure than applicant’s have demonstrated their argued improved/excellent herbicidal activity with when compared to the isooxazoline compounds of Willms, e.g. in the declaration filed 10/15/25. Thus, applicants have not made it clear that these improved/excellent herbicidal activity vs. the compounds of Willms is present across the broad scope of compounds instantly claimed. Further, with respect to the much reduced crop damage seen in the single example in applicant’s declaration these results also have not been demonstrated to occur across the broad scope of dioxazoline containing compounds claimed when compared to the isooxazoline containing structurally similar compounds of Willms.
Applicants finally argue the case law of Mylan Pharms. Inc v. Research Corp. Techs. Because in that case it was the replacement of an NH with a CH2 and the courts found that the substitution was not obvious because it would have yielded a different conformation. The examiner has looked through this case and this case is not particularly relevant to the instant application in that in the Mylan case the Kohn 1991 reference specifically taught that R group being NH(OCH3) had a 10 fold higher activity than when R was NH2 and Kohn taught that compound without the methoxyimino group or N-containing moiety at the alpha carbon had reduced activity and as such it would not have been obvious to substituted the NH for CH2. In the instant case, the prior art already teaches their compounds have herbicidal activity. Koyanagi teaches that CH2 for O is a routine bioisosteric replacement done in agriculturally active compounds in order to form additional agrochemically active compounds and to probe the biological activity of related derivative compounds. There is nothing in Willms which expressly teaches away from substituting a CH2 group in the isooxazoline ring of Willms for an O in order to form the claimed dioxazoline ring as was the case in the Mylan Pharms. Inc v. Research Corp. Techs case cited by applicants.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the above claims would have been obvious to one of ordinary skill in the art within the meaning of 35 USC 103(a).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Declaration under 1.132
Benedict Wyrwol provided a declaration under 1.132, filed 10/15/25. The Declaration meets the formal requirements. In the most relevant part, the Declaration presents results of instantly claimed compound I.8 as compared to a structurally similar compound falling into the scope of Willms (US20140100108) which only differs because it contains an isooxazoline ring in place of the claimed dioxazoline ring. A Declaration is due full consideration and weight for all that it discloses. Declarations are reviewed for the following considerations: 1) whether the Declaration presents a nexus such as a side-by-side or single-variable comparison (In re Huang, 40 USPQ2d 1685, 1689 (Fed. Cir. 1996)), 2) whether the Declaration presents a comparison to the closest art, 3) whether the Declaration is commensurate in scope with the scope of the claims (In re Kulling, 14 USPQ2d 1056, 1058 (Fed. Cir. 1990)), 4) whether the Declaration shows a difference in kind rather than merely a difference in degree (In re Waymouth, 182 USPQ 290, 293 (C.C.P.A. 1974)), and 5) whether the prima facie case is sufficiently strong that allegedly superior results are insufficient to overcome the case for obviousness (Pfizer Inc. v. Apotex, Inc., 82 USPQ2d 1321, 1339 (Fed. Cir. 2007)).
The relevant criterion here is No. 3, whether the Declaration is commensurate in scope with the scope of the claims (In re Kulling, 14 USPQ2d 1056, 1058 (Fed. Cir. 1990)). The examiner has carefully reviewed the Declaration, including the data presented in the Declaration. The data shows that applicant’s compound I.8 had high herbicidal activity but also provided much decreased crop damage when compared to the isooxazoline containing compound which falls within the scope of Willms. However, these results which do show a marked decrease in herbicidal damage in crop plants, specifically in soybean and rice crops, is not commensurate in scope with the instant claims which claim much broader scope of dioxazoline compounds than were tested/compared in applicants experiments. Thus, it has not been made clear whether these results will also occur across the entirety of applicant’s claimed compound scope. Thus, the declaration and results from the specification do not overcome the prior art rejections presented above at this time because the results demonstrated are not commensurate in scope with the claims.
In light of the forgoing discussion and evaluation of the declaration submitted by Benedict Wyrwol on 10/15/25, the Examiner concludes that the subject matter defined by the above claims would have been obvious to one of ordinary skill in the art within the meaning of 35 USC 103(a) at this time, specifically because applicants argued unexpected results are not commensurate in scope with the broad compound scope instantly claimed.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Erin E Hirt whose telephone number is (571)270-1077. The examiner can normally be reached 10:30-7:30 ET M-F.
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/ERIN E HIRT/Primary Examiner, Art Unit 1617