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 .
Continued Examination Under 37 CFR 1.114
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 08/21/25 has been entered.
Claim Objections
Claim 7 is objected to because of the following informalities: the claim recites “a weight percentage of the compound of general formula I.” However, as claim 7 is directed to a fungal composition comprising the compound of general formula I, since the compound is necessarily present it inherently has a weight percentage as such “the weight percentage” was the correct way to word this phrase in the claim and the “a weight percentage” should be changed back to “the weight percentage”.
Claim 7 is objected to because of the following informalities: it recites “A fungal composition” and should recite “A fungicidal composition” because fungal is a typo.
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.
Claim(s) 1-2, 7-9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nakamura et al. (US20100261735).
Determination of the scope and content of the prior art
(MPEP 2141.01)
Regarding claims 1-2, Nakamura broadly teaches fungicidal compounds which encompass applicant’s claimed compounds as per their broadly claimed and disclosed compound scope (see entire document; [0006-0008]; claims), wherein for instance the compounds of formula I and/or I-α read on those instantly claimed wherein A/Aα is phenyl which is substituted with 2 X/Xα, wherein the first X/Xα which corresponds to the instant R2 is/can be the claimed haloalkoxy, and the other X/Xα which corresponds to applicant’s R1 can be the claimed halogen, alkyl, etc. as claimed, and wherein W1 is applicant’s O, and Nakamura’s R1 and R2 correspond to the instant R3 and R4 are/can be the claimed alkyl or haloalkyl, etc. and wherein Nakamura’s B is any heterocyclic ring, excluding pyridyl, which is substituted with Y, wherein Y overlaps with the same substituents on the instantly claimed B, and Nakamura clearly prefers some B groups which are the same as instantly claimed, e.g. Nakamura specifically exemplifies that their B can be pyrazole (1,2-diazole) groups substituted with Y, wherein Y is preferably the claimed halogen, alkyl or haloalkyl, etc., e.g. B9 of Nakamura is the instant B15, and as such one of ordinary skill in the art could follow the teachings of Nakamura to form the claimed compounds with a reasonable expectation that these compounds would also exhibit fungicidal activity just as disclosed in applicant’s disclosure (see entire document; e.g. [0006-0008]; [0010-0014]; [0245-0246]; [0237-0279]; [0260-0264]; [0269]; claims; compounds cited herein). Especially since the courts have previously determined, “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. ‘An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.’” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979), and that “Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious.” In rePayne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979)
Nakamura specifically exemplifies structurally similar compounds, e.g. I-371 through I-375 which only differ from the claimed compounds in that the R2 is alkyl instead of the claimed haloalkyl and Nakamura’s B21 is different from the claimed B groups (see entire document; e.g. [0006-0008]; [0010-0014]; [0245-0246]; [0237-0279]; [0260-0264]; [0269]; claims; compounds cited herein). However, it would be obvious to form the claimed compounds wherein the alkyloxy group of Nakamura’s X which corresponds to the instant OR2 is changed to the claimed haloalkoxy group, e.g. a OCF3 group as in I-255 and wherein B21 of Nakamura is changed to B9 which is the same as the instant B15, etc. as claimed in claims 1-2 because in this case the equivalency of B9 for B21 is recognized in the prior art which is required for these types of obviousness rejections see for instance In reRuff, 256 F.2d 590, 118 USPQ 340 (CCPA 1958). Thus, it would be obvious to select Nakamura’s B9 to change for B21 in Nakamura’s I-371 through I-375 (wherein Nakamura’s B9 is the same as the instant B15) because Nakamura teaches that they are equivalents of one another and are useful for the same purpose of forming fungicidal compounds which is the same intended use disclosed in the instant specification. Further, the courts have previously determined, “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. ‘An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.’” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
Regarding claims 7-9, Nakamura teaches wherein their compounds which overlap in scope and/or are structurally similar are formulated into compositions/fungicidal compositions as active ingredients and agriculturally acceptable carriers, wherein the active agents/Nakamura’s overlapping compounds/structurally similar compounds are present in amounts of 0.001% to 90% by weight, and wherein these compositions are used in methods of controlling fungal diseases, specifically plant fungal diseases by applying to the growth medium/soil in doses of 10 to 100,000 g/ha, preferably 200 to 20,000 g/ha when applied to soil/growth medium which overlap those instantly claimed, and wherein fungal diseases being controlled are the same as instantly claimed (see entire document; abstract; [0174]; [0171]; [0172]; [0173]; claims, etc.).
Ascertainment of the difference between prior art and the claims
(MPEP 2141.02)
Nakamura does not teach an express example of the claimed compounds. Though they do broadly teach some of the instantly claimed fungicidal compounds within their broad disclosure and therefore the claimed method of controlling a fungal disease which is discussed above.
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
It would be obvious form the claimed compounds when looking to Nakamura because the instantly claimed compounds are broadly claimed within Nakamura’s disclosure of the claimed compounds and broadly disclosed by Nakamura for the same fungicidal use. It would have been obvious to modify applicant’s OR2 to be the claimed OCF3 and/or haloalkoxy, and applicant’s R3 to be haloalkyl as is now required by applicant’s claims and to alter applicant’s B to be the claimed B15 which corresponds to B9 of Nakamura, because Nakamura teaches that all of their disclosed B groups are equivalents of one another, and Nakamura teaches examples wherein applicant’s OR2 is OCF3 (e.g. I-255) and teaches examples teaches/claims that their B can be any heterocycle except pyridyl and can be substituted with the same substituents instantly claimed and wherein these compounds within their disclosure exhibit fungicidal activity which is the same activity of the instantly claimed compounds which is not surprising based on the teachings of Nakamura. Further, Nakamura specifically teaches that their claimed/exemplified B groups include the claimed B15 which is B9 in Nakamura and it would be obvious to substitute the B21 of Nakamura for Nakamura’s B9 which is the instantly claimed B15 for the reasons discussed above.
It also would have been obvious to one of ordinary skill in the art at the time of the instant filing to have optimized the amount of active agents to read on the claimed ranges, and to optimize the application rate of g/ha to read on the claimed ranges because Nakamura teaches ranges which overlap those instantly claimed and they broadly disclose/claim the claimed compounds and their examples render obvious the claimed compounds for the above discussed reasons, and it is known, “In the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.’” In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934, and further “Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. ‘[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.’” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)
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.
Claim(s) 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nakamura et al. (US20100222337), and further in view of Patani et al. (Chem. Rev., 1996, 96, 3147-3176).
Determination of the scope and content of the prior art
(MPEP 2141.01)
Regarding claim 5, Nakamura ‘337 broadly teaches the claimed compound (See entire document; abstract; e.g. [0009-0016]; [0017-0028]; Table 1; claims, etc.) and specifically exemplifies structurally similar compounds, e.g. 1-20 which differs from the instantly claimed compounds because their B which corresponds to the instant B is 2-CF3, 3-pyridyl and as such it differs in that the haloalkyl group in the 2 position differs by the presence of an additional F atom from the instantly claimed CHF2 group in the claimed B2, and because Nakamura ‘337’s X is 4-OiPr which is taught to be an equivalent to the claimed cyclopentyl oxy group as Nakamura ‘337 clearly teaches examples wherein the cyclopentyloxy group is in the same position as the OiPr group of I-20, see for instance 1-72 (see entire document; Table 1: 1-20, 1-72, [0009-0016]; [0017-0028]; claims), and the rest of Nakamura ‘337’s 1-20, i.e. Nakamura ‘337’s R1 and R2 which correspond to the instant R3 and R4 are both methyl as instantly claimed, and X is also 2-Me which corresponds to the instant R1, and Nakamura ‘337 teaches wherein their B can be substituted by haloalkyl group which would include the claimed CHF2 of applicant’s B2 (see entire document; e.g. Table 1, 1-20, 1-72; [0018]; [0009]; [0191, see (5)-(7)]; [0009-0016]; [0017-0028]; claims). Nakamura ‘337 clearly teaches wherein the cycloalkyl as in the cycloalkyloxy groups of their X can be the claimed cyclopropyl, and Nakamura ‘337 also specifically exemplifies examples of their compounds which are substituted with a 4-cyclopentyloxy group which would also correspond to the claimed OR2 group, e.g. 1-72 (see entire document; e.g. Table 1, 1-20, 1-72; [0018]; [0009]; [0191, see (5)-(7)]; [0009-0016]; [0017-0028]; claims).
Ascertainment of the difference between prior art and the claims
(MPEP 2141.02)
Nakamura ‘337 does not specifically teach the instantly claimed compounds, specifically having the claimed CHF2 group on their B group that is structurally very similar to applicant’s B2 group, but as discussed above teaches very structurally similar compounds. However, it would have been obvious to formulate the claimed compounds when looking to Nakamura ‘337 because for instance Nakamura ‘337 does teach wherein their X can be the claimed O-R2 and specifically exemplifies compounds having cyclopentyloxy group at the same 4 position.
However, this deficiency in Nakamura ‘337 is addressed by Patani which teaches that H atoms and F atoms are classical bioisosteres of one another and are commonly employed replacements of one another (pg. 3149, f vs h replacements).
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 replaced the OiPr group in compound 1-20 for the claimed cyclopentyloxy group as the OR2 group because Nakamura ‘337clearly teaches this group as an equivalent for their disclosed OiPr group as they have examples wherein the cyclopentyloxy group is in the same 4 position of the phenyl ring as the OiPr group of compound 1-20 as discussed above, and that this substituent is useful for forming fungicidal compounds having a very close structure to those instantly claimed. Thus, it would be obvious to change out the OiPr group in 1-20 for the claimed cyclopentyloxy group which is taught by Nakamura ‘337 at the 4-position of 1-20 in order to form the claimed compounds in order to form additional fungicidal compounds, and it also would be obvious to replace at least one H atom, specifically all 3 H atoms on the R1 methyl group of Nakamura ‘337 with fluoro groups, i.e. as in 1-20 in order to form the claimed the claimed halogenated methyl/halogenated alkyl R1 groups because F and H are known classical bioisosteres of one another are a common/routine substitution which is routinely made by one of ordinary skill in the art in order to form additional compounds having the same biological activity as is taught by Patani.
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.
Allowable Subject Matter
Claims 3-4 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Specifically, while the compounds of claims 3-4 are very broadly disclosed within the broadest disclosure of Nakamura, there are no close exemplified compounds which would not require multiple changes to various groups. For instance, looking at I-371 through I-375 which differ from the claimed compounds in that the R2 is alkyl instead of the claimed haloalkyl and Nakamura’s B21 is different from the claimed B groups. Thus, the B21 in these compounds would have to be changed to another B group, e.g. Nakamura’s B7 and this B7 group would then itself have to be further modified, e.g. exchange an F for an H atom in the CF3 group, in order to read on the claimed groups or change the Cl to a F atom, and it would be too much hindsight to make all of the required changes to achieve the instantly claimed compounds, because why select/make the specifically claimed B-groups which would require switching out for instance B21 which has many examples in Nakamura for B7 and then it would require a bioisosteric replacement of H for the F at the CF3 group to form the claimed CHF2 group or it would require the replacement of Cl for F in order to achieve the claimed B11 or B24, and further would require at least one of Nakamura’s X to be haloalkoxy, as is discussed above in order to be the instantly claimed OR2. As such, all of these changes would not be obvious because they would require too much hindsight and too much picking and choosing in order to achieve the claimed compounds when looking at the closest prior art Nakamura.
Response to Arguments/Remarks
Applicants amendments to the claims have overcome and/or rendered moot all previous grounds of rejection. These amendments have prompted the new grounds of rejection presented herein. Applicants arguments insofar as they pertain to the new grounds of rejection are addressed herein and are not persuasive at this time. Applicants argue that the previous Nakamura reference, Nakamura ‘337, no longer reads on claims 1-4 and 7-9 due to applicant’s amendments. The examiner agrees and as discussed above this grounds of rejection has been rendered moot. However, Nakamura ‘337 does still render obvious claim 5 for the reasons discussed above because the examiner disagrees that the claimed cyclopentyl groups are not rendered obvious by the isopropyl group at R2 of Nakamura ‘337 and the rest of Nakamura’s disclosure for the reasons discussed above in this new/updated grounds of rejection.
As applicants arguments related to the previous prior art and previous rejections which are now moot due to applicant’s amendments, these arguments are not further addressed herein.
Conclusion
No claims are allowed.
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/ERIN E HIRT/Primary Examiner, Art Unit 1616