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 .
DETAILED ACTION
Claims 1-24 are currently pending in the instant application. 1-10, 12-16, 18, 19 and 22-24 are rejected; claims 11 and 17 are objected and claims 20 and 21 are considered allowable in this Office Action.
I. Response to Arguments
Applicant’s arguments, filed on November 4, 2025, with respect to the rejection of claims 1, 3, 5, 6, 13, 14, 16, 19, 22 and 23 under 35 USC 102(a)(1) as being anticipated by Patrian, et al. (CIPAC Symposium; June 12, 2012; Dublin, Ireland) have been fully considered but are not found persuasive. Applicants argue that regarding independent claim 1, the Patrian handout does not disclose the recited process step (a) or step (b) that is substantially free from haloalkane impurities. Applicants argue that the Patrian reference only addresses CCl4 (one haloalkane) and does not address the broader category of haloalkanes as recited in claim 1. However, the Examiner wants to point out that the Patrian reference does indeed teach the two reaction steps present in independent claim 1 as the following:
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The Examiner wants to point out that in step 2 of Patrian, et al., carbon disulfide (an organosulphur compound) is reacted with chlorine to form the compound PCMM (instant formula II) and then step 3 teaches that PCMM is then reacted with phthalimide to be converted into folpet (a compound of instant formula I wherein k is benzene). Patrian teaches that 20 formulations were analyzed and residues detected ranged from <0.2-0.7 g/kg which is equivalent to < 0.02-0.07% by weight. Applicants have not defined in the specification what amount is defined as “substantially free of” and therefore the limitation is given the broadest interpretation. The Examiner also wants to point out that “haloalkane impurities” is considered a genus and the prior art reference only has to read on one haloalkane impurity for it to be considered a 102 or 103 reference. The prior art clearly teaches carbon tetrachloride (a haloalkane) as an impurity. Therefore, the Examiner has maintained the 102(a)(1) rejection because the prior art does in fact teach the process of claim 1.
Applicants’ arguments with respect to the rejection of claims 22-24 under 35 USC 102(a)(1) as being anticipated by Canal-Raffian, et al. (Particle and Fibre Toxicology, 4:8 (2007)) have been fully considered and are persuasive. The Examiner will reject the claims under 103 instead of 102(a)(1) in this Office Action.
Applicants’ arguments with respect to the rejection of claims 22-24 under 35 USC 102(a)(1) as being anticipated by ECHA Registration of Captan (study period May 14, 2024-August 29, 2014) in view of Commission Implementing Regulation (EU) No. 540/2011 (October 7, 2008) have been fully considered and are persuasive. The Examiner will reject the claims under 103 instead of 102(a)(1) in this Office Action.
Applicants’ arguments with respect to the rejection of claims 1-3, 5-7, 9, 10, 12-16, 18, 19, 22 and 23 under 35 USC 102(a)(1) as being anticipated by Deccan Report have been fully considered and are persuasive. The Examiner will reject the claims under 103 instead of 102(a)(1) in this Office Action.
Applicants’ arguments with respect to the rejection of claims 2 and 7 under 35 USC 102(a)(1) as being anticipated by Deccan Report in view of US 2,713,058 have been fully considered and are persuasive. The Examiner has withdrawn the rejection.
III. Rejection(s)
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless -
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 3, 5, 6, 13, 14, 16, 19, 22 and 23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Patrian, et al. (CIPAC Symposium; June 12, 2012; Dublin, Ireland). The instant invention claims
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The Patrian, et al. reference teaches a process for preparing folpet (wherein K is a part of a benzene ring) with less than 0.02% of the impurity carbon tetrachloride present. This species of the process anticipates the genus process of the instant invention, wherein the process steps are as defined in claim 1.
35 USC § 103 - OBVIOUSNESS REJECTION
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 22-24 are rejected under 35 U.S.C. 103 as being unpatentable over Canal-Raffian, et al. (Particle and Fibre Toxicology, 4:8, (2007)) in view of Patrian, et al. (CIPAC Symposium; June 12, 2012; Dublin, Ireland) . Applicants claim
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The Scope and Content of the Prior Art (MPEP §2141.01)
The Canal-Raffian, et al. reference teaches teaches two commercially available formulations of folpet (wherein K is a part of a benzene ring) which have particle sizes in both formulations that are less than 5 μm in size (see page 6, column 2) which is equivalent to a D75 of 5 μm (1 μm equals 1 micron). This species of the compounds of the prior art anticipates the genus compound of the instant invention, wherein K is defined above.
The Patrian, et al. reference teaches a process for preparing folpet (wherein K is a part of a benzene ring) with less than 0.02% of the impurity carbon tetrachloride present. The prior art also teaches that carbon tetrachloride, a possible carcinogen to humans, is a relevant impurity in both folpet and captan.
The Difference Between the Prior Art and the Claims (MPEP §2141.02)
The difference between the prior art of Canal-Raffian, et al. and the instant invention is that the prior art does not teach that the compound is substantially free from haloalkane impurities but Patrian, et al. teaches that presence of carbon tetrachloride as a relevant impurity and it being less than 0.02%- 0.07% by weight.
Prima Facie Obviousness-The Rational and Motivation (MPEP §2142-2413)
In In re Crosley 72 USPQ 499 and In re Merz 1938 CD 728, it was well established that pure compositions (compounds) are unpatentable over impure compositions (compounds) if utility is the same. Applicants’ claimed utility of folpet is the same utility found in the prior art’s references. It would be obvious to prepare folpet being substantially free of haloalkane impurities (i.e., carbon tetrachloride) because the prior art of Patrian teaches folpet with < 0.02- 0.07% of the impurity present and that the impurity could be a carcinogen to humans. The motivation would be to remove as much of the carbon tetrachloride impurity as possible since it is a possible carcinogen. Therefore, it would have been prima facie obvious to one having ordinary skill in the art at the time the invention to prepare folpet substantially free of carbon tetrachloride based on the teachings of the preferred embodiments in both prior art references of Patrian, et al. and Canal-Ruffian, et al. A strong prima facie obviousness has been established.
Claims 22-24 are rejected under 35 U.S.C. 103 as being unpatentable over ECHA Registration of Captan (study period May 14, 2024-August 29, 2014) in view of Commission Implementing Regulation (EU) No. 540/2011 (October 7, 2008) . Applicants claim
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The Scope and Content of the Prior Art (MPEP §2141.01)
The ECHA Registration of Captan reference teaches Captan (wherein K is a part of a cyclohexene) which have D50 particle sizes of 12.6 μm. In accordance with Commission Implementing Regulation N. 540/2011, plant protection products containing captan as an active substance requires no more than 0.1 g/kg of carbon tetrachloride being present. 0.1 g/kg is equivalent to 0.01% weight.
The Difference Between the Prior Art and the Claims (MPEP §2141.02)
The difference between the prior art of The ECHA Registration of Captan and the instant invention is that the prior art does not teach that the compound is substantially free from haloalkane impurities.
Prima Facie Obviousness-The Rational and Motivation (MPEP §2142-2413)
In In re Crosley 72 USPQ 499 and In re Merz 1938 CD 728, it was well established that pure compositions (compounds) are unpatentable over impure compositions (compounds) if utility is the same. Applicants’ claimed utility of captan is the same utility found in the prior art’s references. It would be obvious to prepare captan being substantially free of haloalkane impurities (i.e., carbon tetrachloride) because the prior art of the Commission Implementing Regulation N. 540/2011, plant protection products containing captan as an active substance requires no more than 0.1 g/kg of carbon tetrachloride being present. The motivation would be to remove as much of the carbon tetrachloride impurity as possible since the requirement is no more than 0.01% can be present. Therefore, it would have been prima facie obvious to one having ordinary skill in the art at the time the invention to prepare captan substantially free of carbon tetrachloride based on the teachings of the preferred embodiments in both prior art references of ECHA Registration of Captan in view of Commission Implementing Regulation (EU) No. 540/2011. A strong prima facie obviousness has been established.
Claims 2 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Patrian, et al. (CIPAC Symposium; June 12, 2012; Dublin, Ireland) in view of Takumi, et al. (JPH04128261A). Applicants claim
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The Scope and Content of the Prior Art (MPEP §2141.01)
The Patrian, et al. reference teaches a process for preparing folpet (wherein K is a part of a benzene ring) with less than 0.05% of the impurity carbon tetrachloride present.
The Takumi, et al. reference teaches preparing perchloromethyl mercaptan by reacting carbon disulfide and chlorine in the presence of an acid aqueous solution which suppresses by-production of carbon tetrachloride.
The Difference Between the Prior Art and the Claims (MPEP §2141.02)
The difference between the prior art of Patrian, et al. and the instant invention is that the prior art does not teach the use of an aqueous acidic solution when preparing the compound of formula (II) but Takumi, et al. teaches the use of an aqueous acidic solution in the same reaction which suppresses the side production of CCl4.
Prima Facie Obviousness-The Rational and Motivation (MPEP §2142-2413)
It is obvious to use an aqueous acid solution when preparing the compound
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and then using the compound to prepare folpet, for example, when the art teaches the use of aqueous acidic solution with a reasonable expectation of success. The prior art teaches that using the aqueous acidic solution suppresses the formation of undesirable by-product of tetrachloride. Therefore, it would have been prima facie obvious to one having ordinary skill in the art at the time the invention to use aqueous acidic solution based on the teachings of the preferred embodiments in the prior art. For example, a skilled artisan would be motivated to prepare the compound
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by using an aqueous acidic solution for the purpose of suppressing by products as seen in as seen in the prior art reference of Takumi, et al. (JPH024128261A) and then using this compound to prepare folpet as seen in Patrian, et al. A strong prima facie obviousness has been established.
Claims 1, 3, 5, 6, 9, 10, 12-16, 18, 19, 22 and 23 are rejected under 35 U.S.C. 103 as being unpatentable over Deccan Report (Final EIA Report, Deccan Fine Chemicals (India) PVT.LTD., Project No. 1016-21-01, October 2016, pages 2-48 to 2-50) in view of Patrian, et al. (CIPAC Symposium; June 12, 2012; Dublin, Ireland). Applicants claim
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The Scope and Content of the Prior Art (MPEP §2141.01)
The Deccan Report reference teaches a process for preparing perchloronemethylmercaptan (PCMM) and folpet (wherein K is a part of a benzene ring) using the following process:
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The Patrian, et al. reference teaches a process for preparing folpet (wherein K is a part of a benzene ring) with less than 0.02% of the impurity carbon tetrachloride present. The prior art also teaches that carbon tetrachloride, a possible carcinogen to humans, is a relevant impurity in both folpet and captan.
The Difference Between the Prior Art and the Claims (MPEP §2141.02)
The difference between the prior art of Deccan Report and the instant invention is that the prior art does not teach the compound of formula I being substantially free of haloalkane impurities but Patrian, et al. teaches the presence of carbon tetrachloride as a relevant impurity and it being less than 0.02%- 0.07% by weight.
Prima Facie Obviousness-The Rational and Motivation (MPEP §2142-2413)
In In re Crosley 72 USPQ 499 and In re Merz 1938 CD 728, it was well established that pure compositions (compounds) are unpatentable over impure compositions (compounds) if utility is the same. Applicants’ claimed utility of folpet is the same utility found in the prior art’s references. It would be obvious to prepare folpet being substantially free of haloalkane impurities (i.e., carbon tetrachloride) because the prior art of Patrian teaches folpet with < 0.02- 0.07% of the impurity present and that the impurity could be a carcinogen to humans. The motivation would be to remove as much of the carbon tetrachloride impurity as possible since it is a possible carcinogen. Therefore, it would have been prima facie obvious to one having ordinary skill in the art at the time the invention to prepare folpet substantially free of carbon tetrachloride based on the teachings of the preferred embodiments in both prior art references of Patrian, et al. and the Deccan Report. A strong prima facie obviousness has been established.
IV. Objections
Dependent Claim Objections
Dependent Claims 11 and 17 are objected to as being dependent upon a rejected based claim. To overcome this objection, Applicant should rewrite said claims in an independent form and include the limitations of the base claim and any intervening claim.
V. Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Shawquia Jackson whose telephone number is (571)272-9043. The examiner can normally be reached on M-F 7AM-4PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam Milligan can be reached on (571) 270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SHAWQUIA JACKSON/Primary Examiner, Art Unit 1626