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 .
Claimed Priority
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Receipt of claim amendments and remarks filed on 12/10/2025 is acknowledged. Claims 3, 8 and 13 have been canceled. Claims 1-2, 4-7, 9-12 and 14-20 are pending. Claim 1 is independent.
Election/Restriction
Applicant has amended the claims in a manner that changed claimed dependency. Applicant elected without traverse Group I, drawn to claims 1, 4-7, 9-11, 14 and 17, in the reply filed on December 10, 2025.
As the catalyst species, Applicant elected the catalyst of Formula 1, and as the reaction route, the reaction between compound II and compound III
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for preparing azoxystrobin of formula I. The election reads on claims 1, 4-7, 14 and 17.
Claims 9-11 do not read on the elected invention because they pertain to making an intermediate that is not relevant to the elected reaction of compound II and compound III. The process of claims 9-11 excludes the elected reaction of compound II with compound III.
Accordingly, claims 2, 9-12, 15-16 and 18-20, and subject matter of claim 1 outside of the examined scope, are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 on December 10, 2025
The requirement is still deemed proper and is therefore made FINAL.
Claims 1, 4-7, 14 and 17 are treated on the merits in this First Office action.
Claim Rejections - 35 USC § 112
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.
Claims 1, 4-7, 14 and 17 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 “
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”, and the claim also recites "
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", which are the narrower statements of the range/limitation;
claim 1 recites the broad recitation “
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”, and the claim also recites “
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”, which is the narrower statement of the range/limitation;
claim 6 recites the broad recitation “is used in an amount from 0.01 mol% to 10 mol%”, and the claim also recites “preferably from 0.05 mol % to 5 mol%”, which is the narrower statement of the range/limitation;
in claim 6, the phrase "preferably, step 1) and step 2)" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
claim 6 recites the broad recitation “from -10 to 150”, and the claim also recites “preferably from -5 to 120, more preferably 0 to 100C”, which is the narrower statement of the range/limitation;
claim 6 recites the broad recitation “from 1 to 24 h”, and the claim also recites “preferably from 3 to 18 h”, which is the narrower statement of the range/limitation;
in claim 6, the phrases “preferably selected from the group consisting of”, “for example”, “most preferably”,
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render the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
claim 6 recites the broad recitation “
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”, and the claim also recites “
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”, which is the narrower statement of the range/limitation;
claim 6 recites the broad recitation “
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”, and the claim also recites “for example,
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”, which is the narrower statement of the range/limitation;
claim 14 recites the broad recitation “not less than 98%”, and the claim also recites “preferably not less than 99%”, which is the narrower statement of the range/limitation;
claim 17 recites the broad recitation “not higher than 0.3%”, and the claim also recites “preferably not higher than 0.2%, more preferably not higher than 0.1%. most preferably not higher than 0.05%”, 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 6 recites “the hydrocarbons include…”, the esters include…”, “the ethers include…”, “the ketones include…”, “the amides include…”, and “the alcohols include…”. This is ambiguous in a selection list because the list is open-ended. Terms “having”, “including” and “comprising” allow for inclusion of indefinite number of members. However, a Markush grouping is a closed group of alternatives, i.e., the selection is made from a group “consisting of” rather than “comprising”, “having” or “including”. Pursuant to MPEP 2173.05(h), if a Markush grouping requires a material selected from an open list of alternatives, the claim should generally be rejected under 35 USC 112(b) as indefinite because it is unclear what other alternatives are intended to be encompassed by the claim.
Claim 7 is ambiguous. It recites that step 1) is something that is not step 1) in claim 1. Also, as step 4) it has the process that is step 1) in claim 1. It is also not in accordance with what is step 2) in claim 5.
Claim 14 is ambiguous because it doesn’t recite the percent type (weight %, molar %, etc.)
Claim 17 is ambiguous because claim 17 depends of claim 1 and, the process in claim 1 cannot possibly produce the impurities described in claim 17.
All dependent claims are rejected for the same issues.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 4 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 4 states that compound III of claim 1 is compound IIIa, or compound IIIb, or a mixture of compound IIIa and compound IIIb. This does not further limit the subject matter of claim 1 because in claim 1, compound III can only be compound IIIa, or compound IIIb, or a mixture of compound IIIa and compound IIIb.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claims 1, 4-7, 14 and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Kini et al. (WO2020/212919) and Beveridge et al. (WO2008/043978A1) or Yao (CN114195723- PD March 18, 2022), in view of Turner (Inorg. Chem. 2013, 52, 7344-7351), Zhang (Dalton Trans., 2017, 46, 899), US 9,234,109B2, Schareina (Organic Process Research & Development 2008, 12, 537–539) and Zhong (Synthetic Communications 2004, 34:23, 4301-4311).
The two steps described in the claims for making azoxystrobin are very well documented in the art. The prior art commonly proposes new catalysts for the synthesis of azoxystrobin, to obtain the compound in high yield, high purity and in a cost-effective manner. See the references cited in this application’s specification, see also references cited in the prior art used in this Office action.
Kini et al.
Kini (and references cited therein) taught the same steps for the synthesis of azoxystrobin (I) substantially free of dimer impurities.
The preparation of azoxystrobin (I) proceeds via the compound of formula (II)
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in presence of a catalyst selected from
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The reaction is carried at a temperature from
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or 70°C to 100°C, for a period of about 1 to 12 hrs (at least in p. 16). Thus,
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prepares azoxystrobin of formula (I)
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. See whole document.
Per page 14 of the reference, the above process could be carried
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The preparation of intermediate of formula (II) is performed by
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.
Particularly, the process comprises:
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Step (a) is carried out in presence of a base, for example, potassium carbonate and sodium methoxide, and a solvent, for example, MIBK, at a temperature of about 50°C to 75°C. The catalyst was used in amount of 0.05 mol % in the examples.
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See at least pages 6, 17 and 22-24. Additionally, the dimer impurity could be reduced below 0.15 wt% (p. 27), and azoxystrobin is claimed to be obtained having purity of at least 99% and reduced content of dimer impurity of less than 0.1wt%. See claim 20.
Beveridge et al.
Beveridge taught the same two steps of the claimed reaction as follows:
Etherification with cyanophenol
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in the presence of the catalyst 1,4-diazabicyclo[2.2.2]octane (DABCO) or its salts;
and the formation of intermediate (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylic acid methyl ester and methyl (E)-2-hydroxyphenyl-3,3-dimethoxypropionate by the following reaction:
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(See pages 10-11). Mixtures of precursors could be expected and the appropriate conversion was known, as explained in page 5 of the prior art.
In the first step, solvents used are described in pages 6-9, which include DMF and MIBK. Organic and inorganic bases used include potassium carbonate, and DBU (p. 8 and examples).The catalyst (DABCO) is used in an amount of between 0.5 and 5 mol% (see 2.6 mol% in examples); reaction temperatures are typically from 60°C to 95°C, and reaction times are from 1 h to 280 minutes (see p. 9 and examples). Yields of 92%, 98.6%, 99.7%, etc., were obtained (see at least pages 11-12).
Yao et al.
Yao (CN114195723- PD March 18, 2022) taught the same step for preparing azoxystrobin from 2-cyanophenol:
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with improved N-alkyl cyclic amine catalysts of the formula
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, such as N-methylpyrrole or N-methylpiperidine, at 1 mol%, or 3 mol% or 5 mol%, with the use of potassium carbonate or sodium carbonate, at reaction temperatures of 60-120C and reactions times of 5-15h. See pages 2-3 of the machine translation.
Benefits of using the proposed catalysts are taught:
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1-methyl imidazole
1-methyl imidazole is a catalyst/ligand known to promote etherification reactions of haloaryl compounds with phenols.
For example, Turner (Inorg. Chem. 2013, 52, 7344-7351) taught that 1-methylimidazole promoted the etherification reaction of hydroxyphenol with 2-bromopyridine, and further, of the intermediate thereof with 1,3-diiodophenyl:
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. See Scheme 1.
Zhang (Dalton Trans., 2017, 46, 899) taught that 1-methylimidazole promoted the etherification reaction of p-alkoxyphenol with 6,6’-dibromo-2,2’-bipyridine
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:
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(Figure 1).
US 9,234,109B2 disclosed the etherification of 3-pentadecylphenol with 2,4-dinitrochlorobenzene in methyl ethyl ketone in the presence of 1-methylimidazole. See Example X at column 28.
Schareina (Organic Process Research & Development 2008, 12, 537–539) taught that 1-methylimidazole promoted the etherification reaction of hydroxyphenol with a substituted bromophenyl compound:
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.
Zhong (Synthetic Communications 2004, 34:23, 4301-4311) taught that a salt of 1-methylimidazole promoted the following etherification reaction:
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The secondary references teach the same type of etherification reactions with catalysts based on 1-methylimidazole. The list of references regarding etherification reactions with catalysts based on 1-methylimidazole is not exhaustive.
Ascertainment of the difference between the prior art and the claims (MPEP § 2141.02)
All the steps of the process, including the use of the same bases, solvents, mol% of catalyst, reaction temperatures and reaction times, were known. The difference between the prior art and the claimed process is the catalyst used.
Finding of prima facie obviousness – rationale and motivation (MPEP § 2142-2413)
One of ordinary skill in the art is a chemist practitioner with the knowledge and skills of the authors of the references cited in this action. The artisan knew that 1-methylimidazole is a cyclic amine catalyst used in the same type of etherification reactions that are used to prepare azoxystrobin. Particularly, in view of the genus of cyclic amine catalysts involved in the preparation of azoxystrobin of Yao, the artisan would have been motivated to use 1-methylimidazole, or its salts, as catalysts in the preparation of azoxystrobin of the primary references with the expectation of obtaining improved results. Replacement of one known similar catalyst for another used in the same type of reactions would have been obvious.
The Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper "functional approach" to the determination of obviousness as laid down in Graham. See MPEP 2143.
Examples of rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Here at least exemplary rationales (A), (B) and (G) apply.
Regarding the limitations in claim 14 and 17, these claims do not require more than the use of the claimed catalyst. As above, the use of 1-methylimidazole, or its salts, as catalysts in the preparation of azoxystrobin of the primary references would have been prima facie obvious. The catalyst would have provided a purity of no less than 99% and a reduced content of dimer impurity of less than 0.1 wt% because this is a latent property present in the use of 1-methylimidazole as catalyst in the same reaction. Pursuant to MPEP 2145 II: “Prima facie obvious is not rebutted by merely recognizing additional advantages or latent properties present but not recognized in the prior art”. Since the obvious process is the same as the claimed process, the properties claimed must be necessarily present. Moreover, the improved processes of the primary references taught that using cyclic amine catalysts could provide a purity of at least 99% and reduced content of dimer impurity of less than 0.1 wt%
Conclusion
Claims 1, 4-7, 14 and 17 are rejected. No claim is in condition for allowance.
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/VALERIE RODRIGUEZ-GARCIA/Primary Examiner, Art Unit 1621 02/20/2026