Novel Dithiolane Compound Or A Salt Or An N Oxide And Use Thereof
Abstract:
An object of the present invention is to provide a dithiolane compound or a salt or an N-oxide thereof that controls diseases. The present invention provides a dithiolane compound represented by Formula (1) or a salt or an N-oxide thereof wherein R1 represents hydrogen halogen C1-6 alkyl or a substituent as defined herein; R2 represents hydrogen halogen C1-6 alkyl or a substituent as defined herein; R3 represents hydrogen halogen C1-6 alkyl or a substituent as defined herein; Y1 represents optionally substituted aryl optionally substituted pyridyl or a substituent as defined herein; Y2 represents optionally substituted aryl optionally substituted pyridyl or a substituent as defined herein; Q represents cyano or a substituent as defined herein.
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Notices, Deadlines & Correspondence
The present invention relates to a novel dithiolane compound or a salt or an N-oxide and a process for preparing the same. The invention further provides an agricultural and horticultural fungicide composition comprising the said compounds .
Background Art
In recent years, for the protection of plants against diseases caused by fungi, various known fungicides are being used. However, due to long term and heavy use of these fungicides, development of resistance in various fungi has been observed. As a result, the control of drug resistant fungi could not be accomplished by the use of known
fungicides. Consequently, there is a demand for the
development of new types of compounds having a fungicidal activity against drug resistant fungi.
WO 2015/003991 (Patent Literature (PTL) 1) discloses the compounds represented by the formula (A) :
(A)
wherein, X is 0, S or NR4; Y and Z are independently O, S, NR5 or C(R6R7); A is hydrogen, alkyl, haloalkyl, cycloalkyl, halocycloalkyl , aryl, heteroaryl, various electron-withdrawing groups like, nitro, cyano, acetyl, carboxy, or the like; Q is alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, heterocyclic group, or the like; R1, R2 and R3 are independently hydrogen, halogen, Ci_6 alkyl, Ci_6 haloalkyl, C3_7 cycloalkyl, Ci_6 alkoxy, Ci-6 haloalkoxy, or optionally substituted phenyl. The
publication also mentioned that the compounds represented by the Formula (A) are useful as fungicide to control plant diseases .
Patent literature WO 2015/162271 (Patent Literature (PTL) 2) and WO 2015/162269 (Patent Literature (PTL) 3) also disclose imidazole substituted compounds represented by the Formula (B) :
wherein, X and Y are independently 0, S or NR5; R1 , R2 and R4 are independently hydrogen, halogen, Ci-6 alkyl, Ci_6 haloalkyl, Ci-6 cycloalkyl, Ci-6 alkoxy, Ci-6 haloalkoxy; R3 is phenyl, which is substituted by at least one substituent R6 or an aromatic five-membered heterocycles; and R5 is hydrogen, Ci_6 alkyl, alkoxy, or Ci_6 cycloalkyl .
The publications also mentioned that the compounds
represented by the Formula (B) are useful as fungicide to control plant diseases. However, these publications nowhere disclose the compounds of the present invention.
Further Patent literature WO 2015/162268 (Patent
Literature (PTL) 4) also disclosed imidazole substituted compounds represented by the Formula (C) :
wherein, X and Y are independently 0, S or NR4; R1, R2 and R3 are independently hydrogen, halogen, CX-6 alkyl, Ci-6 haloalkyl, C -6 alkoxy, Ci-6 haloalkoxy Z1, Z2, Z3, Z4 and Z5 are
independently CR5 or N.
The publication also mentioned that the compounds represented by the Formula (C) are useful as fungicide to control plant diseases. However, this publication nowhere discloses the compounds of the present invention.
Citation List
Patent Literature
PTL 1: WO 2015/003991
PTL 2: WO 2015/162271
PTL 3: WO 2015/162269
PTL 4: WO 2015/162268
Summary of Invention
Solution to Problem
The present invention provides novel dithiolane compound or a salt or an N-oxide which exhibit excellent fungicidal activity against drug resistant fungi as well as drug
sensitive fungi.
The present invention also provides a process for preparing the said dithiolane compound or a salt or an N-oxide.
The present invention further provides a new type of fungicide for agriculture and horticulture which exhibits a remarkable fungicidal effect against chemical-resistant fungi as well as chemical-sensitive fungi.
Specifically the present inventors conducted extensive research, and succeeded in synthesizing a compound represented by the following Formula (1) or a salt or an N-oxide thereof that has fungicidal activity. The present inventors have conducted further research based on the above findings. The present invention has ;thereby been accomplished.
More specifically, the present invention includes the following embodiments:
Item 1:
A dithiolane compound represented by Formula (1)
or a salt or an N-oxide thereof,
wherein R1, R2 and R3 are identical or different and each represents hydrogen, halogen, Ci-6 alkyl, Ci_6 haloalkyl, Ci_6 alkoxy, Ci-e haloalkoxy, Ci-6 alkoxy Ci_6 alkyl, Ci-6 haloalkoxy Ci_6 alkyl, C2-6 alkenyl, C2_6 haloalkenyl, C2_6 alkynyl, C2_6 haloalkynyl, C3-8 cycloalkyl, C3-8 cycloalkyl Ci-6 alkyl, optionally substituted aryl, optionally substituted
heteroaryl, or optionally substituted heterocyclic group, two of R1, R2 and R3 groups, taken together, may form a ring, via or not via at least one heteroatom, the groups represented as R1, R2, and R3 may optionally be further substituted;
Y1 represents optionally substituted aryl, optionally substituted pyridyl, optionally substituted pyrazinyl, optionally substituted pyrimidinyl or optionally substituted pyridazinyl ;
Y2 represents optionally substituted aryl or optionally substituted heteroaryl; and
Q represents hydrogen, nitro, cyano, Ci_6 alkyl, Ci_6 haloalkyl, C3-8 cycloalkyl, C3-8 cycloalkyl Ci_6 alkyl, Ci_6 alkylcarbonyl , Ci_6 haloalkylcarbonyl , C3-8 cycloal kylcarbonyl , Ci-6 alkoxycarbonyl , Ci_6 haloalkoxycarbonyl , C3_8
cycloalkoxycarbonyl , Ci_6 alkylthio, Ci_6 haloalkylthio, C3-8 cycloalkylthio, C3_8 cycloalkyl Ci-6 alkylthio, Ci-6 alkoxy Ci-6 alkylthio, Ci-6 alkylsulfonyl , Ci_6 alkylsulfinyl, Ci_6
haloalkylsulfonyl , Ci_6 haloalkylsulfinyl , C3_g
cycloalkylsulfonyl , C3-8 cycloalkylsulfinyl, C3_8 cycloalkyl Ci_6 alkylsulfonyl , C3-8 cycloalkyl Ci-6 alkylsulfinyl, optionally substituted arylthio, optionally substituted aryl Ci_6
alkylthio, optionally substituted arylsulfonyl , optionally substituted arylsulfinyl , optionally substituted aryl,
optionally substituted heteroaryl, or optionally substituted heterocyclic group.
Item 2:
The dithiolane compound or a salt or an N-oxide thereof according to Item 1, wherein R1, R2 and R3 are identical or different and each represents hydrogen, halogen, or Ci_6 alkyl.
Item 3:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein R1, R2 and R3 are identical or different and each represents hydrogen or Ci-6 alkyl.
Item 4:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y1 is optionally substituted aryl or optionally substituted pyridyl Item 5:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y1 is a phenyl ring represented by Yla:
wherein R4, R5, R6, R7 and R8 are identical or different and each represents hydrogen, halogen, nitro, cyano, hydroxyl, formyl, optionally substituted amino, Ci-6 alkyl, Ci_6
haloalkyl, Ci_6 alkoxy, Ci-6 haloalkoxy, Ci-6 alkoxy Ci-6 alkyl, Ci_6 haloalkoxy Ci_6 alkyl, Ci-6 alkoxycarbonyl , Ci_s
haloalkoxycarbonyl , cyano Ci-6 alkyl, cyano C]-6 alkoxy, C2-e alkenyl, C2_6 haloalkenyl, cyano C2-6 alkenyl, C2-6 alkynyl, C2-6 haloalkynyl, cyano C2-6 alkynyl, C3-8 cycloalkyl, C3-8 cycloalkyl C -6 alkyl, Ci-6 alkylthio, Ci-6 haloalkylthio, C3-8
cycloalkylthio, C3_8 cycloalkyl Ci-6 alkylthio, Ci_5 alkoxy Ci-6 alkylthio, Ci-6 alkylsulfonyl , Ci_6 alkylsulfinyl , Ci_6
haloalkylsulfonyl, Ci^6 haloalkylsulfinyl, C3_8
cycloalkylsulfonyl , C3-8 cycloalkylsulfinyl , C3_8 cycloalkyl, Ci 6 alkylsulfonyl , C3_8 cycloalkyl Ci_6 alkylsulfinyl , C2~6
alkenyloxy, C2_6 alkynyloxy, C2-6 haloalkenyloxy, C2-e
haloalkynyloxy , Ci~e alkylsulfonyloxy, Ci_6 alkylsulfinyloxy, Cj 6 alkylcarbonyl , Ci-6 haloalkylcarbonyl , carboxyl, OCN, SCN, SF5, optionally substituted aryloxy, optionally substituted aryl Ci-6 alkoxy, optionally substituted arylthio, optionally substituted aryl Ci_6 alkylthio, optionally substituted arylsulfonyl , optionally substituted arylsulfinyl , optionally substituted heteroaryloxy, optionally substituted
arylsulfonyloxy, optionally substituted arylsulfinyloxy, optionally substituted aryl, optionally substituted
heteroaryl, or optionally substituted heterocyclic group; and the * is the point of attachment to the parent compound.
Item 6:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, R4, R5, R6, R; and R8 are identical or different and each represents hydrogen, halogen, Ci_6 alkyl, Ci-6 haloalkyl, Ci-6 alkoxy or Ci_6
haloalkoxy .
Item 7 :
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y1 is optionally substituted 4-pyridyl, optionally substituted 3-pyridyl, or optionally substituted 2-pyridyl.
Item 8:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y1 is a pyridine ring represented by any one of Ylb, Ylc and Yld:
wherein R9, R10, R11, R12, R13, R14 , R15, R16, R17, R18 , R19, and R: are identical or different and each represents hydrogen, halogen, nitro, cyano, hydroxyl, formyl, optionally
substituted amino, Ci_6 alkyl, Ci_6 haloalkyl, CX-6 alkoxy, C1-6 haloalkoxy, Ci_6 alkoxy Ci_6 alkyl, Ci_6 haloalkoxy Ci_6 alkyl, Ci-6 alkoxycarbonyl , Ci-6 haloalkoxycarbonyl, cyano Ci_6 alkyl, cyano Ci-6 alkoxy, C2-6 alkenyl, C2-6 haloalkenyl, cyano C2~6 alkenyl, C2-6 alkynyl, C2~6 haloalkynyl, cyano C2_6 alkynyl, C3-8 cycloalkyl, C3-8 cycloalkyl Ci_6 alkyl, Ci^6 alkylthio, Ci-6 haloalkylthio, C3-8 cycloalkylthio, C3-8 cycloalkyl Ci_6 alkylthio, Ci_6 alkoxy Ci_6 alkylthio, Ci_6 alkylsulfonyl , Ci_6 alkylsulfinyl, Ci_6 haloalkylsulfonyl , Ci_6 haloalkylsulfinyl , C3-8 cycloalkylsulfonyl , C3_8 cycloalkvlsulfinyl, C3_8
cycloalkyl, Ci-6 alkylsulfonyl , C3_8 cycloalkyl d-6
alkylsulfinyl , C2_6 alkenyloxy, C2_6 alkynyloxy, C2_6
haloalkenyloxy, C _6 haloalkynyloxy, Ci_6 alkylsulfonyloxy, Ci_6 alkylsulfinyloxy, Ci_6 alkylcarbonyl , Ci-6 haloalkylcarbonyl , carboxyl, OCN, SCN, SF5, optionally substituted aryloxy,
optionally substituted aryl Ci_6 alkoxy, optionally substituted arylthio, optionally substituted aryl Ci-6 alkylthio,
optionally substituted arylsulfonyl , optionally substituted arylsulfinyl, optionally substituted heteroaryloxy, optionally substituted arylsulfonyloxy, optionally substituted
arylsulfinyloxy, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted heterocyclic group; and
the * is the point of attachment to the parent compound.
Item 9:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19,and R20 are identical or different and each represents hydrogen or halogen.
Item 10:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y1 represents:
wherein the * is the point of attachment to the parent compound .
Item 11:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y1 represents :
wherein the * is the point of attachment to the parent compound.
Item 12:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y1 represents :
wherein the * is the point of attachment to the parent compound .
Item 13:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is optionally substituted aryl.
Item 14:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is a phenyl ring represented by Y2a:
( The Y 2a )
wherein R , R , R , R , and R are identical or
different and each represents hydrogen, halogen, nitro, cyano, hydroxyl, formyl, optionally substituted amino, Ci-6 alkyl, Ci_ haloalkyl, Ci-6 alkoxy, Ci_6 haloalkoxy, Ci_6 alkoxy Ci_6 alkyl, Ci-6 haloalkoxy Ci-6 alkyl, Ci-6 alkoxycarbonyl, Ci_6
haloalkoxycarbonyl, cyano Ci-6 alkyl, cyano Ci_6 alkoxy, C2-6 alkenyl, C2_6 haloalkenyl , cyano C2_6 alkenyl, C2-6 alkynyl, C2-6 haloalkynyl, cyano C2~e alkynyl, C3-8 cycloalkyl, C3_8 cycloalkyl Ci-6 alkyl, Ci_6 alkylthio, Ci_6 haloalkylthio, C3-8
cycloalkylthio, C3-8 cycloalkyl Ci-6 alkylthio, Ci_6 alkoxy Ci-6 alkylthio, Ci-6 alkylsulfonyl, Ci_6 alkylsulfinyl , Ci_6
haloalkylsulfonyl , Ci-6 haloalkylsulf inyl, C3_8
cycloalkylsulfonyl , C3_8 cycloalkylsulfinyl, C3-8 cycloalkyl, Ci 6 alkylsulfonyl, C3-8 cycloalkyl Ci-6 alkylsulfinyl, C2-6
alkenyloxy, C2-6 alkynyloxy, C2_6 haloalkenyloxy, C2_6
haloal kynyloxy , Ci-6 alkylsulfonyloxy, Ci-6 alkylsulfinyloxy, Ci 6 alkylcarbonyl, C 6 haloalkylcarbonyl , carboxyl, OCN, SCN, SF5, optionally substituted aryloxy, optionally substituted aryl Ci-6 alkoxy, optionally substituted arylthio, optionally substituted aryl Ci-6 alkylthio, optionally substituted
arylsulfonyl, optionally substituted arylsulfinyl , optionally substituted heteroaryloxy, optionally substituted
arylsulfonyloxy, optionally substituted arylsulfinyloxy, optionally substituted aryl, optionally substituted
heteroaryl, or optionally substituted heterocyclic group; and the * is the point of attachment to the parent compound.
Item 15:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein R21, R22, R23, R24, and R25 are identical or different and each represents hydrogen, halogen, nitro, cyano, optionally substituted amino, Ci-g alkyl, Ci-6 haloalkyl, Ci-6 alkoxy, C 6 haloalkoxy, or optionally substituted aryl.
Item 16:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is optionally substituted heteroaryl.
Item 17:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is optionally substituted pyridyl, optionally substituted
pyrazinyl, optionally substituted pyrimidinyl, optionally substituted pyridazinyl or optionally substituted thiazolyl.
Item 18:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is optionally substituted pyridyl, optionally substituted pyrazinyl, or optionally substituted thiazolyl.
Item 19:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is optionally substituted pyridyl.
Item 20:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is optionally substituted 4-pyridyl, optionally substituted 3-pyridyl, or optionally substituted 2-pyridyl.
Item 21:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is a pyridine ring represented by any one of Y2b, Y2c and Y2d:
and R are identical or different and each represents
hydrogen, halogen, nitro, cyano, hydroxyl, formyl, optionally substituted amino, Ci_6 alkyl, Ci-6 haloalkyl, Ci-6 alkoxy, Ci-6 haloalkoxy, Ci_6 alkoxy Ci-6 alkyl, Ci-6 haloalkoxy Ci-6 alkyl, Ci_ 6 al koxycarbonyl , Ci_6 haloalkoxycarbonyl , cyano Ci_6 alkyl, cyano Ci-6 alkoxy, C2_6 alkenyl, C2_6 haloalkenyl, cyano C2-e alkenyl, C2-e alkynyl, C2-6 haloalkynyl, cyano C2-6 alkynyl, C3_8 cycloalkyl, C3_8 cycloalkyl Ci 6 alkyl, Ci_6 alkylthio, Ci_6
haloalkylthio, C3-8 cycloalkylthio, C3_8 cycloalkyl Ci-6
alkylthio, Ci_6 alkoxy Cj._6 alkylthio, Ci_6 alkylsulfonyl, Ci_6 alkylsulfinyl , Ci_6 haloalkylsulfonyl, Ci_6 haloalkylsulfinyl , C3-8 cycloalkylsulfonyl , C3-8 cycloalkylsulfinyl, C3_8
cycloalkyl, Ci-6 alkylsulfonyl , C3_8 cycloalkyl Ci_6
alkylsulfinyl , C2~e alkenyloxy, C2-e alkynyloxy, C2-6
haloalkenyloxy, C2_6 haloalkynyloxy, Ci_6 alkylsulfonyloxy, Ci-6 alkylsulfinyloxy, Ci-6 alkylcarbonyl , Ci^6 haloalkylcarbonyl , carboxyl, OCN, SCN, SF5, optionally substituted aryloxy, optionally substituted aryl Ci_6 alkoxy, optionally substituted arylthio, optionally substituted aryl Ci_6 alkylthio,
optionally substituted arylsulfonyl , optionally substituted
arylsulfinyl , optionally substituted heteroaryloxy, optionally substituted arylsulfonyloxy, optionally substituted
arylsulfinyloxy, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted heterocyclic group; and
the * is the point of attachment to the parent compound.
Item 22 :
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein R26, R27, R28, R29, R30, R31, R32, R33,
R35, R36, and R37 are identical or different and each represents hydrogen or halogen.
Item 23:
The dithiolane compound or a salt or an N-oxide thereof according to any one of the preceding items, wherein Y2 is selected from the group consisting of:
the * is the point of attachment to the parent compound.
Item 24 :
A dithiolane compound selected from the group consisting of compounds lc-1, lc-2H, lc-2L, lc-3, lc-3H, lc-3L, lc-4H, lc-4L, lc-SL, lc-6L, lc-8, lc-8H, lc-8L, lc-9, lc-9H, lc-9L, lc-lOH, lc-lOL, lc-HH, lc-llL, lc-13H, lc-13L, lc-14H, lc-15H, lc-16, 1C-16H, lc-19, lc-20, lc-23, lc-23H, lc-23L, lc-24, lc-24H, lc-25H, lc-25L, lc-26, lc-26H, lc-26L, lc-27H, lc-28L, lc-29H, lc-29L, lc-30H, lc-32H, lc-32L, lc-33, lc-34H, lc-34L, lc-35, lc-35H, lc-35L, ld-ΙΗ, ld-6H, ld-6L, ld-13, ld-17, ld-17H, ld-17L, le-3, and le-7, or a salt or an N-oxide thereof .
Item 25:
A dithiolane compound selected from the group consisting of compounds lc-2H, lc-2L, lc-3, lc-3H, lc-3L, lc-4H, lc-4L, lc-5L, lc-6L, lc-8, lc-8H, lc-8L, lc-9, lc-9H, lc-9L, lc-lOH, lc-lOL, lc-HH, lc-13H, lc-13L, lc-14H, lc-15H, lc-16, lc-16H, lc-19, lc-20, lc-23, lc-23H, lc-23L, lc-24H, lc-25H, lc-25L, lc-26, lc-26H, lc-26L, lc-27H, lc-29H, lc-29L, lc-32H, lc-32L, lc-33, lc-34H, lc-34L, lc-35, and lc-35H, or a salt or an N-oxide thereof.
Item 26:
A dithiolane compound selected from the group consisting of compounds lc-1, lc-ΙΗ, lc-lL, lc-2H, lc-2L, lc-3, lc-3H, lc-3L, lc-4H, lc-4L, lc-5H, lc-5L, lc-6, lc-6H, lc-6L, lc-7H, lc-7L, lc-8, lc-8H, lc-8L, lc-9, lc-9H, lc-9L, lc-lOH, lc-lOL, lc-HH, lc-llL, lc-13H, lc-13L, lc-14H, lc-15H, lc-15L, lc-16, lc-16H, lc-16L, lc-17H, lc-18L, lc-19H, lc-19L, lc-20, lc-21H, lc-21L, lc-22H, lc-23, lc-23H, lc-23L, lc-25H, lc-25L, lc-26, lc-26H, lc-26L, lc-27H, lc-27L, lc-28H, lc-28L, lc-29H, lc-29L, lc-30H, lc-30L, lc-31H, lc-31L, lc-32H, lc-32L, lc-33, lc-34H, lc-34L, lc-35, lc-35H, lc-35L, lc-36, lc-37, lc-37, lc-40H, lc-40L, lc-41H, lc-41L, ld-1, ld-ΙΗ, ld-lL, ld-12, ld-13 and ld-13L, or a salt or an N-oxide thereof.
Item 27 :
A dithiolane compound selected from the group consisting of compounds lc-1, lC-16, lc-16H, lc-16L, and lc-19H, or a salt or an N-oxide thereof.
Item 28:
A dithiolane compound selected from the group consisting of compounds lc-1, lc-lL, lc-2H, lc-2L, lc-3, lc-3H, lc-3L, lc-4H, lc-4L, lc-5H, lc-5L, lc-6, lc-6H, lc-6L, lc-8, lc-8H, lc-8L, lc-9, lc-9H, lc-9L, lc-ΙΟΗ, lc-lOL, lc-HH, lc-llL, lc-12, lc-12H, lc-13, lc-13H, lc-13L, lc-14H, lc-15H, lc-15L, lc-16, lc-16H, lc-16L, lc-17H, lc-18L, lc-19, lc-19L, lc-20, lc-21H, lc-21L, lc-23, lc-23H, lc-23L, lc-24, lc-24H, lc-25H, lc-25L, lc-26, lc-26H, lc-26L, lc-27H, lc-30L, lc-32H, lc-32L, 1C-34H, lc-34L, lc-35, lc-35H, lc-35L, lc-37, lc-37L, lc-38H, lc-38L, lc-44, lb-5L, ld-ΙΗ, ld-lL, ld-6L, ld-7, ld-7H, ld-7L, ld-8, ld-11, ld-llH, ld-HL, ld-12L, ld-15, ld-16, ld-16H, ld-16L, ld-17, ld-17H, and le-6, or a salt or an N-oxide thereof.
Item 29:
A plant disease-controlling agent containing the
dithiolane compound or a salt or an N-oxide thereof according to any one of Items 1 to 28.
Item 30:
A fungicide containing the dithiolane compound or a salt or an N-oxide thereof according to any one of Items 1 to 28.
Advantageous Effects of Invention
A dithiolane compound or a salt or an N-oxide thereof according to the present invention achieves an excellent fungicidal effect on fungal plant pathogens. Additionally, the dithiolane compound or a salt or an N-oxide thereof according to the present invention is useful as a new type of fungicide that exhibits excellent fungicidal activity not only against chemical-sensitive fungi, but also against chemical-resistant fungi .
Description of Embodiments
Hereinafter, the present invention will be described in more detail with reference to examples, but the technical scope of the present invention is not limited to these
examples. Throughout the entire specification, a singular expression should be understood as encompassing the concept thereof in the plural form, unless specifically noted
otherwise. Thus, singular articles (e.g., "a", "an", "the" and the like in case of English) should also be understood as encompassing the concept thereof in the plural form unless specifically noted otherwise. Further, the terms used herein should be understood as being used in the meaning that is commonly used in the art, unless specifically noted otherwise. Thus, unless defined otherwise, all terminologies and
scientific technical terms that are used herein have the same meaning as the terms commonly understood by those skilled in the art to which the present invention pertains. In case of a contradiction, the present specification (including the definitions) takes precedence.
A dithiolane compound or a salt or an N-oxide thereof The invention provides a dithiolane compound or a salt or an N-oxide thereof represented by the Formula (1) for use in agriculture and horticulture.
Wherein R1, R2, R3, Y1, Y2 and Q are as defined above.
The presence of one more possible asymmetric carbon atoms in a compound of Formula (1) means that the compounds may occur in optionally isomeric form, i.e. enantiomeric or diastereomeric forms. The presence of one or more possible double bonds in a compound of Formula (1) means that the compounds may occur in various diastereomeric forms.
Thus, the structure:
means both forms, namely the Z-form and the E-form:
(1-1) (1-11)
Also atropisomers may occur as a result of restricted rotation about a single bond. Formula (1) is intended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof for a compound of Formula (1). Likewise, Formula (1) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms for compound of Formula (1) .
Next, the terms in the present specification are
described below.
In the present specification, the number of substituents of a group defined by "optionally substituted" or
"substituted" is not particularly limited if it is
substitutable , and is one or plural. In addition, unless otherwise indicated, the description for each group is also applied when the group is one part of or a substituent on other groups.
"Ci-6 alkyl" means a linear or branched, saturated hydrocarbon group having one to six carbon atoms.
"C2-6 alkenyl" means a linear or branched, unsaturated hydrocarbon group having two to six carbon atoms and
containing one to three double bonds.
"C2-6 alkynyl" means a linear or branched, unsaturated hydrocarbon group having two to six carbon atoms and
containing one triple bond.
"C3-8 cycloalkyl" means a cyclic alkyl having three to eight carbon atoms, and includes those cyclic alkyls having a partially bridged structure.
"Ci-6 alkoxy" refers to a "Ci_6 alkoxy group", and the "Ci_6 alkyl" moiety is defined the same as the above-described "C 6 alkyl" .
"Aryl" means a monocyclic or polycyclic aromatic
hydrocarbon .
"Heterocyclic" means a saturated, unsaturated, or aromatic heterocyclic group which has at least one of
nitrogen, oxygen, phosphorus and/or sulfur atoms in the ring and may be bonded at any substitutable position.
"Heteroaryl" means an aromatic heterocyclic group which has at least one of nitrogen, oxygen, and/or sulfur atoms in the ring and may be bonded at any substitutable position, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, 0 and S.
The following shows specific examples of each group as used in this specification.
Examples of halogen include, but are not particularly limited to, fluorine, chlorine, bromine, iodine, and the like.
Examples of Ci-6 alkyl include, but are not particularly limited to Ci_6 straight-chain or branched-chain alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, and the like.
Examples of Ci-6 haloalkyl include, but are not
particularly limited to Ci-6 straight-chain or branched-chain alkyl substituted with 1 to 9, preferably 1 to 5, halogen atoms, such as fluoromethyl , chloromethyl , bromomethyl, iodomethyl, difluoromethyl , 2 , 2-difluoroethyl ,
trifluoromethyl, 2 , 2 , 2-trif luoroethyl , pentafluoroethyl ,
3,3, 3-t rifluoropropyl , 4,4, -trifluorobutyl ,
heptaf luoroisobutyl , and the like.
Examples of Ci-6 alkoxy include, but are not particularly limited to Ci-6 straight-chain or branched-chain alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy,
isobutoxy, sec-butoxy, tert-butoxy, and the like.
Examples of 0ι_δ haloalkoxy include, but are not
particularly limited to Ci-6 straight-chain or branched-chain alkoxy substituted with 1 to 9, preferably 1 to 5, halogen atoms, such as fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy , pentafluoroethoxy, 3, 3, 3-trifluoropropoxy, 4 , 4 , 4-trifluorobutoxy, heptafluoroisobutoxy, and the like.
Examples of Ci-6 alkoxy Ci_6 alkyl include, but are not particularly limited to alkoxyalkyl in which Ci~6 straight-chain or branched-chain alkyl is substituted with Ci_6
straight-chain or branched-chain alkoxy, such as
methoxymethyl , ethoxymethyl , n-propoxymethyl ,
isopropoxymethyl , n-butoxymethyl , isobutoxymethyl , sec-butoxymethyl , tert-butoxymethyl , methoxyethyl , ethoxyethyl, methoxy-n-propyl , methoxy-n-butyl , and the like.
Examples of Ci_6 haloalkoxy Ci-6 alkyl include, but are not particularly limited to straight-chain or branched-chain alkoxyalkyl substituted with 1 to 9, preferably 1 to 5, halogen atoms, such as fluoromethoxymethyl ,
chloromethoxymethyl , bromomethoxymethyl , iodomethoxymethyl , difluoromethoxymethyl , trifluoromethoxymethyl , 2,2,2-trifluoroethoxymethyl , and the like.
Examples of C 8 cycloalkyl include, but are not
particularly limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.
Examples of C3-8 cycloalkyl Ci-6 alkyl include, but are not particularly limited to, cyclopropylmethyl , cyclobutylethyl , cyclopentylmethyl , cyclohexylmethyl , and the like.
Examples of Ci-6 alkylcarbonyl include, but are not particularly limited to, Ci-6 straight-chain or branched-chain alkylcarbonyl groups, such as methylcarbonyl (acetyl), ethylcarbonyl (propionyl), n-propylcarbonyl (butyryl),
isopropylcarbonyl ( isobutyryl ) , n-butylcarbonyl (valeryl), isobutylcarbonyl ( isovaleryl ) , sec-butylcarbonyl , tert-butylcarbonyl , and the like.
Examples of Ci_6 haloal kylcarbonyl include, but are not particularly limited to, Ci-6 straight-chain or branched-chain alkylcarbonyl substituted with 1 to 9, and preferably 1 to 5, halogen atoms, such as fluoromethylcarbonyl ,
chloromethylcarbonyl , bromomethylcarbonyl , iodomethylcarbonyl , dichloromethylcarbonyl , trichloromethylcarbonyl ,
difluoromethylcarbonyl , trifluoromethylcarbonyl ,
chlorodifluoromethylcarbonyl , bromodifluoromethylcarbonyl , dichlorofluoromethylcarbonyl , 2,2, 2-trichloroethylcarbonyl, 2, 2, 2-trifluoroethylcarbonyl, pentafluoroethylcarbonyl, and the like.
Examples of CX-6 alkoxycarbonyl include, but are not
particularly limited to, Ci-6 straight-chain or branched-chain alkoxycarbonyl groups, such as methoxycarbonyl ,
ethoxycarbonyl , n-propoxycarbonyl , isopropoxycarbonyl , n-butoxycarbonyl , isobutoxycarbonyl , sec-butoxycarbonyl , tert-butoxycarbonyl , and the like.
Examples of C 6 haloalkoxycarbonyl include, but are not particularly limited to, Ci_6 straight-chain or branched-chain alkoxycarbonyl substituted with 1 to 9, preferably 1 to 5, halogen atoms, such as fluoromethoxycarbonyl ,
chloromethoxyca bonyl , bromomethoxycarbonyl ,
iodomethoxycarbony1 , dichloromethoxycarbony1 ,
trichloromethoxycarbonyl , difluoromethoxycarbonyl ,
trifluoromethoxycarbonyl, 2,2, 2-trifluoroethoxymethyl, pentafluoroethoxycarbonyl , 3, 3, 3-trifluoropropoxycarbonyl , 4, 4, 4-trifluorobutoxycarbonyl , heptafluoroisopropoxycarbonyl , and the like.
Examples of C3-8 cycloal kylcarbonyl include, but are not particularly limited to, cyclopropylcarbonyl ,
cyclobutylcarbonyl , cyclopentylcarbonyl , cyclohexylcarbonyl , and the like.
Examples of C3-a cycloal koxycarbonyl include, but are not particularly limited to, cyclopropyloxycarbonyl ,
cyclobutyloxycarbonyl , cyclopentyloxycarbonyl ,
cyclohexyloxycarbonyl , and the like.
Examples of cyano Ci-6 alkyl include, but are not
particularly limited to, Ci-6 straight-chain or branched-chain alkyl substituted with a cyano group, such as cyanomethyl, cyanoethyl, cyano-n-propyl , cyano-isopropyl , cyano-n-butyl , cyano-isobutyl , cyano-sec-butyl , cyano-tert-butyl , cyano-n-hexyl, and the like.
Examples of cyano C s alkoxy include C1-6 straight-chain or branched-chain alkoxy substituted with a cyano group, such as cyanomethoxy , cyanoethoxy, cyano-n-propoxy, cyano-isopropoxy, cyano-n-butoxy , cyano-iso-butoxy , cyano-sec-butoxy, cyano-tert-butoxy , cyano-hexyloxy, and the like.
Examples of C2-6 alkenyl include, but are not particularly limited to, vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl , and the like.
Examples of C2-6 haloalkenyl include, but are not
particularly limited to, 2 , 2-dichlorovinyl , 2 , 2-dibromovinyl , 2 , 2-difluorovinyl , 3 , 3-difluoro-2-allyl , 4 , 4 -difluoro-3-butenyl, 4 , 4 , - tri fluoro-2-butenyl , and the like.
Examples of C2-6 alkynyl include, but are not particularly limited to, ethynyl, 2-propynyl (propargyl) , l-methyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and the like.
Examples of C2-e haloalkynyl include, but are not
particularly limited to, fluoroethynyl , bromoethynyl ,
chloroethynyl , iodoethynyl, 3 , 3 , 3-trifluoro-l-propynyl , and the like.
Examples of cyano C2-e alkenyl include, but are not
particularly limited to, 2-cyanovinyl , 2, 2-dicyanovinyl, 3-cyano-2-allyl, 3, 3-dicyano-2-allyl, 4 -cyano-3-butenyl , 4,4-dicyano-3-butenyl , , , -tricyano-2-butenyl, and the like.
Examples of cyano C2~6 alkynyl include, but are not particularly limited to, cyanoethynyl , 3-cyano-l-propynyl , and the like.
Examples of Ci-6 alkylsulfonyl include, but are not particularly limited to, Ci-6 straight-chain or branched-chain alkylsulfonyl groups, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl , isopropylsulfonyl , n-butylsulfonyl ,
isobutylsulfonyl, sec-butylsulfonyl , tert-butylsulfonyl , and the like.
Examples of Ci-6 haloalkylsulfonyl include, but are not particularly limited to, Ci_6 straight-chain or branched-chain alkylsulfinyl groups substituted with 1 to 9, preferably 1 to 5, halogen atoms, such as fluoromethylsulfonyl ,
chloromethylsulfonyl, bromomethylsulfonyl, iodomethylsulfonyl , dichloromethylsulfonyl , trichloromethylsulfonyl ,
difluoromethylsulfonyl , trifluoromethylsul fonyl ,
chlorodifluoromethylsulfonyl , bromodifluoromethylsulfonyl , dichlorofluoromethylsulfonyl, 2,2, 2-trichloroethylsulfonyl,
2 , 2 , 2-trifluoroethylsulfonyl , pentafluoroethylsulfonyl, and the like.
Examples of