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 .
Applicant’s arguments, filed 11 February 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 Rejections and/or objections not reiterated from previous office actions are hereby withdrawn.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 Rejections - 35 USC § 103 (maintained)
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-4 and 6-12 are rejected under 35 U.S.C. 103 as being unpatentable over Köhn et al. (US 2014/0080705 A1, 03/20/2014, IDS reference) (hereinafter Köhn).
The disclosure of Köhn is discussed in detail above. Köhn further discloses wherein A is CY; R is hydrogen or (C1-C6)-alkyl; X is halogen or (C1-C6)-alkyl; Y is S(O)nR2; Z is halo-(C1-C6)-alkyl; R2 is (C1-C6)-alkyl or (C3-C6)-cycloalkyl; and n is 1 (claim 2). Halogen includes chlorine (Cl) ([0025], claim 14). The compounds are used for controlling unwanted plants or for regulating the growth of plant crops, by applying the compounds to the unwanted plants or to the area on which the plant crops grow ([0067]). The plant crops include transgenic plants ([0076]). The compounds may be formulated in combination with other pesticidally active substances including insecticides ([0102]) and/or at least one formulation auxiliary (clm 4). Köhn discloses a specific embodiment of formula 2-144:
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wherein X is Me, Y is SO-Me, and Z is CF3 (Table 2). Together these would provide a compound as claimed (i.e., instantly claimed No. I-13 in claims 1 and 2). Köhn further discloses a specific embodiment of formula 1-144:
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wherein X is Me, Y is SO-Me, and Z is CF3 (Table 1). Again, together these would provide a compound as claimed (i.e., instantly claimed No. I-3 in claim 3).
Moreover, it would have been obvious, for example, for one of ordinary skill in the art to have produced a N-(1,3,4-Oxadiazol-2-yl)aryl carboxamide wherein A is CY; R is methyl; X is Cl; Y is SO-Me, and Z is CF3. Together these substituents would provide a compound falling within the scope of claim 4.
The prior art is not anticipatory insofar as this combination of substituents must be selected from various lists of other substituents in the reference. It would have been obvious, however, to make the combination since all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results to one of ordinary skill in the art. See MPEP § 2143 (I)(A).
Furthermore, regarding the recitation of an absolute configuration, Köhn discloses that various stereoisomers occur with sulfoxides (when n=1). More specifically, the disclosure states that “all” stereoisomers and mixtures thereof are considered encompassed by the general formula (I), if not defined specifically (see paragraph [0029]). Thus, it would have been obvious to one of ordinary skill in the art to have prepared a compound having the absolute configuration as claimed instantly.
Regarding claims 1 and 6 reciting amounts of enantiomeric excess, as discussed above, Köhn discloses wherein stereoisomers occur with sulfoxides (when n=1), teaching selectively preparing stereoisomers. Accordingly, it would have taken no more than the relative skill of one of ordinary skill in the art to have arrived at the claimed enantiomeric excess through routine experimentation based on the level of selectivity desired in an enantiomer. See MPEP § 2144.05(II)(A). Moreover, compounds which are position isomers are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar qualities, i.e., stereoisomer obvious over prior art mixture of stereoisomer. See MPEP 2144.09 (II). Finally, regarding stereoisomers, the requirements for patentability in the case of stereoisomers is the subject matter of MPEP 2143 IB, example 8, which describes Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007), where the Federal Circuit found that claims to isolated stereoisomers is generally obvious, even without an explicit motivation. Thus, it would have been obvious to have done so, even without the clear suggestion of the prior art to prepare all possible stereoisomers.
Regarding claims 10-12, it is noted that the claims are directed to a product, therefore the “for” statements are interpreted as intended use. Where the same active agent is present in the prior art as instantly claimed, the intended use is met.
Response to Arguments
Applicant mainly asserts on pp. 5-6 of the Remarks of 11 February 2026 that the chiral compounds of formula (I) differ from the racemic compounds disclosed in Köhn 2014 by their absolute configuration. The examples in the present application show that the enantiomers of formula (I), which are (S)-configured at the alkyl sulfoxide group, demonstrate that the (S)-configured enantiomers exhibit a higher herbicidal activity than the corresponding racemic compounds disclosed in Köhn 2014. Applicant further asserts Tables 25 and 26 as demonstrating that the (S)-configured enantiomers of formula (I) generally have a higher herbicidal activity and exhibit less damaging effects on crops when compared to the corresponding racemic compounds disclosed in Köhn 2014.
The Examiner does not find the Applicant’s argument to be persuasive. As discussed in the rejection, MPEP §§ 2144.09 and 2143 (I)(B) supports isolated stereoisomers is generally obvious, even without an explicit motivation. Thus, it would have been obvious to have done so, even without the clear suggestion of the prior art to prepare all possible stereoisomers. Moreover, in this instant case, Köhn 2014 does explicitly teach in para. [0029] the occurrence of stereoisomers with sulfoxides, and further discloses the selective preparation of isolated stereoisomers by utilizing specific optically active starting materials and/or auxiliaries. Accordingly, it would have been obvious to one of ordinary skill in the art to have selectively prepared each of the stereoisomer and arrived at the more active stereoisomer as taught by Köhn 2014. Finally, in any case, MPEP § 2144.09 (VII) also supports that “if the prior art compound does in fact possess a particular benefit, even though the benefit is not recognized in the prior art, applicant’s recognition of the benefit is not in itself sufficient to distinguish the claimed compound from the prior art.” Accordingly, Applicant’s assertion is unpersuasive.
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 1-4 and 6-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-19 of U.S. Patent No. 9,101,141 in view of Köhn et al. (US 2014/0080705 A1, 03/20/2014, IDS reference) (hereinafter Köhn). The patented claims differ from the pending claims insofar as not reciting wherein the alkyl group of R is methyl, or an absolute configuration. However, Köhn discloses N-(1,3,4-oxodiazol-2-yl)aryl carboxamides having alkyl radicals as R, specifically wherein R is methyl (Table 2). Köhn further discloses that due to the nature and the bonding of sulfoxides, stereoisomers occur and can be separately obtained ([0029]). Accordingly, it would have been obvious to one of ordinary skill in the art to have arrived at the claimed absolute configuration of claimed compound wherein R is methyl, since such R group is a known and effective substituent suitable for the same backbone as taught by Köhn. Moreover, it would have been obvious to one of ordinary skill in the art to have arrived at the instantly claimed absolute configuration since it is a known selective stereoisomer due to the existence of a sulfoxide bond as taught by Köhn.
Claims 1-4 and 6-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of U.S. Patent No. 10,111,435 in view of Köhn et al. (US 2014/0080705 A1, 03/20/2014, IDS reference) (hereinafter Köhn). The patented claims differ from the pending claims insofar as not reciting an absolute configuration. However, Köhn discloses N-(1,3,4-oxodiazol-2-yl)aryl carboxamides (title). Köhn further discloses that due to the nature and the bonding of sulfoxides, stereoisomers occur and can be separately obtained ([0029]). Accordingly, it would have been obvious to one of ordinary skill in the art to have arrived at the instantly claimed absolute configuration since it is a known selective stereoisomer due to the existence of a sulfoxide bond as taught by Köhn.
Claims 1-4 and 6-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of U.S. Patent No. 10,433,553 in view of Köhn et al. (US 2014/0080705 A1, 03/20/2014, IDS reference) (hereinafter Köhn). The patented claims differ from the pending claims insofar as not reciting an absolute configuration. However, Köhn discloses N-(1,3,4-oxodiazol-2-yl)aryl carboxamides (title). Köhn further discloses that due to the nature and the bonding of sulfoxides, stereoisomers occur and can be separately obtained ([0029]). Accordingly, it would have been obvious to one of ordinary skill in the art to have arrived at the instantly claimed absolute configuration since it is a known selective stereoisomer due to the existence of a sulfoxide bond as taught by Köhn.
Claims 1-4 and 6-12 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3 and 5-15 of copending Application No. 18/054,089 in view of Köhn et al. (US 2014/0080705 A1, 03/20/2014, IDS reference) (hereinafter Köhn). The copending claims differ from the pending claims insofar as not reciting an absolute configuration. However, Köhn discloses N-(1,3,4-oxodiazol-2-yl)aryl carboxamides (title). Köhn further discloses that due to the nature and the bonding of sulfoxides, stereoisomers occur and can be separately obtained ([0029]). Accordingly, it would have been obvious to one of ordinary skill in the art to have arrived at the instantly claimed absolute configuration since it is a known selective stereoisomer due to the existence of a sulfoxide bond as taught by Köhn.
This is a provisional nonstatutory double patenting rejection.
Response to Arguments
Applicant will address the double patenting rejections, to the extent necessary, once they are the only rejections remaining.
Since this has not happened yet, the rejections are maintained.
Citation of Pertinent Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Poree et al. (US 2017/0015638 A1, 01/19/2017) is directed to use of N-(1,3,4-oxadiazol-2-yl)arylcarboxamides for controlling unwanted plants in areas of transgenic crop plants, and embodiment 2-360, wherein X is Cl; Y is S(O)Me; and Z is CF3.
Köhn et al. (US 2018/0077935 A1, 03/22/2018) is directed to salts of N-(1,3,4-oxadiazol-2-yl)benzamide for controlling unwanted plants.
Köhn et al. (US 2018/0179171 A1, 06/28/2018) is directed to N-(1,3,4-oxadiazol-2-yl)arylcarboxamide derivatives for controlling unwanted plants in one or more crops or useful plants.
Perez Catalan et al. (WO 2017/025396 A1, 02/16/2017) is directed to herbicidal compositions comprising 2-chloro-N-(5-methyl-1 ,3,4-oxadiazol-2-yl)-3- (methylsulfinyl)-4-(trifluoronnethyl)benzannide (p.3, A6), and use thereof to control weed plants in crops of useful plants.
Ahrens et al. (US 2020/0055829 A1, 02/20/2020, IDS ref.) is directed to a benzoylamide (claim 5), useful for controlling one or more unwanted plants.
Koehn et al. (US 2016/0235067 A1, 08/18/2016, IDS ref.) is directed to herbicide-safener compositions comprising N-(1,3,4-oxadiazol-2-yl)arylcarboxamides (e.g. Ex. A1-14) useful for controlling harmful plants in crops of useful plants.
Conclusion
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 LUCY TIEN whose telephone number is (571)272-8267. The examiner can normally be reached Monday - Thursday 8:30 AM - 6:30 PM EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, SAHANA KAUP can be reached at (571) 272-6897. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/LUCY M TIEN/Examiner, Art Unit 1612
/SAHANA S KAUP/Supervisory Primary Examiner, Art Unit 1612
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