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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 03/25/2026 has been entered.
Applicants' arguments, filed 03/25/2026, have been fully considered. Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated or newly applied. They constitute the complete set presently being applied to the instant application.
Claim Status
Claims 1-13 and 15-21 are pending.
Claims 10-13, 15, 16, 19, and 20, are withdrawn.
Claim Objections
Claim 17 is objected to because of the following informalities: the text in the table of claim 17 is blurry, rendering the text difficult to read. The examiner requests a clearer version of the text. Appropriate correction is required.
Claim 21 is objected to because of the following informalities: the structure of the compound of claim 21 appears blurry, rendering the compound difficult to read. The examiner requests a clearer version of the structure of the compound. Appropriate correction is required.
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 1-9, 17, and 18, stand rejected under 35 U.S.C. 103 as being unpatentable over Stevenson et al (US 20180206497 A1, hereinafter Stevenson), in view of Serban et al (US 4427437 A, hereinafter Serban).
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Stevenson discloses a compound of Formula 1, including all stereoisomers, N-oxides, and salts thereof.
A is C2-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C4-C8 cycloalkoxyalkyl, C2-C6 cyanoalkyl, C3-C7 cyanoalkoxyalkyl, C1-C6 nitroalkyl, C2-C6 alkylthioalkyl, C2-C6 haloalkylthioalkyl, C3-C8 cycloalkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-C6 haloalkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C2-C6 haloalkylsulfonylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkylcarbonylalkyl, C2-C6 haloalkylcarbonylalkyl, C2-C6 alkoxycarbonylalkyl, C2-C6 haloalkoxycarbonylalkyl or C2-C6 alkoxyalkylcarbonyl; or G; or C1-C4 alkyl substituted with Q (¶ 0004). R1 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2 -C6 alkynyl, C1 -C4 alkoxy or S(O)nR4 (¶ 0005). R1 halogens include chlorine (¶ 162). R2 is halogen, cyano, nitro, CHO, C(=O)NH2 , C(=S)NH2 , SO2NH2 , C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C2-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, C(=O)N(R5a) (R56b), C(=NOR6)H, C(NR7)H or S(O)nR4 (¶ 0006). R3 is H or F (¶ 6). R4 is C1-C6 alkyl or C1-C6 haloalkyl (¶ 6). n is 0, 1, or 2 (¶ 6). The compound can be used for as herbicides (title, abs). Table A, compound 5 comprises: A = CH2CH2CH2CF3 (i.e., 4,4,4-trifluorobut-1-yl), R1 = Cl, R2 = CN, R3 = H (Table A).
Stevenson does not teach wherein the atom attached to A is a sulfur group.
Serban teaches 2-phenoxy derivatives of formula I:
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wherein R2, R3, R4, R5, or R6 are independently chosen from hydrogen, sulfo, YR1, wherein Y is oxygen or sulfur and R1 is selected from hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted alkoxysulfonyl, etc. (abs). X is oxygen or sulfur (abs). The compound can be used as an herbicide (title, abs).
Based on the teaching of Stevenson and Serban above, a skilled artisan would recognize that the oxygen in the ortho position of the phenyl ring of Stevenson can be substituted with sulfur, where sulfur and oxygen appear to be taught as obvious variants by Serban, as a matter of substituting equivalents known for the same purpose, where both teach 2-phenoxy derivatives as herbicidal actives. See MPEP 2144.06(II).
Further, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. See MPEP 2144.09(I). Here, oxygen and sulfur are both chalcogens used herbicidal compositions having structural similarities.
Regarding the instantly claimed A group of claim 1, it would have been obvious to select from C2-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 haloalkyl, C4-C8 haloalkenyl, C2-C6 haloalkynyl, C2-C6 haloalkoxyalkyl, etc., for A, as taught by Stevenson.
Regarding the instantly claimed R1 group of claim 1, it would have been obvious to select from a halogen, cyano, nitro, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 alkoxy, C1-C4 haloalkoxy, S(O)nR4, wherein n is 0, 1, or 2 and R4 is C1-C6 alkyl, and C2-C6 cyanoalkyl, as taught by Stevenson.
Further, where the R3 group of Stevenson is a hydrogen or fluorine (halogen), in either case, the limitations of instantly claimed R1(p) are met.
Regarding the instantly claimed R2 group of claim 1, it would have been obvious to select from halogen, C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 haloalkyl, C1-C4 alkoxy or S(O)nR4, wherein n is 0, 1, or 2, and R4 is C1-C6 alkyl, as taught by Stevenson.
Regarding claim 2, it would have been obvious to select hydrogen as the R3 group of Stevenson, as taught by Stevenson, thereby arriving at the instantly claimed compound of formula (Ia).
Regarding claim 3, it would have been obvious to select from C2-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 haloalkyl, C4-C8 haloalkenyl, C2-C6 haloalkynyl, or C2-C6 haloalkoxyalkyl, for A, as taught by Stevenson
Regarding claim 4, it would have been obvious to select from C2-C8 alkyl, C3-C8 haloalkyl, C4-C8 haloalkenyl, C2-C6 haloalkynyl, or C2-C6 haloalkoxyalkyl, for A, as taught by Stevenson
Regarding claim 5, it would have been obvious to select from a halogen or cyano for the R2 group of Stevenson (instant R1 group), as taught by Stevenson.
Regarding claim 6, it would have been obvious to select from halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 alkoxy, or C1-C4 haloalkoxy, for the R1 group of Stevenson (instant R2 group), as taught by Stevenson.
Regarding claim 7, it would have been obvious to select from methyl (C1 alkyl group), methoxy (C1 alkoxy group), and halogen for the R1 group of Stevenson (instant R2 group), as taught by Stevenson.
Regarding claim 8, it would have been obvious to select a halogen for the R1 group of Stevenson (instant R2 group), as taught by Stevenson.
Regarding claim 9, it would have been obvious to select chlorine for the R1 group of Stevenson (instant R2 group), a halogen taught to be suitable by Stevenson.
Regarding claims 17 and 18, it would have been obvious to select from within the disclosed species taught by Stevenson, such as 4,4,4-trifluorobut-1-yl as the instant A group, Cl as the instant R2 group, and CN as the instant R1 group, as disclosed by compound 5 of Stevenson. Regarding the sulfur, it would have been obvious to substitute the sulfur of Serban for the oxygen of Stevenson, for the same reasons discussed above and of record. The compound made obvious above appears to be compound A28 (3-(5-chloropyrimidin-2-yl)oxy-2-(4,4,4-trifluorobutylsulfanyl)benzonitrile), as instantly claimed.
Response to Arguments
Applicants assert the Office should not require Applicants’ to show unexpected results over the entire range of properties possessed by a chemical compound or composition, and cites MPEP 2145 for support. Applicants assert that as the Examiner acknowledges an improvement based on the comparative data, the claims should be allowed.
Respectfully, this argument is not persuasive. While the examiner agrees with Applicants’ that unexpected results over the entire range of properties possessed by a compound or composition is not required, MPEP 2145 recites that a showing of unexpected results for a single member of a claimed subgenus, or a narrow portion of a claimed range would be sufficient to rebut a prima facie case of obviousness if a skilled artisan could ascertain a trend in the exemplified data that would allow him to reasonably extend the probative value thereof. See MPEP 2145. The Examiner agrees with Applicants’ that the comparative data provided in a previous response as well as in the affidavit dated 03/25/2026, appears to show that compound A6 has increased phytotoxicity against AMARE, SETFA, ECHCG, and IPOHE, compared to the “ether comparator” compound. While the improvement is recognized, in accordance with the guidance provided by MPEP 2145, it does not appear that the results can be reasonably extended to the full scope of the instantly claimed compounds, where each of the claimed groups may have different reactivities, mechanisms of action, etc. In support, Tables B1 and B2 of the instant specification list pre- and post-emergence application of compounds A1-A121 with an application rate of 250 g/ha against AMARE, SOLNI, SETFA, LOLPE, ECHCH, and IPOHE (see instant tables B1 and B2). From the tables, the compounds have large variations in phytotoxicity against the tested plant species, some of which underperformed the “ether comparator” compound. For example, in post-emergence application, compounds A46 and A87 scored a “1,” corresponding to 0-20 % phytotoxicity against the same species tested in the comparison table of the affidavit, both overlapping in % phytotoxicity of the “ether comparator” compound. In pre-emergence application, compounds A33, A38, A42, A46, A48, A52, A56, A62, A64, A66, A74, A78, A87, and A89, had overlapping results, or in some cases, performed worse than the “ether comparator” compound. These results further highlight the difficulty in extending the probative data from the single comparative test of compound A6 and the “ether comparator” compound, with other compounds having different structure, where the phytotoxicity against AMARE, SETFA, ECHCH, and IPOHE, varied greatly even within compounds appearing to fall within the scope of the instant claims. Thus, it does not appear that the probative data from the results comparing compound A6 against the “ether comparator” compound can be reasonably extended to include the full scope of the instantly claimed compounds.
Allowable Subject Matter
The following is a statement of reasons for the indication of allowable subject matter:
The closest prior art appears to be Stevenson in view of Serban. While Stevenson teaches compounds of formula (I) (see above for structure), Stevenson does not teach S(O)2 in place of the oxygen atom. Serban, while teaching 2-phenoxy derivatives were known to comprise R2, where R2 can be YR1, and Y can be oxygen or sulfur, the reference does not appear to provide any indication that S(O)2 would have increased phytotoxicity over oxygen. Applicants’ appear to have shown that compound A6 showed an increase in phytotoxicity against AMARE, SETFA, ECHCH, and IPOHE compared to the “ether comparator” compound, which comprises substantially the same structure as compound A6, aside from the S(O)2 group in compound A6 and the oxygen in the “ether comparator” compound. Based on the teachings of the prior art, it appears to be unexpected that the substitution of S(O)2 for oxygen in the compound of Stevenson would have resulted in an increased phytotoxicity against AMARE, SETFA, ECHCH, and IPOHE compared to its ether counterpart.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JOSHUA A ATKINSON whose telephone number is (571)270-0877. The examiner can normally be reached M-F: 9:00 AM - 5:00 PM + Flex.
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/JOSHUA A ATKINSON/
Examiner, Art Unit 1612
/SAHANA S KAUP/Supervisory Primary Examiner, Art Unit 1612
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