OXADIAZOLINE COMPOUNDS OR SALTS THEREOF, AGROHORTICULTURAL FUNGICIDES CONTAINING THE COMPOUNDS, AND METHODS OF USING THE SAME

Abstract

In production of crops of agriculture and horticulture or the like, damage caused by diseases is still large, and, due to factors such as occurrence of resistant diseases to existing drugs, development of new agrohorticultural fungicides is desired.

The present invention provides an agrohorticultural fungicide and a method of use thereof of, an active ingredient thereof being a compound represented by the general formula (I) or salts thereof:

##STR00001##

{wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 denote a hydrogen atom or the like, A, B, Y, denote a single bond or carbonyl group or the like, Q denotes a (C.sub.1-C.sub.6)alkyl group or hetero ring or the like, R.sup.5 and R.sup.6 denote a hydrogen atom or (C.sub.1-C.sub.6)alkyl group or the like.}.

Claims

1-6. (canceled)

7. A compound represented by the general formula (I) or salts thereof: ##STR00557## wherein: A is a single bond or the following structure A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5, A.sup.6, or A.sup.7: ##STR00558## B is a single bond, an oxygen atom, C(R.sup.1)(R.sup.2), or a carbonyl group; Y is a single bond, an oxygen atom, C(R.sup.1)(R.sup.2), or N(R.sup.3); R.sup.1 and R.sup.2 are each independently: (a1) a hydrogen atom; (a2) a halogen atom; (a3) a (C.sub.1-C.sub.6)alkyl group; (a4) a (C.sub.1-C.sub.6)alkoxy group; or (a5) a halo(C.sub.1-C.sub.6)alkyl group; or R.sup.1 and R.sup.2 form a cyclopropyl group with a carbon atom to which they bond; R.sup.3 is: (b1) a hydrogen atom; (b2) a (C.sub.1-C.sub.6)alkyl group; (b3) a (C.sub.1-C.sub.6)alkoxy group; (b4) a (C.sub.3-C.sub.6)cycloalkyl group; (b5) a (C.sub.1-C.sub.6)alkylcarbonyl group; (b6) a (C.sub.1-C.sub.6)alkoxycarbonyl group; (b7) a (C.sub.2-C.sub.6)alkenyl group; (b8) a (C.sub.2-C.sub.6)alkynyl group; or (b9) a (C.sub.3-C.sub.6)cycloalkyl(C.sub.1-C.sub.6)alkyl group; Q is: (c1) a hydrogen atom; (c2) a (C.sub.1-C.sub.6)alkyl group; (c3) a (C.sub.2-C.sub.6)alkenyl group; (c4) a (C.sub.2-C.sub.6)alkynyl group; (c5) a (C.sub.3-C.sub.6)cycloalkyl group; (c6) a (C.sub.1-C.sub.6)alkoxy group; (c7) a halo(C.sub.1-C.sub.6)alkyl group; (c8) a halo(C.sub.2-C.sub.6)alkenyl group; (c9) a halo(C.sub.2-C.sub.6)alkynyl group; (c10) a halo(C.sub.3-C.sub.5)cycloalkyl group; (c11) a halo(C.sub.1-C.sub.6)alkoxy group; (c12) an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are each independently a hydrogen atom, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.2-C.sub.6)alkenyl group, a (C.sub.2-C.sub.6)alkynyl group, a (C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.1-C.sub.6)alkyl group, a (C.sub.3-C.sub.6)cycloalkyl(C.sub.1-C.sub.6)alkyl group, a phenyl group, a (C.sub.1-C.sub.6)alkoxy(C.sub.1-C.sub.6)alkyl group, a di(C.sub.1-C.sub.6)alkoxy(C.sub.1-C.sub.6)alkyl group, a cyano(C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, a di(C.sub.1-C.sub.6)alkylamino(C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkylcarbonyl group, a (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkyl group, a phenylcarbonyl group, or a benzyl group; (c13) an aryl group; (c14) an aryl group, independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkoxy group, a (C.sub.3-C.sub.6)cycloalkyl group, a halo(C.sub.1-C.sub.6)alkyl group, a halo(C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, a (C.sub.1-C.sub.6)alkylsulfonyl group, a halo(C.sub.1-C.sub.6)alkylthio group, a halo(C.sub.1-C.sub.6)alkylsulfinyl group, a halo(C.sub.1-C.sub.6)alkylsulfonyl group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkoxycarbonyl group, and R.sup.a(R.sup.b)N carbonyl group (wherein R.sup.a and R.sup.b are the same as above); (c15) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring; (c16) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C.sub.1-C.sub.6)alkyl group, (C.sub.1-C.sub.6)alkoxy group, (C.sub.3-C.sub.6)cycloalkyl group, halo(C.sub.1-C.sub.6)alkyl group, halo(C.sub.1-C.sub.6)alkoxy group, halo(C.sub.3-C.sub.6)cycloalkyl group, (C.sub.1-C.sub.6)alkylthio group, (C.sub.1-C.sub.6)alkylsulfinyl group, (C.sub.1-C.sub.6)alkylsulfonyl group, halo(C.sub.1-C.sub.6)alkylthio group, halo(C.sub.1-C.sub.6)alkylsulfinyl group, halo(C.sub.1-C.sub.6)alkylsulfonyl group, R.sup.a(R.sup.b)N group (wherein R.sup.a and R.sup.b are the same as above), (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C.sub.1-C.sub.6)alkoxycarbonyl group and R.sup.a(R.sup.b)N carbonyl group (wherein R.sup.a and R.sup.b are the same as above); (c17) an aryl (C.sub.1-C.sub.6)alkyl group; (c18) an aryl (C.sub.1-C.sub.6)alkyl group, each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C.sub.1-C.sub.6)alkyl group, (C.sub.1-C.sub.6)alkoxy group, (C.sub.3-C.sub.6)cycloalkyl group, halo(C.sub.1-C.sub.6)alkyl group, halo(C.sub.1-C.sub.6)alkoxy group, halo(C.sub.3-C.sub.6)cycloalkyl group, (C.sub.1-C.sub.6)alkylthio group, (C.sub.1-C.sub.6)alkylsulfinyl group, (C.sub.1-C.sub.6)alkylsulfonyl group, halo(C.sub.1-C.sub.6)alkylthio group, halo(C.sub.1-C.sub.6)alkylsulfinyl group, halo(C.sub.1-C.sub.6)alkylsulfonyl group, R.sup.a(R.sup.b)N group (wherein R.sup.a and R.sup.b are the same as above), (C.sub.1-C.sub.6)alkoxycarbonyl group, and R.sup.a(R.sup.b)N carbonyl group, wherein R.sup.a and R.sup.b are the same as above; (c19) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C.sub.1-C.sub.6)alkyl group; (c20) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C.sub.1-C.sub.6)alkyl group, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkoxy group, a (C.sub.3-C.sub.6)cycloalkyl group, a halo(C.sub.1-C.sub.6)alkyl group, a halo(C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, a (C.sub.1-C.sub.6)alkylsulfonyl group, a halo(C.sub.1-C.sub.6)alkylthio group, a halo(C.sub.1-C.sub.6)alkylsulfinyl group, a halo(C.sub.1-C.sub.6)alkylsulfonyl group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, a phenyl group, a halogen-substituted phenoxy group, a (C.sub.1-C.sub.6)alkoxycarbonyl group, and an R.sup.a(R.sup.b)N carbonyl group, wherein R.sup.a and R.sup.b are the same as above; (c21) a (C.sub.1-C.sub.6)alkyl group, each independently having on the chain 1 to 3 substituents selected from the group consisting of a cyano group, a (C.sub.1-C.sub.6)alkoxy group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, and a (C.sub.1-C.sub.6)alkylsulfonyl group; (c22) an R.sup.cON═C(R.sup.d)NH group, wherein R.sup.c and R.sup.d are each independently a hydrogen atom or a (C.sub.1-C.sub.6)alkyl group); or (c23) a 3-ethoxyiminoazetidin-1-yl group; R.sup.5 is: (d1) a hydrogen atom; (d2) a (C.sub.1-C.sub.6)alkyl group; (d3) a (C.sub.1-C.sub.6)alkylcarbonyl group; (d4) a (C.sub.1-C.sub.6)alkoxycarbonyl group; or (d5) a benzyl group; R.sup.6 is: (e1) a hydrogen atom; and X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently: (f1) a hydrogen atom; (f2) a halogen atom; (f3) a cyano group; (f4) a nitro group; (f5) a (C.sub.1-C.sub.6)alkyl group; (f6) a (C.sub.3-C.sub.6)cycloalkyl group; (f7) a (C.sub.1-C.sub.6)alkoxy group; (f8) a halo(C.sub.1-C.sub.6)alkyl group; (f9) a halo(C.sub.1-C.sub.6)alkoxy group; (f10) a halo(C.sub.3-C.sub.6)cycloalkyl group; (f11) a (C.sub.1-C.sub.6)alkylthio group; (f12) a (C.sub.1-C.sub.6)alkylsulfinyl group; (f13) a (C.sub.1-C.sub.6)alkylsulfonyl group; (f14) a halo(C.sub.1-C.sub.6)alkylthio group; (f15) a halo(C.sub.1-C.sub.6)alkylsulfinyl group; or (f16) a halo(C.sub.1-C.sub.6)alkylsulfonyl group.

8. The compound according to claim 7 or salts thereof, wherein: A is a single bond or the following structure A.sup.1, A.sup.2, A.sup.5, A.sup.6, or A.sup.7: ##STR00559## R.sup.1 and R.sup.2 are each independently: (a1) a hydrogen atom; (a2) a halogen atom; or (a4) a (C.sub.1-C.sub.6)alkoxy group; R.sup.3 is: (b1) a hydrogen atom; (b2) a (C.sub.1-C.sub.6)alkyl group; (b3) a (C.sub.1-C.sub.6)alkoxy group; (b4) a (C.sub.3-C.sub.6)cycloalkyl group; (b7) a (C.sub.2-C.sub.6)alkenyl group; (b8) a (C.sub.2-C.sub.6)alkynyl group; or (b9) a (C.sub.3-C.sub.6)cycloalkyl(C.sub.1-C.sub.6)alkyl group; Q is: (c1) a hydrogen atom; (c2) a (C.sub.1-C.sub.6)alkyl group; (c5) a (C.sub.3-C.sub.6)cycloalkyl group; (c6) a (C.sub.1-C.sub.6)alkoxy group; (c7) a halo(C.sub.1-C.sub.6)alkyl group; (c12) an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are each independently a hydrogen atom, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.2-C.sub.6)alkenyl group, a (C.sub.2-C.sub.6)alkynyl group, a (C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.1-C.sub.6)alkyl group, a (C.sub.3-C.sub.6)cycloalkyl(C.sub.1-C.sub.6)alkyl group, a phenyl group, a (C.sub.1-C.sub.6)alkoxy(C.sub.1-C.sub.6)alkyl group, a di(C.sub.1-C.sub.6)alkoxy(C.sub.1-C.sub.6)alkyl group, a cyano(C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, a di(C.sub.1-C.sub.6)alkylamino(C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkylcarbonyl group, a (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkyl group, a phenylcarbonyl group, or a benzyl group; (c14) an aryl group, independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkoxy group, a (C.sub.3-C.sub.6)cycloalkyl group, a halo(C.sub.1-C.sub.6)alkyl group, a halo(C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, a (C.sub.1-C.sub.6)alkylsulfonyl group, a halo(C.sub.1-C.sub.6)alkylthio group, a halo(C.sub.1-C.sub.6)alkylsulfinyl group, a halo(C.sub.1-C.sub.6)alkylsulfonyl group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkoxycarbonyl group, and an R.sup.a(R.sup.b)N carbonyl group, wherein R.sup.a and R.sup.b are the same as above; (c15) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring; (c16) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C.sub.1-C.sub.6)alkyl group, (C.sub.1-C.sub.6)alkoxy group, (C.sub.3-C.sub.6)cycloalkyl group, halo(C.sub.1-C.sub.6)alkyl group, halo(C.sub.1-C.sub.6)alkoxy group, halo(C.sub.3-C.sub.6)cycloalkyl group, (C.sub.1-C.sub.6)alkylthio group, (C.sub.1-C.sub.6)alkylsulfinyl group, (C.sub.1-C.sub.6)alkylsulfonyl group, halo(C.sub.1-C.sub.6)alkylthio group, halo(C.sub.1-C.sub.6)alkylsulfinyl group, halo(C.sub.1-C.sub.6)alkylsulfonyl group, R.sup.a(R.sup.b)N group (wherein R.sup.a and R.sup.b are the same as above), (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C.sub.1-C.sub.6)alkoxycarbonyl group and R.sup.a(R.sup.b)N carbonyl group (wherein R.sup.a and R.sup.b are the same as above); (c19) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C.sub.1-C.sub.6)alkyl group; (c20) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C.sub.1-C.sub.6)alkyl group, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C.sub.1-C.sub.6)alkyl group, (C.sub.1-C.sub.6)alkoxy group, (C.sub.3-C.sub.6)cycloalkyl group, halo(C.sub.1-C.sub.6)alkyl group, halo(C.sub.1-C.sub.6)alkoxy group, halo(C.sub.3-C.sub.6)cycloalkyl group, (C.sub.1-C.sub.6)alkylthio group, (C.sub.1-C.sub.6)alkylsulfinyl group, (C.sub.1-C.sub.6)alkylsulfonyl group, halo(C.sub.1-C.sub.6)alkylthio group, halo(C.sub.1-C.sub.6)alkylsulfinyl group, halo(C.sub.1-C.sub.6)alkylsulfonyl group, R.sup.a(R.sup.b)N group (wherein R.sup.a and R.sup.b are the same as above), (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C.sub.1-C.sub.6)alkoxycarbonyl group and R.sup.a(R.sup.b)N carbonyl group (wherein R.sup.a and R.sup.b are the same as above); (c21) a (C.sub.1-C.sub.6)alkyl group, each independently having on the chain 1 to 3 substituents selected from the group consisting of a cyano group, (C.sub.1-C.sub.6)alkoxy group, R.sup.a(R.sup.b)N group (wherein R.sup.a and R.sup.b are the same as above), (C.sub.1-C.sub.6)alkylthio group, (C.sub.1-C.sub.6)alkylsulfinyl group and (C.sub.1-C.sub.6)alkylsulfonyl group; (c22) an R.sup.cON═C(R.sup.d)NH group (wherein R.sup.c and R.sup.d each independently denote a hydrogen atom or (C.sub.1-C.sub.6)alkyl group); or (c23) a 3-ethoxyiminoazetidin-1-yl group, R.sup.5 is: (d1) a hydrogen atom; (d2) a (C.sub.1-C.sub.6)alkyl group; or (d5) a benzyl group; and X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are: (f1) a hydrogen atom.

9. The compound according to claim 7 or salts thereof, wherein: R.sup.1 and R.sup.2 are each independently: (a1) a hydrogen atom; or (a4) a (C.sub.1-C.sub.6)alkoxy group; R.sup.3 is: (b1) a hydrogen atom; (b2) a (C.sub.1-C.sub.6)alkyl group; or (b3) a (C.sub.1-C.sub.6)alkoxy group; and Q is: (c1) a hydrogen atom; (c2) a (C.sub.1-C.sub.6)alkyl group; (c5) a (C.sub.3-C.sub.6)cycloalkyl group; (c6) a (C.sub.1-C.sub.6)alkoxy group; (c7) a halo(C.sub.1-C.sub.6)alkyl group; (c12) an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are each independently a hydrogen atom, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.2-C.sub.6)alkenyl group, a (C.sub.2-C.sub.6)alkynyl group, a (C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.1-C.sub.6)alkyl group, a (C.sub.3-C.sub.6)cycloalkyl(C.sub.1-C.sub.6)alkyl group, a phenyl group, a (C.sub.1-C.sub.6)alkoxy(C.sub.1-C.sub.6)alkyl group, a di(C.sub.1-C.sub.6)alkoxy(C.sub.1-C.sub.6)alkyl group, a cyano(C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, a di(C.sub.1-C.sub.6)alkylamino(C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkylcarbonyl group, a (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkyl group, a phenylcarbonyl group, or a benzyl group; (c14) an aryl group, independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkoxy group, a (C.sub.3-C.sub.6)cycloalkyl group, a halo(C.sub.1-C.sub.6)alkyl group, a halo(C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, a (C.sub.1-C.sub.6)alkylsulfonyl group, a halo(C.sub.1-C.sub.6)alkylthio group, a halo(C.sub.1-C.sub.6)alkylsulfinyl group, a halo(C.sub.1-C.sub.6)alkylsulfonyl group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkoxycarbonyl group, and an R.sup.a(R.sup.b)N carbonyl group, wherein R.sup.a and R.sup.b are the same as above; (c15) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring; (c16) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkoxy group, a (C.sub.3-C.sub.6)cycloalkyl group, a halo(C.sub.1-C.sub.6)alkyl group, a halo(C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, a (C.sub.1-C.sub.6)alkylsulfonyl group, a halo(C.sub.1-C.sub.6)alkylthio group, a halo(C.sub.1-C.sub.6)alkylsulfinyl group, a halo(C.sub.1-C.sub.6)alkylsulfonyl group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, a phenyl group, a halogen-substituted phenoxy group, a (C.sub.1-C.sub.6)alkoxycarbonyl group, and an R.sup.a(R.sup.b)N carbonyl group, wherein R.sup.a and R.sup.b are the same as above; (c19) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C.sub.1-C.sub.6)alkyl group; (c20) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C.sub.1-C.sub.6)alkyl group, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C.sub.1-C.sub.6)alkyl group, a (C.sub.1-C.sub.6)alkoxy group, a (C.sub.3-C.sub.6)cycloalkyl group, a halo(C.sub.1-C.sub.6)alkyl group, a halo(C.sub.1-C.sub.6)alkoxy group, a halo(C.sub.3-C.sub.6)cycloalkyl group, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, a (C.sub.1-C.sub.6)alkylsulfonyl group, a halo(C.sub.1-C.sub.6)alkylthio group, a halo(C.sub.1-C.sub.6)alkylsulfinyl group, a halo(C.sub.1-C.sub.6)alkylsulfonyl group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkylthio(C.sub.1-C.sub.6)alkyl group, a phenyl group, a halogen-substituted phenoxy group, a (C.sub.1-C.sub.6)alkoxycarbonyl group, and an R.sup.a(R.sup.b)N carbonyl group, wherein R.sup.a and R.sup.b are the same as above; or (c21) a (C.sub.1-C.sub.6)alkyl group, each independently having on the chain 1 to 3 substituents selected from the group consisting of a cyano group, a (C.sub.1-C.sub.6)alkoxy group, an R.sup.a(R.sup.b)N group, wherein R.sup.a and R.sup.b are the same as above, a (C.sub.1-C.sub.6)alkylthio group, a (C.sub.1-C.sub.6)alkylsulfinyl group, and a (C.sub.1-C.sub.6)alkylsulfonyl group.

10. A fungicide comprising an active ingredient selected from the compound according to claim 7 or salts thereof.

11. A method of controlling plant disease, comprising the administration of an effective amount of the fungicide according to claim 10 to a plant or soil in need thereof.

12. Use of the compound according to claim 7 or salts thereof as a fungicide.

Description

EXAMPLES

Production Example 1

Production of N-methyl-N-{4-[5-(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]benzyl}methansulfoneamide (Compound No. 1-1)

[0122] ##STR00550##

[0123] N-methyl-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}methane sulfone amide (0.30 g, 0.90 mmol) prepared by the method described in WO 2017/213252 pamphlet was dissolved in methanol (10 ml), cooled to 0° C., sodium borohydride (0.017 g, 0.45 mmol) was added and stirred at room temperature for 1.5 hours. Thereafter, 1 ml of acetone was added, and the mixture was stirred at room temperature for 15 minutes, added with silica gel, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.23 g, 0.67 mmol).

[0124] Yield: 75%

[0125] Physical property: Melting point 160-161° C.

Production Example 2

Production of N-methyl-N-{4-[4-methyl-5-(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]benzyl}methansulfoneamide (Compound No. 1-13)

[0126] ##STR00551##

[0127] N-methyl-N-{4-[5-(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]benzyl}methane sulfonamide (0.060 g, 0.018 mmol) was dissolved in DMA (3 ml), cesium carbonate (0.087 g, 0.27 mmol) and methyl iodide (0.038 g, 0.27 mmol) were added at room temperature and stirred at room temperature for 3.4 hours. It was cooled to 0° C., quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.046 g, 0.13 mmol).

[0128] Yield: 73%

[0129] Physical property: 107-109° C.

Production Example 3

Production of N-methyl-N-{4-[5-methyl-5-(trifluoromethyl)-4,5-dihydro-1,2,4-oxadiazol-3-yl]benzyl}butylamide (Compound No. 1-12)

[0130] ##STR00552##

[0131] N-Methyl-N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butylamide (0.12 g, 0.36 mmol) prepared by the method described in WO 2017/055469 pamphlet was dissolve in dry THF (3 ml) under argon atmosphere, cool to 0° C., methylmagnesium bromide (3.0 M in Et.sub.2O) (0.18 ml, 0.55 mmol) was added, and the mixture was stirred at room temperature for 1.7 hours. After that, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.077 g, 0.22 mmol).

[0132] Yield: 62%

[0133] Physical property: Melting point 161-163° C.

Reference Example 1

Production of 5-chloro-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}pyridin-2(1H)-one

[0134] ##STR00553##

[0135] 3-[4-(Bromomethyl) phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (0.25 g, 0.81 mmol) prepared by the method described in WO 2017/118689 pamphlet was dissolved in DMA (2 ml) and potassium carbonate (0.17 g, 1.21 mmol) and 5-chloro-2-hydroxypyridine (0.125 g, 0.97 mmol) were added at room temperature and stirred for 1.5 hours at 100° C. It was cooled to 0° C., quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (0.112 g, 0.32 mmol).

[0136] Yield: 39%

Reference Example 2

Production of (Z)—N′-hydroxy-4-iodobenzimidate

[0137] ##STR00554##

[0138] 4-iodobenzonitrile (11 g, 64 mmol) was dissolved in 70 mL of ethanol, sodium acetate (5.6 g, 68 mmol) and hydroxylamine hydrochloride (4.7 g, 68 mmol) were added, and the mixture was stirred for 4 hours while heating under reflux. Ethanol was removed thereafter, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure. The precipitated solid was washed with ethyl acetate:hexane=10:1. To remove ethyl acetate, the obtained solid was dried under reduced pressure at 40° C. for 1 hour using a sample drier and allowed to stand for 1 day to obtain the title compound (12 g) as a crude product.

[0139] Yield: quantitative

Reference Example 3

Production of 3-(4-iodophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

[0140] ##STR00555##

[0141] (Z)—N′-hydroxy-4-iodobenzimidate (12 g, 45 mmol) was dissolved in 100 mL of chloroform, pyridine (14 g, 180 mmol), trifluoroacetic anhydride (19 g, 90 mmol) were added, and stirred for 5 hours at room temperature. Thereafter, water was added and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (11 g, 31 mmol).

[0142] Yield: 43%

[0143] Physical property: Melting point 73-75° C.

Reference Example 4

Production of N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl}butylamide

[0144] ##STR00556##

[0145] 3-(4-iodophenyl)-5- (trifluoromethyl)-1,2,4-oxadiazole (0.31 g, 0.90 mmol) was dissolved in 8 mL of toluene, cesium carbonate (0.44 g, 1.4 mmol), n-Butylamide (0.094 g, 1.1 mmol), xanthophos (0.16 g, 0.27 mmol), tris (dibenzylideneacetone)dipalladium (0) (0.084 g, 0.090 mmol) were added at room temperature, and the mixture was heated to reflux for 2.5 hours. The residue was purified by silica gel column chromatography to obtain the title compound (0.19 g, 0.62 mmol).

[0146] Yield: 69%

[0147] Physical property value: Melting point 112-115° C.

[0148] The following recite examples of present inventive formulations. In the formulation examples, the term “parts” denotes “parts by weight”.

Formulation Example 1

[0149]

TABLE-US-00054 Present inventive compound represented by the general formula (I) 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts

[0150] An emulsifiable concentrate was prepared by uniformly mixing and dissolving the above ingredients.

Formulation Example 2

[0151]

TABLE-US-00055 Present inventive compound represented by the general formula (I)  3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts

[0152] A dust was prepared by mixing uniformly and grinding the above ingredients.

Formulation Example 3

[0153]

TABLE-US-00056 Present inventive compound represented by the general formula (I)  5 parts Mixed powder of bentonite and clay 90 parts Calcium lignin sulfonate 5 parts

[0154] Granules were prepared by mixing the above ingredients uniformly together with a suitable amount of water, and kneading the resulting mixture, followed by granulation and drying.

Formulation Example 4

[0155]

TABLE-US-00057 Present inventive compound represented by the general formula (I) 20 parts Mixture of kaolin and synthetic high-dispersion silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate  5 parts

[0156] A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Test Example 1. Fungicidal Efficacy Test for Soybean Rust

[0157] A chemical agent prepared according to Formulation Examples 1 to 4 containing the present inventive compound represented by the general formula (I) as an active ingredient was diluted with water to a predetermined concentration. Soybeans (cultivar: Enrei, 2-leaf stage) grown in pots of 6 cm in diameter were foliage sprayed at a rate of 10 ml per pot. After air-drying the solution, the spore suspension prepared from spores obtained from soybean leaves infected with soybean rust (Phakopsora pachyrhizi) was spray-inoculated, kept at 20° C. humidified conditions for 24 hours, and then transferred to a greenhouse to be left about 10 days.

[0158] For evaluation, various diseased area ratios were assessed to calculate the control value from the following formula 1.

[00001]$\begin{array}{cc}\mathrm{Control}\mathrm{value}\left(\%\right)=\frac{\begin{array}{c}\mathrm{Average}\mathrm{lesion}\mathrm{area}\mathrm{ratio}\mathrm{in}\mathrm{untreated}\mathrm{plot}-\\ \mathrm{Average}\mathrm{lesion}\mathrm{area}\mathrm{ratio}\mathrm{in}\mathrm{treated}\mathrm{plot}\end{array}}{\mathrm{Average}\mathrm{lesion}\mathrm{area}\mathrm{ratio}\mathrm{in}\mathrm{untreated}\mathrm{plot}}\times 100& \left[\mathrm{Formula}1\right]\end{array}$

Assessment Criteria

[0159] 0: Control value 9% or lower

[0160] 1: Control value 10-19%

[0161] 2: Control value 20-29%

[0162] 3: Control value 30-39%

[0163] 4: Control value 40-49%

[0164] 5: Control value 50-59%

[0165] 6: Control value 60-69%

[0166] 7: Control value 70-79%

[0167] 8: Control value 80-89%

[0168] 9: Control value 90-99%

[0169] 10: Control value 100%

[0170] As the result of the above mentioned test, of the present inventive compounds represented by the general formula (I), the following compounds showed, at the treatment concentration of 50 ppm, an effect with a control value of 8 or higher: 1-1, 1-5, 1-9, 1-10, 1-11, 1-12, 1-14, 1-15, 1-19, 1-23, 1-27, 1-28, 1-31, 1-35, 1-39, 1-40, 1-43, 1-47, 1-53, 1-54, 1-55, 1-56, 1-58, 1-63, 1-64, 1-65, 1-69, 1-73, 1-74, 1-76, 1-80, 1-81, 1-82, 1-90, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-8, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 2-18, 2-20, 2-21, 2-22, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-28, 3-29, 3-30, 3-32, 3-35, 3-36, 3-38, 3-39, 3-40, 3-41, 3-42, 3-43, 3-44, 3-45, 3-46, 3-53, 3-55, 4-3, 5-3, 6-3, 6-6 and 6-9.

Test Example 4. HDAC4 Inhibitory Activity Measurement Test

<Objective>

[0171] The HDAC inhibitory activity of the present compounds is evaluated in comparison with known compounds.

<Materials and Methods (Test Compound and Concentration)>

[0172] The test substances were diluted with distilled water, and the concentration was set as follows: Each compound had a maximum concentration of 37.5 μM, and a total of 6 concentrations at a common ratio of 3 (0.2, 0.5, 1.4, 4.2, 12.5, 37.5 μM) were provided. The positive control agent Tricostatin A was tested at a maximum concentration of 25 μM with reference to the package insert, and a total of 4 concentrations at a common ratio of 5 (0.2, 1.0, 5.0, 25 μM) were tested. Distilled water was added to the solvent control instead of the test substances.

[0173] The fluorogenic HDAC4 assay kit (BPS Bioscience, Cat No. 50064) was used for HDAC4 inhibitory activity measurement. Specific amounts of HDAC substrate, Assay buffer, HDAC4 human recombinant enzyme and BSA (1 mg/ml) provided in the kit were mixed and aliquoted into 96 well microplates. After adding a test substance solution (distilled water for solvent control), the mixture was incubated at 37° C. for 30 minutes. After adding 2× HDAC Developer and incubating for 15 minutes at room temperature, the fluorescence intensity was measured with a microplate reader (Em: 355, Ex: 450). The ratio to the solvent control (Percent of control activity) was determined as the relative activity, and the relative activity at each concentration was used to calculate the 50% inhibitory concentration (IC.sub.50) by logistic regression analysis.

<Result>

[0174] The compounds of the present invention were found to have an IC.sub.50 of 36.8 or higher, and turned out to tend to have lower HDAC4 inhibitory activity.

INDUSTRIAL APPLICABILITY

[0175] The present inventive compound represented by the general formula (I) or salts thereof has a remarkable effect as an agrohorticultural fungicide.