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WO 2015/123193 Al 20 August 2015 (20.08.2015) P O P C T

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WO 2015/123193 Al 20 August 2015 (20.08.2015) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2015/123193 Al 20 August 2015 (20.08.2015) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 487/04 (2006.01) A01N 43/56 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US2015/015 183 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 10 February 20 15 (10.02.2015) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 61/938,872 12 February 2014 (12.02.2014) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant: E. I. DU PONT DE NEMOURS AND COM¬ GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, PANY [US/US]; 1007 Market Street, Wilmington, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, Delaware 19898 (US). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventor: TAGGI, Andrew Edmund; 2 1 Tremont Court, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Newark, Delaware 1971 1 (US). SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (74) Agent: STERNBERG, Charlene G.; E. I. du Pont de GW, KM, ML, MR, NE, SN, TD, TG). Nemours and Company, Legal Patent Records Center, Published: Chestnut Run Plaza 721/2640, 974 Centre Road, PO Box 2915 Wilmington, Delaware 19805 (US). — with international search report (Art. 21(3)) (54) Title: FUNGICIDAL BENZODIPYRAZOLES ( 1) (57) Abstract: Disclosed are compounds of Formula (1), including all geometric and stereoisomers, tautomers, iV-oxides, and salts thereof, wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention. TITLE FUNGICIDAL BENZODIPYRAZOLES FIELD OF THE INVENTION This invention relates to certain benzodipyrazoles, their tautomers, their N-oxides, salts and compositions, and methods of their use as fungicides. BACKGROUND OF THE INVENTION The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different sites of action. Certain benzodipyrazole derivatives and their preparation have been disclosed see, e.g., Journal fuer Praktische Chemie (Leipzig) 1978, 320(6), 991-998, Dyes and Pigments 1991, 17(2), 113-121, Bollettino Chimico Farmaceutico 1995, 134(11), 616-619 and Journal of Heterocyclic Chemistry 1970, 7(5), 1131-1 135. JP59215358 and JP60092356 disclose certain benzodipyrazoles as colorants. SUMMARY OF THE INVENTION This invention is directed to compounds of Formula 1 (including all stereoisomers), tautomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as fungicides: wherein 2 R and R are each independently H, C -C alkyl, C -C haloalkyl, C2-C alkenyl, C -C alkynyl, C -C cyanoalkyl, C -C hydroxyalkyl, C3-Cg cycloalkyl, C3-C halocycloalkyl, C C g cycloalkylalkyl, C Cg alkylcycloalkyl, C^-Cg alkylthio, Cj -Cg haloalkylthio, C Cg alkylsulfinyl, C^-Cg haloalkylsulfmyl, C Cg alkylsulfonyl, C -C haloalkylsulfonyl, C -C alkylthioalkyl, C -C haloalkylthioalkyl, C -Cg alkylsulfmylalkyl, C -Cg haloalkylsulfmylalkyl, C2-Cg alkylsulfonylalkyl, C -Cg haloalkylsulfonylalkyl, Cj -Cg alkoxy, C j -Cg haloalkoxy, C2-C alkoxyalkyl, C2-Cg haloalkoxyalkyl, C3-C cycloalkoxy, Cj -Cg alkylamino, C2-Cg dialkylamino, C2-Cg alkylaminoalkyl or C3-C8 dialkylaminoalkyl; or -(CH2) nW each W is independently a phenyl ring optionally substituted with up to 3 substituents independently selected from halogen and C1-C3 alkyl; R3, R4 , R5 and R6 are each independently H, cyano, hydroxy, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 cyanoalkyl, C2-C4 alkenyl, C2-C4 alkynyl, - cycloalkyl, C3-C6 halocycloalkyl, C1-C3 alkoxy, -C3 haloalkoxy, C2-C4 alkoxyalkyl or C2-C4 haloalkoxyalkyl; R7 and R8 are each independently H, C^-C alkyl, C3-C5 cycloalkyl, C4-C8 cycloalkylalkyl, C4-C8 alkylcycloalkyl, C2-Cg alkoxyalkyl, C2-Cg alkylcarbonyl, C4-Cg cycloalkylcarbonyl or C2-Cg alkoxycarbonyl; and n is 1 or 2; provided that the compound of Formula 1 is other than: 2,4,6,8-tetrahydro-2,6-dimethylbenzo[l,2-c:4,5-c']dipyrazole-3,7-diol; 2,4,6,8-tetrahydrobenzo[l,2-c:4,5-c']dipyrazole-3,7-diol; 2,3a,4,6,7a,8-hexahydro-2,6-bis(2-hydroxyethyl)benzo[l,2-c:4,5- c']dipyrazole-3,7-dione; 3,7-dihydroxybenzo[l,2-c:4,5-c']dipyrazole-2,6(4 H ,8H )-diethanol; or 2,4,6,8-tetrahydro-3,7-dimethoxy-2,6-dimethylbenzo[l,2-c:4,5-c']dipyrazole. More particularly, this invention pertains to a compound selected from compounds of Formula 1 (including all stereoisomers), tautomers and N -oxides and salts thereof. This invention also relates to a fungicidal composition comprising (a) a compound of the invention (i.e. in a fungicidally effective amount) or a compound selected from 2,4,6,8- tetrahydro-2,6-dimethylbenzo[l,2-c:4,5-c']dipyrazole-3,7-diol, 2,4,6,8-tetrahydrobenzo[ 1,2- c:4,5-c']dipyrazole-3,7-diol, 2,3a,4,6,7a,8-hexahydro-2,6-bis(2-hydroxyethyl)benzo[l,2- c:4,5-c']dipyrazole-3,7-dione, 3,7-dihydroxybenzo[l ,2-c:4,5-c']dipyrazole-2,6(4 H ,8H)- diethanol and 2,4,6,8-tetrahydro-3,7-dimethoxy-2,6-dimethylbenzo[l,2-c:4,5-c']dipyrazole; and (b) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention also relates to a fungicidal composition comprising (a) a compound of the invention or a compound selected from 2,4,6,8-tetrahydro-2,6-dimethylbenzo[l,2-c:4,5- c']dipyrazole-3,7-diol, 2,4,6,8-tetrahydrobenzo[l,2-c:4,5-c']dipyrazole-3,7-diol, 2,3a,4,6,7a,8-hexahydro-2,6-bis(2 -hydroxyethyl)benzo[l,2-c:4,5-c']dipyrazole-3,7-dione, 3,7-dihydroxybenzo[l ,2-c:4,5-c']dipyrazole-2,6(4 H ,8H )-diethanol and 2,4,6,8-tetrahydro- 3,7-dimethoxy-2,6-dimethylbenzo[l,2-c:4,5-c']dipyrazole; and (b) at least one other fungicide (e.g., at least one other fungicide having a different site of action). This invention further relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of the invention (e.g., as a composition described herein) or a compound selected from 2,4,6,8-tetrahydro-2,6-dimethylbenzo[ 1,2- c:4,5-c']dipyrazole-3,7-diol, 2,4,6,8-tetrahydrobenzo[l,2-c:4,5-c']dipyrazole-3,7-diol, 2,3a,4,6,7a,8-hexahydro-2,6-bis(2-hydroxyethyl)benzo[l,2-c:4,5-c']dipyrazole-3,7-dione, 3,7-dihydroxybenzo[l,2-c:4,5-c']dipyrazole-2,6(4 H ,8H )-diethanol and 2,4,6,8-tetrahydro- 3,7-dimethoxy-2,6-dimethylbenzo[l,2-c:4,5-c']dipyrazole. This invention also relates to a composition comprising a compound of Formula 1, an N -oxide, or a salt thereof, and at least one invertebrate pest control compound or agent. DETAILS OF THE INVENTION As used herein, the terms "comprises", "comprising", "includes", "including", "has", "having", "contains", "containing", "characterized by" or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, method, article, or apparatus. The transitional phrase "consisting of excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consisting of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
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