TW201837025A - Novel dithiolane compound or a salt or an n-oxide and use thereof - Google Patents

Abstract

An object of the present invention is to provide a dithiolane compound or a salt or an N-oxide thereof that controls diseases. The present invention provides a dithiolane compound represented by Formula (1):, or a salt or an N-oxide thereof, wherein R1 represents hydrogen, halogen, C1-6 alkyl or a substituent as defined herein; R2 represents hydrogen, halogen, C1-6 alkyl or a substituent as defined herein; R3 represents hydrogen, halogen, C1-6 alkyl or a substituent as defined herein; Y1 represents optionally substituted aryl, optionally substituted pyridyl or a substituent as defined herein; Y2 represents optionally substituted aryl, optionally substituted pyridyl or a substituent as defined herein; Q represents cyano or a substituent as defined herein.

Description

Novel dithiazide compound or salt thereof or N-oxide thereof and use thereof

The present invention relates to a novel dithiazide compound or a salt thereof or an N-oxide thereof and a process for the preparation thereof. The invention further provides agricultural and horticultural fungicide compositions comprising the compounds.

In recent years, in order to protect plants from diseases caused by fungi, various known fungicides are being used. However, resistance to various fungi has been observed due to the long-term and extensive use of such fungicides. Therefore, the control of resistant fungi cannot be accomplished by using known fungicides. Therefore, there is a need in the industry to develop novel compounds having fungicidal activity against drug resistant fungi. WO 2015/003991 (Patent Document (PTL) 1) discloses a compound represented by the formula (A): Wherein X is O, S or NR ⁴ ; Y and Z are independently O, S, NR ⁵ or C(R ⁶ R ⁷ ); A is hydrogen, alkyl, haloalkyl, cycloalkyl, halogen ring An alkyl group, an aryl group, a heteroaryl group, various electron withdrawing groups such as a nitro group, a cyano group, an ethyl fluorenyl group, a carboxyl group or the like; a Q-based alkyl group, a halogenated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, Heterocyclic group or the like; R ¹ , R ² and R ^{3 are} independently hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _3-7 cycloalkyl, C _1-6 alkoxy , C _1-6 haloalkoxy or optionally substituted phenyl. The publication also mentions that the compound represented by the formula (A) can be used as a fungicide for controlling plant diseases. Patent documents WO 2015/162271 (PTL 2) and WO 2015/162269 (PTL 3) also disclose imidazole-substituted compounds represented by formula (B): Wherein X and Y are independently O, S or NR ⁵ ; R ¹ , R ² and R ^{4 are} independently hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 ring An alkyl group, a C _1-6 alkoxy group, a C _1-6 haloalkoxy group; an R ³ -based phenyl group substituted with at least one substituent R ⁶ or an aromatic 5-membered heterocyclic ring; and R ⁵ is hydrogen, C _{1 -6} alkyl, C _1-6 alkoxy or C _1-6 cycloalkyl. The publications also mention that the compound represented by the formula (B) can be used as a fungicide for controlling plant diseases. However, the publications do not disclose the compounds of the invention. Another patent document WO 2015/162268 (Patent Document (PTL) 4) also discloses an imidazole-substituted compound represented by formula (C): Wherein X and Y are independently O, S or NR ⁴ ; R ¹ , R ² and R ^{3 are} independently hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkane Oxyl, C _1-6 haloalkoxy; Z ¹ , Z ² , Z ³ , Z ⁴ and Z ^{5 are} independently CR ⁵ or N. The publication also mentions that the compound represented by the formula (C) can be used as a fungicide for controlling plant diseases. However, this publication does not disclose the compounds of the present invention. Citation List Patent Literature PTL 1: WO 2015/003991 PTL 2: WO 2015/162271 PTL 3: WO 2015/162269 PTL 4: WO 2015/162268

Solution to Problem The present invention provides a novel dithiazinium compound or a salt thereof or an N-oxide thereof which exhibits excellent fungicidal activity against drug-resistant fungi and drug-sensitive fungi. The invention also provides a process for the preparation of the dithiazide compound or a salt thereof or an N-oxide thereof. The present invention further provides novel fungicides for use in agriculture and horticulture that exhibit significant fungicidal effects against chemical resistant fungi as well as chemically sensitive fungi. Specifically, the inventors conducted extensive research and successfully synthesized a compound represented by the formula (1) or a salt thereof or an N-oxide thereof having fungicidal activity. The inventors have conducted further research based on the above findings. The present invention has thus been completed. More specifically, the present invention includes the following examples: Item 1: A dithiazide compound represented by the formula (1): Or a salt thereof or an N-oxide thereof, wherein R ¹ , R ² and R ^{3 are the} same or different and each represents hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkane Oxy, C _1-6 haloalkoxy, C _1-6 alkoxy C _1-6 alkyl, C _1-6 haloalkoxy C _1-6 alkyl, C _2-6 alkenyl, C _2-6 Haloalkenyl, C _2-6 alkynyl, C _2-6 haloalkynyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, optionally substituted aryl And optionally substituted heteroaryl or optionally substituted heterocyclic group, the two of the R ¹ , R ² and R ³ groups together may form a ring via or without at least one hetero atom, denoted as R ¹ The groups of R ² and R ³ may be further substituted as appropriate; Y ¹ represents an optionally substituted aryl group, optionally substituted pyridyl group, optionally substituted pyrazinyl group, optionally substituted pyrimidinyl group Or optionally substituted pyridazinyl; Y ² represents an optionally substituted aryl or optionally substituted heteroaryl; and Q represents hydrogen, nitro, cyano, C _1-6 alkyl, C _{1 -6} haloalkyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, C _1-6 alkylcarbonyl, C _1-6 haloalkyl Carbonyl group, C _3-8 cycloalkylcarbonyl, C _1-6 alkoxycarbonyl, C _1-6 haloalkoxycarbonyl group, C _3-8 cycloalkoxy-carbonyl, C _1-6 alkoxy -alkylthio, C _{1 -6} haloalkylthio, C _3-8 cycloalkylthio, C _3-8 cycloalkyl C _1-6 alkylthio, C _1-6 alkoxy C _1-6 alkylthio, C _{1- 6} alkylsulfonyl, C _1-6 alkylsulfinylene, C _1-6 haloalkylsulfonyl, C _1-6 haloalkylsulfinyl, C _3-8 cycloalkylsulfonyl, C _3-8 cycloalkylsulfinyl, C _3-8 cycloalkyl C _1-6 alkylsulfonyl, C _3-8 cycloalkyl C _1-6 alkylsulfinylene, optionally Substituted arylthio, optionally substituted aryl C _1-6 alkylthio, optionally substituted arylsulfonyl, optionally substituted arylsulfinyl, optionally substituted a heteroaryl group or a optionally substituted heterocyclic group which is optionally substituted. Item 2: The thiazide compound according to item 1 or a salt thereof or an N-oxide thereof, wherein R ¹ , R ² and R ^{3 are the} same or different and each represents hydrogen, halogen or C _1-6 alkyl. Item 3: The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein R ¹ , R ² and R ^{3 are the} same or different and each represents hydrogen or a C _1-6 alkyl group. Item 4: The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ¹ is optionally substituted aryl or optionally substituted pyridyl. Item 5: A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ¹ is a benzene ring represented by Y ^1a : Wherein R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are the} same or different and each represents hydrogen, halogen, nitro, cyano, hydroxy, formamyl, optionally substituted amine, C _{1- 6} alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkoxy C _1-6 alkyl, C _1-6 haloalkoxy C _{1 -6} alkyl, C _1-6 alkoxycarbonyl, C _1-6 haloalkoxycarbonyl, cyano C _1-6 alkyl, cyano C _1-6 alkoxy, C _2-6 alkenyl, C _2-6 haloalkenyl, cyano C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 haloalkynyl, cyano C _2-6 alkynyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, C _1-6 alkylthio, C _1-6 haloalkylthio, C _3-8 cycloalkylthio, C _3-8 cycloalkyl C _{1 -6} alkylthio, C _1-6 alkoxy C _1-6 alkylthio, C _1-6 alkylsulfonyl, C _1-6 alkylsulfinyl, C _1-6 haloalkylsulfonate , C _1-6 haloalkylsulfinyl, C _3-8 cycloalkylsulfonyl, C _3-8 cycloalkylsulfinyl, C _3-8 cycloalkyl, C _1-6 alkyl sulfo acyl, C _3-8 cycloalkyl C _1-6 alkylsulfinyl acyl, C _C2-6 alkenyloxy, C _C2-6 alkynyl group, C _C2-6 haloalkenyl group, C _2-6 haloalkynyloxy, C _1-6 alkylsulfonyloxy, C _1-6 alkylsulfinyloxy, C _1-6 alkylcarbonyl, C _1-6 haloalkylcarbonyl, carboxyl, OCN, SCN, SF ₅ , An optionally substituted aryloxy group, optionally substituted aryl C _1-6 alkoxy group, optionally substituted arylthio group, optionally substituted aryl C _1-6 alkylthio group, optionally Substituted arylsulfonyl, optionally substituted arylsulfinyl, optionally substituted heteroaryloxy, optionally substituted arylsulfonyloxy, optionally substituted An arylsulfinyloxy group, an optionally substituted aryl group, an optionally substituted heteroaryl group or an optionally substituted heterocyclic group; and a linkage point of the * to the parent compound. Item 6: The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are the} same or different and each represents hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy or C _1-6 haloalkoxy. Item 7: A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ¹ is optionally substituted 4-pyridyl, optionally substituted 3-pyridyl or 2-pyridyl group substituted. Item 8: The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ¹ is a pyridine ring represented by any one of Y ^1b , Y ^1c and Y ^1d : Wherein R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ^{20 are the} same or different and each represents hydrogen, halogen, nitro , cyano, hydroxy, formamidine, optionally substituted amino, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _{1 -6} alkoxy C _1-6 alkyl, C _1-6 haloalkoxy C _1-6 alkyl, C _1-6 alkoxycarbonyl, C _1-6 haloalkoxycarbonyl, cyano C _1-6 Alkyl, cyano C _1-6 alkoxy, C _2-6 alkenyl, C _2-6 haloalkenyl, cyano C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 halo Alkynyl, cyano C _2-6 alkynyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, C _1-6 alkylthio, C _1-6 haloalkyl sulphide , C _3-8 cycloalkylthio, C _3-8 cycloalkyl C _1-6 alkylthio, C _1-6 alkoxy C _1-6 alkylthio, C _1-6 alkylsulfonyl , C _1-6 alkylsulfinyl, C _1-6 haloalkylsulfonyl, C _1-6 haloalkylsulfinyl, C _3-8 cycloalkylsulfonyl, C _3-8 ring Alkylsulfinyl, C _3-8 cycloalkyl, C _1-6 alkylsulfonyl, C _3-8 cycloalkyl C _1-6 alkyl sulfinylene, C _2-6 alkenyloxy , C _2-6 alkynyl Alkoxy, C haloalkoxy _C2-6 alkenyloxy, C _C2-6 haloalkynyl group, C _1-6 alkyl sulfonic acyl group, C _1-6 alkylsulfinyl acyl group, C _1-6 alkylcarbonyl, C _1-6 haloalkylcarbonyl, carboxyl, OCN, SCN, SF ₅ , optionally substituted aryloxy, optionally substituted aryl C _1-6 alkoxy, optionally Substituted arylthio, optionally substituted aryl C _1-6 alkylthio, optionally substituted arylsulfonyl, optionally substituted arylsulfinyl, optionally substituted Heteroaryloxy, optionally substituted arylsulfonyloxy, optionally substituted arylsulfinyloxy, optionally substituted aryl, optionally substituted heteroaryl Or a heterocyclic group which is optionally substituted; and * is the point of attachment to the parent compound. Item 9. The dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ^{20 are the} same or different and each represents hydrogen or halogen. Item 10: A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ¹ represents: , where * is the point of attachment to the parent compound. Item 11: A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ¹ represents: , where * is the point of attachment to the parent compound. Item 12: A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ¹ represents: , where * is the point of attachment to the parent compound. Item 13. The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is an optionally substituted aryl group. Item 14: The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is a benzene ring represented by Y ^2a : Wherein R ²¹ , R ²² , R ²³ , R ²⁴ and R ^{25 are the} same or different and each represents hydrogen, halogen, nitro, cyano, hydroxy, formamyl, optionally substituted amine, C _{1- 6} alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkoxy C _1-6 alkyl, C _1-6 haloalkoxy C _{1 -6} alkyl, C _1-6 alkoxycarbonyl, C _1-6 haloalkoxycarbonyl, cyano C _1-6 alkyl, cyano C _1-6 alkoxy, C _2-6 alkenyl, C _2-6 haloalkenyl, cyano C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 haloalkynyl, cyano C _2-6 alkynyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, C _1-6 alkylthio, C _1-6 haloalkylthio, C _3-8 cycloalkylthio, C _3-8 cycloalkyl C _{1 -6} alkylthio, C _1-6 alkoxy C _1-6 alkylthio, C _1-6 alkylsulfonyl, C _1-6 alkylsulfinyl, C _1-6 haloalkylsulfonate , C _1-6 haloalkylsulfinyl, C _3-8 cycloalkylsulfonyl, C _3-8 cycloalkylsulfinyl, C _3-8 cycloalkyl, C _1-6 alkyl sulfo acyl, C _3-8 cycloalkyl C _1-6 alkylsulfinyl acyl, C _C2-6 alkenyloxy, C _C2-6 alkynyl group, C _C2-6 haloalkenyl group, C _2-6 haloalkynyl oxygen , C _1-6 alkyl sulfonic acyl group, C _1-6 alkylsulfinyl acyl group, C _1-6 alkylcarbonyl, C _1-6 haloalkylcarbonyl group, a carboxyl group, OCN, SCN, SF ₅ An optionally substituted aryloxy group, optionally substituted aryl C _1-6 alkoxy group, optionally substituted arylthio group, optionally substituted aryl C _1-6 alkylthio group, Optionally substituted arylsulfonyl, optionally substituted arylsulfinyl, optionally substituted heteroaryloxy, optionally substituted arylsulfonyloxy, optionally Substituted arylsulfinyloxy, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted heterocyclyl; and * is the point of attachment to the parent compound. Item 15. The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein R ²¹ , R ²² , R ²³ , R ²⁴ and R ^{25 are the} same or different and each represents hydrogen or halogen , nitro, cyano, optionally substituted amino, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy or, as appropriate, substituted Aryl. Item 16. The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is optionally substituted heteroaryl. Item 17. A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is optionally substituted pyridyl, optionally substituted pyrazinyl, optionally substituted Pyrimidyl, optionally substituted pyridazinyl or optionally substituted thiazolyl. Item 18. A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is optionally substituted pyridyl, optionally substituted pyrazinyl or optionally substituted Thiazolyl. Item 19. The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is optionally substituted pyridyl. Item 20: A dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is optionally substituted 4-pyridyl, optionally substituted 3-pyridyl or 2-pyridyl group substituted. Item: The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein Y ² is a pyridine ring represented by any one of Y ^2b , Y ^2c and Y ^2d : Wherein R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ and R ^{37 are the} same or different and each represents hydrogen, halogen, nitro , cyano, hydroxy, formamidine, optionally substituted amino, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _{1 -6} alkoxy C _1-6 alkyl, C _1-6 haloalkoxy C _1-6 alkyl, C _1-6 alkoxycarbonyl, C _1-6 haloalkoxycarbonyl, cyano C _1-6 Alkyl, cyano C _1-6 alkoxy, C _2-6 alkenyl, C _2-6 haloalkenyl, cyano C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 halo Alkynyl, cyano C _2-6 alkynyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, C _1-6 alkylthio, C _1-6 haloalkyl sulphide , C _3-8 cycloalkylthio, C _3-8 cycloalkyl C _1-6 alkylthio, C _1-6 alkoxy C _1-6 alkylthio, C _1-6 alkylsulfonyl , C _1-6 alkylsulfinyl, C _1-6 haloalkylsulfonyl, C _1-6 haloalkylsulfinyl, C _3-8 cycloalkylsulfonyl, C _3-8 ring Alkylsulfinyl, C _3-8 cycloalkyl, C _1-6 alkylsulfonyl, C _3-8 cycloalkyl C _1-6 alkyl sulfinylene, C _2-6 alkenyloxy C _2-6 alkyne Alkoxy group, C _2-6 haloalkenyloxy group, C _2-6 haloalkynyloxy group, C _1-6 alkylsulfonyloxy group, C _1-6 alkylsulfinyloxy group, C _1-6 alkylcarbonyl, C _1-6 haloalkylcarbonyl, carboxyl, OCN, SCN, SF ₅ , optionally substituted aryloxy, optionally substituted aryl C _1-6 alkoxy, Optionally substituted arylthio, optionally substituted aryl C _1-6 alkylthio, optionally substituted arylsulfonyl, optionally substituted arylsulfinyl, optionally Substituted heteroaryloxy, optionally substituted arylsulfonyloxy, optionally substituted arylsulfinyloxy, optionally substituted aryl, optionally substituted heteroaryl a heterocyclic group substituted or optionally substituted; and * is the point of attachment to the parent compound. Item 22. The dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ and R ^{37 are the} same or different and each represents hydrogen or halogen. Item 23. The dithiazide compound or a salt thereof or an N-oxide thereof according to any one of the preceding items, wherein the Y ² is selected from the group consisting of: , and And * is the point of attachment to the parent compound. Item 24: A dithiazide compound selected from the group consisting of 1c-1, 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c-4H, 1c-4L, 1c -5L, 1c-6L, 1c-8, 1c-8H, 1c-8L, 1c-9, 1c-9H, 1c-9L, 1c-10H, 1c-10L, 1c-11H, 1c-11L, 1c-13H , 1c-13L, 1c-14H, 1c-15H, 1c-16, 1c-16H, 1c-19, 1c-20, 1c-23, 1c-23H, 1c-23L, 1c-24, 1c-24H, 1c -25H, 1c-25L, 1c-26, 1c-26H, 1c-26L, 1c-27H, 1c-28L, 1c-29H, 1c-29L, 1c-30H, 1c-32H, 1c-32L, 1c-33 , 1c-34H, 1c-34L, 1c-35, 1c-35H, 1c-35L, 1d-1H, 1d-6H, 1d-6L, 1d-13, 1d-17, 1d-17H, 1d-17L, 1e -3 and 1e-7 or a salt thereof or an N-oxide thereof. Item 25: A dithiazide compound selected from the group consisting of 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c-4H, 1c-4L, 1c-5L, 1c -6L, 1c-8, 1c-8H, 1c-8L, 1c-9, 1c-9H, 1c-9L, 1c-10H, 1c-10L, 1c-11H, 1c-13H, 1c-13L, 1c-14H , 1c-15H, 1c-16, 1c-16H, 1c-19, 1c-20, 1c-23, 1c-23H, 1c-23L, 1c-24H, 1c-25H, 1c-25L, 1c-26, 1c -26H, 1c-26L, 1c-27H, 1c-29H, 1c-29L, 1c-32H, 1c-32L, 1c-33, 1c-34H, 1c-34L, 1c-35 and 1c-35H or salts thereof or Its N-oxide. Item 26: A dithiazide compound selected from the group consisting of 1c-1, 1c-1H, 1c-1L, 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c -4H, 1c-4L, 1c-5H, 1c-5L, 1c-6, 1c-6H, 1c-6L, 1c-7H, 1c-7L, 1c-8, 1c-8H, 1c-8L, 1c-9 , 1c-9H, 1c-9L, 1c-10H, 1c-10L, 1c-11H, 1c-11L, 1c-13H, 1c-13L, 1c-14H, 1c-15H, 1c-15L, 1c-16, 1c -16H, 1c-16L, 1c-17H, 1c-18L, 1c-19H, 1c-19L, 1c-20, 1c-21H, 1c-21L, 1c-22H, 1c-23, 1c-23H, 1c-23L , 1c-25H, 1c-25L, 1c-26, 1c-26H, 1c-26L, 1c-27H, 1c-27L, 1c-28H, 1c-28L, 1c-29H, 1c-29L, 1c-30H, 1c -30L, 1c-31H, 1c-31L, 1c-32H, 1c-32L, 1c-33, 1c-34H, 1c-34L, 1c-35, 1c-35H, 1c-35L, 1c-36, 1c-37 , 1c-37, 1c-40H, 1c-40L, 1c-41H, 1c-41L, 1d-1, 1d-1H, 1d-1L, 1d-12, 1d-13 and 1d-13L or a salt thereof or N thereof - Oxide. Item 27: A dithiazide compound selected from the group consisting of 1c-1, 1C-16, 1c-16H, 1c-16L and 1c-19H or a salt thereof or an N-oxide thereof. Item 28: A dithiazide compound selected from the group consisting of 1c-1, 1c-1L, 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c-4H, 1c -4L, 1c-5H, 1c-5L, 1c-6, 1c-6H, 1c-6L, 1c-8, 1c-8H, 1c-8L, 1c-9, 1c-9H, 1c-9L, 1c-10H , 1c-10L, 1c-11H, 1c-11L, 1c-12, 1c-12H, 1c-13, 1c-13H, 1c-13L, 1c-14H, 1c-15H, 1c-15L, 1c-16, 1c -16H, 1c-16L, 1c-17H, 1c-18L, 1c-19, 1c-19L, 1c-20, 1c-21H, 1c-21L, 1c-23, 1c-23H, 1c-23L, 1c-24 , 1c-24H, 1c-25H, 1c-25L, 1c-26, 1c-26H, 1c-26L, 1c-27H, 1c-30L, 1c-32H, 1c-32L, 1c-34H, 1c-34L, 1c -35, 1c-35H, 1c-35L, 1c-37, 1c-37L, 1c-38H, 1c-38L, 1c-44, 1b-5L, 1d-1H, 1d-1L, 1d-6L, 1d-7 , 1d-7H, 1d-7L, 1d-8, 1d-11, 1d-11H, 1d-11L, 1d-12L, 1d-15, 1d-16, 1d-16H, 1d-16L, 1d-17, 1d -17H and 1e-6 or a salt thereof or an N-oxide thereof. Item 29: A plant disease controlling agent comprising the dithiazide compound according to any one of items 1 to 28, or a salt thereof or an N-oxide thereof. Item 30: A fungicide comprising a dithiazide compound according to any one of items 1 to 28, or a salt thereof or an N-oxide thereof. Advantageous Effects of the Invention The dithiazide compound of the present invention or a salt thereof or an N-oxide thereof achieves an excellent fungicidal effect on a fungal plant pathogen. Further, the dithiazide compound of the present invention or a salt thereof or an N-oxide thereof can be used as a novel fungicide which exhibits excellent fungicidal activity not only against chemically sensitive fungi but also against chemical fungi.

Hereinafter, the present invention will be explained in more detail with reference to examples, but the technical scope of the present invention is not limited to the examples. Throughout the specification, the singular expression is to be understood as encompassing the concept of the plural. Therefore, the singular articles (such as "a", "the", "the" In addition, terms used herein are to be understood as being used in the meaning commonly used in the art, unless explicitly stated otherwise. Therefore, unless otherwise defined, all terms and scientific and technical terms used herein have the same meaning as the terms commonly understood by those skilled in the art. In the event of a conflict, the present specification, including definitions, will control.Dithiazide 𠷬 Compound or salt thereof or N- Oxide The present invention provides a dithiazide compound represented by the formula (1) or a salt thereof or an N-oxide thereof for use in agriculture and horticulture.Where R¹ , R² , R³ , Y¹ , Y² And the Q system is as defined above. The presence of one or more possible asymmetric carbon atoms in the compound of formula (1) means that the compound may optionally exist in an isomeric form, i.e., a mirror image or a non-image form. The presence of one or more possible double bonds in the compound of formula (1) means that the compound can exist in a variety of non-imagewise isomeric forms. Therefore, the structure:Means two forms, namely Z form and E form:and. Atropisomers may also be present due to limited rotation about a single bond. Formula (1) is intended to include all such possible isomeric forms and mixtures thereof. The invention includes all such possible isomeric forms of the compounds of formula (1) and mixtures thereof. Likewise, formula (1) is intended to include all possible tautomers. The invention includes all possible tautomeric forms of the compounds of formula (1). Next, the terms in this specification are explained below. In the present specification, the number of substituents of the group defined by "optionally substituted" or "substituted" is not specifically limited and is one or plural. In addition, unless otherwise indicated, the description for each group applies to a substituent on one or the other of the other groups of the group. "C_1-6 "Alkyl" means a straight or branched saturated hydrocarbon group having from 1 to 6 carbon atoms. "C_2-6 "Alkenyl" means a straight or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and having 1 to 3 double bonds. "C_2-6 "Alkynyl" means a straight or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing 1 triple bond. "C_3-8 "Cycloalkyl" means a cyclic alkyl group having from 3 to 8 carbon atoms and includes such cyclic alkyl groups having a partially bridged structure. "C_1-6 Alkoxy group (C_1-6 "alkoxy"" means "C_1-6 Alkoxy group (C_1-6 "alkoxy group)", and "C_1-6 The definition of the "alkyl group" and the "C" described above_1-6 The alkyl group is the same. "Aryl" means a monocyclic or polycyclic aromatic hydrocarbon. "Heterocyclic" means a saturated, unsaturated or aromatic heterocyclic group having at least one of nitrogen, oxygen, phosphorus and/or sulfur atoms in the ring and which may be bonded at any substitutable position. "Heteroaryl" means an aromatic heterocyclic group having at least one of nitrogen, oxygen and/or sulfur atoms in the ring and which may be bonded at any substitutable position, wherein the heteroaryl ring member atom In addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S are also included. Specific examples of each group as used in the present specification are shown below. Examples of halogens include, but are not particularly limited to, fluorine, chlorine, bromine, iodine, and the like. C_1-6 Examples of alkyl groups include, but are not specifically limited to, C_1-6 Linear or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, t-butyl, n-pentyl, n-hexyl and the like . C_1-6 Examples of haloalkyl groups include, but are not particularly limited to, C substituted with from 1 to 9, preferably from 1 to 5, halogen atoms._1-6 Linear or branched alkyl such as fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, 2,2-difluoroethyl, trifluoromethyl, 2,2,2 Trifluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, heptafluoroisobutyl and the like. C_1-6 Examples of alkoxy groups include, but are not specifically limited to, C_1-6 Linear or branched alkoxy group, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, second butoxy, tert-butoxy And so on. C_1-6 Examples of haloalkoxy include, but are not particularly limited to, C substituted with from 1 to 9, preferably from 1 to 5, halogen atoms._1-6 Linear or branched alkoxy groups such as fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-tri Fluoroethoxy, pentafluoroethoxy, 3,3,3-trifluoropropoxy, 4,4,4-trifluorobutoxy, heptafluoroisobutoxy and the like. C_1-6 Alkoxy C_1-6 Examples of alkyl groups include, but are not specifically limited to, C_1-6 Linear or branched alkyl via C_1-6 A linear or branched alkoxy substituted alkoxyalkyl group, such as methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl , isobutoxymethyl, second butoxymethyl, tert-butoxymethyl, methoxyethyl, ethoxyethyl, methoxy-n-propyl, methoxy-n-butyl Base and the like. C_1-6 Haloalkoxy C_1-6 Examples of the alkyl group include, but are not particularly limited to, a linear or branched alkoxyalkyl group substituted with 1 to 9, preferably 1 to 5 halogen atoms, such as a fluoromethoxymethyl group, Chloromethoxymethyl, bromomethoxymethyl, iodomethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 2,2,2-trifluoroethoxymethyl And so on. C_3-8 Examples of cycloalkyl groups include, but are not particularly limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like. C_3-8 Cycloalkyl C_1-6 Examples of alkyl groups include, but are not particularly limited to, cyclopropylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclohexylmethyl, and the like. C_1-6 Examples of alkylcarbonyl groups include, but are not specifically limited to, C_1-6 Linear or branched alkylcarbonyl group, such as methylcarbonyl (ethinyl), ethylcarbonyl (propyl), n-propylcarbonyl (butyl), isopropylcarbonyl (isobutyl), n-butylcarbonyl (pentyl), isobutylcarbonyl (isoamyl), t-butylcarbonyl, tert-butylcarbonyl, and the like. C_1-6 Examples of haloalkylcarbonyl include, but are not particularly limited to, C substituted with from 1 to 9, and preferably from 1 to 5, halogen atoms._1-6 Linear or branched alkylcarbonyl such as fluoromethylcarbonyl, chloromethylcarbonyl, bromomethylcarbonyl, iodomethylcarbonyl, dichloromethylcarbonyl, trichloromethylcarbonyl, difluoromethylcarbonyl, tri Fluoromethylcarbonyl, chlorodifluoromethylcarbonyl, bromodifluoromethylcarbonyl, dichlorofluoromethylcarbonyl, 2,2,2-trichloroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, Pentafluoroethylcarbonyl and the like. C_1-6 Examples of alkoxycarbonyl groups include, but are not specifically limited to, C_1-6 Linear or branched alkoxycarbonyl group, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, second butoxy Alkylcarbonyl, a third butoxycarbonyl group, and the like. C_1-6 Examples of haloalkoxycarbonyl include, but are not particularly limited to, C substituted with from 1 to 9, preferably from 1 to 5, halogen atoms._1-6 a linear or branched alkoxycarbonyl group such as fluoromethoxycarbonyl, chloromethoxycarbonyl, bromomethoxycarbonyl, iodomethoxycarbonyl, dichloromethoxycarbonyl, trichloromethoxycarbonyl, Difluoromethoxycarbonyl, trifluoromethoxycarbonyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 4, 4,4-Trifluorobutoxycarbonyl, heptafluoroisopropoxycarbonyl and the like. C_3-8 Examples of cycloalkylcarbonyl groups include, but are not particularly limited to, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, and the like. C_3-8 Examples of the cycloalkoxycarbonyl group include, but are not particularly limited to, a cyclopropyloxycarbonyl group, a cyclobutyloxycarbonyl group, a cyclopentyloxycarbonyl group, a cyclohexyloxycarbonyl group, and the like. Cyano C_1-6 Examples of alkyl groups include, but are not specifically limited to, C substituted by cyano_1-6 Linear or branched alkyl such as cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-isopropyl, cyano-n-butyl, cyano-isobutyl, cyano - a second butyl group, a cyano-t-butyl group, a cyano-n-hexyl group, and the like. Cyano C_1-6 Examples of alkoxy groups include C substituted by a cyano group_1-6 Linear or branched alkoxy group, such as cyanomethoxy, cyanoethoxy, cyano-n-propoxy, cyano-isopropoxy, cyano-n-butoxy, cyano- Isobutoxy, cyano-second butoxy, cyano-t-butoxy, cyano-hexyloxy and the like. C_2-6 Examples of alkenyl groups include, but are not particularly limited to, vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl, and the like. C_2-6 Examples of haloalkenyl groups include, but are not particularly limited to, 2,2-dichlorovinyl, 2,2-dibromovinyl, 2,2-difluorovinyl, 3,3-difluoro-2- Allyl, 4,4-difluoro-3-butenyl, 4,4,4-trifluoro-2-butenyl and the like. C_2-6 Examples of alkynyl groups include, but are not particularly limited to, ethynyl, 2-propynyl (propargyl), 1-methyl-2-propynyl, 1-butynyl, 2-butynyl, 3 - butynyl and the like. C_2-6 Examples of haloalkynyl groups include, but are not particularly limited to, fluoroethynyl, bromoethynyl, chloroethynyl, iodoethynyl, 3,3,3-trifluoro-1-propynyl, and the like. Cyano C_2-6 Examples of alkenyl groups include, but are not particularly limited to, 2-cyanovinyl, 2,2-dicyanovinyl, 3-cyano-2-allyl, 3,3-dicyano-2- Allyl, 4-cyano-3-butenyl, 4,4-dicyano-3-butenyl, 4,4,4-tricyano-2-butenyl and the like. Cyano C_2-6 Examples of alkynyl groups include, but are not particularly limited to, cyanoethynyl, 3-cyano-1-propynyl, and the like. C_1-6 Examples of alkylsulfonyl groups include, but are not specifically limited to, C_1-6 Linear or branched alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonate Anthracenyl, t-butylsulfonyl, tert-butylsulfonyl and the like. C_1-6 Examples of haloalkylsulfonyl groups include, but are not particularly limited to, C substituted with 1 to 9, preferably 1 to 5, halogen atoms._1-6 Linear or branched alkyl sulfinylene, such as fluoromethylsulfonyl, chloromethylsulfonyl, bromomethylsulfonyl, iodomethylsulfonyl, dichloromethylsulfonyl, Trichloromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, dichlorofluoromethylsulfonyl 2,2,2-trichloroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl and the like. C_1-6 Examples of alkylsulfinyl groups include, but are not specifically limited to, C_1-6 Linear or branched alkyl sulfinylene, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfin Base, isobutylsulfinyl, second butylsulfinyl, tert-butylsulfinyl, and the like. C_1-6 Examples of haloalkylsulfinyl groups include, but are not particularly limited to, C substituted with 1 to 9 and preferably 1 to 5 halogen atoms._1-6 Linear or branched alkyl sulfinylene, such as fluoromethylsulfinyl, chloromethylsulfinyl, bromomethylsulfinyl, iodomethylsulfinyl, dichloromethyl Sulfosyl, trichloromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfin Base, dichlorofluoromethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl And so on. C_1-6 Examples of alkylthio groups include, but are not specifically limited to, C_1-6 Linear or branched alkylthio, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, second butylthio , a third butyl thio group, and the like. C_1-6 Examples of haloalkylthio groups include, but are not particularly limited to, C substituted with 1 to 9 and preferably 1 to 5 halogen atoms._1-6 Linear or branched alkylthio group, such as fluoromethylthio, chloromethylthio, bromomethylthio, iodomethylthio, dichloromethylthio, trichloromethylthio, difluoromethylthio, three Fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, dichlorofluoromethylthio, 2,2,2-trichloroethylthio, 2,2,2-trifluoroethylsulfide Base, pentafluoroethylthio group and the like. C_3-8 Examples of cycloalkylsulfonyl groups include, but are not particularly limited to, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, and the like. C_3-8 Examples of cycloalkylsulfinyl groups include, but are not particularly limited to, cyclopropylsulfinylene, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, and the like. C_3-8 Examples of cycloalkylthio groups include, but are not particularly limited to, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, and the like. C_3-8 Cycloalkyl C_1-6 Examples of alkylsulfonyl groups include, but are not particularly limited to, cyclopropylmethylsulfonyl, 2-cyclopropylethylsulfonyl, 3-cyclopropylpropylsulfonyl, cyclohexylmethyl Sulfonyl and the like. C_3-8 Cycloalkyl C_1-6 Examples of alkylsulfinyl groups include, but are not particularly limited to, cyclopropylmethylsulfinyl, 2-cyclopropylethylsulfinyl, 3-cyclopropylpropylsulfinyl, Cyclohexylmethylsulfinyl and the like. C_3-8 Cycloalkyl C_1-6 Examples of alkylthio groups include, but are not particularly limited to, cyclopropylmethylthio, 2-cyclopropylethylthio, 3-cyclopropylpropylthio, cyclohexylmethylthio, and the like. C_1-6 Alkoxy C_1-6 Examples of alkylthio groups include, but are not specifically limited to, C_1-6 Linear or branched alkylthio group via C_1-6 a linear or branched alkoxy-substituted alkoxyalkylthio group, such as methoxymethylthio, ethoxymethylthio, n-propoxymethylthio, isopropoxymethylthio, N-butoxymethylthio group, second butoxymethylthio group, tert-butoxymethylthio group, 2-methoxyethylthio group and the like. C_2-6 Examples of alkenyloxy groups include, but are not particularly limited to, vinyloxy, 1-propenyloxy, isopropenyloxy, allyloxy, 2-butenyloxy, 3-butenyl Oxyl, 1-methylallyloxy and the like. C_2-6 Examples of haloalkenyloxy include, but are not particularly limited to, 2,2-dichlorovinyloxy, 2,2-dibromovinyloxy, 2,2-difluorovinyloxy, 3, 3-difluoro-2-allyloxy, 4,4-difluoro-3-butenyloxy, 4,4,4-trifluoro-2-butenyloxy and the like. C_2-6 Examples of alkynyloxy include, but are not particularly limited to, ethynyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 1,1-dimethyl-2- Propynyloxy, 1-butynyloxy, 2-butynyloxy, 3-butynyloxy and the like. C_2-6 Examples of haloalkynyloxy include, but are not particularly limited to, fluoroethynyloxy, bromoethynyloxy, chloroethynyloxy, iodoethynyloxy, 3,3,3-trifluoro-1 - propynyloxy and the like. C_1-6 Examples of alkylsulfonyloxy include, but are not particularly limited to, C_1-6 Linear or branched alkylsulfonyl, for example, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, n-butyl Sulfohydryloxy, isobutylsulfonyloxy, t-butylsulfonyloxy, tert-butylsulfonyloxy and the like. C_1-6 Examples of alkylsulfinyloxy include, but are not particularly limited to, C_1-6 Linear or branched alkyl sulfinyloxy, such as methylsulfinyloxy, ethylsulfinyloxy, n-propylsulfinyloxy, isopropylsulfin Alkoxy, n-butylsulfinyloxy, isobutylsulfinyloxy, t-butylsulfinyloxy, tert-butylsulfinyloxy and the like. Examples of substituted or unsubstituted amine groups include, but are not particularly limited to, amine groups, monoalkylamino groups, dialkylamino groups, monodecylamino groups, and the like. Examples of alkyl groups include the C mentioned above_1-6 Alkyl and the like. Examples of sulfhydryl groups include the C mentioned above_1-6 Alkylcarbonyl, C_1-6 Haloalkylcarbonyl, C_1-6 Alkoxycarbonyl, C_1-6 Haloalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl and the like. Examples of aryl groups include, but are not particularly limited to, phenyl, 1-naphthyl, 2-naphthyl, and the like. Aryl C_1-6 Examples of alkyl groups include, but are not particularly limited to, benzyl, phenylethyl, phenyl-n-propyl, and the like. The aryl C_1-6 The alkyl group can be further substituted at both the alkyl group and the aryl group. Examples of aryloxy groups include, but are not particularly limited to, phenoxy, 1-naphthyloxy, 2-naphthyloxy, and the like. Aryl C_1-6 Examples of alkoxy groups include, but are not particularly limited to, benzyloxy, phenylethoxy, phenyl-n-propoxy, phenyl-n-butoxy, 1-naphthylmethoxy, 2- Naphthylmethoxy and the like. Examples of heteroaryloxy groups include, but are not particularly limited to, pyridyloxy, pyrimidinyloxy, pyrazolyloxy, and the like. Examples of the arylsulfonyl group include, but are not particularly limited to, a phenylsulfonyl group, a 1-naphthylsulfonyl group, a 2-naphthylsulfonyl group, and the like. Examples of the arylsulfinyl group include, but are not particularly limited to, a phenylsulfinyl group, a 1-naphthylsulfinyl group, a 2-naphthylsulfinyl group, and the like. Examples of arylthio groups include, but are not particularly limited to, phenylthio, 1-naphthylthio, 2-naphthylthio, and the like. Examples of the arylsulfonyloxy group include, but are not particularly limited to, a phenylsulfonyloxy group, a 1-naphthylsulfonyloxy group, a 2-naphthylsulfonyloxy group, and the like. Examples of the arylsulfinyloxy group include, but are not particularly limited to, phenylsulfinyloxy, 1-naphthylsulfinyloxy, 2-naphthylsulfinyloxy, and the like . Aryl C_1-6 Examples of alkylthio groups include, but are not particularly limited to, benzylthio, phenylethylthio, phenyl-n-propylthio, phenyl-n-butylthio, 1-naphthylmethylthio , 2-naphthylmethylthio and the like. Examples of arylcarbonyl groups include, but are not particularly limited to, phenylcarbonyl, 1-naphthylcarbonyl, 2-naphthylcarbonyl, and the like. Examples of the aryloxycarbonyl group include, but are not particularly limited to, a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, a 2-naphthyloxycarbonyl group, and the like. Examples of heteroaryl groups include, but are not particularly limited to, thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, Thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, decyl, isodecyl, oxazolyl, quinazoline Polinyl, oxazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, benzimidazolyl, quinolyl, isoquinolinyl, pyridoindole , porphyrinyl, pyridazinyl, quinoxalinyl, fluorenyl, phenothiazine furyl, benzofuranyl, decyl, benzothienyl and the like. All aryl and heteroaryl groups mentioned above may be further substituted as appropriate. Examples of the number of substituents include, but are not particularly limited to, 1 to 20 (preferably 1 to 10, and more preferably 1 to 5). Examples of heterocyclic groups include, but are not particularly limited to, thienyl, furyl, tetrahydrofuranyl, dioxolanyl, dioxoalkyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, isomerism Azyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, isothiazolyl, thiazolinyl, thiazolidinyl, isothiazolinyl, pyrazolyl, pyrazolyl, imidazolyl , imidazolinyl, imidazolidinyl, oxadiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, triazolinyl, triazolyl, tetrazolyl, tetrazolinyl, pyridine , dihydropyridyl, tetrahydropyridyl, hexahydropyridyl, oxazinyl, dihydrooxazinyl, morpholinyl, thiazinyl, dihydrothiazinyl, thiamorpholinyl, pyridazinyl , dihydropyridazinyl, tetrahydropyridazinyl, hexahydroazinyl, oxadiazinyl, dihydrooxadiazinyl, tetrahydrooxadiazinyl, thiadiazolyl, thiadiazinyl, dihydrogen Thiadiazinyl, tetrahydrothiazinyl, pyrimidinyl, dihydropyrimidinyl, tetrahydropyrimidinyl, hexahydropyrimidinyl, pyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, hexahydropyrazine Base, triazinyl, Hydrotriazinyl, tetrahydrotriazinyl, hexahydrotriazinyl, tetrazinyl, dihydrotetrazinyl, fluorenyl, porphyrin, isodecyl, oxazolyl, quinazolinyl, Dihydroquinazolinyl, tetrahydroquinazolinyl, oxazolyl, benzoxazolyl, benzoxazolinyl, benzisoxazolyl, benzisoxazolinyl, benzothiazolyl Benzoisothiazolyl, benzisothiazolinyl, benzimidazolyl, oxazoline, quinolyl, dihydroquinolinyl, tetrahydroquinolyl, isoquinolinyl, dihydroisoquinoline , tetrahydroisoquinolyl, pyridoindoleyl, dihydrobenzoxazinyl, porphyrinyl, dihydroporphyrinyl, tetrahydroporphyrinyl, pyridazinyl, dihydropyridazinyl, tetra Hydropyridazinyl, quinoxalinyl, dihydroquinoxalinyl, tetrahydroquinoxalinyl, fluorenyl, dihydrobenzotriazinyl, dihydrobenzotetrazinyl, phenothiazineylfuranyl, Benzofuranyl, decyl, benzothienyl and the like. The heterocyclic groups include those substituted at the substitutable position with a pendant oxy or thioketo group. All of the heterocycles mentioned above may be further substituted as appropriate. Examples of the number of substituents include, but are not particularly limited to, 1 to 20 (preferably 1 to 10 and more preferably 1 to 5). Examples of "substituted" or "substituent" include, but are not particularly limited to, halogen, nitro, cyano, hydroxy, methionyl, C_1-6 Alkyl, C_1-6 Haloalkyl, C_1-6 Alkoxy, C_1-6 Haloalkoxy, C_1-6 Alkoxy C_1-6 Alkyl, C_1-6 Haloalkoxy C_1-6 Alkyl, C_3-8 Cycloalkyl, C_3-8 Cycloalkyl C_1-6 Alkyl, C_1-6 Alkylcarbonyl, C_1-6 Haloalkylcarbonyl, C_1-6 Alkoxycarbonyl, C_1-6 Haloalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C_1-6 Cyanoalkyl, C_1-6 Cyanoalkoxy, C_2-6 Alkenyl, C_2-6 Haloalkenyl, C_2-6 Alkynyl, C_2-6 Haloalkynyl, C_1-6 Alkylsulfonyl, C_1-6 Haloalkylsulfonyl, C_1-6 Alkylsulfinyl, C_1-6 Haloalkylsulfinyl, C_1-6 Alkylthio, C_1-6 Haloalkylthio, C_3-8 Cycloalkylsulfonyl, C_3-8 Cycloalkylsulfinyl, C_3-8 Cycloalkylthio, C_3-8 Cycloalkyl C_1-6 Alkylsulfonyl, C_3-8 Cycloalkyl C_1-6 Alkylsulfinyl, C_3-8 Cycloalkyl C_1-6 Alkylthio, C_1-6 Alkoxy C_1-6 Alkylsulfonyl, C_1-6 Alkoxy C_1-6 Alkylsulfinyl, C_1-6 Alkoxy C_1-6 Alkylthio, C_2-6 Alkenyloxy, C_2-6 Haloalkenyloxy, C_2-6 Alkynyloxy, C_2-6 Haloalkynyloxy, C_1-6 Alkylsulfonyloxy, C_1-6 Haloalkylsulfonyloxy, C_1-6 Alkylsulfinyloxy, C_1-6 Haloalkylsulfinyloxy, OCN, SCN, SF₅ Substituted or unsubstituted amine, aryl, aryl C_1-6 Alkyl, aryloxy, aryl C_1-6 Alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C_1-6 Alkylsulfonyl, aryl C_1-6 Alkylsulfinyl, aryl C_1-6 Alkylthio, heterocyclic, heterocyclic C_1-6 Alkyl, heterocyclic oxy and the like. The salt of the compound represented by the formula (1) may be any type of salt as long as it is an agriculturally acceptable salt. Examples of such salts include inorganic acid salts such as hydrochlorides, sulfates, nitrates and the like; organic acid salts such as acetates, methanesulfonates and the like; alkali metal salts such as sodium salts, potassium salts and the like Alkaline earth metal salts such as magnesium salts, calcium salts and the like; quaternary ammonium salts such as dimethylammonium, triethylammonium and the like; and the like. In the present invention, the N-oxide is a compound which constitutes an oxidation of an atom of a ring in the heterocyclic group. The heterocyclic group which may constitute the N-oxide may be, for example, a fused ring containing a pyridine ring, a fused ring containing a pyrazine ring, a fused ring containing a pyridazine ring or a fused ring containing a pyrimidine ring. In the compound (1) of the present invention, preferred compounds are those in which R¹ Hydrogen, halogen or C_1-6 a compound of an alkyl group, and more preferably a compound (1) wherein R¹ A compound that is hydrogen or methyl. In the compound (1) of the present invention, preferred compounds are those in which R² Hydrogen, halogen or C_1-6 a compound of an alkyl group, and more preferably a compound (1) wherein R² A compound that is hydrogen. In the compound (1) of the present invention, preferred compounds are those in which R³ Hydrogen, halogen or C_1-6 a compound of an alkyl group, and more preferably a compound (1) wherein R³ A compound that is hydrogen. In the compound (1) of the present invention, a preferred compound is Y¹ a compound substituted with an aryl group or an optionally substituted pyridyl group, and more preferably a compound (1) wherein Y¹ a substituted phenyl group, optionally substituted 3-pyridyl group or optionally substituted 4-pyridyl compound, and particularly preferably compound (1) wherein Y¹ A 3-pyridyl compound which is optionally substituted. In the compound (1) of the present invention, a preferred compound is Y² a compound substituted with an aryl group or an optionally substituted pyridyl group, and more preferably a compound (1) wherein Y² A compound of a phenyl group which is optionally substituted. Among the compounds (1) of the present invention, preferred compounds are those in which a Q-based cyano group. In the compound (1) of the present invention, preferred compounds are those in which R⁴ , R⁵ , R⁶ , R⁷ And R⁸ Same or different and each is hydrogen, halogen, C_1-6 Alkyl, C_1-6 Haloalkyl, C_1-6 Alkoxy or C_1-6 a halogenated alkoxy compound, and more preferably a compound (1) wherein R⁴ , R⁵ , R⁶ , R⁷ And R⁸ Compounds which are the same or different and each are hydrogen, fluorine, chlorine, bromine, tert-butyl, trifluoromethyl, methoxy or trifluoromethoxy. In the compound (1) of the present invention, preferred compounds are those in which R⁹ , R¹⁰ , R¹¹ , R¹² , R¹³ , R¹⁴ , R¹⁵ , R¹⁶ , R¹⁷ , R¹⁸ , R¹⁹ And R²⁰ Compounds which are the same or different and each are hydrogen or halogen, and more preferably compound (1) is R⁹ , R¹⁰ , R¹¹ , R¹² , R¹³ , R¹⁴ , R¹⁵ , R¹⁶ , R¹⁷ , R¹⁸ , R¹⁹ And R²⁰ A compound of hydrogen or chlorine. In the compound (1) of the present invention, preferred compounds are those in which R^{twenty one} , R^{twenty two} , R^{twenty three} , R^{twenty four} And R²⁵ Identical or different and each is hydrogen, halogen, nitro, cyano, optionally substituted amine, C_1-6 Alkyl, C_1-6 Haloalkyl, C_1-6 Alkoxy, C_1-6 a halogenated alkoxy group or a compound of an optionally substituted aryl group, and more preferably a compound (1) wherein R^{twenty one} , R^{twenty two} , R^{twenty three} , R^{twenty four} And R²⁵ Compounds which are the same or different and each are hydrogen, fluorine, chlorine, bromine, nitro, cyano, amine, methyl, trifluoromethyl, methoxy, trifluoromethoxy or phenyl. In the compound (1) of the present invention, preferred compounds are those in which R²⁶ , R²⁷ , R²⁸ , R²⁹ , R³⁰ , R³¹ , R³² , R³³ , R³⁴ , R³⁵ , R³⁶ And R³⁷ Compounds which are the same or different and each are hydrogen or halogen, and more preferably compound (1) is R²⁶ , R²⁷ , R²⁸ , R²⁹ , R³⁰ , R³¹ , R³² , R³³ , R³⁴ , R³⁵ , R³⁶ And R³⁷ A compound that is hydrogen. Among these compounds, a more preferred compound of the present invention is a compound or a salt thereof or an N-oxide thereof:¹ Hydrogen, halogen or C_1-6 Alkyl; R² Hydrogen, halogen or C_1-6 Alkyl; R³ Hydrogen, halogen or C_1-6 Alkyl; Y¹ a substituted aryl or optionally substituted pyridyl group;² An optionally substituted aryl or optionally substituted pyridyl group; Q is a cyano group. More preferably, the compound of the present invention is a compound or a salt thereof or an N-oxide thereof:¹ Hydrogen or methyl; R² Hydrogen; R³ Hydrogen; Y¹ a substituted phenyl group, optionally substituted 3-pyridyl group or optionally substituted 4-pyridyl group;² a phenyl group which is optionally substituted; a Q-based cyano group. Particularly preferred compounds of the invention are those wherein the compound or a salt thereof or an N-oxide thereof:¹ Hydrogen or methyl; R² Hydrogen; R³ Hydrogen; Y¹ 3-pyridyl group substituted as appropriate; Y² a phenyl group which is optionally substituted; a Q-based cyano group. The present invention also provides a process for producing a dithiazide represented by the formula (1) or a salt thereof or an N-oxide thereof:, where R¹ , R² , R³ , Y¹ , Y² And the Q system is as defined above. The dithiazide compound represented by the formula (1) of the present invention can be easily produced according to the following Reaction Scheme 1, but is not limited to the methods. The dithiazide compound represented by the formula (1) can be produced by reacting the compound (2) with the compound (3) and carbon disulfide in the presence of a base and a solvent as mentioned in Reaction Scheme 1. Reaction scheme 1Where R¹ , R² , R³ , Y¹ , Y² And the Q system is as defined above. Meanwhile, A and B are the same or different and each represents a suitable de-bonding group such as chlorine, bromine and iodine; substituted or unsubstituted C_1-6 An alkyl sulfonate group; and a substituted or unsubstituted aryl sulfonate group. The amount of the compound (3) to be used is usually 0.5 mol to 5 mol, preferably 1 mol to 2 mol, per 1 mol of the compound (2). The amount of carbon disulfide used is usually 2 mol to 10 mol, preferably 1 mol to 2 mol, per 1 mol of the compound (2). This reaction is carried out in the presence of a suitable base. As the base, a conventional base can be widely used, and examples of the base include: an alkali metal carbonate such as sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate, and the like; an alkali metal hydroxide such as Sodium hydroxide, potassium hydroxide and the like; alkali metal hydrides such as sodium hydride and potassium hydride and the like; alkali metal hydrides such as sodium hydride and potassium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, Potassium tert-butoxide and the like; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine And hexahydropyridine and the like, preferably sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, sodium methoxide, sodium ethoxide and potassium butoxide. Any one of these bases or a combination of two or more of these types is used. In the case of using an organic base, it can be used in a large excess to be used as a solvent. The amount of the base to be used is usually 2 mol to 5 mol, preferably 2 mol to 3 mol, per 1 mol of the compound (2). The reactions mentioned above are carried out in a suitable solvent or in the absence of any solvent. When the above-mentioned reaction is carried out in a solvent, there is no limitation on the solvent as long as the solvent is inactive with respect to the reaction mentioned above. Examples of such a solvent include: a solvent based on a fatty acid or an alicyclic hydrocarbon such as n-hexane, cyclohexane, n-heptane, and the like; a solvent based on an aromatic hydrocarbon such as benzene, chlorobenzene, toluene, xylene, and the like a solvent based on a halogenated hydrocarbon such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, and the like; an ether-based solvent such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxin Alkanes, dimethoxyethanes and the like; ester solvents such as methyl acetate, ethyl acetate and the like; acetonitrile; guanamine-based solvents such as N,N-dimethylformamide (DMF), N, N-dimethylacetamide, N-methyl-2-pyrrolidone, and the like; a solvent based on hydrazine, such as dimethyl hydrazine (DMSO), sulforane, and the like;₂ O; acetic acid; preferably DMSO, DMF, toluene and THF. Any of these solvents may be used alone or a combination of two or more types thereof may be used as necessary. The amount of the solvent used is usually from 1 liter to 20 liters, preferably from 1 liter to 10 liters per 1 mol of the compound (2). The reaction is usually carried out at a temperature of from -10 ° C to the boiling point of the solvent. The reaction time is usually in the range of 0.25 hours to 24 hours or longer depending on the completion of the reaction. The compound (2) used in this step can be produced according to a known method (for example, WO2007/045989, Synlett (15), 2223-2227 (2011), and Molecular Diversity 18(2), 307-322 (2014). The method described). The compound (3) used in this step can be produced according to a known method (for example, the methods described in WO2006/110804, WO2015/003991, WO2015/11194, and WO2015/162271). The compound represented by the formula (1) obtained by the method shown in Scheme 1 is easily isolated from the reaction mixture and can be purified by using a typical separation method and purification method such as filtration, solvent extraction, distillation, recrystallization. , column chromatography, etc. Although the compound of the present invention may be used in the form of the compound of the present invention, the compound of the present invention is usually prepared by mixing the compound of the present invention with a solid carrier, a liquid carrier, a gas carrier, a surfactant, and others, and If necessary, add an adhesive, a dispersing agent and a stabilizer to prepare a wettable powder, water-dispersible granules, a flowable agent, granules, a dry flowable agent, an emulsifiable concentrate, an aqueous solution, an oil solution, Smoke agents, aerosols, microcapsules and others. The content of the compound of the invention in these formulations is generally in the range of from 0.1% by weight to 99% by weight, preferably from 0.2% by weight to 90% by weight. Examples of solid carriers include clays in the form of fine powders or particulates (for example, kaolin, diatomaceous earth, synthetic hydrated cerium oxide, fubasami clay, bentonite and acid clay), talc or other inorganic minerals. Substances (eg, sericite, quartz powder, sulfur powder, activated charcoal, calcium carbonate, and hydrated ceria), and examples of liquid carriers include water, alcohols (eg, methanol and ethanol), ketones (eg, acetone and methyl) Ethyl ketone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, and methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexane, and kerosene), esters (eg, ethyl acetate) Ester and butyl acetate), nitriles (for example, acetonitrile and isobutyronitrile), ethers (for example, dioxane and diisopropyl ether), decylamine (for example, DMF and dimethylacetamide), halogenated hydrocarbons (eg, dichloroethane, trichloroethylene, and carbon tetrachloride) and others. Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylated compounds thereof, polyethylene glycol ethers, polyol esters, and sugar alcohols. derivative. Examples of other auxiliaries for formulation include adhesives, dispersants and stabilizers, in particular casein, gelatin, polysaccharides (for example, starch, gum arabic, cellulose derivatives and alginic acid), lignin derivatives, Bentonite, sugar, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acid), PAP (isopropyl isopropyl phosphate), BHT (2,6-di-t-butyl-4) -methylphenol), BHA (a compound of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid or its fatty acid ester And others. The method for administering the compound of the present invention is not particularly limited as long as the administration form is a form in which the compound of the present invention can be substantially applied, and includes, for example, application to plants, such as foliar application; for cultivation of plants Application of the area, such as submergence treatment; and application to the soil, such as seed disinfection. The dosage will vary depending on the weather conditions, dosage form, period of administration, method of application, area to be applied, target disease and target crop, etc., but at every 1,000 m.² The area to be applied is usually in the range of 1 g to 500 g and preferably 2 g to 200 g. Emulsifying concentrates, wettable powders or suspension concentrates and the like are usually applied by diluting them with water. In this case, the concentration of the compound of the present invention after dilution is in the range of usually 0.0005 wt% to 2 wt% and preferably 0.005 wt% to 1 wt%. Powder formulations or granule formulations and the like are usually applied in their own form without dilution. In the application to the seed, the amount of the compound of the present invention is usually in the range of 0.001 g to 100 g and preferably 0.01 g to 50 g per 1 kg of seed. In this context, examples of pest habitats include rice fields, fields, tea gardens, orchards, non-agricultural land, houses, seedling trays, nursery boxes, nursery soils, and nursery beds. Further, in another embodiment, for example, the compound of the present invention can be administered to the inside (in vivo) or the outside (body surface) of the vertebrate mentioned below to eliminate parasitism systemically or non-systemically. A creature or parasite in a vertebrate. Examples of methods of internal administration include oral administration, transanal administration, transplantation, administration via subcutaneous, intramuscular or intravenous injection. Examples of methods of topical agents include transdermal administration. Furthermore, the compounds of the invention may be ingested by livestock animals in order to eliminate the presence of hygienic insects in animal waste. When the compound of the present invention is applied to animals such as livestock animals and pets of parasitic pests, the dosage is varied depending on the administration method, etc., but it is generally desired to administer the compound of the present invention such that the active ingredient (the compound of the present invention or The dose of the salt is usually in the range of 0.1 mg to 2,000 mg and preferably 0.5 mg to 1,000 mg per 1 kg of animal body weight. The compound of the present invention can be used as an agent for controlling plant diseases in agricultural land such as fields, rice fields, lawns, orchards. The compound of the present invention can prevent diseases occurring in agricultural land or other sites for cultivating the following "plants". Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beets, rapeseed, sunflower, sugar cane, tobacco and others; vegetables: solanaceous vegetables (eg, Eggplant, tomato, sweet pepper, pepper and potato), cucurbitaceous vegetables (eg cucumber, pumpkin, winter squash, watermelon and melon), cruciferous vegetables (eg, Japanese radish, white radish, spicy) Roots, bulbs, Chinese cabbage, cabbage, snow red, broccoli, broccoli), asteraceous vegetables (eg, burdock, sage, artichoke and lettuce), liliaceous vegetables (eg, small onions) , onions, garlic and asparagus), ammiaceous vegetables (eg carrots, parsley, celery and parsnips), chenopodiaceous vegetables (eg spinach and saucy (Swiss chard)), lip shape Laciaceous vegetables (eg Perilla frutescens, mint and basil), strawberries, sweet potatoes, Dioscorea japonica, alfalfa and others; flowers: foliage plants: fruits Pome fruit (eg, apple, pear, Japanese pear, Chinese quince and medlar), stone fruit (eg, peach, plum, nectarine, plum (Prunus mume), cherry fruit, apricot and dried fruit plum), Citrus fruits (eg, Citrus unshiu, oranges, lemons, limes, and grapefruits), nuts (eg, chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, and macadamia nuts) , berries (eg, blueberries, cranberries, blackberries, and raspberries), grapes, kaki persimmon, olives, Japanese plums, bananas, coffee, date palms, coconuts, and others; trees other than fruit trees: tea trees, Mulberry, flowering plants, street trees (for example, ash, birch, hawthorn, eucalyptus, ginkgo biloba, lilac, maple, eucalyptus (Quercus), poplar, bauhinia (Judas tree) ), Liquidambar formosana, Platanus, Eucalyptus, Japanese arborvitae, fir, hemlock, juniper, Pinus, Picea, and Taxus cuspidata; And others. The "plant" mentioned above includes genetically modified crops. The pests to which the compounds of the present invention have control properties include plant pathogens (e.g., filamentous fungi), as well as harmful arthropods (e.g., harmful insects and harmful mites) and linear animals (e.g., nematodes), and specifically include the following examples, but Not limited to it. Rice diseases: rice blast (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), mite disease (Fujikang) Gibberella fujikuroi and sclerotium (Sclerophthora macrospora); wheat disease: powdery mildew (Erysiphe graminis), Fusarium bacterium (Fusarium graminearum) ), F. avenaceum, F. culmorum, Microdochium nivale, rust (Puccinia striiformis, Pleurotus ostreatus) . graminis), P. recondita, snow rot (Micronectriella nivale), typhulasnow blight (Typhula sp.) , smut (Ustilago tritici), smut (Tilletia caries, T. controversa), eye spot disease ( Wheat rot (Pseudocercosporella herpotrichoides), leaf spot blight (Septoria tritici), Blight (Stagonospora nodorum), brown spot (Pyrenophora tritici-repentis), rhizoctonia seedling blight (Rhizobacter serrata) (Rhizoctonia solani)) and total eclipse (Gaeumannomyces graminis); barley disease: powdery mildew (white powdery mildew), Fusarium blight (Fusarium graminearum, Fusarium oxysporum, Fusarium oxysporum Bacteria, red snow rot), rust (Puccinia striiformis, Pleurotus ostreatus, P. hordei), smut (Ustilago nuda), moiré (Rhynchosporium secalis), net spot disease (Pyrenophora teres), spotted blisters (Cochliobolus sativus), leaf streak disease (M. genus) Pyrenophora graminea)), Ramularia disease (Ramularia collo-cygni) and Rhizoctonia solani (Rhizobium ssp.); Corn disease: rust ( Puccinia sorghi), southern rust (Puccinia polysora), northern leaf blight (jade) Setosphaeria turcica, Southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (C. cerevisiae) (Cercospora zeae-maydis)), eye spot disease (Kabatiella zeae) and phaeosphaeria leaf spot (Phaeosphaeria maydis); cotton disease: Anthracnose (Colletotrichum gossypii), Ramularia areola, Alternaria leaf spot (Alternaria macrospora, Alternaria californica) A. gossypii); coffee disease: rust (Hemileia vastatrix); rapeseed disease: sclerotinia (Sclerotinia sclerotiorum), black spot (Alternaria Alternaria brassicae) and black foot disease (Phoma lingam); citrus diseases: melanosis (Diaporthe citri), scab (Elsinoe) Fawcettii)) and fruit rot (Penicillium digitatum, white Penicillium (P. italicum); Apple disease: flower blight (Monilinia mali), ulcer disease (Valsa ceratosperma), powdery mildew (white cross silk single shell) (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis) and bitter rot (quick anthrax) Colletotrichum acutatum; Pear disease: scab disease (Venturia nashicola, V. pirina), black spot (Japanese pear-shaped Alternaria) and Rust (Gymnosporangium haraeanum); Peach disease: brown rot (Monilinia fructicola), scab (Cladosporium carpophilum) and Phomopsis rot (Phomopsis rot) Phomopsis sp.; grape disease: anthracnose (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (grape stalk) Uncinula necator), rust (Phakopsora ampelopsidis), black rot (grape squash) (Guignardia bidwellii)) and Phytophthora (Plasmopara viticola); Japanese persimmon disease: anthracnose (Gloeosporium kaki) and leaf spot (Cercospora) Kaki), Mycosphaerella nawae); disease of Cucurbitaceae: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), blight (small double Didymella bryoniae), target spot disease (Corynespora cassiicola), Fusarium oxysporum, Fucobacterium (Pseudoperonospora) Cubensis)), phytophthora rot (Phytophthora sp.) and rickety (Pythium sp.); tomato disease: early blight (Alternaria solani) (Alternaria solani)), leaf mold (Cladosporium fulvum), leaf mold (Pseudocercospora fuligena) and late blight (Phytophthora infestans); eggplant Diseases: brown spot (Phomopsis vexans) and powdery mildew (Eryia sphaeroides) Siphe cichoracearum)); diseases of cruciferous vegetables: Alternaria leaf spot (Alternaria japonica), leukoplakia (Cercosporella brassicae), clubroot disease (parasitic Plasmodiophora parasitica, Peruvian porcini (Peronospora parasitica); Scallion disease: rust (Puccinia allii); Soybean disease: Purple spot (Cercospora kikuchii) ), sphaceloma scad (Elsinoe glycines), pod and stem blight (Diaporthe phaseolorum var. sojae) , rust (phakopsora pachyrhizi), target spot disease (Pseudomonas sphaeroides), anthracnose (Glyphs of Colletotrichum glycines, C. truncatum) Rhizoctonia aerial disease (Rhizobacter serrata), septoria brown spot (Septoria glycines) and frog eye leaf spot (soybean Cercospora sojina); Bean disease: anthracnose (Colletotrichum lindemuthianum)); Peanut disease: early leaf spot (Cercospora personata), advanced leaf spot (Cercospora arachidicola) and southern blight (small blight) Sclerotium rolfsii); pea disease: powdery mildew (Erysiphe pisi); potato disease: early blight (Alternaria solani), late blight (Phytophthora infestans) and verticillium (verticillium wilt) (verticillium albo-atrum, V. dahliae, V. nigrescens); strawberry disease: powdery mildew Sphaerotheca humuli); Tea tree disease: Reticulum disease (Exobasidium reticulatum), white acne (Elsinoe leucospila), Phytophthora (Pestalotiopsis sp.) .)) and anthracnose (Colletotrichum theae-sinensis); tobacco diseases: brown spot (Alternaria longipes), powdery mildew (white powder), anthracnose (Tobacco anthrax (Colletotrichum tabacum), dew disease (tobacco cream) Mold (Peronospora tabacina) and black plague (Phytophthora nicotianae); Sugar beet disease: cercospora leaf spot (Cercospora beticola), leaf blight ( Thanatephorus cucumeris, root rot (Gua dynasty) and aphanomyces root rot (Aphanomyces cochlioides); rose disease: black spot ( Diplocarpon rosae and powdery mildew (Sphaerotheca pannosa); disease of chrysanthemum: leaf blight (Septoria chrysanthemi-indici) and white rust (handle rust) Puccinia horiana); Onion disease: Botrytis leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa) )), gray mold neck rot (Botrytis allii) and small sclerotia sp. (Bacillus sphaeroides); various crop diseases: gray mold (Botrytis cinerea) and sclerotinia (Sclerotium); Japanese radish disease: Alternaria brassicola (Alternaria brassicicola) Turfgrass disease: dollar spot (Sclerotinia homoeocarpa), brown spot and giant spot disease (Rhizobium); and banana disease: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola). Hemiptera: Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens or Sogatella furcifera); Deltocephalinae (eg, Nephotettix cincticeps or Nephotettix virescens); Aphididae (eg, Aphis gossypii, Myzus persicae, Rapeseed) (Brevicoryne brassicae), Macrosiphum euphorbiae, Aulacorthum solani, Rhopalosiphum padi, Toxoptera citricidus, Pentatomidae (eg, rice green carp (Nezara) Antennata), Riptortus clavatus, Leptocorisa chinensis, Eysarcoris parvus, Halyomorpha mista or Lygus lineolaris; (Aleyrodidae) (for example, Trialeurodes vaporariorum or Bemisia argentifolii); Coccoidea (for example, Aonidiella aurantii, Pear round scale insect (Comstock) Aspis perniciosa), Unaspis citri, Ceroplastes rubens or Icerya purchasi; Tingidae; Psyllidae; bed bug (temperate bed bug) (Cimex lectularius)) and others. Lepidoptera: Pyralidae (eg, Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella, Ostrinia furnacalis, Hellula undalis, Pediasia teterrellus, Noctuidae (eg, Spodoptera litura) ), Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Plusia nigrisigna, Spodoptera frugiperda Trichoplusia spp.), Heliothis spp. or Helicoverpa spp.; Pieridae (eg, Pieris rapae), Tortricidae (eg, tea) Adoxophyes spp., Grapholita molesta, Cydia pomonella, Leguminivora glycinivorella, Matsumuraeses azukivora, Cotton brown leaf moth (Ad Oxophyes orana fasciata), Homona magnanima, Archips fuscocupreanus, and codling moth; (Gracillariidae) (eg, Caloptilia theivora, golden moth) Phyllonorycter ringoniella)); Carposinidae (for example, Carposina niponensis); Lyonetiidae (for example, Lyonetia spp.); Lymantriidae ( For example, Lymantria spp. or Euproctis spp.; Yponomeutidae (eg, Plutella xylostella); Gelechiidae (eg, red bollworm) Pectinophora gossypiella) or Phthorimaea operculella; Arctiidae (eg, Hyphantria cunea); Tineidae (eg, Tinea translucens or Coat Moth) (Tineola bisselliella); and others; Thysanoptera: Thysanoptera (for example, Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Green onion horse Thrips tabaci), Frankliniella intonsa, Frankliniella fusca; Diptera: Musca domestica, Culex pipiens pallens, Tabanus Trigonus), Hylemya antiqua, Hylemya platura, Anopheles sinensis, Agromyza oryzae, Hydrellia griseola, Chlorops oryzae ), Dacus cucurbitae, Ceratitis capitata, Liriomyza trifolii and others; Coleoptera: Epilachna vigintioctopunctata, yellow Aulacophora femoralis, Phyllotreta striolata, Oulema oryzae, Echinocnemus squameus, Lisorhoptrus oryzophilus, Mexican cotton aphid weevil (Anthonomus grandis), mung bean (Callosobruchus chinensis), parasitic worm (Sphenophorus venatus), Japanese chafer (Popillia japonica), bronze terracotta (Anomala cuprea) ), Diabrotica spp., Leptinotarsa decemlineata, Agriotes spp., Lasioderma serricorne, Anthrenus verbasci, Tribolium castaneum, Lyctus brunneus, Anoplophora malasiaca, Tomicus piniperda and others; Orthoptera: Locusta migratoria ), Gryllotalpa africana, Oxya yezoensis, Oxya japonica and others; Hymenoptera: Athalia rosae, Acromyrmex Spp.), Solenopsis spp. and others; nematodes: Aphelenchoides besseyi, Nothotylenchus acris, Heterodera glycines, Meloidogyne incognita ), root rot nematode (Pratylenchus), pseudo-root-knot nematode (Nacobbus aberrans) and others; Blattariae: Blattella germanica, Periplaneta fuliginosa, beauty Periplaneta americana, Periplaneta brunnea, Blatta orientalis, and others; Acarina: Tetranychidae (eg, Tetranychus urticae) ), Panonychus citri or Oligonychus spp.; Eriophyidae (for example, Aculops pelekassi); Tarsonemidae (for example, Polyphagotarsonemus latus); Tenuipalpidae; Tuckerellidae; Acaridae (eg, Tyrophagus putrescentiae); Dynamite family (Pyroglyphidae) (eg, Dermatophagoides farinae or Dermatophagoides pteronyssinus); Cheyletidae (eg, Cheyletus eruditus, Cheyletus malaccensis, or Mohs) Cheyletus moorei); Dermanyssidae; and others. Formulations comprising a compound of the invention or a salt thereof can also be used in the field of treating livestock disease or animal husbandry, and for example can eliminate parasitic vertebrate (eg human, cow, sheep, pig, poultry, dog, cat and fish) Biological or parasites on the inside and / or outside to maintain public health. Examples of pests include Ixodes spp. (e.g., Ixodes scapularis), Boophilus spp. (e.g., Boophilus microplus), Amaranthus (Amblyomma) Spp.), Hyalomama spp., Rhipicephalus spp. (eg, Rhipicephalus sanguineus), Haemaphysalis spp. (eg, long-horned blood) Ha (Haemaphysalis longicornis), dermacentor spp., Ornithodoros spp. (eg, Ornithodoros moubata), chicken larvae (Dermanyssus gallinae), forest locust hedgehog (Ornithonyssus sylviarum), Sarcotes spp. (eg, Sarcoptes scabiei), Psoroptes spp., Chorioptes spp., Trichomonas ( Demodex spp.), Eutrobicula spp., Ades spp. (eg Aedes albopictus), Anopheles spp., Culex Spp.), Culicoides spp., Musca spp., Hypoderma spp., Ghost (Gaster) (ophilus spp.), Haematobia spp., Tabanus spp., Simulium spp., Triatoma spp., Phthiraptera (eg, biting) Damalinia spp., Linognathus spp., Haematopinus spp., Ctenocephalides spp. (eg, Ctenocephalides felis), Xenopsylla spp., monomorium pharaonis, and nematodes, golden worms (eg, Nippostrongylus brasiliensis, Trichostrongylus axei, snake-like worms) (Trichostrongylus colubriformis)), Trichinella spp. (eg, Trichinella spiralis), Haemonchus contortus, Nematodirus spp. (eg, Nematodes) (Nematodirus battus)), Ostertagia circumcincta, Cooperia spp., Hymenolepis nana and other pests. The dithiazide (1) of the present invention is used as an active ingredient of, for example, a fungicide. The dithiazide (1) of the present invention can be used by making a desired form such as an oil, an emulsion, a wettable powder, a flowable formulation, a granule, a powder, an aerosol, a fumigant or the like. In this case, the content of the dithiazide (1) of the present invention is not limited and may be appropriately selected depending on various conditions, such as the form of the preparation, the type of the disease to be treated, the type of the plant, and the disease. Severity, application site, application time, application method, combined use of chemicals (insecticides, nematicides, acaricides, fungicides, herbicides, plant growth control agents, synergists, soil amendments, etc.) ), the amount and type of fertilizer, etc. The amount is usually from about 0.01% by weight to about 95% by weight based on the total amount of the fungicidal preparation. The fungicidal preparation containing the dithiazide (1) of the present invention as an active ingredient can be produced according to a known process. For example, the dithiazide (1) of the present invention can be mixed with a carrier such as a solid carrier, a liquid carrier, a gaseous carrier or the like. Surfactants and other adjuvants may be added for preparation, as appropriate. Useful carriers can be any of the known carriers commonly used in the art. Examples of solid carriers that can be used are clay (kaolin clay, diatomaceous earth, synthetic hydrated ceria, bentonite, clam clay, acid clay, and the like), talc, ceramics, other inorganic minerals, vermiculite, quartz, sulfur, active Fine powder or granules of carbon, calcium carbonate, hydrated cerium oxide, and the like. Usable liquid carriers are, for example, water, alcohols (eg methanol, ethanol, etc.), ketones (eg acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, ethylbenzene, methyl) Naphthalene, etc.), aliphatic hydrocarbons (such as hexane, cyclohexane, kerosene, light oil, etc.), esters (such as ethyl acetate, butyl acetate, etc.), nitriles (such as acetonitrile, isobutyronitrile, etc.), ethers ( For example, diisopropyl ether, dioxane, etc.), guanamine (such as N,N-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (such as dichloromethane, three Ethyl chloride, carbon tetrachloride, etc.), dimethyl hydrazine, soybean oil, cottonseed oil, vegetable oil, and the like. Examples of useful gaseous carriers (propellants) are butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide, and the like. Examples of useful surfactants are alkyl ester sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylated products thereof, polyethylene glycol ethers, polyol esters, Sugar alcohol compounds and the like. Examples of adjuvants useful for the preparation are fixatives, such as casein, gelatin, polysaccharides (starch powder, gum arabic, cellulosic compounds, alginic acid, etc.), lignin compounds, bentonite, sugars, synthetic water soluble polymers. (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.) and the like; stabilizers such as PAP (acidic isopropyl phosphate), BBH (2,6-di-tert-butyl-4-methylphenol) ), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid, ester thereof, and the like. The fungicidal preparation of the present invention thus obtained can be used as it is or diluted with water. The preparation can be prepared by mixing with any of the following: insecticides, nematicides, acaricides, fungicides, herbicides, plant growth control agents, synergists, soil amendments, and the like. The formulations of the invention can be administered simultaneously with other formulations. When the preparation of the present invention is used as a fungicide for use in agriculture and horticulture, the amount of the preparation of the present invention is not limited and may be appropriately selected according to various conditions, such as the concentration of the active ingredient, the preparation. Form, type of disease to be treated, plant type, severity of disease or aphid, application time, application method, combined use of chemicals (insecticides, nematicides, acaricides, fungicides, herbicides, plants) Growth control agents, synergists, soil amendments, etc.), amount and type of fertilizer, and the like. This amount is usually every 100 m² The area is from about 0.001 g to about 100 g. When a water-diluted emulsion, a wettable powder, a flowable formulation or the like is used, the concentration of the fungicidal or acaricidal formulation is from about 0.1 ppm to about 1000 ppm, preferably from about 1 ppm to 500 ppm. Granules, particles or the like are applied as such without dilution. The compounds of the invention are characterized by excellent fungicidal activity and broad spectrum activity. The compound is useful for controlling plant diseases attributed to pathogenic fungi and resistant pathogenic fungi. Examples of such pathogenic fungi include those which cause the following diseases or are resistant to fungicides for the treatment of the following diseases: rice blast, rice sheath blight, tomato gray mold and the like, apple powdery mildew, apple spots Alternaria blotch, persimmon powdery mildew, grape powdery mildew, barley powdery mildew, wheat powdery mildew, cucumber powdery mildew, cucumber gray mold, tomato late blight, potato late blight and the like. EXAMPLES The invention will be explained in more detail with reference to preparation examples, formulation examples and test examples. The invention is explained in more detail with reference to the following reference examples, manufacturing examples, formulation examples, and test examples. However, the invention is not limited to the examples. In addition, changes may be made without departing from the scope of the invention. Reference example 12- bromine -1-(2- Chlorophenyl ) Preparation of ethyl ketone To a cooled solution of 1-(2-chlorophenyl)ethanone (10.00 g, 64.51 mmol) in diethyl ether (35 ml), EtOAc (3. The resulting reaction mixture was then stirred at 0 ° C for 3 hours. After distilling all the volatiles under reduced pressure, the~~~~~~~~~~~ The combined organic layers were washed with EtOAc EtOAc (EtOAc)EtOAc. It was then used in the next step without further purification.¹ H NMR (CDCl₃ , 400 MHz) δ: 7.57-7.55 (m, 1H), 7.48-7.44 (m, 2H), 7.38-7.36 (m, 1H), 4.52 (s, 2H). Reference example 22- bromine -1-(2- Chlorophenyl ) Preparation of ethanol Add sodium borohydride (1.63 g, 42.91 mmol) to a solution of 2-bromo-1-(2-chlorophenyl)ethanone (10.00 g, 42.91 mmol) in methanol (40 ml) ). The resulting reaction mixture was then stirred at room temperature for 1 hour. After distilling all the volatiles under reduced pressure, the~~~~~~~~~~~~~ The combined organic layers were washed with EtOAc EtOAc (EtOAc)EtOAc. It was then used in the next step without further purification.¹ H NMR (CDCl₃ , 400 MHz) δ: 7.64-7.62 (m, 1H), 7.37-7.33 (m, 1H), 7.28-7.27 (m, 1H), 7.24-7.22 (m, 1H), 5.33-5.30 (m, 1H) , 3.81-3.78 (m, 1H), 3.47-3.42 (m, 1H), 2.71-2.70 (m, 1H). Reference example 3Methanesulfonic acid 2- bromine -1-(2- Chlorophenyl ) Preparation of ethyl ester Triethylamine (6.35 g, 62.92 mmol) was slowly added to a cooled solution of 2-bromo-1-(2-chlorophenyl)ethanol (9.90 g, 41.94 mmol) in THF (35 ml). Methanesulfonium chloride (4.82 g, 41.94 mmol) was then added. The resulting reaction mixture was then stirred at 0 °C for 2 hours. After distilling all the volatiles under reduced pressure, the~~~~~~~~~~~~ The combined organic layers were washed with EtOAc EtOAc m. It was then used in the next step without further purification.¹ H NMR (CDCl₃ , 400 MHz) δ: 7.59-7.54 (m, 1H), 7.42-7.35 (m, 2H), 7.24-7.22 (m, 1H), 6.14-6.11 (m, 1H), 3.78-3.73 (m, 1H) , 3.66-3.63 (m, 1H), 3.08 (m, 3H). Manufacturing example 12-(4-(2- Chlorophenyl )-1,3- Dithiazide 𠷬 -2- Subunit )-2-( Pyridine -3- base ) Acetonitrile (1c-3H and 1c-3L) 2-(Pyridin-3-yl)acetonitrile (0.19 g, 1.59) was slowly added to a stirred solution of potassium hydroxide (0.22 g, 3.97 mmol) in dimethyl hydrazine (3 ml). A solution of dimethyl sulfoxide (1 ml) followed by a solution of carbon disulfide (0.303 g, 3.97 mmol) in dimethyl hydrazine (1 ml). The resulting reaction mixture was then stirred at room temperature for 20 minutes. A solution of 2-bromo-1-(2-chlorophenyl)ethyl methanesulfonate (0.50 g, 1.59 mmol) in dimethyl hydrazine (1 ml) was slowly added to this mixture at room temperature. The reaction mixture was then further stirred at room temperature for 3 hours. The reaction mixture was diluted with ice-cooled distilled water (10 mL) andEtOAc. The combined organic layers were washed with brine, dried over sodium sulfate The crude product thus obtained was purified by column chromatography on a silica gel using a mixture of ethyl acetate and n-hexane as a solvent to obtain a mixture of 0.07 g and 0.11 g of the title compound as a pale yellow solid. Structures 1c-3H and 1c-3L. Using a solvent system of n-hexane and ethyl acetate, the two regioisomers of the title compound can be separated on TLC, and one of the higher Rf values is designated as 1c-3H, while the lower Rf value on TLC is lower. One is designated as 1c-3L. 1c-3H:¹ H NMR (CDCl_3, 400 MHz) δ: 8.83 (s, 1H), 8.54 (d, J = 4.0 Hz, 1H), 7.85-7.82 (m, 1H), 7.65-7.62 (m, 1H), 7.44-7.40 (m, 1H) , 7.35-7.28 (m, 3H), 5.75-5.72 (m, 1H), 3.94-3.89 (m, 1H), 3.74-3.69 (m, 1H). 1c-3L:¹ H NMR (CDCl_3, 400 MHz) δ: 8.84 (s, 1H), 8.54 (d, J = 4.8 Hz, 1H), 7.83-7.83 (m, 1H), 7.71-7.68 (m, 1H), 7.46-7.43 (m, 1H) , 7.37-7.30 (m, 3H), 5.73-5.68 (m, 1H), 3.96-3.89 (m, 1H), 3.74-3.69 (m, 1H). Manufacturing example 2(E&Z)-2-(4-(2- Chlorophenyl )-1,3- Dithiazide 𠷬 -2- Subunit )-2-(6- Chloropyridine -3- base ) Acetonitrile (1c-42) 2-(6-chloropyridin-3-yl)acetonitrile (0.15) was slowly added to a stirred solution of potassium hydroxide (0.13 g, 2.38 mmol) in dimethyl hydrazine (3 ml) at 0 ° C under a nitrogen atmosphere. g, 0.95 mmol) in dimethyl hydrazine (1 ml), followed by a solution of carbon disulfide (0.18 g, 2.38 mmol) in dimethyl hydrazine (1 ml). The resulting reaction mixture was then stirred at room temperature for 20 minutes. A solution of 2-bromo-1-(2-chlorophenyl)ethyl methanesulfonate (0.30 g, 0.95 mmol) in dimethyl hydrazine (1 ml) was slowly added to this mixture at room temperature. The reaction mixture was then further stirred at room temperature for 3 hours. The reaction mixture was diluted with ice-cooled distilled water (10 mL) andEtOAc. The combined organic layers were washed with brine, dried over sodium sulfate The crude product thus obtained was purified by column chromatography on a silica gel using a mixture of ethyl acetate and n-hexane as a solvent, to obtain 0.08 g of a brown viscous oil as two regioisomers. The title compound of the mixture.¹ H NMR (CDCl_3, 400 MHz) δ: 8.62-8.59 (m, 1H), 7.83-7.79 (m, 1H), 7.64-7.50 (m, 1H), 7.45-7.29 (m, 4H), 5.76-5.69 (m, 1H), 3.99-3.90 (m, 1H), 3.79-3.70 (m, 1H). Representative compounds of the invention are illustrated in the following Tables 1 to 5, but the invention is not limited to such compounds. Except for the compounds obtained in the production of Examples 1 and 2, the compounds shown in Tables 1 to 5 were produced by a method similar to that described in the methods or the descriptions set forth in Production Examples 1 and 2. The abbreviations in Tables 1 to 5 are as follows. F: fluorine, Cl: chlorine, Br: bromine, Me: methyl, t-Bu: tert-butyl, CF₃ :trifluoromethyl, Ph: phenyl, NO₂ : nitro, CN: cyano, OMe: methoxy, CF₃ O: trifluoromethoxy, NH₂ : Amine. Table 1: Details of the synthesized compounds belonging to the general structure (1a)*: *H and L herein refer to two regioisomers of a compound having a higher and lower Rf value on TLC, using a solvent system of n-hexane and ethyl acetate, respectively. Table 2: Details of the synthesized compounds belonging to the general structure (1b)*: *H and L herein refer to two regioisomers of a compound having a higher and lower Rf value on TLC, using a solvent system of n-hexane and ethyl acetate, respectively. Table 3: Details of the synthesized compounds belonging to the general structure (1c)*: *H and L herein refer to two regioisomers of a compound having a higher and lower Rf value on TLC, using a solvent system of n-hexane and ethyl acetate, respectively. Table 4: Details of the synthesized compounds belonging to the general structure (1d)*: *H and L herein refer to two regioisomers of a compound having a higher and lower Rf value on TLC, using a solvent system of n-hexane and ethyl acetate, respectively. Table 5: Details of the synthesized compounds belonging to the general structure (1e)*: *H and L herein refer to two regioisomers of a compound having a higher and lower Rf value on TLC, using a solvent system of n-hexane and ethyl acetate, respectively. a compound synthesized by the formula (1)¹ H NMR data are shown in Tables 6 to 10. Table 6 Table 7 Table 8 Table 9 Table 10 Examples of the formulation are given below, wherein the parts are parts by weight. Formulation Example 1 (Emulsible Concentrate) 10 parts of each compound of the present invention were dissolved in 45 parts of Solvesso^® 150 and 35 parts of N-methylpyrrolidone. Add 10 parts of emulsifier to it (trade name: Sorpol^® 3005X, manufactured by Toho Kagaku Co., Ltd.). The ingredients are mixed with agitation to produce a 10% emulsifiable concentrate. Formulation Example 2 (Wettability Powder) 20 parts of each compound of the present invention were added to 2 parts of sodium lauryl sulfate, 4 parts of sodium lignosulfonate, 20 parts of fine powder of aqueous synthetic cerium oxide, and 54 parts of clay. mixture. The ingredients were mixed under agitation by a juicer to produce a 20% wettable powder. Formulation Example 3 (Particles) Five parts of each compound of the present invention were mixed with 2 parts of sodium dodecylbenzenesulfonate, 10 parts of bentonite and 83 parts of clay, followed by thorough agitation. A suitable amount of water is added and the mixture is further stirred. The mixture was granulated by a granulator and air dried to yield 5% granules. Formulation Example 4 (Powder) One part of each compound of the present invention was dissolved in a suitable amount of acetone. To the solution were added 5 parts of a fine powder of aqueous synthetic cerium oxide, 0.3 part of acidic isopropyl phosphate (PAP) and 93.7 parts of clay, followed by mixing and stirring by a juicer. Acetone was removed from it by evaporation to yield a 1% powder formulation. Formulation Example 5 (Flowable Formulation) 20 parts of each compound of the present invention and 20 parts containing 3 parts of polyoxyethylene tristyrylphenyl ether phosphate and triethanolamine and 0.2 part of Rhodorsil^® Mix 426R (made by RhodiaChimie). The mixture was pulverized by a wet method (trade name: DYNO-Mill, manufactured by Willy A. Bachofen AG) and further mixed with 60 parts of water containing 8 parts of propylene glycol and 0.32 parts of xanthan gum. This produces a 20% suspension in water. Test examples are given below to demonstrate that the compounds of the invention are useful as active ingredients in fungicides.Test case 1 ( Fungicidal test against Botrytis cinerea ) A solution of the compound of the invention (500 ppm and 200 ppm) was sprayed onto fresh, healthy cucumber plants at least during the three-leaf stage. The cotyledons of the treated plants were cut and the leaves were placed on a wet tissue paper on a plastic tray. 50 μl spore suspension (1 × 10) using a micropipette⁶ Cfu spores/ml) dripped on the middle of the leaves. Then, a small piece of disc-shaped cotton wool was placed on the spore drop, and 50 μl of the spore suspension was again dropped on the wafer. The leaves were kept at room temperature (20 ° C). The radial growth of the fungus was measured five days after inoculation, and the activity of the compound was shown as a preventive value calculated according to the following equation. Prevention value (%) = {1 - (radial growth on treatment) / (radial growth on control)} × 100. Compounds exhibiting a 50% or greater prophylactic value at a treatment concentration of 500 ppm are as follows: Compound No.: 1c-1, 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c-4H , 1c-4L, 1c-5L, 1c-6L, 1c-8, 1c-8H, 1c-8L, 1c-9, 1c-9H, 1c-9L, 1c-10H, 1c-10L, 1c-11H, 1c -11L, 1c-13H, 1c-13L, 1c-14H, 1c-15H, 1c-16, 1c-16H, 1c-19, 1c-20, 1c-23, 1c-23H, 1c-23L, 1c-24 , 1c-24H, 1c-25H, 1c-25L, 1c-26, 1c-26H, 1c-26L, 1c-27H, 1c-28L, 1c-29H, 1c-29L, 1c-30H, 1c-32H, 1c -32L, 1c-33, 1c-34H, 1c-34L, 1c-35, 1c-35H, 1c-35L, 1d-1H, 1d-6H, 1d-6L, 1d-13, 1d-17, 1d-17H , 1d-17L, 1e-3, 1e-7. Compounds exhibiting a 50% or greater prophylactic value at a treatment concentration of 200 ppm are as follows: Compound No.: 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c-4H, 1c-4L , 1c-5L, 1c-6L, 1c-8, 1c-8H, 1c-8L, 1c-9, 1c-9H, 1c-9L, 1c-10H, 1c-10L, 1c-11H, 1c-13H, 1c -13L, 1c-14H, 1c-15H, 1c-16, 1c-16H, 1c-19, 1c-20, 1c-23, 1c-23H, 1c-23L, 1c-24H, 1c-25H, 1c-25L , 1c-26, 1c-26H, 1c-26L, 1c-27H, 1c-29H, 1c-29L, 1c-32H, 1c-32L, 1c-33, 1c-34H, 1c-34L, 1c-35, 1c -35H.Test case 2 ( Fungicidal test on cucumber powdery mildew ) A solution of the compound of the invention (500 ppm) was sprayed onto fresh, healthy 2 week old cucumber plants. The plants are air-dried and inoculated with a freshly prepared spore suspension (1 × 10)⁶ Cfu spores / ml). The inoculated plants were then placed in a greenhouse (25 ° C, 60% humidity and 16 L 8D). The disease area ratio after 12 days of inoculation was measured, and the activity of the compound was shown as a preventive value calculated according to the following equation. Prevention value (%) = {1 - (processed disease area rate) / (control disease area rate)} × 100. Compounds exhibiting a prophylactic value of 50% or greater are as follows: Compound No.: 1c-1, 1c-1H, 1c-1L, 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c -4H, 1c-4L, 1c-5H, 1c-5L, 1c-6, 1c-6H, 1c-6L, 1c-7H, 1c-7L, 1c-8, 1c-8H, 1c-8L, 1c-9 , 1c-9H, 1c-9L, 1c-10H, 1c-10L, 1c-11H, 1c-11L, 1c-13H, 1c-13L, 1c-14H, 1c-15H, 1c-15L, 1c-16, 1c -16H, 1c-16L, 1c-17H, 1c-18L, 1c-19H, 1c-19L, 1c-20, 1c-21H, 1c-21L, 1c-22H, 1c-23, 1c-23H, 1c-23L , 1c-25H, 1c-25L, 1c-26, 1c-26H, 1c-26L, 1c-27H, 1c-27L, 1c-28H, 1c-28L, 1c-29H, 1c-29L, 1c-30H, 1c -30L, 1c-31H, 1c-31L, 1c-32H, 1c-32L, 1c-33, 1c-34H, 1c-34L, 1c-35, 1c-35H, 1c-35L, 1c-36, 1c-37 , 1c-37, 1c-40H, 1c-40L, 1c-41H, 1c-41L, 1d-1, 1d-1H, 1d-1L, 1d-12, 1d-13, 1d-13L.Test case 3 ( Fungicidal test for Phytophthora infestans ) A solution of the compound of the invention (500 ppm) was sprayed onto fresh, healthy tomato plants at least during the three-leaf stage. The plants are air-dried and inoculated with a freshly prepared sporangia suspension (1 × 10)⁶ Cfu travels spores / ml). The inoculated plants were then placed in a dew chamber (20 ° C and 100% humidity). One day after inoculation, the plants were transferred to a thermostatic chamber (20 ° C, 80% humidity and 16 L8D). The disease area ratio after 5 days of inoculation was measured, and the activity of the compound was shown as a preventive value calculated according to the following equation. Prevention value (%) = {1 - (processed disease area rate) / (control disease area rate)} × 100. Compounds exhibiting a prophylactic value of 50% or greater are as follows: Compound Nos.: 1c-1, 1C-16, 1c-16H, 1c-16L, 1c-19H.Test case 4 ( Magnaporthe oryzae (Pyricularia grisea) Fungicidal test ) A solution of the compound of the invention (500 ppm) was sprayed onto fresh, healthy 2 week old millet plants. The plants are air-dried and inoculated with a freshly prepared spore suspension (1 × 10)⁶ Cfu spores / ml). The inoculated plants were then placed in an open room (25 ° C and 100% humidity). One day after inoculation, the plants were transferred to a thermostatic chamber (25 ° C, 80% humidity and 16 L8D). The disease area ratio after 5-7 days of inoculation was measured, and the activity of the compound was shown as a preventive value calculated according to the following equation. Prevention value (%) = {1 - (processed disease area rate) / (control disease area rate)} × 100. Compounds exhibiting a preventive value of 50% or greater are as follows: Compound No.: 1c-1, 1c-1L, 1c-2H, 1c-2L, 1c-3, 1c-3H, 1c-3L, 1c-4H, 1c -4L, 1c-5H, 1c-5L, 1c-6, 1c-6H, 1c-6L, 1c-8, 1c-8H, 1c-8L, 1c-9, 1c-9H, 1c-9L, 1c-10H , 1c-10L, 1c-11H, 1c-11L, 1c-12, 1c-12H, 1c-13, 1c-13H, 1c-13L, 1c-14H, 1c-15H, 1c-15L, 1c-16, 1c -16H, 1c-16L, 1c-17H, 1c-18L, 1c-19, 1c-19L, 1c-20, 1c-21H, 1c-21L, 1c-23, 1c-23H, 1c-23L, 1c-24 , 1c-24H, 1c-25H, 1c-25L, 1c-26, 1c-26H, 1c-26L, 1c-27H, 1c-30L, 1c-32H, 1c-32L, 1c-34H, 1c-34L, 1c -35, 1c-35H, 1c-35L, 1c-37, 1c-37L, 1c-38H, 1c-38L, 1c-44, 1b-5L, 1d-1H, 1d-1L, 1d-6L, 1d-7 , 1d-7H, 1d-7L, 1d-8, 1d-11, 1d-11H, 1d-11L, 1d-12L, 1d-15, 1d-16, 1d-16H, 1d-16L, 1d-17, 1d -17H, 1e-6. (Note) As described above, the present invention is illustrated by the preferred embodiments of the present invention. However, it should be understood that the scope of the invention should be construed only by the scope of the claims. It is to be understood that the patents, patent applications, and documents cited herein are hereby incorporated by reference in their entirety in their entirety in their entirety herein The present application claims priority to Indian Patent Application No. 201711008910, filed on March 15, 2017, to the Indian Patent Office (Intellectual Property India), the entire contents of which are incorporated by reference. The manner is incorporated herein. Industrial Applicability The dithiazide compound of the present invention has an antibacterial effect against plant diseases and can be used as an active ingredient of a plant control agent.

Claims (14)

A dithiazide compound represented by formula (1): Or a salt thereof or an N-oxide thereof, wherein R ¹ , R ² and R ^{3 are the} same or different and each represents hydrogen, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkane Oxy, C _1-6 haloalkoxy, C _1-6 alkoxy C _1-6 alkyl, C _1-6 haloalkoxy C _1-6 alkyl, C _2-6 alkenyl, C _2-6 Haloalkenyl, C _2-6 alkynyl, C _2-6 haloalkynyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, optionally substituted aryl And optionally substituted heteroaryl or optionally substituted heterocyclic group, the two of the R ¹ , R ² and R ³ groups together may form a ring via or without at least one hetero atom, denoted as R ¹ The groups of R ² and R ³ may be further substituted as appropriate; Y ¹ represents an optionally substituted aryl group, optionally substituted pyridyl group, optionally substituted pyrazinyl group, optionally substituted Pyrimidinyl or optionally substituted pyridazinyl; Y ₂ represents optionally substituted aryl or optionally substituted heteroaryl; Q represents hydrogen, nitro, cyano, C _1-6 alkyl, C _1-6 haloalkyl, C _3-8 cycloalkyl, C _3-8 cycloalkyl C _1-6 alkyl, C _1-6 alkylcarbonyl, C _1-6 halogenated Alkylcarbonyl, C _3-8 cycloalkylcarbonyl, C _1-6 alkoxycarbonyl, C _1-6 haloalkoxycarbonyl, C _3-8 cycloalkoxycarbonyl, C _1-6 alkylthio, C _1-6 haloalkylthio, C _3-8 cycloalkylthio, C _3-8 cycloalkyl C _1-6 alkylthio, C _1-6 alkoxy C _1-6 alkylthio, C _{1 -6} alkylsulfonyl, C _1-6 alkylsulfinylene, C _1-6 haloalkylsulfonyl, C _1-6 haloalkylsulfinyl, C _3-8 cycloalkylsulfonyl , C _3-8 cycloalkylsulfinyl, C _3-8 cycloalkyl C _1-6 alkylsulfonyl, C _3-8 cycloalkyl C _1-6 alkylsulfinylene, optionally Substituted arylthio, optionally substituted aryl C _1-6 alkylthio, optionally substituted arylsulfonyl, optionally substituted arylsulfinyl, optionally substituted An aryl group, optionally substituted heteroaryl or optionally substituted heterocyclic group. The thiazide compound according to claim 1 or a salt thereof or an N-oxide thereof, wherein R ¹ , R ² and R ^{3 are the} same or different and each represents hydrogen, halogen or C _1-6 alkyl. The thiazide compound according to claim 1 or 2, wherein R ¹ , R ² and R ^{3 are the} same or different and each represents hydrogen or a C _1-6 alkyl group, or a salt thereof or an N-oxide thereof. The dithiaxanthene compound of any one of claims 1 to 3, or a salt thereof, or an N-oxide thereof, wherein Y ¹ is optionally substituted aryl or optionally substituted pyridyl. The dithiaxanthene compound of any one of claims 1 to 4, or a salt thereof, or an N-oxide thereof, wherein Y ¹ is optionally substituted pyridyl. The dithiazide compound according to any one of claims 1 to 5, or a salt thereof or an N-oxide thereof, wherein Y ¹ represents: , where * is the point of attachment to the parent compound. The dithiazide compound according to any one of claims 1 to 5, or a salt thereof or an N-oxide thereof, wherein Y ¹ represents: , where * is the point of attachment to the parent compound. The dithiazide compound according to any one of claims 1 to 5, or a salt thereof or an N-oxide thereof, wherein Y ¹ represents: , where * is the point of attachment to the parent compound. The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of claims 1 to 8, wherein Y ² is an optionally substituted aryl group. The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of claims 1 to 8, wherein Y ² is optionally substituted heteroaryl. The dithiaxanthene compound or a salt thereof or an N-oxide thereof according to any one of claims 1 to 8 and 10, wherein the Y ² is selected from the group consisting of: , and And * is the point of attachment to the parent compound. The dithiaxanthene compound of any one of claims 1 to 11 or a salt thereof or an N-oxide thereof, wherein the Q is a cyano group. A plant disease controlling agent comprising the dithiazide compound according to any one of claims 1 to 12, or a salt thereof or an N-oxide thereof. A fungicide comprising the dithiazide compound according to any one of claims 1 to 12, or a salt thereof or an N-oxide thereof.