Amide compound or salt thereof, fungicide for agriculture and horticulture containing same, and method for using same

Abstract

The present invention provides an excellent novel agricultural and horticultural pest control agent. The present invention relates to a compound represented by the following general formula [I], wherein each symbol is as described in the specification, or a salt thereof, agricultural and horticultural fungicides comprising them as active ingredients, and methods of using the same. # imgabs0 #

Description

[Technical Field]

[0001] The present invention relates to an amide compound or a salt thereof, an agricultural and horticultural fungicide containing these compounds as active ingredients, and a method for using the same. [Background Art]

[0002] Various compounds have been studied as agricultural and horticultural fungicides, and it has been reported that certain cycloalkyl-containing amide compounds can be used as insecticides, fungicides, and immunomodulators (see, for example, Patent Documents 1 to 4 and Non-Patent Document 1). However, these documents do not disclose the amide compounds of the present invention. [List of Cited Documents] [Patent Documents]

[0003] [Patent Document 1] DE 3422077 [Patent Document 2] WO 2000 / 024720 [Patent Document 3] WO 2019 / 099314 [Patent Document 4] WO 2008 / 005964 [Non-Patent Documents]

[0004] [Non-Patent Document 1] Huaxue Shiji, 34(2), 154 - 156, 2012 [Summary of the Invention] [Technical Problem]

[0005] In crop production in the fields of agriculture, horticulture, etc., the damage caused by various diseases, etc. is still huge, and diseases resistant to existing fungicides have emerged. In such a situation, it is desired to develop new agricultural and horticultural fungicides. In addition, labor-saving and automated application are recent trends in these fields, and from this perspective, it is necessary to develop agricultural and horticultural fungicides having characteristics suitable for various application methods such as seed treatment, small-volume application, and local application. That is, there is a need for agricultural and horticultural fungicides having medium environmental and thermal stability and sufficient systemic translocation and diffusibility throughout the crop plant or its vicinity. At the same time, in the context of the increasing demand for sustainable agriculture, the toxicity of agricultural chemicals and the impact on surrounding organisms and the surrounding environment are evaluated from various perspectives, and there is a need for fungicides having multi-faceted safety, medium persistence, biodegradability, environmental degradability, etc. [Solution to the Problem]

[0006] The inventors of the present invention conducted extensive research to solve the above problems. As a result, the inventors of the present invention found that the amide compound represented by the general formula [I] or a salt thereof has an excellent control effect on agricultural and horticultural diseases. The inventors of the present invention conducted further research and thus found that the amide compound or a salt thereof is applicable to various agrochemical applications and is excellent in physicochemical and biochemical properties. Based on these findings, the present invention has been completed.

[0007] That is, the present invention relates to the following. [1] A compound represented by the general formula [I] or a salt thereof Wherein R 1 and R 5 may be the same or different and each represents (a1) A hydrogen atom; (a2) A halogen atom; (a3) A cyano group; (a4) A nitro group; (a5) A hydroxyl group; (a6) A pentafluorosulfanyl group; (a7) A (C1-C6) alkyl group; (a8) A halo(C1-C6)alkyl group; (a9) A (C2-C6) alkenyl group; (a10) A halo(C2-C6)alkenyl group; (a11) A (C2-C6) alkynyl group; (a12) A halo(C2-C6)alkynyl group; (a13) A (C3-C6) cycloalkyl group; (a14) A (C3-C6) cycloalkenyl group; (a15) A halo(C3-C6)cycloalkyl group; (a16) A (C3-C6) cycloalkyl(C1-C6)alkyl group; (a17) A (C3-C6) cycloalkyl(C3-C6)cycloalkyl group; (a18) A halo(C3-C6)cycloalkyl(C1-C6)alkyl group; (a19) A halo(C3-C6)cycloalkyl halo(C1-C6)alkyl group; (a20) A cyano(C1-C6)alkyl group; (a21) A cyano(C3-C6)cycloalkyl group; (a22) A hydroxy(C1-C6)alkyl group; (a23) A (C1-C6) alkoxy(C1-C6)alkyl group; (a24) halo(C1-C6)alkoxy(C1-C6)alkyl; (a25)(C3-C6)cycloalkoxy(C1-C6)alkyl; (a26) halo(C3-C6)cycloalkoxy(C1-C6)alkyl; (a27)(C1-C6)alkylthio(C1-C6)alkyl; (a28) halo(C1-C6)alkylthio(C1-C6)alkyl; (a29)(C1-C6)alkylthiohalo(C1-C6)alkyl; (a30)(C1-C6)alkylsulfinyl(C1-C6)alkyl; (a31) halo(C1-C6)alkylsulfinyl(C1-C6)alkyl; (a32)(C1-C6)alkylsulfinylhalo(C1-C6)alkyl; (a33)(C1-C6)alkylsulfonyl(C1-C6)alkyl; (a34) halo(C1-C6)alkylsulfonyl(C1-C6)alkyl; (a35)(C1-C6)alkylsulfonylhalo(C1-C6)alkyl; (a36)(C1-C6)alkoxy(C2-C6)alkenyl; (a37)(C1-C6)alkoxy(C2-C6)alkynyl; (a38)(C1-C10)alkoxy; (a39) halo(C1-C10)alkoxy; (a40)(C2-C6)alkenyloxy; (a41) halo(C2-C6)alkenyloxy; (a42)(C2-C6)alkynyloxy; (a43) halo(C2-C6)alkynyloxy; (a44)(C3-C7)cycloalkoxy; (a45)(C3-C6)cycloalkyl(C1-C6)alkoxy; (a46)(C1-C6)alkoxy(C1-C6)alkoxy; (a47)(C1-C6)alkylcarbonyloxy; (a48)(C3-C6)cycloalkylcarbonyloxy; (a49)(C3-C6)cycloalkenyl; (a50)(C1-C6)alkylthio; (a51)Halogenated (C1-C6) alkylthio; (a52)(C1-C6) alkylsulfinyl; (a53)Halogenated (C1-C6) alkylsulfinyl; (a54)(C1-C6) alkylsulfonyl; (a55)Halogenated (C1-C6) alkylsulfonyl; (a56)Z group; (a57)Z(C1-C6) alkyl; (a58)Z(C1-C6) alkoxy; (a59)Z halogenated (C1-C6) alkoxy; (a60)Z(C2-C6) alkenyl; (a61)Z halogenated (C2-C6) alkenyl; (a62)Z(C2-C6) alkynyl; (a63)Z halogenated (C2-C6) alkynyl; (a64)Z(C3-C6) cycloalkyl; (a65)Z halogenated (C3-C6) cycloalkyl; (a66)Z carbonyl oxy; (a67)Z(C1-C6) alkylthio; (a68)N-mono-Z(C1-C6) alkylamino; (a69)N-(C1-C6) alkyl-N-Z(C1-C6) alkylamino; (a70)N-Z(C1-C6) alkyl-N-Z(C1-C6) alkylamino; (a71)Z oxy; (a72)Z sulfonyl amino; (a73)Z thio; (a74)Z sulfinyl; (a75)Z sulfonyl; (a76)Z carbonyl amino; (a77)N-((C1-C6) alkyl)-N-(Z carbonyl) amino; (a78)N-mono-(C1-C6) alkoxycarbonyl amino; (a79)N-((C1-C6) alkoxycarbonyl)-N-((C1-C6) alkyl) amino; (a80)N-(C1-C6) alkyl-N-Z amino carbonyl; (a81)Z carbonyl; (a82)Z(C1-C6) alkylcarbonyl amino; (a83)Z amino; (a84) Amino; (a85) N-Mono-(C1-C6)alkylamino; (a86) N-(C1-C6)Alkyl-N-(C1-C6)alkylamino; (a87) N-Mono-(C2-C6)alkenylamino; (a88) N-(C2-C6)Alkenyl-N-(C2-C6)alkenylamino; (a89) N-Mono-(C2-C6)alkynylamino; (a90) N-(C2-C6)Alkynyl-N-(C2-C6)alkynylamino; (a91) (C1-C6)Alkylcarbonylamino; (a92) (C3-C6)Cycloalkylcarbonylamino; (a93) Aminothioalkyl; (a94) Aminosulfinyl; (a95) Aminosulfonyl; (a96) N-Mono-(C1-C6)alkylaminothioalkyl; (a97) N-(C1-C6)Alkyl-N-(C1-C6)alkylaminothioalkyl; (a98) N-Mono-(C1-C6)alkylaminosulfinyl; (a99) N-(C1-C6)Alkyl-N-(C1-C6)alkylaminosulfinyl; (a100) N-Mono-(C1-C6)alkylaminosulfonyl; (a101) N-(C1-C6)Alkyl-N-(C1-C6)alkylaminosulfonyl; (a102) Aminocarbonyl; (a103) N-Mono-(C1-C6)alkylaminocarbonyl; (a104) N-(C1-C6)Alkyl-N-(C1-C6)alkylaminocarbonyl; (a105) (C1-C6)Alkylcarbonyl; (a106) (C3-C6)Cycloalkylcarbonyl; (a107) (C1-C6)Alkoxycarbonyl; (a108) Aminooxy; (a109) Hydroxyamino; (a110) (C3-C6)Cycloalkoxycarbonyl; (a111) Formyl; (a112) Carboxy; (a113) oxido group; (a114) (C1-C12) alkylsilyl; (a115) halo(C3-C6) cycloalkoxy; (a116) Z-halo(C1-C6) alkyl; (a117) N-Z aminosulfonyl; (a118) Z,Z(C1-C6) alkoxy; (a119) (C1-C6) alkoxy(C1-C6) alkoxy(C1-C6) alkoxy; (a120) N-((C1-C6) alkoxycarbonyl)-N-Z amino; (a121) (C3-C6) cycloalkoxy; (a122) halo(C1-C6) alkylcarbonylamino; (a123) (C3-C6) cycloalkylamino; (a124) Z aminocarbonyl; (a125) (C3-C6) cycloalkylaminocarbonyl; or (a126) a group represented by formula A1, A2, A3, A4 or A5 Z represents (b1) phenyl; (b2)A substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the group consisting of: a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C2-C6)alkenyl group, a halo(C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyloxy group, a halo(C2-C6)alkenyloxy group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfonyloxy group, a halo(C1-C6)alkylsulfonyloxy group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, a (C2-C6)alkenylthio group, a halo(C2-C6)alkenylthio group, a (C2-C6)alkenylsulfinyl group, a halo(C2-C6)alkenylsulfinyl group, a (C2-C6)alkenylsulfonyl group, a halo(C2-C6)alkenylsulfonyl group, an N-mono-(C1-C6)alkylamino group, an N,N-di-(C1-C6)alkylamino group in which the alkyl groups may be the same or different, a (C1-C6)alkylsulfonylamino group, a halo(C1-C6)alkylsulfonylamino group, a (C1-C6)alkylcarbonyl group, a formyl group, a halo(C1-C6)alkylcarbonyl group, a hydroxy(C1-C6)alkyl group, a (C1-C6)alkoxycarbonyl group, an aminocarbonyl group, a (C1-C12)alkylsilyl group, a phenoxy group, and a phenyl group; (b3)A heterocyclic group; (b4)A heterocyclic group having, on the ring, 1 to 3 substituents independently selected from the group consisting of: a halogen atom, a hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, and a (C1-C6)alkoxycarbonyl group; (b5)A naphthyl group; (b6)An indanyl group; or (b7)An indenyl group, R 2 and R 3 may be the same or different and each represents (c1)A (C1-C6)alkyl group; or (c2)A halogen atom, R4 represents (d1)A hydrogen atom; (d2)A (C1-C6)alkyl group; (d3) Halo(C1-C6)alkyl; (d4)(C1-C6)Alkoxy; (d5) Halo(C1-C6)alkoxy; (d6)(C2-C6)Alkenyl; (d7)(C2-C6)Alkynyl; (d8)(C3-C6)Cycloalkyl; (d9)(C3-C6)Cycloalkyl(C1-C6)alkyl; (d10)(C1-C6)Alkoxy(C1-C6)alkyl; (d11)(C1-C6)Alkylcarbonyl; (d12)(C1-C6)Alkoxycarbonyl; (d13)(C3-C6)Cycloalkylcarbonyl; (d14)(C1-C6)Alkoxy(C1-C6)alkylcarbonyl; (d15) Halo(C1-C6)alkylcarbonyl; (d16)(C1-C6)Alkoxycarbonyl(C1-C6)alkyl; (d17) Amino(C1-C6)alkylcarbonyl; (d18) N-Mono-(C1-C6)alkylamino(C1-C6)alkylcarbonyl; (d19) N,N-Di-(C1-C6)alkylamino(C1-C6)alkylcarbonyl; (d20)(C1-C6)Alkylthio; (d21) Halo(C1-C6)alkylthio; (d22)(C1-C6)Alkylsulfinyl; (d23) Halo(C1-C6)alkylsulfinyl; (d24)(C1-C6)Alkylsulfonyl; (d25) Halo(C1-C6)alkylsulfonyl; (d26)(C3-C6)Cycloalkylthio; (d27)(C3-C6)Cycloalkylsulfinyl; (d28)(C3-C6)Cycloalkylsulfonyl; (d29) Amino(C1-C6)alkyl; (d30) N-Mono-(C1-C6)alkylamino(C1-C6)alkyl; (d31) N,N-Di-(C1-C6)alkylamino(C1-C6)alkyl; (d32) Z(C1-C6)alkyl; (d33)Z group; (d34)Z oxy group; (d35)Z carbonyl group; (d36)(C2-C6) alkenyloxycarbonyl group; (d37)(C2-C6) alkynyloxycarbonyl group; (d38)(C2-C6) alkenylcarbonyl group; (d39) amino (C1-C6) alkylcarbonyl group; (d40) N-mono-(C1-C6) alkylamino (C1-C6) alkylcarbonyl group; (d41) N,N-di-(C1-C6) alkylamino (C1-C6) alkylcarbonyl group; (d42) Z (C1-C6) alkylcarbonyl group; or (d43) Z (C1-C6) alkoxycarbonyl group, Two Rs 1 may be bonded to each other to form a ring structure represented by the formula R 1-1 , R 1-2 , R 1-3 or R 1-4 Each ring structure contains the carbon atoms to which they are bonded Two Rs 5 may be bonded to each other to form a ring structure represented by the formula R 5-1 or R 5-2 Each ring structure contains the carbon atoms to which they are bonded R 4 and R 5 may be bonded to each other to form a ring structure containing a partial structure represented by the formula R 4-5-1 or R 4-5-2 and the carbon and nitrogen atoms to which they are bonded X represents an oxygen atom or a sulfur atom, Ar 1 represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group or a group represented by the formula #1, #2 or #3 Ar 2 represents a group represented by the formula: Ar 2-1 , Ar 2-2 , Ar 2-3 , Ar 2-4 , Ar 2-5 , Ar 2-6, Ar 2-7 , Ar 2-8 , Ar 2-9 , Ar 2-10 , Ar 2-11 , Ar 2-12 , Ar 2-13 , Ar 2-14 , Ar 2-15 , Ar 2-16 , Ar 2-17 , Ar 2-18 , Ar 2-19 , Ar 2-20 , Ar 2-21 , Ar 2-22 or Ar 2-23 m represents 1, 2, 3, 4 or 5, and n represents 1, 2, 3, 4 or 5, provided that the compound represented by the following formula DC1 and its salts are excluded

[0008] [2] The compound or its salt as described in [1], wherein R 1 and R 5 may be the same or different and each is (a1) a hydrogen atom; (a2) a halogen atom; (a3) a cyano group; (a4) a nitro group; (a5) a hydroxyl group; (a7) a (C1-C6) alkyl group; (a8) a halo(C1-C6) alkyl group; (a9) a (C2-C6) alkenyl group; (a10) a halo(C2-C6) alkenyl group; (a11) a (C2-C6) alkynyl group; (a12) a halo(C2-C6) alkynyl group; (a13) a (C3-C6) cycloalkyl group; (a14) a (C3-C6) cycloalkenyl group; (a15) a halo(C3-C6) cycloalkyl group; (a16) a (C3-C6) cycloalkyl(C1-C6) alkyl group; (a17) a (C3-C6) cycloalkyl(C3-C6) cycloalkyl group; (a22) a hydroxy(C1-C6) alkyl group; (a23) (C1-C6) alkoxy(C1-C6)alkyl; (a24) halo(C1-C6)alkoxy(C1-C6)alkyl; (a25) (C3-C6) cycloalkoxy(C1-C6)alkyl; (a26) halo(C3-C6)cycloalkoxy(C1-C6)alkyl; (a27) (C1-C6) alkylthio(C1-C6)alkyl; (a36) (C1-C6) alkoxy(C2-C6)alkenyl; (a37) (C1-C6) alkoxy(C2-C6)alkynyl; (a38) (C1-C10) alkoxy; (a39) halo(C1-C10)alkoxy; (a40) (C2-C6) alkenyloxy; (a41) halo(C2-C6)alkenyloxy; (a42) (C2-C6) alkynyloxy; (a43) halo(C2-C6)alkynyloxy; (a44) (C3-C7) cycloalkoxy; (a45) (C3-C6) cycloalkyl(C1-C6)alkoxy; (a46) (C1-C6) alkoxy(C1-C6)alkoxy; (a47) (C1-C6) alkylcarbonyloxy; (a48) (C3-C6) cycloalkylcarbonyloxy; (a49) (C3-C6) cycloalkenyl; (a50) (C1-C6) alkylthio; (a51) halo(C1-C6)alkylthio; (a52) (C1-C6) alkylsulfinyl; (a53) halo(C1-C6)alkylsulfinyl; (a54) (C1-C6) alkylsulfonyl; (a55) halo(C1-C6)alkylsulfonyl; (a56) Z group; (a57) Z(C1-C6)alkyl; (a58) Z(C1-C6)alkoxy; (a59) Z halo(C1-C6)alkoxy; (a62) Z(C2-C6)alkynyl; (a66)Z-carbonyloxy; (a67)Z(C1-C6)alkylthio; (a68)N-mono-Z(C1-C6)alkylamino; (a69)N-(C1-C6)alkyl-N-Z(C1-C6)alkylamino; (a70)N-Z(C1-C6)alkyl-N-Z(C1-C6)alkylamino; (a71)Z-oxy; (a72)Z-sulfonylamino; (a73)Z-thio; (a74)Z-sulfinyl; (a75)Z-sulfonyl; (a76)Z-carbonylamino; (a77)N-((C1-C6)alkyl)-N-(Z-carbonyl)amino; (a78)N-mono-(C1-C6)alkoxycarbonylamino; (a79)N-((C1-C6)alkoxycarbonyl)-N-((C1-C6)alkyl)amino; (a80)N-(C1-C6)alkyl-N-Z-aminocarbonyl; (a81)Z-carbonyl; (a82)Z(C1-C6)alkylcarbonylamino; (a83)Z-amino; (a84)amino; (a85)N-mono-(C1-C6)alkylamino; (a86)N-(C1-C6)alkyl-N-(C1-C6)alkylamino; (a87)N-mono-(C2-C6)alkenylamino; (a88)N-(C2-C6)alkenyl-N-(C2-C6)alkenylamino; (a89)N-mono-(C2-C6)alkynylamino; (a90)N-(C2-C6)alkynyl-N-(C2-C6)alkynylamino; (a91)(C1-C6)alkylcarbonylamino; (a92)(C3-C6)cycloalkylcarbonylamino; (a93)aminothio; (a94)aminosulfinyl; (a95)aminosulfonyl; (a96)N-mono-(C1-C6)alkylaminothio; (a97)N-(C1-C6)alkyl-N-(C1-C6)alkylaminothioalkyl; (a98)N-mono-(C1-C6)alkylaminosulfinyl; (a99)N-(C1-C6)alkyl-N-(C1-C6)alkylaminosulfinyl; (a100)N-mono-(C1-C6)alkylaminosulfonyl; (a101)N-(C1-C6)alkyl-N-(C1-C6)alkylaminosulfonyl; (a102)aminocarbonyl; (a103)N-mono-(C1-C6)alkylaminocarbonyl; (a104)N-(C1-C6)alkyl-N-(C1-C6)alkylaminocarbonyl; (a105)(C1-C6)alkylcarbonyl; (a106)(C3-C6)cycloalkylcarbonyl; (a107)(C1-C6)alkoxycarbonyl; (a108)aminooxy; (a109)hydroxyamino; (a110)(C3-C6)cycloalkoxycarbonyl; (a111)formyl; (a112)carboxy; (a113)oxo; (a114)(C1-C12)alkylsilyl; (a120)N-((C1-C6)alkoxycarbonyl)-N-Z amino; (a121)(C3-C6)cycloalkoxy; (a122)halo(C1-C6)alkylcarbonylamino; (a123)(C3-C6)cycloalkylamino; (a124)Z aminocarbonyl; (a125)(C3-C6)cycloalkylaminocarbonyl; or (a126)a group represented by formula A1, A2, A3, A4 or A5 R 2 and R 3 may be the same or different and each is a halogen atom, R 4 is (d1)a hydrogen atom; (d2)(C1-C6)alkyl; (d4) (C1-C6) alkoxy; (d6) (C2-C6) alkenyl; (d9) (C3-C6) cycloalkyl(C1-C6) alkyl; (d10) (C1-C6) alkoxy(C1-C6) alkyl; (d11) (C1-C6) alkylcarbonyl; (d12) (C1-C6) alkoxycarbonyl; (d14) (C1-C6) alkoxy(C1-C6) alkylcarbonyl; (d16) (C1-C6) alkoxycarbonyl(C1-C6) alkyl; (d20) (C1-C6) alkylthio; (d22) (C1-C6) alkylsulfinyl; (d24) (C1-C6) alkylsulfonyl; (d28) (C3-C6) cycloalkylsulfonyl; (d29) amino(C1-C6) alkyl; (d30) N-mono-(C1-C6) alkylamino(C1-C6) alkyl; (d31) N,N-di-(C1-C6) alkylamino(C1-C6) alkyl; (d32) Z(C1-C6) alkyl; (d33) Z group; (d35) Z carbonyl; (d36) (C2-C6) alkenyloxycarbonyl; (d37) (C2-C6) alkynyloxycarbonyl; (d38) (C2-C6) alkenylcarbonyl; (d39) amino(C1-C6) alkylcarbonyl; (d40) N-mono-(C1-C6) alkylamino(C1-C6) alkylcarbonyl; or (d41) N,N-di-(C1-C6) alkylamino(C1-C6) alkylcarbonyl, R 4 and R 5 may be bonded to each other to form a ring structure containing the partial structure represented by the formula R 4-5-1 and the carbon and nitrogen atoms to which they are bonded and Ar 2 is a group represented by the formula: Ar 2-1 、Ar 2-2 、Ar2-3 , Ar 2-4 , Ar 2-5 , Ar 2-6 , Ar 2-7 , Ar 2-8 , Ar 2-9 , Ar 2-10 , Ar 2-11 , Ar 2-12 , Ar 2-13 , Ar 2-14 , Ar 2-17 , Ar 2-18 , Ar 2-19 or Ar 2-20

[0009] [3] The compound or its salt as described in [2], wherein R 1 and R 5 may be the same or different and each is (a1) a hydrogen atom; (a2) a halogen atom; (a3) a cyano group; (a4) a nitro group; (a5) a hydroxyl group; (a7) a (C1-C6) alkyl group; (a8) a halo(C1-C6) alkyl group; (a9) a (C2-C6) alkenyl group; (a11) a (C2-C6) alkynyl group; (a13) a (C3-C6) cycloalkyl group; (a14) a (C3-C6) cycloalkenyl group; (a22) a hydroxy(C1-C6) alkyl group; (a36) a (C1-C6) alkoxy(C2-C6) alkenyl group; (a38) a (C1-C10) alkoxy group; (a39) a halo(C1-C10) alkoxy group; (a40) a (C2-C6) alkenyloxy group; (a44) a (C3-C7) cycloalkoxy group; (a45) a (C3-C6) cycloalkyl(C1-C6) alkoxy group; (a46) a (C1-C6) alkoxy(C1-C6) alkoxy group; (a47) a (C1-C6) alkylcarbonyloxy group; (a48) a (C3-C6) cycloalkylcarbonyloxy group; (a50) (C1-C6) alkylthio (a51) halo(C1-C6) alkylthio (a52) (C1-C6) alkylsulfinyl (a54) (C1-C6) alkylsulfonyl (a56) Z group (a57) Z(C1-C6) alkyl (a58) Z(C1-C6) alkoxy (a62) Z(C2-C6) alkynyl (a66) Z carbonyloxy (a67) Z(C1-C6) alkylthio (a68) N-mono-Z(C1-C6) alkylamino (a69) N-(C1-C6) alkyl-N-Z(C1-C6) alkylamino (a70) N-Z(C1-C6) alkyl-N-Z(C1-C6) alkylamino (a71) Z oxy (a72) Z sulfonylamino (a76) Z carbonylamino (a77) N-((C1-C6) alkyl)-N-(Z carbonyl) amino (a78) N-mono-(C1-C6) alkoxycarbonylamino (a79) N-((C1-C6) alkoxycarbonyl)-N-((C1-C6) alkyl) amino (a81) Z carbonyl (a82) Z(C1-C6) alkylcarbonylamino (a83) Z amino (a84) amino (a85) N-mono-(C1-C6) alkylamino (a86) N-(C1-C6) alkyl-N-(C1-C6) alkylamino (a87) N-mono-(C2-C6) alkenylamino (a91) (C1-C6) alkylcarbonylamino (a92) (C3-C6) cycloalkylcarbonylamino (a95) aminosulfonyl (a100) N-mono-(C1-C6) alkylaminosulfonyl (a101) N-(C1-C6) alkyl-N-(C1-C6) alkylaminosulfonyl (a102)aminocarbonyl; (a103)N - mono-(C1 - C6)alkylaminocarbonyl; (a104)N-(C1 - C6)alkyl - N-(C1 - C6)alkylaminocarbonyl; (a105)(C1 - C6)alkylcarbonyl; (a106)(C3 - C6)cycloalkylcarbonyl; (a107)(C1 - C6)alkoxycarbonyl; (a111)formyl; (a112)carboxy; (a113)oxo; (a114)(C1 - C12)alkylsilyl; (a120)N - ((C1 - C6)alkoxycarbonyl)-N - Z amino; (a121)(C3 - C6)cycloalkoxy; (a122)halo(C1 - C6)alkylcarbonylamino; (a123)(C3 - C6)cycloalkylamino; (a124)Z aminocarbonyl; (a125)(C3 - C6)cycloalkylaminocarbonyl; or (a126)a group represented by formula A1, A2, A3, A4 or A5 R 4 is (d1)a hydrogen atom; (d2)(C1 - C6)alkyl; (d4)(C1 - C6)alkoxy; (d6)(C2 - C6)alkenyl; (d10)(C1 - C6)alkoxy(C1 - C6)alkyl; (d11)(C1 - C6)alkylcarbonyl; (d12)(C1 - C6)alkoxycarbonyl; (d14)(C1 - C6)alkoxy(C1 - C6)alkylcarbonyl; (d16)(C1 - C6)alkoxycarbonyl(C1 - C6)alkyl; (d22)(C1 - C6)alkylsulfinyl; (d24)(C1 - C6)alkylsulfonyl; (d28)(C3 - C6)cycloalkylsulfonyl; (d31)N,N - bis-(C1 - C6)alkylamino(C1 - C6)alkyl; (d32)Z(C1 - C6)alkyl; (d36)(C2 - C6)alkenyloxycarbonyl; (d38)(C2 - C6)alkenylcarbonyl; (d39)amino(C1 - C6)alkylcarbonyl; or (d41)N,N - bis-(C1 - C6)alkylamino(C1 - C6)alkylcarbonyl, and X is an oxygen atom.

[0010] [4] An agricultural and horticultural fungicide comprising the compound of [1] above or a salt thereof as an active ingredient, [5] An agricultural and horticultural fungicide comprising the compound of [2] above or a salt thereof as an active ingredient, [6] An agricultural and horticultural fungicide comprising the compound of [3] above or a salt thereof as an active ingredient, [7] A method for controlling agricultural and horticultural diseases, the method comprising treating a plant or soil with an effective amount of the agricultural and horticultural fungicide of [4] above, [8] A method for controlling agricultural and horticultural diseases, the method comprising treating a plant or soil with an effective amount of the agricultural and horticultural fungicide of [5] above, [9] A method for controlling agricultural and horticultural diseases, the method comprising treating a plant or soil with an effective amount of the agricultural and horticultural fungicide of [6] above,

[10] Use of the compound of [1] above or a salt thereof as a fungicide,

[11] Use of the compound of [2] above or a salt thereof as a fungicide, and

[12] Use of the compound of [3] above or a salt thereof as a fungicide. [Advantages of the present invention]

[0011] The amide compound of the present invention or a salt thereof has excellent control effects as an agricultural and horticultural fungicide. In particular, the amide compound of the present invention or a salt thereof is very effective against the following: Alternaria brassicae leaf spot, Phytophthora infestans of tomato, Botrytis cinerea of cucumber, Colletotrichum orbiculare of cucumber, Magnaporthe oryzae, Venturia inaequalis of apple, Erysiphe graminis f. sp. hordei of barley, Septoria tritici blotch of wheat, Sclerotinia sclerotiorum of cucumber, Physalospora piricola, Botrytis cinerea of grape, sudden death syndrome of soybean, fusarium ear blight of barley, wheat, etc., Sclerotinia sclerotiorum of cruciferae and brown spot of rice. [Detailed embodiments]

[0012] In the definition of the general formula [I] of the amide compound of the present invention or its salt, "halo" means "halogen atom" and represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

[0013] “(C1-C6)alkyl” means a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 2,3-dimethylpropyl, 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, isohexyl, 2-hexyl, 3-hexyl, 2-methylpentyl, 3-methylpentyl, 1,1,2-trimethylpropyl, 3,3-dimethylbutyl, etc. “(C2-C6)alkenyl” means a straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms, such as vinyl, allyl, isopropenyl, 1-butenyl, 2-butenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, pentenyl, 1-hexenyl, 3,3-dimethyl-1-butenyl, etc. “(C2-C6)alkynyl” means a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl, 2-methyl-3-propynyl, pentynyl, 1-hexynyl, 3-methyl-1-butynyl, 3,3-dimethyl-1-butynyl, etc.

[0014] “(C3-C6)cycloalkyl” means a cyclic alkyl group having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “(C3-C6)cycloalkenyl” means a cyclic alkenyl group having 3 to 6 atoms, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, etc. “(C1-C6)alkoxy” means a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy, tert-pentyloxy, neopentyloxy, 2,3-dimethylpropoxy, 1-ethylpropoxy, 1-methylbutoxy, n-hexyloxy, isohexyloxy, 1,1,2-trimethylpropoxy, etc. “(C3-C6)cycloalkoxy” means a cyclic alkoxy group having 1 to 6 carbon atoms, such as cyclopropoxy, cyclobutoxy, cyclopropoxy, cyclobutoxy, etc.

[0015] “(C2-C6)alkenyloxy” means a straight-chain or branched-chain alkenyloxy group having 2 to 6 carbon atoms, such as allyloxy, butenyloxy, pentyloxy, hexyloxy, etc. “(C2-C6)alkynyloxy” means a straight-chain or branched-chain alkynyloxy group having 2 to 6 carbon atoms, such as propynyloxy, butynyloxy, pentyloxy, hexyloxy, etc.

[0016] “(C1-C6) alkylthio” means a straight-chain or branched-chain alkylthio having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, n-pentylthio, isopentylthio, tert-pentylthio, neopentylthio, 2,3-dimethylpropylthio, 1-ethylpropylthio, 1-methylbutylthio, n-hexylthio, isohexylthio, 1,1,2-trimethylpropylthio, etc. “(C1-C6) alkylsulfinyl” means a straight-chain or branched-chain alkylsulfinyl having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, n-pentylsulfinyl, isopentylsulfinyl, tert-pentylsulfinyl, neopentylsulfinyl, 2,3-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1-methylbutylsulfinyl, n-hexylsulfinyl, isohexylsulfinyl, 1,1,2-trimethylpropylsulfinyl, etc. “(C1-C6) alkylsulfonyl” means a straight-chain or branched-chain alkylsulfonyl having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, n-pentylsulfonyl, isopentylsulfonyl, tert-pentylsulfonyl, neopentylsulfonyl, 2,3-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1-methylbutylsulfonyl, n-hexylsulfonyl, isohexylsulfonyl, 1,1,2-trimethylpropylsulfonyl, etc.

[0017] “Hydroxy(C1-C6)alkyl” means a straight-chain or branched-chain alkyl having 1 to 6 carbon atoms, such as 2-hydroxypropyl, 2-hydroxy-2-methyl-propyl, etc.

[0018] “(C1-C6) alkylcarbonyl” means an alkylcarbonyl having 2 to 7 carbon atoms, such as an alkylcarbonyl having the above (C1-C6) alkyl, such as acetyl, propionyl, butyryl, 2-methylpropionyl, valeryl, 2-methylbutyryl, 3-methylbutyryl, pivaloyl, hexanoyl, etc.

[0019] “(C1-C6) alkoxycarbonyl” means an alkoxycarbonyl having 2 to 7 carbon atoms, such as an alkoxycarbonyl having the above (C1-C6) alkoxy, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, etc.

[0020] “(C1-C6) alkyloxycarbonyl” means a straight-chain or branched-chain alkyloxycarbonyl having 2 to 7 carbon atoms, such as 1-oxoethoxy, 1-oxopropoxy, etc. “(C3-C6) cycloalkyloxycarbonyl” means a straight-chain or branched-chain alkyloxycarbonyl having 4 to 7 carbon atoms, such as 2-cyclopropyl-1-oxoethoxy, 2-cyclobutyl-1-oxoethoxy, etc.

[0021] The above-mentioned “(C1-C6) alkyl”, “(C3-C6) cycloalkyl”, “(C1-C6) alkylthio”, “(C1-C6) alkylsulfinyl”, “(C1-C6) alkylsulfonyl”, “(C2-C6) alkenyl”, “(C2-C6) alkynyl”, “(C3-C6) cycloalkyl”, “(C1-C10) alkoxy”, “(C2-C6) alkenyloxy” and “(C2-C6) alkynyloxy” can be substituted by one or more halogen atoms at one or more substitutable positions, and in the case where any of the above groups is substituted by two or more halogen atoms, the halogen atoms can be the same or different.

[0022] The above-mentioned “group substituted by one or more halogen atoms at one or more substitutable positions” is respectively represented as “halo (C1-C6) alkyl”, “halo (C3-C6) cycloalkyl”, “halo (C1-C6) alkylthio”, “halo (C1-C6) alkylsulfinyl”, “halo (C1-C6) alkylsulfonyl”, “halo (C2-C6) alkenyl”, “halo (C2-C6) alkynyl”, “halo (C3-C6) cycloalkyl”, “halo (C1-C10) alkoxy”, “halo (C2-C6) alkenyloxy” and “halo (C2-C6) alkynyloxy”.

[0023] Examples of “halo (C1-C6) alkyl” include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trichloromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, heptafluoropropyl and heptafluoroisopropyl.

[0024] Examples of “halo (C3-C6) cycloalkyl” include 2-fluorocyclopropyl, 2-chlorocyclopropyl, 2-iodocyclopropyl, 1,2-difluorocyclopropyl, 2,2-difluorocyclopropyl, 2-chloro-3-fluorocyclopropyl and 1,2,2,3,3-pentachlorocyclopropyl.

[0025] Examples of “halo (C1-C6) alkoxy” include difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 2,2,3,3-tetrafluoropropoxy and 2,2,3,4,4,4-hexafluorobutoxy.

[0026] Examples of “halo(C1-C6)alkylthio” include fluoromethylthio, 2-fluoroethylthio, 3-fluoropropylthio, (2,2-difluoro-1-methylethyl)thio, and (2,2,2-trichloro-1-methylethyl)thio.

[0027] Examples of “halo(C1-C6)alkylsulfinyl” include fluoromethylsulfinyl, 2-fluoroethylsulfinyl, 3-fluoropropylsulfinyl, (2,2-difluoro-1-methylethyl) sulfinyl, and (2,2,2-trichloro-1-methylethyl) sulfinyl.

[0028] Examples of “halo(C1-C6)alkylsulfonyl” include fluoromethylsulfonyl, 2-fluoroethylsulfonyl, 3-fluoropropylsulfonyl, (2,2-difluoro-1-methylethyl) sulfonyl, and (2,2,2-trichloro-1-methylethyl) sulfonyl.

[0029] Examples of “halo(C2-C6)alkenyl” include 2-fluoroethenyl, 3-chloroallyl, 2,2-dichloro-1-methylethenyl, and 2,3,3-trichloro-1-methyl-2-propenyl.

[0030] “Halo(C2-C6)alkynyl” refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms, such as 3-chloro-2-propynyl, 3-chloro-1,1-dimethyl-2-propynyl, and the like.

[0031] “Cyano(C1-C6)alkyl” refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 3-cyanopropyl, 2-cyanopropyl, 1-cyanopropyl, 1-cyano-1-methylethyl, 2-cyanobutyl, 2-cyanohexyl, and the like.

[0032] “N-mono-(C1-C6)alkylamino” refers to an alkylamino group containing a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as N-methylamino, N-ethylamino, N-isopropylamino, and the like. “N-mono-(C2-C6)alkenylamino” refers to an alkenylamino group containing a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, such as N-ethenylamino, N-propenylamino, N-(1-methyl-2-propen-1-yl)amino, and the like. “N-mono-(C2-C6)alkynylamino” refers to an alkynylamino group containing a straight-chain or branched alkynyl group having 2 to 6 carbon atoms, such as N-ethynylamino, N-2-propynylamino, and the like.

[0033] "N-(C1-C6)alkyl-N-(C1-C6)alkylamino" refers to a dialkylamino having 2 to 12 carbon atoms, having a straight-chain or branched-chain alkyl group and having 1 to 6 carbon atoms, such as N,N-dimethylamino, N-ethyl-N-methylamino, etc. "N-(C2-C6)alkenyl-N-(C2-C6)alkenylamino" refers to a dialkenylamino having 4 to 12 carbon atoms, containing a straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms, such as N,N-divinylamino, N-vinyl-N-2-propenylamino, N-(2-methyl-1-propenyl)-N-2-propenylamino, etc. "N-(C2-C6)alkynyl-N-(C2-C6)alkynylamino" refers to a dialkynylamino having 5 to 13 carbon atoms, containing a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, such as N,N-diethynylamino, N-ethynyl-N-2-propynylamino, etc.

[0034] "N-mono-(C1-C6)alkylaminocarbonyl" refers to an alkylaminocarbonyl having 2 to 7 carbon atoms, containing a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, such as N-methylaminocarbonyl, N-ethylaminocarbonyl, N-n-propylaminocarbonyl, N-isopropylaminocarbonyl, N-n-butylaminocarbonyl, N-isobutylaminocarbonyl, N-sec-butylaminocarbonyl, N-tert-butylaminocarbonyl, N-n-pentylaminocarbonyl, N-isopentylaminocarbonyl, N-tert-pentylaminocarbonyl, N-neopentylaminocarbonyl, N-n-hexylaminocarbonyl, N-isohexylaminocarbonyl, etc.

[0035] "N-(C1-C6)alkyl-N-(C1-C6)alkylaminocarbonyl" refers to a dialkylaminocarbonyl having 3 to 13 carbon atoms, containing a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, such as N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di-n-propylaminocarbonyl, N,N-diisopropylaminocarbonyl, N,N-di-n-butylaminocarbonyl, N,N-di-sec-butylaminocarbonyl, N,N-di-tert-butylaminocarbonyl, N-methyl-N-ethylaminocarbonyl, N-methyl-N-n-propylaminocarbonyl, N-methyl-N-isopropylaminocarbonyl, N-methyl-N-n-butylaminocarbonyl, N-methyl-N-sec-butylaminocarbonyl, N-methyl-N-tert-butylaminocarbonyl, N-methyl-N-n-pentylaminocarbonyl, N-methyl-N-isopentylaminocarbonyl, N-methyl-N-tert-pentylaminocarbonyl, N-methyl-N-neopentylaminocarbonyl, N-methyl-N-(2,3-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-(1-methylbutyl)aminocarbonyl, N-methyl-N-n-hexylaminocarbonyl, N-methyl-N-isohexylaminocarbonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, etc.

[0036] “(C1-C6) alkylcarbonylamino” refers to an alkylcarbonylamino group having 2 to 7 carbon atoms, such as an alkylcarbonylamino group having the above-mentioned (C1-C6) alkyl, for example, acetylamino, N-propionylamino, N-butyrylamino, N-(2-methylpropionyl)amino, N-valerylamino, N-(2-methylbutyryl)amino, N-(3-methylbutyryl)amino, N-pivaloylamino, N-caproylamino, etc. “(C3-C6) cycloalkylcarbonylamino” refers to a cycloalkylcarbonylamino group having 4 to 7 carbon atoms, such as cyclopropylcarbonylamino, etc.

[0037] The expressions “(C1-C6)”, “(C1-C10)”, “(C2-C6)”, “(C3-C6)”, “(C3-C7)”, etc. each refer to the range of the number of carbon atoms in each group. The above definitions also apply to groups in which two or more of the above groups are linked together, and for example, “(C1-C6) alkoxy(C1-C6) alkyl” means a straight-chain or branched-chain alkoxy having 1 to 6 carbon atoms bonded to a straight-chain or branched-chain alkyl having 1 to 6 carbon atoms.

[0038] “Heterocyclic group” and “heterocycle” refer to a 5- or 6-membered monocyclic aromatic heterocyclic group, a 4- to 6-membered monocyclic non-aromatic heterocyclic group, etc., each containing carbon atoms and 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms as ring-constituting atoms.

[0039] Examples of “aromatic heterocyclic group” include monocyclic aromatic heterocyclic groups or fused polycyclic heterocyclic groups, such as furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl, indolyl, indazolyl, benzimidazolyl, azaindolyl, azaindazolyl, benzofuryl, benzothienyl, benzisoxazolyl, benzisothiazolyl, benzoxazolyl, benzothiazolyl, benzothiadiazolyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, quinazolinyl, cinnolinyl, naphthyridinyl, pyridopyrimidinyl, pyridopyrazinyl, benzopyranyl, benzoxazinyl, carbazolyl, dibenzofuryl, acridinyl, phenazinyl, phenothiazinyl, and phenoxathiinyl.

[0040] Examples of the "non-aromatic heterocyclic group" include monocyclic non-aromatic heterocyclic groups or fused polycyclic heterocyclic groups, such as oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneimino, oxazolidinyl, thiazolidinyl, imidazolidinyl, oxazolinyl, thiazolinyl, isoxazolinyl, imidazolinyl, dioxoleneyl, dioxolanyl, dihydrooxadiazolyl, 2-oxo-pyrrolidin-1-yl, 2-oxo-1,3-oxazolidin-5-yl, 5-oxo-1,2,4-oxadiazolin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-dioxepan-2-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxotetrahydrothiopyranyl, 1,1-dioxotetrahydrothiopyranyl, tetrahydrofuranyl, dioxanyl, pyrazolidinyl, pyrazolinyl, tetrahydropyrimidinyl, dihydrotriazolyl, tetrahydrotriazolyl, decahydroisoquinoline, quinuclidine, azatricyclo[3.3.1.13,7]decane, and 8-oxa-2-azaspiro[4.5]decane.

[0041] Examples of the "(C1-C12)alkylsilyl" include TMS (trimethylsilyl) group, TES (triethylsilyl) group, TBS (tert-butyldimethylsilyl) group, TIPS (triisopropylsilyl) group, and BIBS (di-tert-butylisobutylsilyl) group.

[0042] Examples of the "Z,Z(C1-C6)alkoxy" include benzhydryloxy, 1,1-diphenylethoxy, 1,2-diphenylethoxy, etc.

[0043] Examples of the "(C1-C6)alkoxy(C1-C6)alkoxy(C1-C6)alkoxy" include 2-methoxy-1-(methoxymethyl)ethoxy and ethoxymethoxymethoxy.

[0044] Examples of the salts of the amide compound represented by the general formula [I] of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and p-toluenesulfonate; and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium ion.

[0045] The amide compounds represented by the general formula [I] of the present invention and their salts may have one or more chiral centers in the structural formula and may exist as two or more optical isomers or diastereoisomers. All optical isomers and mixtures of isomers in any ratio are also included in the present invention. In addition, due to the presence of a carbon-carbon double bond in the structural formula, the amide compounds represented by the general formula [I] of the present invention and their salts may exist as two geometric isomers. All geometric isomers and mixtures of isomers in any ratio are also included in the present invention.

[0046] The amide compound represented by the general formula [I] of the present invention or its salt can be produced, for example, according to the production method described below as a non-limiting example. Production method 1.

[0047] wherein each symbol is as defined above.

[0048] The production method in step [a] In this reaction, the amide compound represented by the general formula [I] can be produced by reacting a carboxylic acid represented by the general formula [1] with an amine compound represented by the general formula [2] in the presence of a condensing agent, a base, and an inert solvent. Since this reaction is an equimolar reaction of the compounds, they are basically used in equimolar amounts, but either of them can be used in excess.

[0049] The condensing agent used in this reaction can be those commonly used in amide production, and examples thereof include trifluoroacetic anhydride, chloroformate, Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexylcarbodiimide), CDI (carbonyldiimidazole), and DEPC (diethyl cyanophosphonate). The amount of the condensing agent used can be appropriately selected from the range of equimolar to excess molar amounts relative to the carboxylic acid represented by the general formula [1].

[0050] The base used in this reaction can include inorganic or organic bases. Examples of the inorganic bases include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate. Examples of the organic bases include triethylamine, pyridine, DMAP, and DBU. The amount of the base used can be selected from the range of catalytic amount to excess molar amount relative to the carboxylic acid represented by the general formula [1].

[0051] The inert solvent used in this reaction can be any solvent that does not significantly hinder the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain ethers or cyclic ethers such as diethyl ether, dioxane, and tetrahydrofuran; amides such as dimethylformamide and dimethylacetamide; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, acetone, methyl ethyl ketone, etc. These inert solvents can be used alone or in combination of two or more kinds.

[0052] This reaction can also be carried out in an atmosphere of an inert gas such as nitrogen or argon. This reaction can be carried out in the range from room temperature to the boiling point of the inert solvent used. The reaction time varies depending on the reaction scale and reaction temperature, but can be in the range from several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction mixture by conventional methods. If necessary, recrystallization, column chromatography, etc. can be employed for purifying the target product. Production method 2.

[0053] Each symbol is as defined above. The production method in step [b] In this reaction, the amide compound represented by the general formula [I] can be produced by reacting the carboxylic acid chloride represented by the general formula [3] with the compound represented by the general formula [2] in the presence of a base and an inert solvent.

[0054] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; alkali metal hydrides such as sodium hydride and potassium hydride; acetates such as potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine, etc. The amount of the base used is usually in the range of 1 to 10 times the molar amount relative to the compound represented by the general formula [2].

[0055] The inert solvent that can be used in this reaction can be any solvent that does not significantly impede the progress of this reaction, and examples thereof include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; chain ethers or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aliphatic hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more.

[0056] This reaction can also be carried out under an atmosphere of an inert gas such as nitrogen or argon. This reaction can generally be carried out in the range from about 0 °C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., but can be appropriately selected from the range of several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction mixture by conventional methods. If necessary, recrystallization, column chromatography, etc. can be employed for purifying the target product. Alternatively, the separated product can proceed to the next step without purification. Production method 3.

[0057] Wherein Hal represents a halogen atom, and each of the other symbols is as defined above. The production method in step [c] In this reaction, the biaryl compound represented by the general formula [I]′ can be produced by reacting a halogenated benzene derivative represented by the general formula [4] with boric acid represented by the general formula [5] in the presence of a palladium catalyst.

[0058] This reaction can be carried out, for example, in an organic solvent (benzene, toluene, dimethylformamide, dioxane, tetrahydrofuran, acetonitrile, dimethoxyethane, acetone, etc.) in the presence of a base (sodium ethoxide, sodium hydroxide, potassium hydroxide, triethylamine, sodium carbonate, sodium bicarbonate, potassium carbonate, cesium carbonate, tripotassium phosphate, tetrabutylammonium fluoride, etc.) or an aqueous solution thereof, or a mixture thereof, and a catalyst (tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), bis(triphenylphosphine)palladium dichloride (PdCl2(PPh3)2), palladium acetate (Pd(OAc)2), palladium black, 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (PdCl2(dppf)2), 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (acetonitrile adduct) (PdCl2(dppf)2·MeCN), diallyl palladium dichloride (PdCl2(allyl)2), phenylbis(triphenylphosphine)palladium iodide (PhPdI(PPh3)2), etc.).

[0059] This reaction can also be carried out in an atmosphere of an inert gas such as nitrogen or argon. This reaction can be carried out in the range from room temperature to the boiling point of the inert solvent used. The reaction time varies depending on the reaction scale and reaction temperature, but can be in the range from several minutes to 48 hours. After the reaction is completed, the target product can be separated from the reaction mixture by conventional methods. If necessary, recrystallization, column chromatography, etc. can be used to purify the target product.

[0060] Specific examples of the compounds of the present invention are shown below. In the following tables (Table 1-1, Table 1-2, Table 2-1, Table 3-1, Table 4-1, Table 5-1, Table 6-1, Table 7-1, Table 8-1, Table 9-1, Table 10-1, Table 11-1, and Table 12-1), H represents a hydrogen atom, F represents fluorine, Cl represents a chlorine atom, and Br represents bromine. In these tables, the melting point (°C), refractive index nD (measurement temperature; °C) or NMR data are given as physical properties. The NMR data are shown in Appendix 1.

[0061] Examples of specific compounds represented by the following general formula [I-A] are shown in the following tables. In these tables, Py. represents a pyridyl group, Bn represents a benzyl group, MOM represents a methoxymethyl group, TMS represents a trimethylsilyl group, and Ac represents an acetyl group.

[0062]

[0063] [Table 1] · Table 1-1

[0064] [Table 2] · Table 1-1 (continued)

[0065] [Table 3] · Table 1-1 (continued)

[0066] [Table 4] · Table 1-1 (continued)

[0067] [Table 5] · Table 1-1 (continued)

[0068] [Table 6] · Table 1-1 (continued)

[0069] [Table 7] ·Table 1-1 (continued)

[0070] [Table 8] ·Table 1-1 (continued)

[0071] [Table 9] ·Table 1-1 (continued)

[0072] [Table 10] ·Table 1-1 (continued)

[0073] [Table 11] ·Table 1-1 (continued)

[0074] [Table 12] ·Table 1-1 (continued)

[0075] [Table 13] ·Table 1-1 (continued)

[0076] [Table 14] ·Table 1-1 (continued)

[0077] [Table 15] ·Table 1-1 (continued)

[0078] [Table 16] ·Table 1-1 (continued)

[0079] [Table 17] ·Table 1-1 (continued)

[0080] [Table 18] ·Table 1-1 (continued)

[0081] [Table 19] ·Table 1-1 (continued)

[0082] [Table 20] · Table 1-1 (continued)

[0083] [Table 21] · Table 1-1 (continued)

[0084] [Table 22] · Table 1-1 (continued)

[0085] [Table 23] · Table 1-1 (continued)

[0086] [Table 24] · Table 1-1 (continued)

[0087] [Table 25] · Table 1-1 (continued)

[0088] [Table 26] · Table 1-1 (continued)

[0089] [Table 27] · Table 1-1 (continued)

[0090] [Table 28] · Table 1-1 (continued)

[0091] [Table 29] · Table 1-1 (continued)

[0092] [Table 30] · Table 1-1 (continued)

[0093] [Table 31] · Table 1-1 (continued)

[0094] [Table 32] · Table 1-1 (continued)

[0095] [Table 33] · Table 1-1 (continued)

[0096] [Table 34] · Table 1-1 (continued)

[0097] [Table 35] · Table 1-1 (continued)

[0098] [Table 36] · Table 1-1 (continued)

[0099] [Table 37] · Table 1-1 (continued)

[0100] [Table 38] · Table 1-1 (continued)

[0101] [Table 39] · Table 1-1 (continued)

[0102] [Table 40] · Table 1-1 (continued)

[0103] [Table 41] · Table 1-1 (continued)

[0104] [Table 42] · Table 1-1 (continued)

[0105] [Table 43] · Table 1-1 (continued)

[0106] [Table 44] · Table 1-1 (continued)

[0107] [Table 45] · Table 1-1 (continued)

[0108] [Table 46] ·Table 1-1 (continued)

[0109] [Table 47] ·Table 1-1 (continued)

[0110] [Table 48] ·Table 1-1 (continued)

[0111] [Table 49] ·Table 1-1 (continued)

[0112] [Table 50] ·Table 1-1 (continued)

[0113] [Table 51] ·Table 1-1 (continued)

[0114] [Table 52] ·Table 1-1 (continued)

[0115] [Table 53] ·Table 1-1 (continued)

[0116] [Table 54] ·Table 1-1 (continued)

[0117] [Table 55] ·Table 1-1 (continued)

[0118] [Table 56] ·Table 1-1 (continued)

[0119] [Table 57] ·Table 1-1 (continued)

[0120] [Table 58] ·Table 1-1 (continued)

[0121] [Table 59] ·Table 1-1 (continued)

[0122] [Table 60] ·Table 1-1 (continued)

[0123] [Table 61] ·Table 1-2

[0124] [Table 62] ·Table 1-2 (continued)

[0125] [Table 63] ·Table 1-2 (continued)

[0126] [Table 64] ·Table 1-2 (continued)

[0127] [Table 65] ·Table 1-2 (continued)

[0128] [Table 66] ·Table 1-2 (continued)

[0129] [Table 67] ·Table 1-2 (continued)

[0130] [Table 68] ·Table 1-2 (continued)

[0131] [Table 69] ·Table 1-2 (continued)

[0132] [Table 70] ·Table 1-2 (continued)

[0133] Examples of specific compounds represented by the following general formula [I-B] are shown in the table below.

[0134]

[0135] In the above formula [I-B], R 2 and R 3 each represent a chlorine atom.

[0136] [Table 71] · Table 2-1

[0137] Examples of specific compounds represented by the following general formula [I-C] are shown in the table below.

[0138]

[0139] In the above formula [I-C], R 2 and R 3 each represent a chlorine atom.

[0140] [Table 72] · Table 3-1

[0141] [Table 73] · Table 3-1 (continued)

[0142] Examples of specific compounds represented by the following general formula [I-D] are shown in the table below.

[0143]

[0144] In the above formula [I-D], R 2 and R 3 each represent a chlorine atom.

[0145] [Table 74] · Table 4-1

[0146] Examples of specific compounds represented by the following general formula [I-E] are shown in the table below.

[0147]

[0148] In the above formula [I-E], R 2 and R 3 each represent a chlorine atom.

[0149] [Table 75] · Table 5-

[0150] Examples of specific compounds represented by the following general formula [I-F] are shown in the table below.

[0151]

[0152] In the above formula [I-F], R 2 and R 3 each represent a chlorine atom.

[0153] [Table 76] · Table 6-1

[0154] Examples of specific compounds represented by the following general formula [I-G] are shown in the table below.

[0155]

[0156] In the above formula [I-G], R 2 and R 3 each represent a chlorine atom.

[0157] [Table 77] · Table 7-1

[0158] Examples of specific compounds represented by the following general formula [I-H] are shown in the table below.

[0159]

[0160] In the above formula [I-H], R 2 and R 3 each represent a chlorine atom.

[0161] [Table 78] · Table 8-1

[0162] Examples of specific compounds represented by the following general formula [I-I] are shown in the table below.

[0163]

[0164] In the above formula [I-I], R 2 and R 3 each represent a chlorine atom.

[0165] [Table 79] · Table 9-1

[0166] Examples of specific compounds represented by the following general formula [I-J] are shown in the table below.

[0167]

[0168] In the above formula [I-J], R 2 and R 3 each represent a chlorine atom.

[0169] [Table 80] · Table 10-1

[0170] Examples of specific compounds represented by the following general formula [I-K] are shown in the table below.

[0171]

[0172] In the above formula [I-K], R 2 and R 3 each represent a chlorine atom.

[0173] [Table 81] · Table 11-1

[0174] [Table 82] · Table 11-1 (continued)

[0175] [Table 83] · Table 11-1 (continued)

[0176] [Table 84] · Table 11-1 (continued)

[0177] Examples of specific compounds represented by the following general formula [I-L] are shown in the table below.

[0178]

[0179] In the above formula [I-L], R 2 and R 3 each represent a chlorine atom.

[0180] [Table 85] · Table 12-1

[0181] [Table 86] · Appendix 1

[0182] [Table 87] (Continued) of Appendix 1

[0183] The agricultural and horticultural fungicides containing the amide compound represented by the general formula [I] of the present invention or a salt thereof as an active ingredient are suitable for controlling diseases that may infect cereals, fruit trees, vegetables, other crops, and ornamental flowers.

[0184] Target diseases include filamentous fungal diseases, bacterial diseases, and viral diseases. Examples of filamentous fungal diseases include diseases caused by Deuteromycetes, which include Botrytis, Helminthosporium, Fusarium, Septoria, Cercospora, Pseudocercosporella, Rhynchosporium, Pyricularia, and Alternaria; diseases caused by Basidiomycetes, which include Hemilelia, Rhizoctonia, Ustilago, Typhula, and Puccinia; diseases caused by Ascomycota, which include Venturia, Podosphaera, Leptosphaeria, Blumeria, Erysiphe, Microdochium, Sclerotinia, Gaeumannomyces, Monilinia, and Uncinula; and diseases caused by other fungi, which include Ascochyta, Phoma, Pythium, Corticium, and Pyrenophora. Examples of bacterial diseases include diseases caused by Pseudomonas, Xanthomonas, and Erwinia. Examples of viral diseases include diseases caused by tobacco mosaic virus and the like.

[0185] Specific examples of filamentous fungal diseases include rice blast (Pyricularia oryzae), sheath blight of rice (Rhizoctonia solani), brown spot of rice (Cochiobolus miyabeanus), rice seedling blight (Rhizopus chinensis, Pythium graminicola, Fusarium graminicola, Fusarium roseum, species of Mucor, species of Phoma, species of Tricoderma), bakanae disease of rice (Gibberella fujikuroi), powdery mildew of barley, wheat, etc. (Blumeria graminis), powdery mildew of cucumber, etc. (Sphaerotheca fuliginea), powdery mildew of eggplant, etc. (Erysiphe cichoracearum), powdery mildew of other host plants, eyespot of barley, wheat, etc. (Pseudocercosporella herpotrichoides), smut of wheat, etc. (Urocystis tritici), snow blight of barley, wheat, etc. (Microdochium nivalis, Pythium iwayamai, Typhla ishikariensis, Typhla incarnata, Sclerotinia borealis), head blight of barley, wheat, etc. (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivalis), rust of barley, wheat, etc. (Puccinia recondita, Puccinia striiformis, Puccinia graminis), damping-off of barley, wheat, etc. (Gaeumannomyces graminis), crown rust of oats (Puccinia coronata), rust of other plants, gray mold of cucumber, strawberry, etc. (Botrytis cinerea), sclerotinia of cucumber, tomato, etc. (Sclerotinia sclerotiorum),Late blight of potato, tomato, etc. (Phytophthora infestans), late blight of other plants, downy mildew of various plants, such as downy mildew of cucumber (Pseudoperonospora cubensis) and downy mildew of grape (Plasmopara viticola), apple scab (Venturia inaequalis), apple blotch leaf spot (Alternaria mali), apple ring rot (Botryosphaeria berengeriana), grape late rot (Colletotrichum gloeosporioides, Colletotrichum acutatum), grape anthracnose (Elsinoe ampelina), pear black spot (Alternaria kikuchiana), citrus black spot (Diaporthe citri), citrus scab (Elsinoe fawcetti), cucumber anthracnose (Colletotrichum lagenarium), beet leaf spot (Cercospora beticola), peanut brown leaf spot (Cercospora arachidicola), peanut late leaf spot (Cercospora personata), wheat leaf blotch (Septoria tritici), wheat glume blotch (Leptosphaeria nodorum), barley net blotch (Pyrenophora teres), barley stripe (Pyrenophora graminea), barley leaf stripe (Rhynchosporium secalis), wheat loose smut (Ustilago nuda), wheat bunt (Tilletia caries), lawn brown patch (Rhizoctonia solani), lawn dollar spot (Sclerotinia homoeocarpa), Chinese cabbage Alternaria leaf spot (Alternaria brassicola), tomato late blight (Phytophthora infestans), cucumber gray mold (Botrytis cinerea), barley powdery mildew (Blumeria graminis f.sp. Hordei),Sudden death syndrome of soybean (Fusarium virguliforme) and sclerotinia of cruciferous crops (Sclerotinia sclerotirum).

[0186] Specific examples of bacterial diseases include diseases caused by species of the genus Pseudomonas, such as bacterial leaf spot of cucumber (Pseudomonas syringae pv. Lachrymans), bacterial wilt of tomato (Pseudomonas syringae pv. Lachrymans), and bacterial grain rot of rice (Pseudomonas glumae); diseases caused by species of the genus Xanthomonas, such as black rot of cabbage (Xanthomonas campestris), bacterial leaf streak of rice (Xanthomonas oryzae), and citrus canker (Xanthomonas citri); and diseases caused by species of the genus Erwinia, such as soft rot of cabbage (Erwinia carotovora).

[0187] Specific examples of viral diseases include tobacco mosaic disease (tobacco mosaic virus).

[0188] In particular, the agricultural and horticultural fungicides containing the amide compound represented by the general formula [I] or a salt thereof according to the present invention as an active ingredient can be highly effective against filamentous fungal diseases, especially Alternaria leaf spot of Chinese cabbage (Alternaria brassicicola), late blight of tomato (Phytophthora infestans), gray mold of cucumber (Botrytis cinerea), anthracnose of cucumber (Colletotrichum orbiculare), rice blast (Magnaporthe oryzae), apple scab (Venturia inaequalis), powdery mildew of barley (Blumeria graminis f. sp. Hordei), leaf blight of wheat (Septoria tritici), sclerotinia of cucumber (Sclerotinia sclerotiorum), ring rot of apple (Botryosphaeria berengeriana), late rot of grape (Colletotrichum gloeosporioides, Colletotrichum acutatum), sudden death syndrome of soybean (Fusarium virguliforme), head blight of barley, wheat, etc. (Fusarium graminearum), sclerotinia of cruciferous crops (Sclerotinia sclerotiorum), and brown spot of rice (Cochliobolus miyabeanus).

[0189] The agricultural and horticultural fungicide containing the amide compound represented by the general formula [I] of the present invention or a salt thereof as an active ingredient can be used as an insecticide as well as a fungicide. The agricultural and horticultural fungicide can be used alone, or in combination with other agricultural chemicals or as a mixture with other agricultural chemicals to control pests that may damage rice, fruit trees, vegetables, other crops and ornamental flowers, including forestry and agricultural pests, horticultural pests, stored grain pests, sanitary pests, nematodes, etc. Specific examples of pests, nematodes, etc. include the following: species of the order Lepidoptera, such as Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, Hyphantria cunea, Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfurana, Parnara guttata, Marasmia exigua, Parnara guttata, Sesamia inferens, Brachmia triannulella, Monema flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera, Phalerodonta manleyi, Eumeta japonica, Malacosoma neustria testacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archips xylosteanus, Agrotis segetum, Tetramoera schistaceana, Papilio machaonHippocrates, Endoclyta sinensis, Lyonetia prunifoliella, Phyllonorycter ringoneella, Cydia kurokoi, Eucoenogenes aestuosa, Lobesia botrana, Latoia sinica, Euzophera batangensis, Phalonidia mesotypa, Spilosoma imparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella, Endoclyta exrescens, Nemapogon granellus, Synanthedon hector, Cydia pomonella, Plutella xylostella, Cnaphalocrocis medinalis, Sesamia calamistis, Scirpophaga incertulas, Pediasia teterrellus, Phthorimaea operculella, Stauropus fagi persimilis, Etiella zinckenella, Spodoptera exigua, Palpifer sexnotata, Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angerona prunaria, Clostera anastomosis, Pseudoplusia includens, Matsumuraeses falcana, Helicoverpaassulta), black-spotted cutworm (Autographa nigrisigna), black cutworm (Agrotis ipsilon), tea tussock moth (Euproctis pseudoconspersa), citrus leafroller (Adoxophyes orana), tea leafminer (Caloptilia theivora), tea long-horned leafroller (Homonana magnanima), tobacco moth (Ephestia elutella), tea bagworm (Eumeta minuscula), poplar leafminer (Clostera anachoreta), flax looper (Heliothis maritima), grape long-horned leafroller (Sparganothis pilleriana), African armyworm (Busseola fusca), oriental tussock moth (Euproctis subflava), brown-striped geometer (Biston robustum), corn earworm (Heliothis zea), sweet potato armyworm (Aedia leucomelas), pear slug caterpillar (Narosoideus flavidorsalis), pear dagger moth (Viminia rumicis), pear angle-folded moth (Bucculatrix pyrivorella), oriental fruit moth (Grapholita molesta), pear leafminer (Spulerina astaurota), fruit external pith borer (Ectomyelois pyrivorella), striped rice borer (Chilo suppressalis), onion leafminer (Acrolepiopsis sapporensis), Indianmeal moth (Plodia interpunctella), diamondback moth (Hellula undalis), angoumois grain moth (Sitotroga cerealella), common cutworm (Spodoptera litura), mung bean shoot moth (Eucosma aporema), strawberry long-winged leafroller (Acleris comariana), grey-toothed slug caterpillar (Scopelodes contractus), gypsy moth (Orgyia thyellina), fall armyworm (Spodoptera frugiperda), Ostrinia zaguliaevi, twin-spotted moth (Naranga aenescens), tea tussock moth (Andraca bipunctata), grapevine clearwing moth (Paranthreneregalis), Acosmeryx Castanea, Phyllocnistis toparcha, Endopiza viteana, Eupoecillia ambiguella, Anticarsia gemmatalis, Cnephasiacinereipalpana, Lymantria dispar, Dendrolimus spectabilis, Leguminivora glycinivorella, Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodes indicata, Archipsfuscocupreanus, Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethes punctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus, Colias erate poliographus, Phalera flavescens, Pieris brassicae and Pieris rapae crucivora of Pieridae, Euproctis similis, Acrolepiopsis suzukiella, Ostrinianubilalis, Mamestra brassicae, Ascotis selenaria, Phtheochroides clandestina, Hoshinoa adumbratana, Odonestis pruni japonensis, Triaena intermedia, Adoxophyes Oranafasciata), Grapholita inopinata, Spilonota ocellana, Spilonota lechriaspis, Illiberis pruni, Argyresthia conjugella, Caloptilia zachrysa, Archips breviplicanus, Anomis flava, Pectinophora gossypiella, Notarcha derogata, Diaphania indica, Heliothis virescens, and Earias cupreoviridis;

[0190] Species of the order Hemiptera, such as Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Aeschynteles maculatus, Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissus leucopterus, Icerya purchasi, Piezodorus hybneri, Lagynotomus elongatus, Thaia subrufa, Scotinophara lurida, Sitobion ibarae, Stariodes iwasakii, Aspidiotus destructor, Taylorilygus pallidulus, Myzus mumecola, Pseudaulacaspis prunicola, Acyrthosiphon pisum, Anacanthocoris striicornis, Ectometopterus micantulus, Eysarcoris lewisi, Molipteryx fuliginosa, Cicadella viridis, Rhopalosiphum rufiabdominalis, Saissetia oleae, Trialeurodes vaporariorum, Aguriahana quercus, Lygus spp., Euceraphis punctipennis, Andaspis kashicola, Coccuspseudomagnoliarum), Cavelerius saccharivorus, Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae, Leptocorisachinensis, Trioza quercicola, Uhlerites latius, Erythroneura comes, Paromius exiguus, Duplaspidiotusclaviger, Nephotettix nigropictus, Halticiellusinsularis, Perkinsiella saccharicida, Psyllamalivorella, Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspis pentagona, Pulvinaria kuwacola, Apolyguslucorum, Togo hemipterus, Toxoptera aurantii, Saccharicoccus sacchari, Geoica lucifuga, Numata muiri, Comstockaspis perniciosa, Unaspis citri, Aulacorthum solani, Eysarcoris ventralis, Bemisiaargentifolii, Cicadella spectra, Aspidiotus hederae, Liorhyssus hyalinus, Calophyanigridorsalis), white-backed planthopper (Sogatella furcifera), bean aphid (Megoura crassicauda), cabbage aphid (Brevicoryne brassicae), soybean aphid (Aphis glycines), rice stink bug (Leptocorisa oratorius), green rice leafhopper (Nephotettix virescens), lettuce aphid (Uroleucon formosanum), tobacco plant bug (Cyrtopeltis tennuis), silverleaf whitefly (Bemisia tabaci), peach scale (Lecanium persicae), tea scale (Parlatoria theae), peony scale (Pseudaonidia paeoniae), small green leafhopper (Empoasca onukii), brown-winged stink bug (Plautia stali), tulip aphid (Dysaphis tulipae), euphorbia aphid (Macrosiphum euphorbiae), azalea lace bug (Stephanitis pyrioides), horned wax scale (Ceroplastes ceriferus), camellia scale (Parlatoria camelliae), Spinola's plant bug (Apolygus spinolai), black-tailed leafhopper (Nephotettix cincticeps), green stink bug (Glaucias subpunctatus), variegated plant bug (Orthotylus flavosparsus), corn leaf aphid (Rhopalosiphum maidis), corn planthopper (Peregrinus maidis), two-spotted stink bug (Eysarcoris parvus), common bed bug (Cimex lectularius), fir psyllid (Psylla abieti), brown planthopper (Nilaparvata lugens), pittosporum psyllid (Psylla tobirae), wrinkled vegetable bug (Eurydema rugosum), pear aphid (Schizaphis piricola), pear psyllid (Psylla pyricola), pear scale (Parlatoreopsis pyri), pear lace bug (Stephanitis nashi), pineapple mealybug (Dysmicoccus wistariae), pear scale (Lepholeucaspis japonica), pear-tail aphid (Sappaphis piri), turnip aphid (Lipaphiserysimi), Neotoxoptera formosana, Rhopalosophum nymphaeae, Edwardsiana rosae, Pinnaspis aspidistrae, Psylla alni, Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoriaziziphi, Uhlerites debile, Laodelphax striatella, Eurydema pulchrum, Cletus trigonus, Cloviapunctata, Empoasca sp., Coccus hesperidum, Pachybrachius luridus, Planococcus kraunhiae, Stenotusbinotatus, Arboridia apicalis, Macrosteles fascifrons, Dolycoris baccarum, Adelphocoris triannulatus, Viteus vitifolii, Acanthocoris sordidus, Leptocorisaacuta, Macropes obnubilus, Cletus punctiger, Riptortus clavatus, Paratrioza cockerelli, Aphrophora costalis, Lygus disponsi, Lygus saundersi, Crisicoccus pini, Empoascaabietis), Matsucoccus matsumotoi, Aphis craccivora, Megacopta punctatissimum, Eysarcoris guttiger, Lepidosaphes beckii, Diaphorina citri, Toxoptera citricidus, Planococcus citri, Dialeurodes citri, Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri, Pulvinaria citricola, Coccus discrepans, Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum, Rhopalosiphum padi, Sitobion akebiae, Schizaphis graminum, Sorhoanus tritici, Brachycaudus helichrysi, Carpocoris purpureipennis, Myzus persicae, Hyalopterus pruni, Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spiraecola, Aphis pomi, Lepidosaphes ulmi, Psylla mali, Heterocordylus flavipes, Myzus malisuctus, Aphidonuguis mali, Orientus ishidai, Ovatusmalicolens), Eriosoma lanigerum, Ceroplastes rubens, and Aphis gossypii;

[0191] Species of the order Coleoptera, such as Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, Hypera postica, Echinocnemus squameus, Oulema oryzae, Donacia provosti, Lissorhoptrus oryzophilus, Colasposoma dauricum, Euscepes postfasciatus, Epilachna varivestis, Acanthoscelides obtectus, Diabrotica virgifera virgifera, Involvulus cupreus, Aulacophora femoralis, Bruchus pisorum, Epilachna vigintioctomaculata, Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phyllotreta striolata, Psacothea hilaris, Aeolesthes chrysothrix, Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, species of the genus Diabrotica spp.) Mimela splendens, Sitophilus zeamais, Tribolium castaneum, Sitophilus oryzae, Palorus subdepressus, Melolontha japonica, Anoplophora malasiaca, Neatus picipes, Leptinotarsa decemlineata, Diabrotica undecimpunctata howardi, Sphenophorus venatus, Crioceris quatuordecimpunctata, Conotrachelus nenuphar, Ceuthorhynchidius albosuturalis, Phaedon brassicae, Lasioderma serricorne, Sitona japonicus, Adoretus tenuimaculatus, Tenebrio molitor, Basilepta balyi, Hypera nigrirostris, Chaetocnema coninna, Anomala cuprea, Heptophylla Picea, Epilachna vigintioctopunctata, Diabrotica longicornis, Eucetonia pilifera, Agriotes spp.) Attagenus unicolor japonicus, Pagria signata, Anomala rufocuprea, Palorus ratzeburgii, Alphitobius laevigatus, Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus, Popillia japonica, Epicauta gorhami, Sitophilus zeamais, Rhynchites heros, Listroderes costirostris, Callosobruchus maculatus, Phyllobius armatus, Anthonomus pomorum, Linaeidea Aenea, and Anthonomus grandis;.

[0192] Species of the order Diptera, such as Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhacochlaena japonica, Muscina stabulans, species of the family Phoridae such as Megaselia spiracularis, Clogmia albipunctata, Tipula aino, Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis, Hylemya brassicae, Asphondylia sp.)、Delia platura, Delia antiqua, Rhagoletis cerasi, Culex pipiens molestus Forskal, Ceratitis capitata, Bradysia agrestis, Pegomyacunicularia, Liriomyza sativae, Liriomyza bryoniae, Chromatomyia horticola, Liriomyza chinensis, Culexquinquefasciatus, Aedes aegypti, Aedes albopictus, Liriomyza trifolii, Liriomyza sativae, Dacusdorsalis, Dacus tsuneonis, Sitodiplosis mosellana, Meromuza nigriventris, Anastrepha ludens, and Rhagoletis pomonella;.

[0193] Species of the order Hymenoptera, such as Pristomyrmex pungens, species of the family Bethylidae, Monomorium pharaonis, Pheidolenoda, Athalia rosae, Dryocosmus kuriphilus, Formicafusca japonica, Vespinae spp. (wasps), Athaliainfumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge mali, and Ochetellus glaber;

[0194] Species of the order Orthoptera, such as Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica, Homorocoryphus jezoensis, and Teleogryllus emma;

[0195] Species of the order Thysanoptera, such as Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, Anaphothrips obscurus, Liothrips floridensis, Thrips simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, Pseudodendrothrips mori, Microcephalothrips abdominalis, Leeuwenia pasanii, Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Scirtothrips dorsalis, Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrips alliorum, Thrips hawaiiensis, Haplothrips kurdjumovi, Chirothrips manicatus, Frankliniella intonsa, Thrips coloratus, Franklinella occidentalis, Thrips palmi, Frankliniella lilivora, and Liothrips vaneeckei;

[0196] Species of the order Acari, such as Tetranychus truncatus, Tetranychus viennensis, Tetranychus kanzawai, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Tetranychus urticae, Eriophyeschibaensis, Brevipalpus spp., Tyrophagus similis, Panonychus citri, Brevipalpus phoenicis, Phyllocoptruta citri, Aculus schlechtendali, Panonychus ulmi, Rhyzoglyphus robini, and Sancassaniaspp.;

[0197] Species of the order Isoptera, such as Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., Reticulitermes flaviceps amamianus, Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odontotermes formosanus, Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus;

[0198] Species of the order Blattodea, such as Periplaneta fuliginosa, Blattella germanica, Blatta orientalis, Periplanetabrunnea, Blattella lituricollis, Periplaneta japonica, and Periplaneta americana;

[0199] Species of the phylum Nematoda, such as Nothotylenchus acris, Aphelenchoides besseyi, Pratylenchus penetrans, Meloidogyne hapla, Meloidogyne incognita, Globodera rostochiensis, Meloidogyne javanica, Heterodera glycines, Pratylenchus coffeae, Pratylenchus neglectus, and Tylenchus semipenetrans; and

[0200] Species of the phylum Mollusca, such as Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana.

[0201] In addition, the agricultural and horticultural fungicides of the present invention also have a strong insecticidal effect on Tuta absoluta.

[0202] The agricultural and horticultural fungicides containing the amide compound represented by the general formula [I] or a salt thereof according to the present invention as an active ingredient have a remarkable control effect on the above-mentioned diseases that damage paddy field crops, upland field crops, fruit trees, vegetables, other crops, ornamental flowers, etc. When the agricultural and horticultural fungicides are applied to nursery facilities, paddy fields, upland fields, fruit trees, vegetables, other crops, ornamental flowers, etc., and their seeds, paddy field water, stems and leaves, cultivation media (such as soil), etc. around the expected time of disease infection, that is, before infection or after confirmation of infection, the desired effect can be obtained. In addition, the application of the agricultural and horticultural fungicides utilizes so-called penetration and systemic conduction. That is, the nursery soil, the soil in the planting pit at the time of transplantation, the roots of plant strains, irrigation water, the cultivation water in hydroponics, etc. are treated with the agricultural and horticultural fungicides to allow crops, ornamental flowers, etc. to absorb the compounds of the present invention through the soil or in other ways through the roots.

[0203] Useful plants to which the agricultural and horticultural fungicides of the present invention can be applied include, but are not particularly limited to, for example, cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (e.g., soybeans, adzuki beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (e.g., apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy and fruit vegetables (e.g., cabbages, tomatoes, spinach, broccoli, lettuce, onions, scallions (ramsons and welsh onions), green peppers, eggplants, strawberries, pepper crops, okra, leeks, etc.), root vegetables (e.g., carrots, potatoes, sweet potatoes, taros, Japanese radishes, turnips, lotus roots, burdocks, garlic, Chinese chives, etc.), crops for processing (e.g., cotton, hemp, sugar beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), melons (e.g., Japanese pumpkins, cucumbers, watermelons, muskmelons, honeydews, etc.), forage grasses (e.g., cocksfoot, sorghum, timothy grass, clovers, alfalfa, etc.), turfgrasses (e.g., Korean lawn grass, bentgrass, etc.), spice and aromatic crops and ornamental crops (e.g., lavender, rosemary, thyme, parsley, pepper, ginger, etc.), ornamental flowers (e.g., chrysanthemums, roses, carnations, orchids, tulips, lilies, etc.), garden trees (e.g., ginkgo trees, cherry trees, Japanese aucuba, etc.) and forest trees (e.g., Abies sachalinensis, Picea jezoensis, pine, cypress, fir, hinoki cypress, eucalyptus, etc.).

[0204] The above-mentioned "plants" also include plants provided with herbicide tolerance by classical breeding techniques or genetic recombination techniques. Examples of such herbicide tolerance include tolerance to the following: HPPD inhibitors such as isoxaflutole; ALS inhibitors such as imazethapyr and thifensulfuron-methyl; EPSP synthase inhibitors such as glyphosate; glutamine synthetase inhibitors such as glufosinate; acetyl-CoA carboxylase inhibitors such as sethoxydim; or other herbicides such as bromoxynil, dicamba and 2,4-D.

[0205] Examples of plants provided with herbicide tolerance by classical breeding techniques include varieties of rapeseed, wheat, sunflower and rice that are tolerant to imidazolinones (such as imazethapyr) of ALS-inhibiting herbicides, and such rice is sold under the trade name Clearfield (registered trademark). Also included are various soybeans provided with tolerance to sulfonylureas (such as thifensulfuron-methyl) of ALS-inhibiting herbicides by classical breeding techniques, and they are sold under the trade name STS soybeans. Also included are plants provided with tolerance to acetyl-CoA carboxylase inhibitors (such as trione oxime herbicides and aryloxyphenoxypropionate herbicides) by classical breeding techniques, such as SR corn, etc. Plants having tolerance to acetyl-CoA carboxylase inhibitors are described in Proc. Natl. Acad. Sci. USA, 87, 7175-7179 (1990), etc. In addition, acetyl-CoA carboxylase mutants resistant to acetyl-CoA carboxylase inhibitors are reported in Weed Science, 53, 728-746 (2005), etc., and plants tolerant to acetyl-CoA carboxylase inhibitors can be engineered by introducing the gene of the acetyl-CoA carboxylase mutant into plants via genetic recombination techniques, or by introducing a resistance-conferring mutation into the acetyl-CoA carboxylase of plants. Alternatively, plants tolerant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc. can be engineered by introducing a nucleic acid that causes a base substitution mutation into plant cells (a typical example of this technique is the chimeric repair technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285:316-318)) to allow site-specific substitution mutations in the amino acids encoded by the acetyl-CoA carboxylase gene, ALS gene, etc. of plants. The agricultural and horticultural fungicides of the present invention can also be applied to these plants.

[0206] In addition, exemplary toxins expressed in genetically modified plants include insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; δ-endotoxins from Bacillus thuringiensis, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, and Cry9C, and other insecticidal proteins, such as VIP1, VIP2, VIP3, and VIP3A; insecticidal proteins from nematodes; toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins, and insect-specific neurotoxins; toxins of filamentous fungi; plant lectins; lectins; protease inhibitors, such as trypsin inhibitors, serine protease inhibitors, potato tuber-specific proteins, cysteine protease inhibitors, and papain inhibitors; ribosome-inactivating proteins (RIPs), such as ricin, maize RIP, abrin, luffin, saporin, and bryodin; steroid metabolic enzymes, such as 3-hydroxy steroid oxidase, ecdysteroid-uridine diphosphate-glucosyltransferase, and cholesterol oxidase; ecdysteroid inhibitors; HMG-CoA reductase; ion channel blockers, such as sodium channel blockers and calcium channel blockers; juvenile hormone esterase; diuretic hormone receptors; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0207] It also includes hybrid toxins, partially deleted toxins, and modified toxins derived from the following: δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, and Cry35Ab, and other insecticidal proteins such as VIP1, VIP2, VIP3, and VIP3A. Hybrid toxins can be produced by using recombinant techniques to combine domains derived from these proteins in a manner different from the original combinations found in nature. As a partially deleted toxin, the Cry1Ab toxin with a part of its amino acid sequence deleted is known. Among the modified toxins, one or more amino acids of the naturally occurring toxin are replaced. Examples of the aforementioned toxins and genetically modified plants capable of synthesizing these toxins are described in EP-A-0 374753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878, WO 03 / 052073, etc.

[0208] Since such genetically modified plants contain toxins, these plants exhibit resistance to pests, particularly coleopteran insect pests, hemipteran insect pests, dipteran insect pests, lepidopteran insect pests, and nematodes. The above-mentioned techniques and the agricultural and horticultural fungicides of the present invention can be used in combination or systematically.

[0209] To control various diseases, the agricultural and horticultural fungicides of the present invention are applied in an amount effective to control diseases to plants potentially infected with diseases, with or without being appropriately diluted or suspended in water, etc. For example, to control diseases that may infect crop plants such as fruit trees, cereals, and vegetables, foliar application and seed treatment such as dipping, powder coating, and calcium peroxide coating can be carried out. In addition, treatment of soil, etc. can also be carried out to allow plants to absorb agricultural chemicals through their roots. Examples of such treatments include whole soil incorporation, planting furrow treatment, seedbed soil incorporation, plug seedling treatment, planting pit treatment, plant root treatment, top dressing, rice nursery box treatment, and water surface application. In addition, application to the cultivation medium in hydroponics, fumigation treatment, trunk injection, etc. can also be carried out. In addition, the agricultural and horticultural fungicides of the present invention can be applied in an amount effective to control diseases to parts potentially infected with plant diseases, with or without being appropriately diluted or suspended in water, etc. For example, it can be directly applied to stored grain pests, household pests, hygiene pests, forest pests, etc., and is also used for coating residential building materials, for fumigation treatment, or as a bait. Furthermore, the agricultural and horticultural fungicides of the present invention can be applied, with or without being appropriately diluted or suspended in water, etc., in an amount effective for controlling diseases, to potentially disease-infected sites.

[0210] Exemplary methods of seed treatment include immersing seeds in a fluid of a diluted or undiluted liquid or solid formulation for permeating agrochemicals into the seeds; mixing seeds with a solid or liquid formulation or dust-coating the seeds with a solid or liquid formulation to attach the formulation to the seed surface; coating the seeds with a mixture of a solid or liquid formulation and an adhering carrier (such as resins and polymers); and applying a solid or liquid formulation near the seeds at the time of sowing. The term "seed" in the above seed treatment refers to a plant body in the initial stage of cultivation and used for plant propagation. In addition to the so-called seeds, examples also include plant bodies for vegetative propagation, such as bulbs, tubers, seed potatoes, bulbils, bulbels, corms, and cuttings. The term "soil" or "cultivation medium" in the method for using the agricultural and horticultural fungicides of the present invention refers to a support matrix for cultivating crops, particularly a support matrix that allows crop plants to extend their roots therein, and the material is not particularly limited as long as it allows plant growth. Examples of the support matrix include the so-called soil, seedling mats, and water, and specific examples of the material include sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, high molecular weight substances, rock wool, glass wool, wood chips, and bark.

[0211] Exemplary methods of applying to the crop foliage include applying a liquid formulation such as an emulsifiable concentrate and a suspending agent, or a solid formulation such as a wettable powder and a water-dispersible granule, after appropriate dilution in water; dust application; and fumigation. Exemplary methods of soil application include applying a water-diluted or undiluted liquid formulation to the roots of plants, seedling beds for raising seedlings, etc.; applying granules to the roots of plants, seedling beds for raising seedlings, etc.; before sowing or transplanting, applying a powder, a wettable powder, a water-dispersible granule, a granule, etc. to the soil, and then mixing the formulation into the whole soil; applying a powder, a wettable powder, a water-dispersible granule, a granule, etc. to the planting pit before sowing or planting; and applying a powder, a wettable powder, a water-dispersible granule, a granule, etc. to the planting furrow, etc.

[0212] For example, a powder, a water-dispersible granule, a granule, etc. can be applied to a rice seedling box. Although suitable formulations may vary depending on the timing of application, in other words, depending on cultivation stages such as sowing time, greening period, and transplanting period. Formulations such as powders, water-dispersible granules, granules, etc. can be mixed with the seedling soil. For example, such formulations are mixed into the seedbed soil, the covering soil, or the entire seedling soil. Simply, the seedling soil and such formulations can be alternately laid in layers. When applied to a paddy field, a solid formulation (such as a large granule, a pack, a granule, and a water-dispersible granule) or a liquid formulation (such as a suspending agent and an emulsifiable concentrate) is usually applied to the flooded paddy field. At the transplanting stage, a suitable formulation can be applied to the soil as it is or after being mixed with fertilizers, etc., or injected into the soil. In addition, a liquid medicine of an emulsifiable concentrate, a suspending agent, etc. can be applied to the water inflow sources of the paddy field water, such as the water inlet and the irrigation device. In this case, the treatment can be completed along with the supply of water, and thus can be achieved in a labor-saving manner.

[0213] In the case of upland field crops, during the process from sowing to seedling raising, the seeds or the cultivation medium near the plants, etc. can be treated. In the case of plants directly sown in the upland field, in addition to directly treating the seeds, treating the roots of the plants in cultivation is preferred. Specifically, the treatment can be carried out by, for example, applying granules to the soil, or irrigating the soil with a formulation in the form of a water-diluted or undiluted liquid. Another preferred treatment is to mix granules into the cultivation medium before sowing. In the case of cultivated plants to be transplanted, in addition to direct seed treatment, preferred examples of treatment during the process from sowing to seedling raising also include irrigating the seedbed for seedling raising with a formulation in the form of a liquid; and applying granules to the seedbed for seedling raising. It also includes treating the planting pit with granules at the time of planting; and mixing granules into the cultivation medium near the transplanting site. The agricultural and horticultural fungicides of the present invention are usually used as formulations that are easy to apply, and are prepared by conventional methods for preparing agrochemical formulations. That is, the amide compound represented by the general formula [I] of the present invention or its salt, an appropriate carrier, and if necessary, adjuvants are blended at an appropriate ratio, and through steps such as dissolution, separation, suspension, mixing, infiltration, adsorption, and / or attachment, it can be formulated into an appropriate form for application, such as a suspension concentrate, an emulsifiable concentrate, a soluble concentrate, a wettable powder, a water-dispersible granule, a granule, a powder, a tablet, and a pack.

[0214] In addition to the active ingredient, the agricultural and horticultural fungicidal composition of the present invention may optionally contain additives commonly used in agrochemical formulations. Examples of additives include carriers such as solid or liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, sticking agents, antifreeze agents, anti-caking agents, disintegrants and stabilizers. If necessary, preservatives, plant debris, etc. can also be used as additives. These additives can be used alone or in combination of two or more kinds.

[0215] Examples of solid carriers include natural minerals such as quartz, clay, kaolin, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride; organic solid carriers such as synthetic silicic acid, synthetic highly dispersed silicic acid, synthetic silicate, starch, cellulose and plant powders (e.g., sawdust, coconut shell, corncob, tobacco stalk, etc.); plastic carriers such as polyethylene, polypropylene and polyvinylidene chloride; urea; hollow inorganic materials; hollow plastic materials; and fumed silica (white carbon). These solid carriers can be used alone or in combination of two or more kinds.

[0216] Examples of liquid carriers include alcohols, including monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerol; polyhydric alcohol compounds such as propylene glycol ethers; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; straight-chain ethers or cyclic ethers such as diethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as normal paraffins, naphthenes, isoparaffins, kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate and dimethyl adipate; lactones such as γ-butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidone and N-methylpyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil; and water. These liquid carriers can be used alone or in combination of two or more kinds.

[0217] Exemplary surfactants used as dispersants or spreading agents include nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl phenyl ethers (e.g., polyoxyethylene nonyl phenyl ether), polyoxyethylene dialkyl phenyl ethers, polyoxyethylene alkyl phenyl ether - formaldehyde condensates, polyoxyethylene - polyoxypropylene block copolymers, polystyrene - polyoxyethylene block polymers, alkyl polyoxyethylene - polypropylene block copolymer ethers, polyoxyethylene alkyl amines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bis(phenyl ether), polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylene glycols, polyoxyalkylene - added acetylene glycols, polyoxyethylene ether - type silicones, ester - type silicones, fluorosurfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, alkyl aryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalenesulfonates, alkyl naphthalenesulfonates, salts of naphthalene sulfonic acid - formaldehyde condensates, salts of alkyl naphthalene sulfonic acid - formaldehyde condensates, fatty acid salts, polycarboxylates, polyacrylates, N - methyl - fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants including alkyl amine salts such as lauryl amine hydrochloride, stearyl amine hydrochloride, oleyl amine hydrochloride, stearyl amine acetate, stearyl aminopropylamine acetate, alkyl trimethyl ammonium chlorides, and alkyl dimethyl benzalkonium chlorides; and amphoteric surfactants such as amino acid - type or betaine - type amphoteric surfactants. These surfactants can be used alone or in combination of two or more.

[0218] Examples of binders or tackifiers include carboxymethyl cellulose or its salts, dextrin, soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol with an average molecular weight of 6,000 to 20,000, polyethylene oxide with an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyamino carboxylic acid chelates, cross - linked polyvinyl pyrrolidone, maleic acid - styrene copolymer, (meth)acrylic acid copolymer, semi - esters of polyol polymers and dicarboxylic anhydrides, water - soluble polystyrene sulfonates / esters, paraffin wax, terpenes, polyamide resins, polyacrylates, polyoxyethylene, waxes, polyethylene alkyl ethers, alkyl phenol - formaldehyde condensates, and synthetic resin emulsions.

[0219] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compounds and polysaccharides; and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0220] Examples of colorants include inorganic pigments such as iron oxide, titanium oxide and Prussian blue; and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

[0221] Examples of antifreezing agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol and glycerol.

[0222] Examples of adjuvants for preventing caking or promoting disintegration include polysaccharides (starch, alginic acid, mannose, galactose, etc.), polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyamino carboxylic acid chelates, sulfonated styrene-isobutylene-maleic anhydride copolymer and starch-polyacrylonitrile graft copolymer.

[0223] Examples of stabilizers include desiccants such as zeolite, quicklime and magnesium oxide; antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0224] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. In addition, if necessary, other adjuvants can also be used, including functional spreading agents, activity enhancers such as metabolic inhibitors (piperonyl butoxide, etc.), antifreezing agents (propylene glycol, etc.), antioxidants (BHT, etc.) and ultraviolet absorbers.

[0225] The content of the active ingredient compound in the agricultural and horticultural fungicides of the present invention can be adjusted as needed, and for example, it is suitably selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural fungicides. For example, when the agricultural and horticultural fungicide is a powder, granule, emulsifiable concentrate or wettable powder, the content of the active ingredient compound is suitably 0.01 to 50 parts by weight (0.01% to 50% by weight based on the total weight of the agricultural and horticultural fungicide).

[0226] The application rate of the agricultural and horticultural fungicides of the present invention can vary depending on various factors, such as the purpose, the state of the target disease, the growth condition of the crop, the tendency of disease infestation, the climate, the environmental conditions, the formulation, the application method, the application site, the application timing, etc. However, for example, depending on the purpose, the application rate of the active ingredient compound per 10 ares is suitably selected from the range of 0.001 g to 10 kg, and preferably 0.01 g to 1 kg. In addition, in order to expand the range of target pests and diseases and determine the appropriate application timing for pest and disease control, or to reduce the dosage, the agricultural and horticultural fungicides of the present invention can be used after being mixed with other agricultural or horticultural insecticides, acaricides, nematicides, fungicides, biological pest control agents, etc. In addition, depending on its application, the agricultural and horticultural fungicides can be used after being mixed with herbicides, plant growth regulators, fertilizers, etc. Examples of such additional agricultural and horticultural insecticides, acaricides and nematicides for the above purposes include 3,5-xylyl methylcarbamate (XMC), crystal protein toxins produced by Bacillus thuringiensis (such as Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis kurstaki and Bacillus thuringiensis tenebrionis), BPMC (2-(1-methylpropyl)phenyl N-methylcarbamate), insecticidal compounds derived from Bt toxins, chlorobenzilate (CPCBS), dichlorodiisopropyl ether (DCIP), 1,3-dichloropropene (D-D), DDT, NAC, O-4-dimethylaminosulfonylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropyl isocyanurate (TPIC), fluvalinate, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid, acetonitrile, acephate, abamectin, avermectin B, sulfotep, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, chlorpyrifos-methyl, isamidofos, isoamidofos, isoxathion, isopropylamine phosphate, isoprocarb (MIPC), ivermectin, cyanofenphos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, etofenprox, fenamiphos, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, fenobucarb, fenthion, isofenphos-methyl, fenpyroximate, fipronil, flonicamid, fluazuron, flusilazole, fluthiacet-methyl, flufenoxuron, formetanate, formothion, fubfenprox, gamma-cyhalothrin, furathiocarb, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronil, fipronPhenothrin, Cyfluthrin, Diflubenzuron, Butylpyridaben, Flufenzine, Cyhexatin, Cypermethrin, Methacrifos, Dimethoate, Tetramethrin, Silafluofen, Cyromazine, Spinetoram, Spinosad, Spirodiclofen, Spirotetramat, Methoprene, Spirohexanone, Spirotetramat, Fluvalinate, Prothiofos, Sulfoxaflor, Lambda-cyhalothrin, Diazinon, Fluvalinate, Dazomet, Thiacloprid, Thiamethoxam, Thiodicarb, Cartap, Thiosultap, Thiosultap-sodium, Phosalone, Ethion, Thiafluamid, DEET, Dieldrin, Ethofenprox, Tetradifon, Tetramethrin, Butylpyrimiphos, Tebufenozide, Pyridaben, Esfenvalerate, Chlorfluazuron, Isofenphos, Temephos, Deltamethrin, Terbufos, Tralopyril, Tetrabromomethrin, Transfluthrin, Triazamate, Triazuron, Tricyclazole, Trichlorfon, Chlorfluazuron, Tolfenpyrad, Dibrom, Nitrothal-isopropyl, Nitenpyram, Flucycloxuron, Noviflumuron, Hydroprene, Pyrafluprole, Pyridaphenthion, Pyridaben, Pyridalyl, Pyrafluprole, Pyriprole, Pyriproxyfen, Pirimicarb, Pyrimidifen, Pirimiphos-methyl, Pyrethrin, Fipronil, Quinoxyfen, Fenamiphos, Bromopropylate, Fenitrothion, Phenoxycarb, Benfuracarb, Phenothrin, BPMC, Fensulfothion, Fenthion, PAP, Fenvalerate, Tebuconazole, Fosthiazate, Chlordimeform, Buprofezin, Buprofezin, Fubfenprox, Flubrocythrinate, Flubendiamide, Flupentixol, Flumethrin, Flurimfen, Prothiofos, Protrifenbute, Flonicamid, Propaphos, Comite, Profenofos, Profluthrin, PHC, Bromopropylate, Beta-cyfluthrin, Chlorfluazuron, Hexythiazox, Heptenophos, Permethrin, Benclothiaz, Oxamyl, Bensultap, Benzoximate, Benfuracarb, Phoxim, Phosalone, Fosthiazate, Butocarboxim, Phosphamidon, Phosphocarb, Phosmet, Polynactins, Chlordimeform, Formothion, Phorate, Machine oil, Malathion, Milbemycin, Milbemycin-A,Methiocarb, mefenamic acid, mesulfenfos, methomyl, snail antagon, metaflumizone, methamidophos, anthracene, sodium metabisulfate, methiocarb, DMTP, methyl isothiocyanate, methyl neodecylamide, methyl parathion, methoxychlor, methoxyfenozide, methoxyfluthrin, methoprene, cypermethrin, chlorfenapyr, chlorfenapyr, monocrotophos, cypermethrin, lambda-cyhalothrin, lyanodine, lufenuron, resmethrin, lepidomic acid, rotenone, levamisole hydrochloride, fenbutin, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide (tricyclotin), calcium cyanamide, calcium polysulfide, sulfur, nicotine sulfate, isoxathiapiprolin, methoxadone and flufenapyr.

[0227] Examples of agricultural and horticultural fungicides for the same purposes as above include aureofungin, azaconazole, thiram, acypetacs, acibenzolar, benzothiadiazole, azoxystrobin, anilazine, indaziflam, chlorthiamid, allyl alcohol, aldimorph, ammonium dithio-carbamate, isotianil, isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, imazalil, guazatine, guazatine octanoate, guazatine triacetate, amisulbrom, uniconazole, uniconazole-P, echlomezole, chlorthiophos, etaconazole, thifluzamide, ethirimol, iturin, ethoxyquin, edifenphos, enostroburin, epoxiconazole, oxadixyl, oxycarboxin, copper 8-hydroxyquinolate, oxytetracycline, copper quinolate, imazoxazole, imazoxazole fumarate, oxolinic acid, octhilinone, furametpyr, orysastrobin, sodium metam, kasugamycin, dimethirimol, cyproconazole, carbendazim, carboxin, carvone, quinazamid, hydroxyquinolinylacetone, quinoxyfen, binapacryl, captafol, captan, kiralaxyl, chlorobenzthiazone, quintozene, guazatine, thiofanate, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, dichlone, tetrachloroquinoxaline, chloropicrin, chlorfenfenarimol, buscopan, tricyclazole, cyproconazole, clozylacon, tributyltin oxide, triflumizole, trifloxystrobin, azoxystrobin, tolylfluanid, etridiazole, quintozene, natamycin, sodium thiram, phthalide, nitrobenzene ethylene, fenarimol, copper nonylphenol sulfonate, quinoline acrylate, validamycin, valifenalate, harpin protein, bixafen, picoxystrobin, picobenzamide, bithionol, bitertanol, hydroxyisoxazole, potassium hydroxyisoxazole, binapacryl, biphenyl, dicloran, hymexazol, pyraoxystrobin, binapacryl, pyraclostrobin, iprovalicarb, pyriofenone, pyrimethanil, picloram, chlorpyrifos-methyl, pyroquilon, vinclozolin, oxpoconazole, iminoctadine, oxpoconazole, prednisone, fenarimol, carboxin, blastox, cyazofamid, ferbam, triphenyltin, fenpiclonil, amisulbrom, fenbuconazole, mepronil, fenpropidin, fenpropimorph, cyprodinil, phthalide, buthiobate, buthiobate, ethirimol, dimethomorph, tridemorph, fenfuram, fludioxonil, flusilazole, sulfentrazone, fluopicolide, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, sevadex, flumetylsulforim, flumetramide, flumorph, propoxyquinoline, prochloraz, procymidone, propoxur, prothioconazole, propamocarb, propiconazole, mancozeb, flufenzin, thiabendazole, furconazole, hexachlorobutadiene, hexaconazole, hexylthiofos, 3-benzothiophen-2-yl-5,6-dihydro-1,4,2-oxathiazine-4-oxide, benalaxyl, Benalaxyl-M, carboxin, benomyl, blastophthorin, guazatine, penconazole, benzamorf, dimefuron, benzohydroxamic acid, bentaluron, benthiazole, benthiavalicarb-isopropyl, pyrasulfotole, flufenpyr-ethyl, boscalid, edifenphos, fosetyl-aluminum, polyoxin, polyoxorim, ziram, chlorothalonil, formaldehyde, engine oil, mancozeb, mancozeb, mandipropamid, methfuroxam, myclobutanil, milbemycin, metiram, mecarbinzid, sulfotep, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, mancozeb, methyl isothiocyanate, methyl bromideMetconazole, tiadinil, ofurace, metconazole, metrafenone, cymoxanil, metalaxyl, dicofol, tolclofos-methyl, mepronil, iodomethane, pyrazole, benzalkonium chloride, such as inorganic fungicides like basic copper chloride, basic copper sulfate and silver, sodium hypochlorite, copper hydroxide, wettable sulfur, calcium polysulfide, potassium bicarbonate, sodium bicarbonate, sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, copper compounds such as copper 8-hydroxyquinoline (copper oxide), zinc sulfate, copper sulfate pentahydrate, ipflufenoquin, pyridachlometyl, fluoxapiprolin, fluoxytioconazole, pronitridine, picarbutrazox and metconazole.,

[0228] In addition, examples of herbicides include 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA-thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, atrazine, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, aminotriazole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, alorac, isoproturon, amicarthiazol, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, hexazinone, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, bromacil, ipfencarbazone, iprymidam, imazaquin, imazamox, imazapyr, imazamethapyr, imazethapyr, imazapic, indaziflam, indanofan, indole-3-butyric acid, uniconazole-P, glyphosine, pebulate, ethametsulfuron, metsulfuron-methyl, ethalfluralin, thiobencarb, etychlozate-ethyl, ethidimuron, nitrophen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, ethobenzanid, triazosulfuron, butylate, cafenstrole,Cambendichlor, Carbasulam, Carfentrazone-ethyl, Carfentrazone-ethyl, Carflex, Carbetamide, Carboxazole, Quizalofop-p-ethyl, Quizalofop-p-tefuryl, Quizalofop-p-ethyl, Metolachlor, Cinidon-ethyl, Quinonamid, Quinclorac, Quinmerac, Benzthiazuron, Ciodinate, Glyphosate, Glufosinate-ammonium, Glufosinate-p, Ethofumesate, Clethodim, Cloxyfonac, Clodinafop-propargyl, Clodinafop-propargyl-ester, Chlorotoluron, Clopyralid, Cloproxydim, Cloprop, Chlorbromuron, Clofop, Clomazone, Chloronitrofen, Methoxyfenoxad, Clomeprop, Chlorazifop, Chlorazine, Diethamquat, Dicamba, Cycluron, Cycloate, Butroxydim, Diclosulam, Cyprosulfuron, Dichlorprop, Dichlorprop-P, Dichlobenil, Dichlorprop, Diclofop-methyl, Benalaxyl, Dichloralurea, Diquat, Chloroxuron, Disul, Cycluron, Fluthiacet-methyl, Diallate, Dinoseb, Dinofenate, Nitrothal-isopropyl, Cyhalofop-butyl, Diphenamid, Chloroxuron, Difenopenten, Difenzoquat, Cybutryne, Ciprazine, Cyprazole, Diflufenican, Diflufenzopyr, Desmetryn, Cyclanilide, Butamifos, Gibberellin, Simazine, Chloroneb, Dimethachlor, DimidazonIsopropylamine, dimethenamid, simetryn, simetol, oxazolidinone, cyproconazole, chloranil, sulphuric acid, sulfamethoxazole, sulfamethoxazole, sulfamethoxazole-methyl ... Tetrafluron, thenylchlor, tebutam, thiocarb, terbumeton, pyraflutole, tefuryltrione, cypermethrin, isobutachlor, terbuchlo, terbuchlo, terbutryn, terfenadone, oxime, triazine, bensulfuron, wild wheat chlorpyrifos, tricamba, triclopyr, trithiocarb, tritac, trifluorosulfuron, trifluorosulfuron-methyl, trifluralin lin), trifloxysulfuron, tripropindan, bensulfuron-methyl, bensulfuron-methyl, trifop, trifopsime, trimethoate, naptalam, naproxen, nicosulfuron, sulfone, herbicide, nitrofluorfen, fluchloramide, chlorpyrifos, noruron, avena cava, paclobutrazol, paraquat, parafluron, fluazifop, haloxyfop-ethyl, haloxyfop-ethyl, flunitril, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos oxadiazole, fluazifop-butyl, bispyribac-butyl, bispyribac-butyl-sodium, pydanon, pinoxaden, pyrimidine, pyrimidosulfuron, pyrazoxyfen, pyrazosulfuron-ethyl, pyrazolate, bilanfos, pyrazosulfuron-butyl, chlorpyrifos, pyridafol, pyrimidosulfuron-butyl, pyridate, pyrimidosulfuron, pyrimidosulfuron-butyl-sodium, pyridate, pyrimidosulfuron, pyrimidosulfuron-butyl, pyrimisulfan, pyrimidosulfuron-butyl, pyroxasulfone,pyribenzoxim, fenasulam, metamitron, fenuron, fenoxasulfone, fenoxaprop-p-ethyl, quizalofop-p-ethyl, quizalofop-ethyl, clethodim, cloprop, diuron, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl, butachlor, flupropacil, butamifos, buthiuron, buthidazole, butylate, carbetamide, butenachlor, butroxydim, pendimethalin, flamprop, fomesafen, flufenacet, flupyrsulfuron-methyl, fluazifop-p-butyl, quizalofop-p-tefuryl, fluchloraminopyr, fluroxypyr, fluthiacet-methyl, fluometuron, acifluorfen-sodium, flurochloridone, nitrofen, fluorodifen, pyraflufen-ethyl, flumioxazin, flucarbazone-sodium, fluchloralin, flazasulfuron, fluthiamide, flufenican, flufenzin, flupropacil, tetrafluropropionic acid, flumiclorac-pentyl, flumioxazin, flumipropyn, flumezin, fluometuron, sulfentrazone, fluridone, flurtamone, fluroxypyr, pretilachlor, propazine, prometryn, procyazine, prodiamine, prosulfalin, flazasulfuron, pyributicarb, pyraclofos, propachlor, propazine, propanil, propyzamide, propisochlor, cis-jasmone, pyribenzoxim, pronamide, flufenoxuron, profluralin, prohexadione-calcium, propoxycarbazone-sodium, propoxycarbazone, pyrazolate, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, (C-461) hexachloropropene, hexazinone, pethoxamid, benazolin, penoxsulam, pebulate, flurochloridone, vernolatePyributicarb, tribenuron-methyl, amino acid herbicide, benzipram, benzylaminopurine, benthiocarb, bispyribac-sodium, bensulide, bensulfuron-methyl, benzoylprop-ethyl, benzobicyclon, benzofenap, benzofluor, bentazone, butylate, benthiocarb, pendimethalin, cycloxydim, fluchloralin, benfuresate, bialaphos, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, medinoterb, diuron, mesosulfuron-methyl, mesotrione, mesoprazine, metazosulfuron, methabenzthiazuron, metobenzuron, metamifop, metam-sodium, methalpropalin, methazole, methiobencarb, methyldymron, methoxuron, penoxsulam, metsulfuron-methyl, metflurazon, diuron, pyridafol, oxyfluorfen, metolachlor, metribuzin, mepiquat chloride, pretilachlor, flazasulfuron, heptanilide, monisouron, monuron, chloroacetic acid, linuron, molinate, paraquat dichloride, iodosulfuron-methyl-sodium, iodosulfuron, ioxynil, iodomethane, lactofen, linuron, rimsulfuron, lenacil, thiocarb, calcium peroxide, methyl bromide, pyraflufen-ethyl, and tetrafluoroethylamine.

[0229] Examples of biopesticides include virus formulations such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxvirus (EPV); microbial pesticides used as insecticides or nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, and Pasteuria penetrans; microbial pesticides used as fungicides such as Trichodermalignorum, Agrobacterium radiobactor, Erwinia carotovora, and Bacillus subtilis; and biopesticides used as herbicides such as Xanthomonas campestris. The combined use of the agricultural and horticultural fungicides of the present invention with the aforementioned biopesticides as a mixture can be expected to provide the same effects as above.

[0230] Other examples of biopesticides used in combination with the agricultural or horticultural fungicides of the present invention include natural enemy organisms such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, and Orius sauteri; microbial pesticides such as Beauveria brongniartii; and pheromones such as (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-eicosen-10-one, and 14-methyl-1-octadecene.

[0231] Hereinafter, production examples of representative compounds of the present invention and their intermediates will be described in more detail, but the present invention is not limited to these examples. THF, DMF, TEA, DMAP, and EtOH represent tetrahydrofuran, dimethylformamide, triethylamine, 4-dimethylaminopyridine, and ethanol, respectively, and mmol represents millimole. The value (%) in parentheses after the amount of the product obtained in the following examples and reference examples indicates the yield. [Examples]

[0232] Example 1. Production of Compound No. I-A-101

[0233] To a mixed solution of carboxylic acid [III] (11 g, 41 mmol) produced by the method of Reference Example 2, 2-aminomethylpyridine (5.3 g, 49 mmol), tetrahydrofuran (0.41 L), 2-chloro-1-methylpyridinium iodide (21 g, 82 mmol), triethylamine (17 mL, 0.12 mol), and DMAP (0.50 g, 4.1 mmol) were added, and the mixture was stirred under heating and reflux conditions for 6 hours. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The obtained organic phase was dried over sodium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 12 g (yield: 78%) of the compound I-A-101 .

[0234] Example 2. Production of Compound No. I-A-261

[0235] To a mixed solution of compound I-A-257 (0.10 g, 0.22 mmol), 2-fluoroboric acid (33 mg, 0.24 mmol), Pd(dppf)Cl2·MeCN (18 mg, 0.022 mmol), and toluene (1.8 mL), 1 M aqueous K3PO4 solution (0.43 mL, 0.43 mmol) was added, and the mixture was stirred at 90 °C under an argon atmosphere for 3 hours. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The obtained organic phase was dried over sodium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 86 mg (yield: 92%) of the compound I-A-261 .

[0236] The raw materials or intermediates of the present invention can be produced, for example, by the following methods. These compounds can be produced by known methods or methods known per se.

[0237] Reference Example 1. Production method of intermediate [II] A mixed solution of ethyl 4-(1,1-dimethylethyl)-α-methylenephenylacetate (16 g, 70 mmol), triethylbenzylammonium chloride (TEBAC 1.6 g, 7.0 mmol) and chloroform (210 mL) was added dropwise to an aqueous 25 wt% sodium hydroxide solution (42 g, 260 mmol) with stirring at room temperature, and the mixture was vigorously stirred overnight at the same temperature. The reaction mixture was separated into an organic phase and an aqueous phase, and the organic phase was washed with saturated brine. The organic phase was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was separated and purified by silica gel column chromatography to obtain 21 g (yield: 95%) of ethyl 2,2-dichloro-1-[4-(1,1-dimethylethyl)phenyl]cyclopropanecarboxylate [II].

[0238] Reference Example 2. Production method of intermediate [III] Lithium hydroxide monohydrate (14 g, 0.33 mol) was added to a mixed solution of ethyl 2,2-dichloro-1-[4-(1,1-dimethylethyl)phenyl]cyclopropanecarboxylate [II] (21 g, 67 mmol), EtOH (135 mL) and water (13 mL), and the mixture was stirred at 60 °C for 4 hours. After the reaction was completed, the solvent was evaporated under reduced pressure, and the residue was acidified with 1 M hydrochloric acid. Then, the mixture was extracted twice with ethyl acetate. The obtained organic phase was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 20 g (yield: quantitative) of 2,2-dichloro-1-[4-(1,1-dimethylethyl)phenyl]cyclopropanecarboxylic acid [III].

[0239] [Table 88] · Table III-A: For the production of carboxylic acids of general formula [I-A]

[0240] [Table 89] · Table III-A: For the production of carboxylic acids of general formula [I-A] (continued)

[0241] [Table 90] · Table III-A: For the production of carboxylic acids of general formula [I-A] (continued)

[0242] [Table 91] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0243] [Table 92] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0244] [Table 93] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0245] [Table 94] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0246] [Table 95] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0247] [Table 96] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0248] [Table 97] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0249] [Table 98] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0250] [Table 99] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0251] [Table 100] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0252] [Table 101] · Table III-A: Carboxylic Acids for the Production of Carboxylic Acids of General Formula [I-A] (Continued)

[0253] [Table 102] ·Table III-A: Carboxylic acids for the production of carboxylic acids of general formula [I-A] (continued)

[0254] [Table 103] ·Table III-A: Carboxylic acids for the production of carboxylic acids of general formula [I-A] (continued)

[0255] [Table 104] ·Table III-A: Carboxylic acids for the production of carboxylic acids of general formula [I-A] (continued)

[0256] [Table 105] ·Table III-A: Carboxylic acids for the production of carboxylic acids of general formula [I-A] (continued)

[0257] [Table 106] ·Table III-B: Carboxylic acids for the production of carboxylic acids of general formula [I-B]

[0258] [Table 107] ·Table III-C: Carboxylic acids for the production of carboxylic acids of general formula [I-C]

[0259] [Table 108] ·Table III-L: Carboxylic acids for the production of carboxylic acids of general formula [I-L]

[0260] In the following, formulation examples are shown, but the present invention is not limited thereto. In the formulation examples, "parts" means parts by weight.

[0261] Formulation Example 1. The above components are uniformly mixed for dissolution to obtain an emulsifiable concentrate formulation.

[0262] Formulation Example 2. Compound [I] of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above components are uniformly mixed and then pulverized to obtain a powder formulation.

[0263] Formulation Example 3. 5 parts of the compound [I] of the present invention 90 parts of a mixture of bentonite powder and clay powder 5 parts of calcium lignosulfonate The above components are uniformly mixed. After adding an appropriate volume of water, the mixture is kneaded, granulated and dried to obtain a granule formulation.

[0264] Formulation Example 4. 20 parts of the compound [I] of the present invention 75 parts of kaolin and synthetic highly dispersed silicic acid 5 parts of a mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate The above components are uniformly mixed and then pulverized to obtain a wettable powder formulation.

[0265] Formulation Example 5. Preparation procedure: The above components except water are uniformly mixed, and the mixture is dispersed in water to obtain a suspending concentrate formulation.

[0266] Hereinafter, test examples related to the present invention are shown, but the present invention is not limited thereto.

[0267] Test Example 1. Test on the control efficacy against Alternaria brassicae The formulation prepared from the compound according to Formulation Example 1 of the present invention is diluted with water to a predetermined concentration. 10 ml of the diluted formulation is applied to the stems and leaves of Chinese cabbage plants (variety: Musou) at the 3 - 5 leaf stage grown in a pot with a diameter of 5 cm. After the formulation has dried, the Chinese cabbage plants are inoculated by spraying a spore suspension of Alternaria brassicae. The Chinese cabbage plants are kept under humid conditions at 20°C for one day, and then transferred to a greenhouse to allow the disease to develop. Five days after inoculation, the control efficacy is evaluated according to the criteria shown below. [Equation 1] Control rate % = 100×(percentage of average lesion area in the untreated plot - percentage of average lesion area in the treated plot) / percentage of average lesion area in the untreated plot

[0268] Criteria 0: Control rate is 9% or less. 1: Control rate is 10% to 19%. 2: Control rate is 20% to 29%. 3: Control rate is 30% to 39%. 4: Control rate is 40% to 49%. 5: The control rate is 50% to 59%. 6: The control rate is 60% to 69%. 7: The control rate is 70% to 79%. 8: The control rate is 80% to 89%. 9: The control rate is 90% to 99%. 10: The control rate is 100%.

[0269] The results of the tests revealed compounds I-A-3, I-A-4, I-A-5, I-A-25, I-A-36, I-A-38, I-A-39, I-A-43, I-A-52, I-A-54, I-A-56, I-A-58, I-A-68, I-A-81, I-A-94, I-A-98, I-A-99, I-A-100, I-A-101, I-A-102, I-A-103, I-A-106, I-A-114, I-A-123, I-A-132, I-A-135, I-A-160, I-A-162, I-A-168, I-A-175, I-A-186, I-A-198, I-A-200, I-A-206, I-A-214, I-A-218, I-A-219, I-A-238, I-A-239, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-256, I-A-257, I-A-258, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-278, I-A-279, I-A-281, I-A-282, I-A-284, I-A-285, I-A-286, I-A-287, I-A-288, I-A-289, I-A-290, I-A-291, I-A-293, I-A-295, I-A-297, I-A-298, I-A-299, I-A-300, I-A-302, I-A-348, I-A-349, I-A-351, I-A-352, I-A-353, I-A-355, I-A-357, I-A-360, I-A-364, I-A-365, I-A-383, I-A-385, I-A-386, I-A-387, I-A-388, I-A-390, I-A-392, I-A-393, I-A-394, I-A-398, I-A-400, I-A-408, I-A-410, I-A-411, I-A-412, I-A-414, I-A-416, I-A-422, I-A-423, I-A-425, I-A-426, I-A-427, I-A-428, I-A-429, I-A-468, I-A-474, I-A-476, I-A-483, I-A-488, I-A-489, I-A-494, I-A-529, I-A-535, I-A-543 at a concentration of 200 ppm.I-A-544, I-A-550, I-A-558, I-A-559, I-A-560, I-A-562, I-A-563, I-A-568, I-A-572, I-A-573, I-A-574, I-A-575, I-A-576, I-A-577, I-A-578, I-A-579, I-A-580, I-A-581, I-A-582, I-A-583, I-A-584, I-A-585, I-A-586, I-A-588, I-A-591, I-A-592, I-A-593, I-A-596, I-A-598, I-A-601, I-A-608, I-A-611, I-A-612, I-A-614, I-A-618, I-A-619, I-A-620, I-A-621, I-A-622, I-A-626, I-A-627, I-A-629, I-A-630, I-A-635, I-A-636, I-A-637, I-A-638, I-A-639, I-A-643, I-B-2, I-B-17, I-C-15, I-C-16, I-C-17, I-C-18, I-C-19, I-C-23, I-C-24, I-C-25, I-C-26, I-C-28, I-K-9, I-K-13, I-K-14, I-K-15, I-K-16, I-K-17, I-K-18, I-K-19, I-K-20, I-K-21, I-K-23, I-K-24, I-K-25 and I-K-26 showed activity at level 1 or higher.

[0270] Test Example 2. Test on the control efficacy against Phytophthora infestans of tomato The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the aerial parts of tomato plants (variety: Momotaro) at the 3-4 leaf stage grown in pots with a diameter of 9 cm. After the formulation had dried, the tomato plants were inoculated by spraying a zoosporangium suspension of Phytophthora infestans. The tomato plants were kept at 20 °C under humid conditions for one day and then transferred to a greenhouse to allow the disease to develop. At 5 or 6 days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0271] The test results revealed that the compound I-A-17 at a concentration of 200 ppm showed activity at level 1 or higher.

[0272] Test Example 3. Test on the control efficacy against Botrytis cinerea of cucumber The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the aerial parts of cucumber plants (cultivar: YOTUBA) at the one-leaf stage grown in pots with a diameter of 9 cm. After the formulation had dried, the cucumber plants were inoculated by wetting a paper disk placed at the center of the leaf with a spore suspension of Botrytis cinerea of cucumber. The cucumber plants were maintained at 15 °C under constant humidity conditions to allow the disease to develop. Five or six days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0273] The results of the tests revealed compounds I-A-1, I-A-3, I-A-4, I-A-5, I-A-13, I-A-17, I-A-25, I-A-35, I-A-36, I-A-38, I-A-39, I-A-40, I-A-49, I-A-52, I-A-54, I-A-55, I-A-56, I-A-58, I-A-59, I-A-62, I-A-63, I-A-65, I-A-68, I-A-71, I-A-75, I-A-76, I-A-77, I-A-78, I-A-79, I-A-81, I-A-89, I-A-94, I-A-99, I-A-100, I-A-101, I-A-102, I-A-113, I-A-114, I-A-123, I-A-124, I-A-129, I-A-132, I-A-133, I-A-147, I-A-150, I-A-152, I-A-155, I-A-157, I-A-159, I-A-162, I-A-163, I-A-165, I-A-167, I-A-169, I-A-171, I-A-172, I-A-173, I-A-180, I-A-186, I-A-188, I-A-196, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-217, I-A-218, I-A-220, I-A-222, I-A-226, I-A-238, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-255, I-A-256, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-276, I-A-278, I-A-279, I-A-280, I-A-281, I-A-282, I-A-283, I-A-284, I-A-285, I-A-286, I-A-287, I-A-288, I-A-289, I-A-290, I-A-291, I-A-292, I-A-293, I-A-294, I-A-295, I-A-296, I-A-297, I-A-298, I-A-299, I-A-300, I-A-301, I-A-302, I-A-303, I-A-348, I-A-349, I-A-351 at a concentration of 200 ppm.I-A-352, I-A-355, I-A-356, I-A-357, I-A-360, I-A-361, I-A-362, I-A-364, I-A-365, I-A-366, I-A-367, I-A-369, I-A-370, I-A-376, I-A-378, I-A-379, I-A-381, I-A-383, I-A-385, I-A-386, I-A-387, I-A-388, I-A-389, I-A-390, I-A-391, I-A-392, I-A-393, I-A-398, I-A-399, I-A-400, I-A-401, I-A-403, I-A-404, I-A-405, I-A-406, I-A-407, I-A-408, I-A-409, I-A-410, I-A-411, I-A-412, I-A-413, I-A-414, I-A-415, I-A-416, I-A-417, I-A-419, I-A-420, I-A-421, I-A-422, I-A-423, I-A-424, I-A-425, I-A-426, I-A-427, I-A-428, I-A-429, I-A-430, I-A-431, I-A-432, I-A-434, I-A-435, I-A-436, I-A-437, I-A-438, I-A-441, I-A-442, I-A-443, I-A-444, I-A-445, I-A-447, I-A-448, I-A-449, I-A-450, I-A-451, I-A-452, I-A-453, I-A-454, I-A-456, I-A-457, I-A-458, I-A-459, I-A-460, I-A-461, I-A-462, I-A-463, I-A-464, I-A-465, I-A-466, I-A-467, I-A-468, I-A-469, I-A-470, I-A-471, I-A-472, I-A-474, I-A-475, I-A-476, I-A-477, I-A-478, I-A-479, I-A-480, I-A-481, I-A-483, I-A-485, I-A-486, I-A-487, I-A-488, I-A-489, I-A-492, I-A-493, I-A-494, I-A-495, I-A-496, I-A-497, I-A-498, I-A-499, I-A-500, I-A-502, I-A-503, I-A-504, I-A-506, I-A-507, I-A-509, I-A-510,I-A-511, I-A-512, I-A-513, I-A-514, I-A-516, I-A-518, I-A-519, I-A-520, I-A-521, I-A-522, I-A-524, I-A-525, I-A-526, I-A-527, I-A-528, I-A-529, I-A-530, I-A-531, I-A-532, I-A-534, I-A-535, I-A-536, I-A-537, I-A-538, I-A-539, I-A-540, I-A-541, I-A-543, I-A-544, I-A-550, I-A-552, I-A-555, I-A-558, I-A-559, I-A-560, I-A-561, I-A-562, I-A-563, I-A-564, I-A-565, I-A-566, I-A-567, I-A-568, I-A-569, I-A-571, I-A-572, I-A-573, I-A-574, I-A-575, I-A-576, I-A-577, I-A-578, I-A-579, I-A-580, I-A-581, I-A-582, I-A-583, I-A-584, I-A-585, I-A-586, I-A-587, I-A-588, I-A-589, I-A-590, I-A-591, I-A-592, I-A-593, I-A-594, I-A-595, I-A-596, I-A-601, I-A-602, I-A-603, I-A-604, I-A-605, I-A-606, I-A-607, I-A-608, I-A-609, I-A-610, I-A-611, I-A-612, I-A-613, I-A-614, I-A-615, I-A-617, I-A-618, I-A-619, I-A-620, I-A-621, I-A-622, I-A-623, I-A-624, I-A-625, I-A-626, I-A-627, I-A-628, I-A-629, I-A-630, I-A-631, I-A-633, I-A-634, I-A-635, I-A-636, I-A-637, I-A-638, I-A-640, I-A-641, I-A-642, I-A-643, I-A-645, I-A-646, I-A-647, I-B-2, I-B-16, I-B-17, I-C-2, I-C-13, I-C-14, I-C-15, I-C-16, I-C-17, I-C-18, I-C-19, I-C-20, I-C-21, I-C-23I-C-24, I-C-25, I-C-26, I-C-28, I-C-29, I-C-30, I-C-31, I-K-7, I-K-8, I-K-9, I-K-10, I-K-13, I-K-15, I-K-16, I-K-19, I-K-20, I-K-21, I-K-22, I-K-25, I-K-28 and I-L-3 showed activity at level 1 or higher.

[0274] Test Example 4. Test on the control efficacy against Colletotrichum orbiculare The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the aerial parts of cucumber plants (variety: YOTUBA) at the two-leaf stage grown in pots with a diameter of 9 cm. After the formulation had dried, the cucumber plants were inoculated by spraying a spore suspension of Colletotrichum orbiculare. The cucumber plants were kept under humid conditions at 20°C for one day and then transferred to a greenhouse to allow the disease to develop. Six days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0275] The results of the tests revealed compounds I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-10, I-A-16, I-A-17, I-A-25, I-A-36, I-A-37, I-A-38, I-A-39, I-A-41, I-A-43, I-A-49, I-A-52, I-A-54, I-A-55, I-A-56, I-A-57, I-A-58, I-A-59, I-A-62, I-A-63, I-A-64, I-A-66, I-A-68, I-A-70, I-A-71, I-A-75, I-A-76, I-A-77, I-A-78, I-A-80, I-A-81, I-A-89, I-A-94, I-A-98, I-A-99, I-A-100, I-A-101, I-A-102, I-A-103, I-A-106, I-A-113, I-A-114, I-A-123, I-A-127, I-A-130, I-A-132, I-A-133, I-A-135, I-A-139, I-A-147, I-A-148, I-A-150, I-A-152, I-A-154, I-A-155, I-A-157, I-A-159, I-A-160, I-A-162, I-A-164, I-A-165, I-A-167, I-A-168, I-A-169, I-A-171, I-A-172, I-A-173, I-A-175, I-A-178, I-A-180, I-A-186, I-A-188, I-A-190, I-A-192, I-A-194, I-A-195, I-A-196, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-218, I-A-219, I-A-220, I-A-226, I-A-238, I-A-239, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-255, I-A-256, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-276, I-A-277, I-A-278, I-A-279, I-A-281, I-A-282, I-A-284 at a concentration of 200 ppm.I-A-285, I-A-286, I-A-287, I-A-288, I-A-289, I-A-290, I-A-291, I-A-293, I-A-295, I-A-296, I-A-297, I-A-298, I-A-299, I-A-300, I-A-301, I-A-302, I-A-303, I-A-346, I-A-348, I-A-349, I-A-350, I-A-351, I-A-353, I-A-354, I-A-355, I-A-357, I-A-359, I-A-360, I-A-361, I-A-362, I-A-363, I-A-364, I-A-365, I-A-366, I-A-368, I-A-369, I-A-370, I-A-372, I-A-375, I-A-378, I-A-379, I-A-381, I-A-383, I-A-384, I-A-385, I-A-386, I-A-387, I-A-388, I-A-389, I-A-390, I-A-391, I-A-392, I-A-393, I-A-394, I-A-398, I-A-399, I-A-400, I-A-401, I-A-403, I-A-404, I-A-405, I-A-406, I-A-407, I-A-408, I-A-409, I-A-410, I-A-411, I-A-412, I-A-413, I-A-414, I-A-415, I-A-416, I-A-417, I-A-418, I-A-419, I-A-420, I-A-421, I-A-422, I-A-423, I-A-424, I-A-425, I-A-426, I-A-427, I-A-428, I-A-429, I-A-430, I-A-431, I-A-432, I-A-433, I-A-434, I-A-435, I-A-436, I-A-437, I-A-438, I-A-439, I-A-440, I-A-441, I-A-442, I-A-443, I-A-444, I-A-445, I-A-446, I-A-447, I-A-448, I-A-449, I-A-450, I-A-451, I-A-452, I-A-453, I-A-454, I-A-455, I-A-456, I-A-457, I-A-458, I-A-459, I-A-460, I-A-461, I-A-462, I-A-463, I-A-464, I-A-465, I-A-466, I-A-467, I-A-469, I-A-470I-A-471, I-A-473, I-A-474, I-A-475, I-A-476, I-A-477, I-A-478, I-A-479, I-A-480, I-A-481, I-A-482, I-A-483, I-A-484, I-A-485, I-A-486, I-A-487, I-A-488, I-A-489, I-A-490, I-A-491, I-A-492, I-A-493, I-A-494, I-A-495, I-A-496, I-A-497, I-A-498, I-A-499, I-A-500, I-A-501, I-A-502, I-A-503, I-A-504, I-A-505, I-A-506, I-A-507, I-A-508, I-A-509, I-A-510, I-A-511, I-A-512, I-A-513, I-A-514, I-A-515, I-A-516, I-A-517, I-A-518, I-A-519, I-A-520, I-A-521, I-A-522, I-A-524, I-A-525, I-A-526, I-A-527, I-A-528, I-A-529, I-A-530, I-A-531, I-A-532, I-A-533, I-A-534, I-A-535, I-A-536, I-A-537, I-A-538, I-A-539, I-A-540, I-A-541, I-A-542, I-A-543, I-A-544, I-A-547, I-A-548, I-A-550, I-A-551, I-A-552, I-A-553, I-A-554, I-A-555, I-A-556, I-A-557, I-A-558, I-A-559, I-A-560, I-A-561, I-A-562, I-A-563, I-A-564, I-A-565, I-A-566, I-A-567, I-A-568, I-A-570, I-A-571, I-A-572, I-A-573, I-A-574, I-A-575, I-A-576, I-A-577, I-A-578, I-A-579, I-A-580, I-A-581, I-A-582, I-A-583, I-A-584, I-A-585, I-A-586, I-A-587, I-A-588, I-A-589, I-A-590, I-A-591, I-A-592, I-A-593, I-A-594, I-A-595, I-A-596, I-A-597, I-A-598, I-A-599, I-A-600, I-A-601I-A-602, I-A-603, I-A-604, I-A-605, I-A-606, I-A-607, I-A-608, I-A-609, I-A-610, I-A-611, I-A-612, I-A-613, I-A-614, I-A-615, I-A-616, I-A-617, I-A-618, I-A-619, I-A-620, I-A-621, I-A-622, I-A-623, I-A-624, I-A-625, I-A-626, I-A-627, I-A-628, I-A-629, I-A-630, I-A-631, I-A-632, I-A-633, I-A-634, I-A-635, I-A-636, I-A-637, I-A-638, I-A-639, I-A-640, I-A-641, I-A-642, I-A-643, I-A-644, I-A-645, I-A-646, I-A-647, I-B-2, I-B-16, I-B-17, I-B-18, I-C-2, I-C-5, I-C-13, I-C-14, I-C-15, I-C-16, I-C-17, I-C-18, I-C-19, I-C-20, I-C-21, I-C-22, I-C-23, I-C-24, I-C-25, I-C-26, I-C-27, I-C-28, I-C-29, I-C-30, I-C-31, I-K-8, I-K-9, I-K-10, I-K-13, I-K-17, I-K-21, I-K-22, I-K-25, I-K-27, I-K-28 and I-L-3 showed activity at level 1 or higher.

[0276] Test Example 5. Test for control efficacy against rice blast The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the foliage of rice plants (variety: Kinmaze) at the 6-7 leaf stage grown in a pot with a diameter of 6 cm. After the formulation had dried, the rice plants were inoculated by spraying a spore suspension of the rice blast fungus. The rice plants were kept under humid conditions at 20 °C for one day and then transferred to a greenhouse to allow the disease to develop. Six days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0277] The results of the tests revealed that compounds I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-10, I-A-13, I-A-16, I-A-17, I-A-25, I-A-35, I-A-36, I-A-37, I-A-38, I-A-39, I-A-41, I-A-43, I-A-49, I-A-52, I-A-54, I-A-55, I-A-56, I-A-57, I-A-58, I-A-59, I-A-62, I-A-63, I-A-64, I-A-68, I-A-70, I-A-71, I-A-75, I-A-76, I-A-77, I-A-80, I-A-81, I-A-82, I-A-89, I-A-94, I-A-98, I-A-99, I-A-100, I-A-101, I-A-102, I-A-103, I-A-113, I-A-114, I-A-125, I-A-127, I-A-148, I-A-150, I-A-155, I-A-164, I-A-165, I-A-168, I-A-171, I-A-172, I-A-173, I-A-175, I-A-178, I-A-180, I-A-186, I-A-195, I-A-196, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-217, I-A-218, I-A-219, I-A-222, I-A-226, I-A-238, I-A-246, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-255, I-A-256, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-276, I-A-277, I-A-278, I-A-279, I-A-281, I-A-282, I-A-284, I-A-285, I-A-286, I-A-287, I-A-288, I-A-289, I-A-290, I-A-291, I-A-292, I-A-293, I-A-294, I-A-295, I-A-296, I-A-297, I-A-298, I-A-299, I-A-300, I-A-301 at a concentration of 200 ppmI-A-302, I-A-303, I-A-304, I-A-347, I-A-348, I-A-349, I-A-350, I-A-351, I-A-352, I-A-353, I-A-354, I-A-355, I-A-357, I-A-359, I-A-362, I-A-363, I-A-365, I-A-366, I-A-368, I-A-375, I-A-378, I-A-381, I-A-384, I-A-385, I-A-386, I-A-387, I-A-388, I-A-389, I-A-390, I-A-391, I-A-392, I-A-393, I-A-398, I-A-399, I-A-400, I-A-401, I-A-403, I-A-404, I-A-405, I-A-406, I-A-407, I-A-408, I-A-409, I-A-410, I-A-411, I-A-412, I-A-413, I-A-414, I-A-415, I-A-416, I-A-417, I-A-418, I-A-419, I-A-420, I-A-421, I-A-422, I-A-425, I-A-426, I-A-427, I-A-428, I-A-429, I-A-430, I-A-432, I-A-437, I-A-441, I-A-442, I-A-443, I-A-444, I-A-445, I-A-446, I-A-447, I-A-449, I-A-452, I-A-456, I-A-457, I-A-459, I-A-460, I-A-461, I-A-462, I-A-463, I-A-464, I-A-465, I-A-466, I-A-468, I-A-470, I-A-471, I-A-472, I-A-473, I-A-474, I-A-475, I-A-476, I-A-477, I-A-478, I-A-480, I-A-481, I-A-482, I-A-483, I-A-485, I-A-486, I-A-487, I-A-488, I-A-489, I-A-490, I-A-491, I-A-499, I-A-500, I-A-501, I-A-502, I-A-503, I-A-504, I-A-505, I-A-507, I-A-508, I-A-509, I-A-510, I-A-511, I-A-512, I-A-513, I-A-514, I-A-515, I-A-516, I-A-517, I-A-518, I-A-519, I-A-520I-A-521, I-A-522, I-A-524, I-A-525, I-A-526, I-A-527, I-A-528, I-A-529, I-A-530, I-A-531, I-A-532, I-A-533, I-A-534, I-A-535, I-A-536, I-A-537, I-A-538, I-A-539, I-A-540, I-A-541, I-A-542, I-A-543, I-A-545, I-A-546, I-A-547, I-A-548, I-A-549, I-A-550, I-A-551, I-A-555, I-A-556, I-A-557, I-A-558, I-A-559, I-A-560, I-A-561, I-A-562, I-A-563, I-A-564, I-A-565, I-A-568, I-A-569, I-A-570, I-A-571, I-A-572, I-A-573, I-A-574, I-A-575, I-A-576, I-A-577, I-A-578, I-A-579, I-A-580, I-A-581, I-A-582, I-A-583, I-A-584, I-A-585, I-A-586, I-A-587, I-A-588, I-A-589, I-A-590, I-A-591, I-A-592, I-A-593, I-A-594, I-A-595, I-A-596, I-A-597, I-A-598, I-A-599, I-A-600, I-A-601, I-A-602, I-A-603, I-A-604, I-A-605, I-A-606, I-A-607, I-A-608, I-A-609, I-A-610, I-A-611, I-A-612, I-A-613, I-A-614, I-A-615, I-A-619, I-A-620, I-A-621, I-A-622, I-A-623, I-A-624, I-A-625, I-A-626, I-A-627, I-A-628, I-A-629, I-A-630, I-A-632, I-A-634, I-A-635, I-A-636, I-A-637, I-A-638, I-A-639, I-A-643, I-A-644, I-A-646, I-A-647, I-B-2, I-B-16, I-B-17, I-B-18, I-C-13, I-C-14, I-C-15, I-C-16, I-C-17, I-C-18, I-C-19, I-C-20, I-C-21, I-C-22, I-C-23, I-C-24I-C-25, I-C-26, I-C-27, I-C-28, I-C-29, I-C-30, I-C-31, I-K-7, I-K-8, I-K-9, I-K-10, I-K-11, I-K-13, I-K-15, I-K-17, I-K-18, I-K-19, I-K-20, I-K-21, I-K-22, I-K-23, I-K-24, I-K-25, I-K-26, I-K-27, I-K-28, I-L-2 and I-L-3 showed activities at level 1 or higher.

[0278] Test Example 6. Test on the control efficacy against Venturia inaequalis The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the stems and leaves of apple seedlings (variety: ORIN) grown in a pot with a diameter of 5 cm. After the formulation had dried, the apple seedlings were inoculated by spraying a spore suspension of Venturia inaequalis. The apple seedlings were kept under humid conditions at 20 °C for two days and then transferred to a room at 15 °C and then appropriately humidified to promote the development of the disease. 15 days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0279] The results of the tests revealed compounds I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-10, I-A-13, I-A-16, I-A-25, I-A-35, I-A-36, I-A-37, I-A-38, I-A-40, I-A-41, I-A-43, I-A-49, I-A-54, I-A-55, I-A-56, I-A-57, I-A-58, I-A-63, I-A-68, I-A-71, I-A-75, I-A-77, I-A-78, I-A-80, I-A-81, I-A-89, I-A-94, I-A-96, I-A-97, I-A-98, I-A-100, I-A-101, I-A-102, I-A-103, I-A-113, I-A-114, I-A-127, I-A-132, I-A-133, I-A-148, I-A-150, I-A-152, I-A-157, I-A-159, I-A-160, I-A-165, I-A-168, I-A-171, I-A-175, I-A-180, I-A-186, I-A-190, I-A-192, I-A-196, I-A-198, I-A-199, I-A-200, I-A-206, I-A-218, I-A-219, I-A-220, I-A-222, I-A-226, I-A-238, I-A-239, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-276, I-A-277, I-A-278, I-A-279, I-A-281, I-A-282, I-A-284, I-A-285, I-A-286, I-A-287, I-A-288, I-A-289, I-A-290, I-A-291, I-A-293, I-A-294, I-A-295, I-A-296, I-A-297, I-A-298, I-A-299, I-A-300, I-A-301, I-A-302, I-A-303, I-A-348, I-A-349, I-A-350, I-A-351, I-A-352, I-A-353, I-A-354, I-A-355, I-A-356 at a concentration of 200 ppm.I-A-357, I-A-358, I-A-360, I-A-361, I-A-362, I-A-363, I-A-364, I-A-365, I-A-368, I-A-370, I-A-371, I-A-372, I-A-378, I-A-381, I-A-382, I-A-384, I-A-387, I-A-388, I-A-389, I-A-390, I-A-391, I-A-392, I-A-393, I-A-394, I-A-398, I-A-399, I-A-400, I-A-401, I-A-403, I-A-404, I-A-405, I-A-406, I-A-407, I-A-408, I-A-409, I-A-410, I-A-411, I-A-412, I-A-413, I-A-414, I-A-415, I-A-416, I-A-417, I-A-418, I-A-419, I-A-420, I-A-421, I-A-422, I-A-423, I-A-424, I-A-425, I-A-426, I-A-427, I-A-428, I-A-429, I-A-430, I-A-431, I-A-432, I-A-433, I-A-434, I-A-435, I-A-436, I-A-437, I-A-438, I-A-439, I-A-440, I-A-441, I-A-442, I-A-443, I-A-444, I-A-445, I-A-446, I-A-447, I-A-448, I-A-449, I-A-450, I-A-451, I-A-452, I-A-454, I-A-455, I-A-456, I-A-457, I-A-458, I-A-459, I-A-460, I-A-461, I-A-462, I-A-463, I-A-464, I-A-465, I-A-466, I-A-467, I-A-468, I-A-469, I-A-470, I-A-471, I-A-472, I-A-474, I-A-475, I-A-476, I-A-477, I-A-478, I-A-479, I-A-480, I-A-481, I-A-482, I-A-483, I-A-484, I-A-485, I-A-486, I-A-487, I-A-488, I-A-489, I-A-490, I-A-491, I-A-492, I-A-493, I-A-494, I-A-495, I-A-496, I-A-497, I-A-498, I-A-499, I-A-500, I-A-501I-A-502, I-A-503, I-A-504, I-A-505, I-A-509, I-A-510, I-A-511, I-A-512, I-A-513, I-A-514, I-A-515, I-A-516, I-A-517, I-A-518, I-A-519, I-A-520, I-A-521, I-A-522, I-A-524, I-A-525, I-A-526, I-A-527, I-A-528, I-A-529, I-A-530, I-A-531, I-A-532, I-A-533, I-A-534, I-A-535, I-A-536, I-A-537, I-A-538, I-A-539, I-A-540, I-A-541, I-A-543, I-A-544, I-A-545, I-A-548, I-A-549, I-A-550, I-A-551, I-A-555, I-A-556, I-A-558, I-A-559, I-A-560, I-A-562, I-A-563, I-A-564, I-A-565, I-A-566, I-A-567, I-A-568, I-A-569, I-A-570, I-A-571, I-A-572, I-A-573, I-A-574, I-A-575, I-A-576, I-A-577, I-A-580, I-A-581, I-A-582, I-A-583, I-A-584, I-A-585, I-A-586, I-A-587, I-A-588, I-A-589, I-A-590, I-A-591, I-A-592, I-A-593, I-A-594, I-A-595, I-A-596, I-A-597, I-A-598, I-A-599, I-A-600, I-A-601, I-A-602, I-A-603, I-A-604, I-A-605, I-A-606, I-A-607, I-A-608, I-A-609, I-A-610, I-A-611, I-A-612, I-A-613, I-A-614, I-A-615, I-A-616, I-A-617, I-A-618, I-A-619, I-A-620, I-A-621, I-A-622, I-A-623, I-A-624, I-A-625, I-A-626, I-A-627, I-A-628, I-A-629, I-A-630, I-A-631, I-A-632, I-A-633, I-A-634, I-A-635, I-A-636, I-A-637, I-A-638, I-A-639, I-A-640I-A-641, I-A-642, I-A-643, I-A-646, I-A-647, I-B-2, I-B-16, I-B-17, I-B-18, I-C-13, I-C-14, I-C-15, I-C-16, I-C-17, I-C-18, I-C-19, I-C-20, I-C-21, I-C-22, I-C-23, I-C-24, I-C-25, I-C-26, I-C-27, I-C-28, I-C-29, I-C-30, I-C-31, I-K-13, I-K-14, I-K-15, I-K-16, I-K-17, I-K-18, I-K-19, I-K-20, I-K-21, I-K-22, I-K-23, I-K-25, I-K-26, I-K-27, I-K-28 and I-L-1 showed activity at level 1 or higher.

[0280] Test Example 7. Antifungal Activity Test The following (a), (b), (c), (d), (e) and (f) were used as test fungi. Each test fungus was mixed with the optimal medium for its growth and the test compound, and placed in a 96-well plate to examine the spore germination inhibitory activity. After growth, the absorbance was measured and the half-maximal effective concentration (EC 50 50: ppm) was evaluated. (a) Botryosphaeria berengeriana (b) Colletotrichum acutatum (c) Colletotrichum gloeosporioides (d) Septoria tritici (e) Fusarium graminearum (f) Fusarium sporotrichioides

[0281] As a result of the above tests, the compounds with a half-maximal effective concentration of 200 ppm or less are listed below: (a) I-A-36 (b) I-A-36, I-A-100, I-A-101, I-A-155, I-A-199, I-A-250, I-A-252, I-A-360, I-A-379 and I-A-384 (c) I-A-36, I-A-100, I-A-101, I-A-155, I-A-199, I-A-238, I-A-250, I-A-252, I-A-357, I-A-360, I-A-379 and I-A-384 (d) I-A-36, I-A-100, I-A-199, I-A-238, I-A-250, I-A-252, I-A-381 and I-A-384 (e) I-A-36, I-A-100, I-A-101, I-A-199, I-A-200, I-A-238, I-A-250, I-A-252, I-A-357, I-A-360, I-A-379 and I-A-384 (f) I-A-36, I-A-101 and I-A-199

[0282] Test Example 8. Powdery mildew of barley The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the foliage of barley plants (variety: Kanto 6) at the one-leaf stage grown in a pot with a diameter of 5 cm. After the formulation had dried, the barley plants were inoculated by dusting with powdery mildew fungus of barley and kept in a greenhouse at 25 °C to promote the development of the disease. Seven days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0283] The results of the tests revealed that compounds I-A-2, I-A-3, I-A-4, I-A-5, I-A-10, I-A-13, I-A-16, I-A-25, I-A-35, I-A-36, I-A-43, I-A-55, I-A-56, I-A-63, I-A-71, I-A-77, I-A-79, I-A-95, I-A-97, I-A-99, I-A-100, I-A-103, I-A-127, I-A-132, I-A-133, I-A-135, I-A-139, I-A-147, I-A-148, I-A-152, I-A-155, I-A-167, I-A-169, I-A-190, I-A-192, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-217, I-A-218, I-A-219, I-A-220, I-A-222, I-A-226, I-A-238, I-A-239, I-A-246, I-A-250, I-A-251, I-A-252, I-A-254, I-A-255, I-A-256, I-A-257, I-A-259, I-A-260, I-A-261, I-A-262, I-A-264, I-A-265, I-A-266, I-A-269, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-277, I-A-278, I-A-279, I-A-280, I-A-281, I-A-283, I-A-286, I-A-288, I-A-289, I-A-290, I-A-291, I-A-292, I-A-293, I-A-294, I-A-295, I-A-296, I-A-299, I-A-300, I-A-301, I-A-302, I-A-304, I-A-346, I-A-347, I-A-348, I-A-351, I-A-352, I-A-353, I-A-355, I-A-357, I-A-358, I-A-359, I-A-361, I-A-363, I-A-370, I-A-379, I-A-383, I-A-384, I-A-387, I-A-388, I-A-389, I-A-390, I-A-391, I-A-392, I-A-393, I-A-394, I-A-398, I-A-400, I-A-401, I-A-403, I-A-404, I-A-405, I-A-407, I-A-408, I-A-409, I-A-410 at a concentration of 200 ppmI-A-411, I-A-413, I-A-414, I-A-416, I-A-417, I-A-420, I-A-421, I-A-422, I-A-436, I-A-440, I-A-474, I-A-475, I-A-480, I-A-485, I-A-488, I-A-492, I-A-524, I-A-525, I-A-527, I-A-530, I-A-558, I-A-576, I-A-577, I-A-606, I-A-619, I-B-2, I-C-2, I-C-5, I-C-15, I-C-16, I-C-17, I-C-18, I-C-26, I-C-27, I-C-28, I-K-7, I-K-8, I-K-9, I-K-10, I-K-13, I-K-14, I-K-15, I-K-16, I-K-17, I-K-18, I-K-19, I-K-20, I-K-22 and I-K-25 showed activity at level 1 or higher.

[0284] Test Example 9. Test of the control efficacy against wheat leaf blight The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the aerial parts of wheat plants at the ten-leaf stage grown in pots with a diameter of 6 cm. After the formulation had dried, the wheat plants were inoculated by spraying a spore suspension of the wheat leaf blight fungus. The wheat plants were kept at 15 °C under constant humidity conditions to allow the disease to develop. 16 days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0285] The results of the tests revealed that compounds I-A-5, I-A-37, I-A-39, I-A-75, I-A-81, I-A-89, I-A-94, I-A-106, I-A-124, I-A-132, I-A-135, I-A-139, I-A-152, I-A-159, I-A-175, I-A-196, I-A-206, I-A-218, I-A-220, I-A-222, I-A-239, I-A-250, I-A-253, I-A-264, I-A-269, I-A-287, I-A-289, I-A-290, I-A-291, I-A-349, I-A-355, I-A-359, I-A-386, I-A-390, I-A-392, I-A-410, I-A-432, I-A-433, I-A-434, I-A-444, I-A-520, I-A-524, I-A-525, I-A-542, I-A-545, I-A-546, I-A-561, I-A-562, I-A-563, I-A-572, I-A-574, I-A-578, I-A-589, I-A-591, I-A-595, I-A-596, I-A-608, I-A-609, I-A-619, I-A-621, I-A-622, I-A-624, I-A-635, I-A-636, I-A-637, I-C-15, I-C-17, I-K-13 and I-K-18 at a concentration of 200 ppm showed activity at level 1 or higher.

[0286] Test Example 10. Antifungal Activity Test The following (a), (b), (c), (d) and (e) were used as test fungi, and the mycelial growth inhibitory activity of each test compound was examined using PDA medium. After growth, the mycelial colony diameter was measured and the half-maximal effective concentration (EC 50 50 (a) Septoria tritici (b) Botrytis cinerea (c) Fusarium graminearum (d) Sclerotinia sclerotiorum (e) Cochliobolus miyabeanus

[0287] As a result of the above tests, the compounds with a half-maximal effective concentration of 200 ppm or less are listed below: (a) I-A-16, I-A-36, I-A-43, I-A-56, I-A-65, I-A-75, I-A-94, I-A-100, I-A-101, I-A-114, I-A-135, I-A-188, I-A-198, I-A-199, I-A-214, I-A-217, I-A-218, I-A-222, I-A-226, I-A-238, I-A-251, I-A-252, I-A-257, I-A-259, I-A-261, I-A-264, I-A-265, I-A-267, I-A-268, I-A-274, I-A-278, I-A-282, I-A-284, I-A-285, I-A-287, I-A-294, I-A-295, I-A-296, I-A-297, I-A-301, I-A-302 and I-A-378 (b) I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-10, I-A-13, I-A-16, I-A-17, I-A-25, I-A-35, I-A-36, I-A-37, I-A-38, I-A-39, I-A-41, I-A-43, I-A-49, I-A-52, I-A-54, I-A-55, I-A-56, I-A-58, I-A-59, I-A-62, I-A-63, I-A-64, I-A-65, I-A-68, I-A-70, I-A-71, I-A-75, I-A-77, I-A-78, I-A-79, I-A-80, I-A-89, I-A-94, I-A-98, I-A-99, I-A-100, I-A-101, I-A-102, I-A-106, I-A-113, I-A-114, I-A-123, I-A-125, I-A-127, I-A-132, I-A-133, I-A-135, I-A-138, I-A-139, I-A-148, I-A-152, I-A-154, I-A-155, I-A-157, I-A-159, I-A-165, I-A-167, I-A-168, I-A-169, I-A-171, I-A-172, I-A-173, I-A-175, I-A-178, I-A-180, I-A-186, I-A-192, I-A-195, I-A-196, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-217, I-A-218, I-A-220, I-A-222, I-A-226, I-A-238, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-255, I-A-256, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-276, I-A-277, I-A-278, I-A-279, I-A-281, I-A-282, I-A-283, I-A-284, I-A-285, I-A-286, I-A-288, I-A-289, I-A-290, I-A-293, I-A-294, I-A-295, I-A-296,I-A-297, I-A-298, I-A-299, I-A-300, I-A-301, I-A-302, I-A-303, I-A-304, I-A-346, I-A-348, I-A-349, I-A-350, I-A-352, I-A-353, I-A-357, I-A-360, I-A-362, I-A-363, I-A-366, I-A-368, I-A-370, I-A-372, I-A-375, I-A-376, I-A-378, I-A-379, I-A-381, I-A-384, I-C-2, I-C-13 and I-C-14, (c) I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-10, I-A-13, I-A-16, I-A-17, I-A-25, I-A-35, I-A-36, I-A-39, I-A-41, I-A-43, I-A-49, I-A-52, I-A-54, I-A-55, I-A-56, I-A-57, I-A-58, I-A-59, I-A-62, I-A-63, I-A-64, I-A-68, I-A-70, I-A-71, I-A-75, I-A-77, I-A-79, I-A-80, I-A-81, I-A-89, I-A-94, I-A-97, I-A-98, I-A-99, I-A-100, I-A-101, I-A-102, I-A-103, I-A-106, I-A-113, I-A-114, I-A-123, I-A-125, I-A-127, I-A-132, I-A-133, I-A-135, I-A-138, I-A-139, I-A-148, I-A-152, I-A-154, I-A-155, I-A-157, I-A-160, I-A-165, I-A-167, I-A-168, I-A-169, I-A-171, I-A-172, I-A-173, I-A-175, I-A-178, I-A-180, I-A-186, I-A-188, I-A-190, I-A-192, I-A-194, I-A-195, I-A-196, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-217, I-A-218, I-A-220, I-A-222, I-A-226, I-A-238, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-255, I-A-256, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-276, I-A-277, I-A-278, I-A-279, I-A-280, I-A-281, I-A-282, I-A-283, I-A-284, I-A-285, I-A-286, I-A-287, I-A-288, I-A-289,I-A-290, I-A-293, I-A-294, I-A-295, I-A-296, I-A-297, I-A-298, I-A-299, I-A-300, I-A-301, I-A-302, I-A-303, I-A-348, I-A-349, I-A-350, I-A-352, I-A-353, I-A-356, I-A-357, I-A-358, I-A-359, I-A-360, I-A-362, I-A-363, I-A-364, I-A-365, I-A-368, I-A-370, I-A-371, I-A-372, I-A-376, I-A-378, I-A-379, I-A-381, I-A-384, I-C-2, I-C-13 and I-C-14, (d) I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-10, I-A-13, I-A-16, I-A-17, I-A-25, I-A-35, I-A-36, I-A-37, I-A-38, I-A-39, I-A-40, I-A-41, I-A-43, I-A-49, I-A-52, I-A-54, I-A-55, I-A-56, I-A-57, I-A-58, I-A-59, I-A-62, I-A-63, I-A-64, I-A-65, I-A-68, I-A-70, I-A-71, I-A-75, I-A-76, I-A-77, I-A-78, I-A-79, I-A-80, I-A-81, I-A-82, I-A-89, I-A-94, I-A-95, I-A-97, I-A-98, I-A-99, I-A-100, I-A-101, I-A-102, I-A-103, I-A-106, I-A-113, I-A-114, I-A-123, I-A-125, I-A-127, I-A-130, I-A-131, I-A-132, I-A-133, I-A-135, I-A-138, I-A-139, I-A-148, I-A-152, I-A-154, I-A-155, I-A-157, I-A-159, I-A-160, I-A-162, I-A-163, I-A-165, I-A-167, I-A-168, I-A-169, I-A-171, I-A-172, I-A-173, I-A-175, I-A-178, I-A-180, I-A-186, I-A-192, I-A-194, I-A-195, I-A-196, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-217, I-A-218, I-A-219, I-A-220, I-A-222, I-A-226, I-A-238, I-A-239, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-255, I-A-256, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275, I-A-276, I-A-277,I-A-278, I-A-279, I-A-280, I-A-281, I-A-282, I-A-283, I-A-284, I-A-285, I-A-286, I-A-287, I-A-288, I-A-289, I-A-290, I-A-293, I-A-294, I-A-295, I-A-296, I-A-297, I-A-298, I-A-299, I-A-300, I-A-301, I-A-302, I-A-303, I-A-304, I-A-346, I-A-348, I-A-349, I-A-350, I-A-352, I-A-353, I-A-356, I-A-357, I-A-358, I-A-359, I-A-360, I-A-362, I-A-363, I-A-364, I-A-365, I-A-366, I-A-368, I-A-369, I-A-370, I-A-371, I-A-372, I-A-373, I-A-374, I-A-375, I-A-376, I-A-378, I-A-379, I-A-381, I-A-382, I-A-383, I-A-384, I-C-2, I-C-13 and I-C-14, (e) I-A-1, I-A-2, I-A-3, I-A-4, I-A-5, I-A-7, I-A-10, I-A-13, I-A-16, I-A-17, I-A-25, I-A-35, I-A-36, I-A-37, I-A-38, I-A-39, I-A-40, I-A-41, I-A-43, I-A-49, I-A-52, I-A-54, I-A-55, I-A-56, I-A-57, I-A-58, I-A-59, I-A-62, I-A-63, I-A-64, I-A-65, I-A-68, I-A-70, I-A-71, I-A-75, I-A-76, I-A-77, I-A-78, I-A-79, I-A-80, I-A-81, I-A-82, I-A-89, I-A-94, I-A-96, I-A-97, I-A-98, I-A-99, I-A-100, I-A-101, I-A-102, I-A-103, I-A-106, I-A-113, I-A-114, I-A-123, I-A-125, I-A-127, I-A-131, I-A-132, I-A-133, I-A-135, I-A-138, I-A-139, I-A-147, I-A-148, I-A-152, I-A-154, I-A-155, I-A-157, I-A-159, I-A-160, I-A-162, I-A-164, I-A-165, I-A-167, I-A-168, I-A-169, I-A-171, I-A-172, I-A-173, I-A-175, I-A-178, I-A-180, I-A-186, I-A-188, I-A-190, I-A-192, I-A-194, I-A-195, I-A-196, I-A-197, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-217, I-A-218, I-A-219, I-A-220, I-A-222, I-A-226, I-A-238, I-A-239, I-A-250, I-A-251, I-A-252, I-A-253, I-A-254, I-A-255, I-A-256, I-A-257, I-A-258, I-A-259, I-A-260, I-A-261, I-A-262, I-A-263, I-A-264, I-A-265, I-A-266, I-A-267, I-A-268, I-A-269, I-A-270, I-A-271, I-A-272, I-A-273, I-A-274, I-A-275,I-A-276, I-A-277, I-A-278, I-A-279, I-A-280, I-A-281, I-A-282, I-A-283, I-A-284, I-A-285, I-A-286, I-A-287, I-A-288, I-A-289, I-A-290, I-A-293, I-A-294, I-A-295, I-A-296, I-A-297, I-A-298, I-A-299, I-A-300, I-A-301, I-A-302, I-A-303, I-A-304, I-A-346, I-A-348, I-A-349, I-A-350, I-A-352, I-A-353, I-A-356, I-A-357, I-A-358, I-A-359, I-A-360, I-A-362, I-A-363, I-A-364, I-A-365, I-A-366, I-A-367, I-A-368, I-A-370, I-A-371, I-A-372, I-A-373, I-A-376, I-A-378, I-A-379, I-A-381, I-A-382, I-A-383, I-A-384, I-C-2, I-C-13 and I-C-14,

[0288] Test Example 11. Test on the control efficacy against Sclerotinia sclerotiorum of cucumbers The formulation prepared from the compound according to Formulation Example 1 of the present invention was diluted with water to a predetermined concentration. 10 ml of the diluted formulation was applied to the stems and leaves of cucumber plants (variety: YOTUBA) at the one-leaf stage grown in pots with a diameter of 9 cm. After the formulation had dried, 4-mm mycelial discs were prepared from the mycelia of the Sclerotinia sclerotiorum fungus of cucumbers. The cucumber plants were inoculated by placing the mycelial discs at the center of the leaves. The cucumber plants were maintained at 15°C under constant humidity conditions to allow the disease to develop. Five or six days after inoculation, the control efficacy was evaluated according to the criteria of Test Example 1.

[0289] The results of the tests revealed that compounds I-A-1, I-A-3, I-A-4, I-A-5, I-A-13, I-A-16, I-A-25, I-A-35, I-A-36, I-A-41, I-A-43, I-A-56, I-A-63, I-A-78, I-A-80, I-A-82, I-A-89, I-A-94, I-A-95, I-A-97, I-A-99, I-A-100, I-A-101, I-A-102, I-A-106, I-A-113, I-A-125, I-A-129, I-A-130, I-A-132, I-A-133, I-A-135, I-A-148, I-A-155, I-A-160, I-A-162, I-A-165, I-A-168, I-A-198, I-A-199, I-A-200, I-A-206, I-A-214, I-A-218, I-A-219, I-A-220, I-A-222, I-A-226, I-A-238, I-A-239, I-A-250, I-A-251, I-A-252, I-A-347, I-A-348, I-A-351, I-A-353, I-A-358, I-A-360, I-A-362, I-A-363, I-A-381, I-A-383, I-A-384, I-A-524, I-A-525, I-C-2, I-K-8, I-K-9, I-K-10, I-K-13, I-L-2 and I-L-3 at a concentration of 200 ppm showed activity at level 1 or higher. [Industrial Applicability]

[0290] The amide compounds of the present invention have the effect of controlling diseases that may infect cereals, fruit trees, vegetables, other crops and ornamental flowers, and can therefore be used as agricultural chemicals.

[0291] This application is based on Patent Application No. 2022-182306 filed on November 15, 2022 and Patent Application No. 2023-057006 filed on March 31, 2023, the contents of which are incorporated herein by reference in their entirety.

Claims

1. A compound represented by the general formula [I], or a salt thereof wherein R 1 and R 5 may be the same or different and each represents (a1) a hydrogen atom; (a2) a halogen atom; (a3) a cyano group; (a4) a nitro group; (a5) a hydroxyl group; (a6) a pentafluorothio group; (a7) a (C1-C6)alkyl group; (a8) a halo(C1-C6)alkyl group; (a9) a (C2-C6)alkenyl group; (a10) a halo(C2-C6)alkenyl group; (a11) a (C2-C6)alkynyl group; (a12) a halo(C2-C6)alkynyl group; (a13) a (C3-C6)cycloalkyl group; (a14) a (C3-C6)cycloalkenyl group; (a15) a halo(C3-C6)cycloalkyl group; (a16) a (C3-C6)cycloalkyl(C1-C6)alkyl group; (a17) a (C3-C6)cycloalkyl(C3-C6)cycloalkyl group; (a18) a halo(C3-C6)cycloalkyl(C1-C6)alkyl group; (a19) a halo(C3-C6)cycloalkyl halo(C1-C6)alkyl group; (a20) a cyano(C1-C6)alkyl group; (a21) a cyano(C3-C6)cycloalkyl group; (a22) a hydroxy(C1-C6)alkyl group; (a23) a (C1-C6)alkoxy(C1-C6)alkyl group; (a24) a halo(C1-C6)alkoxy(C1-C6)alkyl group; (a25) a (C3-C6)cycloalkoxy(C1-C6)alkyl group; (a26) a halo(C3-C6)cycloalkoxy(C1-C6)alkyl group; (a27) a (C1-C6)alkylthio(C1-C6)alkyl group; (a28) a halo(C1-C6)alkylthio(C1-C6)alkyl group; (a29) a (C1-C6)alkylthio halo(C1-C6)alkyl group; (a30) a (C1-C6)alkylsulfinyl(C1-C6)alkyl group; (a31) a halo(C1-C6)alkylsulfinyl(C1-C6)alkyl group; (a32) a (C1-C6)alkylsulfinyl halo(C1-C6)alkyl group; (a33) a (C1-C6)alkylsulfonyl(C1-C6)alkyl group; (a34) a halo(C1-C6)alkylsulfonyl(C1-C6)alkyl group; (a35) a (C1-C6)alkylsulfonyl halo(C1-C6)alkyl group; (a36) a (C1-C6)alkoxy(C2-C6)alkenyl group; (a37) a (C1-C6)alkoxy(C2-C6)alkynyl group; (a38) a (C1-C10)alkoxy group; (a39) a halo(C1-C10)alkoxy group; (a40) a (C2-C6)alkenyloxy group; (a41) a halo(C2-C6)alkenyloxy group; (a42) a (C2-C6)alkynyloxy group; (a43) a halo(C2-C6)alkynyloxy group; (a44) a (C3-C7)cycloalkoxy group; (a45) a (C3-C6)cycloalkyl(C1-C6)alkoxy group; (a46) a (C1-C6)alkoxy(C1-C6)alkoxy group; (a47) a (C1-C6)alkylcarbonyloxy group; (a48) a (C3-C6)cycloalkylcarbonyloxy group; (a49)(C3-C6) cycloalkenyl; (a50)(C1-C6) alkylthio; (a51) halo(C1-C6) alkylthio; (a52)(C1-C6) alkylsulfinyl; (a53) halo(C1-C6) alkylsulfinyl; (a54)(C1-C6) alkylsulfonyl; (a55) halo(C1-C6) alkylsulfonyl; (a56) Z group; (a57) Z(C1-C6) alkyl; (a58) Z(C1-C6) alkoxy; (a59) Z halo(C1-C6) alkoxy; (a60) Z(C2-C6) alkenyl; (a61) Z halo(C2-C6) alkenyl; (a62) Z(C2-C6) alkynyl; (a63) Z halo(C2-C6) alkynyl; (a64) Z(C3-C6) cycloalkyl; (a65) Z halo(C3-C6) cycloalkyl; (a66) Z carbonyl oxy; (a67) Z(C1-C6) alkylthio; (a68) N-mono-Z(C1-C6) alkylamino; (a69) N-(C1-C6) alkyl-N-Z(C1-C6) alkylamino; (a70) N-Z(C1-C6) alkyl-N-Z(C1-C6) alkylamino; (a71) Z oxy; (a72) Z sulfonylamino; (a73) Z thio; (a74) Z sulfinyl; (a75) Z sulfonyl; (a76) Z carbonylamino; (a77) N-((C1-C6) alkyl)-N-(Z carbonyl) amino; (a78) N-mono-(C1-C6) alkoxycarbonylamino; (a79) N-((C1-C6) alkoxycarbonyl)-N-((C1-C6) alkyl) amino; (a80) N-(C1-C6) alkyl-N-Z aminocarbonyl; (a81) Z carbonyl; (a82) Z(C1-C6) alkylcarbonylamino; (a83) Z amino; (a84) amino; (a85) N-mono-(C1-C6) alkylamino; (a86) N-(C1-C6) alkyl-N-(C1-C6) alkylamino; (a87) N-mono-(C2-C6) alkenylamino; (a88) N-(C2-C6) alkenyl-N-(C2-C6) alkenylamino; (a89) N-mono-(C2-C6) alkynylamino; (a90) N-(C2-C6) alkynyl-N-(C2-C6) alkynylamino; (a91)(C1-C6) alkylcarbonylamino; (a92)(C3-C6) cycloalkylcarbonylamino; (a93) aminothio; (a94) aminosulfinyl; (a95) aminosulfonyl; (a96) N-mono-(C1-C6) alkylaminothio; (a97) N-(C1-C6) alkyl-N-(C1-C6) alkylaminothio; (a98) N-mono-(C1-C6) alkylaminosulfinyl; (a99)N-(C1-C6)alkyl-N-(C1-C6)alkylaminosulfinyl; (a100)N-mono-(C1-C6)alkylaminosulfonyl; (a101)N-(C1-C6)alkyl-N-(C1-C6)alkylaminosulfonyl; (a102)aminocarbonyl; (a103)N-mono-(C1-C6)alkylaminocarbonyl; (a104)N-(C1-C6)alkyl-N-(C1-C6)alkylaminocarbonyl; (a105)(C1-C6)alkylcarbonyl; (a106)(C3-C6)cycloalkylcarbonyl; (a107)(C1-C6)alkoxycarbonyl; (a108)aminooxy; (a109)hydroxyamino; (a110)(C3-C6)cycloalkoxycarbonyl; (a111)formyl; (a112)carboxy; (a113)oxo; (a114)(C1-C12)alkylsilyl; (a115)halo(C3-C6)cycloalkoxy; (a116)Z-halo(C1-C6)alkyl; (a117)N-Z-aminosulfonyl; (a118)Z,Z-(C1-C6)alkoxy; (a119)(C1-C6)alkoxy(C1-C6)alkoxy(C1-C6)alkoxy; (a120)N-((C1-C6)alkoxycarbonyl)-N-Z-amino; (a121)(C3-C6)cycloalkoxy; (a122)halo(C1-C6)alkylcarbonylamino; (a123)(C3-C6)cycloalkylamino; (a124)Z-aminocarbonyl; (a125)(C3-C6)cycloalkylaminocarbonyl; or (a126)a group represented by formula A1, A2, A3, A4 or A5 Z represents (b1)phenyl; (b2)A substituted phenyl group having, on the ring, 1 to 5 substituents independently selected from the group consisting of: a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C2-C6)alkenyl group, a halo(C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyloxy group, a halo(C2-C6)alkenyloxy group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfonyloxy group, a halo(C1-C6)alkylsulfonyloxy group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, a (C2-C6)alkenylthio group, a halo(C2-C6)alkenylthio group, a (C2-C6)alkenylsulfinyl group, a halo(C2-C6)alkenylsulfinyl group, a (C2-C6)alkenylsulfonyl group, a halo(C2-C6)alkenylsulfonyl group, an N-mono-(C1-C6)alkylamino group, an N,N-di-(C1-C6)alkylamino group in which the alkyl groups may be the same or different, a (C1-C6)alkylsulfonylamino group, a halo(C1-C6)alkylsulfonylamino group, a (C1-C6)alkylcarbonyl group, a formyl group, a halo(C1-C6)alkylcarbonyl group, a hydroxy(C1-C6)alkyl group, a (C1-C6)alkoxycarbonyl group, an aminocarbonyl group, a (C1-C12)alkylsilyl group, a phenoxy group and a phenyl group; (b3)A heterocyclic group; (b4)A heterocyclic group having, on the ring, 1 to 3 substituents independently selected from the group consisting of: a halogen atom, a hydroxyl group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkoxy group, a (C1-C6)alkylthio group, a halo(C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group and a (C1-C6)alkoxycarbonyl group; (b5)A naphthyl group; (b6)An indanyl group; or (b7)An indenyl group, R 2 and R 3 may be the same or different and each represents (c1)(C1-C6) alkyl; or (c2)A halogen atom, R4 represents (d1)A hydrogen atom; (d2)A (C1-C6)alkyl group; (d3)A halo(C1-C6)alkyl group; (d4)A (C1-C6)alkoxy group; (d5)A halo(C1-C6)alkoxy group; (d6)A (C2-C6)alkenyl group; (d7)A (C2-C6)alkynyl group; (d8)A (C3-C6)cycloalkyl group; (d9)A (C3-C6)cycloalkyl(C1-C6)alkyl group; (d10)A (C1-C6)alkoxy(C1-C6)alkyl group; (d11)A (C1-C6)alkylcarbonyl group; (d12)A (C1-C6)alkoxycarbonyl group; (d13)A (C3-C6)cycloalkylcarbonyl group; (d14) (C1-C6) alkoxy (C1-C6) alkylcarbonyl; (d15) halo (C1-C6) alkylcarbonyl; (d16) (C1-C6) alkoxycarbonyl (C1-C6) alkyl; (d17) amino (C1-C6) alkylcarbonyl; (d18) N-mono-(C1-C6) alkylamino (C1-C6) alkylcarbonyl; (d19) N,N-di-(C1-C6) alkylamino (C1-C6) alkylcarbonyl; (d20) (C1-C6) alkylthio; (d21) halo (C1-C6) alkylthio; (d22) (C1-C6) alkylsulfinyl; (d23) halo (C1-C6) alkylsulfinyl; (d24) (C1-C6) alkylsulfonyl; (d25) halo (C1-C6) alkylsulfonyl; (d26) (C3-C6) cycloalkylthio; (d27) (C3-C6) cycloalkylsulfinyl; (d28) (C3-C6) cycloalkylsulfonyl; (d29) amino (C1-C6) alkyl; (d30) N-mono-(C1-C6) alkylamino (C1-C6) alkyl; (d31) N,N-di-(C1-C6) alkylamino (C1-C6) alkyl; (d32) Z(C1-C6) alkyl; (d33) Z group; (d34) Z oxy; (d35) Z carbonyl; (d36) (C2-C6) alkenyloxycarbonyl; (d37) (C2-C6) alkynyloxycarbonyl; (d38) (C2-C6) alkenylcarbonyl; (d39) amino (C1-C6) alkylcarbonyl; (d40) N-mono-(C1-C6) alkylamino (C1-C6) alkylcarbonyl; (d41) N,N-di-(C1-C6) alkylamino (C1-C6) alkylcarbonyl; (d42) Z(C1-C6) alkylcarbonyl; or (d43) Z(C1-C6) alkoxycarbonyl, Two Rs 1 can be bonded to each other to form a ring structure represented by the formula R 1-1 , R 1-2 , R 1-3 or R 1-4 , each ring structure containing the carbon atoms to which they are bonded Two Rs 5 may be bonded to each other to form a ring structure represented by the formula R 5-1 or R 5-2 each ring structure containing the carbon atoms to which they are bonded R 4 and R 5 can bond to each other to form a ring structure containing a partial structure represented by the following formula R 4-5-1 or R 4-5-2 and the carbon and nitrogen atoms to which they are bonded X represents an oxygen atom or a sulfur atom, Ar 1 represents phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, thiazolyl or a group represented by Formula #1, #2 or #3 Ar 2 represents a group represented by the formula: Ar 2-1 、Ar 2-2 、Ar 2-3 、Ar 2-4 、Ar 2-5 、Ar 2-6 、Ar 2-7 、Ar 2-8 、Ar 2-9 、Ar 2 -10 、Ar 2-11 、Ar 2-12 、Ar 2-13 、Ar 2-14 、Ar 2-15 、Ar 2-16 、Ar 2-17 、Ar 2-18 、Ar 2-19 、Ar 2-20 、Ar 2-21 、Ar 2-22 or Ar 2-23 m represents 1, 2, 3, 4 or 5, and n represents 1, 2, 3, 4 or 5, Provided that it does not include the compound represented by the following formula DC1 and its salts 2. The compound or its salt according to claim 1, wherein, R 1 and R 5 may be the same or different and each is (a1) a hydrogen atom; (a2) halogen atom; (a3) cyano; (a4) nitro; (a5) hydroxy; (a7) (C1-C6) alkyl; (a8) halo (C1-C6) alkyl; (a9) (C2-C6) alkenyl; (a10) halo (C2-C6) alkenyl; (a11) (C2-C6) alkynyl; (a12) halo (C2-C6) alkynyl; (a13) (C3-C6) cycloalkyl; (a14) (C3-C6) cycloalkenyl; (a15) halo (C3-C6) cycloalkyl; (a16) (C3-C6) cycloalkyl (C1-C6) alkyl; (a17) (C3-C6) cycloalkyl (C3-C6) cycloalkyl; (a22) hydroxy (C1-C6) alkyl; (a23) (C1-C6) alkoxy (C1-C6) alkyl; (a24) halo (C1-C6) alkoxy (C1-C6) alkyl; (a25) (C3-C6) cycloalkyloxy(C1-C6)alkyl; (a26) halo(C3-C6)cycloalkyloxy(C1-C6)alkyl; (a27) (C1-C6)alkylthio(C1-C6)alkyl; (a36) (C1-C6)alkoxy(C2-C6)alkenyl; (a37) (C1-C6)alkoxy(C2-C6)alkynyl; (a38) (C1-C10)alkoxy; (a39) halo(C1-C10)alkoxy; (a40) (C2-C6)alkenyloxy; (a41) halo(C2-C6)alkenyloxy; (a42) (C2-C6)alkynyloxy; (a43) halo(C2-C6)alkynyloxy; (a44) (C3-C7)cycloalkoxy; (a45) (C3-C6)cycloalkyl(C1-C6)alkoxy; (a46) (C1-C6)alkoxy(C1-C6)alkoxy; (a47) (C1-C6)alkylcarbonyloxy; (a48) (C3-C6)cycloalkylcarbonyloxy; (a49) (C3-C6)cycloalkenyl; (a50) (C1-C6)alkylthio; (a51) halo(C1-C6)alkylthio; (a52) (C1-C6)alkylsulfinyl; (a53) halo(C1-C6)alkylsulfinyl; (a54) (C1-C6)alkylsulfonyl; (a55) halo(C1-C6)alkylsulfonyl; (a56) Z group; (a57) Z(C1-C6)alkyl; (a58) Z(C1-C6)alkoxy; (a59) Z halo(C1-C6)alkoxy; (a62) Z(C2-C6)alkynyl; (a66) Zcarbonyloxy; (a67) Z(C1-C6)alkylthio; (a68) N-mono-Z(C1-C6)alkylamino; (a69) N-(C1-C6)alkyl-N-Z(C1-C6)alkylamino; (a70) N-Z(C1-C6)alkyl-N-Z(C1-C6)alkylamino; (a71) Zoxy; (a72) Zsulfonylamino; (a73) Zthio; (a74) Zsulfinyl; (a75) Zsulfonyl; (a76) Zcarbonylamino; (a77) N-((C1-C6)alkyl)-N-(Zcarbonyl)amino; (a78) N-mono-(C1-C6)alkoxycarbonylamino; (a79) N-((C1-C6)alkoxycarbonyl)-N-((C1-C6)alkyl)amino; (a80) N-(C1-C6)alkyl-N-Zaminocarbonyl; (a81) Zcarbonyl; (a82) Z(C1-C6)alkylcarbonylamino; (a83) Zamino; (a84) amino; (a85) N-mono-(C1-C6)alkylamino; (a86) N-(C1-C6)alkyl-N-(C1-C6)alkylamino; (a87) N-mono-(C2-C6)alkenylamino; (a88) N-(C2-C6)alkenyl-N-(C2-C6)alkenylamino; (a89)N-Mono-(C2-C6)alkynylamino; (a90)N-(C2-C6)alkynyl-N-(C2-C6)alkynylamino; (a91)(C1-C6)alkylcarbonylamino; (a92)(C3-C6)cycloalkylcarbonylamino; (a93)Aminosulfanyl; (a94)Aminosulfinyl; (a95)Aminosulfonyl; (a96)N-Mono-(C1-C6)alkylaminosulfanyl; (a97)N-(C1-C6)alkyl-N-(C1-C6)alkylaminosulfanyl; (a98)N-Mono-(C1-C6)alkylaminosulfinyl; (a99)N-(C1-C6)alkyl-N-(C1-C6)alkylaminosulfinyl; (a100)N-Mono-(C1-C6)alkylaminosulfonyl; (a101)N-(C1-C6)alkyl-N-(C1-C6)alkylaminosulfonyl; (a102)Aminocarbonyl; (a103)N-Mono-(C1-C6)alkylaminocarbonyl; (a104)N-(C1-C6)alkyl-N-(C1-C6)alkylaminocarbonyl; (a105)(C1-C6)alkylcarbonyl; (a106)(C3-C6)cycloalkylcarbonyl; (a107)(C1-C6)alkoxycarbonyl; (a108)Aminoxy; (a109)Hydroxyamino; (a110)(C3-C6)cycloalkoxycarbonyl; (a111)Formyl; (a112)Carboxy; (a113)Oxo; (a114)(C1-C12)alkylsilyl; (a120)N-((C1-C6)alkoxycarbonyl)-N-Zamino; (a121)(C3-C6)cycloalkoxy; (a122)Halogenated (C1-C6)alkylcarbonylamino; (a123)(C3-C6)cycloalkylamino; (a124)Zaminocarbonyl; (a125)(C3-C6)cycloalkylaminocarbonyl; or A group represented by the following formula A1, A2, A3, A4 or A5 R 2 and R 3 may be the same or different and each is a halogen atom, and R 4 is (d1)Hydrogen atom; (d2)(C1-C6)alkyl; (d4)(C1-C6)alkoxy; (d6)(C2-C6)alkenyl; (d9)(C3-C6)cycloalkyl(C1-C6)alkyl; (d10)(C1-C6)alkoxy(C1-C6)alkyl; (d11)(C1-C6)alkylcarbonyl; (d12)(C1-C6)alkoxycarbonyl; (d14)(C1-C6)alkoxy(C1-C6)alkylcarbonyl; (d16)(C1-C6)alkoxycarbonyl(C1-C6)alkyl; (d20)(C1-C6)alkylsulfanyl; (d22)(C1-C6)alkylsulfinyl; (d24)(C1-C6)alkylsulfonyl; (d28)(C3-C6)cycloalkylsulfonyl; (d29)Amino(C1-C6)alkyl; (d30)N-Mono-(C1-C6)alkylamino(C1-C6)alkyl; (d31)N,N-Di-(C1-C6)alkylamino(C1-C6)alkyl; (d32)Z(C1-C6)alkyl; (d33)Z group; (d35)Z carbonyl; (d36)(C2-C6) alkenyloxycarbonyl; (d37)(C2-C6) alkynyloxycarbonyl; (d38)(C2-C6) alkenylcarbonyl; (d39) amino (C1-C6) alkylcarbonyl; (d40) N-mono-(C1-C6) alkylamino (C1-C6) alkylcarbonyl; or (d41) N,N-di-(C1-C6) alkylamino (C1-C6) alkylcarbonyl, R 4 and R 5 can bond to each other to form a ring structure containing a partial structure represented by the following formula R 4-5-1 and the carbon and nitrogen atoms to which they are bonded and Ar 2 is a group represented by the formula: Ar 2-1 、Ar 2-2 、Ar 2-3 、Ar 2-4 、Ar 2-5 、Ar 2-6 、Ar 2-7 、Ar 2-8 、Ar 2-9 、Ar 2-10 、Ar 2-11 、Ar 2-12 、Ar 2-13 、Ar 2-14 、Ar 2-17 、Ar 2-18 、Ar 2-19 or Ar 2-20 3. The compound or its salt according to claim 2, wherein, R 1 and R 5 may be the same or different and each is (a1) a hydrogen atom; (a2) halogen atom; (a3) cyano; (a4) nitro; (a5) hydroxy; (a7)(C1-C6) alkyl; (a8) halo (C1-C6) alkyl; (a9)(C2-C6) alkenyl; (a11)(C2-C6) alkynyl; (a13)(C3-C6) cycloalkyl; (a14)(C3-C6) cycloalkenyl; (a22) hydroxy (C1-C6) alkyl; (a36)(C1-C6) alkoxy (C2-C6) alkenyl; (a38)(C1-C10) alkoxy; (a39) halo (C1-C10) alkoxy; (a40)(C2-C6) alkenyloxy; (a44)(C3-C7) cycloalkyloxy; (a45)(C3-C6) cycloalkyl (C1-C6) alkoxy; (a46)(C1-C6) alkoxy (C1-C6) alkoxy; (a47)(C1-C6) alkylcarbonyloxy; (a48)(C3-C6) cycloalkylcarbonyloxy; (a50)(C1-C6) alkylthio; (a51) halo (C1-C6) alkylthio; (a52)(C1-C6) alkylsulfinyl; (a54)(C1-C6) alkylsulfonyl; (a56)Z group; (a57)Z(C1-C6) alkyl; (a58)Z(C1-C6) alkoxy; (a62)Z(C2-C6) alkynyl; (a66)Z carbonyloxy; (a67)Z(C1-C6) alkylthio; (a68)N-mono-Z(C1-C6) alkylamino; (a69)N-(C1-C6) alkyl-N-Z(C1-C6) alkylamino; (a70)N-Z(C1-C6) alkyl-N-Z(C1-C6) alkylamino; (a71)Z oxy; (a72)Z sulfonylamino; (a76)Z carbonylamino; (a77)N-((C1-C6) alkyl)-N-(Z carbonyl) amino; (a78)N-mono-(C1-C6) alkoxycarbonylamino; (a79)N-((C1-C6) alkoxycarbonyl)-N-((C1-C6) alkyl) amino; (a81)Z carbonyl; (a82)Z(C1-C6) alkylcarbonylamino; (a83)Z amino; (a84) amino; (a85)N-mono-(C1-C6) alkylamino; (a86)N-(C1-C6) alkyl-N-(C1-C6) alkylamino; (a87)N-mono-(C2-C6) alkenylamino; (a91)(C1-C6) alkylcarbonylamino; (a92) (C3-C6) cycloalkylcarbonylamino; (a95) Sulfamoyl; (a100) N-mono-(C1-C6) alkylsulfamoyl; (a101) N-(C1-C6) alkyl-N-(C1-C6) alkylsulfamoyl; (a102) Aminocarbonyl; (a103) N-mono-(C1-C6) alkylaminocarbonyl; (a104) N-(C1-C6) alkyl-N-(C1-C6) alkylaminocarbonyl; (a105) (C1-C6) alkylcarbonyl; (a106) (C3-C6) cycloalkylcarbonyl; (a107) (C1-C6) alkoxycarbonyl; (a111) Formyl; (a112) Carboxyl; (a113) Oxo group; (a114) (C1-C12) alkylsilyl; (a120) N-((C1-C6) alkoxycarbonyl)-N-Z amino; (a121) (C3-C6) cycloalkoxy; (a122) Halo(C1-C6) alkylcarbonylamino; (a123) (C3-C6) cycloalkylamino; (a124) Z aminocarbonyl; (a125) (C3-C6) cycloalkylaminocarbonyl; or (a126) A group represented by formula A1, A2, A3, A4 or A5 R 4 is (d1) Hydrogen atom; (d2) (C1-C6) alkyl; (d4) (C1-C6) alkoxy; (d6) (C2-C6) alkenyl; (d10) (C1-C6) alkoxy(C1-C6) alkyl; (d11) (C1-C6) alkylcarbonyl; (d12) (C1-C6) alkoxycarbonyl; (d14) (C1-C6) alkoxy(C1-C6) alkylcarbonyl; (d16) (C1-C6) alkoxycarbonyl(C1-C6) alkyl; (d22) (C1-C6) alkylsulfinyl; (d24) (C1-C6) alkylsulfonyl; (d28) (C3-C6) cycloalkylsulfonyl; (d31) N,N-di-(C1-C6) alkylamino(C1-C6) alkyl; (d32) Z(C1-C6) alkyl; (d36) (C2-C6) alkenyloxycarbonyl; (d38) (C2-C6) alkenylcarbonyl; (d39) Amino(C1-C6) alkylcarbonyl; or (d41) N,N-di-(C1-C6) alkylamino(C1-C6) alkylcarbonyl, and X is an oxygen atom.

4. An agricultural and horticultural fungicide comprising the compound according to claim 1 or a salt thereof as an active ingredient.

5. An agricultural and horticultural fungicide comprising the compound according to claim 2 or a salt thereof as an active ingredient.

6. An agricultural and horticultural fungicide comprising the compound according to claim 3 or a salt thereof as an active ingredient.

7. A method for controlling agricultural and horticultural diseases, which comprises treating plants or soil with an effective amount of the agricultural and horticultural fungicide according to claim 4.

8. A method for controlling agricultural and horticultural diseases, the method comprising treating a plant or soil with an effective amount of the agricultural and horticultural fungicide according to claim 5.

9. A method for controlling agricultural and horticultural diseases, the method comprising treating a plant or soil with an effective amount of the agricultural and horticultural fungicide according to claim 6.

10. Use of the compound or its salt according to claim 1 as a fungicide.

11. Use of the compound or its salt according to claim 2 as a fungicide.

12. Use of the compound or its salt according to claim 3 as a fungicide.

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