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 .
Election/Restrictions
Applicant’s election without traverse of Group I, drawn to a benzimidazole compound or a salt thereof; and an insecticide and acaricide, and Compound 1-47 having the structure of:
PNG
media_image1.png
115
166
media_image1.png
Greyscale
as the elected species of benzimidazole compound or salt thereof in the reply filed on January 14, 2026 is acknowledged.
Claims 20-29 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention and species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on January 14, 2026.
Expansion of Election of Species Requirement
A reasonable and comprehensive search of the elected species conducted by the Examiner
discover a prior art by Kolluri et al. that anticipates the claimed invention, wherein the prior art teaches
a compound 783; However, it is noted that the prior art does not teach the elected species. In light of this discovery, the search is expanded to the subject matter of the benzimidazole compound or a salt thereof to include compound 783 of Kolluri et al. in addition to the elected species such, that it does not encompass the full scope of the claims.
Priority
The instant application 18/547,667 filed on August 23, 2023 is a 371 of PCT/CN2022/077277 filed on February 22, 2022, which claims priority to, and the benefits of Foreign Application No. CN202110204832.5 filed on February 23, 2021.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Failure to provide a certified translation may result in no benefit being accorded for the non-English application.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 8/23/2023 and 11/6/2024 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Please note that foreign references without an English translation but have an English
translation of the abstract will only have the abstract considered by the Examiner.
Status of the Claims
Acknowledgement is made of the receipt and entry of the amendment to the claims filed on January 14, 2026, wherein claims 1-12 are cancelled; claims 13-32 are newly added.
Claims 13-32 are pending. Claims 20-29 are withdrawn.
Claims 13-19 and 30-32 are under examination in accordance with the elected species and inventions along with the expanded species sets forth in the Expansion of Election of Species Requirement section above.
Claim Interpretation
The terms “insecticide” and “acaricide” recite in the preamble of claims 30-32 are reasonably construed to be an intended use of the product positively recite; and therefore, if the prior art meets the structural limitation of the product, it is capable of performing the intended use. See MPEP 2111.02.
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 13-14 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.
Regarding claims 13, the limitations of “at least one group” and “a bonded benzene ring” in the recitation of "and optionally, any two adjacent groups of Y1, Y2, Y3, Y4 and Y5 form one group, and at least one group and a bonded benzene ring are cyclized with or without at least one heteroatom to form at least one 3- to 8 membered ring" (see page 3, line 6-8) and the recitation of “and optionally, any two adjacent groups of Z1, Z2, Z3, and Z4 form one group, and at least one group and a bonded benzene ring are cyclized with or without at least one heteroatom to form at least one 3- to 8-membered ring” (see page 5, line 13-15) lacks antecedent basis, because there terms are not recited prior to said phrase. For instance, any two adjacent groups of Y1, Y2, Y3, Y4 and Y5 or any two adjacent groups of Z1, Z2, Z3, and Z4 forms one group, which is singular, it is not clear what are the additional groups being referred to in the context of “at least one group”. It is also not clear what is being referred to as “a bonded benzene ring”, is applicant intending to introduce a new benzene ring being fused to the “one group”? There is insufficient antecedent basis for these limitations in the claim. In order to advance prosecution, the claim is being examined by the Examiner to the extent that any two adjacent groups of Y1, Y2, Y3, Y4 and Y5 or any two adjacent groups of Z1, Z2, Z3, and Z4 together form a 3- to 8 membered ring with or without at least one heteroatom.
Regarding claim 14, the limitations of “at least one group” and “a bonded benzene ring” in the recitation of "and optionally, any two adjacent groups of Y1, Y2, Y3, Y4 and Y5 form one group, and at least one group and a bonded benzene ring are cyclized with or without at least one heteroatom to form at least one 3- to 8 membered ring" (see page 6, line 19-21) and the recitation of “and optionally, any two adjacent groups of Z1, Z2, Z3, and Z4 form one group, and at least one group and a bonded benzene ring are cyclized with or without at least one heteroatom to form at least one 3- to 8-membered ring” (see page 7, line 9-11) lacks antecedent basis, because there terms are not recited prior to said phrase. For instance, any two adjacent groups of Y1, Y2, Y3, Y4 and Y5 or any two adjacent groups of Z1, Z2, Z3, and Z4 forms one group, which is singular, it is not clear what are the additional groups being referred to in the context of “at least one group”. It is also not clear what is being referred to as “a bonded benzene ring”, is applicant intending to introduce a new benzene ring being fused to the “one group”? There is insufficient antecedent basis for these limitations in the claim. In order to advance prosecution, the claim is being examined by the Examiner to the extent that any two adjacent groups of Y1, Y2, Y3, Y4 and Y5 or any two adjacent groups of Z1, Z2, Z3, and Z4 together form a 3- to 8 membered ring with or without at least one heteroatom.
Claim Rejections - 35 USC § 102
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 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 13-14 and 30 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kolluri et al. (WO 2021/022061 A1; cited in the IDS filed on 11/6/2024).
Kolluri et al. teaches a compound 783 having the structure of:
PNG
media_image2.png
51
64
media_image2.png
Greyscale
is an exemplary AhR ligand compound of Formulae I, IA, IB, IC, ID, and IE (see e.g., p. 64, line 19, Compound-783; Table 1, No. 783). Kolluri et al. further teaches a pharmaceutical composition comprising the AhR ligand of the disclosure (see e.g., p. 6, line 27-28). Kolluri et al. further teaches a physiologically or pharmaceutically acceptable carrier or vehicle can be used to formulate the compound for administration and can be selected according to the mode of administration (see e.g., p. 23, line 7-9).
Please note the compound 783 taught by Kolluri et al. is a compound represented by formula (I)
PNG
media_image3.png
123
197
media_image3.png
Greyscale
, wherein R is
PNG
media_image4.png
50
54
media_image4.png
Greyscale
(C3 cycloalkyl); Y1, Y2, Y3 are each a hydrogen; Y4 and Y5 together form a
PNG
media_image2.png
51
64
media_image2.png
Greyscale
(phenyl, a 6-membered ring); Z1, Z2 and Z4 are each a hydrogen; Z3 is Cl (a halogen); and therefore, the pharmaceutical composition comprising said compound anticipates claim 30.
Therefore, the claimed invention is being anticipated by Kolluri et al.
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 13-14 and 30-32 are rejected under 35 U.S.C. 103 as being unpatentable over Kolluri et al. (WO 2021/022061 A1) as applied to claims 13-14 and 30 above, and further in view of Chaikof et al. (US 2021/0147390 A1).
The teachings of Kolluri et al. are sets forth above and applied as before.
Kolluri et al. does not teach the content of the active ingredient ranges from 1 wt% to 99 wt% in claim 31. Kolluri et al. also does not teach the content of the active ingredient ranges from 5 wt% to 60 wt% in claim 32.
Chaikof et al. teaches a pharmaceutical composition comprising the compound of Formula (I) or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient (see e.g., claims 1, 59); wherein the compound can non-covalently bind to aryl hydrocarbon receptors and induce aryl hydrocarbon receptor activity (see e.g., [0005]). Chaikof et al. further teaches relative amount of the active ingredient, the pharmaceutically acceptable carrier, and/or any additional ingredient in the pharmaceutical composition will vary, depending upon the identity, size, and/or condition of the subject treated and further depending upon the route by which the composition is to be administered; by way of example, the composition may comprise between 0.1% and 100% (w/w) active ingredient (see e.g., [0452]).
Regarding claims 31-32, it would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to incorporate the compound 783 of Kolluri et al. at an amount between 0.1% and 100% (w/w) taught by Chaikof et al. to arrive at the claimed invention. One would have been motivated to do so, because Chaikof et al. teaches a pharmaceutical composition comprising 0.1% and 100% (w/w) of a compound of formula (I) with aryl hydrocarbon receptor (AhR) activation activity can be administered to a subject. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that compound 783 of Kolluri et al. has the same or substantially similar AhR activation activity as the compound of Formula (I) of Chaikof et al.; and therefore, 0.1% and 100% (w/w) of said compound 783 can successfully be used to formulate a pharmaceutical composition without any appreciable loss of activity.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Claims 13-19 and 30-32 are rejected under 35 U.S.C. 103 as being unpatentable over Cui et al. (CN106946790 A; cited in the IDS filed on August 23, 2023), in view of Frick et al. (US 3,624,100).
Please note Cui et al. cited in the IDS filed on August 23, 2023 is written in foreign language, but applicant only provides an English translation of the abstract. Therefore, a machine translation has been provided in the previous Office Action mailed on November 20, 2025, the specific portions cited in this instant office action will refer to the sections of the machine translation.
Cui et al. teaches a compound of Example 20, 2-phenyl-1-ethylsulfonylbenzimidazole, having the structure of:
PNG
media_image5.png
110
149
media_image5.png
Greyscale
is an exemplary compound of 1,2-substitued benzimidazole derivative (see e.g., [0099]). Cui et al. further teaches the 1,2-substitued benzimidazole derivative
PNG
media_image6.png
140
176
media_image6.png
Greyscale
, wherein R1 is, inter alia, hydrogen or halogen; R2 is, inter alia, hydrogen or halogen; R3 is, inter alia, hydrogen or halogen; R4 is, inter alia, hydrogen or halogen; R5 is alkylsulfonyl azide or arylsulfonyl azide; R6 is, inter alia, aryl or aryl derivative (see e.g., [0013]). Cui et al. further teaches benzimidazole derivatives are a class of nitrogen-containing heterocyclic organic compounds with a wide range of uses, and have important application values in, inter alia, pesticides (see e.g., [0004]).
Cui et al. does not teach the elected species of benzimidazole compound or salt thereof.
Frick et al. teaches compound 38, 2-(3',5'-bis-trifluoromethyl-phenyl)-5-trifluoro-methyl-benzimidazole, is an exmplary benzimidazole derivatives of general formula I having insecticidal and acaricidal properties (see e.g., Table I, Ex No. 38; Col. 1, line 6-7 and 57). Frick et al. further teaches insecticidal and acaricidal agents which contain these new benzimidazole derivatives as active substances and, in particular, serve to combat keratin-eating insects and their larvae, as well as the use of these active substances and the agents containing them for combating insects and spider (see e.g., Col. 1, line 6-14). Frick et al. further teaches the agents according are produced in the known way by intimately mixing the active substances with solid or liquid carriers and distributing agents (see e.g., Col. 7, line 68-70). Frick et al. further teaches a 20 percent solution of 2-(4'-chlorophenyl)-4,5,6-trichloro-7-bromo-benzimidazole in 2-methoxyethanol in Example 2 (see e.g., Col. 8, line 33-36). Please note 2-(4'-chlorophenyl)-4,5,6-trichloro-7-bromo-benzimidazole is also an exemplary benzimidazole derivatives of general formula I (see e.g., Table I, Ex No. 22). Frick et al. further teaches percentages are given therein by weight (see e.g., Col. 8, line 16-17).
In the present case, the difference between the compound of Example 20 of Cui et al. and the claimed compound (the elected species of benzimidazole compound or salt thereof) is that the prior art compound contains unsubstituted phenyl rather than a 3,5-bistrifluoromethyl phenyl shown below (see shaded):
PNG
media_image7.png
188
491
media_image7.png
Greyscale
.
It would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to select a compound of Example 20 of Cui et al., and then modify said compound by replacing the unsubstituted phenyl with a 3,5-bistrifluoromethyl phenyl taught by Frick et al. as the aryl derivative to arrive at the claimed invention. One would have been motivated to do so, because Cui et al. teaches a list of R6, including aryl and aryl derivative, that can be interchange to arrive at a 1,2-substitued benzimidazole derivative with application values in pesticides; and Frick et al. teaches the compound 38, 2-(3',5'-bis-trifluoromethyl-phenyl)-5-trifluoro-methyl-benzimidazole, is a benzimidazole derivative having insecticidal and acaricidal properties. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that the compound of Example 20 of Cui et al. and the compound 38 of Frick et al. are structurally similar with similar utilities ( application in pesticides), and therefore, said compound of example 20 modified in view of the phenyl derivative of Frick et al. by substituting the phenyl with a 3,5-bistrifluoromethyl phenyl as the aryl derivative would have successfully arrive at the compound that is similarity useful for combating pests, and that also renders obvious the limitation in claim 30.
Regarding the limitation of “wherein the content of the active ingredient ranges from 1 wt% to 99 wt% based on the total weight of the insecticide and acaricide” in claim 31, and the limitation of “wherein the content of the active ingredient ranges from 5 wt% to 60 wt% based on the total weight of the insecticide and acaricide” in claim 32, 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 (Fed. Cir. 1990). In the present case, it would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to arrive at a 20 wt% solution of the modified compound of example 20 of Cui et al. and Frick et al. sets forth above. One would have been motivated to do so, because Frick et al. teaches the insecticidal and acaricidal agents which contain the benzimidazole derivatives as active substances can be produced by intimately mixing said active substance with solid or liquid carriers and distributing agents, and specifically exemplified a 20 wt% solution of a benzimidazole derivative, 2-(4'-chlorophenyl)-4,5,6-trichloro-7-bromo-benzimidazole, in 2-methoxyethanol. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that the modified compound of example 20 of Cui et al. and Frick et al. sets forth above can be mixed with 2-methoxyethanol as the liquid carriers to prepare a 20 wt% solution without any appreciable loss of activity.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the
time the application was filed, absent factual evidence to the contrary.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Chihyi Lee whose telephone number is (571)270-0663. The examiner can normally be reached Monday - Friday 8:30 am - 5:00 pm EST.
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, Amy L. Clark can be reached at (571) 272-1310. 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.
/CHIHYI LEE/Examiner, Art Unit 1628 /JEAN P CORNET/Primary Examiner, Art Unit 1628