Prosecution Insights
Last updated: October 02, 2026
Application No. 18/702,511

HERBICIDAL IMIDAZOLE COMPOUNDS

Final Rejection §103§DP
Filed
Apr 18, 2024
Priority
Oct 18, 2021 — GB 2114863.0 +1 more
Examiner
HIRT, ERIN E
Art Unit
1616
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Syngenta AG
OA Round
2 (Final)
40%
Grant Probability
Moderate
3-4
OA Rounds
11m
Est. Remaining
63%
With Interview

Examiner Intelligence

Grants 40% of resolved cases
40%
Career Allowance Rate
296 granted / 734 resolved
-19.7% vs TC avg
Strong +23% interview lift
Without
With
+23.0%
Interview Lift
resolved cases with interview
Typical timeline
3y 5m
Avg Prosecution
49 currently pending
Career history
795
Total Applications
across all art units

Statute-Specific Performance

§101
1.8%
-38.2% vs TC avg
§103
47.5%
+7.5% vs TC avg
§102
7.4%
-32.6% vs TC avg
§112
23.0%
-17.0% vs TC avg
Black line = Tech Center average estimate • Based on career data from 734 resolved cases

Office Action

§103 §DP
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 . 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) 1-3, 5-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hagiwara et al. (WO1995033730) and further in view of Subbaiah et al. (J. Med. Chem., 2021, 64, 14046-14128 (available 09/30/21) https://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.1c01215?ref=article_openPDF). Determination of the scope and content of the prior art (MPEP 2141.01) Regarding claims 1-2, 5-10, Hagiwara teaches structurally similar/bioisosteric herbicidal compounds, specifically compound 180, PNG media_image1.png 230 279 media_image1.png Greyscale , which is similar to the compounds of applicant’s formula (I) and (Ia) wherein applicant’s Q is 4-chlorophenyl (wherein applicant’s n is 1 and R4 is chloro/4-chloro), applicant’s R1 is in the 4 position and is ethyl/C2-alkyl, applicant’s R3 is Br, and applicant’s R2 is CF3 which read on claims 1-2, and 5-10 (see entire document, compound 180). Regarding claim 3, Hagiwara teaches wherein one of their Y and Z is a C1-C6 haloalkyl group and the other is selected from hydrogen, halogens, etc. (Abstract; claims; Y, Z has one represents a 6 haloalkyl group, the other is a hydrogen atom, halogen atom, C1-6 alkyl group), which reads on wherein the instant R3 is H. ` Regarding claims 11-13, Hagiwara teaches wherein their structurally similar herbicide compounds can be formulated as a composition with an agriculturally acceptable formulation adjuvant, and can further comprise at least one additional pesticide, specifically a herbicide (see entire document; abstract; compound 180; Paragraph beginning: The herbicide of the present invention contains one or more of the compounds… through paragraph ending with: … Vegetable oils and oil concentrates can also be added to these combinations.). Regarding claims 14, Hagiwara teaches methods of controlling weeds comprising applying effective amounts of their compounds and compositions comprising their structurally similar compounds in effective amounts (see entire document; compound 180; abstract; Paragraph beginning: The compound of the present invention shows high efficacy against various field weeds such as…by any of soil treatment and foliage treatment under upland…; Paragraph beginning: The compound of the present invention has excellent herbicidal activity against weeds such as paddy field weeds such as Nobie, Tamagayari, Omodaka and Firefly…; Paragraph beginning: The herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient. When the compound of the present invention is actually applied…; Paragraph beginning: The concentration of the active ingredient in the herbicide of the present invention…; all examples including Test examples; claims; industrial applicability section; paragraph beginning: The purpose of the present invention is to provide a herbicide that can be synthesized industrially advantageously, is effective at a lower dose, has high safety, and has high crop selectivity…). Ascertainment of the difference between prior art and the claims (MPEP 2141.02) Regarding claims 1-3, 5-15, Hagiwara does not teach wherein their phenyl ring can be the claimed pyrimidine ring. However, this deficiency in Hagiwara is addressed by Subbaiah. Subbaiah teaches that pyrimidine rings are bioisosteres of the phenyl ring of Hagiwara (see Table 2, 4a and 4H; and Table 4, 4a and 4q). 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 by replacing the 4-ethyl phenyl ring of Hagiwara for the pyrimidine ring, specifically a 4-ethylpyridimidine ring, of Subbaiah because pyrimidine rings are known bioisosteric replacements for the phenyl group of Hagiwara and would be expected to form compounds also exhibiting herbicidal activity. One of ordinary skill in the art would want to make this substitution of the ethyl pyrimidine ring for the ethyl substituted phenyl group of Hagiwara in order to form the claimed herbicidal compounds in effort to form additional compounds, compositions and methods having herbicidal activity. 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. Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13. The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer. Claims 1-14, 16-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-14 of copending Application No. 18878521 (‘521) in view of Subbaiah (as cited above). ‘521 teaches bioisosteric herbicidal compounds and compositions comprising these compounds which comprise the same additional herbicides, and formulation adjuvants as the instantly claimed compositions and the same methods of controlling weeds with the compounds/compositions as are instantly claimed and ‘521 only differs in that their claimed Q ring is a 5-membered heteroaryl in ‘521 instead of the instantly claimed phenyl or C-linked 6-membered heteroaryl, and further with respect to the new claims ‘521 teaches wherein their pyrimidine ring contains the claimed chloro substitution in the same position as instantly claimed and teach wherein their Q rings which are bioisosteric to the claimed Q rings can be substituted with the same substituents instantly claimed, e.g. methyl, trifluoromethyl, halogen, etc. However, it would have been obvious to form the claimed compounds when looking to ‘521 because Subbaiah teaches that the instantly claimed Q groups, e.g. phenyl, etc. are bioisosteres of the claimed 5-membered Q groups in ‘521 because they are bioisosteres of phenyl and as such are bioisosteres of each other (See Tables 2 and 4). Thus, one of ordinary skill in the art would conclude that the claimed compounds, compositions, and methods are obvious variants of the compounds, compositions, and methods of copending Application No. 18878521 (‘521) in view of Subbaiah and would be obvious to make in effort to form new herbicidal compounds, compositions, and methods. This is a provisional nonstatutory double patenting rejection. Claims 1-14, 16-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-15 of copending Application No. 19117705 (‘705) in view of Subbaiah (as cited above). ‘705 teaches bioisosteric herbicidal compounds and compositions comprising these compounds which comprise the same additional herbicides, and formulation adjuvants as the instantly claimed compositions and the same methods of controlling weeds with the compounds/compositions as are instantly claimed and ‘705 only differs in that their claimed U ring is a 5-membered heteroaryl in ‘521 instead of the instantly claimed pyrimidine/4-substituted pyrimidine. However, it would have been obvious to form the claimed compounds including the claimed compounds with the halogen substituted 4-pyrimidine ring in place of the 5-membered heteroaryl group of ‘521 because Subbaiah teaches that the instantly claimed pyrimidine are bioisosteres of the claimed 5-membered Q groups in ‘521 because they are both bioisosteres of phenyl and as such are bioisosteres of each other (See Tables 2 and 4) and ‘521 teaches substitution with halogens on their 5-membered heteroaryl rings. Thus, one of ordinary skill in the art would conclude that the claimed herbicidal compounds, compositions, and methods are obvious variants of the herbicidal compounds, compositions, and methods of copending Application No. 19117705 (‘705) in view of Subbaiah and would be obvious to make in effort to form new herbicidal compounds, compositions, and methods. This is a provisional nonstatutory double patenting rejection. Response to Arguments/Remarks Applicant’s amendments to the claims have rendered moot the previous claim objections and 112, and 101 rejections which are hereby withdrawn. Applicant’s arguments with respect to the 103 rejection have been fully considered but are not persuasive at this time. Applicants argue that Hagiwara fails to disclose any activity for compound 180. The examiner respectfully points out that the instant rejection is an obviousness rejection and not an anticipatory rejection and further that the prior art is art for all it teaches. The entirety of Hagiwara teaches herbicidal activity for their compounds which include structurally similar, specifically known bioisosteres of the instantly claimed pyrimidinyl ring containing compounds instantly claimed. Hagiwara expressly discloses compound 180 as an example of a compound within the bounds of their invention and they specifically teach that their compounds within their disclosure are effective as herbicides/exhibit herbicidal activity. Thus, whether or not they specifically tested compound 180 as an herbicide in their examples it is expressly made and is broadly taught by Hagiwara to exhibit herbicidal activity as that is the activity Hagiwara discloses their compounds to have. Thus, the examiner’s assertions as to the activity of the compound are not in fact unsupported as is asserted by applicants. Applicants then assert that the examiner wrongly relies of bioisosterism. The prior art teaches structurally very similar compounds which only differ in the presence of a phenyl ring in place of the instantly claimed pyrimidine ring. Pyrimidine rings and phenyl rings are well known/classical bioisosteres of one another as is taught by Subbiah and as is further evidenced by Ritchie pyrimidines are known bioisosteres for phenyl (See Ritchie entire document, abstract; etc.). One of ordinary skill in the art knowing that bioisosterism is a common replacement method used in the art for forming additional compounds which typically exhibit similar biological activity as the parent bioisosteres would obviously be prompted to make bioisosteric replacements of for instance the phenyl ring of Hagiwara with known classical bioisosteres of the phenyl moiety, e.g. the claimed pyrimidine in order to form additional compounds which would be expected to also exhibit herbicidal activity which is exactly what applicant’s observe. Thus, applicant’s arguments are not persuasive at this time and the examiner’s grounds of rejection are not using impermissible hindsight because the use of bioisosterism in forming agrochemicals is well known in the art as is evidenced by Koyanagi (see entire document), and because it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight 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). In this case, the prior art teaches compositions which only differ in the presence of a phenyl ring in place of the claimed pyrimidine and these substitutions of known classical bioisosteres is something that is commonly/routinely done by one of ordinary skill in the art in effort to form additional compounds exhibiting the same/similar biological activity and as such the examiner did not use impermissible hindsight. The examiner wonders if applicants would have an comparison data comparing their compounds with the pyrimidine ring vs the closest prior art compound(s), e.g. 180 of Hagiwara? Applicants then argue the double patenting rejections and they argue that these rejections are overcome for the same reasons discussed above. The examiner disagrees for the same reasons which are discussed above at this time. Conclusion No claims are currently allowed. Applicant's amendment necessitated the revised/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 Erin E Hirt whose telephone number is (571)270-1077. The examiner can normally be reached 10:30-7:30 ET M-F. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sue X Liu can be reached at 571-272-5539. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /ERIN E HIRT/Primary Examiner, Art Unit 1616
Read full office action

Prosecution Timeline

Apr 18, 2024
Application Filed
Feb 12, 2026
Non-Final Rejection mailed — §103, §DP
Jun 12, 2026
Response Filed
Aug 27, 2026
Final Rejection mailed — §103, §DP (current)

Precedent Cases

Applications granted by this same examiner with similar technology

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METHOD FOR CONTROLLING HERBICIDE-RESISTANT WEEDS
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PHYTOTOXIC MICRONUTRIENT COMBINATIONS FOR SELECTIVE CONTROL OF INVASIVE PLANT SPECIES
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Patent 12714107
DIOXAZOLINES AND THEIR USE AS HERBICIDES
3y 11m to grant Granted Aug 25, 2026
Patent 12672653
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6y 6m to grant Granted Jul 07, 2026
Patent 12660820
HETEROCYCLIC COMPOUND AND HARMFUL ARTHROPOD-CONTROLLING COMPOSITION INCLUDING SAME
3y 2m to grant Granted Jun 23, 2026
Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

3-4
Expected OA Rounds
40%
Grant Probability
63%
With Interview (+23.0%)
3y 5m (~11m remaining)
Median Time to Grant
Moderate
PTA Risk
Based on 734 resolved cases by this examiner. Grant probability derived from career allowance rate.

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