Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/04—Ortho-condensed systems

Definitions

• the present invention relates to amide compounds and plant disease control using the same.
• the present invention is intended to provide compounds having an excellent controlling effect on plant diseases.
• the present inventors earnestly investigated in order to find a compound having an excellent controlling effect on plant diseases, and consequently found that amide compounds represented by the formula (1) shown below has an excellent controlling effect on plant diseases, whereby the present invention has been accomplished.
• the present invention provides amide compounds represented by the formula (1) :
• Q is a group having a fused heterocyclic ring and selected from among the following groups Q 1 , Q 2 and Q 3 :
• n 1 is an integer of 0 to 6
• m 2 is an integer of 0 to 5
• m 3 is an integer of 0 to 4,
• R 1 independently in each occurrence is a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group or a cyano group, which is bonded to a carbon atom of the fused heterocyclic ring,
• R 2 independently in each occurrence is a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group or a cyano group, which is bonded to a carbon atom of the fused heterocyclic ring,
• R 3 independently in each occurrence is a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxyl group or a cyano group, which is bonded to a carbon atom of the fused heterocyclic ring,
• X 1 and X 3 are independently a methylene group which may be substituted with a C1-C4 alkyl group or two C1-C4 alkyl groups which may be the same or different
• X 2 is a divalent C2-C5 linear hydrocarbon group which has a free valence on each terminal carbon atom and may be substituted with one or more groups selected from the group consisting of halogen atoms, C1-C4 alkyl groups and C1-C4 alkoxyl groups
• Z 1 is an oxygen atom or a sulfur atom
• G 1 is a single bond, an oxygen atom, a sulfur atom or a >N-R 4 group,
• R 4 is a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C2-C5 alkylcarbonyl group or a C2-C5 alkoxycarbonyl group, and
• a 1 is a C2-C8 alkyl group which may be substituted with one or more groups selected from the group [a-1] described below; a C2-C8 alkenyl group which may be substituted with one or more groups selected from the group [a-1] ; a C2-C8 alkynyl group which may be substituted with one or more groups selected from the group [a-1] ; a C3-C5 cycloalkyl group which may be substituted with one or more groups selected from the group [a-1] ; or a 5- to 10-membered aromatic ring group which may be substituted with one or more groups selected from the group [a-1] , provided that G 1 is a single bond in the case of A 1 being a vinyl group which may be substituted with one or more groups selected from the group [a-1] or an ethynyl group which may be substituted with one or more groups selected from the group [a-1] : the group [a-1] consisting of halogen atoms, hydroxyl group, carb
• G 3 -A 3 wherein A 3 is a C3-C10 cyclic hydrocarbon group or a 5- to 10-membered heterocyclic group, and G 3 is a single bond, an oxygen atom, a sulfur atom or a >N-R 6 group wherein R 6 is a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C2-C5 alkylcarbonyl group or a C2-C5 alkoxycarbonyl group (said amide compound is hereinafter referred to as the invented compound) , a plant disease controlling agent characterized by comprising the invented compound as an active ingredient (said agent is hereinafter referred to as the invented controlling agent) , and a method for controlling plant diseases characterized by applying an effective amount of the invented compound to plants or soil (said method is hereinafter referred to as the invented controlling method) .
• the invented compound has an excellent controlling effect on plant diseases and hence is useful as an active ingredient of compositions for controlling plant disease.
• the symbol m 1 is an integer of 0 to 6 and preferably is 0.
• the symbol m 2 is an integer of 0 to 5 and preferably is 0.
• m 3 is an integer of 0 to 4 and preferably is 0.
• Z 1 in the formula (1) which represents the invented compound is an oxygen atom or a sulfur atom, and preferably is an oxygen atom.
• X 1 and X 3 in the formula (1) which represents the invented compound are independently a methylene group unsubstituted or substituted with a C1-C4 alkyl group or two C1-C4 alkyl groups which may be the same or different, and each of X 1 and X 3 is preferably a methylene group.
• G 1 in the formula (1) which represents the invented compound is a single bond, an oxygen atom, a sulfur atom or a >N-R 4 group, preferably is a single bond or an oxygen atom, more preferably is a single bond.
• examples of the divalent C2-C5 linear hydrocarbon group include ethylene group, trimethylene group, tetramethylene group, pentamethylene group, vinylene group, 1- propenylene group, 2-propenylene group, 1-butenylene group, 2-butenylene group, 3-butenylene group, 1- pentenylene group, 2-pentenylene group, 3-pentenylene group, 4-pentenylene group, ethynylene group, 1- propynylene group, 2-propynylene group, 1-butynylene group, 2-butynylene group, 3-butynylene group, 1- pent
• X 2 preferably is a divalent C2 hydrocarbon group having a free valence on its each terminal carbon atom and may be substituted with one or more C1-C4 alkyl groups.
• Examples of the divalent C2 hydrocarbon group having a free valence on its each terminal carbon atom include ethylene group, vinylene group and ethynylene group .
• the halogen atom represented by R 1 includes fluorine atom, chlorine atom, bromine atom and iodine atom.
• the C1-C4 alkyl group includes methyl group, ethyl group, 1-methylethyl group, 1, 1-dimethylethyl group, propyl group, 1-methylpropyl group, etc.
• the C1-C4 alkoxyl group includes methoxy group, ethoxy group, 1-methylethoxy group, 1,1- dimethylethoxy group, propoxy group, 1-methylpropoxy group, 2-methylpropoxy group, butoxy group, etc.
• the C1-C4 alkyl group represented by each of R 4 , R 5 and R 6 includes methyl group, ethyl group, 1- methylethyl group, 1, 1-dimethylethyl group, propyl group, 1-methylpropyl group, etc.
• the C3-C4 alkenyl group includes 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, etc.
• the C3-C4 alkynyl group includes 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, etc.
• the C2-C5 alkylcarbonyl group includes acetyl group, ethylcarbonyl group, 1-methylethylcarbonyl group, 1, 1-dimethylethylcarbonyl group, etc.
• the C2-C5 alkoxycarbonyl group includes methoxycarbonyl group, ethoxycarbonyl group, 1- r ⁇ ethylethoxycarbonyl group, 1, 1-dimethylethoxycarbonyl group, etc.
• the C2-C8 alkyl group which may be substituted with one or more groups selected from the group [a-1] represented by A 1 in the formula (1) which represents the invented compound include ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group and octyl group .
• Examples of the C2-C8 alkenyl group which may be substituted with one or more groups selected from the group [a-1] include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3- butenyl group, 1-pentenyl group, 2-pentenyl group, 3- pentenyl group, 4-pentenyl group, 1-hexenyl group, 2- hexenyl group, 3-hexenyl group, 4-hexenyl group, 5- hexenyl group, 1-heptenyl group, 2-heptenyl group, 3- heptenyl group, 4-heptenyl group, 5-heptenyl group, 6- heptenyl group, 1-octenyl group, 2-octenyl group, 3- octenyl group, 4-octenyl group, 5-octenyl group, 6- octenyl group and 7-octenyl group.
• Examples of the C2-C8 alkynyl group which may be substituted with one or more groups selected from the group [a-1] include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, 1-heptynyl group, 2-heptynyl group, 3-heptynyl group, 4-heptynyl group, 5-heptynyl group, 6-heptynyl group, 1-octynyl group, 2-octynyl group, 3-octynyl group, 4-octynyl
• Examples of the C3-C5 cycloalkyl group which may be substituted with one or more groups selected from the group [a-1] include cyclopropyl group, cyclobutyl group and cyclopentyl group.
• Examples of the 5- to 10-membered aromatic ring group which may be substituted with one or more groups selected from the group [a-1] include 6- to 10- membered aromatic hydrocarbon groups such as phenyl group and naphthyl group, and 5- to 10-membered aromatic heterocyclic groups.
• 5- to 10-membered aromatic heterocyclic groups are 5- membered aromatic heterocyclic groups such as furyl group, thienyl group, pyrrolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, pyrazolyl group, imidazolyl group, 1, 2, 3-triazolyl group, 1, 2, 4-triazolyl ' group, 1, 2, 5-oxadiazolyl group, 1, 2, 4-oxadiazolyl group, 1, 2, 3-oxadiazolyl group, 1,2, 5-thiadiazolyl group, 1, 2, 4-thiadiazolyl group, 1,2, 3-thiadiazolyl group, tetrazolyl group, etc.; 6- membered aromatic heterocyclic groups such as pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, 1,2, 4-triazinyl group, 1, 3, 5-triazinyl group, etc.
• the C3-C10 cyclic hydrocarbon group represented by each of A 2 and A 3 include C3-C10 aliphatic cyclic hydrocarbon groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc.; and C6-C10 aromatic cyclic hydrocarbon groups such as phenyl group, naphthyl group, etc.
• the 5- to 10-meitibered heterocyclic group represented by each of A 2 and A 3 include 5-meinbered heterocyclic groups such as furyl group, thienyl group, pyrrolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, pyrazolyl group, imidazolyl group, 1,2, 3-triazolyl group, 1,2,4- triazolyl group, 1, 2, 5-oxadiazolyl group, 1,2,4- oxadiazolyl group, 1, 2, 3-oxadiazolyl group, 1,2,5- thiadiazolyl group, 1, 2, 4-thiadiazolyl group, 1,2,3- thiadiazolyl group, tetrazolyl group, etc.; 6-membered heterocyclic groups such as pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, 1,2,4- triazinyl group, 1, 3,
• the halogen atoms in the group [a-1] include fluorine atom, chlorine atom, bromine atom and iodine atom.
• the Cl-C ⁇ alkyl groups in the group [a-1] include methyl group, ethyl group, 1-methylethyl group, 1, 1-dimethylethyl group, propyl group, 1-methylpropyl group, butyl group, pentyl group, hexyl group, etc.
• the C2-C6 alkenyl groups in the group [a-1] include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, etc.
• the C2-C6 alkynyl groups in the group [a-1] include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, etc.
• the C1-C6 alkoxyl groups in the group [a-1] include methoxy group, ethoxy group, 1-methylethoxy group, 1, 1-dimethylethoxy group, propoxy group, 1- methylpropoxy group, butoxy group, pentyloxy group, hexyloxy group, etc.
• the C3-C6 alkenyloxy groups in the group [a- 1] include 2-propenyloxy group, 2-butenyloxy group, 3- butenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 2-hexenyloxy group, 3- hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, etc.
• the C3-C6 alkynyloxy groups in the group [a- 1] include 2-propynyloxy group, 2-butynyloxy group, 3- butynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 2-hexynyloxy group, 3- hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group, etc.
• the C1-C6 alkylthio groups in the group [a-1] include methylthio group, ethylthio group, 1- methylethylthio group, 1, 1-dimethylethylthio group, propylthio group, 1-methylpropylthio group, butylthio group, pentylthio group, hexylthio group, etc.
• the C3-C6 alkenylthio groups in the group fall include 2-propenylthio group, 2-butenylthio group, 3-butenylthio group, 2-pentenylthio group, 3- pentenylthio group, 4-pentenylthio group, 2-hexenylthio group, 3-hexenylthio group, 4-hexenylthio group, 5- hexenylthio group, etc.
• the C3-C6 alkynylthio groups in the group [a- 1] include 2-propynylthio group, 2-butynylthio group, 3-butynylthio group, 2-pentynylthio group, 3- pentynylthio group, 4-pentynylthio group, 2-hexynylthio group, 3-hexynylthio group, 4-hexynylthio group, 5- hexynylthio group, etc.
• the C1-C6 alkylsulfinyl groups in the group [a-1] include methylsulfinyl group, ethylsulfinyl group, 1-methylethylsulfinyl group, 1,1- dimethylethylsulfinyl group, propylsulfinyl group, 1- methylpropylsulfinyl group, butylsulfinyl group, pentylsulfinyl group, hexylsulfinyl group, etc.
• the C1-C6 alkylsulfonyl groups in the group [a-1] include methylsulfonyl group, ethylsulfonyl group, 1-methylethylsulfonyl group, 1,1- dimethylethylsulfonyl group, propylsulfonyl group, 1- methylpropylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, etc.
• the C1-C6 alkylsulfonyloxy groups in the group [a-1] include methylsulfonyloxy group, ethylsulfonyloxy group, etc.
• the C2-C7 alkylcarbonyl groups in the group [a-1] include acetyl group, propionyl group, isobutyryl group, pivaloyl group, butyryl group, isovaleryl group, valeryl group, hexanoyl group, heptanoyl group, etc.
• the C2-C7 alkoxycarbonyl groups in the group [a-1] include methoxycarbonyl group, ethoxycarbonyl group, 1-methylethoxycarbonyl group, 1,1- dimethylethoxycarbonyl group, etc.
• the (C1-C6 alkyl) aminocarbonyl groups in the group [a-1] include methylaminocarbonyl group, ethylaminocarbonyl group, 1-methylethylaminocarbonyl group, 1, 1-dimethylethylaminocarbonyl group, propylaminocarbonyl group, 1-methylpropylaminocarbonyl group, butylaminocarbonyl group, pentylaminocarbonyl group, hexylaminocarbonyl group, etc.
• the di (Cl-C ⁇ alkyl) aminocarbonyl groups in the group [a-1] include dimethylaminocarbonyl group, N- methyl-N-ethylaminocarbonyl group, diethylaminocarbonyl group, etc.
• the C2-C7 alkylcarbonyloxy groups in the group [a-1] include acetoxy group, propionyloxy group, isobutyryloxy group, pivaloyloxy group, butyryloxy group, isovaleryloxy group, valeryloxy group, hexanoyloxy group, heptanoyloxy group, etc.
• the C2-C7 alkoxycarbonyloxy groups in the group [a-1] include methoxycarbonyloxy group, ethoxycarbonyloxy group, 1-methylethoxycarbonyloxy group, 1, 1-dimethylethoxycarbonyloxy group, propoxycarbonyloxy group, 1-methylpropoxycarbonyloxy group, butoxycarbonyloxy group, pentyloxycarbonyloxy group, hexyloxycarbonyloxy group, etc.
• the (C1-C6 alkyl) aminocarbonyloxy groups in the group [a-1] include methylaminocarbonyloxy group, ethylar ⁇ inocarbonyloxy group, 1- methylethylaminocarbonyloxy group, 1,1- dimethylethylaminocarbonyloxy group, propylaminocarbonyloxy group, 1- methylpropylaminocarbonyloxy group, butylaminocarbonyloxy group, pentylaminocarbonyloxy group, hexylaminocarbonyloxy group, etc.
• the di (C1-C6 alkyl) aminocarbonyloxy groups in the group [a-1] include dimethylaminocarbonyloxy group,
• methylamino group examples include methylamino group, ethylamino group, 1- methylethylamino group, 1, 1-dimethylethylamino group, propylamino group, 1-methylpropylamino group, butylamino group, pentylamino group, hexylamino group, etc.
• [a-1] include 2-propenylamino group, 2-butenylamino group, 3-butenylar ⁇ ino group, 2-pentenylamino group, 3- pentenylamino group, 4-pentenylamino group, 2- hexenylamino group, 3-hexenylamino group, 4- hexenylamino group, 5-hexenylamino group, etc.
• the C3-C6 alkynylamino groups in the group [a-1] include 2-propynylamino group, 2-butynylamino group, 3-butynylamino group, 2-pentynylamino group, 3- pentynylamino group, 4-pentynylamino group, 2- hexynylamino group, 3-hexynylamino group, 4- hexynylamino group, 5-hexynylamino group, etc.
• the C2-C7 alkylcarbonylamino groups in the group [a-1] include acetamino group, propionylamino group, isobutyrylamino group, pivaloylamino group, butyrylainino group, isovalerylamino group, valerylamino group, hexanoylamino group, heptanoylamino group, etc.
• the C2-C7 alkoxycarbonylamino groups in the group [a-1] include methoxycarbonylamino group, ethoxycarbonylamino group, 1-r ⁇ ethylethoxycarbonylamino group, 1, 1-dimethylethoxycarbonylar ⁇ ino group, propoxycarbonylamino group, 1- methylpropoxycarbonylamino group, butoxycarbonylamino group, pentyloxycarbonylamino group, hexyloxycarbonylamino group, etc.
• the Cl-C ⁇ alkylsulfonylamino groups in the group [a-1] include methylsulfonylamino group, ethylsulfonylamino group, 1-methylethylsulfonylamino group, 1, 1-dimethylethylsulfonylamino group, propylsulfonylamino group, 1-methylpropylsulfonylamino group, butylsulfonylamino group, pentylsulfonylamino group, hexylsulfonylamino group, etc.
• the di (C1-C6 alkyl) amino groups in the group [a-1] include dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group, N-methyl-N- ethylamino group, N-methyl-N-propylamino group, N- methyl-N- (1-methylethyl) amino group, N-methyl-N- (1, 1- dimethylethyl) amino group, N-methyl-N-propylamino group, N-methyl-N- (1-methylpropyl) amino group, N- methyl-N-butylamino group, N-methyl-N-pentylamino group, N-methyl-N-hexylamino group, etc.
• the halogen atoms in the group [a-2] include fluorine atom, chlorine atom, bromine atom and iodine atom.
• the Cl-C ⁇ alkyl groups in the group [a-2] include methyl group, ethyl group, 1-methylethyl group, 1, 1-dimethylethyl group, propyl group, 1-methylpropyl group, butyl group, pentyl group, hexyl group, etc.
• the C2-C6 alkenyl groups in the group [a-2] include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, etc.
• the C2-C6 alkynyl groups in the group [a-2] include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, etc.
• the Cl-C ⁇ haloalkyl groups in the group [a-2] include fluoromethyl group, difluoromethyl group, trifluoromethyl group, trichloror ⁇ ethyl group, chlorofluoromethyl group, bromodifluoromethyl group, 2- fluoroethyl group, 2, 2-difluoroethyl group, 2,2,2- trifluoroethyl group, 6, 6, 6-trifluorohexyl group, etc.
• the C1-C6 alkoxyl groups in the group [a-2] include methoxy group, ethoxy group, 1-methylethoxy group, 1, 1-dimethylethoxy group, propoxy group, 1- methylpropoxy group, butoxy group, pentyloxy group, hexyloxy group, etc.
• the C3-C6 alkenyloxy groups in the group [a-) include methoxy group, ethoxy group, 1-methylethoxy group, 1, 1-dimethylethoxy group, propoxy group, 1- methylpropoxy group, butoxy group, pentyloxy group, hexyloxy group, etc.
• the C3-C6 alkynyloxy groups in the group [a- 2] include 2-propynyloxy group, 2-butynyloxy group, 3- butynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 2-hexynyloxy group, 3- hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group, etc.
• the C1-C6 alkylthio groups in the group [a-2] include methylthio group, ethylthio group, 1- methylethylthio group, 1, 1-dimethylethylthio group, propylthio group, 1-methylpropylthio group, butylthio group, pentylthio group, hexylthio group, etc.
• the Cl-C ⁇ alkylsulfinyl groups in the group [a-2] include methylsulfinyl group, ethylsulfinyl group, 1-methylethylsulfinyl group, 1,1- dimethylethylsulfinyl group, propylsulfinyl group, 1- methylpropylsulfinyl group, butylsulfinyl group, pentylsulfinyl group, hexylsulfinyl group, etc.
• [a-2] include methylsulfonyl group, ethylsulfonyl group, 1-methylethylsulfonyl group, 1,1- dimethylethylsulfonyl group, propylsulfonyl group, 1- methylpropylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, etc.
• the C2-C7 alkylcarbonyl groups in the group [a-2] include acetyl group, propionyl group, isobutyryl group, pivaloyl group, butyryl group, isovaleryl group, valeryl group, hexanoyl group, heptanoyl group, etc.
• the C2-C7 alkoxycarbonyl groups in the group include acetyl group, propionyl group, isobutyryl group, pivaloyl group, butyryl group, isovaleryl group, valeryl group, hexanoyl group, heptanoyl group, etc.
• [a-2] include methoxycarbonyl group, ethoxycarbonyl group, 1-methylethoxycarbonyl group, 1,1- dimethylethoxycarbonyl group, etc.
• the (C1-C6 alkyl) aminocarbonyl groups in the group [a-2] include methylaminocarbonyl group, ethylaminocarbonyl group, 1-methylethylaminocarbonyl group, 1, 1-dimethylethylaminocarbonyl group, propylaminocarbonyl group, 1-methylpropylaminocarbonyl group, butylaminocarbonyl group, pentylaminocarbonyl group, hexylaminocarbonyl group, etc.
• the di (C1-C6 alkyl) aminocarbonyl groups in the group [a-2] include dimethylaminocarbonyl group, N- methyl-N-ethylaminocarbonyl group, diethylaminocarbonyl group, etc.
• the group represented by A 1 is preferably as follows.
• the C2-C8 alkyl group which may be substituted with one or more groups selected from the group [a-1] includes ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, etc.
• the C2-C8 alkenyl group which may be substituted with one or more groups selected from the group [a-1] includes vinyl group, 1-propenyl group, 2- propenyl group, 1-butenyl group, 2-butenyl group, 3- butenyl group, 1-pentenyl group, 2-pentenyl group, 3- pentenyl group, 4-pentenyl group, 1-hexenyl group, 2- hexenyl group, 3-hexenyl group, 4-hexenyl group, 5- hexenyl group, 1-heptenyl group, 2-heptenyl group, 3- heptenyl group, 4-heptenyl group, 5-heptenyl group, 6- heptenyl group, 1-octenyl group, 2-octenyl group, 3- octenyl group, 4-octenyl group, 5-octenyl group, 6- octenyl group and 7-octenyl group.
• the C2-C8 alkynyl group which may be substituted with one or more groups selected from the group [a-1] includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2- butynyl group, 3-butynyl group, 1-pentynyl group, 2- pentynyl group, 3-pentynyl group, 4-pentyn ⁇ l group, 1- hexynyl group, 2-hexynyl group, 3-hexynyl group, 4- hexynyl group, 5-hexynyl group, 1-heptynyl group, 2- heptynyl group, 3-heptynyl group, 4-heptynyl group, 5- heptynyl group, 6-heptynyl group, 1-octynyl group, 2- octynyl group, 3-octynyl group, 4-octy
• the group represented by A 1 is more preferably as follows.
• the C2-C4 alkyl group which may be substituted with one or more groups selected from the group [a-1] includes ethyl group, propyl group and butyl group.
• the C2-C4 alkenyl group which may be substituted with one or more groups selected from the group [a-1] includes vinyl group, 1-propenyl group, 2- propenyl group, 1-butenyl group, 2-butenyl group and 3- butenyl group.
• the C2-C4 alkynyl group which may be substituted with one or more groups selected from the group [a-1] includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group and 3-butynyl group.
• Phenyl group is an example of the 5- to 10-membered aromatic ring group which may be substituted with one or more groups selected from the group [a-1] .
• X 1 , X 2 , X 3 , Z 1 , G 1 and A 1 are as defined above, and Q is a group selected from among the following groups Q 1 , Q 2 and Q 3 :
• X 4 is a divalent C2 hydrocarbon group which has a free valence on each carbon atom and may be substituted with one or more groups selected from the group consisting of halogen atoms and C1-C4 alkyl groups, and R 7 is any group selected from the group [a- I]), or a phenyl group which may be substituted with one or more groups selected from the group [a-2] ;
• the invented compound can be produced, for example, by any of the following (production process 1) to (production process 4) .
• an invented compound (5) in which Z 1 is an oxygen atom can be produced by causing a compound (2) to react with a compound (3) in the presence of a dehydrating- condensation agent:
• This reaction is usually carried out in the presence of a solvent.
• the solvent used in the reaction includes, for example, ethers such as tetrahydrofuran
• THF ethylene glycol dimethyl ether
• MTBE tert-butyl methyl ether
• aliphatic hydrocarbons such as hexane, heptane, octane, etc.
• aromatic hydrocarbons such as toluene, xylene, etc.
• halogenated hydrocarbons such as chlorobenzene, etc.
• esters such as butyl acetate, ethyl acetate, etc.
• nitriles such as acetonitrile, etc.
• acid amides such as N,N-dimethylformamide (hereinafter referred to as DMF in some cases), etc.
• sulfoxides such as dimethyl sulfoxide (hereinafter referred to as DMSO in some cases), etc.; and mixtures thereof.
• the dehydrating-condensation agent used in the reaction includes, for example, l-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride
• WSC (benzotriazol-1- yloxy) tris (dimethylamino) phosphonium hexafluorophosphate
• BOP reagent (benzotriazol-1- yloxy) tris (dimethylamino) phosphonium hexafluorophosphate
• S-dicyclohexylcarbodiimide 1, S-dicyclohexylcarbodiimide.
• the compound (3) is usually used in an amount of 1 to 3 moles per mole of the compound (2), and the dehydrating-condensation agent is usually used in an amount of 1 to 5 moles per mole of the compound (2) .
• the reaction temperature ranges usually from 0 to 140°C, and the reaction time ranges usually from 1 to 24 hours.
• a base includes, for example, tertiary amines such as triethylamine, diisopropylethylamine, etc.; and nitrogen-containing aromatic compounds such as pyridine, 4-dimethylaminopyridine, etc.
• the base is usually used in an amount of 1 to 3 moles per mole of the compound (3) .
• the invented compound (5) can be isolated by filtering the reaction mixture, extracting the filtrate with an organic solvent, and carrying out post-treatments such as drying and concentration of the organic layer.
• the invented compound (5) isolated can be further purified by chromatography, recrystallization, etc.
• an invented compound (5) in which Z 1 is an oxygen atom can be produced by causing a compound (2) to react with a compound (4) in the presence of a base:
• the solvent used in the reaction includes, for example, ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as chlorobenzene, etc.; esters such as butyl acetate, ethyl acetate, etc.; nitriles such as acetonitrile, etc.; acid amides such as DMF, etc.; sulfoxides such as DMSO, etc.; and mixtures thereof.
• ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.
• aliphatic hydrocarbons such as hexane, heptane, octane, etc.
• aromatic hydrocarbons such as toluene, xylene, etc.
• the base used in the reaction includes, for example, alkali metal carbonates such as sodium carbonate, potassium carbonate, etc.; tertiary amines such as triethylamine, diisopropylethylamine, etc.; and nitrogen-containing aromatic compounds such as pyridine, 4-dimethylaminopyridine, etc.
• alkali metal carbonates such as sodium carbonate, potassium carbonate, etc.
• tertiary amines such as triethylamine, diisopropylethylamine, etc.
• nitrogen-containing aromatic compounds such as pyridine, 4-dimethylaminopyridine, etc.
• the compound (2) is usually used in an amount of 1 to 3 moles per mole of the compound (4), and the base is usually used in an amount of 1 to 10 moles per mole of the compound (4) .
• the reaction temperature ranges usually from -20 to 100 0 C, and the reaction time ranges usually from 0.1 to 24 hours.
• the invented compound (5) can be isolated by extracting the reaction mixture with an organic solvent and carrying out post-treatments such as drying and concentration of the organic layer.
• the invented compound (5) isolated can be further purified by chromatography, recrystallization, etc.
• an invented compound (6) in which Z 1 is a sulfur atom can be produced by causing an invented compound (5) in which Z 1 is an oxygen atom, to react with a sulfurizing agent such as phosphorus pentasulfide or 2,4-bis(4- methoxyphenyl) -1, 3-dithia-2, 4-diphosphetane-2, 4- disulfide (hereinafter referred to as Lawesson reagent) :
• a sulfurizing agent such as phosphorus pentasulfide or 2,4-bis(4- methoxyphenyl) -1, 3-dithia-2, 4-diphosphetane-2, 4- disulfide (hereinafter referred to as Lawesson reagent) :
• the reaction is usually carried out in the presence of a solvent.
• the solvent used in the reaction includes, for example, ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc. ; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as chlorobenzene, etc.; organic nitriles such as acetonitrile, butyronitrile, etc.; sulfoxides such as dimethyl sulfoxide, etc.; and mixtures thereof.
• ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.
• aliphatic hydrocarbons such as hexane, heptane, octane, etc.
• aromatic hydrocarbons such as toluene, xylene, etc.
• the sulfurizing agent is usually used in an amount of 1 to 2 moles per mole of the invented compound (5) .
• the reaction temperature ranges usually from 25 to 150°C, and the reaction time ranges usually from 0.1 to 24 hours.
• the invented compound (6) can be isolated by extracting the reaction mixture with an organic solvent and carrying out post-treatments such as drying and concentration of the organic layer.
• the invented compound (6) isolated can be further purified by chromatography, recrystallization, etc.
• an invented compound (11) in which Z 1 is an oxygen atom, A 1 is a phenyl group which may be substituted with one or more groups selected from the group [a-2] , and G 1 is an oxygen atom, a sulfur atom or a >N-R 4 group, can be produced by a process shown in the following scheme:
• a 4 is a phenyl group which may be substituted with one or more groups selected from the group [a-2] , G 4 is an oxygen atom, a sulfur atom or a >N-R 4 group, L is a chlorine atom, a bromine atom, an iodine atom or a methanesulfonyloxy group, and Q, X 1 , X 2 and X 3 are as defined above.
• a compound (8) can be produced by causing a compound (3) to react with a compound (7) in the presence of a dehydrating-condensation agent.
• Step (IV-2) A compound (9) can be produced by causing the compound (8) to react with a halogenating agent or methanesulfonyl chloride.
• the reaction is usually carried out in the presence of a solvent.
• the solvent used in the reaction includes ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as chlorobenzene, etc.; esters such as butyl acetate, ethyl acetate, etc.; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.; nitriles such as acetonitrile, etc.; acid amides such as DMF, etc.; sulfoxides such as dimethyl sulfoxide, etc.; and mixtures thereof.
• the halogenating agent used in the reaction includes, thionyl chloride, hydrochloric acid, carbon tetrachloride, hydrobromic acid, carbon tetrabromide, hydroiodic acid, etc.
• the halogenating agent or methanesulfonyl chloride is usually used in an amount of 1 to 3 moles per mole of the compound (8) .
• the reaction temperature ranges usually from -20 to 150 0 C, and the reaction time ranges usually from 0.1 to 24 hours.
• the reaction is carried out in the presence of a base.
• the base includes, for example, tertiary- amines such as triethylamine, diisopropylethylamine, etc.; and nitrogen-containing aromatic compounds such as pyridine, 4-dimethylaminopyridine, etc.
• the base is usually used in an amount of 1 to 3 moles per mole of the compound (8) .
• the compound (9) can be isolated by pouring the reaction mixture into water, followed by extraction with an organic solvent, and carrying out post-treatments such as drying and concentration of the organic layer.
• the compound (9) isolated can be further purified by chromatography, recrystallization, etc.
• the invented compound (11) can be produced by causing the compound (9) to react with a compound (10) in the presence of a base.
• This reaction is usually carried out in the presence of a solvent.
• the solvent used in the reaction includes, for example, ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.; aliphatic hydrocarbons such as hexane, heptane, octane, etc.; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as chlorobenzene, etc.; esters such as butyl acetate, ethyl acetate, etc.; nitriles such as acetonitrile, etc.; acid amides such as DMF, etc.; sulfoxides such as dimethyl sulfoxide, etc.; water; and mixtures thereof.
• ethers such as THF, ethylene glycol dimethyl ether, MTBE, etc.
• aliphatic hydrocarbons such as hexan
• the base used in the reaction includes, for example, alkali metal carbonates such as sodium carbonate, potassium carbonate, etc.; alkali metal hydrogencarbonates such as sodium hydrogencarbonate, etc.; alkali metal hydrides such as sodium hydride, etc.; alkali metal hydroxides such as sodium hydroxide, etc.; tertiary amines such as triethylamine, diisopropylethylamine, etc.; and nitrogen-containing aromatic compounds such as pyridine, 4- dimethylaminopyridine, etc.
• the compound (10) is usually used in an amount of 1 to 3 moles per mole of the compound (9)
• the base is usually used in an amount of 1 to 3 moles per mole of the compound (9) .
• the reaction temperature ranges usually from -20 to 150°C, and the reaction time ranges usually from 0.1 to 24 hours.
• the invented compound (11) can be isolated by extracting the reaction mixture with an organic solvent and carrying out post-treatments such as drying and concentration of the organic layer.
• the invented compound (11) isolated can be further purified by chromatography, recrystallization, etc.
• the invented controlling agent may be composed of only the invented compound
• the invented compound is used usually after having been formulated into any of formulations such as wettable powders, water dispersible granules, flowable concentrates, granules, dry flowable concentrates, emulsifiable concentrates, aqueous liquid formulations, oil formulations, smoking formulations, aerosols, microcapsules, etc. by mixing with a carrier (e.g. a solid, liquid or gaseous carrier) , a surfactant and other auxiliaries for formulation, such as adhesive agent, dispersant, stabilizer, etc.
• a carrier e.g. a solid, liquid or gaseous carrier
• surfactant and other auxiliaries for formulation, such as adhesive agent, dispersant, stabilizer, etc.
• the solid carrier includes, for example, fine powders and granules of clays (e.g. kaolin, diatomaceous earth, synthetic hydrated silicon oxide, fubasami clay, bentonite and acid clay) and talcs, and other inorganic minerals (e.g. sericite, quartz powder, sulfur powder, activated carbon, calcium carbonate and hydrated silica) .
• the liquid carrier includes, for example, water, alcohols (e.g. methanol and ethanol) , ketones (e.g. acetone and methyl ethyl ketone), aromatic hydrocarbons (e.g.
• benzene, toluene, xylene, ethylbenzene and methylnaphthalene) , aliphatic or alicyclic hydrocarbons (e.g. n-hexane, cyclohexanone and kerosene), esters (e.g. ethyl acetate and butyl acetate), nitriles (e.g. acetonitrile and isobutyronitrile) , ethers (e.g. dioxane and diisopropyl ether), acid amides (e.g. dimethylformamide and dimethylacetamide) , and halogenated hydrocarbons (e.g. dichloroethane, trichloroethylene and carbon tetrachloride) .
• aliphatic or alicyclic hydrocarbons e.g. n-hexane, cyclohexanone and kerosene
• esters e.
• the surfactant includes, for example, alkyl sulfates, alkylsulfonates, alkylarylsulfonates, alkyl aryl ethers and their polyoxyethylenated products, polyoxyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.
• the other auxiliaries for formulation include, for example, adhesive agents, dispersants, thickening agents, wetting agents, extending agents and antioxidants. Specific examples thereof are casein, gelatin, polysaccharides (e.g. starch, gum arabic, cellulose derivative and alginic acid) , lignin derivatives, bentonite, saccharides, synthetic water- soluble polymers [e.g.
• a method for applying the invented controlling agent in order to control plant diseases is not particularly limited.
• the method includes, for example, treatment of plants, such as foliage application; treatment of a plant cultivation area, such as soil treatment; and treatment of seeds, such as seed disinfection.
• the invented controlling agent can be used in admixture with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners. It is also possible to use the invented controlling agent in combination with such other chemicals without mixing with them.
• Such other fungicides include, for example, azole fungicidal compounds such as propiconazole, prothioconazole , triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metoconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, flutriafol, etc.
• azole fungicidal compounds such as propiconazole, prothioconazole , triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazo
• cyclic amine fungicidal compounds such as fenpropimorph, tridemorph, fenpropidin, etc.
• benzimidazole fungicidal compounds such as carbendazim, benomyl, thiabendazole, thiophanate-methyl, etc.
• the applying dosage of the invented controlling agent varied depending on weather conditions, formulation, when, where and how the invented controlling agent is applied, diseases to be controlled, crop plants to be protected, etc., it is usually 1 to 500 g, preferably 2 to 200 g, (in terms of the invented compound in the invented controlling agent), per 10 ares.
• the invented controlling agent is an emulsifiable concentrate, wettable powder, suspension concentrate or the like, it is usually applied after having been diluted with water. In this case, the concentration of the invented compound after the dilution is usually 0.0005 to 2% by weight, preferably 0.005 to 1% by weight.
• the invented controlling agent is a powder, granules or the like, it is applied as it is without dilution.
• its applying dosage is usually 0.001 to 100 g, preferably 0.01 to 50 g, (in terms of the invented compound in the invented controlling agent), per Kg of the seeds.
• the invented controlling agent can be used as a composition for controlling plant diseases in crop lands such as upland field, paddy field, lawn, and orchard, etc.
• the present controller can control plant diseases in crop lands where the following "crops" or the like are cultivated.
• Field crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, rape, sunflower, sugar cane, tobacco, etc.
• Vegetables Solanaceae (e.g. eggplant, tomato, green pepper, pepper and potato) , Cucurbotaceae (e.g. cucumber, pumpkin, zucchini, watermelon and melon), Cruciferae (e.g. Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli and cauliflower), Compositae (e.g. edible burdock, garland chrysanthemum, globe artichoke and lettuce), Liliacede (e.g. Welsh onion, onion, garlic and asparagus), Umbelliferae (e.g. carrot, parsley, celery and Pstinaca) , Chenopodiales (e.g. spinach and chard), Lamiaceae (e.g. perilla, mint and basil) , strawberry, sweet potato, Chinese yam, taro, etc.
• Solanaceae e.g. eggplant, tomato, green pepper, pepper and potato
• Cucurbotaceae e.g. cucumber,
• Fruit trees pomaceous fruits (e.g. apple, pear, Japanese pear, Chinese quince and quince) , stone fruits (e.g. peach, plum, nectarine, Japanese apricot, cherry, apricot and prune), citrus fruits (e.g. Satsuma mandarin, orange, lemon, lime and grapefruit) , nut trees (e.g. chestnut, walnut, hazel, almond, pistachio, cashew nut and macadamia nut), berries (e.g. blueberry, cranberry, blackberry and raspberry) , grape, Japanese persimmon, olive, loquat, banana, coffee, date palm, coconut palm, etc.
• pomaceous fruits e.g. apple, pear, Japanese pear, Chinese quince and quince
• stone fruits e.g. peach, plum, nectarine, Japanese apricot, cherry, apricot and prune
• citrus fruits e.g. Satsuma mandarin, orange, lemon
• Trees other than fruit trees tea, mulberry, flowering trees and shrubs, street trees (Japanese ash, birch, flowering dogwood, blue gum, ginkgo, lilac, maple, oak, poplar, Chinese redbud, Formosa sweet gum, plane trees, zelkova, Japanese arborvitae, fir,
• crops also include crops having resistance to herbicides such as HPPD inhibitors (e.g. isoxaflutol) , ALS inhibitos (e.g. imazethapyr and thifensulfuron-methyl) , EPSP synthetase inhibitors, glutamine synthetase inhibitors, bromoxynil, dicamba, etc. which has been imparted by a classic breeding method or a genetic recombination technology.
• HPPD inhibitors e.g. isoxaflutol
• ALS inhibitos e.g. imazethapyr and thifensulfuron-methyl
• EPSP synthetase inhibitors e.g. imazethapyr and thifensulfuron-methyl
• EPSP synthetase inhibitors e.g. imazethapyr and thifensulfuron-methyl
• EPSP synthetase inhibitors e.g. im
• Examples of the "crops" having the resistance imparted by the classic breeding method include Clearfield canola® resistant to imidazolinone herbicides (e.g. imazethapyr) and STS soybean resistant to sulfonylurea ALS inhibition type herbicides (e.g. thifensulfuron-methyl) .
• crops having the resistance imparted by the genetic recombination technology corn cultivars resistant to glyphosate and glafosinate are exemplified and are already on the market under the trade names of RoundupReady®, RoundupReady 2® and LibertyLink®.
• crops also include crops which a genetic recombination technology has enabled to synthesize a selective toxin known in the case of, for example, Bacillus.
• toxins produced in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; insecticidal proteins such as ⁇ -endotoxins (e.g. CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl and Cry9C) , VIPl, VIP2, VIP3, VIP3A, etc., which are derived from Bacillus thuringiensis; toxins derived from nematodes; toxins produced by animals, such as scorpion toxin, spider toxin, bee toxin, insect-specific neurotoxins, etc.; filamentous fungi toxins; plant lectins; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors, etc.
• ⁇ -endotoxins e.g. CrylAb, CrylAc, CrylF, Cryl
• ribosome- inactivating proteins such as ricin, corn-RIP, abrin, rufin, sapolin, priodin, etc.
• steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid- UDP-glucosyltransferase, cholesterol oxidase, etc.
• ecdysone inhibitors HMG-COA reductase
• ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors, etc.
• juvenile hormone esterase diuretic hormone receptors
• stilbene synthetase bibenzyl synthetase
• chitinase and glucanase.
• the toxins produced in such genetically modified crops also include hybrid toxins, partly deficient toxins and modified toxins of insecticidal proteins such as ⁇ -endotoxin proteins (e.g. CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl and Cry9C) , VIPl, VIP2, VIP3, VIP3A, etc.
• the hybrid toxins are produced by a novel combination of the different domains of such a protein by adopting a recombination technology.
• the partly deficient toxin CrylAb deficient in a part of the amino acid sequence is known.
• the modified toxins one or more amino acids of a natural toxin have been replaced.
• the toxins contained in such genetically modified plants impart resistance to insect pests of
• Genetically modified plants containing one or more insecticidal insect-resistant genes and capable of producing one or more toxins have already been known, and some of them are on the market.
• Examples of such genetically modified plants include YieldGard® (a corn cultivar capable of producing CrylAb toxin) , YieldGard Rootworm® (a corn cultivar capable of producing Cry3Bbl toxin) , YieldGard Plus® (a corn cultivar capable of producing CrylAb and Cry3Bbl toxins) , Herculex I® (a corn cultivar capable of producing phosphinotrysin N- acetyltransferase (PAT) for imparting resistance to CrylFa2 toxin and Glyfosinate) , NuCOTN33B (a cotton cultivar capable of producing CrylAc toxin) , Bollgard I® (a cotton cultivar capable of producing CrylAc toxin) , Bollgard II® (a cotton cultivar capable of producing CrylAc and Cry
• crops also include crops having an ability to produce an anti-pathogenic substance having selective action which has been imparted by a gene recombination technology.
• PR proteins and the like are known (PRPs, EP-A-O 392 225) .
• PRPs EP-A-O 392 225
• Such anti-pathogenic substances and genetically modified plants capable of producing them are described in EP-A-O 392 225, WO 95/33818, EP-A-O 353 191, etc.
• anti-pathogenic substances produced by the genetically modified plants include exemplified ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (for example, KPl, KP4 and KP ⁇ toxins produced by viruses are known), etc.; stilbene synthases; bibenzyl synthases; chitinase; glucanase; PR proteins; and anti- pathogenic substances produced by microorganisms, such as peptide antibiotics, antibiotics having a heterocyclic ring, protein factors concerned in resistance to plant diseases (which are called plant- disease-resistant genes and are described in WO 03/000906), etc. [0042]
• ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (for example, KPl, KP4 and KP ⁇ toxins produced by viruses are known), etc.
• stilbene synthases such as sodium channel inhibitors, calcium channel inhibitors (for example, KPl, KP4 and KP ⁇ toxins produced by viruses are known), etc.
• the above-mentioned "crops” also include crops having two or more properties relating to the above-mentioned herbicide resistance, insect pest resistance, disease resistance and the like, which have been imparted by a classic breeding technique or a genetic recombination technology; and crops having two or more properties derived from parents which have been imparted by mating between genetically modified plants having the same or different properties.
• Plant diseases controllable by the present invention include, for example, fungal diseases. More particularly, the diseases described below can be exemplified as the plant diseases. The plant diseases are not limited to them.
• the invented controlling method is usually practiced by applying the invented controlling agent by the above-mentioned method for applying the invented controlling agent.
• Blast Magnetic rust (Magnaporthe grisea) , Helminthosporium leaf spot (Cochliobolus miyabeanus) , sheath blight (Rhizoctonia solani) and "Bakanae” disease (Gibberella fujikuroi) of rice; powdery mildew (Erisiphe graminis) , scab (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale) , rust (Puccinia striiformis, P. graminis, P. recondite, P.
• blossom blight (Monilinia mali) , canker (Valsa ceratosperma) , powdery mildew (Podosphaera leucotricha) , Alternaria leaf spot (Alternaria alternateate apple pathotype) , scab (Venturia inaqualis) and anthracnose (Glomerella cingulata) of apple; scab (Venturia nashicola, V.
• anthracnose (Elsinoe ampelina) , ripe rot (Glomerella cingulata) , powdery mildew (Uncinula necator) , rust (Phakopsora ampelopsidis) , black rot (Guignardia bidwellii) and downy mildew (Plasmopara viticola) of grape; anthracnose (Gloeosporium kaki) and leaf spot (Cercospora Mycosphaerella nawae) of Japanese persimmon; anthracnose (Colletotrichum lagenarium) , powdery mildew (Sphaerotheca fuliginea) , gummy stem blight (Mycosphaerella melonis) , stem rot (Fusarium oxyspoxum) , downy mildew (Pseudoperonospora cubensis) , Phytophthora
• the solid formed was collected by filtration, washed successively with water, cold MTBE, cold ethanol and cold MTBE, and then dried to obtain 0.45 g of N- (5- phenyl) pentyl-quinoline-6-carboxamide (hereinafter referred to as the invented compound 1) .
• the invented compound 1 N- (5- phenyl) pentyl-quinoline-6-carboxamide
• the solid formed was collected by filtration, washed successively with water, cold MTBE, cold ethanol and cold MTBE, and then dried to obtain 0.59 g of N- (4- phenoxy) butyl-quinoline-6-carboxamide (hereinafter referred to as the invented compound 3) .
• the invented compound 3 N- (4- phenoxy) butyl-quinoline-6-carboxamide (hereinafter referred to as the invented compound 3) .
• the solid formed was collected by filtration, washed successively with water, cold MTBE, cold ethanol and cold MTBE, and then dried to obtain 0.56 g of N- (4- phenoxy-2-butenyl) -quinoline-6-carboxamide (hereinafter referred to as the invented compound 4) .
• the invented compound 4 N- (4- phenoxy-2-butenyl) -quinoline-6-carboxamide (hereinafter referred to as the invented compound 4) .
• the invented compound 4 N- (4- phenoxy-2-butenyl) -quinoline-6-carboxamide
• the solid formed was collected by filtration, washed successively with water, cold MTBE, cold ethanol and cold MTBE, and then dried to obtain 0.54 g of N- (4- phenoxy-2-butynyl) -quinoline-6-carboxamide (hereinafter referred to as the invented compound 5) .
• the invented compound 5 N- (4- phenoxy-2-butynyl) -quinoline-6-carboxamide (hereinafter referred to as the invented compound 5) .
• the solid formed was collected by filtration, washed with water and then cold MTBE, and dried to obtain 0.45 g of N- (3, 7-dimethyl-2, 6-octadienyl) -quinoline-6- carboxamide (hereinafter referred to as the invented compound 6) .
• the invented compound 6 N- (3, 7-dimethyl-2, 6-octadienyl) -quinoline-6- carboxamide
• the residue was subjected to silica gel column chromatography to obtain 1.10 g of N- (3,7- dimethyl) octyl-quinoline- ⁇ -carboxamide (hereinafter referred to as the invented compound 8) .
• the invented compound 8 N- (3,7- dimethyl) octyl-quinoline- ⁇ -carboxamide (hereinafter referred to as the invented compound 8) .
• the residue was subjected to silica gel chromatography to obtain 0.45 g of N- (5-phenyl)pentyl- [1, 5] naphthyridine-2-carboxamide (hereinafter referred to as the invented compound 14) .
• the invented compound 14 N- (5-phenyl)pentyl- [1, 5] naphthyridine-2-carboxamide (hereinafter referred to as the invented compound 14) .
• the invented compound 14 N- (5-phenyl)pentyl- [1, 5] naphthyridine-2-carboxamide
• the residue was subjected to silica gel chromatography to obtain 0.17 g of N- (4-phenoxy-2- butynyl) - [1, 5] na ⁇ hthyridine-2-carboxamide (hereinafter referred to as the invented compound 16) .
• the invented compound 16 N- (4-phenoxy-2- butynyl) - [1, 5] na ⁇ hthyridine-2-carboxamide (hereinafter referred to as the invented compound 16) .
• the invented compound 16 N- (4-phenoxy-2- butynyl) - [1, 5] na ⁇ hthyridine-2-carboxamide
• the residue was subjected to silica gel chromatography to obtain 0.13 g of N- (4-phenoxy-2- butenyl) -benzothiazole-6-carboxamide (hereinafter referred to as the invented compound 19) .
• the invented compound 19 N- (4-phenoxy-2- butenyl) -benzothiazole-6-carboxamide (hereinafter referred to as the invented compound 19) .
• the residue was subjected to silica gel chromatography to obtain 95 mg of N- (4-phenoxy-2- butynyl) -benzothiazole-6-carboxamide (hereinafter referred to as the invented compound 20) .
• the invented compound 20 N- (4-phenoxy-2- butynyl) -benzothiazole-6-carboxamide (hereinafter referred to as the invented compound 20) .
• the invented compound 20 N- (4-phenoxy-2- butynyl) -benzothiazole-6-carboxamide
• the residue was subjected to silica gel chromatography to obtain 0.45 g of N- (3, 7-dimethyl-2- octenyl) -quinoline-6-carboxamide (hereinafter referred to as the invented compound 21) .
• the invented compound 21 N- (3, 7-dimethyl-2- octenyl) -quinoline-6-carboxamide
• the residue was subjected to silica gel chromatography to obtain 0.45 g of N- (3, 7-dimethyl-2- octenyl) -benzothiazole-6-carboxamide (hereinafter referred to as the invented compound 22) .
• the invented compound 22 N- (3, 7-dimethyl-2- octenyl) -benzothiazole-6-carboxamide
• H OC H 2 C H C (C H S )CH 2 CH 2 CH 2 C H (C H 3 ) 2
• Wettable powders of each of the invented compounds 1 to 22 are obtained by thoroughly grinding and mixing 50 parts of each of the invented compounds, 3 parts of calcium lignosulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of ' synthetic hydrated silicon dioxide.
• Flowable concentrates of each of the invented compounds 1 to 22 are obtained by mixing 20 parts of each of the invented compounds and 1.5 parts of sorbitan trioleate with 28.5 parts of an aqueous solution containing 2 parts of a poly (vinyl alcohol), finely grinding the resultant mixture by a wet grinding method, adding thereto 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate, and then 10 parts of propylene glycol, and stirring and mixing the resulting mixture. [0076]
• Dusts of each of the invented compounds 1 to 22 are obtained by thoroughly grinding and mixing 2 parts of each of the invented compounds, 88 parts of kaolin clay and 10 parts of talc.
• Emulsifiable concentrates of each of the invented compounds 1 to 22 are obtained by thoroughly mixing 5 parts of each of the invented compounds, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene. [0078] Formulation Example 5
• Granules of each of the invented compounds 1 to 22 are obtained by thoroughly grinding and mixing 2 parts of each of the invented compounds, 1 part of synthetic hydrated silicon dioxide, 2 parts of calcium lignosulfonate, 30 parts of bentonite and 65 parts of kaolin clay, thoroughly kneading the resultant mixture with water, and granulating and drying the kneaded product.
• Formulations of each of the invented compounds 1 to 22 are obtained by mixing 10 parts of each of the invented compounds, 35 parts of white carbon containing polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water, and finely grinding the resultant mixture by a wet grinding method.
• test examples demonstrate that the invented compounds are useful for controlling plant diseases .
• the controlling effect was evaluated by visually observing the area of lesions on each of test plants at the time of investigation and comparing the area of lesions on a plant treated with the invented compound with the area of lesions on an untreated plant.
• Each of plastic pots was filled with sandy loam and sown with cucumber (cultivar: Sagamihanjiro) , followed by growing in a greenhouse for 12 days.
• Each of the invented compounds 1, 2, 4 to 7, 9 to 12, 15 to 18, 21 and 22 was formulated into a flowable concentrate according to Formulation Example 6.
• the flowable concentrate was diluted to a predetermined concentration (500 ppm) with water, and foliage application of the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown cucumber young seedling. After the foliage application, the plant was air-dried and PDA medium containing hyphae of stem rot fungus was placed on the surfaces of the cucumber leaves.
• the plant was grown at 18 0 C and a high humidity for 4 days. Then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the invented compounds 1, 2, 4 to 7, 9 to 12, 15 to 18, 21 and 22 was 30% or less of the area of lesions on an untreated plant .
• Test Example 2 Preventive effect on cucumber gray mold (Botrytis cinerea)
• Each of plastic pots was filled with sandy loam and sown with cucumber (cultivar: Sagamihanjiro) , followed by growing in a greenhouse for 12 days.
• Each of the invented compounds 1, 4, 6, and 14 to 18 was formulated into a flowable concentrate according to Formulation Example 6.
• the flowable concentrate was diluted to a predetermined concentration (500 ppm) with water, and foliage application of the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown cucumber young seedling.
• the plant was air-dried and PDA medium containing spores of cucumber gray mold fungus was placed on the surfaces of the cucumber leaves.
• the plant was grown at 12°C and a high humidity for 5 days. Then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the invented compounds 1, 4, 6, and 14 to 18 was 30% or less of the area of lesions on an untreated plant.
• Test Example 3 Preventive effect on rice blast (Magnaporthe grisea) Each of plastic pots was filled with sandy loam and sown with rice (cultivar: Nihonbare) , followed by growing in a greenhouse for 20 days. Each of the invented compounds 1, 8, 15, 17, 19, 20 and 22 was formulated into a flowable concentrate according to Formulation Example 6. The flowable concentrate was diluted to a predetermined concentration (500 ppm) with water, and foliage application of the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown rice young seedling.
• a predetermined concentration 500 ppm
• the plant was air-dried and then grown in contact with a rice seedling (cultivar: Nihonbare) infected with blast fungus, for 6 days at 24 0 C and a high humidity in the daytime and at 20 0 C and a high humidity in the nighttime. Then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the invented compounds 1, 8, 15, 17, 19, 20 and 22 was 30% or less of the area of lesions on an untreated plant.
• Test Example 4 Preventive effect on wheat leaf blight (Septoria tritici)
• Each of plastic pots was filled with sandy loam and sown with wheat (cultivar: Apogee) , followed by growing in a greenhouse for 10 days.
• Each of the invented compounds 1, 6 and 13 was formulated into a flowable concentrate according to Formulation Example 6.
• the flowable concentrate was diluted to a predetermined concentration (500 ppm) with water, and foliage application of the dilution was carried out so that the dilution might adhere sufficiently to the surfaces of leaves of the grown wheat young seedling. After the foliage application, the plant was air-dried. After 3 days or 4 days, the plant was inoculated with an aqueous suspension of spores of wheat leaf blight fungus by spraying.
• the plant was grown at 18 0 C and a high humidity for 3 days at first and then grown under illumination for 14 to 18 days. Then, the area of lesions was investigated. As a result, it was found that the area of lesions on the plant treated with each of the invented compounds 1, 6 and 13 was 30% or less of the area of lesions on an untreated plant.

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• Chemical & Material Sciences (AREA)
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• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)
• Quinoline Compounds (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 2008
  • 2008-10-23 WO PCT/JP2008/069706 patent/WO2009057668A1/en not_active Ceased
  • 2008-10-27 JP JP2008275322A patent/JP2009132690A/ja active Pending
  • 2008-10-28 AR ARP080104699A patent/AR069067A1/es unknown
  • 2008-10-30 CL CL2008003259A patent/CL2008003259A1/es unknown

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