TW201831457A - Novel fungicidal carbamate compounds - Google Patents

Abstract

An object of the present invention is to provide a carbamate compound or a salt thereof that controls diseases. The present invention provides a carbamate compound represented by Formula (1): or a salt thereof, wherein R1, R3 and R6 are identical or different and each represents hydrogen, or the like; R2 represents hydrogen, halogen, or C1-6 alkyl; R4 and R5 are identical or different and each represents hydrogen, or the like; R7 represents hydrogen, or the like; R8 represents hydrogen, or C1-6 alkyl; X and X1 independently represent oxygen, or sulfur; Y represents oxygen, or sulfur; Z represents oxygen, or sulfur; l is an integer of 0 to 2; m is an integer of 0 to 3; n is an integer of 0 to 4; and when l, m or n is more than one, the l, m or n may be the same or different.

Description

Novel fungicidal urethane compound

This invention relates to novel urethane compounds and methods of making the same. The invention further provides agricultural and horticultural fungicide compositions comprising the compounds.

In recent years, control of resistant fungi has not been achieved by the use of known fungicides. The development of resistance to various fungi is mainly due to the long-term and extensive use of known fungicides. Therefore, there is a need to develop novel compounds having fungicidal activity against resistant fungi. WO 2015/147314 (Patent Literature (PTL) 1) and WO 2015/147336 (Patent Document (PTL) 2) disclose a compound represented by the formula (A) which has a pyrazole moiety in a molecule. These publications also mention that the compounds represented by formula (A) are useful as fungicides to control plant diseases. Wherein R ₁ is halogen, C ₁ -C ₄ alkyl; R ₂ is hydrogen, halogen, C ₁ -C ₄ alkyl; R ₃ is hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ Alkoxy, C ₃ -C ₄ cycloalkyl; Z is halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy; Q is represented by Q ₁ , Q ₂ and Q _{3 as} shown below : Wherein R ₄ is C ₁ -C ₃ alkyl; R ₅ is hydrogen, hydroxy, methyl; R ₆ is hydrogen, hydroxy, methyl, methoxy; X ₁ is oxygen, sulfur; X ₂ is oxygen, NR ₇ or a direct bond; R ₇ is hydrogen, C ₁ -C ₃ alkyl. However, such publications do not relate to the compounds of the invention. Citation List Patent Literature PTL 1: WO 2015/147314 PTL 2: WO 2015/147336

Solution to Problem The present invention provides novel urethane compounds which exhibit excellent fungicidal activity against resistant fungi as well as drug allergic fungi. The invention also provides a process for the preparation of such urethane compounds. The present invention further provides a novel fungicide for agriculture and horticulture which exhibits a significant fungicidal action against chemically resistant fungi as well as chemically allergic fungi. Specifically, the present inventors conducted intensive studies and successfully synthesized a compound represented by the following formula (1) or a salt thereof having fungicidal activity. The inventors have conducted further research based on the above results. The invention has thus been achieved. More specifically, the present invention includes the following examples: Item 1: The urethane compound is represented by the formula (1): Or a salt thereof, wherein R ₁ , R ₃ and R _{6 are the} same or different and each represents hydrogen, halogen, nitro, cyano, hydroxy, formamyl, carboxy, 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 a C _{1 - 6} alkyl group, a C _{1 - 6} alkoxycarbonyl group, a C _{1 - 6} haloalkyloxycarbonyl group, a cyano C _{1 - 6} alkyl group, a cyano C _{1 - 6} alkoxy group, a C _{2 - 6} alkenyl group , C _{2 - 6} alkenyl, halo, cyano, C _{2 - 6} alkenyl, C _{2 - 6} alkynyl, C _{2 - 6} alkynyl, halo, 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} cycloalkyl group, 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} halosulfonyl, C _{1 - 6} acyl halide alkylsulfinyl, C _{3 - 8} cycloalkyl sulfo acyl, C _{3 - 8} cycloalkyl acyl alkylsulfinyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkyl sulfonic acyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkylsulfinyl acyl, C _{2 - 6} alkenyloxy, C _{2 - 6} alkynyl group, C _{2 - 6} alkenyloxy halo , C _{2 - 6} alkynyl group halogen, C _{1 - 6} alkylsulfonyl group, C _{1 - 6} alkylsulfinyl acyl group, C _{1 - 6} alkylcarbonyl, C _{1 - 6} haloalkyl carbonyl, 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 a substituted arylsulfinyloxy group, optionally substituted aryl, or optionally substituted heteroaryl; R ₂ represents hydrogen, halogen or C _{1 - 6} alkyl; R ₄ and R _{5 are the} same Or different, and each represents hydrogen, halogen or C _{1 - 6} alkyl; R ₇ represents hydrogen, hydroxy, formyl, cyano, 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} haloalkyl carbonyl, C _{1 - 6} alkoxycarbonyl C _{2 - 6} haloalkoxy-carbonyl group, C _{2 - 6} alkenyl, C _{2 - 6} haloalkenyl, C _{2 - 6-cyano-alkenyl,} C _{2 - 6} alkynyl, C _{2 - 6} haloalkynyl, C _{2 - 6} cyanoalkynyl, C _{1 - 6} alkylsulfonyl, C _{1 - 6} alkylsulfinyl, C _{1 - 6} halosulfonyl, C _{1 - 6} haloalkyl sulfinyl, C _3--8 sulfo cycloalkyl acyl, C _{3 - 8} cycloalkyl acyl alkylsulfinyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkyl sulfonic acyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkyl Sulfosyl, optionally substituted arylsulfonyl, optionally substituted arylsulfinyl, or optionally substituted aryl; R ₈ represents hydrogen or C _{1 - 6} alkyl; X and X ₁ independently represents oxygen or sulfur; Y represents oxygen or sulfur; Z represents oxygen or sulfur; l is an integer from 0 to 2; m is an integer from 0 to 3; n is an integer from 0 to 4; Or when n is greater than one, l, m or n may be the same or different. Item 2: The amine Paragraph 1-carboxylate or a salt thereof, wherein R ₁ is independently hydrogen, halogen, nitro, C _{1 - 6} alkyl, C _{1 - 6} haloalkyl, C _{1 - 6} alkoxycarbonyl, cyano C _{1 - 6} alkyl, optionally substituted aryl. Item 3: The amine of the preceding items of any one carboxylate compound or a salt thereof, wherein R ₂ is hydrogen or C _{1 - 6} alkyl. The urethane compound or a salt thereof according to any one of the preceding claims, wherein R _{3 is} each independently hydrogen, halogen or C _{1 - 6} alkyl. Item 5: The amine of the preceding items of any of a carboxylic acid ester or a salt thereof, wherein R ₄ and R ₅ each represents hydrogen or C _{1 - 6} alkyl. Item 6: The amine of the preceding items of any one carboxylate compound or a salt thereof, wherein R ₆ are each independently hydrogen, halogen, C _{1 - 6} alkyl or C _{1 - 6} alkoxy. Item 7: The amine of the preceding items of any one carboxylate compound or a salt thereof, wherein R ₇ is hydrogen, C _{1 - 6} alkyl or C _{1 - 6} alkylcarbonyl. The urethane compound or a salt thereof according to any one of the preceding claims, wherein R ₈ is a C _{1 - 6} alkyl group. Item 9. The urethane compound or a salt thereof according to any one of the preceding claims, wherein X and X ₁ are oxygen. The urethane compound or a salt thereof according to any one of the preceding claims, wherein Y is oxygen. The urethane compound or a salt thereof, wherein Z is sulfur, and the 1,3-thiazole ring containing Z is selected from the group consisting of: And * is the point of attachment to the parent compound. Item 12: The amine of the preceding items of any one carboxylate compound or a salt thereof, wherein each R _{1 is} independently hydrogen, halogen, C _{1 - 6} alkyl or C _{1 - 6} haloalkyl. Item 13: The amine of the preceding items of any one carboxylate compound or a salt thereof, wherein R ₂ is C _{1 - 6} alkyl. Item 14. The urethane compound or a salt thereof according to any one of the preceding claims, wherein R ₂ is a methyl group. Item 15. The urethane compound or a salt thereof according to any one of the preceding claims, wherein each R ₃ is hydrogen. The urethane compound or a salt thereof according to any one of the preceding claims, wherein R ₄ and R ₅ each represent hydrogen. Item 17: The amine of the preceding items of any one carboxylate compound or a salt thereof, wherein R ₆ is hydrogen, halogen or C _{1 - 6} alkyl. Item 18: The amine of the preceding items of any one carboxylate compound or a salt thereof, wherein R ₇ is hydrogen or C _{1 - 6} alkylcarbonyl. The urethane compound or a salt thereof according to any one of the preceding claims, wherein R ₈ is methyl or ethyl. The urethane compound or a salt thereof according to any one of the preceding claims, wherein R ₈ is a methyl group. The urethane compound or a salt thereof according to any one of the preceding claims, wherein the 1,3-thiazole ring is: , and * is the point of attachment to the parent compound. Item 22. The urethane compound or a salt thereof according to any one of the preceding claims, wherein the carbamate compound is represented by the formula (1A): . The urethane compound or a salt thereof according to any one of the preceding claims, wherein the 1,3-thiazole ring is: , and * is the point of attachment to the parent compound. The urethane compound or a salt thereof according to any one of the preceding claims, wherein the 1,3-thiazole ring is: , and * is the point of attachment to the parent compound. Item 25: The urethane compound is selected from the group consisting of Compounds 1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A-9, 1A-10, 1A-12, 1A-13, 1A-14, 1A-15, 1A-16, 1A-17, 1A-18, 1A-22, 1A-25, 1A-28, 1A-29, 1A-30, 1A- 31, 1A-32, 1A-33, 1A-34, 1A-35, 1A-36, 1A-37, 1A-38, 1A-39, 1A-40, 1A-41, 1A-42, 1A-43, 1A-44, 1A-45, 1A-46, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1 and 1C-2 or a salt thereof . Item 26: The carbamate compound is selected from the group consisting of compounds 1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A-9, 1A-10, 1A-12, 1A-13, 1A-14, 1A-15, 1A-16, 1A-17, 1A-18, 1A-22, 1A-23, 1A-25, 1A-29, 1A-30, 1A- 33, 1A-34, 1A-37, 1A-38, 1A-39, 1A-40, 1A-41, 1A-42, 1A-46, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1 and 1C-2 or a salt thereof. Item 27: The carbamate compound is selected from the group consisting of compounds 1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A-9, 1A-10, 1A-12, 1A-13, 1A-14, 1A-15, 1A-17, 1A-18, 1A-25, 1A-29, 1A-30, 1A-33, 1A-37, 1A-38, 1A- 39, 1A-40, 1A-41, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1 and 1C-2 or a salt thereof. Item 28: The carbamate compound is selected from the group consisting of Compounds 1A-4, 1A-5, 1A-12, 1A-15, 1A-17, 1A-29, 1A-35, 1A-36, 1A-37, 1A-40, 1A-49, 1C-1 and 1C-2 or a salt thereof. Item 29: The carbamate compound is selected from the group consisting of Compounds 1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A-7, 1A-9, 1A-10, 1A-11, 1A-12, 1A-13, 1A-14, 1A-15, 1A-17, 1A-18, 1A-19, 1A-20, 1A-22, 1A-23, 1A- 25, 1A-26, 1A-29, 1A-30, 1A-33, 1A-35, 1A-36, 1A-37, 1A-38, 1A-39, 1A-40, 1A-41, 1A-42, 1A-43, 1A-44, 1A-45, 1A-46, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1 and 1C- 2 or its salt. Item 30: A plant disease controlling agent comprising the urethane compound of any one of items 1 to 29 or a salt thereof. Item 31: A fungicide comprising the urethane compound of any one of items 1 to 29 or a salt thereof. Advantageous Effects of Invention The urethane compound or a salt thereof according to the present invention achieves an excellent fungicidal action against fungal plant pathogens. Further, the heterocyclic compound or a salt thereof according to the present invention is suitably used as a novel fungicide which exhibits excellent fungicidal activity not only against chemical allergic fungi but also against chemical resistant fungi.

Hereinafter, the present invention will be described in more detail with reference to examples, but the technical scope of the present invention is not limited to the examples. Throughout the specification, unless expressly stated otherwise, the singular expression should be understood to encompass the concept in the plural. Therefore, singular items (for example, in the case of English, "a", "the", and the like) are also understood to encompass the concept in the plural. Moreover, the terms used herein are to be understood as being used in the ordinary meanings of the art unless specifically stated otherwise. Therefore, unless otherwise defined, all terms and technologies used herein have the same meaning as the terms commonly understood by those skilled in the art. In the case of conflicts, this specification (including definitions) is preferred.Carbamate compound or salt thereof The present invention provides a urethane compound represented by the formula (1) or a salt thereof for use in agriculture and horticulture.Where R₁ , R₂ , R₃ , R₄ , R₅ , R₆ , R₇ , R₈ , X, X₁ , Y, Z, l, m and n are as defined above. Subsequently, the terms in the present specification are described below. In the present invention, the number of substituents of the group defined by "optionally substituted" or "substituted" is not particularly limited, if the group is substitutable and is one or plural. In addition, unless otherwise indicated, the description of each group is also applied when the group is a moiety of one or the other group. "C_{1 - 6} "Alkyl" means a straight or branched saturated hydrocarbon group having from one to six carbon atoms. "C_{2 - 6} "Alkenyl" means a straight or branched chain unsaturated hydrocarbon group having from two to six carbon atoms and containing from 1 to 3 double bonds. "C_{2 - 6} "Alkynyl" means a straight or branched chain unsaturated hydrocarbon group having two to six carbon atoms and containing one triple bond. "C_{3 - 8} "Cycloalkyl" means a cycloalkyl group having three to eight carbon atoms and includes those cycloalkyl groups having a partially bridged structure. "C_{1 - 6} "Alkoxy" means "C_{1 - 6} Alkoxy", and "C_{1 - 6} "Alkyl" part and "C described above"_{1 - 6} The alkyl group has the same definition. "Aryl" means a monocyclic or polycyclic aromatic hydrocarbon. "Heterocycle" 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 ring member atoms of the heteroaryl group are excluded The carbon atom includes 1, 2, 3 or 4 hetero atoms selected from N, O and S. Specific examples of the groups as used in the present specification are shown below. Examples of the halogen 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 particularly limited to, C_{1 - 6} a linear or branched alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, t-butyl, n-pentyl, n-hexyl and the like Group. C_{1 - 6} Examples of the haloalkyl group include, but are not particularly limited to, C substituted with 1 to 9, preferably 1 to 5 halogen atoms._{1 - 6} A linear or branched alkyl group 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 particularly limited to, C_{1 - 6} a linear or branched alkoxy group such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, second butoxy, tert-butoxy and Its similar group. C_{1 - 6} Examples of the haloalkoxy group include, but are not particularly limited to, C substituted with 1 to 9, preferably 1 to 5, halogen atoms._{1 - 6} Linear or branched alkoxy such as fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoro Ethoxy, pentafluoroethoxy, 3,3,3-trifluoropropoxy, 4,4,4-trifluorobutoxy, heptafluoroisobutoxy and the like. C_{1 - 6} Alkoxy C_{1 - 6} Examples of the alkyl group include not particularly limited to C_{1 - 6} Linear or branched alkyl group 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 And similar groups. 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 fluoromethoxymethyl, chloromethoxymethyl , bromomethoxymethyl, iodomethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 2,2,2-trifluoroethoxymethyl and the like . C_{3 - 8} Examples of the cycloalkyl group include, but are not particularly limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. C_{3 - 8} Cycloalkyl C_{1 - 6} Examples of the alkyl group include, but are not particularly limited to, a cyclopropylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, and the like. C_{1 - 6} Examples of alkylcarbonyl groups include, but are not particularly limited to, C_{1 - 6} a linear or branched alkylcarbonyl group such as methylcarbonyl (ethenyl), ethylcarbonyl (propyl), n-propylcarbonyl (butylidene), isopropylcarbonyl (isobutyl), n-butylcarbonyl ( Pentamidine), isobutylcarbonyl (isoamyl), t-butylcarbonyl, tert-butylcarbonyl and the like. C_{1 - 6} Examples of the haloalkylcarbonyl group include, but are not particularly limited to, C substituted with 1 to 9, and preferably 1 to 5, halogen atoms._{1 - 6} a linear or branched alkylcarbonyl group such as fluoromethylcarbonyl, chloromethylcarbonyl, bromomethylcarbonyl, iodomethylcarbonyl, dichloromethylcarbonyl, trichloromethylcarbonyl, difluoromethylcarbonyl, trifluoro Methylcarbonyl, chlorodifluoromethylcarbonyl, bromodifluoromethylcarbonyl, dichlorofluoromethylcarbonyl, 2,2,2-trichloroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, five Fluoroethyl carbonyl and the like. C_{1 - 6} Examples of alkoxycarbonyl groups include, but are not particularly limited to, C_{1 - 6} a linear or branched alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, second butoxycarbonyl , a third butoxycarbonyl group and the like. C_{1 - 6} Examples of the haloalkyloxycarbonyl group include, but are not particularly limited to, C substituted with 1 to 9, preferably 1 to 5, halogen atoms._{1 - 6} a straight or branched alkoxycarbonyl group such as fluoromethoxycarbonyl, chloromethoxycarbonyl, bromomethoxycarbonyl, iodomethoxycarbonyl, dichloromethoxycarbonyl, trichloromethoxycarbonyl, difluoro Methoxycarbonyl, trifluoromethoxycarbonyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 4,4, 4-Trifluorobutoxycarbonyl, heptafluoroisopropoxycarbonyl and the like. Cyano C_{1 - 6} Examples of the alkyl group include, but are not particularly limited to, C substituted by a cyano group_{1 - 6} Linear or branched alkyl group, such as cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-isopropyl, cyano-n-butyl, cyano-isobutyl, cyano- Second butyl, cyano-t-butyl, cyano-n-hexyl and the like. Cyano C_{1 - 6} Examples of alkoxy groups include C substituted by a cyano group_{1 - 6} a linear or branched alkoxy group such as cyanomethoxy, cyanoethoxy, cyano-n-propoxy, cyano-isopropoxy, cyano-n-butoxy, cyano-iso Butoxy, cyano-second butoxy, cyano-tert-butoxy, cyano-hexyloxy and the like. C_{2 - 6} Examples of the alkenyl group include, but are not particularly limited to, a vinyl group, an allyl group, a 2-butenyl group, a 3-butenyl group, a 1-methallyl group, and the like. C_{2 - 6} Examples of the haloalkenyl group 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-butyl Alkynyl groups and the like. C_{2 - 6} Examples of the haloalkynyl group include, but are not particularly limited to, a fluoroethynyl group, a bromoethynyl group, a chloroethynyl group, an iodoethynyl group, a 3,3,3-trifluoro-1-propynyl group, 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-ene Base, 4-cyano-3-butenyl, 4,4-dicyano-3-butenyl, 4,4,4-tricyano-2-butenyl and the like. Cyano C_{2 - 6} Examples of the alkynyl group include, but are not particularly limited to, a cyanoethynyl group, a 3-cyano-1-propynyl group, and the like. C_{1 - 6} Examples of alkanesulfonyl groups include, but are not particularly limited to, C_{1 - 6} Linear or branched alkanesulfonyl, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, second butanesulfonate Base, tributyl sulfonyl group and the like. C_{1 - 6} Examples of the halosulfonyl group include, but are not particularly limited to, fluoromethanesulfonyl, chloromethanesulfonyl, bromomethylsulfonyl, iodomethylsulfonyl, chloromethanesulfonyl, trichloromethanesulfonyl. ,difluoromethanesulfonyl, trifluoromethanesulfonyl, chlorodifluoromethanesulfonyl, bromodifluoromethanesulfonyl, dichlorofluoromethanesulfonyl, 2,2,2-trichloroethanesulfonate Base, 2,2,2-trifluoroethanesulfonyl, pentafluoroethanesulfonyl and C substituted by 1 to 9, and preferably 1 to 5 halogen atoms_{1 - 6} Linear or branched alkanesulfonyl. C_{1 - 6} Examples of the alkylsulfinyl group include, but are not particularly limited to, C_{1 - 6} A linear or branched alkyl sulfinylene group, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl , isobutylsulfinyl, t-butylsulfinyl, tert-butylsulfinyl and the like. C_{1 - 6} Examples of the haloalkylsulfinyl group 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 Sulfonyl, trichloromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl , dichlorofluoromethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl and Its similar group. C_{1 - 6} Examples of alkylthio groups include, but are not particularly limited to, C_{1 - 6} a linear or branched alkylthio group such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, second butylthio, tert-butylthio and Its similar group. C_{1 - 6} Examples of the haloalkylthio group 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 such as fluoromethylthio, chloromethylthio, bromomethylthio, iodomethylthio, dichloromethylthio, trichloromethylthio, difluoromethylthio, trifluoro Methylthio, chlorodifluoromethylthio, bromodifluoromethylthio, dichlorofluoromethylthio, 2,2,2-trichloroethylthio, 2,2,2-trifluoroethylthio, five Fluoroethylthio groups and the like. C_{3 - 8} Examples of the cycloalkylsulfonyl group include, but are not particularly limited to, a cyclopropanesulfonyl group, a cyclobutsulfonyl group, a cyclopentylsulfonyl group, a cyclohexylsulfonyl group, and the like. C_{3 - 8} Examples of the cycloalkylsulfinyl group include, but are not particularly limited to, a cyclopropylsulfinyl group, a cyclobutylsulfinyl group, a cyclopentylsulfinyl group, a cyclohexylsulfinyl group, and the like. . C_{3 - 8} Examples of the cycloalkylthio group include, but are not particularly limited to, a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, and the like. C_{3 - 8} Cycloalkyl C_{1 - 6} Examples of the alkanesulfonyl group include, but are not particularly limited to, cyclopropylmethylsulfonyl, 2-cyclopropylethylsulfonyl, 3-cyclopropylpropanesulfonyl, cyclohexylmethanesulfonyl, and the like. group. C_{3 - 8} Cycloalkyl C_{1 - 6} Examples of the alkylsulfinyl group include, but are not particularly limited to, cyclopropylmethylsulfinyl, 2-cyclopropylethylsulfinyl, 3-cyclopropylsulfinyl, cyclohexyl. Methyl sulfinylene and its like. C_{3 - 8} Cycloalkyl C_{1 - 6} Examples of the alkylthio group include, but are not particularly limited to, a cyclopropylmethylthio group, a 2-cyclopropylethylthio group, a 3-cyclopropylpropylthio group, a cyclohexylmethylthio group, and the like. C_{1 - 6} Alkoxy C_{1 - 6} Examples of alkylthio groups include, but are not particularly 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-butyl Oxymethylthio group, second butoxymethylthio group, tert-butoxymethylthio group, 2-methoxyethylthio group and the like. C_{2 - 6} Examples of the alkenyloxy group include, but are not particularly limited to, a vinyloxy group, a 1-propenyloxy group, an isopropenyloxy group, an allyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, a 1-methylene group. Propyloxy and the like. C_{2 - 6} Examples of the haloalkoxy group include, but are not particularly limited to, 2,2-dichloroethyleneoxy, 2,2-dibromoethenyloxy, 2,2-difluoroethyleneoxy, 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 groups 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 groups include, but are not particularly limited to, fluoroethynyloxy, bromoethynyloxy, chloroethynyloxy, iodoethynyloxy, 3,3,3-trifluoro-1-propynyloxy and the like. Group. C_{1 - 6} Examples of alkylsulfonyloxy groups include, but are not particularly limited to, C_{1 - 6} Linear or branched alkanesulfonyl group, such as methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, iso Butylsulfonyloxy, t-butylsulfonyloxy, tert-butylsulfonyloxy and the like. C_{1 - 6} Examples of the alkylsulfinyloxy group include, but are not particularly limited to, C_{1 - 6} A linear or branched alkylsulfinyloxy group, such as methylsulfinyloxy, ethylsulfinyloxy, n-propylsulfinyloxy, isopropylsulfinyloxy, n-butyl A sulfinyloxy group, an isobutylsulfinyloxy group, a t-butylsulfinyloxy group, a tert-butylsulfinyloxy group, and the like. Examples of the substituted or unsubstituted amino group include, but are not particularly limited to, an amine group, a monoalkylamino group, a dialkylamino group, a monodecylamino group, and the like. Examples of alkyl groups include the C mentioned above_{1 - 6} Alkyl groups and the like. Examples of sulfhydryl groups include the C mentioned above_{1 - 6} Alkoxycarbonyl, haloalkyloxycarbonyl, arylcarbonyl and the like. Examples of the aryl group include, but are not particularly limited to, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and the like. Aryl C_{1 - 6} Examples of the alkyl group include, but are not particularly limited to, a benzyl group, a phenethyl group, a phenyl-n-propyl group, and the like. These aryl C_{1 - 6} The alkyl group may be further substituted in both the alkyl group and the aryl group. Examples of the aryloxy group include, but are not particularly limited to, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, 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 Base and its like. Examples of the heteroaryloxy group include, but are not particularly limited to, a pyridyloxy group, a pyrimidinyloxy group, a pyrazolyloxy group, and the like. Heteroaryl C_{1 - 6} Examples of the alkoxy group include, but are not particularly limited to, a pyridylmethoxy group, a pyridylethoxy group, a pyrimidinylethoxy group, a pyrazolylmethoxy group, and the like. Examples of the arylsulfonyl group include, but are not particularly limited to, a benzenesulfonyl group, a 1-naphthalenesulfonyl group, a 2-naphthalenesulfonyl group, and the like. Examples of the arylsulfinyl group include, but are not particularly limited to, a phenylsulfinylene group, a 1-naphthylsulfinyl group, a 2-naphthylsulfinyl group, and the like. Examples of the arylthio group include, but are not particularly limited to, a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, 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, a phenylsulfinyloxy group, a 1-naphthylsulfinyloxy group, a 2-naphthylsulfinyloxy group, and the like. Aryl C_{1 - 6} Examples of the alkylthio group include, but are not particularly limited to, benzylthio, phenethylthio, phenyl-n-propylthio, phenyl-n-butylthio, 1-naphthylthio, 2-naphthylthio. And similar groups. Examples of heteroaryl groups include, but are not particularly limited to, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, thiadipine Azyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, isodecyl, oxazolyl, quinazolinyl , carbazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzisothiazolyl, benzimidazolyl, quinolyl, isoquinolyl, pyridoindoleyl, hydrazine A phenyl group, a pyridazinyl group, a quinoxalinyl group, a fluorenyl group, a phenothiazine group, a benzofuranyl group, a decyl group, a benzothienyl group, 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 the heterocyclic group include, but are not particularly limited to, thienyl, furyl, tetrahydrofuranyl, dioxolanyl, dioxanyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, iso Oxazolyl, oxazolyl, oxazolidinyl, isoxazolinyl, thiazolyl, isothiazolyl, thiazolinyl, thiazolidinyl, isothiazolinyl, pyrazolyl, pyrazolyl, imidazole , dihydroimidazolyl, tetrahydroimidazolyl, oxadiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, triazolinyl, triazolyl, tetrazolyl, tetrazoline Base, pyridyl, dihydropyridyl, tetrahydropyridyl, piperidinyl, oxazinyl, dihydrooxazinyl, N-morpholinyl, thiazinyl, dihydrothiazinyl, thia N-morpholine Base, pyridazinyl, dihydropyridazinyl, tetrahydropyridazinyl, hexahydroazinyl, oxadiazinyl, dihydrooxadiazinyl, tetrahydrooxazinyl, thiadiazolyl, thiazepine Azinyl, dihydrothiazinyl, tetrahydrothiazinyl, pyrimidinyl, dihydropyrimidinyl, tetrahydropyrimidinyl, hexahydropyrimidinyl, pyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl , piperazinyl, triazinyl, Dihydrotriazinyl, tetrahydrotriazinyl, hexahydrotriazinyl, tetrazinyl, dihydrotetrazinyl, fluorenyl, indanyl, isodecyl, oxazolyl, quinazoline , dihydroquinazolyl, tetrahydroquinazolyl, oxazolyl, benzoxazolyl, benzoxazolinyl, benzisoxazolyl, benzisoxazolinyl, benzothiazolyl, Benzoisothiazolyl, benzisothiazolinyl, benzimidazolyl, oxazolinyl, quinolyl, dihydroquinolinyl, tetrahydroquinolyl, isoquinolinyl, dihydroisoquinolinyl , tetrahydroisoquinolyl, pyridoindoleyl, tetrahydrobenzoxazinyl, porphyrinyl, dihydroporphyrinyl, tetrahydroporphyrinyl, pyridazinyl, dihydropyridazinyl, tetrahydrogen Pyridazinyl, quinoxalinyl, dihydroquinoxalinyl, tetrahydroquinoxalinyl, fluorenyl, dihydrobenzotriazinyl, dihydrobenzotetrazinyl, phenothiazine furyl, benzene And furyl, decyl, benzothienyl and the like. Such heterocyclic groups include those substituted with a pendant oxy or thioketo group at any substitutable position. All of the heterocyclic compounds 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, formamyl, 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, arylcarbonyl, aryloxycarbonyl, C_{1 - 6} Alkoxycarbonyl, C_{1 - 6} Haloalkoxycarbonyl, 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} Alkyl sulfinyloxy, 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. In these, preferred substituents are halogen, nitro, cyano, C_{1 - 6} Alkyl, C_{1 - 6} Haloalkyl, C_{1 - 6} Alkoxy, C_{1 - 6} Haloalkoxy, C_{1 - 6} Alkylsulfonyl, C_{1 - 6} Haloalkylsulfonyl, C_{1 - 6} Alkylsulfinyl, C_{1 - 6} Haloalkylsulfinyl, C_{1 - 6} Alkylthio, C_{1 - 6} Haloalkylthio, substituted or unsubstituted amino, aryl and heterocyclic, and more preferred substituents are fluoro, chloro, nitro, methyl, ethyl, trifluoromethyl, methoxy and Fluoromethoxy. Preferably, the substituted aryl group is a halogen-substituted aryl group, via C_{1 - 6} Alkyl substituted aryl, via C_{1 - 6} Haloalkyl substituted aryl, halogen and C_{1 - 6} Haloalkyl substituted aryl, via C_{1 - 6} Alkoxy-substituted aryl, via C_{1 - 6} Haloalkoxy substituted aryl group and C_{1 - 6} An alkylthio substituted aryl group. More preferably substituted aryl is chloro substituted aryl, fluoro substituted aryl, trifluoromethyl substituted aryl, chloro and trifluoromethyl substituted aryl, trifluoromethoxy Substituted aryl and methoxy substituted aryl and methylthio substituted aryl. Preferably, the substituted heteroaryl group is a halogen-substituted heteroaryl group, via C_{1 - 6} Alkyl substituted heteroaryl, via C_{1 - 6} Haloalkyl substituted heteroaryl, halogen and C_{1 - 6} Haloalkyl substituted heteroaryl, via C_{1 - 6} Alkoxy substituted heteroaryl, via C_{1 - 6} Haloalkoxy substituted heteroaryl and via C_{1 - 6} Alkylthio substituted heteroaryl. More preferred substituted aryl groups are chloro substituted heteroaryl, fluoro substituted heteroaryl, trifluoromethyl substituted heteroaryl, chloro and trifluoromethyl substituted heteroaryl, Trifluoromethoxy substituted heteroaryl and methoxy substituted heteroaryl and methylthio substituted heteroaryl. Preferred substituted heterocyclic groups are halogen-substituted heterocyclic rings, via C_{1 - 6} Alkyl substituted heterocyclic ring, via C_{1 - 6} Haloalkyl substituted heterocycle, via C_{1 - 6} Alkoxy substituted heterocycle, via C_{1 - 6} Haloalkoxy substituted heterocyclic ring and C_{1 - 6} Alkylthio substituted heterocycle. More preferably substituted heterocyclic groups are chlorine-substituted heterocyclic rings, fluorine-substituted heterocyclic rings, trifluoromethyl-substituted heterocyclic rings, trifluoromethoxy-substituted heterocyclic rings, substituted by methoxy groups. A heterocyclic ring and a heterocyclic group substituted with a methylthio group. The salt of the compound represented by the formula (1) may be any type of salt as long as it is agriculturally acceptable. Examples of the salt 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 and potassium salts Salts and the like; alkali 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 an embodiment, X and X₁ Indicates oxygen or sulfur; Y represents oxygen or sulfur; Z represents oxygen or sulfur; l is an integer from 0 to 2; m is an integer from 0 to 3; and n is an integer from 0 to 4. In the compound (1) of the present invention, preferred compounds are those in which R₁ Is the following compounds: hydrogen, halogen, nitro, C_{1 - 6} Alkyl, C_{1 - 6} Haloalkyl, C_{1 - 6} Alkylcarbonyl, cyano C_{1 - 6} An alkyl group, optionally substituted aryl group, and more preferably compound (1) is wherein R₁ It is a compound of hydrogen, chlorine, bromine, methyl, chloromethyl, trifluoromethyl, methoxycarbonyl, ethoxycarbonyl or cyanomethyl. In the compound (1) of the present invention, preferred compounds are those in which R₂ For hydrogen or C_{1 - 6} a compound of an alkyl group, and more preferably a compound (1) is wherein R₂ A compound that is a methyl group. In the compound (1) of the present invention, preferred compounds are those in which R₃ For hydrogen, halogen or C_{1 - 6} a compound of an alkyl group, and more preferably a compound (1) is wherein R₃ A compound that is hydrogen. In the compound (1) of the present invention, preferred compounds are those in which R₄ For hydrogen or C_{1 - 6} a compound of an alkyl group, and more preferably a compound (1) is wherein R₄ A compound that is hydrogen. In the compound (1) of the present invention, preferred compounds are those in which R₅ For hydrogen or C_{1 - 6} a compound of an alkyl group, and more preferably a compound (1) is wherein R₅ A compound that is hydrogen. In the compound (1) of the present invention, preferred compounds are those in which R₆ For hydrogen, halogen, C_{1 - 6} Alkyl or C_{1 - 6} a compound of an alkoxy group, and more preferably a compound (1) wherein R₆ A compound of hydrogen, chlorine, methyl or methoxy. In the compound (1) of the present invention, preferred compounds are those in which R₇ For hydrogen, C_{1 - 6} Alkyl or C_{1 - 6} a compound of an alkylcarbonyl group, and more preferably a compound (1) wherein R₇ It is a compound of the following: hydrogen, methyl, ethyl, isopropyl, ethyl fluorenyl, propyl fluorenyl or isobutyl fluorenyl. In the compound (1) of the present invention, preferred compounds are those in which R₈ For C_{1 - 6} a compound of an alkyl group, and more preferably a compound (1) is wherein R₈ A compound that is a methyl group. In the compound (1) of the present invention, preferred compounds are those wherein X is oxygen or sulfur, and more preferably compound (1) is a compound wherein X is oxygen. In the compound (1) of the present invention, a preferred compound is wherein X₁ a compound which is oxygen or sulfur, and more preferably compound (1) is X₁ A compound that is oxygen. In the compound (1) of the present invention, preferred compounds are compounds wherein Y oxygen or sulfur, and more preferably compound (1) is a compound wherein Y is oxygen. In the compound (1) of the present invention, preferred compounds are those wherein Z is oxygen or sulfur, and more preferably compound (1) is a compound wherein Z is sulfur. Among these, a more preferred compound of the present invention is the following compound or a salt thereof, wherein R₁ For hydrogen, halogen, nitro, C_{1 - 6} Alkyl, C_{1 - 6} Haloalkyl, C_{1 - 6} Alkylcarbonyl or cyano C_{1 - 6} Alkyl; R₂ For hydrogen or C_{1 - 6} Alkyl; R₃ For hydrogen, halogen or C_{1 - 6} Alkyl; R₄ For hydrogen or C_{1 - 6} Alkyl; R₅ For hydrogen or C_{1 - 6} Alkyl; R₆ For hydrogen, halogen, C_{1 - 6} Alkyl or C_{1 - 6} Alkoxy; R₇ For hydrogen, C_{1 - 6} Alkyl or C_{1 - 6} Alkylcarbonyl; R₈ For C_{1 - 6} Alkyl; X and X₁ Independently represents oxygen or sulfur; Y represents oxygen or sulfur; Z represents oxygen or sulfur; l is an integer from 0 to 2; m is an integer from 0 to 3; and n is an integer from 0 to 4. A more particularly preferred compound of the invention is a compound or a salt thereof, wherein R₁ For hydrogen, halogen, C_{1 - 6} Alkyl or C_{1 - 6} Haloalkyl; R₂ Is hydrogen or methyl; R₃ For hydrogen; R₄ For hydrogen; R₅ For hydrogen; R₆ Is hydrogen, chlorine, methyl or methoxy; R₇ Is hydrogen, methyl, ethyl, isopropyl, acetyl, propyl or isobutyl); R₈ Methyl; X and X₁ Independently represents oxygen; Y represents oxygen; Z represents oxygen; l is an integer from 0 to 2; m is an integer from 0 to 3; and n is an integer from 0 to 4. The present invention also provides a process for producing a carbamate represented by the formula (1) or a salt thereof.Where R₁ , R₂ , R₃ , R₄ , R₅ , R₆ , R₇ , R₈ , X, X₁ , Y, Z, l, m and n are as defined above. The urethane compound represented by the formula (1) can be easily produced according to the following Reaction Schemes 1 to 4, but is not limited thereto. The urethane compound represented by the formula (1D) can be obtained by subjecting a 2-substituted five-membered heterocyclic compound (2a) to a boron compound (3) as described in the reaction scheme 1, a base and Prepared by the reaction in the presence of a solvent: Reaction Scheme 1Where R₁ , R₂ , R₃ , R₄ , R₅ , R₆ , R₈ , X, X₁ , Y, Z, l, m and n are as defined above. A represents a halogen, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group. R₉ Represents hydrogen, C_{1 - 6} Alkyl (substituent can form two adjacent R₉ -CH₂ CH₂ -, -C(CH₃ )₂ -C(CH₃ )₂ -or-CH₂ -CH₂ -CH₂ -). The foregoing reaction can be carried out in the presence of a transition metal catalyst. As the transition metal catalyst, a generally known transition metal catalyst can be widely used, and examples of the transition metal catalyst include a palladium compound such as palladium (II) acetate, ruthenium (triphenylphosphine) palladium (0), and dichloride (three) Phenylphosphine) palladium (II), tris(diphenylmethyleneacetone) dipalladium and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and methylene chloride And its analog, preferably ruthenium (triphenylphosphine) palladium (0). The amount of the palladium catalyst to be used is usually 0.01 to 1.0 mol, preferably 0.05 to 0.1 mol per 1 mol of the compound (3). The amount of the compound (2a) to be used is usually 0.5 to 5 mol, preferably 1.0 to 2.0 mol per 1 mol of the compound (3). The foregoing reaction can be carried out in the absence or presence of a base. In the above, the reaction is preferably carried out in the presence of a base. As the base, generally known bases can be widely used, and examples of the base include: alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate and the like; alkali metal hydroxides , such as sodium hydroxide, potassium hydroxide and the like; inorganic bases such as alkali metal hydrides such as sodium hydride and potassium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, butanol Potassium and its analogues; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylamine pyridine, piperidine and The analogues and analogs thereof are preferably sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate and sodium hydride. Any of these bases or a combination of two or more types thereof is used. The amount of the base to be used is usually 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol per 1 mol of the compound (3). The foregoing reaction is carried out in a suitable solvent or in the absence of any solvent. When the foregoing reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive with respect to the aforementioned reaction. 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 An analog thereof; 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-dioxane, dimethoxyethane and the like; ester solvents such as methyl acetate, ethyl acetate and the like; acetonitrile; a solvent based on decylamine such as N,N-dimethyl Indoleamine (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and a solvent based on hydrazine, such as dimethyl hydrazine, cyclobutyl fluorene and Analog; H₂ O; acetic acid, preferably dimethoxyethane and ethanol-H₂ O and toluene-H₂ O mixed solvent. Any of these solvents may be used alone, or two or more combinations of the two types may be used as necessary. The amount of the solvent to be used is usually 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of the compound (3). The reaction temperature of the foregoing reaction is not particularly limited, and is usually in the range between -10 ° C and the boiling point of the solvent used, and is preferably from 0 to 120 ° C. The reaction time varies depending on, for example, the reaction temperature, and the reaction usually ends in about 0.5 to 24 hours. The urethane compound represented by the formula (1E) can be obtained by reacting a 5-substituted five-membered heterocyclic compound (2b) with a boron compound (3) as described in Reaction Scheme 2, a base and Prepared by the reaction in the presence of a solvent: Reaction Scheme 2Where R₁ , R₂ , R₃ , R₄ , R₅ , R₆ , R₈ , X, X₁ , Y, Z, l, m and n are as defined above. A represents a halogen, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group. R₉ Represents hydrogen, C_{1 - 6} Alkyl (substituent can form two adjacent R₉ -CH₂ CH₂ -, -C(CH₃ )₂ -C(CH₃ )₂ -or-CH₂ -CH₂ -CH₂ -). The foregoing reaction can be carried out in the presence of a transition metal catalyst. As the transition metal catalyst, a generally known transition metal catalyst can be widely used, and examples of the transition metal catalyst include a palladium compound such as palladium (II) acetate, ruthenium (triphenylphosphine) palladium (0), and dichloride (three) Phenylphosphine) palladium (II), tris(diphenylmethyleneacetone) dipalladium and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and methylene chloride And its analog, preferably ruthenium (triphenylphosphine) palladium (0). The amount of the palladium catalyst to be used is usually 0.01 to 1.0 mol, preferably 0.05 to 0.1 mol per 1 mol of the compound (3). The amount of the compound (2b) to be used is usually 0.5 to 5 mol, preferably 1.0 to 2.0 mol per 1 mol of the compound (3). The foregoing reaction can be carried out in the absence or presence of a base. In the above, the reaction is preferably carried out in the presence of a base. As the base, generally known bases can be widely used, and examples of the base include: alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate and the like; alkali metal hydroxides , such as sodium hydroxide, potassium hydroxide and the like; inorganic bases such as alkali metal hydrides such as sodium hydride and potassium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, butanol Potassium and its analogues; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylamine pyridine, piperidine and The analogues and analogs thereof are preferably sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate and sodium hydride. Any of these bases or a combination of two or more types thereof is used. The amount of the base to be used is usually 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol, per 1 mol of the compound (3). The foregoing reaction is carried out in a suitable solvent or in the absence of any solvent. When the foregoing reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive with respect to the aforementioned reaction. 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 An analog thereof; 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-dioxane, dimethoxyethane and the like; ester solvents such as methyl acetate, ethyl acetate and the like; acetonitrile; a solvent based on decylamine such as N,N-dimethyl Indoleamine (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and a solvent based on hydrazine, such as dimethyl hydrazine, cyclobutyl fluorene and Analog; H₂ O; acetic acid, preferably dimethoxyethane and ethanol-H₂ O and toluene-H₂ O mixed solvent. Any of these solvents may be used alone, or two or more combinations of the two types may be used as necessary. The amount of the solvent to be used is usually 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of the compound (3). The reaction temperature of the foregoing reaction is not particularly limited, and is usually in the range between -10 ° C and the boiling point of the solvent used, and is preferably from 0 to 120 ° C. The reaction time varies depending on, for example, the reaction temperature, and the reaction usually ends in about 0.5 to 24 hours. The urethane compound represented by the formula (1F) can be obtained by reacting a 4-substituted five-membered heterocyclic compound (2c) with a boron compound (3) as described in Reaction Scheme 3, a base and Prepared by reacting in the presence of a solvent: Reaction Scheme 3Where R₁ , R₂ , R₃ , R₄ , R₅ , R₆ , R₈ , X, X₁ , Y, Z, l, m and n are as defined above. A represents a halogen, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group. R₉ Represents hydrogen, C_{1 - 6} Alkyl (substituent can form two adjacent R₉ -CH₂ CH₂ -, -C(CH₃ )₂ -C(CH₃ )₂ -or-CH₂ -CH₂ -CH₂ -). The foregoing reaction can be carried out in the presence of a transition metal catalyst. As the transition metal catalyst, a generally known transition metal catalyst can be widely used, and examples of the transition metal catalyst include a palladium compound such as palladium (II) acetate, ruthenium (triphenylphosphine) palladium (0), and dichloride (three) Phenylphosphine) palladium (II), tris(diphenylmethyleneacetone) dipalladium and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and methylene chloride And its analog, preferably ruthenium (triphenylphosphine) palladium (0). The amount of the palladium catalyst to be used is usually 0.01 to 1.0 mol, preferably 0.05 to 0.1 mol per 1 mol of the compound (3). The amount of the compound (2c) to be used is usually 0.5 to 5 mol, preferably 1.0 to 2.0 mol per 1 mol of the compound (3). The foregoing reaction can be carried out in the absence or presence of a base. In the above, the reaction is preferably carried out in the presence of a base. As the base, generally known bases can be widely used, and examples of the base include: alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate and the like; alkali metal hydroxides , such as sodium hydroxide, potassium hydroxide and the like; inorganic bases such as alkali metal hydrides such as sodium hydride and potassium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, butanol Potassium and its analogues; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylamine pyridine, piperidine and The analogues and analogs thereof are preferably sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate and sodium hydride. Any of these bases or a combination of two or more types thereof is used. The amount of the base to be used is usually 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol, per 1 mol of the compound (3). The foregoing reaction is carried out in a suitable solvent or in the absence of any solvent. When the foregoing reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive with respect to the aforementioned reaction. 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 An analog thereof; 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-dioxane, dimethoxyethane and the like; ester solvents such as methyl acetate, ethyl acetate and the like; acetonitrile; a solvent based on decylamine such as N,N-dimethyl Indoleamine (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and a solvent based on hydrazine, such as dimethyl hydrazine, cyclobutyl fluorene and Analog; H₂ O; acetic acid, preferably dimethoxyethane and ethanol-H₂ O and toluene-H₂ O mixed solvent. Any of these solvents may be used alone, or two or more combinations of the two types may be used as necessary. The amount of the solvent to be used is usually 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of the compound (3). The reaction temperature of the foregoing reaction is not particularly limited, and is usually in the range between -10 ° C and the boiling point of the solvent used, and is preferably from 0 to 120 ° C. The reaction time varies depending on, for example, the reaction temperature, and the reaction usually ends in about 0.5 to 24 hours. The compound (3) used in this step can be produced according to a known method (for example, the method is described in WO2016/114165, WO2016/114164, WO2016/114162 and WO2016/114161). The urethane compound represented by the formula (1) can be produced by reacting the reagent (4) with the compound (1G) in the presence of a catalyst, a base and a solvent as mentioned in Reaction Scheme 4: Reaction Scheme 4Where R₁ , R₂ , R₃ , R₄ , R₅ , R₆ , R₇ , R₈ , X, X₁ , Y, Z, l, m, and n are as defined above, and G represents a leaving group. The ratio between the compound (1G) and the reagent (4) used in the reaction is not particularly limited, and may be appropriately selected from a wide range. The amount of the reagent (4) to be used is usually 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol per 1 mol of the compound (1 G). The foregoing reaction can be carried out in the absence or presence of a base. In the above, the reaction is preferably carried out in the presence of a base. As the base, generally known bases can be widely used, and examples of the base include: alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate and the like; alkali metal hydroxides , such as sodium hydroxide, potassium hydroxide and the like; inorganic bases such as alkali metal hydrides such as sodium hydride and potassium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, butanol Potassium and its analogues; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylamine pyridine, piperidine and The analogs thereof and the like are preferably an alkali metal carbonate and an alkali metal hydride, more preferably sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate or sodium hydride. Any one of these bases or a combination of two or more of these types is used. The amount of the base to be used is usually 1.0 to 5.0 mol, preferably 1.0 to 3.0 mol per 1 mol of the compound (1 G). The foregoing reaction can be carried out by further adding a radical initiator. Examples of the radical initiator include, but are not particularly limited to, a sulfite adduct such as sulfurous acid, sulfite, Rongalite (a compound name, sodium formaldehyde sulfoxylate), and the like. A base and a radical initiator can be used in combination. When a radical initiator is used, the amount of the radical initiator to be used is usually from 0.1 to 10.0 mol, preferably from 0.1 to 5.0 mol, per 1 mol of the compound (1 G). The foregoing reaction is carried out in a suitable solvent. Examples of the 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, THF, 1,4-dioxane And analogs thereof; ester-based solvents such as methyl acetate, ethyl acetate and the like; guanamine-based solvents such as acetonitrile; DMF, N,N-dimethylacetamide, N-methyl- 2-pyrrolidone and its analogues; dimethyl sulfoxide and its analogs, solvents based on hydrazine; polar solvents such as alcohol-based solvents such as cyclobutyl hydrazine, methanol, ethanol, isopropanol and the like ; water; and its analogues. Any of these solvents may be used alone, or two or more combinations of the two types may be used as necessary. The amount of the solvent to be used is usually 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of the compound (1 G). The reaction temperature varies depending on the starting compound, the reagent, the solvent and the like, but it is usually -40 ° C to reflux temperature in the reaction system, preferably 0 to 100 ° C. The reaction time varies depending on the compound, the reagent, the solvent and the reaction temperature, and the like, but is usually from 5 minutes to 48 hours, preferably from 10 minutes to 24 hours. The compound represented by the formula (1) obtained by the present process shown in Schemes 1 to 4 is easily separated from the reaction mixture, and can be separated by a typical separation method and purification method (for example, filtration, solvent extraction, distillation, Recrystallization, column chromatography, etc.) to purify. Although the form of the compound used in the present invention may be the compound of the present invention itself, 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 the like, and is necessary. Adding an adhesive, a dispersing agent and a stabilizer to prepare a wettable powder, a water-dispersible granule, a flowable substance, a granule, a dry flowable substance, an emulsifiable concentrate, an aqueous solution, an oil solution, an aerosol, an aerosol, a micro Capsules and others, in such formulations, typically comprise from 0.1 to 99% by weight, preferably from 0.2 to 90% by weight of the compound of the invention. Examples of solid carriers include clays in the form of fine powders or particulates (eg, kaolin, diatomaceous earth, synthetic hydrated ceria, Fubasami clay, bentonite, and acid clay), talc, or other inorganic minerals (eg, sericite, Quartz powder, sulfur powder, activated carbon, calcium carbonate and hydrated cerium oxide), and examples of the liquid carrier include water, alcohols (for example, methanol and ethanol), ketones (for example, 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 and butyl acetate) ), nitriles (eg, acetonitrile and isobutyronitrile), ethers (eg, dioxane and diisopropyl ether), guanamines (eg, N,N-dimethylformamide (DMF) and Dimethylacetamide), halogenated hydrocarbons (for example, 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 sugars. Alcohol derivatives. Examples of other adjuvants for use in the formulation include adhesives, dispersants, and stabilizers, specifically casein, gelatin, polysaccharides (eg, 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 acid phosphate), BHT (2,6-di- Tributyl-4-methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid or Its fatty acid esters and others. The method of administering a compound of the present invention is not particularly limited as long as the form of administration is a form by which the compound of the present invention can be administered, and includes, for example, administration to a plant, such as leaf application; administration to a field for cultivating a plant, Such as immersion treatment; and application to contamination, such as seed sterilization. The dosage administered varies depending on weather conditions, dosage form, timing of administration, method of administration, area to be administered, target disease, target crop, etc., but usually at every 1,000 m² The area to be applied is in the range of 1 to 500 g, and preferably 2 to 200 g. Emulsifying concentrates, wettable powders or suspension concentrates and the like are usually applied by dilution with water. In this case, the concentration of the compound of the present invention is usually in the range of 0.0005 to 2% by weight, and preferably 0.005 to 1% by weight, after dilution. Dust formulations or granule formulations and the like are usually applied by themselves 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 to 100 g, and preferably 0.01 to 50 g per 1 kg of the seed. Herein, examples of places where pests survive include rice fields, fields, tea gardens, orchards, non-farm fields, houses, seedling trays, seedling boxes, seedling soils, and nursery beds. Further, in another embodiment, for example, the compound of the present invention can be administered to the interior (inside of the body) or the outside (body surface) of the vertebrate mentioned below to parasitize the vertebrate in a systemic or non-systemic manner. Live or parasite. Examples of methods of internal medicine include oral administration, anal administration, colonization, administration by subcutaneous, intramuscular or intravenous injection. Examples of external pharmaceutical methods include transdermal administration. Furthermore, the compounds of the invention may be ingested by livestock animals to eliminate the appearance of sanitary insects in animal waste. When the compound of the present invention is administered to an animal such as livestock animals and pets on which the pest is parased, the dose varies depending on the administration method and the like, but it is generally desirable 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 thereof is generally in the range of 0.1 mg to 2,000 mg per 1 kg of animal body weight, and preferably in the range of 0.5 mg to 1,000 mg. The compounds of the present invention are useful as agents for controlling plant diseases in farmland such as fields, rice fields, lawns, orchards. The compounds of the present invention can control diseases occurring in farmland or in other fields used to grow the following "plants". Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, beets, rapeseed, sunflower, sugar cane, tobacco and others; vegetables: solanaceous vegetables (solanaceous vegetable) For example, eggplant, tomato, sweet pepper, pepper and potato), cucurbitaceous vegetable (for example, courgette, pumpkin, zucchini, watermelon and melon), cruciferous vegetable (for example, Japan) Japanese radish, white phthalocyanine, horseradish, broccoli, Chinese cabbage, kale, leaf mustard, broccoli, cauliflower, asteraceous vegetable (asteraceous vegetable) For example, burdock, crown daisy, artichoke and lettuce, liliaceous vegetable (eg, green onion, onion, garlic, and asparagus), ammiaceous vegetable (ammiaceous vegetable) For example, carrots, parsley, celery and parsnips, chenopodiaceous vegetables (for example, spinach and red wine (Swiss chard)), and labiatae ( Lamiaceous vegetable) (for example, Perilla frutescens, mint and basil, strawberry, sweet potato, Dioscorea japonica, colocasia and others; flower: ornamental plant leaf plant: fruit: pear fruit (pomaceous) fruits (eg, apples, pears, Japanese pears, Chinese quince and citrus), stone fruits (eg, peach, plum, nectarine, plum (Prunus mume), cherry fruit, apricot, and dried plum (prune) ), citrus fruits (eg, Citrus unshiu, orange, lemon, lime, and grapefruit), nuts (eg, chestnuts, walnuts, hazelnuts, almonds, pistachios, Cashew nut and macadamia nut, berry fruits (eg, bilberry, cranberry, blackberry and raspberry), grapes, kaki persimmon, olive, Japanese plum, banana, coffee, Date palm, coconut and others; trees other than fruits and trees: tea mulberry, flowering plants, roadside trees (eg, ash, birch, dogwood, eucalyptus) , Ginkgo biloba, snow Green (lilac), maple (maple), Quercus, poplar, Judas tree, Liquidambar formosana, plane tree, zelkova, Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, and Taxus cuspidata; and others. The "plant" mentioned above includes genetically modified crops. Pests for which the compounds of the invention have control effects include plant pathogens such as filamentous fungus, as well as harmful arthropods such as harmful insects and harmful aphids, and nemathelminths such as nematodes, and in particular This includes but is not limited to the following examples. Rice diseases: blast (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizobacter serrata) (Rhizoctonia solani)), rice bakanae disease (Gibberella fujikuroi) and downy mildew (Sclerophthora macrospora); wheat disease: powdery mildew (powdery mildew) (Erysiphe graminis), fusarium blight (Fusarium graminearum, F. avenaceum, F. culmorum, snow mold) Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), snow mould (C. oxysporum) Micronectriella nivale)), typhulasnow blight (Typhula sp.), loose smut (Ustilago tritici), smut ( Stinking smut) (Tilletia caries, wheat dwarf smut (T. contro) Versa)), wheat sheath blight (eyespot) (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (wheat leaf spot) Diseased fungi (Stagonospora nodorum), brown spot (Pyrenophora tritici-repentis), rhizoctonia seeding blight (Rhizobacter serrata) and all diseases (Geumannomyces graminis); Barley disease: powdery mildew (grass powder), sickle blight (Fusarium graminearum, Fusarium oxysporum, Fusarium oxysporum, snow mold blight), rust ( Stripe rust, rod rust, barley rust (P. hordei), smut (Ustilago nuda), browning (scald) (Rhynchosporium secalis), net Net blotch (Pyrenophora teres), spot blotch (Cochliobolus sativus), leaf stripe (Pyrenophora) Graminea)), Ramularia disease (Ramularia c) Ollo-cygni)) and Rhizoctonia seed plague (Rh. rhizogenes); corn disease: rust (Puccinia sorghi), southern rust (Puccinia polysora), Northern leaf blight (Setosphaeria turcica), southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (gray leaf) Spot) (Cercospora zeae-maydis), wheat sheath blight (Kabatiella zeae) and phaeosphaeria leaf spot (Phaeosphaeria maydis) Cotton disease: anthracnose (anthrax cotton), gray mold (Ramularia areola), alternaria leaf spot (Alternaria macrospora, cotton bollworm (A. gossypii) Coffee disease: rust (Hemileia vastatrix); rapeseed disease: sclerotinia rot (Sclerotinia sclerotiorum), black spot ( Alternaria alternata (Alternaria brassicae)) and black leg (Phoma lingam); citrus disease: melanose (Diaporthe citri), scab ( Scab) (Elsinoe fawcettii) and fruit rot (Penicillium digitatum, P. italicum); apple disease: blight blight (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), broad bean leaf spot (alternaria leaf spot) (Alternaria alternata apple pathotype), scab (Venturia inaequalis) and bitter rot (Colletotrichum acutatum); pear disease: Scab disease (Venturia nashicola, V. pirina), plant black spot (Alternaria alternata Japanese pear pathotype) and rust ( Pear rust (Gymnosporangium haraeanum); peach disease : brown rot (Monilinia fructicola), scab (Cladosporium carpophilum) and Phalaopsis rot (Phomopsis sp.) )); grape disease: anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), powdery mildew (Uncinula necator), Rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii) and downy mildew (Plasmopara viticola); Japan Persimmon diseases: anthracnose (Gloeosporium kaki) and leaf spot (Cercospora kaki, Mycosphaerella nawae); disease of the gourd family: anthracnose (melon anthrax) Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Didymella bryoniae), target spot (multiple rods) Corynespora cassiicola), Fusarium wilt disease Wilt) (Fusarium oxysporum, downy mildew (Pseudoperonospora cubensis), phytophthora rot (Phytophthora sp.) and tripping Damping-off (Pythium sp.); tomato disease: early blight (Alternaria solani), leaf mold (Cladosporium) Fulvum), leaf mold (Pseudocercospora fuligena) and late blight (Phytophthora infestan); eggplant disease: brown spot (Phomopsis vexans) And powdery mildew (Erysiphe cichoracearum); Cruciferous vegetable diseases: Alternaria leaf spot (Alternaria japonica), white spot (short tail) Cercosporella brassicae), clubroot (Plasmodiophora parasitica), downy mildew (Peronospora parasitica); green onion disease: rust (Puccinia allii) Soybean disease: purple spot (Ceramicus sclerotium), round Sphaceloma scad (Esinoe glycines), pod and stem blight (Diaporthe phaseolorum var. sojae), rust (soybean rust), target spot disease (multi-spore Mildew, anthracnose (Colletotrichum glycines/C. truncatum), Rhizoctonia aerial blight (Rhizobacter pylori), Septoria brown spot (Soybean brown spot) Helicobacter pylori and frog eye leaf spot; Bean disease: anthracnose (Anthracnose edulis); Peanut disease: Early leaf spot (Cercospora personata), Late leaf spot (Cercospora arachidicola) and southern blight (Sclerotium rolfsii); pea disease: powdery mildew (white powder); potato disease: early blight (potato summer) Alternaria solani, late blight (potato rot), and verticillium wilt (verticillium albo-atrum, V. dahliae, blackened) Verticillium (V. nigrescens); Strawberry disease: powdery mildew (Strawberry powdery mildew); Tea tree disease: net blister blight (Exobasidium reticulatum), white scab (Elsinoe leucospila) ), gray blight (Pestalotiopsis sp.) and anthracnose (Colletotrichum theae-sinensis); tobacco disease: brown spot (Alternaria alternata), white powder Disease (Bacillus white fungus), anthracnose (tobacco anthracnose), downy mildew (Peronospora tabacina) and black stalk (Phytophthora nicotianae); beet disease: tail Phytophthora leaf spot (C. cerevisiae), leaf blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris) (R. solani) and genus root rot (beet) Aphanomyces cochlioides; Rose disease: black spot disease (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa); chrysanthemum disease: leaf blight (wild chrysanthemum Septoria chrysanthemi-indici) and Rust (Puccinia horiana); Onion disease: Botrytis blight (B. ssoidea, B. squamosa) , gray mold neck rot (Botrytis allii) and small bacterial rot (Botrytis squamosa); various crop diseases: gray mold (G. cinerea) and Sclerotinia sclerotiorum Sclerotinia rot (Sclerotium); Japanese radish disease: Alternaria brassica (Alternaria brassicicola); turf grass disease: dollar spot (Dollar spot) Sclerotinia homoeocarpa, brown spots and large spots (Rhizobacter serrata); and banana diseases: Sigatoka disease (G. sinensis, G. sphaeroides). Hemiptera: Delphacidae (eg, Laodelphax striatellus, brown planthopper or white-backed planthopper); Deltocephalinae (eg pseudo-black-tailed spider mites or two-point black) Eucalyptus (Aphis gossypii); Aphididae (eg, cotton aphid, peach aphid, rapeseed meal, Macrosiphum euphorbiae, potato scorpion, scorpion scorpion, Toxoptera citricidus); Pentatomidae) (eg, southern rice genus, Riptortus clavatus, Leptocorisa chinensis, Eysarcoris parvus, Halyomorpha mista or Lygus lineolaris )); Aleyrodidae (such as Trialeurodes vaporariorum or Bemisia argentifolii); Coccoidea (such as Aonidiella aurantii, pear) Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens or Icerya purchasi; Tingidae, Psyllidae Bed bugs (temperate bed bugs (Cimex) Lectularius)) and others. Lepidoptera: Coleoptera (eg, Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella) , Asian corn borer (Ostrinia furnacalis), Hellula undalis (Pediasia teterrellus), Noctuidae (such as Spodoptera litura, Spodoptera exigua), sticky night Moth (Pseudaletia separata), Mamestra brassicae, Agrotis ipsilon, Plusia nigrisigna, Trichoplusia spp., Heliothis Spp.) or Helicoverpa spp.; Pieridae (eg, Pieris rapae), Tortricidae (eg, Adoxophyes spp., peach) Heartworm (Grapholita molesta), Cydia pomonella, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes Sp .), Homona magnanima, Archips fuscocupreanus, Cydia pomonella; Graculillariidae (eg Caloptilia theivora, Phyllodon moth) Ringoniella)); Carposinidae (eg Carposina niponensis); Lyonetiidae (eg Lyonetia spp.; Lymantriidae (eg Lymantria) Spp.) or Euproctis spp.; Yponomeutidae (eg Plutella xylostella); Gelechiidae (eg Pectinophora gossypiella or potato tuber moth (Phthorimaea operculella) )); genus Moth (such as Hyphantria cunea); Tineidae (such as Tinea translucens or Tineola bisselliella); and others; Thysanoptera: Thysanoptera (such as Frankliniella occidentalis, Thrips palmi, Scirthothrips dorsalis, Thrips tabaci, Frankliniella intonsa, smoky brown flower (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, Aulacophora femoralis, Phyllotreta striolata, Oulema Oryzae), Echinocnemus squameus, Lissorhoptrus oryzophilus, Anthonomus grandis, Callosobruchus chinensis, Sphenophorus venatus, Japanese Lijin tortoise Popillia japonica), Anomala cuprea, Diabrotica spp., potato beetle (Leptinotarsa decemlineata), Agriotes spp., Yankee (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: Aedalia Rosae), Acromyrmex spp., Solenopsis spp. and others; Nematodes: Aphelenchoides besseyi, Nothotylenchus acris, Soybean Heterodera glycines), Meloidogyne incognita, Pratylenchus, Nacobbus aberrans and others; Blattariae: Blattella germanica, Black-brown Periplaneta fuliginosa), Periplaneta americana, Periplaneta brunnea, Blatta orientalis and others; 蜱螨目:Tetranychidae ( Such as Tetranychus urticae, Panonychus citri or Oligonychus spp.; Eriophyidae (eg Aculops pelekassi); Tarsonemidae (eg Polyphagotarsonemus latus); Tenuipalpidae; Tuckerellidae; Acaridae (eg Tyrophagus putrescentiae) (Pyroglyphidae) (such as Dermatophagoides farinae or Dermatophagoides pteronyssinus); Cheyletidae (such as Cheyletus eruditus, Cheyletus malaccensis or 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 diseases or the livestock industry, and for example can eliminate parasitism in vertebrates (such as humans, cows, sheep, pigs, poultry, dogs, cats and Live or hygienic on the inside and/or outside of the fish) to maintain public health. Examples of pests include the genus Ixodes spp. (e.g., Ixodes scapularis), Boophilus spp. (e.g., Boophilus microplus), and the genus Amblyomma spp. ), Hyalomama spp., Rhipicephalus spp. (such as Rhipicephalus sanguineus), Haemaphysalis spp. (such as Haemaphysalis longicornis) )), dermacentor spp., Ornithodoros spp. (eg Ornithodoros moubata), Dermanyssus gallinae, Ornithonyssus sylviarum, 疥螨Genus (Sarcoptes spp.) (eg, Sarcoptes scabiei), Psoroptes spp., Chorioptes spp., Demodex spp., subgenus Eutrombicula spp.), Ades spp. (eg Aedes albopictus), Anopheles spp., Culex spp., Culicoides spp. ), Musca spp., Hypoderma spp., Gasterophilus spp., Haematobia spp., Tabanus spp., Simulium spp., Triatoma spp., Phthiraptera (eg Damalina spp.), Lidognathus spp. ), Haematopinus spp., Ctenocephalides spp. (eg Ctenocephalides felis), Xenopsylla spp., monomorium pharaonis and nematodes (nematodes/hairworm) (eg, Nippostrongylus brasiliensis, Trichostrongylus axei, Trichostrongylus colubriformis, Trichinella spp. (eg Trichinella) Spiralis)), Haemonchus contortus, Nematodirus spp. (eg Nematodirus battus), Ostertagia circumcincta, Cooper nematode ( Cooperia spp.), Hymenolepis nana and others. The urethane (1) of the present invention is used as an active ingredient of, for example, a fungicide. The urethane (1) of the present invention can be used in a desired form such as an oil, an emulsion, a wettable powder, a flowable preparation, a granule, a powder, an aerosol, a fumigant or the like. In this case, the content of the urethane (1) of the present invention is not limited and may be suitably selected from a wide range according to various conditions such as a form of preparation, a disease type to be treated, a plant species, and a disease. Severity, application site, application time, application method, combined use of chemicals (insecticides, nematicides, acaricides, fungicides, herbicides, plant growth control agents, synergists, Soil conditioners, etc.), the amount and type of fertilizer, etc. The content is usually from about 0.01 to about 95% by weight based on the total amount of the fungicidal preparation. A fungicidal preparation containing the urethane (1) of the present invention as an active ingredient can be produced according to a known method. For example, the urethane (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 for preparation may be added as appropriate. Suitable carriers can be any of the carriers known in the art. Examples of suitable solid carriers are fine particles or granules of clay (kaolin clay, diatomaceous earth, synthetic hydrated ceria, bentonite, fubasami clay, acid clay and the like), talc, ceramics, other inorganic minerals. Stone, quartz, sulfur, activated carbon, calcium carbonate, hydrated cerium oxide, etc.) and the like. Suitable liquid carriers are, for example, water, alcohols (such as methanol, ethanol, etc.), ketones (such as acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (such as benzene, toluene, xylene, ethylbenzene, Methylnaphthalene, 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 (such as diisopropyl ether, dioxane, etc.), guanamines (such as N,N-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (such as dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethylformamide, soybean oil, cottonseed oil, vegetable oil, and the like. Examples of suitable gaseous carriers (propellants) are butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide, and the like. Examples of suitable 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 suitable adjuvants for the preparation are fixatives such as casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose compounds, alginic acid, etc.), lignin compounds, bentonite, sugars, synthetic water-soluble polymerizations. (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.) and its analogues; stabilizers such as PAP (isopropyl isopropyl phosphate), BBH (2,6-di-t-butyl-4-methyl) Phenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids, esters 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 an insecticide, a nematicide, an acaricide, a fungicide, a herbicide, a plant growth controlling agent, a synergist, a soil conditioner, 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 suitably selected from a wide range according to various conditions such as the concentration of the active ingredient, the form of the preparation. , the type of disease to be treated, the type of plant, the severity of the disease or sputum, the time of administration, the method of application, the chemicals used in combination (insecticides, nematicides, miticides, fungicides, herbicides) , plant growth control agents, synergists, soil conditioners, etc.), the amount and type of fertilizer, and so on. This amount is usually every 100 m² The area is from about 0.001 to about 100 g. When a water-diluted emulsion, a wettable powder, a flowable preparation or the like is used, the concentration of the fungicidal or acaricidal preparation is from about 0.1 to about 1000 ppm, preferably from about 1 to 500 ppm. The particles, microparticles or the like are applied as they are without dilution. The compounds of the invention are characterized by excellent fungicidal activity and a wide range of activities. The compounds are useful for controlling plant diseases attributable to pathogenic fungi and resistant pathogenic fungi. Examples of such pathogenic fungi include those which cause or are tolerant to the treatment of the following diseases: rice plant rice blast, rice plant sheath blight, gray mold on tomato, apple powdery mildew, apple genus Persimmon powdery mildew, grape powdery mildew, barley powdery mildew, wheat powdery mildew, squash powdery mildew, squash gray mold, tomato late blight, potato blight and its analogues. EXAMPLES The present invention will describe in more detail the preparation examples, formulation examples, and test examples. The invention is described in more detail with respect to the following reference examples, manufacturing examples, formulation examples, and test examples. However, the invention is not limited to these examples. Further, changes may be made without departing from the scope of the invention. Preparation Example 1 Preparation of methyl 2-((2-methyl-4-(4-(trifluoromethyl)thiazol-2-yl)phenoxy)methyl)phenyl)carbamate (Compound 1A- 1) (1) 1-(2-Nitrobenzyloxy)-4-bromo-2-toluene to 4-bromo-2-methylphenol (0.93 g, 5.0 mmol) and (2-nitrogen) under nitrogen atmosphere Triphenylphosphine (1.9 g, 7.5 mmol) was added to a cooled solution of phenyl)methanol (1.0 g, 6.5 mmol) in anhydrous THF (10 ml), followed by the slow addition of diethyl azodicarboxylate (0.78 g, 7.5 Mm). The resulting mixture was then stirred at room temperature for 12 h. The reaction mixture was then poured into cold distilled water and extracted with ethyl acetate (3×EtOAc). The combined organic layers were washed with EtOAc (EtOAc)EtOAc. The residue was purified by column chromatography (EtOAc:EtOAc:¹ H NMR (CDCl₃ ): δ 8.18 (d, J = 8.0 Hz, 1H), 7.88 (d, J = 7.6 Hz, 1H), 7.70 (t, J = 8.4 Hz, 1H), 7.51 (t, J = 7.6 Hz, 1H) , 7.31-7.30 (m, 1H), 7.27-7.24 (m, 1H), 6.74 (d, J = 8.4 Hz, 1H), 5.46 (s, 2H), 2.30 (s, 3H). (2) 2-((4-Bromo-2-methylphenoxy)methyl)aniline added cuprous chloride (0.74 g, 7.5 mmol) to 1-(2-nitrobenzyloxy)- A solution of 4-bromo-2-toluene (1.2 g, 3.7 mmol) in MeOH (10 mL). Sodium borohydride (0.69 g, 18.7 mmol) was then added portionwise to this mixture. The resulting mixture was then stirred at room temperature for 2 h. The reaction mixture was then quenched with EtOAc (EtOAc)EtOAc The organic layer was washed with EtOAc (EtOAc m. It was then used in the next step without further purification.¹ H NMR (DMSO-d ₆ ): δ 7.33-7.30 (m, 2H), 7.18-7.17 (m, 1H), 7.04-7.00 (m, 2H), 6.68-6.66 (m, 1H), 6.55 (t, J = 7.2 Hz, 1H) , 5.06 (bs, 2H), 4.95 (s, 2H), 2.16 (s, 3H). (3) Methyl 2-((4-bromo-2-methylphenoxy)methyl)phenylcarbamate to 2-((4-bromo-2-methylphenoxy)methyl)aniline (0.90 g, 3.1 mmol) pyridine (0.74 g, 9.3 mmol). Methyl chloroformate (0.43 g, 4.6 mmol) was then slowly added to this mixture. The resulting mixture was then stirred at room temperature for 12 h. The reaction mixture was then poured into cold water and extracted with dichloromethane (3× 80 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated The title compound (0.75 g, yield: 69%).¹ H NMR (DMSO-d ₆ ): δ 9.01 (bs, 1H), 7.49-7.45 (m, 2H), 7.36-7.30 (m, 3H), 7.18 (t, J = 7.6 Hz, 1H), 6.93 (d, J = 8.4 Hz, 1H ), 5.12 (s, 2H), 3.65 (s, 3H), 2.17 (s, 3H). (4) 2-((2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy) A Methyl phenylaminocarbamate to methyl 2-((4-bromo-2-methylphenoxy)methyl)phenylcarbamate (0.75 g, 2.1 mmol) and potassium acetate under nitrogen atmosphere (0.42 g, 4.3 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and dichloride in a mixture of 1,4-dioxane (5.0 ml) A complex of methane (0.09 g, 0.10 mmol) followed by bis(pinadol) diboron (0.81 g, 3.2 mmol). The resulting mixture was then refluxed for 3 h. The reaction mixture was then diluted with ethyl acetate. The organic layer was washed with EtOAc EtOAc EtOAc. It was then used in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 8.01 (bs, 1H), 7.66-7.59 (m, 3H), 7.39-7.35 (m, 1H), 7.30-7.29 (m, 1H), 7.10-7.06 (m, 1H), 6.96 (d, J = 8.0 Hz, 1H), 5.11 (s, 2H), 3.74 (s, 3H), 2.25 (s, 3H), 1.33 (s, 12H). (5) Methyl 2-((2-methyl-4-(4-(trifluoromethyl)thiazol-2-yl)phenoxy)methyl)phenyl)carbamate (Compound 1A-1) To 2-bromo-4-(trifluoromethyl)thiazole (0.058 g, 0.25 mmol) and potassium carbonate (0.070 g, 0.5 mmol) in 1,4-dioxane (5 ml) To the mixture was added hydrazine (triphenylphosphine) palladium (0) (0.014 g, 0.01 mmol) followed by 2-((2-methyl-4-(4,4,5,5-tetramethyl-1,3) Methyl 2-dioxaborolan-2-yl)phenoxy)methyl)phenylcarbamate (0.1 g, 0.25 mmol). The resulting mixture was then refluxed for 3 h. The reaction mixture was then diluted with ethyl acetate (50 mL). The organic layer was washed with distilled water, dried over sodium sulfate, filtered and evaporated The title compound (0.060 g, yield: 47%).¹ H NMR (CDCl₃ ): δ 8.00 (bs, 1H), 7.81-7.77 (m, 2H), 7.66 (s, 1H), 7.51 (bs, 1H), 7.39 (t, J = 7.2 Hz, 1H), 7.33 (d, J = 7.6 Hz, 1H), 7.11 (t, J = 7.6 Hz, 1H), 7.00 (d, J = 8.8 Hz, 1H), 5.16 (s, 2H), 3.77 (s, 3H), 2.31 (s, 3H ). Preparation Example 2 Preparation of methyl 2-((4-(4-chlorothiazol-2-yl)-2-methylphenoxy)methyl)phenylcarbamate (1A-2) to 2 under nitrogen atmosphere Add ruthenium (triphenylphosphine) palladium (0) to a mixture of 4-dichlorothiazole (0.06 g, 0.39 mmol) and potassium carbonate (0.11 g, 0.78 mmol) in 1,4-dioxane (5.0 ml) (22 mg, 0.02 mmol) followed by 2-((2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-) Phenyloxy))) Methyl phenylcarbamate (0.15 g, 0.39 mmol). The resulting mixture was then refluxed for 3 h. The reaction mixture was then diluted with ethyl acetate (50 mL). The organic layer was washed with distilled water, dried over sodium sulfate, filtered and evaporated The crude product was purified by EtOAc EtOAc (EtOAc:EtOAc: Methyl phenoxy)methyl)phenylcarbamate (0.050 g, yield: 33%).¹ H NMR (CDCl₃ ): δ 7.99 (bs, 1H), 7.77 (s, 1H), 7.75-7.72 (m, 1H), 7.53 (bs, 1H), 7.41-7.37 (m, 1H), 7.32 (d, J = 7.6 Hz) , 1H), 7.11 (t, J = 7.6 Hz, 1H), 7.01-6.98 (m, 2H), 5.14 (s, 2H), 3.77 (s, 3H), 2.30 (s, 3H). Preparation Example 3 Preparation of methyl 3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenyl)carbamate (Compound 1A- 39) (1) 2-(4-Methoxy-3-methylphenyl)-4-methylthiazole to 2-bromo-4-methylthiazole (1.0 g, 5.6 mmol) in DMF under nitrogen atmosphere :H₂ Sodium carbonate (1.19 g, 0.0112 mol) was added to the solution in O (10:1, 3.0 ml), followed by the addition of 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride. Dichloromethane (0.457 g, 5.6 mmol). 4-methoxy-3-methylphenylAcid (1.38 g, 8.41 mmol) was added to the reaction mixture, which was then stirred at 100 ° C for 12 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude product was purified by EtOAc EtOAc (EtOAc) .¹ H NMR (CDCl₃ ): δ 7.73-7.71 (m, 2H), 6.84 (d, J = 9.2 Hz, 1H), 6.79-6.78 (m, 1H), 3.87 (s, 3H), 2.48 (s, 3H), 2.26 (s , 3H). (2) 2-Methyl-4-(4-methylthiazol-2-yl)phenol 2-(4-methoxy-3-methylphenyl)-4-methylthiazole (0.8 g, 3.6 A solution of mmol in HBr (10 ml) and acetic acid (5.0 ml) was refluxed at 120 ° C for 24 h. After the reaction was completed, the reaction mixture was treated with a saturated sodium hydrogen carbonate solution until the pH became about 10. This was extracted with EtOAc (3×50 mL)EtOAc. ). It was then used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.73 (s, 1H), 7.64-7.62 (m, 1H), 6.80-6.78 (m, 2H), 5.07 (bs, 1H), 2.48 (s, 3H), 2.29 (s, 3H). (3) 2-(Bromomethyl)-1-chloro-3-nitrobenzene to 1-chloro-2-methyl-3-nitrobenzene (1.0 g, 5.8 mmol) in carbon tetrachloride (30) N-bromobutaneimine (1.03 g, 5.8 mmol) was added to the solution in ml), followed by the addition of benzamidine peroxide (0.071 g, 0.29 mmol). The reaction mixture was refluxed at 80 ° C for 6 h. The reaction mixture was then cooled to room temperature and filtered. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude compound was purified by EtOAc EtOAcjjjjjj¹ H NMR (CDCl₃ ): δ 7.87-7.85 (m, 1H), 7.70-7.68 (m, 1H), 7.43 (t, J = 8.0 Hz, 1H), 4.87 (s, 2H). (4) 2-(4-((2-Chloro-6-nitrobenzyloxy)-3-methylphenyl)-4-methylthiazole to 2-methyl-4-(4-methyl) Potassium carbonate (0.7 g, 5.1 mmol) was added to a solution of thiazol-2-yl)phenol (0.7 g, 3.4 mmol) in acetonitrile (10 mL) followed by 2-(bromomethyl)-1-chloro-3 - nitrobenzene (0.85 g, 3.4 mol), and the reaction mixture was refluxed for 3 h at 80 ° C. The reaction mixture was diluted with ethyl acetate (70 mL) and washed with water (3×100 mL) Drying and evaporation to dryness. 4-methylthiazole (0.80 g, yield: 62%).¹ H NMR (CDCl₃ ): δ 7.75-7.72 (m, 3H), 7.70-7.67 (m, 1H), 7.47 (t, J = 8.0 Hz, 1H), 6.93 (d, J = 9.2 Hz, 1H), 6.79-6.78 (m , 1H), 5.49 (s, 2H), 2.48 (s, 3H), 2.17 (s, 3H). (5) 3-Chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)aniline to 2-(4-(2-) at 0 °C Addition of cuprous chloride (0.63 g) to a solution of chloro-6-nitrobenzyloxy)-3-methylphenyl)-4-methylthiazole (0.80 g, 2.1 mmol) in methanol (20 ml) 6.3 mmol) followed by sodium borohydride (0.24 g, 6.4 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was filtered and evaporated with w~~~~~~~~~~~~~~~~~~~ g, crude product). It was used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.75-7.71 (m, 2H), 7.09-7.04 (m, 2H), 6.83-6.79 (m, 2H), 6.61 (d, J = 8.0 Hz, 1H), 5.34 (s, 2H), 4.27 (bs, 2H), 2.48 (s, 3H), 2.16 (s, 3H). (6) Methyl 3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenyl)carbamate (Compound 1A-39) To 3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)aniline (0.60 g, 1.7 mmol) in dichloromethane (10 ml Pyridine (0.20 g, 2.5 mmol) was added to the solution, followed by methyl chloroformate (0.20 g, 2.1 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude compound was purified by column chromatography to afford 3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)benzene as a yellow solid. Methyl carbazate (0.50 g, yield: 71%).¹ H NMR (CDCl₃ ): δ 7.96 (d, J = 8.0 Hz, 1H), 7.90 (bs, 1H), 7.77 (s, 1H), 7.74-7.71 (m, 1H), 7.29 (t, J = 8.4 Hz, 1H), 7.16-7.14 (m, 1H), 7.05 (d, J = 8.8 Hz, 1H), 6.80 (d, J = 1.2 Hz, 1H), 5.40 (s, 2H), 3.77 (s, 3H), 2.49 (s , 3H), 2.30 (s, 3H). Preparation Example 4 Preparation of methyl 3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenyl(methyl)carbamate (compound) 1A-43) Methyl (3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenyl)carbamate at 0 ° C Sodium hydride (6.0 mg, 0.26 mmol) was added to a solution of EtOAc (EtOAc (EtOAc) The reaction mixture was stirred at room temperature for 3 h. EtOAc (EtOAc)EtOAc. Purification by column chromatography gave 3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)benzene as a yellow viscous oil Methyl (meth)carbamate (40 mg, yield: 55%).¹ H NMR (CDCl₃ ): δ 7.75-7.73 (m, 2H), 7.45-7.43 (m, 1H), 7.36 (t, J = 8.0 Hz, 1H), 7.15-7.11 (m, 1H), 6.98 (d, J = 9.2 Hz) , 1H), 6.79 (d, J = 1.2 Hz, 1H), 5.12 (d, J = 10.0 Hz, 1H), 5.03 (d, J = 10.0 Hz, 1H), 3.76-3.22 (m, 6H), 2.49 (s, 3H), 2.20 (s, 3H). Preparation Example 5 Preparation of (3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenyl)carbamic acid methyl ethyl decyl ester ( Compound 1A-46) methyl 3-chloro-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenylcarbamate at 0 ° C (90 mg, 0.22 mmol) of sodium hydride (8 mg, 0.33 mmol). After 10 minutes, ethyl chloroform (22 mg, 0.30 mmol) was added to the reaction mixture and then stirred at room temperature for 3 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude compound was purified by column chromatography to give (3-chloro-2-(4-methyl-4-(4-methylthiazol-2-yl)phenoxy) Methyl ethyl phenyl methacrylate (50 mg, yield: 50%).¹ H NMR (CDCl₃ ): δ 7.75-7.74 (m, 1H), 7.71-7.69 (m, 1H), 7.50 (d, J = 7.6 Hz, 1H), 7.38 (t, J = 8.0 Hz, 1H), 7.06 (d, J = 8.0 Hz, 1H), 6.90 (d, J = 8.4 Hz, 1H), 6.79 (s, 1H), 3.53 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H), 2.20 (s , 3H). Preparation Example 6 Preparation of methyl 2-((2-methyl-4-(thiazol-5-yl)phenoxy)methyl)phenylcarbamate (Compound 1B-1) to 5-bromine under nitrogen atmosphere Thiazole (0.15 g, 0.91 mmol) in 1,4-dioxane: H₂ Potassium phosphate (0.38 g, 1.8 mmol) was added to the solution in O (5:1, 6.0 mL), followed by hydrazine (triphenylphosphine) palladium (50 mg, 0.04 mmol). 2-((2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl) Methyl phenylcarbamate (0.65 g, 1.6 mmol) was added to the reaction mixture, which was then stirred at 100 ° C for 12 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude compound was purified by column chromatography to give methyl 2-((2-methyl-4-(thiazol-5-yl)phenoxy)methyl)phenylcarbamate as a yellow viscous oil. (0.20 g, yield: 62%).¹ H NMR (DMSO-d ₆ ): δ 8.70 (s, 1H), 8.01-7.96 (m, 2H), 7.62 (bs, 1H), 7.41-7.37 (m, 3H), 7.32 (d, J = 7.2 Hz, 1H), 7.12 (t , J = 7.2 Hz, 1H), 6.99-6.96 (m, 1H), 5.13 (s, 2H), 2.99 (s, 3H), 2.30 (s, 3H). Preparation Example 7 Preparation of methyl 2-((2-methyl-4-(thiazol-4-yl)phenoxy)methyl)phenylcarbamate (Compound 1C-1) to 4-bromo in a nitrogen atmosphere Thiazole (0.1 g, 0.61 mmol) in 1,4-dioxane: H₂ Potassium phosphate (0.26 g, 1.2 mmol) was added to a solution of O (5:1, 6 mL), followed by hydrazine (triphenylphosphine) palladium (35 mg, 0.031 mmol). 2-((2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl) Methyl phenylcarbamate (0.38 g, 0.97 mmol) was added to the reaction mixture, which was then stirred at 100 ° C for 12 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude compound was purified by column chromatography to give methyl 2-((2-methyl-4-(thiazol-4-yl)phenoxy)methyl)phenylcarbamate as a yellow viscous oil. (0.15 g, yield: 69%).¹ H NMR (DMSO-d ₆ ): δ 9.14 (s, 1H), 9.03 (bs, 1H), 7.97 (s, 1H), 7.80-7.77 (m, 1H), 7.50 (d, J = 8.0 Hz, 2H), 7.41-7.30 (m , 2H), 7.20-7.17 (m, 1H), 7.04 (d, J = 8.4 Hz, 1H), 5.18 (s, 2H), 3.66 (s, 3H), 2.24 (s, 3H). Preparation Example 8 Preparation of methyl 2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)-3-methoxyphenylcarbamate (Compound 1A- 38) (1) 2-(Bromomethyl)-1-methoxy-3-nitrobenzene to 1-methoxy-2-methyl-3-nitrobenzene (2 g, 12.0 mmol) N-bromobutaneimine (2.56 g, 14.4 mmol) was added to a solution of carbon tetrachloride (20 ml), followed by the addition of benzamidine peroxide (0.14 g, 0.6 mmol). The reaction mixture was refluxed at 80 ° C for 6 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was diluted with EtOAc (EtOAc) (EtOAc)EtOAc. The crude product was purified by EtOAc EtOAcjjjjjj¹ H NMR (CDCl₃ ): δ 7.74-7.72 (m, 1H), 7.61-7.58 (m, 1H), 7.12 (t, J = 8.0 Hz, 1H), 4.91 (s, 2H), 4.01 (s, 3H). (2) 1-(2-Methoxy-6-nitrobenzyloxy)-4-bromo-2-toluene to 4-bromo-2-methylphenol (1.0 g, 5.3 mmol) in acetonitrile (10 ml Potassium carbonate (1.1 g, 6.4 mmol) was added to the solution, followed by 2-(bromomethyl)-1-methoxy-3-nitrobenzene (1.58 g, 6.4 mol), and the reaction mixture was Reflow at 80 ° C for 3 h. The reaction mixture was diluted with EtOAc EtOAc m. The crude product was purified by column chromatography eluting eluting elut elut eluting : 83.8%).¹ H NMR (CDCl₃ ): δ 7.47-7.39 (m, 2H), 7.24-7.21 (m, 2H), 7.16-7.14 (m, 1H), 6.79 (d, J = 9.2 Hz, 1H), 5.34 (s, 2H), 3.93 (s, 3H), 2.07 (s, 3H). (3) 2-((4-Bromo-2-methylphenoxy)methyl)-3-methoxyaniline to 1-(2-methoxy-6-nitrobenzyloxy) at 0 ° C Add copper chloride (0.21 g, 2.1 mmol) to a solution of 4-bromo-2-toluene (0.5 g, 1.4 mmol) in methanol (10 ml), followed by sodium borohydride (0.18 g, 5.0 (mmol), and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with EtOAc EtOAc EtOAc. It was used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.24-7.22 (m, 2H), 7.09 (t, J = 8.4 Hz, 1H), 6.95 (d, J = 9.2 Hz, 1H), 6.35-6.33 (m, 2H), 5.20 (s, 2H ), 4.13 (bs, 2H), 3.83 (s, 3H), 2.17 (s, 3H). (4) Methyl 2-((4-bromo-2-methylphenoxy)methyl)-3-methoxyphenylcarbamate to 2-((4-bromo-2-methylphenoxy) Add pyridine (98 mg, 1.2 mmol) to a solution of methyl)-3-methoxyaniline (0.2 g, 0.62 mmol) in dichloromethane (5.0 ml), followed by methyl chloroformate (70 mg , 0.74 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude product was purified by EtOAc EtOAc EtOAc EtOAc g, yield: 59%).¹ H NMR (CDCl₃ ): δ 7.82 (bs, 1H), 7.64 (d, J = 8.4 Hz, 1H), 7.29 (t, J = 8.4 Hz, 1H), 7.27-7.22 (m, 2H), 6.91 (d, J = 8.4 Hz, 1H), 6.65 (d, J = 8.4 Hz, 1H), 5.28 (s, 2H), 3.86 (s, 3H), 3.76 (s, 3H), 2.21 (s, 3H). (5) 2-((2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy) A Methyl 3-methoxyphenylcarbamate to 2-((4-bromo-2-methylphenoxy)methyl)-3-methoxyphenylaminocarboxylic acid under nitrogen atmosphere Methyl ester (0.15 g, 0.4 mmol) and potassium acetate (77 mg, 0.8 mmol) in 1,4-dioxane: H₂ To a mixture of O (5:1, 6 ml) was added hydrazine (triphenylphosphine) palladium (45 mg, 0.04 mmol) followed by bis(pinadol) diboron (0.15 g, 0.6 mmol). The reaction was then refluxed at 85 ° C for 12 h. After cooling to room temperature, the~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The crude compound was purified by column chromatography to yield 2-((2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxy) as a yellow viscous oil. Methyl boroborolan-2-yl)phenoxy)methyl)-3-methoxyphenylcarbamate (0.09 g, yield: 53%).¹ H NMR (CDCl₃ ): δ 7.88 (bs, 1H), 7.64-7.60 (m, 3H), 7.28 (t, J = 8.4 Hz, 1H), 7.06 (d, J = 8.4 Hz, 1H), 6.64 (d, J = 8.0) Hz, 1H), 5.30 (s, 2H), 3.86 (s, 3H), 3.74 (s, 3H), 2.24 (s, 3H), 1.26 (s, 9H). (6) Methyl 2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)-3-methoxyphenylcarbamate (Compound 1A-38) To 2-bromo-4-methylthiazole (0.041 g, 0.23 mmol) in 1,4-dioxane: H under nitrogen atmosphere₂ Sodium carbonate (50 mg, 0.50 mmol) and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride were added sequentially to the solution in O (4:1,6 ml). Methyl chloride complex (19 mg, 0.02 mmol) and 2-((2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan) Methyl-2-yl)phenoxy)methyl)-3-methoxyphenylcarbamate (0.10 g, 0.2 mmol). The reaction was stirred at 100 ° C for 12 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude compound was purified by column chromatography to afford 2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)-3-methoxy Methyl phenylaminocarbamate (49 mg, yield: 53.4%).¹ H NMR (CDCl₃ ): δ 7.85 (bs, 1H), 7.73 (s, 1H), 7.71-7.68 (m, 1H), 7.65 (d, J = 8.0 Hz, 1H), 7.30 (t, J = 8.0 Hz, 1H), 7.08 (d, J = 8.4 Hz, 1H), 6.79 (d, J = 1.2 Hz, 1H), 6.66 (d, J = 8.0 Hz, 1H), 5.33 (s, 2H), 3.88 (s, 3H), 3.76 (s, 3H), 2.48 (s, 3H), 2.29 (s, 3H). Preparation Example 9 Preparation of methyl 3-methyl-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenyl)carbamate (Compound 1A) -15) (1) (2-Methyl-6-nitrophenyl)methanol to 2-methyl-6-nitrobenzoic acid (2.0 g, 12.0 mmol) in dichloromethane (20 ml) Ethyl ruthenium chloride (3.47 g, 30.0 mmol) was added dropwise to the solution, followed by the addition of dimethylformamide (0.2 mL). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was evaporated to dryness under reduced pressure. Anhydrous THF was added thereto at 0 ° C to prepare a clear solution, followed by sodium borohydride (1.2 g, 36.0 mmol). The reaction mixture was stirred at room temperature for 1 h. It was quenched with water and extracted with ethyl acetate (3×50 mL) with NH₄ The solution was washed with EtOAc (3 mL, EtOAc). It was used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.69 (d, J = 8.0 Hz 1H), 7.45 (d, J = 7.60 Hz 1H 1H), 7.34 (t, J = 8.0 Hz, 1H), 4.69 (d, J = 7.2 Hz, 2H), 2.64 (t, J = 7.6 Hz 1H), 2.55 (s, 3H) (2) (2-Amino-6-methylphenyl)methanol at 0 ° C to 2-methyl-6-nitrophenyl) Copper chloride (1.7 g, 15.0 mmol) and sodium borohydride (1.8 g, 40.0 mmol) were added sequentially to a solution of methanol (1.0 g, 5.0 mmol) in methanol (10 ml). The reaction mixture was stirred at 0 ° C for 1 h. The reaction mixture was diluted with EtOAc (EtOAc) (EtOAc (EtOAc) 6-Methylphenyl)methanol (0.70 g, crude product). It was used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.01 (t, J = 7.6 Hz, 1H), 6.58 (t, J = 7.6 Hz 2H), 4.76 (s, 2H), 233 (s, 3H). (3) Methyl (2-(hydroxymethyl)-3-methylphenyl)carbamate to 2-amino-6-methylphenyl)methanol (0.70 g, 0.62 mmol) Pyridine (20 mg, 0.32 mmol) and methyl chloroformate (48 mg, 0.32 mmol) were added sequentially to a solution of 5.0 ml. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc (EtOAc (EtOAc)EtOAc. Methyl)methyl-3-phenylphenyl)carbamate (0.50 g, crude). It was used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.59 (s, 1H), 7.56 (d, J = 8.4 Hz, 1H), 7.20 (t, J = 8 Hz, 1H), 6.96 (d, J = 7.6 Hz, 1H), 4.74 (d, J = 5.2 Hz, 2H), 3.78 (s, 3H), 2.40 (s, 3H). (4) (2-(Hydroxymethyl)-3-methylphenyl)carbamic acid methyl ester at 0 ° C to (2-(hydroxymethyl)-3-methylphenyl) carbamic acid Add a solution of the ester (0.50 g, 0.62 mmol) in dichloromethane (5 mL The reaction mixture was stirred at 0 ° C for 1 h. The reaction mixture was diluted with EtOAc (EtOAc (EtOAc)EtOAc. Methyl (bromomethyl)-3-methylphenyl)carbamate (0.55 g, crude). It was used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.57 (bs, 1H), 7.22 (d, J = 8 Hz, 1H), 6.99 (d, J = 7.6 Hz, 1H), 6.68 (s, 1H), 4.54 (s, 2H), 3.80 ( s, 3H), 2.41 (s, 3H). (5) Methyl 2-((4-bromo-2-methylphenoxy)methyl)-3-methylphenyl)carbamate to 4-bromo-2-methylphenol at 0 ° C ( 0.40 g, 5.3 mmol) of potassium carbonate (0.59 g, 10.6 mmol) and methyl (2-(bromomethyl)-3-methylphenyl)carbamate were added sequentially to a solution of acetonitrile (10 ml) (0.55 g, 5.3 mmol). The reaction mixture was refluxed at 80 ° C for 3 h. After chilling at rt EtOAc (EtOAc)EtOAc. Methyl 2-((4-bromo-2-methylphenoxy)methyl)-3-methylphenyl)carbamate (0.54 g, crude). It was used as such in the next step without any further purification.¹ H NMR (CDCl₃ ): δ 7.75 (bs, 1H), 7.39 (bs, 1H), 7.30-7.26 (m, 3H), 7.03-6.97 (m, 1H), 6.85 (t, J = 4.8, 1H), 5.06 (s, 2H), 3.74 (s, 3H), 2.38 (s, 3H), 2.18 (s, 3H). (6) (3-Methyl-2-((2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Methyl phenoxy)methyl)phenyl)carbamate to (2-((4-bromo-2-methylphenoxy)methyl)-3-methylphenyl)amine under nitrogen atmosphere Methyl carbamic acid (0.150 g, 0.4 mmol) and potassium acetate (77 mg, 0.8 mmol) in 1,4-dioxane: H₂ To a mixture of O (5:1, 6 ml) was added hydrazine (triphenylphosphine) palladium (45 mg, 0.04 mmol) followed by bis(pinadol) diboron (0.15 g, 0.6 mmol). The reaction was then refluxed at 85 ° C for 12 h. After cooling to room temperature, the~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The crude compound was purified by column chromatography to afford (3-methyl-2-((2-methyl-4-(4,4,5,5,4-tetramethyl-1,3, Methyl 2-dioxaborolan-2-yl)phenoxy)methyl)phenyl)carbamate (0.09 g, yield: 53%).¹ H NMR (CDCl₃ ): δ 7.76 (d, J = 5.6 Hz 1H), 7.68 (d, J = 8.4 Hz 1H), 7.64 (s, 1H), 7.47 (bs, 1H), 7.28-7.24 (m, 1H), 6.99 ( t, J = 8.4 Hz, 2H), 5.11 (s, 2H), 3.72 (s, 3H), 2.39 (s, 3H), 2.21 (s, 3H), 1.34 (s, 12H). (7) Methyl 3-methyl-2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)phenyl)carbamate (Compound 1A- 15) 2-Bromo-4-methylthiazole (0.041 g, 0.23 mmol) in 1,4-dioxane: H under nitrogen atmosphere₂ Sodium carbonate (50 mg, 0.50 mmol) and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride were added sequentially to the solution in O (4:1,6 ml). Chloromethane complex (19 mg, 0.02 mmol) and (3-methyl-2-((2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-di) Methyl oxaborolan-2-yl)phenoxy)methyl)phenyl)carbamate (0.10 g, 0.20 mmol). The reaction was stirred at 100 ° C for 12 h. The reaction mixture was diluted with EtOAc (EtOAc)EtOAc. The crude compound was purified by column chromatography to afford 2-((2-methyl-4-(4-methylthiazol-2-yl)phenoxy)methyl)-3-methoxy Methyl phenylaminocarbamate (49 mg, yield: 53.4%).¹ H NMR (CDCl₃ ): δ 7.77-7.74 (m, 3H), 7.44 (bs, 1H), 7.28 (t, J = 8.2 Hz 1H), 7.02-6.98 (m, 2H), 6.81 (d, J = 8.0 Hz 1H), 5.13 (s, 2H), 3.74 (s, 3H), 2.48 (s, 3H), 2.41 (s, 3H), 2.26 (s, 3H). Representative compounds of the invention are illustrated in the following Tables 1 to 3, but the invention is not limited to such compounds. Except for the compounds obtained in Preparation Examples 1 to 9, the compounds shown in Tables 1 to 3 were produced by a method similar to that described in the methods or embodiments described in Preparation Examples 1 to 9. The abbreviations in Tables 1 to 3 are indicated below. F: fluorine, Cl: chlorine, Br: bromine, Me: methyl, Et: ethyl, iPr: isopropyl, t-Bu: tert-butyl, CF₃ :trifluoromethyl, Ph: phenyl, NO₂ : nitro, CN: cyano, OMe: methoxy. Table 1: Details of the compounds belonging to the synthesis of formula (1A) and¹ H NMR: Table 2: Details of the compounds belonging to the synthesis of formula (1B) and¹ H NMR: Table 3: Details of the compounds belonging to the synthesis of formula (1C) and¹ H NMR: The formulation examples are given below, in which the parts refer to parts by weight. Formulation Example 1 (Emulsible concentrate) 10 parts of each of the present compounds 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.). These components were mixed while stirring, thereby producing a 10% emulsifiable concentrate. Formulation Example 2 (wettable powder) 20 parts of each of the compounds of the present invention were added to 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of fine powder of aqueous synthetic cerium oxide, and a mixture of 54 parts of clay. in. These ingredients were mixed by a juice mixer while stirring, thereby producing a 20% wettable powder. Formulation Example 3 (Particles) Five parts of each of the present compounds were mixed with 2 parts of sodium dodecylbenzenesulfonate, 10 parts of bentonite and 83 parts of clay, followed by thorough stirring. A suitable amount of water is added and the mixture is further stirred. The mixture was granulated by a granulator and air dried to produce 5% granules. Formulation Example 4 (Dust) One part of each of the compounds 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 parts of isopropyl acid phosphate (PAP) and 93.7 parts of clay, followed by mixing and stirring by a juice mixer. Acetone was removed from it by evaporation to make a 1% powder formulation. Formulation Example 5 (Flowable Formulation) 20 parts of each of the present compounds and 20 parts of water 3 parts of polyoxyethylidenetrisylphenyl ether phosphate and triethanolamine ethyl 0.2 part of Rhodorsil^® 426R (made by RhodiaChimie) mixed. 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 suspension in 20% water. Test examples are given below to demonstrate that the compounds of the invention are useful as fungicide active ingredients. Test examples are given below to demonstrate that the compounds of the invention are suitable for use as active ingredients for fungicides.Test case 1 ( Monochamus , Cucumber for fungicidal test ) A solution of the compound of the invention (500 ppm) was sprayed onto fresh, healthy two week old courgette plants. The plants are air dried and freshly prepared spore suspension (1 × 10⁶ Cfu spores/ml) were inoculated. The inoculated plants were then placed in a greenhouse (25 ° C, humidity 60% and 16 L8D). The disease area rate was measured 12 days after inoculation, and the activity of the compound was shown to be a preventive value calculated according to the following equation. Prophylactic value = {1 - (area rate of disease in treatment) / (control disease area rate)} × 100. Compounds exhibiting a prophylactic value of 50% or greater are as follows: Compound No.: 1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A-9, 1A-10, 1A -12, 1A-13, 1A-14, 1A-15, 1A-16, 1A-17, 1A-18, 1A-22, 1A-25, 1A-28, 1A-29, 1A-30, 1A-31 , 1A-32, 1A-33, 1A-34, 1A-35, 1A-36, 1A-37, 1A-38, 1A-39, 1A-40, 1A-41, 1A-42, 1A-43, 1A -44, 1A-45, 1A-46, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1, 1C-2.Test case 2 ( Botrytis cinerea ( Botrytis Cinerea ) Fungicidal test ) A solution of the compound of the invention (500 ppm and 200 ppm) was sprayed onto fresh healthy courgette plants at least at the three leaf stage. The cotyledons of the treated plants are cut and the leaves are placed on a moist wipe on a plastic tray. 50 μl spore suspension (1×10) using a micropipette⁶ Cfu spores/ml) drip in the middle of the leaves. Then, a small piece of cotton wool was placed on the spore droplets, and 50 μl of the spore suspension was again dropped on the sheet. 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 to be a preventive value calculated according to the following equation. Prophylactic value = {1 - (radiated growth by treatment) / (radiation growth of control group)} × 100 Compounds exhibiting a prophylactic value of 50% or greater at a treatment concentration of 500 ppm are as follows: Compound number :1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A-9, 1A-10, 1A-12, 1A-13, 1A-14, 1A-15, 1A -16, 1A-17, 1A-18, 1A-22, 1A-23, 1A-25, 1A-29, 1A-30, 1A-33, 1A-34, 1A-37, 1A-38, 1A-39 , 1A-40, 1A-41, 1A-42, 1A-46, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1, 1C -2. Compounds that exhibit a prophylactic value of 50% or greater at a treatment concentration of 200 ppm are as follows: Compound number: 1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A- 9, 1A-10, 1A-12, 1A-13, 1A-14, 1A-15, 1A-17, 1A-18, 1A-25, 1A-29, 1A-30, 1A-33, 1A-37, 1A-38, 1A-39, 1A-40, 1A-41, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1, 1C- 2.Test case 3 ( Phytophthora infestans ( Phytophthora Infestans ) Fungicidal test ) A solution of the compound of the invention (500 ppm) was sprayed onto fresh healthy tomato plants at least at the three leaf stage. The plants are air dried and freshly prepared sporangia suspension (1 × 10⁶ Cfu travels spores/ml) inoculation. The inoculated plants were then placed in a dew chamber (20 ° C and humidity 100%). One day after the inoculation, the plants were transferred to a thermostatic chamber (20 ° C, humidity 80%, and 16 L8D). The disease area rate was measured 5 days after inoculation, and the activity of the compound was shown to be a prophylactic value calculated according to the following equation. Prophylactic value = {1 - (area rate of disease in treatment) / (control disease area rate)} × 100. Compounds exhibiting a prophylactic value of 50% or greater are as follows: Compound No.: 1A-4, 1A-5, 1A-12, 1A-15, 1A-17, 1A-29, 1A-35, 1A-36, 1A -37, 1A-40, 1A-49, 1C-1, 1C-2.Test case 4 ( Correct Magnaporthe oryzae ( Pyricularia Grisea ) Fungicidal test ) A solution of the compound of the invention (500 ppm) was sprayed onto fresh, healthy two week old chestnut plants. The plants are air dried and freshly prepared spore suspension (1 × 10⁶ Cfu spores/ml) were inoculated. The inoculated plants were then placed in a dew chamber (25 ° C and humidity 100%). One day after the inoculation, the plants were transferred to a thermostatic chamber (25 ° C, humidity 80%, and 16 L8D). The disease area rate was measured 5-7 days after inoculation, and the activity of the compound was shown to be a preventive value calculated according to the following equation. Prophylactic value = {1 - (area rate of disease in treatment) / (control disease area rate)} × 100. Compounds exhibiting a prophylactic value of 50% or greater are as follows: Compound No.: 1A-1, 1A-2, 1A-3, 1A-4, 1A-5, 1A-6, 1A-7, 1A-9, 1A -10, 1A-11, 1A-12, 1A-13, 1A-14, 1A-15, 1A-17, 1A-18, 1A-19, 1A-20, 1A-22, 1A-23, 1A-25 , 1A-26, 1A-29, 1A-30, 1A-33, 1A-35, 1A-36, 1A-37, 1A-38, 1A-39, 1A-40, 1A-41, 1A-42, 1A -43, 1A-44, 1A-45, 1A-46, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1B-1, 1B-2, 1C-1, 1C-2 . (Note) As described above, the present invention has been described by way of preferred embodiments of the present invention. However, it should be understood that the scope of the invention should be construed only by 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. 201711003382, filed on Jan. 30,,,,,,,,,,,,, Industrial Applicability The urethane compound of the present invention has a controlling action against plant diseases and is suitable as an active ingredient of a plant controlling agent.

Claims (10)

a urethane compound represented by the formula (1), Or a salt thereof, wherein R ₁ , R ₃ and R _{6 are the} same or different and each represents hydrogen, halogen, nitro, cyano, hydroxy, formamyl, carboxy, 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 a C _{1 - 6} alkyl group, a C _{1 - 6} alkoxycarbonyl group, a C _{1 - 6} haloalkyloxycarbonyl group, a cyano C _{1 - 6} alkyl group, a cyano C _{1 - 6} alkoxy group, a C _{2 - 6} alkenyl group , C _{2 - 6} alkenyl, halo, cyano, C _{2 - 6} alkenyl, C _{2 - 6} alkynyl, C _{2 - 6} alkynyl, halo, 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} cycloalkyl group, 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} halosulfonyl, C _{1 - 6} acyl halide alkylsulfinyl, C _{3 - 8} cycloalkyl sulfo acyl, C _{3 - 8} cycloalkyl acyl alkylsulfinyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkyl sulfonic acyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkylsulfinyl acyl, C _{2 - 6} alkenyloxy, C _{2 - 6} alkynyl group, C _{2 - 6} alkenyloxy halo , C _{2 - 6} alkynyl group halogen, C _{1 - 6} alkylsulfonyl group, C _{1 - 6} alkylsulfinyl acyl group, C _{1 - 6} alkylcarbonyl, C _{1 - 6} haloalkyl carbonyl, 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 a substituted arylsulfinyloxy group, optionally substituted aryl, or optionally substituted heteroaryl; R ₂ represents hydrogen, halogen or C _{1 - 6} alkyl; R ₄ and R _{5 are the} same Or different, and each represents hydrogen, halogen or C _{1 - 6} alkyl; R ₇ represents hydrogen, hydroxy, formyl, cyano, 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} haloalkyl carbonyl, C _{1 - 6} alkoxycarbonyl C _{2 - 6} haloalkoxy-carbonyl group, C _{2 - 6} alkenyl, C _{2 - 6} haloalkenyl, C _{2 - 6-cyano-alkenyl,} C _{2 - 6} alkynyl, C _{2 - 6} haloalkynyl, C _{2 - 6} cyanoalkynyl, C _{1 - 6} alkylsulfonyl, C _{1 - 6} alkylsulfinyl, C _{1 - 6} halosulfonyl, C _{1 - 6} haloalkyl sulfinyl, C _3--8 sulfo cycloalkyl acyl, C _{3 - 8} cycloalkyl acyl alkylsulfinyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkyl sulfonic acyl, C _{3 - 8} cycloalkyl C _{1 - 6} alkyl Sulfosyl, optionally substituted arylsulfonyl, optionally substituted arylsulfinyl, or optionally substituted aryl; R ₈ represents hydrogen or C _{1 - 6} alkyl; X and X ₁ independently represents oxygen or sulfur; Y represents oxygen or sulfur; Z represents oxygen or sulfur; l is an integer from 0 to 2; m is an integer from 0 to 3; n is an integer from 0 to 4; Or when n is greater than one, l, m or n may be the same or different. The requested item of a urethane compound or a salt thereof, wherein R ₁ is hydrogen, halo, nitro, C _{1 - 6} alkyl, C _{1 - 6} haloalkyl, C _{1 - 6} alkoxycarbonyl group, a cyano a C _{1 - 6} alkyl group, optionally substituted aryl group. The requested item 1 or 2 of the urethane compound or salt thereof, wherein R ₂ is hydrogen or C _{1 - 6} alkyl. The requested item 1 to 3, any one of amino acid ester compound or a salt thereof, wherein R ₃ is hydrogen, halogen or C _{1 - 6} alkyl. The request to any of items 1 to 4 carboxylic acid ester group of a compound or a salt thereof, wherein R ₄ and R ₅ each represents hydrogen or C _{1 - 6} alkyl. The requested item 1 to 5 of an urethane compound or a salt thereof, wherein R ₆ is hydrogen, halo, C _{1 - 6} alkyl or C _{1 - 6} alkoxy. The requested item 1 to 6, a urethane compound or a salt thereof according to any one of wherein R ₇ is hydrogen, C _{1 - 6} alkyl or C _{1 - 6} alkylcarbonyl. The urethane compound or a salt thereof according to any one of claims 1 to 7, wherein R ₈ is a C _{1 - 6} alkyl group. A plant disease control agent containing the urethane compound of any one of claims 1 to 8 or a salt thereof. A fungicide comprising the urethane compound of any one of claims 1 to 8 or a salt thereof.