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 .
Status of Claims and Response to Amendments
The amendments filed August 26, 2026 have been acknowledged and entered. Claims 1, 5-8 and 13-15 are pending.
Election/Restriction
The present examination is based on Applicant’s election without traverse of Group I (presently claims 1 and 5-6) in the reply filed on April 23, 2026. Applicant remarks filed August 26, 2026 did not overcome the art rejection set forth in the previous office action. Claims 7-8 and 13-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on April 23, 2026.
Withdrawn Rejections
Applicant is notified that any outstanding rejection or objection that is not expressly maintained in this Office Action has been withdrawn or rendered moot in view of Applicant’s amendments and/or
remarks.
Maintained Rejections
Claim Rejections - 35 USC § 103
Claim(s) 1 and 5-6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ahrens et al. (US 7,932,211)(hereinafter “Ahrens”).
The claims have been amended to recite chiral 3-sulfinylbenzoic acids of formula (I-S).
Ahrens teaches compounds of Formula (IIIb) which correspond to racemic mixtures of the claimed compounds. Ahrens teaches compound No. 5-9 (see first entry of Table E; pictured below for convenience) corresponds to the claimed compounds wherein X is Me; R’ is Me; and Z is CF3. The compounds of Ahrens contain the chiral sulfinyl group of the claims and therefore consist of both the claimed compound of formula (I-S) and the R enantiomer. Ahrens teaches the compounds are useful in the synthesis of compounds of formula (I) which have herbicidal activity (Schemes 1 and 2; col 6, lines 1-5, formula (III) is prepared from formula (IIIb); col 6, lines 25-30, compounds of formula (I)…have excellent herbicidal activity; Table A, compounds No. 1-9 to 1-16, 1-33 to 1-40). Ahrens teaches compounds of formula (I) exist as stereoisomers and that stereoisomers may be prepared selectively by using stereoselective reactions employing optically active starting materials and/or auxiliaries (col 3, lines 15-30). According to the synthetic methods for preparing formula (I) (see Schemes 1 and 2 as noted above, formula (III) is prepared from formula (IIIb)), the optically active starting materials referred to by Ahrens would correspond to formula (I-S) as well as the R enantiomer for the reason that these are the only optically active (chiral) starting material taught by Ahrens for synthesizing formula (I). Regarding enantiomeric excess, the selective preparation of a stereoisomer of formula (I) would require that the ee of the optically active starting material is high, including at least as high as 99% as required by claims (see instant claims 5-6).
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The difference between the prior art and the instant claims is that the instant claims recite formula (I-S) which is present in the prior art as a racemic mixture. However, the claimed stereoisomer would have been prima facie obvious to one having ordinary skill in the art before the effective filing date of the instant application because Ahrens had disclosed that stereoisomers of formula (I) could be prepared from optically active (chiral) starting materials, and these optically active starting materials would have corresponded to the presently claimed compound of formula (I-S). The only optically active starting material in the preparation of formula (I) according to Scheme 1 or 2 would have been a starting material prepared from racemic formula (IIIb). Optically active starting materials prepared from formula (IIIb) would have included (I-S) of the claims.
One would have been motivated as a matter of preparing specific stereoisomers of the herbicidal compounds of formula (I) disclosed by Ahrens.
One would have had a reasonable expectation of success because Ahrens had disclosed that stereoisomers of formula (I) could be prepared from optically active (chiral) starting materials. In the preparation of stereoisomers of formula (I) according to Schemes 1 or 2 one skilled in the art would have possessed a compound of formula (I-S) as is claimed.
Response to Arguments
Applicant’s arguments filed August 26, 2026 have been fully considered but they are not persuasive.
Applicant argues that Ahrens does not describe or suggest formula (I-S) (page 6 of remarks). Examiner respectfully disagrees for the reasons set forth in the rejection. Namely, Ahren’s teaches formula (I) can be prepared from optically active starting materials which in this case correspond to the claimed compound.
Applicant argues Ahrens is directed to 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazoles and their use as herbicides, whereas the claimed compounds are unexpectedly good for preparing herbicidally active compounds (page 6 of remarks). This argument is not found persuasive because the compounds of Ahrens are also useful for the preparation of herbicidally active compounds. One skilled in the art would have been motivated to use the claimed intermediates in the preparation of herbicidally active 4-(4-trifluoromethyl-3-thiobenzoyl)pyrazoles (formula I noted in the rejection).
The rejection is still deemed proper and thus maintained.
See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious).
Similarly, an optically active isomer is unpatentable over a prior art racemate or optical isomer of opposite rotation in the absence of unexpected or unobvious beneficial properties. In re Adamson et al. (CCPA 1960) 275 F2d 952, 125 USPQ 233.
Therefore, in the absence of a showing that the instant compounds demonstrate unexpected and unobvious results over the prior art compounds, the claims are deemed obvious over the prior art.
Conclusion
No claim is allowed.
THIS ACTION IS MADE FINAL. 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 KEVIN MARTIN whose telephone number is (571)270-0917. The examiner can normally be reached Monday - Friday 8 am - 5 pm.
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September 9, 2026
/K.S.M./Examiner, Art Unit 1624
/BRUCK KIFLE/Primary Examiner, Art Unit 1624
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