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 .
Reopening of Prosecution After Appeal Brief
In view of the appeal brief filed on 11/26/2025, PROSECUTION IS HEREBY REOPENED. New grounds of rejections are set forth below.
To avoid abandonment of the application, appellant must exercise one of the following two options:
(1) file a reply under 37 CFR 1.111 (if this Office action is non-final) or a reply under 37 CFR 1.113 (if this Office action is final); or,
(2) initiate a new appeal by filing a notice of appeal under 37 CFR 41.31 followed by an appeal brief under 37 CFR 41.37. The previously paid notice of appeal fee and appeal brief fee can be applied to the new appeal. If, however, the appeal fees set forth in 37 CFR 41.20 have been increased since they were previously paid, then appellant must pay the difference between the increased fees and the amount previously paid.
A Supervisory Patent Examiner (SPE) has approved of reopening prosecution by signing below:
/SUE X LIU/Supervisory Patent Examiner, Art Unit 1616
Status of Claims
Claims 1 and 12-13 are amended. Claim 15 is cancelled. Claims 16-19 are new.
Claims 1-14 and 16-19 are pending and being examined on merits herein.
Priority
This instant application 17999334, filed on 11/18/2022, is a 371 of PCT/EP2021/062885, filed on 05/14/2021, claims foreign priority to United Kingdom 2007418.3, filed on 05/19/2020 and to India 202111015684, filed on 04/01/2021.
Information Disclosure Statement
No new information disclosure statement (IDS) has been filed.
Claim Objections
Claim 1 is objected to because of the following informalities:
Claim 1 shows compound of formula (I) in which the group/atom letters designated for substituents are not aligned well with the bonds.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claims 1-14 and 16-19 are rejected under 35 U.S.C. 103 as being unpatentable over Mizutani et al. (US4875924, 10/24/1989), in view of Koyanagi et al. (Bioisosterism in Agrochemicals, American Chemical Society, 1995, Pg. 15-24, PTO-892) and Devendar et al. (Top Curr Chem (Z) 2017, 375:82, 1-44, in record of 04/18/2025).
Mizutani throughout the reference teaches cinnoline derivative compounds in herbicidal compositions (e.g., Title).
Regarding instant claims 1-10 and 16, Mizutani teaches a cinnoline derivative compound:
PNG
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188
230
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wherein
X can be -OH, OR1, wherein
R1 is a C1-C9 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C1-C3 alkoxy (C1-C4) alkyl group, a C1-C3 haloalkyl group, a C3-C6 cycloalkyl group, benzyl group or phenyl group;
Y is fluorine atom, chlorine atom, bromine atom, a trihalomethyl group, a C1-C6 alkoxy group or a C1-C2 alkyl group;
A is a C1-C3 polyhaloalkyl group; and
A' is hydrogen atom, fluorine atom, chlorine atom or bromine atom;
a process for preparing the same, and a herbicidal composition containing the same as an active ingredient,
a method for controlling undesired weeds using the same, and use of the same as herbicide (e.g., Abstract).
The above compound corresponds to the instantly claimed compound structure with the instant substituents as following:
X is O (corresponding to instant claims 1 and 10),
R1 is phenyl optionally substituted with R7 as fluorine atom, chlorine atom or bromine atom (halogen) and C1-C3 polyhaloalkyl group (corresponding to instant claims 1 and 2),
R3 is hydrogen or C1-C9 alkyl group (corresponding to instant claim 5), a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C1-C3 haloalkyl group, a C3-C6 cycloalkyl group or phenyl group (corresponding to instant claim 1),
R4, R5, R6 are hydrogen (corresponding to instant claims 1 and 6-7),
R7 is halogen, such as fluorine atom, chlorine atom or bromine atom (corresponding to instant claims 1 and 8-9).
Mizutani exemplifies many compounds in Tables 1-2, for instance, Compound No. 14 (Table 2, Column 13) represents OA as 4-OCF3, A’ as -H, X as OH, Y as OCH3, this resulting in compound is 5-methoxy-1,4-dihydro-4-oxo-1-[4-(trifluoromethoxy)phenyl]-3-cinnolinecarboxylic acid with a structure:
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527
435
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Greyscale
Wherein, X is O, R1 is phenyl, R3 is H, R4/R5/R6 each is H, R7 is trifluoromethoxy, the substituents with the backbone structure corresponds to a compound defined by instant claim 1 and dependent claims 2-10 of instant claim 1, except differing from instant substituent R2 group.
Regarding instant claim 16, the above compound corresponds to the first and second compounds in the claim except R2 position as S(O)nC 1-C6alkyl, S(O)nC1-C6haloalkyl, or S(O)nC3-C6cycloalky group, while it is methoxy group -OMe in Mizutani compound.
Mizutani provides more compound examples of the herbicidal cinnoline derivative compound in Tables 1-2 (Col.8; Col. 12-13), indicating that Y substituent (corresponding to R2 in instant claim) in addition to be -OCH3, it can be other alkyloxy groups, e.g., -OC2H5, OC4H9(n), OC3H7.
Regarding instant claims 11 and 17, Mizutani teaches that the cinnoline derivatives employed in herbicidal composition are usually formulated in the form of emulsifiable concentrates, wettable powders, suspensions, granules and the like in combination with auxiliary agents such as a solid carrier, liquid carrier and surface active agent, which are agriculturally acceptable formulation adjuvants (Column 9, Lines 35-42).
Regarding instant claims 12-13 and 18, Mizutani points out that cinnoline derivatives in the composition can be used in combination with insecticides, nematocides, acaricides, fungicides, and with other herbicides to improve their activity (Column 10, Lines 16-21).
Regarding instant claims 14 and 19, Mizutani teaches the method for controlling undesired weeds, comprising formulating and using the composition in soil treatment, foliage treatment or treatment under flooded condition before the emergence of weeds to area where undesired weeds grow or will grow; Soil treatment includes soil surface treatment, soil incorporation treatment, and the like. The foliage treatment includes, in addition to the treatment of the plant over the top, directed application wherein herbicides are applied only to weeds so as not to attach to crops, and the like (Column 10, Lines 3-15).
The compounds taught in Mizutani as shown above having C1-C6 alkoxy group, e.g., O-C1-C4alkyl or-O-Me as in the example above, differing from instant compound formula I of position R2 substituent group S(O)nC1-C6alkyl, S(O)nC1-C6haloalkyl, S(O)nC3-C6cycloalkyl; n is 0, 1 or 2, as recited in instant claim 1 and dependent claims 2 and 5-10, or S(O)nC1-C3alkyl, S(O)nC1-C3haloalkyl, S(O)nC3-C4cycloalkyl as recited in instant claim 3, or methylsulfanyl, methylsulfonyl, ethylsulfanyl, ethylsulfonyl, 2,2,2 trifluoroethyl-sulfanyl, 2,2,2-trifluoroethylsulfonyl, cyclopropylsulfanyl, or cyclopropylsulfonyl, as recited in instant claim 4, or 5-methylsulfanyl or 5-methylsulfonyl as recited in the first two compounds in instant claim 16.
Koyanagi throughtout the reference teaches bioisosterism in agrochemicals design (e.g., Abstract), indicating that bioisosteres are groups or molecules which have chemical and physical similarities producing broadly similar biological properties. Koyanagi specifies that bivalent -O- and -S- belong to classical bioisosteres (Table I, Pg. 16), and -O- and -S(O)n- belong to non-classical bioisosteres (Table II, Pg. 17). Therefore, Koyanagi teaches that the compounds exemplified above in Mizutani having -O-C1-C4alkyl group, e.g., -O-CH3, are bioisosteres of the instant compounds having -S-C1-C4alkyl or -S(O)n-C1-C4alkyl as R2 substituents.
Koyanagi summarizes that bioisosterism has remained useful as one of the practical chemorational approaches and its position as the best possible approximation for explaining and predicting chemical and biological similarities and analogies has not been replaced by any defendable assumptions. The simple and qualitative concept may be most useful to the agrochemists responsible for new agrochemicals exploration with respect to the point that a chemical structure of a compound, whose activity may be predicted, can be assembled by means of solely visual sense based on one’s own chemorational design without any computer support. The concept of bioisosteres can be extensively utilized by agrochemists who put an appropriate chemorational emphasis on one of its multiple-faces, which the chemical structure originally possesses, depending upon the necessity of design for new agrochemicals exploration (Conclusion, Pg. 23). This provides scientists in the field a motivation to modify the Mizutani structure to swap the -OC1-C6alkyl group, such as -O-Me, into the isomers containing -S-C1-C4alkyl or -S(O)n-C1-C4alkyl, e.g., -S-methyl or methylsulfanyl, resulting in the instant compounds in claims 1-10 and 16.
In addition to Koyanagi’s teaching, Devendar throughout the reference teaches sulfur-containing agrochemicals and the important tool in modulating properties of new crop protection compounds by introduction of sulfur atoms into an active ingredient (e.g., Abstract).
Devendar teaches the significant importance of sulfur-containing agrochemicals in crop protection and states that the introduction of a sulfur-containing moiety may enhance the selectivity, sometimes with a reduction in mammalian toxicity (e.g., Pg. 81, bottom paragraph -Pg. 82, 2nd paragraph). Devendar points out that in the past years, sulfur-containing active ingredients have played a significant role in the field of modern crop-protection research and development. The effect of sulfur on the biological activity of agrochemicals such as herbicides, insecticides, fungicides, and plant growth regulators, has earned sulfur a unique place in the toolbox of the agrochemical chemist (Pg. 82, 2nd paragraph), and based on Devendar’s survey up to June 2017 on a specific website database, among 514 listed insecticides, 206 have sulfur (>40%); out of 543 herbicides, 178 contain sulfur (>32%); in listed 424 fungicides, 122 have sulfur (>28%); in total 53 nematicides, 36 contain sulfur (>67%) and in 216 listed acaricides, 98 have sulfur (>45%) (Pg. 82, 2nd paragraph). Devendar exemplifies conversions from various groups into sulfur-containing compounds throughout the reference.
It would have been obvious to one of ordinary skill in the art prior to filing date to take into consideration of the teachings of Koyanagi and Devendar to modify the Mizutani herbicidal compound to arrive at current invention. Because as presented above, Koyanagi teaches that the Mizutani cinnoline derivative compound examples containing substituent of -O-C1-C4alkyl group, e.g., -O-CH3, are bioisosteres of S(O)n-C1-C4alkyl, or -S-C1-C4alkyl such as methylsulfanyl, and Koyanagi teaches that bioisosteres are groups or molecules which have chemical and physical similarities producing broadly similar biological properties, modification of the -O-CH3 group into a sulfur-containing -S-CH3 (methylsulfanyl) or S(O)n-CH3 would constitute similar biological properties as herbicides. Further, as Koyanagi states that bioisosteres can be extensively utilized by agrochemists who put an appropriate chemorational emphasis on one of its multiple-faces, which the chemical structure originally possesses, depending upon the necessity of design for new agrochemicals exploration, indicating modifying bioisosteres for new agrochemicals is a well-known. Moreover, Devendar teaches the significance and broad usage of sulfur-containing compounds in agricultural crop protection, research and development, especially Devendar indicates that introduction of a sulfur-containing moiety may enhance the selectivity, sometimes with a reduction in mammalian toxicity, and Devendar specifies that the effect of sulfur on the biological activity of agrochemicals such as herbicides, insecticides, fungicides, and plant growth regulators, has earned sulfur a unique place in the toolbox of the agrochemical chemist to explore and introduce sulfur-containing compounds. In light of both Koyanagi and Devendar’s teaching, modifying substituent groups, e.g., -OCH3 group from Mizutani into -S-CH3 (methylsulfanyl) or S(O)n-CH3, would have been obvious to one of ordinary skill in the art for reasonable expectation of success.
Furthermore, “Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
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 1-14 and 16-19 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-14 and 16-21 of copending Application No. US17999249, filed 11/18/2022, in view of in view of Koyanagi et al. (Bioisosterism in Agrochemicals, American Chemical Society, 1995, Pg. 15-24, PTO-892) and Devendar et al. (Top Curr Chem (Z) 2017, 375:82, 1-44, in record of 04/18/2025).
US’249 recites a compound formula (I) in claims 1-10 with exemplary species in claims 16-21, sharing the same backbone structure with X, R1, R3-R10 groups overlapping and generally the same as the compound in instant claims 1-10 and 16.
US’249 recites the herbicidal composition comprises an adjuvant (claim 11) (corresponding to instant claims 11 and 17), at least one additional pesticide (claim 12) (corresponding to instant claims 12 and 18) as a herbicide or herbicide safener (claim 13) (corresponding to instant claim 13). US’249 directs a method of controlling unwanted plant growth, comprising applying the compound in formula (I) to unwanted plants or to the locus thereof (claim 14) (corresponding to instant claims 14 and 19).
US’249 differs from instant claim of R2 substituent: in US’249 R2 is cyano, C1-C6alkylcarbonyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxyC2-C6alkenyl, C2-C6alkenyloxyC1-C6alkyl, -CR11=N-OR10, phenyl, phenoxy, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N, O and S, heterocyclyl, or heterocyclyloxy, wherein the heterocyclyl moieties are a 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, wherein the phenyl, phenoxy, heteroaryl, heterocyclyl, and heterocyclyloxy moieties may each be optionally substituted with 1, 2 or 3 groups, which may be the same or different, represented by R8 (claim 1-3, 16-21); while in instant invention, R2
is S(O)nC1-C6alkyl, S(O)nC1-C6haloalkyl, S(O)nC3-C6cycloalkyl; n is 0, 1 or 2, as recited in instant claim 1, or S(O)nC1-C3alkyl, S(O)nC1-C3haloalkyl, S(O)nC3-C4cycloalkyl as recited in instant claim 3, or methylsulfanyl, methylsulfonyl, ethylsulfanyl, ethylsulfonyl, 2,2,2 trifluoroethyl-sulfanyl, 2,2,2-trifluoroethylsulfonyl, cyclopropylsulfanyl, or cyclopropylsulfonyl, as recited in instant claim 4 and some of the mentioned substituents present in the specific compounds of claim 16.
Koyanagi throughtout the reference teaches bioisosterism in agrochemicals design (e.g., Abstract), indicating that bioisosteres are groups or molecules which have chemical and physical similarities producing broadly similar biological properties. Koyanagi specifies that bivalent -O- and -S- belong to classical bioisosteres (Table I, Pg. 16), and -O- and -S(O)n- belong to non-classical bioisosteres (Table II, Pg. 17). Therefore, Koyanagi teaches that the compounds recited in US’249 with C1-C6alkoxyC2- C6alkenyl (as -O-C1-C6alkyl-substituted with C2-C6alkenyl group) are bioisosteres of the instant compounds having -S-C1-C6alkyl or -S(O)n-C1-C6alkyl as R2 substituents.
Koyanagi summarizes that bioisosterism has remained useful as one of the practical chemorational approaches and its position as the best possible approximation for explaining and predicting chemical and biological similarities and analogies has not been replaced by any defendable assumptions. The simple and qualitative concept may be most useful to the agrochemists responsible for new agrochemicals exploration with respect to the point that a chemical structure of a compound, whose activity may be predicted, can be assembled by means of solely visual sense based on one’s own chemorational design without any computer support. The concept of bioisosteres can be extensively utilized by agrochemists who put an appropriate chemorational emphasis on one of its multiple-faces, which the chemical structure originally possesses, depending upon the necessity of design for new agrochemicals exploration (Conclusion, Pg. 23). That would provide scientists a motivation to modify the compounds in US’249 to explore new agrochemicals in current invention.
In addition, Devendar throughout the reference teaches sulfur-containing agrochemicals and the important tool in modulating properties of new crop protection compounds by introduction of sulfur atoms into an active ingredient (e.g., Abstract).
Devendar teaches the significant importance of sulfur-containing agrochemicals in crop protection and states that the introduction of a sulfur-containing moiety may enhance the selectivity, sometimes with a reduction in mammalian toxicity (e.g., Pg. 81, bottom paragraph -Pg. 82, 2nd paragraph). Devendar points out that in the past years, sulfur-containing active ingredients have played a significant role in the field of modern crop-protection research and development. The effect of sulfur on the biological activity of agrochemicals such as herbicides, insecticides, fungicides, and plant growth regulators, has earned sulfur a unique place in the toolbox of the agrochemical chemist (Pg. 82, 2nd paragraph), and based on Devendar’s survey up to June 2017 on a specific website database, among 514 listed insecticides, 206 have sulfur (>40%); out of 543 herbicides, 178 contain sulfur (>32%); in listed 424 fungicides, 122 have sulfur (>28%); in total 53 nematicides, 36 contain sulfur (>67%) and in 216 listed acaricides, 98 have sulfur (>45%) (Pg. 82, 2nd paragraph). Devendar exemplifies conversions from various groups into sulfur-containing compounds throughout the reference.
It would have been obvious to one of ordinary skill in the art prior to filing date to take into consideration of the teachings of Koyanagi and Devendar to modify US’249 herbicidal compound to arrive at current invention. Because as presented above, Koyanagi teaches that -C1-C6alkoxy-C2- C6alkenyl in US’249 are bioisosteres of the instant compounds having -S-C1-C6alkyl or -S(O)n-C1-C6alkyl as R2 substituents, and Koyanagi teaches that bioisosteres are groups or molecules which have chemical and physical similarities producing broadly similar biological properties, such modification would constitute similar biological properties as herbicides. Further, as Koyanagi states that bioisosteres can be extensively utilized by agrochemists who put an appropriate chemorational emphasis on one of its multiple-faces, which the chemical structure originally possesses, depending upon the necessity of design for new agrochemicals exploration, indicating modifying bioisosteres for new agrochemicals is a well-known. Moreover, Devendar teaches the significance and broad usage of sulfur-containing compounds in agricultural crop protection, research and development, especially Devendar indicates that introduction of a sulfur-containing moiety may enhance the selectivity, sometimes with a reduction in mammalian toxicity, and Devendar specifies that the effect of sulfur on the biological activity of agrochemicals such as herbicides, insecticides, fungicides, and plant growth regulators, has earned sulfur a unique place in the toolbox of the agrochemical chemist to explore and introduce sulfur-containing compounds. In light of both Koyanagi and Devendar’s teaching, modifying -C1-C6alkoxy-C2-C6alkenyl in US’249 into isomers of -S-C1-C6alkyl or -S(O)n-C1-C6alkyl to make instant compounds would have been obvious to one of ordinary skill in the art for reasonable expectation of success.
Furthermore, “Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
This is a provisional nonstatutory double patenting rejection.
Response to Pre-Appeal Remarks
Appellant’s remarks filed on 11/26/2025 have been fully considered, and pre-brief appeal conference participants have made decision to reopen prosecution of the case, and new ground of rejections have presented in this office action. Please take entire office action as a complete response to the remarks.
Conclusion
No claim is allowed.
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/DX.Z./Examiner, Art Unit 1616
/SUE X LIU/Supervisory Patent Examiner, Art Unit 1616