Title - OXADIAZOLINE COMPOUNDS OR SALTS THEREOF, AGRO-HORTICULTURAL FUNGICIDES CONTAINING THE COMPOUNDS AND METHODS FOR THEIR USE

Abstract

In the production of agricultural and horticultural crops or similar, the damage caused by diseases is still significant, and due to factors such as the emergence of diseases resistant to existing medications, the development of agro-horticultural fungicides is desired. This document provides an agro-horticultural fungicide and a method of its use; an active ingredient thereof is a compound represented by the general formula (1) or salts thereof, {where X 1 , X 2 , X 3 and X 4 A, B, and Y indicate a hydrogen atom or similar; Y indicates a single bond or carbonyl group or similar; Q indicates an alkyl group C. 1-6 or hetero ring or similar, R 5 and R 6 indicate a hydrogen atom or alkyl group C 1-6 or similar}.

Description

DESCRIPTION Oxadiazoline compounds and salts thereof, agricultural and horticultural fungicides containing the compounds and methods for their use Technical field

[0001] The present invention relates to an agricultural and horticultural fungicide containing an oxadiazoline compound or a salt thereof as the active ingredient, and a method for its use. Previous technique

[0002] Patent Document 1 describes that certain oxadiazole derivatives have fungicidal activity against fungi that cause plant diseases. Furthermore, although Patent Document 2 and Patent Document 1 indicate a method for synthesizing oxadiazoline that has a trifluoromethyl group, these documents do not disclose or suggest that said compound has fungicidal activity against fungi that cause plant diseases. List of appointments Patent document

[0003] [Patent document 1] document W02C17 / 055473 [Patent document 2] document W02003 / 028729 [Non-patent document 1] Synthesis 2011, 21, 34263428 Compendium of the invention Technical Problem

[0004] In the production of agricultural and horticultural crops or similar, the damage caused by diseases is still significant and, due to factors such as IF-2020-86290883-APN-ANP#INPI Page 1 of 122 Given the emergence of diseases resistant to existing medicines, the development of new agro-horticultural fungicides is desired. Means to solve the problem

[0005] As a result of intensive research to develop new fungicides, the present inventors found that the compound for the general formula (I) of the present invention or _ina of its salts is useful as an agro-horticultural fungicide to complete the present invention.

[0006] Namely, the present invention relates to the following: [1] A compound represented by the general formula (I) or salts thereof: [Chemical formula 1] [where A indicates a single link or the following structure A1; A2; A3; A4; A5; A6 or A7:] [Chemical formula 2) A1A1A3A4Λ5A6A7 B indicates a single bond; oxygen atom; C(RX) (R2) or carbonyl group. And it indicates a single bond; oxygen atom; C (R1) (R2) or N(R3} . R1 and R2 each independently denote (to) a hydrogen atom; IF-2020-86290883-APN-ANP#INPI Page 2 of 122 (a2) a halogen atom; (a3) an alkyl group (Ci-Ce) ; (a4) an alkoxy group (Ci-Ce); or (a5) a haloalkyl group (Cj-Ce); R1 and R2 can form a cyclopropyl group with a carbon atom to which they are attached. R3 indicates (bl) a hydrogen atom; (b2> an alkyl group (Ci-Ce); (b3> an alkoxy group (Ci-C$); (b4) a cycloalkyl group (C3~Cs) ; (b5) an alkylcarbonyl group (Ci-C$) ; (b6) an alkoxycarbonyl group (Ci-CtJ ; (b7) an alkenyl group (Cz-Cs) ; {b8) an alkynyl group (Ca—Cg) ; or (b9) a cycloalkyl (Cj—Ce) alkyl group (Ci-Cg) . Q indicates {el} a hydrogen atom; {c2) an alkyl group (Cj—Ce) ; (c3) an alkenyl group (Cz-Ce) ; (c4) an alkynyl group (Cz—Ce) ; (c5) a cycloalkyl group {Cz-Ce}; (c6) an alkoxy group (Ci—Ce>; (c7) a haloalkyl group (Ci-Ce) ; (c8) a haloalkenyl group (C2-Ce); (c9) a halcalquinyl group (C2-C6); (clO) a halocycloalkyl group (C3—Ce); (cll) a haloalkoxy group (Ci-Ce); (cl2) a group Ra{Rb)N (where Ra Rh each independently indicates a hydrogen atom / alkyl group (Ci-Ce)t, alkenyl group (Cz-Cü), alkynyl group (C2-C6), cycloalkyl group (C3—Ce), alkoxy group (Ci—Ce), haloalkyl group (Ci-Ce), cycloalkyl group {C3-Ce) Page 3 of 122 IF-2020-86290883-APN-ANP#INPI alkyl (Ci-Ce) , phenyl group, alkoxy group (Ci-Ce) alkyl (Ci-Ce) > dialkoxy group (Ci-C$) alkyl (C1-C5) , cyanoalkyl group (Ci-Ce) , alkylthio group (Ci-Cg) alkyl (Ci-Ce) , dialkylamino group (Cj-Ce) alkyl 1C1Cg), alkylcarbonyl group (Ci-Ce), alkoxycarbonyl group (Ci-Ce) alkyl (Ci-Cg) , phenylcarbonyl group or benzyl group); (cl3) an aryl group; (c!4) an aryl group each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Cg), alkoxy group (Ci-Ce), cycloalkyl group (C3-Cs), haloalkyl group (Ci-Cg), haloalkoxy group (Ci-Cg), halocycloalkyl group (Ci-Cg), alkylthio group (Ci-Cg), alkylsulfinyl group (Ci-Cg), alkylsulfonyl group (Ci-Cg), haloalkylthio group (Ci-Cg), haloalkylsulfinyl group (Ci-Ce), haloalkylsulfonyl group (Ci-Cg), Ra(Rb)N group (where Ra and Rb are the same as the above), alkoxycarbonyl group (Ci-Cg), and group Ra(Rb) Ncarbonyl (where Ray Rbson are the same as above); (cl5) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring; (cl6) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Cg), alkoxy group (Ci-Ce), cycloalkyl group (C3-Cg), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Ce), halocycloalkyl group (C3-Cs), alkylthio group (Ci-Cs), alkylsulfinyl group (Ci-Ce), alkylsulfonyl group (Ci-Cg), haloalkylthio group (Ci-Ce), haloalkylsulfinyl group IF-2020-86290883-APN-ANP#INPI Page 4 of 122 (Ci—Ce}thaloalkylsulfonyl group (Ci-C$)tRa(Rb)N group (where Ray Rbson are the same as the previous ones), alkylthio group (Ci-Ce>) alkyl (C:—C«) , phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl group (C1-C5) and Rd(Rb)Ncarbonyl group {where Ray Rbson are the same as the previous ones); (cl7) an arylalkyl group (Ci-Cs) ; (c!8) an arylalkyl group (Ci-Ce) each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (C1-C5), cycloalkyl group (C1-C5), haloalkyl group (C1-C5), haloalkoxy group (C1-C5), halocycloalkyl group (C1-C5), alkylthio group (C1-C5), alkylsulfinyl group (C1-C5), alkylsulfonyl group (C1-C5), haloalkylthio group (C1-C5), haloalkylsulfinyl group (C1-C5), haloalkylsulfonyl group (C1-C5), Ra(Rb)N group (where Ra and Rb are the same as the above), group alkoxycarbonyl (Ci—Ce) and Ra group<R’°> Ncarbonyl (where R* and Rb are the same as before); (cl9) an alkyl group (Ci-Ce) of a 5- to 6-membered hetero ring or fused hetero ring of 8 to 10 members; (c20) a 5- to 6-membered hetero ring alkyl group or 8- to 10-membered fused hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (Ci-Ce), cycloalkyl group (C3-C6), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Ce), halocycloalkyl group (C3-C5), alkylthio group (CiCfi), alkylsulfinyl group (Ci-Ce), alkylsulfonyl group (Ci-Ce), haloalkylthio group (Ci-Ce), group IF-2020-86290883-APN-ANP#INPI Page 5 of 122 haloalkylsulfinyl (Ci-Ce), haloalkylsulfonyl group (Ci-Ce), Ra(Rb)N group (where Ray and Rb are the same as the previous ones), alkylthio (Ci-Cs) alkyl (Ci-Cg) group, phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl group (C^-Cg) and Ra(Rb)Ncarbonyl group (where Rd and Rb are the same as the previous ones); (c21) an alkyl group (Ci-Cg) each independently having in the chain 1 to 3 substituents selected from the group consisting of a cyano group, alkoxy group (Ci-Cg), Ra(Rfc)N group (where Rdy and Rbson are the same as the above), alkylthio group (Ci-Cg), alkylsulfinyl group (Ci-Cgi) and alkylsulfonyl group (CiC6}; (c22) a group RcON=C (Rd) NH (where Rcy Rd each independently denotes a hydrogen atom or alkyl group (Ci-Ce)} ; or (c23) a 3-ethoxyimincazetidin-l-yl group. R5 indicates (di) a hydrogen atom; id2) an alkyl group (Ci-Cs) ; (d3) an alkylcarbonyl group (Ci-Ce) ; (d4) an alkoxycarbonyl group (Ci-Cé); or (d5) a benzyl group. He claims a hydrogen atom. X1, X2, X3, and X4 each independently indicate (f1> one hydrogen atom; (f2> a halogen atom; (f3) a cyano group; (f4) a nitro group; (f5) an alkyl group iCi-Cg) ; (f6) a cycloalkyl group (Cj-Cé); (f7) an alkoxy group (Ci-Cg); IF-2020-86290883-APN-ANP#INPI Page 6 of 122 (f8) a haloalkyl group (C1-C&); (f9) a haloalccxi (Ci-Ce) group; (f10) a halocycloalkyl group (C3-C5); (fll) an alkylthio (Ci-Ce) group; (I12) an alkylsulfyryl group (Ci-Cs) ; (f!3) an alkylsulfonyl (Ci-Cg) group; (f!4) a haloalkylthio (Ci-Có) group; (fl5) a haloalkylsulfinyl group (Ci-Ce); or (fl6) a haloalkyisulfonyl group (Ci-Cg))}> [2J The compound according to point [1J above or salts thereof, where A is a single bond c the following structure A1; L2; L5; Aug A7: [Chemical formula 3] A1AJA5A6A7 R1 and R2 each independently are (al) a hydrogen atom; (a2) a halogen atom; or {a4) an alkoxy group (Ci-Cg) , R3es (bl) a hydrogen atom; (b2) an alkyl group (Ci—Ce) ; (b3) an alkoxy group (Ci-Ce); (b4) a cycloalkyl group {Cu-Ce); (b7) an alkenyl group (Cz-Ce) ; (b8) an alkynyl group (Cz-Ct) ; or (b9) a cycloalkyl group (Cj-Ce) alkyl {Ci-Ce) , Q is (the) a hydrogen atom; (c2> an alkyl group (Ci-Ce); (c5) a cycloalkyl group (C3-C6); IF-2020-86290883-APN-ANP#INPI Page? of 122 (c6) an alkoxy group (Ci-Ce); (c7) a haloalkyl group (Ci-Cd; (cl2) a group Ra(Rb)N (where and Rb each independently indicate a hydrogen atom / alkyl group (Ci-Ce) , alkenyl group (C2-C6)t, alkynyl group (C2-C5), cycloalkyl group (Cu-Ce), alkoxy group (Ci—Ce) , haloalkyl group (Ci-Ce), cycloalkyl group (C3—Ce) alkyl (Ci-C&) , phenyl group, alkoxy group (Ci—Ce) alkyl (Ci-Ce), dialkoxy group (Ci-Cs) alkyl (Ci-Ce)f, cyanoalkyl group (C-.-Cg), alkylthio group (Ci-Cs) alkyl (Ci-Cs) , dialkyl group (Ci—Ce) alkyl (CiCs) , alkylcarbonyl group (Cj-Ce) , alkoxycarbonyl group (Cj-Ce) alkyl (Ci-Ce) tphenylcarbonyl group or benzyl group); (cl4) an aryl group each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Co), alkoxy group (Ci-Ce), cycloalkyl group (Cu-Ce), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Ce), halocycloalkyl group (C3-C6), alkylthio group (Ci-Ce), alkylsulfinyl group (Ci-Ce), alkylsulfonyl group (Cj-Cs), haloalkylthio group (Ci-Ce), haloalkylsulfinyl group (Ci-Cs) / haloalkylsuiphonyl group (Ci-Ce), R*(Rb)N group (where Ray and Rb are the same as the above), alkoxycarbonyl group (Cj-Ce), and group Ra(Rb)Ncarbonyl (where Ray and Rb are the same as above); (cl5) a hetero ring of 5 to 6 members or a fused hetero ring of 8 to 10 members; (6) a 5- to 6-membered hetero ring or 8- to 10-membered hetero-fused ring each independently having on the ring 1 to 3 substituents selected from the group consisting of an atom of IF-2020-86290883-APN-ANP#INPI Page 8 of 122 halogen, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (Ci-Cs), cycloalkyl group (Ci-Ce), haloalkyl group (Ci-C6), haloalkoxy group (Ci-Ce), halocycloalkyl group (C3-C5), alkylthio group (Ci-Ce), alkylsulfinyl group (Ci-C6), alkylsulfonyl group (Ci-Cs), haloalkylthio group (Ci-C6), haloalkylsulfinyl group (Ci-C5), haloalkylsulfonyl group (C1-C5), Rs(Rb)K group (where Rf and Rb are the same as above), alkylthio group (Ci-C6), alkyl (Ci-C6), phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl group (Ci-Cg) and Ra(Rb)Ncarbonyl group {where Ray Rb are the same as the previous ones); (c!9) an alkyl group (Ci-Cs) of a 5- to 6-membered hetero ring or fused hetero ring of 8 to 10 members; (c20) a 5- to 6-membered hetero ring alkyl group or 8- to 10-membered fused hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C5) alkyl group, (C1-C5) alkoxy group, (C3-C6) cycloalkyl group, (C3-C6) haloalkyl group, (C1-C6) haloalkoxy group, (C1-C6) halocycloalkyl group, (C1-C6) alkylthio group, (C1-C5) alkylsulfinyl group, (C1-C5) alkylsulfonyl group, (C1-C6) haloalkylthio group, (C1-C5) haloalkylsulfinyl group, (C1-C6) haloalkylsulfonyl group, (C1-C6) haloalkylthio group, (C1-C5) haloalkylsulfinyl group, (C1-C6) haloalkylsulfonyl group, (C1-C6) haloalkylsulfonyl group, Ra(Rb)N (where R5 and Rb are the same as above), alkylthio (Ci-Ce) group, alkyl (Ci-Ce) group, phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl (Ci-Ce) group and Ra(Rb)Ncarbonyl group (where Ra and rosonios are the same as above); (c21) an alkyl group (Ci-Ce) each independently having in the chain 1 to 3 substituents IF-2020-86290883-APN-ANP#INPI Page 9 of 122 selected from the group consisting of a cyano group, alkoxy group (Ci-Ce), Ra(Rb)N group (where Ruy Rbson are the same as the previous ones), alkylthio group (Ci-C&), alkylsulfinyl group (Ci-C6) and alkylsulfonyl group (CiCe); (c22) an RCON=C (R¿) NH group (where Rcy Rd each independently denotes a hydrogen atom or alkyl group (Ci-Ce)); or (c23) a 3-ethoxyiminoazetidin-l-yl group, R5 is (di) a hydrogen atom; (d2) an alkyl group (Ci-Cs); or (d5) a benzyl group, X1, X2, X3, and X4 are (fl) a hydrogen atom, [3] The compound according to point [1] or [2] above or salts thereof, where R1 and R2 each independently are (a1) a hydrogen atom; or (a4) an alkoxy group (Ci-Ce) , R3 is (b1) a hydrogen atom; (b2> an alkyl group íCi-C$); or (b3) an alkoxy group (Ci-Cs) , Q is (the) a hydrogen atom; (c2) an alkyl group ;Ci-Ce); (c5) a cycloalkyl group (Ca-Ce); (c6) an alkoxy group (Ci-Ce); (c7) a haloalkyl group (Ci-C$); (cl2) a group Ra(Rb)f (where Rdy and Rb each independently indicate a hydrogen atom, alkyl group (Cj—Ce), alkenyl group (C2-C5), alkynyl group IF-2020-86290883-APN-ANP#INPI Page 10 of 122 (C2-C6) t cycloalkyl group (Cn-Ce) , alkoxy group {Ci-Cg), haloalkyl group (Ci-C$) , cycloalkyl group (Cj-Ce) alkyl (Ci-Có) , phenyl group, alkoxy group (Ci-Ce) alkyl (Ci-Cg), dialkoxy group (Ci-Cfi) alkyl (Cj-Ce), cyanoalkyl group (Ci-Cc) , alkylthio group (Ci-Cg) alkyl (Ci-Cg), dialkylamino group (Ci-Cg) alkyl (CiCe>talkylcarbonyl group (Ci-Ce) , alkoxycarbonyl group {Ci-Cg) alkyl (Ci-Ce)tphenylcarbonyl group or benzyl group); {cl4) an aryl group each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Cg), alkoxy group (Ci-Ce), cycloalkyl group (C3-Cg), haloalkyl group (Ci-Ce), haloalkoxy group (Cl-Cg), halocycloalkyl group (Cj-Ce), alkylthio group (Ci-Cg), alkylsulfinyl group (Ci-Cg), alkylsulfonyl group (Ci-Cg), haloalkylthio group (Ci-C6; , haloalkylsulfinyl group (Cl-Cg), haloalkylsulfonyl group (Ci-Ce), Ra(Rb)N group (where Ra and Rb are the same as the above), alkoxycarbonyl group (Ci-Ce), and group Ra(Rb) Ncarbonyl (where Ray Rbson are the same as above); (cl5) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring; (cl6) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (Cl-Cg), cycloalkyl group (Ca-Cd), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Cg), halocycloalkyl group (C3-Cg), alkylthio group (Ci-C6), alkylsulfinyl group (C1-C0), alkylsulfonyl group (Ci-C6), IF-2020-86290883-APN-ANP#INPI Page 11 of 122 haloalkylthio group (Ci-Ce), haloalkylsulfinyl group (Cj-CsJ , haloalkylsulfonyl group (Ci—Cs) < group Ra(Eb)N (where Ray Rbson are the same as the above) , alkylthio group (Ci-Cs) alkyl (Cj-Ce) , phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl group (Ci-Ce) and Rd(Rb) Ncarbonyl group (where Rdy Rbson are the same as the above); (C19) an alkyl group (Ci-Ce) of a 5- to 6-membered hetero ring or fused hetero ring of 8 to 10 members; (c20) a 5- to 6-membered hetero ring alkyl group or 8- to 10-membered fused hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-C6), alkoxy group (Ci-C6), cycloalkyl group (C3-C&), haloalkyl group (Ci-Ce), haloalkoxy group (CiCe), halocycloalkyl group (Ca-Cg), alkylthio group (CiC6), alkylsulfinyl group (CL-Cg), alkylsulfor group.yl (Ci-Cs), haloalkylthio group (Ci-Cs), haloalkylsulfinyl group (Ci-Cg), haloalkylsulfonyl group (Ci-Ce), Ra(Rb)N group (where Ra and Rb are the same as the previous ones), alkylthio group (Ci-Ce), alkyl (Ci-Cg), phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl group (Ci-C6), and Rñ(Rb)Ncarbonyl group (where Ra and Rb are the same as the previous ones); or (c21) an alkyl group (Ci-Cg) each independently having in the chain 1 to 3 substituents selected from the group consisting of a cyano group, alkoxy group (Ci-Cg), Ra(Rb)N group (where Rfiy Rbson are the same as the above), alkylthio group (Ci-Sg), alkylsulfinyl group (Ci-C6) and alkylsulfonyl group (CjC6). IF-2020-86290883-APN-ANP#INPI Page 12 of 122 [4] A fungicide characterized in that it contains as an active principle the compound according to any one of points [1] to [3] above or salts thereof, [5] A method for controlling plant disease characterized by the treatment of a plant or soil with an effective amount of fungicide according to point [4] above, [6] Use of the compound in accordance with any one of the points [1] to [3] above or salts thereof as a fungicide. [Effect of the invention]

[0007] The compound of the present invention or salts thereof has a notable effect as an agro-horticultural fungicide. [Ways to carry out the invention]

[0008] In the definition in the general formula (I) of the compound of the present invention, halo indicates a halogen atom, which represents a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom;

[0009] Alkyl group (C;-Cs) indicates a linear or branched alkyl group on the carbon atom number 16, such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, tertiary butyl group, pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2 IF-2020-86290883-APN-ANP#INPI Page 13 of 122 methylpentyl, 3-methylper-yl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group or similar;

[0010] The alkenyl group (C2-C9) indicates a linear or branched alkenyl group of the 2-8 carbon atom, such as, for example, a vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, beptenyl group, octenyl group, or the like; the alkynyl group (C2-C8) indicates a linear or branched alkynyl group of the 2-8 carbon atom, such as, for example, an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl group 1-1-propynyl, 2-methyl-3-propynyl group, pentinyl group, 1-hexynyl group, 3-methyl-l-butynyl group, 3,3-dimethyl-l-butynyl group or similar.

[0011] Cycloalkyl group (Cj-Cs) indicates a cyclic alkyl group of carbon atom number 3-6 such as, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group or the like; alkoxy group (Ci-Cs) includes a linear or branched chain alkoxy group of carbon atom number 16 such as, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyloxy group or the like; IF-2020-86290883-APN-ANP#INPI Page 14 of 122 [0012 j Alkylthium group (Ci-Ce) indicates a linear or branched chain alkylthium group of carbon atom number 1-6 such as, for example, a methylthium group, ethylthium group, normal propylthium group, isopropylthium group, normal butylthium group, secondary butylthium group, tertiary butylthium group, normal pentylthium group, isopentylthium group, tertiary pentylthium group, neopentylthium group, 2,3-dimethylpropylthium group, 1-ethylpropylthium group, 1-meoylbutylthium group, normal hexylthium group, isohexylthium group, 1,1,2-trimethylpropylthium group or the like;

[0013] Alkylsulfinyl group (ICi—Ce) indicates a linear or branched chain alkylsulfinyl group on carbon atom number 1-6 such as, for example, a methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, iso-propylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, iso-pentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso-hexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, or the like;

[0014] Alkylsulfonyl group (Ci-C6) indicates a linear or branched alkylsulfonyl group on carbon atom number 1-6, such as, for example, a methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, or a secondary butylsulfonyl group. IF-2020-86290883-APN-ANP#INPI Page 15 of 122 tertiary butyl sulfonyl group, normal pentyl sulfonyl group, iso-pentyl sulfonyl group, tertiary pentyl sulfonyl group, neopentyl sulfonyl group, 2,3-dimethylpropyl sulfonyl group, 1-ethylpropyl sulfonyl group, 1-methylbutyl sulfonyl group, normal hexyl sulfonyl group, iso-hexyl group sulfonyl, 1,1,2trimethylpropyl sulfonyl group or the like.

[0015] Alkylcarbonyl group (Ci-Ce) indicates an alkylcarbonyl group on carbon atom number 2-7, such as those having an alkyl group (Ci-Cs) described above or similar, such as, for example, an acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, pivaloyl group, hexanoyl group, ci-clopropylcarbonyl group, or similar. [00161 The alkoxycarbonyl group (Ci-Ce) indicates an alkoxycarbonyl group on carbon atom number 2-7, such as those having the alkoxy (Ci-C$) groups described above or similar, such as, for example, a methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, tertiary butoxycarbonyl group, pentyloxycarbonyl group or similar.

[0017] The groups mentioned above as alkyl group (Ci-Cc), alkenyl group (C2-C5), alkynyl group (C2-C6), cycloalkyl group (C3-Ce), alkoxy group (Ci-Cs) or alkyltic group (Ci-Ce), alkylsulfinyl group (Ci-Cs) or alkylsulfonyl group (Ci-Gc) or similar, may be replaced with one or two or more IF-2020-86290883-APN-ANP#INPI Page 16 of 122 halogen atoms in substitutable positions and if these groups are substituted with two or more halogen atoms, the halogen atoms may be the same or different. Such groups substituted with halogen atoms are each designated as a haloalkyl group (C1-C2), haloalkenyl group (C2-C6), haloalkynyl group (C2-C6), halocycloalkyl group (C3-C6), haloalkoxy group (C1-C6), haloalkylthio group (C1-C6), haloalkylsulfinyl group (C1-C6), or a haloalkylsulfonyl group (C1-C6).

[0018] Expressions such as (Ci-Cg), (C2-Cs), or {O3— or similar ones define a range of the number of carbon atoms in each substituent. Furthermore, the definition mentioned above also applies to a group to which the aforementioned substituent bonds are attached; for example, in the case of an alkoxy (Ci-Ce) alkyl (Ci-Ce) group, it indicates that a linear or branched alkoxy group with carbon number 1-6 is bonded to a linear or branched alkyl group with carbon number 1-6.

[0019] aryl group and aryl indicate an aromatic hydrocarbon group of carbon number 6-10, such as, for example, a phenyl group, a naphthyl group, or the like.

[0020] A hetero ring of 5 to 6 members indicates, for example, the following structures. The dot · indicates a bonding position. [Chemical formula 4] IF-2020-86290883-APN-ANP#INPI ]7 Page 17 of 122

[0021] An 8- to 10-membered heterofusion ring indicates, for example, the following structure. The dot (·) indicates a junction position. [Chemical formula 5] IF-2020-86290883-APN-ANP#INPI Page 18 of 122

[0022] As salts of the compound of the present invention represented by the general formula (I), for example, inorganic salts such as hydrochloride, sulfate, nitrate, phosphate or the like, organic salts such as acetate, fumarate, malate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate or the like, and IF-2020-86290883-APN-ANP#INPI 1.9 Page 19 of 122 salts with organic or inorganic bases such as sodium ion, potassium ion, calcium ion, trimethyl ammonium or similar.

[0023] In some cases, the compound of the present invention represented by general formula (I) and its salt have one or more centers of asymmetry in the structural formula and there are two or more enantiomers and diastereomers; the present invention includes all enantiomers and mixtures in which they are present in any proportion. Furthermore, the compound of the present invention represented by general formula (I) and a salt thereof in some cases have two stereo isomers as a result of the carbon-carbon or carbon-nitrogen double bond in the structural formula; the present invention includes all stereo isomers and mixtures in which they are present in any proportion.

[0024] For the compound of the present invention represented by the general formula (I), the preferred embodiments are listed as follows. As A, a single link or the structure mentioned above A1; A2; A5; A6 or A'·1 is preferred. As B, a single link or C(RL) (R2) is preferred. As Y, a single bond; an oxygen atom or N (R3) is preferred. As R1 and R2 each independently (to) a hydrogen atom; (a2) a halogen atom; or (a4) an alkoxy group (Cl-Có) is preferred, and (a1) a hydrogen atom; or (a4) an alkoxy group (Ci-Cs) is more preferred. IF-2020-86290883-APN-ANP#INPI Page 20 of 122 As R3(bl) a hydrogen atom; (b2> an alkyl group (Ci-Ce); (b3) an alkoxy group (Ci-C$); (b4) a cycloalkyl group (Cj-Cg); (b7) an alkenyl group (C2-C6) ; (b8) an alkynyl group (C2—Ce) ; or (b9) a cycloalkyl (C3-C5) alkyl group (C1-Cd is preferred, (bl) a hydrogen atom; (b2> an alkyl group (Ci-C$) ; or (b3) an alkoxy group (Cl-Cs) is more preferred. Like Q, (the) hydrogen atom; (c2) an iCi-Ce alkyl group); (c5) a cycloalkyl group (Cs-Cg); (c6) an alkoxy group (Ci-Cg); (c7) a haloalkyl group (Ci-Ce); (cl2) group Ra(Rb)N (where Ra and Rb each independently indicate a hydrogen atom, alkyl group (Ci-Ce), alkenyl group (Cz-Cg), alkynyl group (Cz-Ce), cycloalkyl group (C3-C6), alkoxy group (Ci-Ce), haloalkyl group (Cj-Cg), cycloalkyl group (C3-C6) alkyl (Ci-Cg), phenyl group, alkoxy group (Cl-Cg) alkyl (Ci-Cs), dialkoxy group (Ci-Cg) alkyl (Ci-Cg), cyanoalkyl group (Ci-Cg), alkylthio group (Ci-C&) alkyl (Ci-C$), dialkylamino group (Cl-Cg) alkyl (Ci— Cg), alkylcarbonyl group (Ci-Cs), alkoxycarbonyl group (Cj-Ce) alkyl (Ci-C$), phenylcarbonyl group or benzyl group); (cl4) an ring group having each independently on the ring 1 to 8 substituents selected from the group consisting of an atom of IF-2020-86290883-APN-ANP#INPI Page 21 of 122 halogen, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (Ci-Cs), cycloalkyl group (Ci-Ct), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Ce), halocycloalkyl group (C3-Cs), alkylthio group (Ci-Ce), alkylsulfinyl group (Ci-Ce), alkylsulfonyl group (Ci-Ce), haloalkylthio group (Ci-Cs), haloalkylsulfinyl group (Ci-Cs), haloalkylsulfonyl group (Ci-Ce), Ra{R'°)N group (where Ray Rbson are the same as the previous ones), alkoxycarbonyl group (Ci-Ce) and Rñ(Rb) Ncarbonyl group (where Ray Rbson are the same as the previous ones); (cl5) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring; (cl6) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring each independently having 1 to 3 substituents on the ring. Selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (Ci-Cg), cycloalkyl group (C3-C6), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Cg), halocycloalkyl group (C3-C6), alkylthio group (Ci-Ce), alkylsulfinyl group (Ci-Ce), alkylsulfonyl group (Ci-Ce), haloalkylthio group (Ci-Ce), haloalkylsulfinyl group (Ci-Ce), haloalkylsulfonyl group (Ci-Cg), Ra(Rb)N group (where Ra and Rb are the same as the previous) , alkylthio (Ci-Ce) group alkyl (Ci-Ce) , phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl (Ci-Ce) group and R° (Rb) Ncarbonyl group (where r and Rb are the same as the previous ones); (cl9) an alkyl group (Ci-Cs) of a 5- to 6-membered hetero ring or fused hetero ring of 8 to 10 members; (c20) an alkyl group {Ci-Cg) of a 5- to 6-membered hetero ring or a fused 8- to 10-membered hetero ring IF-2020-86290883-APN-ANP#INPI Page 22 of 122 having each independently on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Cg), alkoxy group (Cl-Cg), cycloalkyl group (Cj-Ce), haloalkyl group (Ci-Ce), haloalkoxy group (CiC&), halocycloalkyl group (Cj-Cg), alkylthio group (ClCg), alkylsulfinyl group (Ci-Cs), alkylisulfonyl group (Ci-Cg), haloalkylthio group (Ci-Cs), haloalkylsulfinyl group <Cs-Cs), grupo haloalquilsulfonilo (Ci-Ce) , grupo Rs(Rb)N (en donde Ray Rbson los mismos que los anteriores), grupo alquiltio (Ci-Ce) alquilo (Ci-C$), grupo fenilo, grupo fenoxi sustituido con halógeno, grupo alcoxicarbonilo (Ci-Cs) y grupo Ra(Rb) Ncarbonilo (en donde Ray Rbson los mismos que los anteriores); (c21) an alkyl group (Ci-Cg) each independently having in the chain 1 to 3 substituents selected from the group consisting of a cyano group, alkoxy group (Ci-Ce), Ra(Rb)N group (where Ra and Rb are the same as the above), alkylthio group (Ci-Ce), alkylsulfinyl group (Ci-Cs), and alkylsulfonyl group (CiC6); (c22) group RcON=C(Rd)MH (where Rcy Rd each independently indicates a hydrogen atom or alkyl group (Ci-Cs)) or (c23) group 3-ethoxyiminoazetidin-l-yl is preferred, and (el) a hydrogen atom; (c2) an alkyl group (Ci-Ce) ; (c5) a cycloalkyl group (Cj-Cs); (c6) an alkoxy group (Ci-Cg); (c7) a haloalkyl group (Ci-Ce) ; (cl2) a group Rs(Rb)N (where Ray Rb each independently indicates a hydrogen atom, group IF-2020-86290883-APN-ANP#INPI Page 23 of 122 alkyl (Ci-Cg), alkenyl group (Ci-Ce) alkynyl group (C2-Ce) cycloalkyl group (C3-Ce) alkoxy group (Ci-Ce) , haloalkyl group (Ci-Cs), cycloalkyl group (Ci-Ce) alkyl (Ci-Ce), phenyl group, alkoxy group (Ci-Ce) alkyl (Ci-Cg) , dialkoxy group (Ci-Cg) alkyl (Ci-Cs) , cyanoalkyl group (Ci-Ce) alkylthio group (Ci-Cs) alkyl (Ci-Cd), dialkylamino group (Ci-Cs) alkyl (Ci-Ce) , alkylcarbonyl group (Ci-Ce), alkoxycarbonyl group (Ci-Ce) alkyl (Ci-Ce), group phenylcarbonyl or benzyl group); (cl4) an aryl group each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (Cx—Cg), cycloalkyl group (C3-C6), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Ce), halocycloalkyl group (C3-C5), alkylthio group (Cj-Ce), alkylsulfinyl group (Ci-C$), alkylsulfonyl group (Ci-Cg), haloalkylthio group (Ci-Cs), haloalkylsulfir.yl group (Ci-Cs), halocalkylsulfonyl group (Ci-C$), Ra(Rb)N group (where Ra and Rb are the same as the above), alkoxycarbonyl group (Ci-Ce) and Ra(Rb) Ncarbonyl group (where Ray Rbson are the same as the previous ones); (cl5) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring; (cl6) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Cs), alkoxy group (Ci-Ce), cycloalkyl group (C3-C5), haloalkyl group (Ci-Cg), haloalkoxy group (Ci-Cs), halocycloalkyl group (Cs-Cg), alkylthio group (Cl-Cg), group IF-2020-86290883-APN-ANP#INPI Page 24 of 122 alkylsulfinyl {Ci-Cg) , alkylsulfonyl group (Ci-Ce), haloalkylthio group (Ci-Cg), haloalkylsulfinyl group (Ci-Ce)t haloalkylsulfonyl group (Ci-Cg), Rd(Rb)N group (where Ray Rbson are the same as the previous ones) , alkylthio group (Ci-Cg) alkyl (Ci-Cg) , phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl group (Ci-Cg) and R* (Rb) Ncarbonyl group (where Ray Rbson are the same as the previous ones); {cl9) an alkyl group (Ci-Cg) of a 5- to 6-membered hetero ring or fused hetero ring of 8 to 10 members; (c20) a 5- to 6-membered hetero ring alkyl group or 8- to 10-membered fused hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl group (Ci-Ce), alkoxy group (Ci-Cg), cycloalkyl group (C3-Cg), haloalkyl group (Ci-Ce), haloalkoxy group (Ci-Cg), halocycloalkyl group (C3-Cg), alkylthio group (Ci-Cg), alkylsulfinyl group (Ci-Cg), alkylsulfonyl group (Ci-Ce), haloalkylthio group (Ci-Ce), haloalkylsulfinyl group (Ci-Ce), haloalkylsulfonyl group (Ci-Cg), group Rd(Rb)N (where Ray Rbson are the same as the previous ones), alkylthio (Ci-Ce) group, alkyl (Ci-Cg)t group, phenyl group, halogen-substituted phenoxy group, alkoxycarbonyl (Ci-Cg) group, and Ra(Rb) Ncarbonyl group (where Ray Rbson are the same as the previous ones);or (c21> an alkyl group (Ci-Ce) each independently having in the chain 1 to 3 substituents selected from the group consisting of a cyano group, alkoxy group (Ci-Cs) , R*{Rb)N group {where Rdy Rbson are the same as the above), alkylthio group (Ci-Cg)t, alkylsulfinyl group (Ci-Ce) and alkylsulfonyl group (CiIF-2020-86290883-APN-ANP#INPI; Page 25 of 122 Ce) is more preferable. As R5, (di) a hydrogen atom; (d2) an alkyl group (Cl-Có) ; or (d5) a benzyl group is preferred. As X1, X2, X3, and X\ (fl) a hydrogen atom is preferred. Among the compounds of the present invention or salts thereof, those with low HDAC4 inhibitory activity are preferred. Because EDAC4 exhibits multiple actions, its inhibitors are expected to be used as anticancer agents or similar. However, due to these multiple actions, possible non-selective or excessive inhibition may lead to various toxicities, such as teratogenicity, as described in the literature (Haberland M. et al., Nat. Rev. Genet., 2009, 10, 32-42 and Erminio G. et al., Current Pharmaceutical Design, 2014, Vol. 20, No. 00).

[0025] The compounds of the present invention can be produced by the following production methods, for example, but the production methods of the compounds of the present invention are not limited to them.

[0026] Production Method 1 (Chemical Formula 6) IF-2020-86290883-APN-ANP#INPI Page 26 of 122 (1) (H) (1-2) (In the formula above, A, B, Q, R5, X-, X2, X3, X4 and Y have the same meaning as before, and L indicates a leaving group such as a halogen atom, mesyl group, tosyl group, or triflate group.) (0027) The compounds represented by the general formulas (Ii) and (T-2) of the present invention can be produced by the above, following steps [a] and [b], but the present inventive compounds and a method of producing them are not limited to them. Step [a]: A step to produce a compound for the general formula (1-1) by reducing a compound represented by the general formula (1). Step [b]: A step to produce a compound represented by the general formula (1-2) by reacting a compound represented by the general formula (I-1) with a compound represented by the general formula (2).

[0028] Production method in step [a] The compound represented by the general formula (I IF-2020-86290883-APN-ANP#INPI Page 27 of 122 1) can be produced by reacting the compound represented by the general formula (1) with a reducing agent in an inert solvent; the compound represented by the general formula (1) can be produced by the methods described in WO 2017 / 213252, WO 2017 / 055473, WO 2015 / 185485, WO 2017 / 118689, WO 2017 / 080859, WO 2013 / 008162, WO 2017 / 076935, WO 2015 / 185485 and JF 63-162680A.

[0029] Examples of the reducing agent that may be used in the reaction include lithium aluminum hydride, sodium aluminum hydride, sodium borohydride, sodium cyanoborohydride, or similar substances; the amount to be used may generally be selected from the range of, generally, 0.25 times the mol to 2 times the mol with respect to the compound represented by the general formula (1).

[0030] Any solvent that does not significantly inhibit the progress of this reaction may be used as the inert solvent; these include, for example, aliphatic hydrocarbons such as pentane, hexane, and cyclohexane or similar compounds; ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, and dioxane or similar compounds; and alcohols such as methanol, ethanol, 1-propanol, 2-propanol, or similar compounds. These inert solvents may be used alone or in a mixture of two or more. The amount to be used can generally be selected from the range of 0.1 to 100 L with respect to 1 mole of the compound represented by the general formula. IF-2020-86290883-APN-ANP#INPI Page 28 of 122

[0031] Since the reaction is equimolar, equimolar amounts of each reactant can be used, and any reactant can be used in excess. The reaction temperature can generally range from room temperature to the boiling point range of the inert solvent used, and the reaction time, which varies depending on the reaction scale and temperature, can generally range from several minutes to 48 hours. Once the reaction is complete, the target product can be isolated from the reaction system using ordinary methods, and the target product can be produced by purification through recrystallization, column chromatography, or similar means, as required.

[0032] Production method in step [b] The compound represented by the general formula (I2) can be produced by reacting the compound represented by the general formula (I—1) and the compound represented by the general formula (2) in an inert solvent in the presence of a base.

[0033] Examples of bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, potassium bicarbonate, or similar compounds; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; and tertiary amines such as triethylamine and diisopropylethylamine. IF-2020-86290883-APN-ANP#INPI Page 29 of 122 1,8-diazabicyclo[5.4.0]undec-7-ene; nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine or the like. The amount to be used is relative to the compound represented by the general formula (I—1) and can generally be selected from the range of 1 mol to 5 mol.

[0034] The inert solvent used in this reaction can be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, or the like; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar aprotic solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in a mixture of two or more.The amount of the same to be used can generally be selected from the range of 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (II).

[0035] Since the reaction is equimolar, equimolar amounts of each reactant can be used, and any reactant can be used in excess. The reaction temperature can generally be from the temperature IF-2020-86290883-APN-ANP#INPI Page 30 of 122. The reaction time, which varies depending on the reaction scale and temperature, can generally range from several minutes to 48 hours. Once the reaction is complete, the target product can be isolated from the reaction system containing the target product by an ordinary method, and the target product can be produced by purification by recrystallization, column chromatography, or similar methods, when necessary. (0036] Production Method 2 [Chemical Formula 7] (3) (1-3) (where A, 5, Q, Re, X1, X2, X3, X4e Y have the same meaning as above, and M indicates a metallic substituent such as Li, MgCl, MgBr and Mgl)

[0037] The compound represented by the general formula (I3) can be produced by the following step (c]. Step [c] A step for producing a compound represented by the general formula (1-3) by reacting a compound represented by the general formula (3) and a compound represented by the general formula (4).

[0038] Production method in step [c] A compound represented by the general formula (I3) can be produced by reacting a compound IF-2020-86290883-APN-ANP#INPI Page 31 of 122 represented by the general formula (3) and a compound represented by the general formula (4) in an inert solvent.

[0039] Any solvent that does not significantly inhibit the progress of this reaction may be used as the inert solvent. Examples include linear or cyclic aliphatic hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; and linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, dioxane, and tetrahydrofuran. These inert solvents may be used alone or in a mixture of two or more. The amount of solvent used can generally be selected from the range of 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (3).

[0040] Since the reaction is equimolar, equimolar amounts of each reactant can be used, and any reactant can be used in excess. The reaction temperature can generally be from 0°C to the boiling point range of the inert solvent used, and the reaction time, which varies depending on the reaction scale and temperature, can generally range from several minutes to 48 hours. Once the reaction is complete, the target product can be isolated from the reaction system using ordinary methods, and the target product can be produced by purification through recrystallization, column chromatography, or similar means, as required.

[0041] IF-2020-86290883-APN-ANP#INPI Page 32 of 122 Representative examples of the compounds represented by the general formula (I) of the present invention are illustrated below in Tables 1 to 3, but the present invention is not limited to them. In the Tables, Me” indicates a methyl group, Et indicates an ethyl group, n-Pr indicates an n-propyl group, i-Pr indicates an isopropyl group, n-Bu indicates an n-butyl group, i-Bu” indicates an isobutyl group, secBu indicates a secondary butyl group, t-Bu indicates a tertiary butyl group, Ph indicates a phenyl group, cyc-Pr indicates a cyclopropyl group, and cyc-Hex” indicates a cyclohexyl group. Physical properties indicate a melting point (°C), refractive index nD (measurement temperature), or NMR; NMR data are shown in Table 14.

[0042] [Chemical formula 8] (1-4) IF-2020-86290883-APN-ANP#INPI Page 33 of 122

[0043] [Table 1] Table 1(1) Compound No. QAR' R2 RJ R6 Physical Property 1-1 Me o, HH Mo M Π 160-151 1-2 Me O2 R 51 OMe EH 1-3 He Oi OMe HHHH 1-4 Me o <s>\ HE Me tl Me 1-5 H - HE Me HH 128-129 i-6 H - KH CHe HH 1-7 H - OMe BHHB 1-0 H - EH Me II Me 1-5 n-Pr 0 EH Me EH 114-115 1-10 n-?r 0 BH 1 20-13 E-HH n-Pr 0 OMe HHBH 166-167 1-12 n-Pr o HH Me H Me 161-163 1-13 Me o, H II Me Me H 107-109 1-14 Me \ / ,J It H Me CHjFt B 1.3731 {25.11 IF-2020-86290883-APN-ANP#INPI Page 34 of 122 (0044] [ Table 2 Table 1(2) Compound NO. QAR· RJ R' R* R' Property iisica 1-15 i-Pr 0? / s\ H IÍ Me EH 123-124 1-16 i-Pr O2 li H CKc HH 1-17 i-Pr Ο (Λ \ OMe HHH a 1-18 i-Pr .. / O iz; \ HK Me H Me 1-19 NMft; O, II Me ^S\ Me 1-10-201-HE NM©2 0, HH Otte HH 1-21 KMei .. / O t / i \ 0MC II KH a 1-22 NMej a / Ο < / J \ II K Me 1: Ke 1-23 nA . II y—· NS^ H H Me (1 H 1.3332-26.4) 1-24 \ 7 Z=Z 0 a H OMe M a 1-25 nA, . II 7—* o CMC H H E H 1-26 V.-V» i·: H Me H He IF-2020-86290883-APN-ANP#INPI Page35 of 122

[0045] [ Table 3 Table 1(3) corcpuesThe NO. Q a VR* Rb R* Physical property 1-27 NH't-Bu> 0 3 3 Ke H :-i 15C-151 1-28 NIUt-Bu) 0 H .4 OMe M 3 13C-132 1-29 NKU-BJ) 0 ot'e >1 1 li II-3 NEH-3) H Me 1-31 o HH Me KH 196-197 1-32 ¿= o HE OMe |{ II 1-33 o CKO HH Π II 1-34 py o HH Me Me H 1-35 Ν-λ \=N o HK Me KH 1.3732(21.6? 1-3? \ N o I': II o I' 1-37 \=N 0 CMe li H li H 1-38 \=NHE Me Ke H IF-2020-86290883-APN-ANP#INPI Page 36 of 122

[0046] [ Table 4 Table 1<4) Compound no. QA R' Ft* R* R5 R« Physical property 1-39 cyc-Pr 0 8 H Me 11 1! 144-145 1-40 cyc-Fr 0 HH CMe HH 118-122 1-41 cyc-Pr () OKe H II 11 a 1-42 cyc-Pr o JI II Me Ke H 1-43 cyc-hex o H li Me HH 136-1-43 1-43 cyc-hex II e H-HE 1-45 cyc-hex 0 CMC H JI HE 1-46 cyc-hex 0 HH Ke Me H 1-47 i-Pr 0 H JI we HH 182-185 1-48 i-Pr o il II OMe MH 1-49 i-Pr o CMe EHH II i Me- 50- Me- HEH IF-2020-86290883-APN-ANP#INPI Page 37 of 122

[0047] [Table 5] Table 1{5) Compound No. 0 to R R2 RJ Rs R6 Physical Property 1-51 Cl () 3 E MS HH 1.3780(21.4) 1-52 0 HH Me 3 3 179-181 1-53 CF5 <Tt-* 0 E H Ke rl H 1.3508 ¡21.4) 1-54 F F 0 E 3 KC H 3 195-196 1-55 o rl H Me E 3 1.3756(21.4) 1-56 F O rl H Me E H 128-129 1-57 NH(Et) 0 H IÍ Me H E 173-174 1-58 au(Et) 0 H E OKC H K 153-155 1-59 XH(Et) 0 cue H H H E 1-60 KH(Et) H H Ke Me 3 1-61 NH{cyc-hex) 0 H H Ke 3 3 156-157 1-62 NII (Ph) E 3 Ke 3 3 179-100 IF-2020-86290883-APN-ANP#INPI Page 38 of 122

[0048] [Table 6] Table 1(6) Compound no. 0 AR; IV e Propiedso fis.ca 1-63 NH(Et) s HH Me H II 160-161 1-64 NIUFhl s EK Me HH 197-200 1-65 NMe* ¢) EH Me HE 97-99 1-66 NMOz 0 HH CKe HH 160 HH OH-30 HH 1-68 NHC, o HH Me Ke 11 1-69 NECz o HE Me KK 1.3471(25.1) 1-70 NE-2 o EE OKe HE 1-71 NEtj OMe HHHE 1-72 XEt: 0 HH Me Me H 1-73 0 N— 1 H- 17 H- 17 H-17 CH;C1 .. / 0 «Λ \ HH Me HH 161-162 IF-2020-86290883-APN-ANP#INPI Page 39 of 122 (0049] [ Table 7 Table 1(7} Cornpuesto Xo. 0 A R- R* R' R' Rh Physical property 1-75 0, HH Ke HH 161-162 1-76 Et o, H h* Me HE 114-115 1-77 Et o. HH OMe HH 1-78 EL o, zs; OMe HHEH 1-79 Et O2 HH Me Me H 1-90 r.-Pr °2 HH Me HH 142-143 1-01 n-Du o> HH Ke HH 147-148 1-82 CH?CH:OCH-> - / O 1' H Me HH 154- 15 15 Me HH 154- II EH 1-8 EH\ 1-84 i-?r 0 HH Et HH 100-102 1-85 NHll-Bu) o HH Et EH 1-86 HE!Kei H ne HH IF-2020-86290883-APN-ANP#INPI Page 40 of 122

[0050] [ Table 8 Table 1(8) Compound Xc. Q Λ Ri iV IP R5 Rs Property lisica 1*87 Nii-Mel 0 HH Ole MH 205-203 1-88 0 1- II owe 11 •1 1-09 HN / -oi·: H Ole HH 195-200 1-90 (>le O\HH 15-66 1-91 Et 0 HH 11 HH 1-92 r.-Fr 0 i·: H II II :-i 192-193 1-93 cyc-Pr o HHHHH 223-225 1-94 NH(C-BU) 0 HH II 11 H 197-199 HH 18 HH-HH° 254-2S8 1-96 F3cT 0 It II II 11 1 235-238 1-97 -o 0 HHH 9 H 113-115 1-98 NEC EHHHH 159-16-? IF-2020-86290883-APN-ANP#INPI Page 41 of 122

[0051] [ Table 9 Table 1(9) Compound no. QAR* R- R* Rs R* Physical property 1-99 Me 0 .HH = / HH 1 -1 CO Et 0 II R (— 1 _ / HH 1-101 NH(t-Bu) 0 HH — / HH 1-102 Ke O2 HH r* =.1 HH 1-103 Ke 0-104 Ke HEH 1-104 —· H li 1-105 He 0 KEHH 1-106 F ¡y 0 EHHH 191-192 1-107 b 0 E a HE 1-108 b X«le EHEE 113-116 1-109 0 2Me li HHH 183-183 130 CHE If HHC 194–195 IF-2020-86290883-APN-ANP#INPI Page 42 of 122 [Table 10] Table 1(10) compound NO. 0 R* R2 R3 Rs 3s Physical Property 1-111 CH-CCHi 0 Z>MO HH 3 H 118-119 1-112 CH / CCHs 0 li >1 JI H II 1-113 Cit-BU) 0 1' 3 H 3 K 34 Me 183,1-1 1-115 n-Pr 0 Me 3 K 3 3 1-116 NH(Et) 0 Me 3 K 3 3 1-117 cyc-Pr Me 3 H 3 3

[0052] [Chemical Formula 9] IF-2020-86290883-APN-ANP#INPI Page 43 of 122

[0053] [Table 11] Table 2(1) Compound Ko. QA Physical property 2-1 1 0 188-189 2-2 °^Ί 0 •<^· 212-214 2-3 0 220-221 2-4 H 0 226-228 2-5 H f3c^n^ 0 250X·6'HNO 2-6 196-198 2-7 H EtO^^'N'^ 0 2-8 H MeChC^N^ 0 218-219 2-9 H EtO2C^Nx> 0 2-10 II 0 255-25? 2–11 H 209–210 IF-2020-86290883-APN-ANP#INPI Page 44 of 122

[0054] [Table 12] Table 2(2) Compound No. Q k Physical Property 2-12 1 F2nC^N^ 0 1.3234(24.6) 2-13 o 160-162 2-14 o 227-228 2-15 II () 214-215 2-16 H o 224-225 2-17 Λ H 0 257-259 2-16 0 152-153 2-19 Λα, - RMS 2-20 A 0 246-246 2-21 H -X s 97-09 2-22 II IF-2020-86290883-APN-ANP#INPI Page 45 of 122

[0055] [Table 13] Table 2(3} Compound NO. Q Properity Lysic 2-23 zx J 1 0 2-24 H 0 2b6-2b8 -25 1 1 Λ 0 1.3851(22.4) 2-2.6 1 0 176-178 2-2? >) 0 207-2CS 2-28 H 0 248-249 2-29 II 0 258-261 2-3C 0 - 2-31 9. 0 - 2-32 1 0^2^. 1 1 ! Z^Z ' Vo * - 2-33 II NC^,N^ IF-2020-86290883-APN-ANP#INPI Page 46 of 122

[0056] [Chemical formula 10]

[0057] [Table 14] Table 3(1) Compound No. 2 Physical Property 3-1 133-134 3-2 186-187 3-3 181-183 3-4 Ti n 128-130 3-5 Cl 212-214 3-6 A? u ce 241-243 IF-2020-86290883-APN-ANP#INPI Page 47 of 122 3-7 190-191 3-8 ο. Γ** 171-172 of Article 3(2) of Body NO. Q Physical property 3-9 Qx f* 1.3459^25.4} 3-10 y< yJ 187-109 3-11 ΟΛ yN A ' / f / 1.3576(25.4) 3-12 Qx O^r 139-Γ·3^γ 13 243–250 IF-2020-86290883-APN-ANP#INPI Page 48 of 122 3-14 Ch 270-272 3-15 γΓ A * 5 yN nn 261-263 [0059J [Table 16] Table 3(3) Compound Ko. Q Physical property 3-16 cr\ uz 252-253 3-17 N'\ IL / > 154-156 3-18 Q 204-206 3-15 o °τί^ / I o 90-92 3-20 N-\* no2 167-168 IF-2020 86290883-APN-ANP#INPI Page49 of 122

[0060] [Table 17] Table 3(4) Corr,position NO. Q Physical property 3-22 N \ Cl 127-12Ü 3-23 A 127-128 3-24 / ΝΑ* ίγΟ 0 204-2C5 3-25 c— o:=\ Y=zl λ 209-21 o 1'C \7' 3-2 IF-2020-86290883-APN-ANP#INPI Page 50 of 122

[0061] [Table 18] Table 3(5) Compound No. Q Physical Property 3-28 N\_ II 4>-Br b<n 172-173 3-29 i £ / > 0 141-142 3-30 —o / =oz=\ 185-187 3-31 o / sz L 191-193 3-32 Cl 20B-210 IF-2020-86290883-APN-ANP#INPI Page 51 of 122

[0062] [Table 19] Table 3(6} Ko compound. <? Propiedad física 3-34 νΓ V Cl 247-248 3-35 t δ 178-LCO 3-36 M Br 220-221 3-37 M 222-223 3-38 157-150 3-39 233-235 IF-2020-86290883-APN-ANP#INPI Page 52 of 122

[0063] [Table 20] Table 3(7} Compound NO. Q Physical property 3-40 uc Z<»C o' k 225-226 3-41 2C5-207 3-42 A 208-210 3-43 % 142-144 3-44 V Λ / Λ 7\ o 136-13? 3-45 °rT 3-46 (λ 3-47 (1 r* / Nx

[0064] IF-2020-86290883-APN-ANP#INPI Page 53 of 122 [Table 21] Table 3(8) Compound NO. 0 Physical property 3–48 ΟΛ 3–49 ο. f~* VN' ci / 3-5C Vn^ 3-51 Ox r* VK / 0 3-52 II ,N NNO, BMK 3-53 rTN^* II ,NN·^ Cl 160-161 3-54 N'XC IL# _ Xo H 3-55 / c- / =z

[0065] IF-2020-86290883-APN-ANP#INPI Page 54 of 122 [Table 22] Table 3(9) Compound no. 0 Physical property 3-56 N'\ X HN b^ 3-57 o · 3-58 ^Z^Z z=^ z^ / 3-59 N'\* li / / N < / 260-262 3-60 dT H 3-61 d^* / k / "'o 11 3-62 127-129

[0066] IF-2020-86290883-APN-ANP#INPI Page 55 of 122 [Table 23] Table 3(10) longpoint NO. Q Pxcpicdétíi physics 3-63 Ν'Γ* iV 1ÜÜ-181 3-64 N'NC 11 / ) N'N 204-205 3-nT* II .NN·^ 154-156 3-66 n ,NZ-6'N T 14 211-212 3-68 204-236 3-69 °rf 218-22C 3-7C z=\-=7 199-2C1

[0067] [Table 24] Table 3(11) IF-2020-86290883-APN-ANP#INPI Page 56 of 122 Compound No. Q Physical Property 3-71 185-186 3-72 xP or 3-73 0CN Cl 230-231 3-74 yT 195-201 3-75 Brxvi <Xr^N^* XX? 227-228 3-76 N-\* o Br~^ 233-232 3-77 N-X* ΛΐΝ o 229-230 3-73 \ ΊΓ Λ’ yA-N 262-263

[0068] [Table 25] Table 3(12} IF-2020-86290883-APN-ANP#INPI Page 57 of 122

[0069] [Table 26] Table 3(13) Compound No. Q Physical Property IF-2020-86290883-APN-ANP#INPI Page 58 of 122 3-85 Cz / X. Year H 3-86 A? N \ 3-87 8 3-88 • oz=*__ / 3-89 xf N \ 192-194 3-90 LT> N 3-91 / V >< / / Z= /

[0070] [Table 27] Table 3(14) Linear compound. Q Physical property IF-2020-86290883-APN-ANP#INPI Page 59 of 122 3-92 ti 3-93 ti 3-94 "ti 3-95 °ϊί IF-2020-86290883-APN-ANP#INPI Page 60 of 122 [Chemical formula 11] (1-7)

[0071] [Table 28] Table 4(1) Compound Kc. Q Physical property 4-1 NHKe 4-2 NKEt 4-3 Kii(n-Pr) 139-140 4-4 NJl(i-Pr} 4-5 Cv H 182-183 4-6 NHCHjPh 154-156 4-7 NK(cyc-Pr)(4-8-8) MH NHz 4-10 -Ν'* 1 4-11 is / \ 4-12 and 1

[0072] [Chemical Formula 12] IF-2020-86290883-APN-ANP#INPI Page 61 of 122 (1-8) (0073] [Table 29] Table 5(1} Compound no. QA Physical property 5-1 Me O 5-2 NH(E-) () 5-3 n-Pr 0 22G-221 5-4 cyc-?r 0 5-5 NH(CKe) 0 5-6 Ph 0 5-7 Me 0, 190-192 5-8 NEl} « xPr 0, n-0 0 22G-221 IF-2020-86290883-APN-ANP#INPI Page 62 of 122 5-1C cyC-Pr 0, 5-11 NH(OKe> 0 V)

[0074] [Table 30] Table 5{2) Compound NO. QA PHYSICAL PROPERTY 5-12 Ph 02 5-13 Me s 5-14 NKI£t) s 5-15 n-Pr s 5-16 cyc-Pr s 5-1? NliiOMe) s 5-18 Ph s 5-1S ΝΜβίΟΜβ) 0 5-20 NMe^OMe) IF-2020-86290883-APN-ANP#INPI Page 63 of 122 (0075) [Chemical formula 13]

[0076] [Table 31] Table 6(1) Compound No. Q Liquid Property 6-1 nn / 6-2 Q Á 276-278 6-3 ON 265-266 6-4 ' TZ=Z 263-2B4 6-5 263-264 6-6 b 275-279 6-7 (YN 251-253 IF-2020-86290883-APN-ANP#INPI Page 64 of 122 [Table 32]

[0078]

[0079] [Table 33] Table 7(1) IF-2020-86290883-APN-ANP#INPI Page 65 of 122 Compound no. 0 k YB Physical property 7-1 NH(Me) 0 - CHi- 129-131 7-2 NH(Et) o - -car 7-3 NH(n-Pr) 0 - -car 7-4 NE!i-?r) 0 - -ch?- 7--6 NH?0 - -ch?- 7--5 NH? NH(i-Bu) 0 - -cm?- 7-7 sa(sec-Bu) 0 - -ch?- 7-8 HE(texx-Bu) 0 - -ch?- 7-9 NE!KC! 0 - -CFz- 190-192 7-10 NHiEt} o - -CFi- 7-11 NH(n-Pr) o - -CF?- 7-12 Nil (i-Pr) - -CFa-

[0080] [Table 34] Table 7(2) Ccniposed NO. OAYB Physical property 7-13 NH(n-Bu) - -CF?- IF-2020-86290883-APN-ANP#INPI Page 66 of 122 7-14 NH(i-BU) O - -CEt” 7-15 NH(sec-Bj) 0 - -CFr 7-16 NH(tert-Bu) 0 - -CF?- 7-17 XX Cl N - 0 -CHj- 27-148 - NH-18 II - -CH;- 175-130 7-20 And VH - -CHr 204-206 7-21 - 0 -CH?- 103-104 7-22 Me s - - 7-23 Me 0 II - - 7-24 Me's 0.,0 's

[0081] [Table 35] Table 7(3) Corps NO. QAVB Physical Property 7-25 Et$ - IF-2020-86290883-APN-ANP#INPI Page 67 of 122 7-26 It 0 II - - 151-153 7-27 It 0. ,O 's' - - 114-115 7-28 NEIKe} o - X 7-29 NH(Kel 0 ne:om«) - 7-30 XH(EL) o Ni$:oMe) - 7-31 cyc o NH-32 WHO? C) NH(OMC) - 7-33 KM(MeJ or NHMe - 7-34 NM(EC) 0 NHMe - 7-713⁄4 MH(Ma) 0v.0 s - -CHj- 172-174 7-36 TZ \ - 0 -

[0082] [Table 36] Table 7(4) Compound NO. Q Λ VB Property iisica 7-37 • -CH;- 189-191 IF-2020-86290883-APN-ANP#INPI Page 68 of 122 7-38 H ' oo - -Cfiz- 7-39 NH(Me) - -CH(Ol¿e}-

[0083] [Chemical Formula 15] (MI)

[0084] [Table 37] Table 8(1) Corppost NO. QA R- R' X- X* Physical property is Ke O2 H Me EF 151-153 8-2 n-Pr 0 OMO HEF 150-159 0-3 —» OMe :< EF 182-183 8-4 n-?r 0 OMe H OMS H 178-180 OMe H-9 9-6 n-Pr 0 Cvle 11 FE 170-171 8-7 —· OMe HFE 170-171 IF-2020-86290883-APN-ANP#INPI Page69 of 122 ee ClhOCIh 0 OMe H - 137-140 6-9 CHaOCHj 0 OMe HEF 122-124 8-10 KH(EC) Π Me i·; F lbC-151 (00851 ( Table 38 Table 8(2) lompuestc NO. QAR* RJ X* X2 Physical Property 8-11 NK(t-Btl) O 11 Me II F 132-133 8-12 Me H Me FH 163-165 8-13 NH(t-Bu) o H Me FH 178-179 8-14 NH(Et) FH ¡ ¡ ¡ ¡ 15-15 O 8-15 cyc-Pr o H OMe F n 1.34511(24.1 ) 8-16 n-Pr 0 H OMe r H 8-17 F o CMe HF (1 8-18 CHCli 0 CKe HFK 8-19 cyc-Pr OMe 11 HF IF-2020-86290883-APN-ANP#INPI Page 70 of 122

[0087] [Table 39] Table 9(1} compound NO. QAX» X2 Physical property 9-1 H 0 c E 236-238 9-2 II or KO H 193--95 9-3 Π -N>· 0 HF 207-208 9-4 H o I·' H 236-237 9-5 H 0 Mo H 21 II-2 230-239 9-7 H MeO 0 F II 169-172 9-0 H MeO •^4» t <e 1? 145-146 IF-2020-86290883-APN-ANP#INPI Page 71 of 122 9-9 H MeO OHF 172-174 9-10 H FjHC^N^ FH

[0088] [Table 40] Table 9(2) Compound no. 0 A X1 X2 Physical property 9-11 H FjIIC^N^ o Me H 0 12 H FzHC^N^ 0 H Γ 21C 217 9-13 H o Cl H 9-14 H o Br E 9-15 H / >· o - E 9-16 H o K Cl H- 9-18 H- Br 9-18 HI 196-138 9-19 H / ¼ 0 H Ke 9-2C H / ¼ NCb )( IF-2020-86290883-APN-ANP#INPI Page72 of 122

[0089] [Table 41] Table 9(3) Coirpuesto NO. 0 A x' X2 Physical property 9-21 H / A 0 OMe H 9-22 11 0 CN H 9-23 H -A 0 H NO? 9-2Ί I! 0 H owe 9-25 II H CN

[0090] [Chemical Formula 17]

[0091] [Table 42] Table 10(1) Compound NO. 0 X* X1 Physical property IC-1 HT 99-101 10-2 ! θ HF 189–190 IF-2020-86290883-APN-ANP#INPI Page 73 of 122 10-3 X* / o EF 189-Í9C 10-4 nCn EF 148-149 10-3 nX VEF 227-229 ic-ΰ nA II ,NN*^ lí p 116-117 10-7 T,NM ς- 206-209 10-8 A θ OMF 163-165 10-9 ü HT 123-125 10-10 O ♦ 3 F 152-1

[0092] [Table 43] Table 10(2) Compound Ko. X' x: iisic Property 10-11 II - 132-133 IF-2020-86290883-APN-ANP#INPI Page 74 of 122 10-12 íAj, a F 123-J2S 10-13 ίΓ ΛοΖ~ HF 1.3465{25.5) 10-14 if Ν HF 161-163 10-15 10-16 nQ Cl HF 138-139 tí H τ- 164-165 10-17 γΓ f3c II r 145-146 10-18 tí HF 207-208 10-19 Ή oxγ HF 158-159 IF-2020-86290883-APN-ANP#INPI Page 75 of 122

[0093] [Table 44] Table 10(3} Compound No. QX* X: Physical property 10-20 O / oy H r 115-116 10-21 H = 10-22 o HF 10-23 y'sC. HF 10-24 / 5 ''Ν' N 1 HF 10-25 ο. Γ* EF IC-26 FH 10-27 FH 10-28 % / OFH 149-150 10-29 Ν-Γ ILA FH 163-165 IF-2020-86290883-APN-ANP#INPI Page 76 of 122

[0094] [Table 45] Table 10(4) Compound NO. Q X1 X2 Physical property 10-30 1' / > FH 209-211 10-31 / λ ZYFH 126-127 10-32 K ''NFH 10-33 1 >=o FH 10-34 N'NC* TH 121-123 10-35 ♦ o 2=7 1 - H 141-142 10-36 o FH 10-37 FK 173-175 10-36 if 0 FH IF-2020-86290883-APN-ANP#INPI Page 77 of 122 10-39 nV FH 1.5043(25.2)

[0095] [Table 46] Table 10(5) Compound NO. Q X' X2 Physical Property 10-40 J / NN·^ Cl FH 147-148 10-41 (λ C* n FH 139-140 IC—42 f3c FH 10-43 V\* w FE 225-226 10-44 FH 136-138 10-45 v Λ / oz FH 146-140 10-46 FH 10-47 0 \ / s\—· FH IF-2020-86290883-APN-ANP#INPI Page 78 of 122 10-48 FM 10-49 £ / > 1 FH

[0096] [Table 47] Table 10(6} Compound NO. 0 X1 X* Physical property 13-50 r E 10-51 \ z^ O · F li 10-52 °rT FH 10-53 ♦ o ZX z AFH 10-54 T >=OFH IC-55 C'VN^* 1? KF 151-153 10-56 nA o FH IF-2020-86290883-APN-ANP#INPI Page 79 of 122

[0097] [Chemical Formula 18]

[0098] [Table 48] Table 11(1) Compound NO. Q X1 X2 Physical property 11-1 NHMe F II 11-2 NEEt FM 11-3 NH(r.-Pr) F II 11-4 NH(l-Pr) F 3 11-5 Cv H — H 11-9 NH? IF-2020-86290883-APN-ANP#INPI Page 80 of 122 [ 0099] [Table 49] Table 11(2) Compound no. Q X1 Xa Physical PropertyCc 11-11 1 FH 11-12 1 / θ FH 11-13 NHMe HF 11-14 NHEt HF L1-1S KH(r.-Pr) HF 11-16 NH(i-Pr) HF 11-17 a.. HHF 11 HF-18 HF-HF. 11-19 NH(cyc-Pr} HF 11-20 NIUt-Bu} >1 F IF-2020-86290883-APN-ANP#INPI Page 81 of 122

[0100] [Table 50] Table 11(3) Compound No. Q X' X2 Physical Property 11-21 NH2 HF 11-22 1 HF 11-23 zo / \ HF 11-24 UN*** 1 HF

[0101] [Chemical formula 19] (1-8')

[0102] [Table 51] Table 12 Compound No. w AX· x; Physical property 12-1 cyc-Pr OFH 12-2 cyc-Px i*: F IF-2020-86290883-APN-ANP#INPI Page 82 of 122

[0103] [Chemical formula 20] (I-9Ί

[0104] [Table 52] Table 13 Compound NO. Q X1 X2 Physical Property 13-1 F & H 240-242 [Table 53] Table 14 Compound No. SH-WCN data (CDC1} / TMS, ppm) 2-19 δ 7.77-7.75 (d, 2HJ, 7.4C-7.38 (d, 23), 7.27-7.26 (d, 1H), 5.G3-5.84 {t, 1K), 5.61-5.56 (q, 1HI, 3.46-3.38 Jdd, 1K), 2.91-2.84 <dd, 111), 2.03 (5, 335 3-52 0 8.15 ($, 11() , 7.80-7,73 (ür 2hJ , id, ZH.I , 5.95-5.90 (q, 1H), 5.48 Ís. 23), 5.05 <br, 1H)

[0105] Agro-horticultural fungicides containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active principle are suitable for controlling diseases occurring in cereals, fruits, vegetables, other crops and ornamental plants.

[0106] Target diseases include filamentous fungal diseases, bacterial diseases, IF-2020-86290883-APN-ANP#INPI Page 83 of 122 viral or similar diseases. Filamentous fungal diseases that may be listed are, for example, diseases caused by imperfect fungi (Botrytis diseases, Helminthosporium diseases, Fusarium diseases, Septoria diseases, Cercospora diseases, Pseudocercosporella diseases, Rhynchosporium diseases, Pyricularia diseases and Alternaria diseases or similar); diseases caused by basidiomycetes (for example, Eemilelia diseases, Rhizoctonia diseases, Ustilago diseases, Typhula diseases and Puccinia diseases or similar);Diseases caused by ascomycota (e.g., Venturia diseases, Podosphaera diseases, Leptosphaeria diseases, Blumeria diseases, Erysiphe diseases, Microdochium diseases, Sclerotinia diseases, Gaeumannomyces diseases, Monilinia diseases, and Unsinula diseases, or similar); and diseases caused by other fungi (e.g., Ascochyta diseases, Phoma diseases, Pythium diseases, Corticium diseases, and Pirenophora diseases, or similar). Bacterial diseases that may be listed include, for example, Pseudomonas diseases, Xanthomonas diseases, and Erwinia diseases, or similar. Viral diseases, for example, include those caused by tobacco mosaic virus, or similar.

[0107] Specific filamentous fungal diseases that can be listed include, for example, rice blast (Piricularia oryzae), rice sheath blight (Rhizoctonia solani), and brown spot of rice. IF-2020-86290883-APN-ANP#INPI Page 84 of 122 (Cochiobolus miyabeanus), rice seedling blight (Rhizopus chinensis, Pythium graminicola, Fusarium graminicola, Fusarium roseum, Mucor sp., Phomas sp., Trichoderma sp.), rice bakanae disease (Gibberella fujikuroi), powdery mildew in barley and wheat or similar crops (Blumeria graminis), powdery mildew in cucumbers or similar crops (Sphaerotheca fuliginea), powdery mildew in eggplant or similar crops (Erysiphe cichoracoarum) and powdery mildew in other host plants, cercospora leaf spot in barley, wheat, or similar crops (Pseudocercosporella herpotrichoides), blight in wheat or similar crops (Urocystis tritici), snow mold in barley, wheat, or similar crops (Microdochium nivalis, Pythium iwayamai, Typhia ishikariensis, Typhla incarnata, Esclotisella), fusarium head blight on barley, wheat or similar (Fusarium graminearum, Fusarium gallinaceum, Fusarium culmorun, Microdochium nivalis), rust on barley, wheat or similar (Puccinia recondita,Puccinia striiformis, Puccinia graminis), foot disease on barley, wheat or similar (Gaeumannomyces graminis), crown rust of oats (Puccinia coronata), rust on other plants, gray mold on cucumbers, strawberries or similar (Botrytis cinerea), Sclerotinia rot on tomatoes, cabbages or similar (Sclerotinia sclerotiorum), late blight on potatoes, tomatoes or similar (Phytophthora infestans), late blight on other plants, cucumber mildew (Pseudoperonospora cubensis), grape downy mildew (Plasmopara Vitícola), downy mildew on various plants, chamomile scab {Venturia inaequalis), apple alternary spot (Alternaria mali), black pear spot (Alternaria kikuchiana), citrus melanosis (Diaporthe citri), citrus scab (Elsinoe Fawcetti's disease, sugar beet leaf spot, IF-2020-86290883-APN-ANP#INPI Page 85 of 122 (Cercospora beticola), brown leaf spot of peanut (Cercospora arachidicola), late leaf spot of peanut {Cercospora personate}, leaf spot in wheat {Septoria tritici), glume spot of wheat {Leptosphaeria nodorum), net spot of barley {Pirenophora teres), barley stripe (Pirenophora graminea), barley scald (Rhynchosporium secalis), loose wheat blight (Ustilago nuda), stinking smut of wheat (Tilletia caries), brown patch in turfgrass (Rhizoctonia solani) and dollar spot in turfgrass (Sclerotinia homoeocarpa) or similar.

[0108] Specific bacterial diseases that can be listed are diseases caused by Pseudomonas spp., for example, bacterial spot of cucumber (Pseudomonas syringae pv. Lachrymans), bacterial wilt disease of tomato (Pseudomonas solanacearum) and bacterial grain rot of rice (Pseudomonas glumae); diseases caused by Xanthomonas spp., for example, black rot of cabbage (Xanthomonas campestris), bacterial leaf blight of rice (Xanthomonas oryzae) and citrus canker (Xanthomonas citrii); and diseases caused by Erwinia spp., for example, soft rot of cabbage (Erwinia carotovora) or similar diseases.

[0109] The useful plants to which the compound of the present invention represented by the general formula (I) or salts thereof can be applied are not particularly limited, and the following plants may be listed as examples thereof: cereals (for example, rice, barley, wheat, rye, oats, corn or similar); beans and peas IF-2020-86290883-APN-ANP#INPI Page 86 of 122 such as soybeans, red beans, broad beans, peas, beans, peanuts or similar; fruit trees (e.g., apple, citrus and other fruits, pear, grape, peach, plum, cherry, walnut, chestnut, almond, banana, strawberry, or similar); leafy vegetables and fruits (e.g., cabbage, tomato, spinach, broccoli, lettuce, onion, green onions (spring onions and scallions), green peppers, eggplant, strawberries, peppers, okra, scallions, or similar); root crops (e.g., carrots, potato, sweet potato, taro, radish, lotus rhizome, turnip, burdock, garlic, scallions, or similar); processing crops (e.g., cotton, flax, beetroot, hops, sugar cane, sugar beet, olive, gum, coffee, tobacco, tea, or similar); cucurbit plants (e.g., pumpkin, cucumber, muskmelon, watermelon, melon, or similar);pasture plants (e.g., orchard grass, sorghum, timothy, clover, alfalfa or similar), lawn grasses (e.g., mascarenegrass, bentgrass or similar); perfume crops (e.g., lavender, rosemary, thyme, parsley, pepper, ginger or similar); flowers and ornamental plants (e.g., chrysanthemum, rose, carnation, orchid, tulip, lily or similar); garden trees (e.g., ginkgo tree, cherry tree, goldenleaf plant or similar), and timber trees (e.g., white fir, silver fir, pine, axe-leaf pine, Japanese cedar, Japanese eypress, eucalyptus or similar).

[0110] The aforementioned plants include plants that have been conferred resistance to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazethapyr or tifcinsuifuron-methyl, and inhibitors of the IF-2020-86290883-APN-ANP#INPI Page 87 of 122 EPS? synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim and herbicides such as bromoxynil, dicamba, 2,4-D, or similar by means of a classical genetic improvement method or a genetic engineering technique.

[0111] Examples of plants that have been bred for resistance through a classical breeding method include rapeseed, wheat, sunflower, and rice resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which are already commercially available under the product name Clearfield (registered trademark). Similarly, there is a soybean variety that has been bred for resistance to sulfonylurea-based ALS-inhibiting herbicides such as typhensulfuron-methyl through a classical breeding method, which is already commercially available under the product name STS soybean. Likewise, examples of plants that have been bred for resistance to acetyl-CoA carboxylase inhibitors, such as trione oxime or aryloxyphenoxypropionic acid herbicides, through a classical breeding method include SR maize. The plant conferred resistance to acetyl-CoA carboxylase inhibitors is described in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), vol. 87, pp. 7175-7179 (1990) or similar. A variant of acetyl-CoA carboxylase resistant to an acetyl-CoA carboxylase inhibitor has been reported in Weed Science, vol. 53, pp. 728-746 (2005) or similar, and a plant resistant to the inhibitors can be generated. IF-2020-86290883-APN-ANP#INPI Page 88 of 122 of acetyl-CoA carboxylase by introducing a gene of a similar acetyl-CcA carboxylase variation into a plant using genetic engineering techniques, or by introducing a variation that confers resistance to a plant acetyl-CoA carboxylase; furthermore, plants resistant to acetyl-CoA carboxylase inhibitors or ALS inhibitors or the like can be generated by introducing a site-directed amino acid substitution variation in an acetyl-CoA carboxylase gene or the plant ALS gene by introducing into the plant cell a nucleic acid in which a base substitution variation has been introduced, represented by the Chimeraplasty Technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318). The compound of the present invention represented by general formula (I) or salts thereof can also be used for these plants.

[0112] Furthermore, examples of toxins expressed in such genetically engineered crops include: insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; δ-endotoxins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl, or Cry9C, derived from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins derived from nematodes; animal-generated toxins, such as scorpion toxin, spider toxin, bee toxin, or insect-specific neurotoxins; mold fungal toxins; plant lectins; agglutinin; protease inhibitors such as a trypsin inhibitor, a serine protease inhibitor, patatin, IF-2020-86290883-APN-ANP#INPI Page 89 of 122 cystatin, or a papain inhibitor; ribosomal inactivating proteins (RIPs), such as Usin, maize RIP, abrin, lufin, sapcrin, or bryodin; spheroid-metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, or cholesterol oxidase; an ecdysone inhibitor; EMG-CoA reductase; ion channel inhibitors such as a sodium channel inhibitor or a calcium channel inhibitor; juvenile hormone esterase; a diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0113] Furthermore, the toxins expressed in such genetically modified crops also include: hybrid toxins, partially deleted toxins, and modified toxins of δ-endotoxin proteins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3Abl, Cry3C, Cry9C, Cry34Ab, or Cry35Ab; insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced from a novel combination of the different domains of these proteins, using a genetic engineering technique. CrylAb, which involves the deletion of a portion of an amino acid sequence, is known as a partially deleted toxin. In modified toxins, one or more amino acids of naturally occurring toxins are substituted.

[0114] Examples of such toxins and genetically modified plants capable of synthesizing such toxins are described in documents EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529.. EP-A-451 878, WO 03 / 052073 or similar. IF-2020-86290883-APN-ANP#INPI Page 90 of 122

[0115] The present inventive agro-horticultural fungicide can also be used in combination, or systematically, with such technologies.

[0116] To control various diseases, the present agro-horticultural fungicide of the invention is applied to the plants in which the appearance of diseases is expected, either in the form of a dilution or suspension in an adequate amount of water or similar to an effective dosage for disease control.For example, to control the occurrence of diseases in fruit trees, cereals, and vegetables, the composition can be used directly for foliar treatment or for seed treatments such as seed immersion in the agent solution, seed coating, seed treatment, or similar methods, or for root absorption through soil treatment or similar methods, such as incorporation into the soil layer, row treatment, soil incorporation, seedling cell treatment, hole formation treatment, plant base treatment, topcoating, rice seedling box application, submerged application, or similar methods. Furthermore, the application of the agro-horticultural insecticide of the present invention to the nutrient solution in aquatic cultivation, fumigation, and injection into tree stems or similar applications are also possible.

[0117] Furthermore, the present agro-horticultural fungicide of the invention can be used as is with the dilution IF-2020-86290883-APN-ANP#INPI Page 91 of 122 appropriate with water or similar, or in suspension, in an effective quantity for disease control at a site where disease occurrence is expected.

[0118] As a method of seed treatment, reference may be made to a method of immersing seeds in a diluted or undiluted liquid or solid preparation of the composition and thereby causing the agent to penetrate the seeds; a method of mixing a solid or liquid preparation with seeds to coat them in powder and thereby causing the agent to adhere to the surface of the seed; a method of mixing the preparation with an adhesive carrier such as resin, polymer or the like and coating the seeds with said adhesive mixture; a method of spraying the preparation in the vicinity of the seeds simultaneously with sowing or the like. "Seed" to be treated with seed trapping means a plant body of the early stage of cultivation used for plant reproduction, encompassing not only seeds but also plant bodies for nutrient reproduction such as bulb, tuber, seed tuber, common sprout, aerial tuber, scaly bulb or stems for cuttage (method of propagation by cuttings) or the like.

[0119] The "soil or growing medium" for plants when carrying out the method of use of the present invention means a support for growing a plant, in particular, a support on which the roots grow; its material quality is not limited, any material is acceptable as long as the plant can grow on it. For example, the following can be used: IF-2020-86290883-APN-ANP#INPI Page 92 of 122 referred to as soils, mats, water or similar, specific examples for materials such as sand, pumice stone, vermiculite, diatomaceous earth, agar, gelatinous materials, polymeric materials, rock wool, glass wool, wood chips, bark or similar.

[0120] As a method for spraying onto foliage parts of crops or the like, reference may be made to spraying a liquid formulation such as an emulsifiable concentrate, a flowable agent or the like, or a solid formulation such as a wettable powder or a wettable granule or the like, which has been properly diluted with water, powder spraying, fumigation or the like.

[0121] As a method of application in the soil, one can list applying a liquid preparation diluted with water or undiluted at the base of the plant, in the seedbed for growing seedlings or the like, sprinkling the granules on the base of the plant or in the seedbed, sprinkling a powder, wettable powder, granule or wettable granules on the soil and mixing with all the soil before sowing or before transplanting, spraying a powder, wettable powder, wettable granule, granules or the like in planting holes, sowing rows or the like.

[0122] As a method for applying to a rice cultivation box in a paddy field, although the preparation method may vary depending on the application time, such as application during the sowing period, greening period, or transplanting period, application in the form of powder or granules can be listed. IF-2020-86290883-APN-ANP#INPI Page 93 of 122. Wettable powders, granules, or similar materials can also be used. Application by mixing with the soil is also possible. This involves mixing the soil with a wettable powder, granule, or granules, which are then mixed into the bedding material, covering the soil or the entire surface. Another possible method is simply applying the product by layering soil with various formulations.

[0123] To apply fertilizer to a rice field, typically a submerged rice field, a solid preparation such as a giant packet, granules, wettable granules, or similar, or a liquid formulation such as a fluidized, emulsifiable concentrate, is sprinkled on top. Alternatively, a suitable agent can be sprayed or injected directly into the soil, either as is or mixed with fertilizers, at transplanting time. A chemical solution of an emulsifiable concentrate can also be applied directly to the water inlet or flow source of the irrigation system, resulting in a labor-saving application using the supplied water.

[0124] In the case of upland field crops, application to the growing medium surrounding the seeds or plant bodies is available from sowing until seedling emergence. For crops where seeds are sown directly in the field, in addition to direct application to the seeds, application to the base of the furrows during the growing period is preferred. Spraying with granules or irrigation with a liquid formulation, diluted with water or undiluted, is also possible. Another preferred treatment is mixing the IF-2020-86290883-APN-ANP#INPI Page 94 of 122 granules with the culture carriers before sowing and sowing the seeds thereafter.

[0125] In cases where seedlings are to be transplanted, treatment at sowing time or during the seedling stage is preferred, in addition to direct seed treatment, irrigation of the seedling bed with a liquid solution or spraying of granules is preferable. Furthermore, applying granules directly to the planting holes at sowing time or mixing them into the growing medium near the transplanting sites is also a preferable treatment.

[0126] The present inventive compound represented by the general formula (I) or salts thereof is generally used after having been formulated in a form that is convenient to use by the standard method for formulating agrochemicals.

[0127] Namely, the compound of the present invention represented by the general formula (I) or salts thereof may be used after having been optionally mixed together with an adjuvant in a suitable proportion and prepared in a suitable form, such as a (fluid) suspension, emulsifiable concentrate, oil dispersions, soluble concentrate, wettable powder, wettable granules, granules, powder tablets, packets, jumbos, suspoemulsion or the like by means of dissolution, separation, suspension, mixing, impregnation, adsorption or adhesion.

[0128] IF-2020-86290883-APN-ANP#INPI Page 95 of 122 The agricultural fungicides of the present invention may contain, in addition to the active ingredient, additive components commonly used in agricultural formulations, if necessary. Such additive components may include a carrier (such as a solid or liquid carrier), a surfactant, a dispersant, a wetting agent, a binder, an adhesion promoter, a thickener, a coloring agent, an extender, a spreader, an antifreeze agent, an anti-caking agent, a disintegrant, and a stabilizing agent or similar. Furthermore, an antiseptic agent and plant parts may be used as additive components if required. These additive components may be used alone or in combination.

[0129] As a solid carrier, for example, one can list a natural mineral such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, or diatomaceous earth; an inorganic salt such as calcium carbonate, ammonium sulfate, sodium sulfate, or potassium chloride, synthetic silicic acid, or synthetic silicate; an organic solid vehicle such as starch, cellulose, or plant powders such as sawdust, coconut husk, tobacco stalk, and corn cob; a plastic carrier such as polyethylene, polypropylene, or polyvinylidene chloride; or urea, inorganic hollow materials, plastic hollow materials, or fumed silica such as carbon white. These can be used alone or in combination with one or more.

[0130] As a liquid carrier, for example, one can IF-2020-86290883-APN-ANP#INPI Page 96 of 122 list alcohols such as a monohydric alcohol such as methanol, ethanol, propanol, isopropanol or butanol or a polyhydric alcohol such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol or glycerol; a derivative of a polyhydric alcohol such as propylene glycol ether; a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone or cyclohexanone; an ether such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether or THE*; an aliphatic hydrocarbon such as normal paraffin, naphthene, isoparaffin, kerosene or mineral oil; an aromatic hydrocarbon such as benzene, toluene, xylene, solvent naphtha or alkyl naphthalene; a halogenated hydrocarbon such as dichloroethane, chloroform or carbon tetrachloride; an ester such as eryl acetate, diisopropyl phthalate.or, dibutyl phthalate, dioctyl phthalate, or dimethyl adipate; a lactone such as [gamma]-butyrolactone; an amide such as dimethylformamide, diethylformamide, dimethylacetamide, or N-alkylpyrrolidinone; a nitrile such as acetonitrile; a sulfur compound such as dimethyl sulfoxide; a vegetable oil such as soybean oil, rapeseed oil, cottonseed oil, or castor oil; or water. They may be used alone or in combination with two or more.

[0131] The following can be listed as surfactants used as dispersing or wetting agents: a non-ionic surfactant such as a sorbitan fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a sucrose fatty acid ester, a polyoxyethylene fatty acid ester, a polyoxyethylene resin acid ester, a diester of IF-2020-86290883-APN-ANP#INPI Page 97 of 122 polyoxyethylene fatty acid, a polyoxyethylene alkyl ether, a polyoxyethylene alkyl phenyl ether, a polyoxyethylene dialkyl phenyl ether, a formalin condensate - polyoxyethylene alkyl phenyl ether, a polyoxyethylene polyoxypropylene block copolymer, a polyoxyethylene alkyl polyoxyethylene polypropylene block polymeric ether, a polyoxyethylene alkylamine, a polyoxyethylene fatty acid amide, a polyoxyethylene fatty acid bisphenyl ether, a polyalkylene benzyl phenyl ether, a polyoxyalkylene styryl phenyl ether, an acetylenediol, an acetylenediol with added polyoxyalkylene, a polyoxyethylene ethyl silicon ether, a silicon ester type, a fluorinated surfactant, a polyoxyethylene castor oil or a polyoxyethylene hardened castor oil; an anionic surfactant such as an alkyl sulfate, a polyoxyethylene alkyl ether sulfate, a polyoxyethylene alkyl phenyl ether sulfate, a polyoxyethylene styryl phenyl ether sulfate, an alkylbenzenesulfonate, a lignin sulfonate, an alkylsulfosuccinate, a naphthalenesulfonate, an alkylnaphthalenesulfonate, a salt of a naphthalenesulfonate formalin condensate, a salt of an alkylnaphthalenesulfonate formalin condensate, a fatty acid salt, a polycarboxylic acid salt, an N-methyl fatty acid sarcosinate, a resin acid salt, a polyoxyethylene alkyl ether phosphate, or a polyoxyethylene alkyl phenyl ether phosphate; a cationic surfactant such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride and chloride of IF-2020-86290883-APN-ANP#INPI Page 98 of 122 alkyldimethylbenzonium; and an amphoteric surfactant, such as an amino acid or betaine. These surfactants can be used alone or in combination with two or more

[0132] As an agent that imparts adhesion or binder, for example, one can list carboxymethylcellulose or its salt, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, polysodium acrylate, a polyethylene glycol having an average molecular weight of 6,000 to 20,000, a polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, or a natural phosphatide.

[0133] As a thickener, for example, one can list a water-soluble polymer such as xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, an acrylic polymer, a starch compound or polysaccharide; or a fine inorganic powder, such as high-purity bentonite or white carbon.

[0134] As a coloring agent, for example, one can list an inorganic pigment such as iron oxide, titanium oxide, or Prussian blue; or an organic dye such as an arizarin dye, an azo dye, or a metal phthalocyanine dye.

[0135] As an antifreeze agent, for example, one can list a polyhydric alcohol such as ethylene glycol, diethylene glycol, propylene glycol or glycerol.

[0136] IF-2020-86290883-APN-ANP#INPI Page 99 of 122 As an additive component for an anti-caking agent or disintegrating agent, for example, one can list starch, alginic acid, a polysaccharide such as mannose or galactose, polyvinylpyrrolidone, white carbon, ester gum or petroleum resin, sodium tripolyphosphate, sodium hexamethylphosphate, metallic salt of stearic acid, a cellulose powder, dextrin, a methacrylate copolymer, a polyvinylpyrrolidone, a polyaminocarboxylic acid chelate compound, a styrene / isobutylene / maleic anhydride sulfonate copolymer, a starch / polyacrylonitrile graft copolymer. [0137 J As a stabilizer, for example, one can list a drying agent such as zeolite, quicklime, or magnesium oxide; an antioxidant such as a type of phenol, a type of amine, a type of sulfur, or a type of phosphorus; or an ultraviolet absorber such as a type of salicylic acid or a type of benzophenone.

[0138] As an antiseptic, for example, potassium sorbate or 1,2-benzthiazolin-3-one can be listed.

[0139] In addition, if necessary, a functional spreader, an activity enhancer such as piperonyl butoxide, an antifreeze agent such as propylene glycol, an antioxidant such as BHT, or other additive agents such as a UV absorber can be used.

[0140] The content of the active ingredient compound may vary according to need; the content may be appropriately selected from the range between 0.01 and 90 parts by weight in terms of 100 parts by weight of the IF-2020-86290883-APN-ANP#INPI 100 Page 100 of 122 agro-horticultural fungicide of the present invention. For example, for powders, granules, emulsifiable concentrates or wettable powders, the suitable content is from 0.01 to 50 parts by weight (0.01 to 50% by weight for the entire weight of the agro-horticultural fungicide),

[0141] The application dose of the controlling agent of the harmful organism of the present invention varies depending on several factors, such as, for example, a purpose, insect pests to be controlled, growth stage of a plant, tendency for insect pests to appear, climate, environmental conditions, preparation form, application method, application site and application time; the dosage of the active ingredient compound can be correctly chosen in a range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 areas, depending on the purpose.

[0142] When using agricultural and horticultural fungicides comprising the compound of the present invention of general formula (I) or salts thereof, it is diluted to a concentration suitable for spraying or treated as is.

[0143] The agro-horticultural fungicides of the present invention, in particular the agro-horticultural insecticide, can be used in mixtures with other agrochemical insecticides, acaricides, nematocides, fungicides, or biological pesticides to expand the spectrum of controllable diseases and pests, extend the control period, or reduce the dosage. Furthermore, their use in mixtures with herbicides and plant growth regulators... IF-2020-86290883-APN-ANP#INPI 101 Page 101 of 122. For plants, fertilizers, or similar products, depending on the intended use. Representative compounds are listed below, but this list is not exhaustive.

[0144] The following agro-horticultural fungicides can be mentioned as examples of fungicides that will be used for this purpose: aureofungin, azaconazole, azitiram, acipetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylphos, ametoctradine, allyl alcohol, aldimorph, amobam, isothianiol, isovaledione, isopirazam, isofetamid, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenphos, imazali, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, imibenconazole, uniconazole, uniconazole-P, eclomezol, edifenphos, etaconazole, ethaboxam, etirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobir.a, epoxiconazole, oxadixil, oxatiapiprolin, oxycarboxin, copper-8quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid, octylinone, ofurace, orisastrobin, soil fungicides such as carbarn (metam-sodium); kasugamycin, carbamorph, carpropamid, carbendazim, carboxins, carvone, quinazamid, quinacetol, quinoxifene, chinometionat, quinomethionate, Captafol, Captan, Kiralaxil, Quincenazo.l, Quincocene, Guazatine, Cufraneb, Cuprobam, Coumoxystrobin, Gliodine, Griseofulvin, Climbazol, Cresol, kresoxim-motil, clozolinate, clotrimazole, clobenthiazone, chloraniformethane, chloranil, chlorquinox, chloropicrin, chlorfenazole, chlordinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zarilamid, ciazofamid, diethyl pyrocarbonate, dietofencarb, cyclafuramid, diclocimet, diclozoline, diclobutrazol, diclofluanid, cycloheximide,. IF-2020-86290883-APN-ANP#INPI 102 Page 102 of 122 diclomezine, dicloran, dichlorophen, diclona, ​​disulfiram, ditalimfos, dithiacn, diniconazole, diniconazole-M, zineb, dinocap, dinocton, dinosuifon, dinoterbon, dinobuton, dinopenton, dipimethirone, dipyrithione, diphenylamine, difenoconazole, ciflufenamid, diflumetorim, ciproconazole, cyrodinil, ciprofuram, cipondazole, simeconazole, dimethrimol, dimethomorph, cymoxanii, dimoxystreptomycin, ziram, siltiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazine, thiadifluor, thiabendazole, thioximid, thiochlorfenf ini thiophanate, thiophanate-methyl, tiffluzamide, thiophene, thioquinox, thiram, decafentim, tecnazcene, teclophthalam, tecoram, tetraconazole, debacarb, dehydroacetic acid, tebuconazole, tebufloquine, dodicin, dodine, DBEDC, dodemorph, drazoxolon, triadimenol, triadimefon, triazbutyl, triazoxide, triamiphos, triarimol, triclamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, tributyleneethane oxide, triflumizole, trifloxistrob.ina, triforin, tolylfluanid, tolclofos-methylo, tolprocarb, natamicina, nabam, nitroestyreno, nitrotal-isopropyl, nuarimol, cobre nonilfer.ol sulfonate, halaccrinate, validamycin, valifenalate, proteína harpin, picarbutrazox, bixafeno, picoxistrobin, picobenzamida, bitionol, bitertanol, hidroxiisoxazol, hidroisoxazolpotasio, binapacril, bifonil, piperalin, himexazol, piraox istrobin, piracarbolid, pyraclostrobin, pyraziflumid, pyrazofos, pyramethostrobin, pyriofenone, pyridinitril, pidif lumetofen.o, pidif lumetofeno, pirisoxazol, pirifenox, piribencarb, pyrimethanil, piroxiclor, piroxifur, piroquilon, vinclozolin, famoxadona, fenapanil, fenamidona, fenaminosulf, phenaminstrobin, fenarimol, fenitropan, fenoxanil, ferimzona, ferbam, fentin, fenpiclonil, fenpyrazamine,. IF-2020-86290883-APN-ANP#INPI 1.03 Page 103 of 122 fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, butiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furametpir, furalaxil, fluacripyrim, fluazinam, fluoxastrobin, fluotrimazole, fluopicolide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, furfural, furmeciclox, flumetover, flumorf, proquinazid, prochloraz, procymidone, prothiocarb, protioconazole, propamocarb, propiconazoi, propineb, furophanate, probenazole, bromuconazole, hexachlorobutadiene, hexaconazole, hexylthiophos, betoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorph, pencicuron, benzohydroxamic acid, benzovindiflupyr, bentaluron, bentiazole, benthiavalicarbisopropyl, penthiopyrad, penflufen, boscalid, fosdifene, fosetyl, fosetyl-Al, polyoxins, polioxorim, polycarbamate, folpet, formaldehyde, machine oilmaneb, mancozeb, mandipropamid, mandestrobin, miclozoline, miciobutanil, mildiomycin, milneb, mecarbinzid, metasulfocarb, metazoxolon, metam, metamsodium, metalaxyl, metalaxyl-M, metiram, methyl isothiocyanate, meptyldinocap, metconazole, metsulfovax, metfuroxam, metominostrobin, metrafenone, mepanipirim, mefenoxam, meptyldinocap, mepronil, mebenil, iodomethane, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate; inorganic fungicides such as silver or similar; sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium bicarbonate, sodium bicarbonate, sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, copper oxine, zinc sulfate, sulfate pentahydrate IF-2020-86290883-APN-ANP#INPI 104 Page 104 of 122 copper or similar.

[0145] As agro-horticultural insecticides, acaricides, and nematocides to be used for the same purpose, for example, the following are mentioned: 3,5-xylyl methylcarbamate (XMC), Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis kurstaki, Bacillus thuringiensis tenebrionis, crystalline protein toxin produced by Bacillus thuringiensis, BPMC, Bt toxin insecticidal compound, CPCBS (chlorfenson), CCIP (dichlorodiisopropyl ether), DC (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPICi, acrinathrin, azadirachtin, azinphos-methyl, acequinocil, acetamiprid, acetoprol, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanicarb, aldicarb, aldoxicarb, aldrin, alfa-ondosulfan, alfa-cypermethrin, albendazole, allethrin, isazophos, isamicophos, isoamidophos, isoxation, isofenphos,iscprocarb: MIPC, epsilon-metoflutrina, epsilon-momfluorotrina, ivermectina, imiciafos, imidacloprid, imiprotrina, indoxacarb, esfenvalerato, etiofencarb, etion, etiprol, etoxazol, etofenprox, etoprofos, etrimfos, emamectina, emamectin-benzoato, endosulfan, empentrina, oxamilo, oxidemeton-metilo, oxideprofos: ESP, oxibendazol, oxfendazol, oleato de potasio, oleato de sodio, cadusafos, kappa-bifentrina, cartap, carbarilo, carbosulfan, carbofurilo, gammacihalotrina, xililcarb, quinalfos, kinopreno, quinometionato, cloetocarb, clotianidina, clofentecina, cromafenozida, clorantraniliprol, clorethoxifos, clordimeform, clordano, clorpirifos, clorpirifos-metilo, IF-2020-86290883-APN-ANP#INPI 105 Página 105 de 122 clorfenapir, clorfenson, clorfenvinfos, clorf luazuron, clorobenzilato, clorobenzoato, cloroprallotrina, keltano(dicofol, salition, cihalodiamida, cianofos: CYAP, diafentiuron, diamidafos, ciantraniliprol, tetacipermetrina, dienoclor, cienopirafeno, dioxabenzofos, diofenolan, sigma-cipermetrina, ciclaniliproi, diclofention: ECP, ciclcprotrir.a, diclorvos: DDV?, disulfoton, dinotefurilo, cihalotrina, cifenotrina, ciflutrina, diflubenzuron, ciflumetofeno, diflovidazin, cihexatina, cipermetrina, dimetilvinfos, dimetoato, dimeflutrina, silafluofeno, ciromazina, spinetoram, spinosad, spirodi cl of eno, spirotetramat, spiromesifer.o, sulfluramid, sulprofos, sulfoxaflor, zeta-cipermetrina, diazinon, tau-fluvalinato, dazomet, tiacloprid, tiamethoxam, tioxazafeno, tiodicarb, tiociclam, tiosultap, tiosultap-sodio, tionazina, tiometon, deet, dieldrina, tetraclorvinfos, tetradifon, tetraniliprol, tetrametilflutrina, tezrametrina, tebupirimfos, tebufenozida, tebufenpirad,teflutrina, teflubenzuron, demeton-S-metilo, temefos, deltametrina, terbufos, tralopiril, tralometrina, transílutrina, triazamato, triazuron, triclamida, triclorfon: DEP, triflumezopirim, triflumuron, tolfenpirad, naled: BRP, nitiazina, nitenpiram, novaluron, noviflumuron, hidropreno, vaniliprol, vamidotion, paration, paration-motilol, halfenprox, halofenozida, bistrifluron, bisultap, hidrametilnon, hidroxi propil almidón, binapacril, piflubumida, bifenazato, bifentrina, pimetrozina, piraclorfos, pirafluprol, piridafention, piridaben, piridalilo, pirifluquinazon, piriprol, piriproxifeno, pirimicarb, pirimidifeno, piriminostrobina, pirimifosmetilo, piretrinas, fipronil, fenazaquin, fenamifos, bromopropilato, fenitrotion: ΜΞΡ, fenoxicarb, fenotiocarb, IF-2020-86290883-APN-ANP#INPI 106 Page 106 of 122 phenothrin, fenobucarb, fensulfothion, fenthion: MPP, phentoate: PAP, fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fosthiazate, formetanate, butathiofos, buprofezin, furatiocarb, pralletrin, fluacripyrim, fluazaindolizinae, fluazinam, fluazuron, fluensulfone, fluxametamidae, flucicloxuron, flucitrinate, fluvalinate, flufiprol, flupyradifurone, flupyrazophos, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, fluproxifen, flubrocitrinate, fluhexafon, flubendiamide, flumethrin, flurimfen, prothiophos, protrifenbuto, flonicamid, propafos, propargita: 3PPS, profenofos, profluthrin, propoxur: PHC, flometoquine, bromopropilatoe, beta-cyfluthrin, hexaflumuron, hexithiazox, heptafluthrin, heptenophos, permethrin, benclotiaz, bendiocarb, bensultap, benzoximate, benfuracarb, foxim, fosalone, fostiazate, fostietan, phosfamidon, phosphocarb, phosmet: PHP, pollinactins, formetanate, fcrmotion, phorate, machine accept, malathion, milbeinicin, milbemycin-A,milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidofos, metam-anionium, metam-sodium, methiocarb, methidathion, DMTP, methyl isothiocyanate, methyl neodecanamide, methyl parathion, methoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, mevinfos, monocrotofos, monosultap, monofluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisole hydrochloride, fenbutatin oxide, morantel tartar, methyl bromide, cyhexatine, calcium cyanamide, calcium polysulfide, sulfur, nicotine sulfate, or similar substances.

[0146] The following herbicides can be listed as being used for the same purpose, IF-2020-86290883-APN-ANP#INPI 107 Page 107 of 122 for example: 1-naphthylacetamide, 2,4-PL, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPAtioetilo, MCPB, ioxinil, aclonifeno, azafer.idin, acifluorfeno, aziprotrina, azimsulfuron, asulam, acetoclor, atrazina, atraton, anisuron, anilofos, aviglicina, ácido abscísico, amicarbazona, amidosulfuron, amitrol, aminociclopiraclor, aminopiralid, amibuzin, amiprofos-metilo, ametridiona, ametrina, alaclor, alidoclor, alloxidim, aiorac, iofensulfuron, isouron, isocarbamid, isoxaclortcl, isoxapirifop, isoxaflutol, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinata, isometiozin, inabenfida, ipazina, ipfencarbazona iprimidam, imazaquin, imazapic, imazapir, imazametapir, imazametabenz, imazarnetabenz-metilo, imazamox, imazetapir, imazosulfuron, indaziflam, indanofan, ácido indolebutirico, uniconazol-P, eglinazina, esprocarb, etametsulfuron, etametsulfuron-metilo, etalfluralin, etiolato, eticlozato etilo, etidimuron, etinofeno, etefon, etoxisulfuron, etoxifeno, etnipromid, ethofumesato, etobenzanid, epronaz, erbon, endotal, oxadiazon, oxadiargil, oxaziclomefona, oxasul.furon, oxapyrazon, oxifluorfeno, oryzalin, orthosulfamuron, orbencarb, cafenstrol, cambendichlor, carbasulam, carfentrazona, carfontrazona-ethyl, karbutylate, carbetamida, carboxazol, quizalofop, quizalofop-P, quizalofop-ethyl, xylaclor, quinoclamine, quinonamid, quinclorac, quinmerac, cumiluron, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxifonac, clcdinafoo, clodinafop-propargyl, chlorotoluron, clopivalid, cloproxidim, cloprop, chlorbromuron, clofop, clomazona, clomethoxinil, clomethoxifeno, clomeprop, chlorazifop, chlorazine,. IF-2020-86290883-APN-ANP#INPI 108 Page 108 of 122 cloransulam, cloranocril, cloramben, cloransulam-metilo, cloridazon, clorimaron, clorimuron-etilo, clorsulfuron, clortal, clortiamid, clortoluron, clornitrofeno, clorfenac, clorfenprop, clorbufam, clorf lurazol, clorflurenol, clorprocarb, clorpropam, clormequat, cloreturon, cloroxinil, cloroxuron, cloropon, saflufenacil, cyanazine, cyanathrine, di-alato, diuron, diethamquat, dicamba, cicluron, cycloate, cicloxidim, diclosulam, ciclosulfamuron, ciclopirimorato, diclorprop, diclorprop-P, dichlobenil, diclofop, diclofop-metilo, d.iclormato, dichloralurea, diquat, cisanilida, disul, siduron, dithiopir, dinitranine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinophenate, dinoprop, cihalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat, cibutrin, cyprazine, ciprazol, diflufenican, diflufenzopyr, dipropetrin, cipromid, ciperquat, gibberellin, simazine, dimexane, dimetaclor, dimidazon, dimethamethrin, dimethenamid, simethrin, srmeton, dimepiperate,dimefuron, cinmetilin, swep, sulglicapin, sulcotrione, sulfallato, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-metilo, secbumeton, setoxidim, sebutilazina, terbacil, daimuron, dazomet, dalapon, tiazafluron, tiazopir, tiafenacil, tiencarbazona, thiencarbazona-metilo, tiocarbazil, tioclorim, tiobencarb, tidiazimin, tidiazuron, tifensulfuron, thifensulfuronmetilo, desmedifam, desmetrina, tetrafluron, thenilclor, tebutam, tebutiuron, terbumeton, tepraloxidim, tefuriltriona, tembotriona, delaclor, terbacil, terbucarb, terbuclor, terbutilazina, terbutrina, topramezona, tralkoxidim, triaziflam, triasulfuron, triafamona, trialato, trietazina, tricamba, triclopir, tridifano, tritac, tritosulfuron, trifludimoxazin, triflusulfuron, triflusulfuron-motilo, trifluralin, trifloxisulfuron, IF-2020-86290883-APN-ANP#INPI 109 Página 109 de 122 tripropindan, tribenuron-metilo, tribenuron, trifop, trifopsima, trimeturon, tolpiralato, naptalam, naproanilida, napropamida, nicosulfuron, nitralin, nitrofeno, nitrofluorfeno, nipiraclofeno, neburon, norflurazon, noruron, barban, paclobutrazol, paraquat, parafluron, haloxidina, halauxifeno, haloxifop, haloxifop-P, haloxifop-metiio, halosafeno, halosulfuron, halosulfuron-metilo, picloram, picolinafeno, biciclopirona, ispiribac, bispiribac-sodio, pidanon, pinoxaden, bifenox, piperofos, himexazol, piraclonil, pirasulfotol, pirazoxifeno, pirazosulfuron, pirazosulfuron-etilo, pirazolato, bilanafos, piraflufenetilo, piriclor, piridafol, piritiobac, piritiobac-sodio, piridato, piriftalid, piributicarb, piribenzoxim, pirimisulfan, primisulfuron, pirirninobac-metilo, piroxasulfona, piroxsulam, fenasulam, fenisofam, fenuron, fenoxasulfona, fenoxaprop, fenoxaprop-P, fenoxaprop-etilo, fenotiol, fenoprop, fenobenzuron, fenquinotriona, fentiaprop, fenteracol, fer.trazamida, fenmedifam, fenmedifam-etilo, butaclor, butafenacil, butamifos, butiuron, butidazol, butilato, buturon, butenaclor, butroxidim, butralina, flazasulfuron, flamprop, furiloxifeno, prinaclor, primisulfuron-metilo, fluazifop, fluazifop-P, fluazifop-butilo, fluazolato, fluroxipir, fluotiuron, fluometuron, fluoroglicofeno, flurocloridona, fluorodifeno, fluoronitrofeno, fluoromidina, flucarbazona, flucarbazona-sedio, flucloralin, flucetosulfuron, fluthiacet, flutiacet-metilo, flupirsulfuron, flufenacet, flufenican, flufenpir, flupropacil, flupropanato, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentil, flumipropin, flumezin, fluometuron, flumetsulam, fluridona, flurtamona, fluroxipir, pretilaclor, proxan, proglinazina, prociazina, prodiamina, prosulfalin,. IF-2020-86290883-APN-ANP#INPI 110 Página 110 de 122 prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, prcp.i zamida, propisoclor, prohidrojasmon, propirisulfuron, profam, profluazol, profiuralina, pro'nexadiona-calcium, propox: carbazona, propoxycarbazona-sodium, profoxidim, romacil, brompirazon, prometrin, prometen, bromoxinil, bromofenoxim, bromobutida, bromobonil, florasulam, florpirauxifono, hexacloroacetona, hexazinona, petoxamid, benazolin, penoxsulam, pebulato, beflubutamid, vernolate, perfluidona, bencarbazona, benzadox, benzipram, bencilaminopurina, benzLiazuron, benzfendizona, bensulida, bensulfuron-methylo, benzoilprop, benzoblciclon, bonzofenap, benzofluor, bentazona, pentanoclor, bentiocarb, pendimetai.in, pentoxazona, benfluraline, benfuresate, phesamine, fomesafeno, foramsulfaron, forclorfenuron, hidrazida malenca, mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, metopro trine, meta za cl.or, metazol, metazosulfuron, metabenztiazuron, metamitron, metamifop, inetam, mctalpropalin, metiuron, methiazoline, methiobencarb, methyldimron, methoxuron, metosulam, metsulfuron, metsulfuron-methyl, mctflurazon, metobromuron, metobenzuron, metometon, meto.lacl.cr, metribuzin, mepxquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methylsodium, iodobonil, iodomethane, lactofeno, linuron, rimsulfuron, lenacil, rodetanil, calcium peroxide, methyl bromide or similar.

[0147] Furthermore, as biological agrochemicals, the same effect can be achieved by using them mixed with the following biological agrochemicals, for example: IF-2020-86290883-APN-ANP#INPI 111 Page 111 of 122 formulations of viruses such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), entomopox virus (EPV) or similar; microbial agrochemicals known as insecticidal or nematocidal agents such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteurella penetrans or similar; microbial agrochemicals used as fungicidal agents such as Trichoderma lignorum, radiobactor Agrobacterium, non-pathogenic Erwinia carotovora, Bacillus subtilis or similar; and biological agrochemicals used as herbicides such as Xanthomonas campestris or similar.

[0148] In addition, it is used in conjunction with biological agrochemicals such as, for example, natural enemies, such as the Encarsia wasp (Encarsia Formosa), colemani wasp (Aphidius colemani), aphid fly (Aphidoletes aphidimyza), warm-climate leafminer parasite (Diglyphus isaea), leafminer parasite (Dacnusa sibirica), Persimilis (Phytoseiulus persimilis), springtails (Amblyseius cucumeris), anthocorid predatory insect (Orius sauteri) or similar; microbial agrochemicals such as Beauveria brongniartii are also possible; and pheromone agents such as (Z)-10-tetradecenyl = acetate, (E, Z)-4,10-tetradecadienyl = acetate, (Z)-8-dodecenyl = acetate, (Z)-11-tetradecenyl = acetate, (Z)-13-icocene-10-one, 14-methyl-l-octadecene or the like

[0149] Representative examples of the present invention are repeated, but the present invention is not limited to them. IF-2020-86290883-APN-ANP#INPI 112 Page 112 of 122 Examples

[0150] Production Example 1 Production of N-methyl-N-(4-[5-(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]benzyl methanesulfonamide (Compound No. 1-1) [Chemical formula 21] N-methyl-NN-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol3-yl]benzyl]methanesulfone amide (0.30 g, 0.90 mmol) prepared by the method described in WO 2017 / 213252 was dissolved in methanol (10 mL), cooled to 0°C, sodium borohydride (0.017 g, 0.45 mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. Subsequently, 1 mL of acetone was added, and the mixture was stirred at room temperature for 15 minutes. Silica gel was added, and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.23 g, 0.67 mmol). Yield: 75% Physical property: melting point 160-161°C

[0151] Production Example 2 Production of N-methyl-N-{4-[4-methyl-5(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3yl]bcnylJmetansulfonamide (Compound No. 1-13) [Chemical Formula 22] IF-2020-86290883-APN-ANP#INPI 113 Page 113 of 122 N-methyl-N-{4-[5-(trifluoromet.yl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]benzyl) methanesulfonamide (0.060 g, 0.118 mmol) was dissolved in DMA (3 mL), cesium carbonate (0.087 g, 0.27 mmol) and methyl iodide (0.038 g, 0.27 mmol) were added at room temperature, and the mixture was stirred at room temperature for 3.4 hours. It was cooled to 0°C, deactivated with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.046 g, 0.13 mmol). Yield: 73% Physical property: 107-109oC

[0152] Production Example 3 Production of N-methyl-N-{4-[5-methyl-5(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]benzyl)butylamide (Compound No. 1-12) N-methyl-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl-butylaraide (0.12 g, 0.36 mmol) prepared by the method described in document WO 2017 / 055469 IF-2020-86290883-APN-ANP#INPI 114 Page 114 of 122. The compound was dissolved in dry THF (3 mL) under an argon atmosphere, cooled to 0°C, and methylmagnesium bromide (3.0 M in Et₂O) (0.18 mL, 0.55 mmol) was added. The mixture was stirred at room temperature for 1.7 hours. After this, a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic compound was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.077 g, 0.22 mmol). Yield: 62¾ Physical property: melting point 161-163°C

[0153] Example reference i Production of 5-chloro-l-{4-[5-(trifluoromethyl)1,2,4-oxadiazol-3-yl]benzyl[pyridin-2(1H)-one [Chemical formula 24] 3-[4-(Bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.25 g, 0.81 mmol) prepared by the method described in WO 2017 / 118689 was dissolved in DMA (2 mL) and potassium carbonate (0.17 g, 1.21 mmol) and 5-chloro-2-hydroxypyridine (0.125 g, 0.97 mmol) were added at room temperature and stirred for 1.5 hours at 100°C. It was cooled to 0°C, deactivated with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was IF-2020-86290883-APN-ANP#INPI 115 Page 115 of 122 purified by silica gel column chromatography to obtain the title compound (0.112 g, 0.32 mmol). Yield: 39%

[0154] Reference example 2 Production of (Z)-N'-hydroxy-4-iodobenzimidate [Chemical formula 25] 4-Iodobenzonitrile (11 g, 64 mmol) was dissolved in 70 mL of ethanol, sodium acetate (5.6 g, 68 mmol), and hydroxylamine hydrochloride (4.7 g, 68 mmol), and the mixture was stirred for 4 hours while heating under reflux. The ethanol was then removed, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The precipitated solid was washed with ethyl acetate:hexane (10:1). To remove the ethyl acetate, the resulting solid was dried under reduced pressure at 40°C for 1 hour using a sample dryer and allowed to stand for 1 day to obtain the title compound (12 g) as the crude product. Yield: Quantitative

[0155] Reference example 3 Production of 3-(4-iodophenyl)-5-(trifluoromethyl)1,2,4-oxadiazole [Chemical formula 26] IF-2020-86290883-APN-ANP#INPI 116 Page 116 of 122 (Z)-N'-hydroxy-4-iodobenzimidate (12 g, 45 mmol) was dissolved in 100 mL of chloroform, pyridine (14 g, 180 mmol) and trifluoroacetic anhydride (19 g, 90 mmol) were added, and the mixture was stirred for 5 hours at room temperature. Water was then added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (11 g, 31 mmol). Yield: 43% Physical property: Melting point 73-75°C

[0156] Reference example 4 Production of N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}butylamide [Chemical formula 27] 3-(4-Iodophenyl)-5-(trifluoromethyl)1,2,4-oxadiazole (0.31 g, 0.90 mmol) was dissolved in 8 mL of toluene, and cesium carbonate (0.44 g, 1.4 mmol), n-butylamide (0.094 g, 1.1 mmol), xanthophos (0.16 g, 0.27 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.084 g, 0.090 mmol) were added at room temperature. The mixture was heated under reflux for 2.5 hours. The residue was purified by silica gel column chromatography to obtain the title compound (0.19 g, 0.62 IF-2020-86290883-APN-ANP#INPI 117 Page 117 of 122 mmol). Yield: 69%. Physical property value: Melting point 112-115 C

[0157] The following lists examples of the present inventive formulations. In the formulation examples, the term "parts" indicates parts by weight.

[0158] Example of formulation 1. The compound of the present invention is represented by the general formula (I) 10 parts Xylene N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts An emulsifiable concentrate was prepared by mixing and uniformly dissolving the above ingredients.

[0159] Example formulation 2. The compound of the present invention is represented by the general formula (I) 3 parts Clay powder 02 parts Diatomaceous earth powder 15 parts A powder was prepared by uniformly mixing and grinding the above ingredients.

[0160] Example formulation 3. The compound of the present invention is represented by the general formula (I) 5 parts Mixed bentonite and clay powder 90 parts Calcium lignin sulfonate 5 parts The granules were prepared by mixing the above ingredients evenly together with a IF-2020-86290883-APN-ANP#INPI 118 Page 118 of 122: Adding the appropriate amount of water and kneading the resulting mixture, followed by granulation and drying.

[0161] Example of formulation 4. The compound of the present invention is represented by the general formula (I) 20 parts Mixture of kaolin and synthetic high dispersion silicic acid Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts A wettable powder was prepared by uniformly mixing and grinding the above ingredients.

[0162] Example test 1. Fungicide efficacy test for soybean rust A chemical agent prepared according to Formulation Examples 1 to 4, containing the compound of the present invention represented by general formula (I) as the active ingredient, was diluted with water to a predetermined concentration. Soybeans (cultivar: Enrei, 2-leaf stage) grown in 6 cm diameter pots were sprayed on the foliage at a rate of 10 ml per pot. After air-drying the solution, the spore suspension prepared from soybean leaves infected with soybean rust (Phakopsora pachyrhizi) was inoculated by spraying, maintained under humidified conditions at 20°C for 24 hours, and then transferred to a greenhouse for approximately 10 days. For the evaluation, several area relationships with disease were evaluated to calculate the control value of the following formula 1.

[0163] IF-2020-86290883-APN-ANP#INPI 119 Page 119 of 122 [Formula 1] Control vater (%) UflacíAn Λ* ár<*A di* injury nnvrrrim t»n wirn» nn tiaiadó- RMACiAn di» ήιτΛ d<* ti» <i<An nmnw»rtm κη Average lesion area ratio in untreated leriene *100 Evaluation criteria 0 : Control value 9% or lower 1 : Control value 10-19% 2 : Control value 20-29% 3 : Control value 30-39% 4 : Control value 40-49% 5 : Control value 50-59% 6 : Control value 60-69% 7 : Control value 70-79% 8 : Control value 80-89% 9 : Control value 90-99% 10 : Control value 100%

[0164] As a result of the aforementioned test, of the present inventive compounds represented by the general formula (I), the following compounds showed, at a treatment concentration of 50 ppm, an effect with a control value of 8 or more: 1-1, 1-5, 1-9, 1-10, 1-11, 1-12, 1-14, 1-15, 1-19, 1-23, 1-27, 1-28, 1-31, 1-35, 1-39, 1-40, 1-43, 1-47, 1-53, 1-54, 1-55, 1-56, 1-58, 1-63, 1-64, 1-65, 1-69, 1-73, 1-74, 1-76, 1-80, 1-81, 1-82, 1-90, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-8, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 2-18, 2-20, 2-21, 2-22, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-28 3-29, 3-30, 3-32, 3-35, 3-36, 3-38, 3-39, 3-40, 3-41, 3-42, 3-43, 3-44, 3-45, 3-46, 3-53, 3-55, 4-3, 5-3, 6-3, 6-6 and 6-9.

[0165] IF-2020-86290883-APN-ANP#INPI 120 Page 120 of 122 Example test 4. HDAC4 inhibitory activity measurement test <objetivo> The HDAC inhibitory activity of the present compounds is evaluated in comparison with known compounds. <Matoriales y Métodos (Ensayo compuesto y concentración)> The test substances were diluted with distilled water, and the concentration was established as follows: each compound had a maximum concentration of 37.5 μM, and a total of six concentrations were provided in a common ratio of 3 (0.2, 0.5, 1.4, 4.2, 12.5, 37.5 μM). The positive control agent, Tricostatin A, was tested at a maximum concentration of 25 μM with reference to the package insert, and a total of four concentrations were evaluated in a common ratio of 5 (0.2, 1.0, 5.0, 25 μM). Distilled water was added to the solvent control instead of the test substances. (0166] The fluorogenic HDAC4 assay kit (BPS Bioscience, Cat. 50064) was used to measure HDAC4 inhibitory activity. The specified amounts of HDAC substrate, assay buffer, recombinant human HDAC4 enzyme, and BSA (1 mg / ml) provided in the kit were mixed and aliquoted into 96-well microplates. After adding a test substance solution (distilled water for solvent control), the mixture was incubated at 37°C for 30 minutes. After adding 2x HDAC Developer and incubating for 15 minutes at room temperature, the fluorescence intensity was measured using a microplate reader (Em: 355, Ex: 450). The relationship with the IF-2020-86290883-APN-ANP#INPI 121 Page 121 of 122 Solvent control (percentage of control activity) was determined as the relative activity, and the relative activity at each concentration was used to calculate the inhibitory concentration of 50¾ (IC50) by logistic regression analysis.

[0167] <resultado> The compounds of the present invention were found to have an IC50 of 36.8 or more, and were found to have lower HDAC4 inhibitory activity. [Industrial applicability]

[0168] The compound of the present invention represented by the general formula (I) or salts thereof has a notable effect as an agro-horticultural fungicide. IF-2020-86290883-APN-ANP#INPI 122 Page 122 of 122 Argentine Republic - National Executive Branch 2020 - Year of General Manuel Belgrano Additional Signature Sheet Graphic Report Number: IF-2020-86290883-APN-ANP#INPI CITY OF BUENOS AIRES Friday, December 11, 2020 Reference: 20190102241 The document was imported by the GEDO system with a total of 122 page(s). Digitally signed by Electronic Document Management Date: 2020.12.11 15:52:33-03:00 Mariela Flavia Gonnet Administrative Advisor National Patent Administration National Institute of Industrial Property Digitally signed by Electronic Document Management Date: 2020.12.11 15:52:35-03:00< / resultado> < / objetivo> < / s>

Claims

1. A compound represented by the general formula (I) or salts thereof: [Chemical Formula 1] (FORMULA I) characterized in that, A indicates a single bond or the following structure A1; A2; A3; A4; A5; A6 or A7: [Chemical Formula 2] (FORMULA II); B indicates a single bond; oxygen atom; C(R1)(R2) or carbonyl group. Y indicates a single bond; oxygen atom; C(R1)(R2) or N(R3). R1 ​​and R2 each independently indicate (a1) a hydrogen atom; (a2) a halogen atom; or (a3) ​​a (C1-6) alkyl group; (a4) a (C1-6) alkoxy group; or (a5) a (C1-6) haloalkyl group; R1 and R2 can form a cyclopropyl group with a carbon atom to which they are attached. R3 indicates (b1) a hydrogen atom; (b2) an alkyl group (C1-6); (b3) an alkoxy group (C1-6); (b4) a cycloalkyl group (C3-6); (b5) an alkylcarbonyl group (C1-6); (b6) an alkoxycarbonyl group (C1-6); (b7) an alkenyl group (C2-6); (b8) an alkynyl group (C2-6);or (b9) a cycloalkyl (C3-6) alkyl (C1-6) group. Q indicates (c1) a hydrogen atom; (c2) an alkyl (C1-6) group; (c3) an alkenyl (C2-6) group; (c4) an alkynyl (C2-6) group; (c5) a cycloalkyl (C3-6) group; (c6) an alkoxy (C1-6) group; (c7) a haloalkyl (C1-6) group; (c8) a haloalkenyl (C2-6) group; (c9) a haloalkynyl (C2-6) group; (c10) a halocycloalkyl (C3-8) group; (c11) a haloalkoxy (C1-6) group;(c12) a group R a (R b )N (where R a and R b each independently denote a hydrogen atom, alkyl (C1-6) group, alkenyl (C2-6) group, alkynyl (C2-6) group, cycloalkyl (C3-6) group, alkoxy (C1-6) group, haloalkyl (C1-6) group, cycloalkyl (C3-6) group, phenyl group, alkoxy (C1-6) group, dialkoxy (C1-6) group, cyanoalkyl (C1-6) group, alkylthio (C1-6) group, dialkylamino (C1-6) group, alkylcarbonyl (C1-6) group, alkoxycarbonyl (C1-6) group, phenylcarbonyl group or group benzyl); (c13) an aryl group;(c14) an aryl group each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-6) alkyl group, (C1-6) alkoxy group, (C3-6) cycloalkyl group, (C1-6) haloalkyl group, (C1-6) haloalkoxy group, (C3-6) halocycloalkyl group, (C1-6) alkylthio group, (C1-6) alkylsulfinyl group, (C1-6) alkylsulfonyl group, (C1-6) haloalkylthio group, (C1-6) haloalkylsulfinyl group, (C1-6) haloalkylsulfonyl group, (C1-6) R a (R b )N group (where R a and R b are the same as above), (C1-6) alkoxycarbonyl group, and (R a (R b )Ncarbonyl group (where R a and R b are the same as the above); (c15) a hetero ring of 5 to 6 members or a fused hetero ring of 8 to 10 members;(c16) a 5- to 6-membered hetero ring or fused 8- to 10-membered hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-6) alkyl group, (C1-6) alkoxy group, (C3-6) cycloalkyl group, (C1-6) haloalkyl group, (C1-6) haloalkoxy group, (C3-6) halocycloalkyl group, (C1-6) alkylthio group, (C1-6) alkylsulfinyl group, (C1-6) alkylsulfonyl group, (C1-6) haloalkylthio group, (C1-6) haloalkylsulfinyl group, (C1-6) haloalkylsulfonyl group, (C1-6) haloalkylthio group, (C1-6) haloalkylsulfinyl group, (C1-6) haloalkylsulfonyl group, (C1-6) R a (R b )N group (where R a and R b are the same as above), (C1-6) alkylthio group (C1-6), phenyl group, halogen-substituted phenoxy group, (C1-6) alkoxycarbonyl group and R a (R b )Ncarbonyl group (where R a and R b are the same as above); (c17) an (C1-6) arylalkyl group;(c18) an arylalkyl (C1-6) group each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, alkyl (C1-6) group, alkoxy (C1-6) group, cycloalkyl (C3-6) group, haloalkyl (C1-6) group, haloalkoxy (C1-6) group, halocycloalkyl (C3-6) group, alkylthio (C1-6) group, alkylsulfinyl (C1-6) group, alkylsulfonyl (C1-6) group, haloalkylthio (C1-6) group, haloalkylsulfinyl (C1-6) group, haloalkylsulfonyl (C1-6) group, R a (R b )N group (where R a and R b are the same as above), alkoxycarbonyl (C1-6) group, and R a (R b )Ncarbonyl group (where R a and R b are the same as above); (c19) an alkyl group (C 1-6 ) of a 5- to 6-membered hetero ring or fused hetero ring of 8 to 10 members;(c20) a 5- to 6-membered hetero ring (C1-6) alkyl group or 8- to 10-membered fused hetero ring each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-6) alkyl group, (C1-6) alkoxy group, (C3-6) cycloalkyl group, (C1-6) haloalkyl group, (C1-6) haloalkoxy group, (C3-6) halocycloalkyl group, (C1-6) alkylthio group, (C1-6) alkylsulfinyl group, (C1-6) alkylsulfonyl group, (C1-6) haloalkylthio group, (C1-6) haloalkylsulfinyl group, (C1-6) haloalkylsulfonyl group, (C1-6) haloalkylthio group, (C1-6) haloalkylsulfinyl group, (C1-6) haloalkylsulfonyl group, (C1-6) R a (R b )N group (where R a and R b are the same as above), alkylthio group (C1-6) alkyl (C1-6), phenyl group, halogen-substituted phenoxy group, (C1-6) alkoxycarbonyl group and R a (R b )Ncarbonyl group (where R a and R b are the same as the above);(c21) an alkyl (C1-6) group each independently having in the chain 1 to 3 substituents selected from the group consisting of a cyano group, alkoxy (C1-6) group, R a (R b )N group (where R a and R b are the same as above), alkylthio (C1-6) group, alkylsulfinyl (C1-6) group, and alkylsulfonyl (C1-6) group; (c22) an R c ON=C(R d )NH group (where R and R d each independently denote a hydrogen atom or alkyl (C1-6) group); or (c23) a 3-ethoxyiminoazetidin-1-yl group. R 5 denotes (d1) a hydrogen atom; (d2) an alkyl (C1-6) group; (d3) an alkylcarbonyl (C1-6) group; (d4) an alkoxycarbonyl (C1-6) group; or (d5) a benzyl group. R6 indicates (e1) a hydrogen atom. X1, X2, X3, and X4 each independently indicate (f1) a hydrogen atom; (f2) a halogen atom; (f3) a cyano group; (f4) a nitro group; (f5) a (C1-6) alkyl group; (f6) a (C3-6) cycloalkyl group; (f7) a (C1-6) alkoxy group;(f8) a (C1-6) haloalkyl group; (f9) a (C1-6) haloalkoxy group; (f10) a (C3-6) halocycloalkyl group; (f11) a (C1-6) alkylthio group; (f12) a (C1-6) alkylsulfinyl group; (f13) a (C1-6) alkylsulfonyl group; (f14) a (C1-6) haloalkylthio group; (f15) a (C1-6) haloalkylsulfinyl group; or (f16) a (C1-6) haloalkylsulfonyl group. 5 Claims follow;