CTNF 17/783,859 CTNF 77983 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia 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 response and claim amendment filed on March 12, 2026 have been fully considered. The previous claim rejection made under 35 U.S.C. 103 over O’Sullivan et al. (US 20150045213 A1) in view of Boebel et al. (US 20140011824 A1) has been modified to correct typographical error and specifically point out the elected species. A new rejection has been made under 35 U.S.C. 112(b) to address the amended claim 1. Claim Rejections - 35 USC § 112 07-30-02 AIA The following is a quotation of 35 U.S.C. 112(b): (b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention. The following is a quotation of 35 U.S.C. 112 (pre-AIA), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. 07-34-01 Claims 1, 8-11 and 15-19 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 1 recites the broad recitation of the compound according to formula (Ia), and the claim also recites wherein the compound of formula (Ia) is a compound of formula (Ic), which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. Claim 1 is also vague and indefinite as the constituents R1-R5 of the formulas (Ia) and (Ib) are not defined. The remaining claims are rejected for depending on the indefinite base claim. Claim Rejections - 35 USC § 103 07-20-aia AIA 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. 07-21-aia AIA Claims 1, 8-11 and 15-19 are r ejected under 35 U .S.C. 103 as being unpatentable over O’Sullivan et al. (U S 20150045213 A1, published on August 16, 2016, US equivalent of WO 2013143811 of IDS) (“O’Sullivan” hereunder) in view of Boebel et al. (US 20140011824 A1, published on January 9, 2014) (“Bebel” hereunder). Claim 1 is represen tative of the present invention and is directed to a method of controlling or preventing infestation of peanut plants by the phytopathogenic microorganism Cercospora, comprising applying to a crop of the peanut plants, a compound according to formula (Ia) having (S,S) stereo-configuration and optionally further comprising a compound according to formula (Ib) having (R,R) stereo-configuration: the locus thereof, or propagation material thereof, a compound according to formula (I) PNG media_image1.png 685 672 media_image1.png Greyscale wherein B and A-CO—NR5 are cis to each other on the four-membered ring, and wherein when the compound of formula (Ib) is present, the weight ratio of the compound of formula (Ia) to the compound of formula (Ib) is greater than about 1:1, and wherein the compound of formula (Ia) is a compound of formula (Ic); . PNG media_image2.png 156 340 media_image2.png Greyscale (Ic) wherein R11 and R12 are independently selected from halogen; A is pyridyl which is substituted by one or two substituents independently selected from halogen, C1-C4 alkyl, and C1-C4-haloalkyl. O’Sullivan teaches a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a compound of formula (I) is applied as active ingredient to the plants, to parts thereof or the locus thereof. The reference teaches the targeted phytopathogenic microorganisms that are controlled by the compound include the Cercospora genus; that the useful plants to be treated include leguminous plants. See [0146, 0161, 0162, 0164]. The reference teaches that formular (I) is characterized as a cis isomer. [0003]. The reference discloses compounds of the formula (I) as following: PNG media_image3.png 295 634 media_image3.png Greyscale wherein Y is O, C ═ O, or CR12R13; A is a 5- or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms, each independently selected from oxygen, nitrogen and sulphur, or a phenyl ring; the heteroaromatic ring or the phenyl being optionally substituted by one or more R6; R6 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkoxy-C 1-4 -alkyl or C1-C4-haloalkoxy-C1-C4-alkyl; R1, R2, R3, R4, R12 and R13, independently of each other, are hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl, R5 is hydrogen, methoxy or hydroxyl, B is phenyl substituted by one or more R8, R8 is, independently of each other, halogen, cyano or a group -L-R9, where each L is independently of each other a bond, —O—, —OC(O)—, —NR7-, —NR7CO—, —NR7S(O)n—, —S(O)n—, —S(O)nNR7-, —COO— or CONR7-, n is 0, 1 or 2, R7 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl and phenyl are unsubstituted or substituted with halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl, R9 is, independently of each other, C1-C6-alkyl, which is unsubstituted or substituted by one or more R10, C3-C6-cycloalkyl, which is unsubstituted or substituted by one or more R10, C6-C14-bicycloalkyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkenyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkynyl, which is unsubstituted or substituted by one or more R10, phenyl, which is unsubstituted or substituted by R10, or heteroaryl, which is unsubstituted or substituted by one or more R10, R10 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-alkenyloxy, or C3-C6-alkynyloxy, wherein B and A-CO—NR5 are cis to each other on the four-membered ring, and tautomers/isomers/enantiomers of these compounds. See reference claim 1; paragraphs [0004-0005]. As for the elected species Compound 1, O’Sullivan explicitly discloses that preferred examples of A includ e 2-trifluoromethyl-3-pyridyl (“A2”) as well as 3-trifluoromethyl-2-pyridyl(A3) with a particularly preferred embodiment containing Y = CH2, R1, R3, R4 are each hydrogen and B is a mono or di-halogen substituted phenyl comprising constituents R9a, R9b and R9c. See. [0033-0035], [0084], [0087] and [0089]; Table Y teaches compound Y.0034 when R9a and R9b are 2-Cl and 4-Cl or F, which correspond to R11 and R12. See also Y.0035 and Y.0037. Thus, the elected species is an obvious variation of formula (I) which is suggested in the teachings of the reference. See the present claims 1-8 and 16. The reference does not specifically disclose using the compound to treat Cercospora infestation on peanut plants. Bebel teaches that Cercospora fungal pathogens include Cercospora arachidicola which infects peanut foliage causes leaf spots. Given the teachings of O’Sullivan that the compounds of formula 1 are useful in protecting leguminous plants against and also useful as a fungicides against Cercospora species, one of ordinary skill in the art before the effective filing date would have been obviously motivated to look to prior art such as Bebel for the use of the compounds to control Cercospora fungal pathogens. Since Bebel teaches that Cercospora arachidicola causes leaf spots in peanut, and O’Sullivan teaches that teaches that the compounds are useful as fungicides, including Cercospora, in protecting leguminous plants, the skilled artisan would have had a reasonable expectation of successfully combining the teachings of the references and use the compounds in controlling the Cercospora fungal attack on peanut plants. See the present claim 11. The present claim 1 further requires that the weight ratio of the compound of formula (Ia) to the compound of formula (Ib) is “greater than about 1:1”; such range reads on the (S,S) and (R,R) enantiomers ratio of 1:1. O’Sullivan specifically teaches that the compounds of formula (I) can be present in the form of racemates. See [0006]. Regarding claims 15 and 17, O’Sullivan fails to specifically disclose the ratio of the enantiomers as described in the present claim. However, the reference teaches that methods of isolating or synthesizing the isomers are well known in the art: [0064] Diastereomer mixtures or racemate mixtures of compounds of formula (I), in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography. [0065] Enantiomer mixtures, such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphoric, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the diastereomers, from which the desired enantiomer can be set free by the action of suitable agents, for example basic agents. 0066] Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry. The reference further states: [0068]. It can be advantageous to isolate or synthesize in each case the biologically more effective isomer , for example enantiomer or diastereomer, or isomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity. Since the methods of isolating and synthesizing isomers are well known in the art, and O’Sullivan teaches and suggests using such strategy to use the most biologically active enantiomer, one of ordinary skill in the art before the effective filing date of the present application would have used such strategy to make find the most effective isomer mixture as a pesticide. See the present claims 1 and 17. Regarding claim 18, O’Sullivan teaches that the typical rates of application per hectare is generally 1-2000 g/ha, and more preferably 10-600 g/ha and most preferably 50-300 g/ha, which is well within the presently claimed range. Regarding claim 19, the reference teaches that the composition comprising the compounds of formula (I) is applied to the plants, to parts thereof or the locus thereof. See [0145]. In treating the peanut plants, applying the fungicidal composition to the site on the fungus or the infection would have been prima facie obvious . Response to Arguments 07-37 AIA Applicant's arguments filed on March 12, 2026 have been fully considered but they are not persuasive in part . Applicant asserts the previous rejection fails to point out 2-trifluoromethyl-pyrid-3-yl. The elected species has been addressed in the current rejection. Applicant argues that the rejection combines the teachings from disparate portions of the references, but the teachings specifically relate to the constituents of the compound of formula (I). It would have taken only ordinary skill in the art to follow the teachings and suggestions to make and use the compounds useful against the disclosed pathological microorganisms to treat the disclosed plants. Applicant also argues that mere statement that isolating and synthesizing isomers are well known and within the skill in the art is insufficient to make a prima facie case of obviousness. In response, the examiner respectfully points out that the rejection specifically cites O’Sullivan’s teachings which indicates that the motivation for search is to find the more biologically active enantiomer in the cis isomer. The reference may not teach which enantiomer is more biologically active, but finding which of the limited number of enantiomer pairs in a racemic mixture is most biologically active would have been well within the skill in the art. Applicant also argues that the present method produces unexpected results. Applicant points out to the data in the specification which shows 79% efficacy of the Compound I against Cercospora arachidicola in peanut over a duration of 63 days after application as compared to a commercial compound, succinate dehydrogenase inhibitor SC500 with efficacy of 53 %. In response, the examiner respectfully points out that O’Sullivan directs one of ordinary skill in the art that the disclosed compounds of formula (I) and its use as a fungicide on leguminous plants; the reference also suggests finding the more biologically active isomer. Typically, unexpected results are shown in comparison between the claimed subject matter with the closest prior art to effectively rebut a prima facie case of obviousness. See MPEP 716.02 (e). The data in the specification may amount to a superior result of the compound suggested by O’Sullivan as compared to a product not previously discussed in the rejection, but it does not necessarily show unexpected results over what would have been obvious to one of ordinary skill in the art in view of the prior art. Conclusion No claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to GINA JUSTICE whose telephone number is (571)272-8605. The examiner can normally be reached M-F 9:00 AM - 5 PM. 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, BETHANY BARHAM can be reached at 571-272-6175. 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. /GINA C JUSTICE/Primary Examiner, Art Unit 1617 Application/Control Number: 17/783,859 Page 2 Art Unit: 1617 Application/Control Number: 17/783,859 Page 3 Art Unit: 1617 Application/Control Number: 17/783,859 Page 4 Art Unit: 1617 Application/Control Number: 17/783,859 Page 5 Art Unit: 1617 Application/Control Number: 17/783,859 Page 6 Art Unit: 1617 Application/Control Number: 17/783,859 Page 7 Art Unit: 1617 Application/Control Number: 17/783,859 Page 8 Art Unit: 1617 Application/Control Number: 17/783,859 Page 9 Art Unit: 1617 Application/Control Number: 17/783,859 Page 10 Art Unit: 1617 Application/Control Number: 17/783,859 Page 11 Art Unit: 1617 Application/Control Number: 17/783,859 Page 12 Art Unit: 1617
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