JPH10120658A - 4-difluorohalogenomethyl-5-iminomethylpyrimidine derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound useful as a herbicide, a growth-regulating agent of plants and a bactericide. SOLUTION: This compound is expressed by the formula [X is F, Cl, etc.; R is a 1-10C alkyl, phenyl (substituted with a 1-8C alkyl, a 1-8C alkoxy, etc.), etc.; Y is N(R1)R2 (R1 is H, a 1-8C alkyl, etc.; R2 is H, a 1-8C haloalkyl, etc.), NHCH2 CO2 (or a 1-3C alkyl), etc.; R7 is H, a 1-4C alkyl, etc.], and a 4-chloro-4,4- difluoro-2-ethoxymethylene-3-oxobutanoic acid ethyl ester is exemplified. The compound of the formula is obtained by hydrolyzing a 4-haloalkyl-substituted pyrimidine-5-carboxylate under an alkaline condition to form a 4-haloalkyl- substituted pyrimidine-5-carboxylic acid, which is derivatized to an acid chloride by a chlorination agent, condensed with an amine derivative under a basic condition to form an amide, and formed to imidoyl by a chlorination agent, and further reacting with a nucleophilic reagent 'Y' such as N or S.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a herbicide, a plant growth regulator and a fungicide containing a novel 4-difluorohalogenomethyl-5-iminomethylpyrimidine derivative as an active ingredient.

[0002]

BACKGROUND OF THE INVENTION Hitherto, many herbicides and fungicides have been used to protect important crops such as rice, soybean, wheat, corn, cotton, beet and the like from weeds and diseases and to increase the productivity of these important crops. Although drugs have been put to practical use, existing drugs still do not satisfy all required functions. The same applies to plant growth regulators.

It has been known that the compounds of the present invention, in which a hydrogen atom is introduced at the 2-position of the pyrimidine ring, a difluorohalogenomethyl group at the 4-position and an iminomethyl group substituted at the 5-position, exhibit herbicidal, fungicidal and plant growth regulating effects. Not known at all.

[0004]

Means for Solving the Problems The present inventors have proposed a novel 4-
As a result of intensive studies on the herbicidal, fungicidal and plant growth regulating effects of the difluorohalogenomethyl-5-iminomethylpyrimidine derivative, it was found that the compound of the present invention represented by the following formula has excellent herbicidal, fungicidal and plant growth regulating activities. The invention has been completed.

That is, the present invention provides a compound represented by the formula (I):

[0006]

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[Wherein X is a fluorine atom, a chlorine atom, a bromine
Represents an atom or an iodine atom, and R represents C₁-C_TenAlkyl
Group, an optionally substituted phenyl group (provided that
The substituent is C ₁-C₈Alkyl group, C₁-C₈Alkoxy
Group, C₁-C₈Haloalkyl group, halogen atom, cyano
Group, C₁-C₈Haloalkoxy group, nitro group or C₁
-C _FourArbitrarily selected from among alkoxycarbonyl groups
You. ), -Q-substituted phenyl group [Q is saturated or unsaturated
C that may be sum of branches₁-C₆The alkylene chain
And substituted phenyl is phenyl which may be optionally substituted.
(However, the substituent is C₁-C₈Alkyl group, C₁-C
₈Alkoxy group, C₁-C₈Haloalkyl group, halogen
Atom, cyano group, nitro group, C₁-C₈Haloalkoxy
Group or C₁-C_FourAny of the alkoxycarbonyl groups
Selected at will. ). ], -QO-substituted
Nyl group (Q and substituted phenyl group have the same meanings as described above.
I forgot. ), Or optionally substituted unsaturation,
Saturated or partially saturated 5- or 6-membered heterocycle (hetero
Pyridine, pyrimidine, triazine, pyridazi as rings
, Pyrazole, imidazole, oxazole, oxa
Examples include a diazole or thiazole ring. Substituent and
And a halogen atom, C₁-C_FourAlkoxy group, C ₁−
C_FourMay be substituted with an alkyl group or a halogen atom
Phenyl group, C₁-C_FourHaloalkyl group or C₁-C
_FourA haloalkoxy group. ), And Y is-
N (R1) R2 [where R1 is a hydrogen atom, C₁-C₈A
Alkyl group, C _Three-C₈Alkenyl group, C_Three-C₈Archi
Nyl group or C₁-C_FourAlkoxy (C₁-C_Four) Al
R2 represents a hydrogen atom, C 2₁-C₈Alkyl
Group, C₁-C₈Haloalkyl group, C_Three-C₈Alkenyl
Group, C_Three-C₈Alkynyl group, C _Three-C₈Cycloalkyl
Group, C_Three-C₈Cycloalkyl (C₁-C_Four) Archi
Group, C₁-C₈Alkoxy (C₁-C_Four) Alkyl
Group, (C₁-C_FourAlkyl) _TwoAmino (C₁-C_FourA)
Alkyl group, C₁-C₆An alkoxy group, (C₁-C_Four)_ThreeShi
Lil (C₁-C_Four) Alkyl group, (C₁-C_Four) Alkoki
Shi (C₁-C_Four) Alkoxy (C₁-C_Four) Alkyl
Group, substituted phenyloxy (C₁-C_Four) Alkyl groups,
(Phenyl optionally substituted with a halogen atom
The oxy group is referred to as a substituted phenyloxy group. ), 2-Teto
Lahydropyranyl (C₁-C_Four) Alkyl group, 2-tetra
Lahydrofuranyl (C₁-C_Four) Alkyl group, 2,2-
Dimethyl-1,3-dioxolan-4-yl- (C₁−
C_Four) Alkyl group, -Q-0-substituted phenyl group (Q-position
The substituted phenyl group has the same meaning as described above. ), C₁−
C₈Acyl group, C_Two-C₈Alkenyloxy (C₁-C_Four)
Alkyl group, C_Three-C₈Alkynyloxy (C₁-C_FourA)
Alkyl group, C₁-C_FourHaloalkoxy (C₁-C_Four) Archi
Group, [C₁-C_FourAlkoxy (C₁-C_Four) Alkyl)_Two
(C₁-C_Four) Alkyl group, 3-tetrahydrofuranyl
Group, 2,2- (C₁-C_FourAlkoxy)_Two-Cyclohexyl
Group, C₁-C_FourAlkylthio (C₁-C_Four) Alkyl groups,
C₁-C_FourHaloalkoxy (C₁-C_Four) Alkoxy (C₁
-C_Four) Alkyl group, cyano (C₁-C_Four) Alkyl groups,
C₁-C_FourAlkoxycarbonyl (C₁-C_Four) Alkyl
Group, phenyl group optionally substituted (however,
The group is a halogen atom, C₁-C₆Alkyl group, C₁-C_Four
Alkoxy group, C₁-C_FourHaloalkyl group, or C₁
-C_FourArbitrarily selected from haloalkoxy groups. )Also
Is a -Q-substituted phenyl group (Q and substituted phenyl are as defined above.
Represents the same meaning. ). ], -NHOR3
(R3 is C₁-C₈Alkyl group, C_Three-C₈Alkenyl
Group, C_Three-C₈Optional with alkynyl group or halogen atom
Represents a benzyl group which may be substituted. ), -N
HCH_TwoCO_Two(C₁-C_ThreeAlkyl), nitrile group, halo
Gen atom, -NHCON (R4) R5 (R4 and R5 are
Each independently represents a hydrogen atom or C₁-C₈An alkyl group
Express. ), Phthalimide group, morpholino group, 1-imi
Dazolyl group, pyrazol-1-yl group, triazole-
1-yl group, 3- (3-fluoropropyl) thiazoline
-2-imino group, 2- (4-chlorophenyl) -5,6
-Dihydro-1,3,4-oxadiazin-4-yl
Group, -NHN (R4) R5 (R4 and R5 are the same as those described above)
Indicates meaning. ), -NHSO_TwoN (R4) R5 (R
4, R5 has the same meaning as described above. ), -NHCO
_TwoR3 (R3 has the same meaning as described above), -NH
COR3 (R3 has the same meaning as described above), -O
-R2 (R2 has the same meaning as described above), -S-
R2 (R2 has the same meaning as described above) or CH
(R6)_Two(R6 is C₁-C_FourAlkoxycarbonyl group
Or a nitrile group. ) And R7 is a hydrogen atom
Child, C₁-C_FourAlkyl group, C₁-C_FourHaloalkyl group,
Or an optionally substituted phenyl group (substituent
Is a halogen atom, C₁-C_FourAlkyl group, C₁-C_FourAl
Coxy group, C ₁-C_FourHaloalkyl group, or C₁-C_Four
Arbitrarily selected from haloalkoxy groups. )
You. A novel 4-difluorohalogenomethyl-
5-iminomethylpyrimidine derivatives and their salts (hereinafter referred to as
Hereinafter, it is referred to as the compound of the present invention. ), And enable them
Weeding, disinfection, and
And plant growth regulators.

In the compound of the present invention (formula I), when the substituent Y has a nitrogen atom bonded to one hydrogen atom (Y = NH-Z),

[0009]

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[0010] As shown in Scheme 1, it means that it contains tautomers of compounds (A) and (B). When the compound of the present invention (formula I) has optical isomers, diastereomers, and geometric isomers, both the respective mixtures and the respective isolated isomers are included.

[0011]

DETAILED DESCRIPTION OF THE INVENTION In the formula (I), X is a fluorine atom, chlorine atom, bromine atom or iodine atom. Preferably, a chlorine atom and a bromine atom are used. R is methyl, ethyl, isopropyl, propyl, secondary butyl, isobutyl, tertiary butyl, cyclopropyl, pentyl, neopentyl,
Cyclohexyl, cyclopentyl, hexyl, heptyl, octyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,
2-fluorophenyl group, 3-fluorophenyl group, 4
-Fluorophenyl group, 2,4-dichlorophenyl group,
3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 4-trifluoromethylphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-chloro-2-trifluoromethylphenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2, 3-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6
-Dichlorophenyl group, 2,4,6-trichlorophenyl group, 2,4-difluorophenyl group, 3,4-difluorophenyl group, 4-butylphenyl group, 3-trifluoromethoxyphenyl group, 2-trifluoromethoxyphenyl Group, 4-chloro-2-fluorophenyl group, 4-
Isobutylphenyl group, 4-propylphenyl group, 3-
Propylphenyl group, 2-propylphenyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,6-dimethylphenyl group, 2,6-diethylphenyl group, 2,6-dimethoxyphenyl Group, 3-
Methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 3-methoxycarbonylphenyl group, 2
-Ethoxycarbonylphenyl, 4-tert-butoxycarbonylphenyl, 3-tert-butoxycarbonylphenyl, 2-tert-butoxycarbonylphenyl, 4-tert-butoxyphenyl, 4-ethoxyphenyl, 4-butoxy Phenyl group, 4-propoxyphenyl group, 4-isopropoxyphenyl group, 3-isopropoxyphenyl group, 3-ethoxyphenyl group, 1,1-dimethyl-2-phenylethyl group, 1,1-dimethyl-2- ( 4-fluorophenyl)
Ethyl group, 1,1-dimethyl-2- (4-chlorophenyl) ethyl group, 2-chloro-5-trifluoromethylphenyl group, 4-chloro-3-trifluoromethylphenyl group, 2-chloro-4-trifluoromethylphenyl Group,
1,1-dimethyl-2- (2-chlorophenyl) ethyl group, 1,1-dimethyl-2- (3-chlorophenyl) ethyl group, 1,1-dimethyl-2- (2-fluorophenyl) ethyl group, 1 , 1-dimethyl-2- (3-fluorophenyl) ethyl group, 4-methoxy-α-methylbenzyl group, 4-methylphenyl group, 4-nitrophenyl group,
3-nitrophenyl group, 2-nitrophenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 2-cyanophenyl group, 4-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 4-secondary butylphenyl group, 4-
Trifluoromethoxyphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group,
Cumyl, benzyl, 4-chlorobenzyl, 3-chlorobenzyl, 2-chlorobenzyl, 4-fluorobenzyl, α-methylbenzyl, 3-fluorobenzyl, 2-fluorobenzyl, 4- Chlorocumyl group, 4-fluorocumyl group, 2-chloro-α-methylbenzyl group, 2-chloro-α-methylbenzyl group, 3-chloro-α-methylbenzyl group, 4-chloro-α-methylbenzyl group, Fluoro-α-methylbenzyl group, 3
-Fluoro-α-methylbenzyl group, 4-fluoro-α
-Methylbenzyl group, phenethyl group, 2-methylphenethyl group, 2-chlorophenethyl group, 3-chlorophenethyl group, 3-methylphenethyl group, 4-methylphenethyl group, 4-cyanophenethyl group, 4-chlorophenethyl group, 2-fluorophenethyl group, 3-fluorophenethyl group, 4-fluorophenethyl group, 2-methoxyphenethyl group, 3-methoxyphenethyl group, 4-methoxyphenethyl group, 2,4-dichlorophenethyl group, 3,4-dichlorophenethyl Group, 2-trifluoromethylphenethyl group, 3-trifluoromethylphenethyl group, 4-trifluoromethylphenethyl group, 2- (2-phenoxy)
Ethyl group, 2- (2-chlorophenoxy) ethyl group, 2
-(3-chlorophenoxy) ethyl group, 2- (4-chlorophenoxy) ethyl group, 2- (2,4-dichlorophenyl) ethyl group, 2- (3,4-dichlorophenyl) ethyl group, 2- (2 4,6-trichlorophenyl) ethyl group, 2- (2,6-dichlorophenyl) ethyl group, 2
-Pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-
Pyrimidyl group, 4-pyrimidyl group, 4,6-dimethoxypyrimidin-2-yl group, 1-methylpyrazole-3-
Yl group, 1-methylpyrazol-4-yl group, 1-methylpyrazol-5-yl group, 4-chloro-2-pyridyl group, 1-methyl-3-trifluoromethylpyrazole-
4-yl group, 1-methyl-3-trifluoromethylpyrazol-5-yl group, 5-tert-butyl-1,
3,4-oxadiazol-2-yl group, 4,6-dimethoxy-1,3,5-triazin-2-yl group, 3-phenylpropyl group, 1-methyl-2-phenylethyl group, 1- A methyl-2- (4-chlorophenyl) ethyl group, a 1-methyl-2- (3-chlorophenyl) ethyl group, a 1-methyl-2- (4-methoxyphenyl) ethyl group, and a 1-methyl-2- (3 -Methoxyphenyl)
Ethyl groups are mentioned.

Examples of Y include the following substituents.
NHMe, NHEt, NHPr, NHPr^iso, NHB
u, NHBu^sec, NHBu^tert, NHBu^iso, NH
CH _TwoCH = CH_Two, NHCH_TwoC≡CH, NHCH
(Me) CH = CH_Two, NHHex, NHCH (Me)
C≡CH, NHC (Me)_TwoC≡CH, NHC (Me)
_TwoCH = CH_Two, C≡N, NH_Two, N (Me)_Two, N
(Et)_Two, N (Pr)_Two, N (Pr^iso)_Two, N (C
H_TwoCH = CH_Two)_Two, N (CH_TwoC≡CH)_Two, NH
Ph, NH- (2-Cl-Ph), NH- (3-Cl-
Ph), NH- (4-Cl-Ph), NH- (2-F-
Ph), NH- (3-F-Ph), NH- (4-FP)
h), NH- (2-Br-Ph), NH- (3-Br-
Ph), NH- (4-Br-Ph), NH- (2-Me
-Ph), NH- (3-Me-Ph), NH- (4-M
e-Ph), NH- (2-MeO-Ph), NH- (3
-MeO-Ph), NH- (4-MeO-Ph), NH
− (2-CF_Three-Ph), NH- (3-CF_Three−P
h), NH- (4-CF_Three-Ph), NH- (2-NO
_Two-Ph), NH- (3-NO_Two-Ph), NH- (4
-NO_Two-Ph), NH- (2-CF_ThreeO-Ph), N
H- (3-CF_ThreeO-Ph), NH- (4-CF_ThreeO-
Ph), NH- (2,4-Cl_Two-Ph), NH-
(3,4-Cl_Two-Ph), NH- (2,3-Cl_Two−
Ph), NH- (2,5-Cl_Two-Ph), NH-
(2,6-Cl_Two-Ph), NH- (3,5-Cl_Two−
Ph), NHCH_TwoPh, NHCH_Two-(2-Cl-P
h), NHCH_Two-(3-Cl-Ph), NHCH_Two−
(4-Cl-Ph), NHCH_Two-(2-F-Ph),
NHCH_Two-(3-F-Ph), NHCH_Two− (4-F
-Ph), NHCH_Two-(2-Br-Ph), NHCH
_Two-(3-Br-Ph), NHCH_Two-(4-Br-P
h), NHCH_Two-(2-Me-Ph), NHCH_Two−
(3-Me-Ph), NHCH_Two-(4-Me-P
h), NHCH_Two-(2-MeO-Ph), NHCH_Two
-(3-MeO-Ph), NHCH_Two-(4-MeO-
Ph), NHCH_Two− (2-CF _Three-Ph), NHCH
_Two− (3-CF_Three-Ph), NHCH_Two− (4-CF_Three
-Ph), NHCH_Two− (2-CF_ThreeO-Ph), N
HCH_Two− (3-CF_ThreeO-Ph), NHCH_Two− (4
-CF_ThreeO-Ph), NHCH_Two-(2-NO_Two−P
h), NHCH_Two-(3-NO_Two-Ph), NHCH_Two
-(4-NO_Two-Ph), NHCH_Two-(2,4-Cl
_Two-Ph), NHCH_Two-(3,4-Cl_Two-Ph),
NHCH_Two-(2,3-Cl_Two-Ph), NHCH_Two−
(2,5-Cl _Two-Ph), NHCH_Two-(2,6-C
l_Two-Ph), NHCH_Two-(3,5-Cl_Two−P
h), NHCH_Two-(2-F-4-Cl-Ph), NH
CH_Two-(3-F-4-Cl-Ph), NHCH_Two−
(2,6-F_Two-Ph), NHCH_Two− (3,4-F_Two
-Ph), NHCH_Two− (2,4-F_Two-Ph), NH
CH_Two-(3-Me-4-F-Ph), NHCH_Two−
(3-Me-4-Cl-Ph), NHOMe, NHOE
t, NHOPr, NHOPr^iso, NHOCH_TwoCH =
CH _Two, NHOCH_TwoC≡CH, NHOBu, NHOC
H_TwoPh, NHOCH_Two-(4-Cl-Ph), NHO
CH_Two-(3-Cl-Ph), NHOCH_Two− (2-C
1-Ph), OMe, OEt, OPr, OPr^iso, O
Bu, OBu^sec, OBu^tert, OBu^iso, OCH_Two
CH = CH_Two, OCH_TwoC≡CH, OCH (Me) CH
= CH_Two, OHex, OCH (Me) C≡CH, OC
(Me)_TwoC≡CH, OC (Me)_TwoCH = CH_Two, O
Ph, O- (2-Cl-Ph), O- (3-Cl-P
h), O- (4-Cl-Ph), O- (2-FP)
h), O- (3-F-Ph), O- (4-F-Ph),
O- (2-Br-Ph), O- (3-Br-Ph), O
-(4-Br-Ph), O- (2-Me-Ph), O-
(3-Me-Ph), O- (4-Me-Ph), O-
(2-MeO-Ph), O- (3-MeO-Ph), O
-(4-MeO-Ph), O- (2-CF_Three-Ph),
O- (3-CF_Three-Ph), O- (4-CF_Three−P
h), O- (2-NO_Two-Ph), O- (3-NO_Two−
Ph), O- (4-NO_Two-Ph), O- (2-CF_Three
O-Ph), O- (3-CF_ThreeO-Ph), O- (4-
CF_ThreeO-Ph), O- (2,4-Cl_Two-Ph), O
-(3,4-Cl_Two-Ph), O- (2,3-Cl_Two−
Ph), O- (2,5-Cl_Two-Ph), O- (2,6
-Cl_Two-Ph), O- (3,5-Cl)_Two-Ph), O
− (2,6-F_Two-Ph), O- (2,4-F) _Two−P
h), O- (3,4-F)_Two-Ph), O- (2-F-4)
-Cl-Ph), OCH_TwoPh, OCH_Two-(2-Cl
-Ph), OCH_Two-(3-Cl-Ph), OCH_Two−
(4-Cl-Ph), OCH_Two-(2-F-Ph), O
CH_Two-(3-F-Ph), OCH_Two-(4-FP
h), OCH_Two-(2-Br-Ph), OCH_Two-(3
-Br-Ph), OCH_Two-(4-Br-Ph), OC
H_Two-(2-Me-Ph), OCH_Two-(3-Me-P
h), OCH_Two-(4-Me-Ph), OCH_Two-(2
-MeO-Ph), OCH_Two-(3-MeO-Ph),
OCH_Two-(4-MeO-Ph), OCH_Two− (2-C
F_Three-Ph), OCH_Two− (3-CF_Three-Ph), OC
H_Two− (4-CF_Three-Ph), OCH_Two− (2-CF_Three
O-Ph), OCH_Two− (3-CF_ThreeO-Ph), OC
H_Two− (4-CF _ThreeO-Ph), OCH_Two-(2-NO
_Two-Ph), OCH_Two-(3-NO_Two-Ph), OCH
_Two-(4-NO_Two-Ph), OCH_Two-(2,4-Cl
_Two-Ph), OCH_Two-(3,4-Cl_Two-Ph), O
CH_Two-(2,3-Cl_Two-Ph), OCH_Two− (2,
5-Cl_Two-Ph), OCH_Two-(2,6-Cl_Two−P
h), OCH_Two-(3,5-Cl_Two-Ph), OCH_Two
-(2-F-4-Cl-Ph), OCH_Two-(3-F-
4-Cl-Ph), OCH_Two− (2,6-F_Two−P
h), OCH_Two− (3,4-F_Two-Ph), OCH_Two−
(2,4-F_Two-Ph), OCH_Two-(3-Me-4-
F-Ph), OCH_Two-(3Me-4-Cl-Ph),
SMe, SEt, SPr, SPr^iso, SBu, SBu
^sec, SBu^tert, SBu^iso, SCH_TwoCH = C
H_Two, SCH_TwoC≡CH, SCH (Me) CH = C
H_Two, SHex, SCH (Me) C≡CH, SC (M
e)_TwoC≡CH, SC (Me)_TwoCH = CH_Two, SP
h, S- (2-Cl-Ph), S- (3-Cl-P
h), S- (4-Cl-Ph), S- (2-FP)
h), S- (3-F-Ph), S- (4-F-Ph),
S- (2-Br-Ph), S- (3-Br-Ph), S
-(4-Br-Ph), S- (2-Me-Ph), S-
(3-Me-Ph), S- (4-Me-Ph), S-
(2-MeO-Ph), S- (3-MeO-Ph), S
-(4-MeO-Ph), S- (2-CF_Three-Ph),
S- (3-CF_Three-Ph), S- (4-CF_Three−P
h), S- (2-NO)_Two-Ph), S- (3-NO_Two−
Ph), S- (4-NO_Two-Ph), S- (2-CF_Three
O-Ph), S- (3-CF_ThreeO-Ph), S- (4-
CF_ThreeO-Ph), S- (2,4-Cl _Two-Ph), S
-(3,4-Cl_Two-Ph), S- (2,3-Cl_Two−
Ph), S- (2,5-Cl_Two-Ph), S- (2,6
-Cl_Two-Ph), S- (3,5-Cl)_Two-Ph), S
− (2,6-F_Two-Ph), S- (2,4-F)_Two−P
h), S- (3,4-F)_Two-Ph), S- (2-F-4)
-Cl-Ph), SCH_TwoPh, SCH_Two-(2-Cl
-Ph), SCH_Two-(3-Cl-Ph), SCH_Two−
(4-Cl-Ph), SCH_Two-(2-F-Ph), S
CH_Two-(3-F-Ph), SCH_Two-(4-FP
h), SCH_Two-(2-Br-Ph), SCH_Two-(3
-Br-Ph), SCH_Two-(4-Br-Ph), SC
H_Two-(2-Me-Ph), SCH_Two-(3-Me-P
h), SCH_Two-(4-Me-Ph), SCH_Two-(2
-MeO-Ph), SCH_Two-(3-MeO-Ph),
SCH_Two-(4-MeO-Ph), SCH_Two− (2-C
F_Three-Ph), SCH_Two− (3-CF_Three-Ph), SC
H_Two− (4-CF_Three-Ph), SCH_Two− (2-CF_Three
O-Ph), SCH_Two− (3-CF_ThreeO-Ph), SC
H_Two− (4-CF_ThreeO-Ph), SCH_Two-(2-NO
_Two-Ph), SCH_Two-(3-NO_Two-Ph), SCH
_Two-(4-NO_Two-Ph), SCH_Two-(2,4-Cl
_Two-Ph), SCH_Two-(3,4-Cl_Two-Ph), S
CH_Two-(2,3-Cl_Two-Ph), SCH_Two− (2,
5-Cl_Two-Ph), SCH_Two-(2,6-Cl_Two−P
h), SCH_Two-(3,5-Cl_Two-Ph), SCH_Two
-(2-F-4-Cl-Ph), SCH _Two-(3-F-
4-Cl-Ph), SCH_Two − (2,6-F_Two −P
h), SCH_Two − (3,4-F_Two -Ph), SCH_Two
 − (2,4-F_Two -Ph), SCH_Two -(3-Me
-4-F-Ph), SCH_Two -(3Me-4-Cl-
Ph), NHCH_TwoCH_TwoOMe, NHCH_TwoCH_TwoOE
t, NHCH_TwoCH_TwoCH_TwoOMe, NHCH_TwoCH_TwoCH_Two
OEt, NHCOMe, NHCOEt, NHCOPr
^iso, NHCOPr, NHCOBu, NHCOBu^sec,
NHCOBu^iso, NHCOBu^tert, NHCO_TwoMe,
NHCO_TwoEt, NHCO_TwoPr, NHCO_TwoPr^iso, N
HCO_TwoBu, NHCO_TwoBu^sec, NHCO_TwoBu^iso,
NHCO_TwoBu^tert, NHNH_Two, NHNHMe, NHN
HEt, NHNHPr, NHNHBu^tert, NHN (M
e)_Two, NHN (Et)_Two, NHN (Pr)_Two, NHN
(Pr^iso )_Two, NH_Two, NHCON (Me)_Two, NHC
ONHMe, NHCONHPr, NHCON (E
t)_Two, NHCONHEt, NHCONHPr^iso, NH
CONHBu^{te rt}, NHCONHBu, NHCONNHB
u^sec, NHCONHBu^iso, NHCONH_Two, NHS
O_TwoNH_Two, NHSO_TwoNHMe, NHSO_TwoNHEt, N
HSO_TwoNHPr, NHSO_TwoNHPr^iso, NHSO_TwoN
HBu, NHSO_TwoNHBu^tert, NHSO_TwoN (Me)
_Two, NHSO_TwoN (Et)_Two, NHSO_TwoN (Pr)_Two, N
HSO_TwoN (Pr^iso )_Two, NHSO_TwoN (Bu)_Two, N
HC (Me)_Two-(4-Cl-Phenyl), NH
C (Me)_Two-(4-F-Phenyl), NHC (M
e)_TwoCH_Two-Phenyl, NHCH (Me)-(4-
Cl-Phenyl), NHCH (Me) -Pheny
1, 1-imidazolyl, pyrazole-1
-Yl, morpholino, triazole-1
-Yl, phtalimido, CH (CO_TwoMe)_Two,
CH (CO_TwoEt)_Two, CH (CN)_Two, OCH_TwoC (M
e)_Three, OC (Me)_TwoEt, OCH (Me) CH_TwoCH_Two
CH_Three, OCH (Et)_Two, OCH (Me) -P
r^cyclo, OPr^cyclo, OHex^cyclo, OPe
n^cyclo, OCH_TwoCH_TwoOMe, OCH_TwoCH_TwoOEt,
OCH_TwoOMe, OCH _TwoOEt, OCH_TwoCH_TwoN (M
e)_Two, OCH (Me) CH_TwoOCH_Three, OCH (Me)
CH_TwoOEt, OCH_TwoC (Me) = CH_Two, OCH_TwoCH
= C (Me)_Two, OCH (Et) CH_TwoCl, OCH (C
H_TwoCl)_Two, OCH_TwoCF_Three, NHOCH_TwoCO_TwoMe, N
HOCH_TwoCO_TwoEt, 3- (3-fluoropropyl) thio
Azoline-2-imino, OPn, OCH_TwoCH_TwoOPr,
OCH_TwoCH_TwoOPr^iso, OCH_TwoCH_TwoOBu, OCH_Two
CH_TwoOBu^iso, OCH_TwoCH_TwoOPr^cyclo, OCH_TwoC
H_TwoOPn^cyclo, OCH_TwoCH_TwoSi (Me)_Three, OCH_Two
CH_TwoOCH_TwoCH_TwoOMe, OCH_TwoCH_TwoOCH_TwoCH_Two
OEt, OCH_TwoCH_TwoOCH_TwoCH_TwoOCH_TwoCH_TwoCl,
OCH_TwoCH_TwoOCH_TwoCH_TwoOPr, OCH_TwoCH_TwoOP
h, OCH_TwoCH_TwoO- (3-F-Ph), OCH_TwoCH_Two
O- (4-Cl-Ph), OCH_TwoCH_TwoO- (2-Cl
-Ph), OCH_TwoCH_TwoO- (3-Cl-Ph), OC
H_TwoCH_TwoO- (4-F-Ph), OCH_TwoCH_TwoO- (2
-F-Ph), OCH_TwoCH (Me) O- (2-Cl-
Ph), OCH_TwoCH (Me) O- (3-Cl-P
h), OCH_TwoCH (Me) O- (4-Cl-Ph),
OCH_TwoCH (Me) OPh, OCH_TwoCH (Me) OM
e, OCH_TwoCH (Me) OEt, OCH_TwoCH (Me)
OPr, OCH_TwoCH (Me) OPn, OCH (Me)
CH_TwoOPh, OCH (Me) CH_TwoOBu, OCH (M
e) CH_TwoOBu^tert, OCH (Me) CH_TwoOMe, O
CH (Me) CH_TwoOEt, OCH (Me) CH_TwoOP
r, OCH (Me) CH_TwoOPn, OCH_TwoCH_TwoCH_TwoO
Me, OCH_TwoCH_TwoCH_TwoOEt, OCH_TwoCH_TwoCH_TwoO
Pr^iso, OCH_TwoCH_TwoCH_TwoOPr, OCH_TwoCH_TwoCH
_TwoOBu, OCH_TwoCH _TwoCH_TwoCH_TwoOMe, OCH_TwoCH
_TwoCH_TwoCH_TwoOEt, OCH_TwoCH_TwoCH_TwoCH_TwoOP
r^iso, OCH_TwoCH_TwoCH_TwoCH_TwoOPr, OCH_TwoCH_Two
CH_TwoCH_TwoOBu, OCH_TwoCH_TwoCH_TwoCH_TwoCH_TwoOM
e, OCH_TwoCH_TwoCH_TwoCH_TwoCH_TwoOEt, OCH_TwoCH
_TwoOCH_TwoCH = CH_Two, OCH_TwoCH_TwoOCH_TwoC≡CH,
OCH_TwoCH_TwoOCH (Me) CH = CH_Two, OCH_TwoCH
_TwoOC (Me)_TwoCH = CH_Two, OCH_TwoCH_TwoOCH_TwoCH
_TwoCl, OCH_TwoCH_TwoOCH = CH_Two, OCH (CH_TwoO
Me)_Two, OCH (CH_TwoOEt)_Two, OCH (Me) C
H_TwoO- (2-Cl-Ph), OCH (Me) CH_TwoO-
(3-Cl-Ph), OCH (Me) CH_TwoO- (4-
Cl-Ph), OCH (Et) CH_TwoOMe, OCH
(Et) CH_TwoOEt, OCH _TwoCH_TwoSMe, OCH_TwoC
H_TwoSEt, OCH_TwoCH_TwoSPr, OCH_TwoCH_TwoSPr
^iso, OCH_TwoCH_TwoCH_TwoCl, OCH_TwoCH_TwoCl, OC
H_TwoCH_TwoCH_TwoCH_TwoCl, OCH_TwoCH_TwoCHCl_Two, O
COMe, OCOEt, OCOPr, OCOPr^{i so},
OCOBu, OCOBu^sec, OCOBu^iso, OCOB
u^tert, OCOPn, OCOPn^cyclo, OCOPr
^cyclo, OCOHex, Q¹, Q^Two, Q^Three, Q^Four, Q ^Five,Also
Is Q⁶.

R7 includes the following substituents.
Hydrogen atom, Me, Et, Pr, Pr ^iso , Bu, B
u ^sec , Bu ^iso , Bu ^tert , Ph, 2-Cl-Phen
yl, 3-Cl-Phenyl, 4-Cl-Pheny
1, 2-F-Phenyl, 3-F-Phenyl, 4
-F-Phenyl, 2-CF ₃ -Phenyl, 3-
_{CF 3 -Phenyl, 4-CF 3} -Phenyl, 2-
Me-Phenyl, 3-Me-Phenyl, 4-M
e-Phenyl, 2-MeO-Phenyl, 3-M
eO-Phenyl, 4-MeO-Phenyl, 2-
CF ₃ O-Phenyl, 3-CF ₃ O-Phenyl,
_{4-CF 3 O-Phenyl,} CF 3, CH 2 CH 2 Cl,
CH ₂ Cl, CF ₂ Cl, CH ₂ CH ₂ Br, or CF ₂
H.

Incidentally, the symbols of the sentences have the following meanings. Ph:
Phenyl, Me: CH_Three, Et: C_TwoH_Five, Pr, P
rⁿ: CH_TwoCH_TwoCH_Three, Pr^iso: CH (C
H_Three)_Two, Pr^cyclo: CH (CH_Two)_Two, Bu, B
uⁿ: CH_TwoCH_TwoCH_TwoCH_Three, Bu ^sec: CH (C
H_Three) C_TwoH_Five, Bu^iso: CH_TwoCH (CH_Three)_Two, B
u^tert: C (CH_Three)_Three, Bu^cyclo: CH (C
H_Two)_Three, Pn, Pnⁿ: CH_TwoCH_TwoCH_TwoCH_TwoC
H_Three, Pn^cyclo: CH (CH_Two)_Four, Pn^iso: CH_Two
CH_TwoCH (CH_Three)_Two, Pn^neo: CH_TwoC (C
H_Three)_Three, Hex, Hexⁿ: CH_Two(CH_Two)_FourC
H_Three, Hep, Hepⁿ: CH_Two(CH_Two)_FiveCH_Three, O
ct, Oct ⁿ: CH_Two(CH_Two)₆CH_Three, 4-Cl
-Ph: 4-Cl-Phenyl.

Q ¹ to Q ⁶ represent the following substituents.

[0016]

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Some of the compounds of the present invention are used as herbicides for upland fields and non-cultivated lands, such as Solanum nigrum , Datura stramonium, etc. in any of soil treatment and foliage treatment. Solanaceae
(Solanaceae) weeds, Malvaceae weeds represented by scabs (Abutilon theophrasti) , American sika deer (Sida spinosa), etc., and Malva Asagao ( Ipomoea purpu
rea) morning glory such as (Ipomoe a spps.) and Morning Glory acids (Calystegia spps.) family Convolvulaceae represented by such (Conv
olvulaceae) Weeds, Amaranthus lividus ,
Amaranthaceae weeds represented by Amaranthus retroflexus, etc., and Xanthium pen
sylvanicum , ragweed ( Ambrosia artemisiaefoli )
a), sunflower (Helianthus annuus), galinsoga quadriradiata (Ga
linsoga ciliata) , thistle (Cirsium arve)
nse), Novorogi ( Senecio vulgaris ), Himejon
Asteraceae (Composita) represented by ( Erigeron annus )
e) Weeds, dog puppies ( Rorippa indica ), wild puppies ( Sinapis arvensis ), and rapes ( Capsella Bursapast )
oris ), Brassicaceae (Cruciferae) weed, Polygonum Blumei , Polygonu
m convolvulus) and other Polygonaceae (Polygonaceae)
Weeds, Pursaceae (Portulacaceae) weeds represented by purslanes ( Portulaca oleracea ), etc.
odium album) , core kaza ( Chenopodium ficifolium ),
Red crab (Cochia scoparia )
henopodiaceae) weeds, Caryophyllaceae weeds such as Stellaria media, Scrophulariaceae weeds such as Veronica persica , and communis.
a communis ) etc. (Commelinacea
e) Weeds, Labiatae weeds, represented by Lamium amplexicaule , Lamium purpureum, etc. Weeds, Euphorbia supina
Euphorbia maculata, Euphorbia maculata, etc., Euphorbiaceae weed, Galium spurium , Rubia akane, etc., Rubiaceae weed, Viola mand
shurica) and other legumes ( Legumi) such as Violaceae weeds, Sesbania exaltata , and Cassia obtusifolia.
nosae) broad-leaved weeds such as weeds (Broad-leaved weeds), wild sorghum (Sorgham bicolor), fall panicum (Panicum di
chotomiflorum) , Johnsongrass ( Sorghum halepens)
e) , dog millet (Echinochloa crus-galli var. crus-gal
li) , Echinochloa crus-galli var. pra
ticola) , cultivated flies (Echinochloa utilis) , crabgrass ( Digitaria adscendens ), oats ( Avenafatu )
a) , Hawkgrass (Eleusine indica ), Enokorogosa ( Se
taria viridis) , Sparrow-nosed Ephemer ( Alopecurus aegua )
lis) and other grass weeds (Graminaceous weeds)
, Daylily ( Cyperus rotundus, Cyperus esculentus )
Cyperaceous wee (Cyperaceous wee)
ds) and other various field weeds (Cropland weeds) have low herbicide and high herbicidal activity.

[0018] In addition, as a herbicide for paddy fields, both in soil treatment and foliage treatment under flooded conditions, it is possible to use a hermit mosquito ( Alisma canaliculatum ) or a mosquito ( Sagittaria ).
trifolia) , weeds ( Sagittaria pygmaea ), and other weeds (Alismataceae) weeds; cyperus difformis ; and Cyperus seroti
nus) , Firefly (Scirpus juncoides) , Krogwai ( El
eocharis kuroguwai) Cyperaceae represented by, etc. (Cyperaceae) weed, false pimpernel (Scrophulariaceae represented by Lindemia pyxidaria), etc. (Scrothulariaceae) weeds, pontederiaceae represented by Monochoria (Monochoria vaginalis), etc. (Potenderiaceae) weed, pondweed ( Pota
mogeton distinctus )
amogetonaceae), Lythraceae weed represented by Rotala indica, etc., Echinochloa oryzicola , Echino millet ( Echino )
chloa crus-galli var. formosensis) , barnyardgrass (Echi
nochloa crus-galli var. crus-galli ) Weeds, etc.
Paddy weeds have high herbicidal activity at low dose.

Some of the compounds of the present invention include important crops such as rice, wheat, barley, sorghum, peanuts,
Highly safe against corn, soybeans, cotton, beets, etc. Some of the compounds of the present invention exhibit a strong plant growth regulating action. Also surprisingly, the compounds according to the invention show an excellent microbicidal action and can be used as fungicides in plant protection and substance storage. It has preventive, curative or systemic control effects on many plant diseases.

Next, the plant diseases targeted by the compound of the present invention include rice blast ( Pyricularia oryzae) , sesame leaf blight ( Cochliobolus miyabeanus) , and sheath blight (Rhizoc )
tonia solani ), wheat powdery mildew (Erysiphe gram)
inis f.sp. hordei, f. sp .tritici ), Madarahabyo (Pyrenoph
ora graminea ), net spot (Pyrenophora teres ), red mold (Gibberella zeae ), rust ( Puccinia striiformi)
s , P.graminis, P.recondita, P.hordei) , snow rot (Typh
ula sp. , Micronectriella nivais) , naked smut ( Ustilag
o tritici, U.nuda) , Eye spot (Pseudocercosporell )
a herpotrichoides ), scald ( Rhynchosporium secali)
s ), leaf blight (Septoria tritici) , blight ( Leptosphaeri )
a nodorum) ,

[0021] Citrus black spot ( Diaporthe citri) , scab (Elsinoe fawcetti) , fruit rot ( Penicillium)
digitatum, P.italicum ) , monilia disease of apple (Scler
otiniamali) , rot ( Valsa mali ), powdery mildew (P
odosphaera leucotricha) , spotted leaf spot ( Alternaria ma
li) , scab ( Venturia inaequalis ), pear scab
(Venturia nashicola) , Black spot ( Alternaria Kikuchia
na ), scab (Gymnosporangium haraeanum ), peach scab (Sclerotinia cinerea ), scab (Cladosporium ca)
rpophilum), Phomopsis rot (Phomopsis sp.), grape downy mildew (Plasmopara viticola), sphaceloma disease (Elsi
noe ampelina ), late rot ( Glomerella cingulata) , powdery mildew (Uncinula necator) , rust ( Phakopsora amp)
elopsidis) , oyster anthracnose ( Gloeosporium kaki ), deciduous disease (Cercospora kaki, Mycosphaerella nawae ),

Downy mildew of cucumber (Pseudoperenospora cuben)
sis) , anthracnose ( colletotrichum lagenarium) , powdery mildew ( sphaerotheca fuliginea ), vine blight (mycosphaere )
lla melonis ), Tomato blight (Phytophthora infesta)
ns ), Fusarium oxysporum , Ring rot ( Alte
rnaria solani) , leaf mold (Cladosporium fulvam ), eggplant brown spot (Phomopsis vexans) , powdery mildew ( Erysip )
he cichoracoarum ), black spot on cruciferous vegetables ( Altern
aria japonica) , vitiligo (Cerocosporella brassicae) ,
Green onion rust (Puccinia allii), soybean purpura ( Cerc
ospora kikuchii) , black rot ( Elsinoe glycines ), black spot ( Diaporthe phaseololum) , green bean anthracnose ( Co)
lletotrichum (lindemuthianum) , peanut black spot
(Mycosphaerella personatum) , brown spot (Cercospora ara)
chidicola ), pea powdery mildew ( Erysiphe pisi) ,

Summer blight of potato (Alternaria solan
i), Strawberry powdery mildew(Sphaerothecahumuli), Cha
Net blast (Exobasidium reticulatum), White scab(Elsin
oe leucospila)The scab of tobacco (Alternaria longipe
s), Powdery mildew (Erysiphe cichoracearum), Anthracnose
(Colletotrichum tabacum), Brown spot of sugar beet(Cerco
spora beticola), Rose scab(Diplocarpon rosae)
 , Powdery mildew(Sphaerotheca pannosa)Brown spot of chrysanthemum
(Septoria chrysanthemiindici), White rust (Puccinia
horiana), Brown patch of bentgrass (Phizoctoni
a solani), Picium bright(Pythium spp.), Dollar
spot(Sclerotinia homoeocarpa), Various snow rots(Typ
hula spp,Fusarium nivale,(Sclerotinia borealis)
 , Hermint sporium disease(Helminthosporium soroki
nianum, H. erythrospilum), Nosy,
Various picium diseases(Pythium periplocum,P. graminicola,
P. vanterpoolii), Leaf rot(Rhizoctonia solani),seed
Gray mold on various crops (Botrytis cinerea), Sclerotium disease
(Sclerotinia sclerotiorum) And the like.

Accordingly, the compound of the present invention can be used as an active ingredient of a fungicide for agricultural and horticultural use in upland fields, paddy fields, turf, orchards, pastures, greenhouses and other non-cultivated lands. The compound of the present invention can be synthesized, for example, by the method shown in Scheme 2 (X, Y, R7 and R in Scheme 2 represent the same meaning as described above, and Ra, Rb, R ′, and R ″ are each independently It represents a C ₁ -C ₄ alkyl group.).

[0025]

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4-haloalkyl-substituted pyrimidine-5-carboxylic acid ester (V) which is an intermediate of the compound of the present invention
Is obtained by reacting a β-keto acid ester (II) with, for example, an orthoformate to form an α-alkoxymethylene-β-keto acid ester (III) and then reacting with a formamidine or a β-keto acid ester (II) is reacted with, for example, N, N-dimethylformamide dialkyl acetal or tert-butoxy-bis (dimethylamino) methane to form α-dimethylaminomethylene-β-keto acid ester (IV), and then with formamidines It can be synthesized by reacting.

The 4-haloalkyl-substituted pyrimidine-5-carboxylic acid ester (V) thus obtained is hydrolyzed under alkaline conditions to give a 4-haloalkyl-substituted pyrimidine-5-carboxylic acid (VI). The amide (VII) is obtained by condensing the corresponding acid chloride with a suitable chlorinating agent such as thionyl chloride or phosphorus oxychloride under basic conditions with an amine derivative. Next, the compound of the present invention (I) is reacted with a chlorinating agent such as phosphorus pentachloride to give imidoyl chloride (VIII), and then reacted with a nucleophile "Y" (for example, N, S, O, C, etc.). ) Can be manufactured.

The synthesis examples of the compounds of the present invention and intermediates are specifically described below by way of examples, but the present invention is not limited thereto.

[0029]

【Example】

Example 1 Synthesis of 4-chloro-4,4-difluoro-2-ethoxymethylene-3-oxobutanoic acid ethyl ester

[0030]

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140 g of acetic anhydride, ethyl-4-chloro-
4,4-difluoro-3-oxobutanoic acid 9
A mixed solution of 8.2 g, 102 g of orthoformic acid ethyl ester and 10 mg of zinc chloride (ZnCl ₂ ) was refluxed for 6.5 hours. Further, the mixture was refluxed for 9 hours while attaching a Gene Stark apparatus while distilling off the solvent. After evaporating the solvent under reduced pressure, the residue was distilled under reduced pressure to obtain 119.6 g of the desired product as a pale yellow transparent liquid.

Boiling point 100-113 ° C / 0.7-0.8T
Example 2 Synthesis of 4-chlorodifluoromethyl-5-pyrimidinecarboxylic acid methyl ester

[0033]

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A mixture of 29 g of sodium methoxide, 48 g of formamidine acetate and 500 ml of anhydrous methanol was cooled on ice, and 99 g of 4-chloro-4,4-difluoro-2-ethoxymethylene-3-oxobutanoic acid ethyl ester was added. It was added dropwise over 30 minutes. After heating at 50 ° C. for 1 hour, the solvent was distilled off under reduced pressure, and 300 ml of water was added. After extraction with ethyl acetate and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was distilled under reduced pressure to give 63.7.
g of the desired product was obtained as a transparent liquid.

Boiling point 76-79 ° C./0.6 Torr ¹ H-NMR δ (ppm) [solvent]; 4.03 (s, 3H), 9.21 (s, 1H),
9.49 (s, 1H) [CDCl ₃ ] Example 3 Synthesis of 4-chlorodifluoromethyl-5-pyrimidinecarboxylic acid

[0036]

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5 g of methyl 4-chlorodifluoromethyl-5-pyrimidinecarboxylate, potassium hydroxide 2
g, 10 ml of water is stirred at room temperature overnight, and a further 50
Heated at 0 ° C. for 1 hour. While cooling with water, add concentrated hydrochloric acid to pH 1-2.
And the resulting solid was filtered off. 60 solids
Drying under reduced pressure at ° C. yielded 3.8 g of the desired product as a pale yellow solid.

Mp 155-158 ° C. Example 4 Synthesis of N-phenyl-4-chlorodifluoromethyl-5-pyrimidinecarboxamide

[0039]

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A) 15 g of 4-chlorodifluoromethyl-5-pyrimidinecarboxylic acid and 40 ml of thionyl chloride were suspended in 100 ml of chloroform and heated under reflux for 8 hours. The reaction mixture was filtered through a glass filter and then evaporated to obtain 10.8 g of 4-chlorodifluoromethyl-5-pyrimidinecarboxylic acid chloride as a liquid. b) 1 g of 4-chlorodifluoromethyl-5-pyrimidinecarboxylic acid chloride, 0.5 ml of aniline, 5 ml of triethylamine and 1 g of 4-dimethylaminopyridine were dissolved in 30 ml of tetrahydrofuran previously dried with molecular sieves 4A, and the mixture was stirred at room temperature for 17 hours. The mixture was evaporated and water was added to the residue. The product was extracted with ethyl acetate. It was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The product was subjected to silica gel chromatography (chloroform: ethyl acetate = 1: 1 to 5:
Purified according to 1), 0.44 g of N-phenyl-4-
Chlorodifluoromethyl-5-pyrimidinecarboxamide was obtained as crystals.

Example 5 N- (1,1-dimethylethyl) -N'-phenyl-4
Synthesis of -chlorodifluoromethyl-5-pyrimidinecarboxamidine (Compound No. 1 of the present invention)

[0042]

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0.25 g of N-phenyl-4-chlorodifluoromethyl-5-pyrimidinecarboxamide and 0.2 g of phosphorus pentachloride were dissolved in 50 ml of toluene, and the mixture was refluxed for 18 hours. The reaction mixture was evaporated. The residue was dissolved in 30 ml of tetrahydrofuran previously dried with molecular sieves 4A, 1 ml of tert-butylamine was added, and the mixture was stirred at room temperature for 23 hours. The reaction mixture was evaporated and water was added to the residue. The product was extracted with ethyl acetate. It was dried over anhydrous magnesium sulfate, filtered and evaporated. The product was purified by silica gel chromatography (chloroform: ethyl acetate = 10: 1),
0.25 g of N- (1,1-dimethylethyl) -N'-
Phenyl-4-chlorodifluoromethyl-5-pyrimidinecarboxamidine was obtained as a liquid. Example 6 N- [4- (1-methylpropyl) phenyl] -4-chlorodifluoromethyl-5-pyrimidinecarbothioimidic acid-1,1-dimethylethyl (Compound No.
Synthesis of 3)

[0044]

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A) N- [4- (1-methylpropyl) phenyl] -4-chlorodifluoromethyl-5-pyrimidinecarboxamide (2.9 g), phosphorus pentachloride (2 g), toluene 100 previously dried with molecular sieves 4A
The ml mixture was stirred overnight at reflux temperature. The reaction mixture was evaporated, yielding 3.7 g of an oily residue. b) A mixture of 1.2 g of an oily residue, 0.4 ml of 2-methyl-2-propanethiol, 10 ml of triethylamine and 50 ml of tetrahydrofuran previously dried with molecular sieves 4A was stirred overnight at room temperature.
Further, sodium hydride (60% in oil) is added.
15 g was added and stirred overnight. The reaction mixture was evaporated, water was added to the residue and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (hexane: ethyl acetate = 4: 1) and 0.44 g of N- [4- (methylpropyl) phenyl] -4-chlorodifluoromethyl-5-pyrimidinecarbothioimidic acid-1 , 1-dimethylethyl as a liquid. Example 7 Synthesis of 1-methylethyl N- (4-fluorophenyl) -4-chlorodifluoromethyl-5-pyrimidinecarbimidate (Compound No. 26 of the present invention)

[0046]

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1.0 g of N- (4-fluorophenyl) -4-chlorodifluoromethyl-5-pyrimidinecarboxamide, 0.8 g of phosphorus pentachloride, 1,4-dioxane 1
and a mixture of 20 ml of toluene was heated under reflux for 2 hours,
The solvent was distilled off under reduced pressure. Residue is isopropyl alcohol 2
0 ml, and 0.5 g of 60% sodium hydride was added at room temperature. After reacting at room temperature for 3 hours, the solvent was distilled off under reduced pressure.
The residue is separated on a preparative thin plate (developing solvent: ethyl acetate / hexane =
Purification by 3/7) gave 0.35 g of the desired product. Example 8 N-isopropyl-N ′-(α, α-dimethyl-4-fluorobenzyl) -4-chlorodifluoromethyl-5
Pyrimidine carboxamidine (Compound No. 3 of the present invention)
Synthesis of 9)

[0048]

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A mixture of 0.7 g of N-isopropyl-4-chlorodifluoromethyl-5-pyrimidinecarboxamide, 0.7 g of phosphorus pentachloride, 2 ml of 1,4-dioxane and 20 ml of toluene was heated under reflux for 2 hours, and the solvent was distilled off under reduced pressure. I left. The residue was dissolved in 30 ml of tetrahydrofuran,
α, α-dimethyl-4-fluorobenzylamine 1.0
g and 4-dimethylaminopyridine (1.0 g) were added, and the mixture was stirred at room temperature for 6 days. The solvent was distilled off under reduced pressure, the residue was extracted with ethyl acetate, and purified with a silica gel preparative thin plate (developing solvent: ethyl acetate / hexane = 4/6) to obtain 0.23 g of the desired product.

The structural formulas and physical properties of the compounds of the present invention synthesized according to the above Examples are shown in Tables 1 and 2 including the above Examples.
Shown in

[0051]

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[0052]

[Table 1] Compound No. XYR────────────────────────────────────1ClNH-tert-Bu Phenyl 2ClNH -Bu 4-sec-Bu-Phenyl 3 Cl S-tert-Bu 4-sec-Bu-Phenyl 4 Cl SCH _2- (4-Cl-Phenyl) 4-F-Phenyl 5 Cl NHCH _2- (4-Cl- Phenyl) 4-MeO-Phenyl 6 Cl N (Me) ₂ Phenyl 7 Cl NH-tert-Bu 4-Cl-Phenyl 8 Cl NH (Me) ₂ 4-Cl-Phenyl 9 Cl NH-tert-Bu 3-Cl- Phenyl 10 Cl NH-tert-Bu 2-Cl-Phenyl 11 Cl NH-tert-Bu 4-NO ₂ -Phenyl 12 Cl NH-tert-Bu 2-MeO-Phenyl 13 Cl NHN (Me) ₂ 2-MeO-Phenyl 14 Cl NH-tert-Bu 4-F-Phenyl 15 Cl NH-tert-Bu 4-CF ₃ -Phenyl 16 Cl 1-imidazolyl 4-F-Phenyl 17 Cl NH-tert-Bu 2-CF ₃ -Phenyl 18 Cl NH-tert-Bu 2-F-Phenyl 19 Cl NH-tert-Bu 3-F-Phenyl 20 Cl NH-tert-Bu 2-iso-Pr-Phenyl 21 Cl NH-tert-Bu 4-iso-Pr-Phenyl 22 Cl NH-tert-Bu 4-CO ₂ Me-Phenyl ───────────────────── ───────────────

[0053]

[Table 2] Compound No. XYR────────────────────────────────────23Cl NH ₂ 4-F-Phenyl 24Cl NHCON (Me) ₂ 4-F-Phenyl 25 Cl NHCO-tert-Bu 4-F-Phenyl 26 Cl O-iso-Pr 4-F-Phenyl 27 Cl NH-tert-Bu CH (Me)-(4-Cl -Phenyl) 28 Cl NH-tert-Bu 4,6-dimethoxy pyrimidine-2-yl 29 Cl NHCON (Me) ₂ 2-F-Phenyl 30 Cl NHCONH-tert-Bu 4-F-Phenyl 31 Cl NHC (Me) ₂ CH ₂ -Phenyl 2,4-Cl ₂ -Phenyl 32 Cl NH-tert-Bu 2,4-Cl ₂ -Phenyl 33 Cl NH-tert-Bu 3,5-Cl ₂ -Phenyl 34 Cl NHO-iso-Pr 4-F-Phenyl 35 Cl NHCON (Me) ₂ 2-iso-Pr-Phenyl 36 Cl 1-imidazolyl iso-Pr 37 Cl OCH ₂ C (Me) ₃ 4-F-Phenyl 38 Cl morpholino 4-F-Phenyl 39 Cl NHC (Me) _2- (4-F-Phenyl) iso-Pr 40 Cl phthalimido iso-Pr 41 Cl OCH ₂ CF ₃ 4-F-Phenyl 42 Cl OCH ₂ CH ₂ OCH ₂ CH ₃ 4-F-Phenyl 43 _{Cl CH (CO 2 Me) 2} iso-Pr 44 Cl O- (4-F-Phenyl) iso-Pr ─ ──────────────────────────────────

[0054]

[Table 3] Compound No. XYR ──────────────────────────────────── 45 Cl OMe 4-F-Phenyl 46 Cl OEt 4-F-Phenyl 47 Cl OCH ₂ CH ₂ N (Me) ₂ 4-F-Phenyl 48 Cl O-iso-Pr 4-Me-Phenyl 49 Cl O-CH (Et) ₂ 4-Me-Phenyl 50 Cl O -CH ₂ CH = C (Me) ₂ 4-Me-Phenyl 51 Cl O-CH (CH ₂ Cl) ₂ 4-F-Phenyl 52 Cl OCH ₂ CH ₂ OMe 4-F-Phenyl 53 Cl 3- (3- fluoropropyl) 4-F-Phenyl thiazoline-2-imino 54 Cl S-iso-Pr 4-F-Phenyl 55 Cl OCH (Et) ₂ 4-F-Phenyl 56 Cl OCH (Me) CH (Me) ₂ 4-F -Phenyl 57 Cl O-Phenyl 4-F-Phenyl 58 Cl O-CH ₂ C (Me) = CH ₂ 4-F-Phenyl 59 Cl NH- (4-F-Phenyl) 4-F-Phenyl 60 Cl OCH ₂ CH ₂ OEt 2,4-Cl ₂ -Phenyl 61 Cl OCH ₂ CH ₂ OMe 2,4-Cl ₂ -Phenyl 62 Cl OCH ₂ CH ₂ N (Me) ₂ 2,4-Cl ₂ -Phenyl 63 Cl NHOCH ₂ CO ₂ Me 4-F-Phenyl 64 Cl OCH (Me) -cyclo-Pr 4-F-Phenyl 65 Cl OCH (Me) CH ₂ OMe 4-F-Phenyl 66 Cl OCH (Me) Et 4-F-Phenyl ────────────────────────────────────

[0055]

[Table 4] Compound No. XYR ６７ 67 Cl OCH ₂ CH = C (Me) ₂ 4-F-Phenyl 68 Cl OPr 4-F-Phenyl 69 Cl OBu 4-F-Phenyl 70 Cl OCH (Et) ₂ 2,4-Cl ₂ -Phenyl 71 Cl O-iso-Pr CH ₂ CH _2- (3 -Cl-Phenyl) 72 Cl OCH ₂ CH ₂ OMe 2-F-Phenyl 73 Cl OCH ₂ CH ₂ OEt 2-F-Phenyl 74 Cl OCH ₂ CH ₂ OMe 3-F-Phenyl 75 Cl OCH ₂ CH ₂ OEt 3- F-Phenyl 76 Cl O (CH ₂ ) ₄ Me 4-F-Phenyl 77 Cl O (CH ₂ ) ₅ Me 4-F-Phenyl 78 Cl OPr CH ₂ CH _2- (3-Cl-Phenyl) 79 Cl OCH ₂ CH ₂ OEt CH ₂ CH _2- (3-Cl-Phenyl) 80 Cl OCH (Et) ₂ CH ₂ CH _2- (3-Cl-Phenyl) 81 Cl OCH ₂ CH ₂ OMe CH ₂ CH _2- (3-Cl -Phenyl) 82 Cl NH-iso-Pr CH ₂ CH _2- (3-Cl-Phenyl) 83 Cl S- (4-Me-Phenyl) CH ₂ CH _2- (3-Cl-Phenyl) 84 Cl OCH ₂ CH ₂ OPr 4-F-Phenyl 85 Cl OCH ₂ CH ₂ -O-iso-Pr 4-F-Phenyl 86 Cl OCH ₂ CH ₂ OBu 4-F-Phenyl 87 Cl OCH ₂ CH ₂ O-iso-Bu 4-F-Phenyl 88 Cl OCH ₂ CH ₂ OEt 4-Cl-2-CF ₃ -Phenyl 89 Cl O-iso-Pr Phenyl ────────────── ──────────────────────

[0056]

[Table 5] Compound No. XYR ９０ 90 Cl O-Pr Phenyl 91 Cl OCH ₂ CH ₂ Si (Me) ₃ 4-F-Phenyl 92 Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OMe 4-F-Phenyl 93 Cl OCH ₂ CH ₂ O-Phenyl 4-F-Phenyl 94 Cl O-iso-Pr CH ₂ CH ₂ O- (2,4-Cl ₂ Phenyl) 95 Cl O-iso-Pr 4-Cl-Phenyl 96 Cl OCH ₂ CH ₂ OMe 4-Cl-Phenyl 97 Cl OCH ₂ CH ₂ OEt 4-Cl-Phenyl 98 Cl Q ¹ 4-F-Phenyl 99 Cl OCH ₂ CH ₂ OEt Phenyl 100 Cl O-Pr CH _2- (3-Cl-Phenyl) 101 Cl OCH ₂ CH ₂ OEt CH _2- (3-Cl-Phenyl) 102 Cl O-iso-Pr CH ₂ CH ₂ -Phenyl 103 Cl OCH ₂ CH ₂ OMe CH ₂ CH ₂ -Phenyl 104 Cl OCH ₂ CH ₂ OEt CH ₂ CH ₂ -Phenyl 105 Cl OCOCH ₃ CH ₂ -Phenyl 106 Cl OCH ₂ CH ₂ CH ₂ OEt 4-F-Phenyl 107 Cl OCH ₂ CH ₂ CH ₂ CH ₂ OMe 4-F-Phenyl 108 Cl OCH ₂ CH ₂ OCH ₂ CH = CH ₂ 4-F-Phenyl 109 Cl OCH ₂ CH ₂ OCH ₂ CH ₂ Cl 4-F -Phenyl 110 Cl Q ² 4-F-Phenyl 111 Cl O-iso-Pr CH ₂ CH _2- (4-Cl-Phenyl) 112 Cl O-Pr CH ₂ CH _2- (4-Cl-Phenyl) ─── ─────────────────────────────────

[0057]

[Table 6] Compound No. XYR １１３ 113 Cl OCH ₂ CH ₂ OEt CH ₂ CH ₂ -(4-Cl-Phenyl) 114 Cl NH-Pr CH ₂ CH _2- (4-Cl-Phenyl) 115 Cl O-iso-Pr 3-Cl-Phenyl 116 Cl OCH ₂ CH ₂ OCH = CH ₂ 4-F _{-Phenyl 117 Cl OCH (CH 2 OEt} ) 2 4-F-Phenyl 118 Cl OCOCH 3 4-F-Phenyl 119 Cl Q 3 4-F-Phenyl 120 Cl Q 4 4-F-Phenyl 121 Cl OCH 2 CH (Me ) O-Phenyl 4-F-Phenyl 122 Cl OCH ₂ CH ₂ O- (4-Cl-Phenyl) 4-F-Phenyl 123 Cl OCH ₂ CH ₂ OEt 3-Cl-Phenyl 124 Cl O-iso-Pr 2- Cl-Phenyl 125 Cl OCH ₂ CH ₂ OEt 2-Cl-Phenyl 126 Cl OCH ₂ CH ₂ OMe 2-Cl-Phenyl 127 Cl S- (4-Me-Phenyl) 2-Cl-Phenyl 128 Cl NH-tert-Bu 2-Cl-Phenyl 129 Cl OCH (Me) CH ₂ O-Bu 4-F-Phenyl 130 Cl OCH (Me) CH ₂ O-tert-Bu 4-F-Phenyl 131 Cl OCH (Me) CH ₂ O-Phenyl 4-F-Phenyl 132 Cl OCH (Et) CH ₂ OMe 4-F- _{Phenyl 133 Cl OCH 2 CH 2 O-} (2-Cl-Phenyl) 4-F-Phenyl 134 Cl Q 5 4-F-Phenyl 135 Cl OCH 2 CH 2 SMe 4-F-Phenyl ──────── ────────────────────────────

[0058]

[Table 7] Compound No. XYR ──────────────────────────────────── 136 Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OCH ₂ CH ₂ Cl 4-F-Phenyl 137 F O-iso-Pr 4-F-Phenyl 138 Cl S-Et CH ₂ CH _2- (4-Cl-Phenyl) 139 Cl S- (4-Me-Phenyl) 3 -Cl-Phenyl 140 Cl S-Pr 4-F-Phenyl 141 Cl NHOCH 2 -Phenyl 4-F-Phenyl 142 Cl Q 6 4-F-Phenyl 143 Cl OCH 2 CH 2 CH 2 Cl 4-F-Phenyl 144 Cl O-iso-Pr 4-Pyridyl 145 Cl OCH ₂ C≡CH 4-F-Phenyl 146 Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OEt 4-F-Phenyl 147 Cl OCH ₂ CH ₂ OMe 4-Pyridyl 148 Cl OCH ₂ CH ₂ OEt 4-pyridyl ──────────────────────────────────── Incidentally, Q from Table in Q ^{1 6} represents the following substituents.

[0059]

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[0060]

[Table 2] Compound No. Physical properties ──────────────────────────────────── 1 n _D ^20.1 1.4656 2 n _D ^29.9 1.3973 3 n _D ^29.9 1.3539 4 n _D ^30.0 1.4096 5 mp 125-127 ° C 6 n _D ^20.6 1.5688 7 n _D ^20.7 1.5516 8 n _D ^20.7 1.5731 9 n _D ^20.0 1.5460 10 n _D ^20.0 1.5457 11 n _D ^20.0 1.5757 12 n _D ^20.0 1.5371 13 n _D ^20.0 1.5580 14 n _D ^20.4 1.5222 15 n _D ^20.4 1.5101 16 mp 122-124 ° C 17 n _D ^20.0 1.5172 18 n _D ^20.2 1.5351 19 n _D ^20.3 1.5298 20 mp 120-122 ° C 21 n _D ^20.3 1.5350 ─── ─────────────────────────────────

[0061]

[Table 9] 化合物 Compound No. Physical properties ２２ 22 n _D ^20.3 1.5459 23 mp 180-185 ℃ ^{_{24 mp 175-178 ℃ 25 n D 20.3}} 1.5298 26 mp 81-83 ℃ 27 n D 20.5 1.5291 28 mp 130-132 ℃ 29 mp 108-110 ℃ 30 mp 176-179 ℃ 31 n D 20.1 1.5763 32 n D 20.1 1.5545 33 n _D ^20.1 1.5541 34 n _D ^20.1 1.5409 35 mp 170-173 ° C 36 n _D ^20.3 1.5247 37 n _D ^20.3 1.5079 38 n _D ^20.3 1.5594 39 n _D ^20.5 1.5122 40 mp 115-117 ° C. 41 n _D ^20.4 1.4950 42 n _D ^20.4 1.5181 43 mp 86-88 ℃ 44 n _D ^21.0 1.5129 ────────────────────────────────────

[0062]

[Table 10] Compound No. Physical properties ──────────────────────────────────── 45 n _D ^19.8 1.5322 46 mp 43-45 ° C 47 n _D ^19.9 1.5239 48 n _D ^20.4 1.5300 49 n _D ^20.5 1.5244 50 n _D ^20.5 1.5362 51 n _D ^20.3 1.5356 52 n _D ^21.2 1.5240 53 n _D ^20.5 1.5950 54 mp 58-61 ° C 55 n _D ^20.7 1.5159 56 n _D ^21.0 1.5155 57 n _D ^20.8 1.5055 58 n _D ^20.8 1.5307 59 n _D ^21.1 1.4125 60 mp 95-97 ° C 61 n _D ^20.8 1.5546 62 n _D ^20.8 1.5509 63 mp 145-147 ° C. 64 mp 108-110 ° C. 65 n _D ^20.8 1.5177 66 n _D ^20.9 1.5168 67 n _D ^20.8 1.5238 ────────────────────────────────────

[0063]

[Table 11] Compound No. Physical properties ^{_{──────────────────────────────────── 68 n D 21.0 1.5225 69 n}} D 21.0 1.5185 70 n _D ^20.9 1.5419 71 n _D ^20.7 1.3636 72 n _D ^20.5 1.5271 73 n _D ^20.5 1.5210 74 n _D ^20.7 1.5254 75 n _D ^20.7 1.5195 76 n _D ^20.7 1.5156 77 n _D ^20.7 1.5130 78 n _D ^20.7 1.4524 79 n _D ^20.7 1.4404 80 n _D ^20.7 1.4149 81 n _D ^20.7 1.4461 82 n _D ^20.7 1.4708 83 n _D ^20.8 1.4446 84 mp 68-70 ° C 85 mp 84-86 ° C. 86 n _D ^20.4 1.5118 87 n _D ^20.5 1.5094 88 n _D ^20.7 1.4844 89 n _D ^20.7 1.4687 90 n _D ^20.7 1.5333 ────────────────────────────────────

[0064]

[Table 12] Compound No. Physical properties ──────────────────────────────────── 91 n _D ^20.7 1.5136 92 n _D ^20.7 1.5182 93 n _D ^20.7 1.5591 94 n _D ^20.5 1.5437 95 n _D ^20.5 1.5414 96 n _D ^20.5 1.5460 97 n _D ^20.6 1.5396 98 n _D ^20.7 1.5365 99 n _D ^20.5 1.4728 100 n _D ^20.5 1.4266 101 n _D ^20.5 1.4336 102 102 n _D ^20.9 1.5160 103 n _D ^21.1 1.5212 104 n _D ^21.1 1.5165 105 n _D ^20.8 1.5485 106 n _D ^20.4 1.5158 107 n _D ^20.4 1.5173 108 mp 73-75 ° C 109 mp 87-89 ° C 110 n _D ^20.5 1.5199 111 n _D ^20.7 1.4552 112 n _D ^20.8 1.4862 113 n _D ^20.8 1.4643 ────────────────────────────────────

[0065]

[Table 13] Compound No. Physical properties １１４ 114 n _D ^20.8 1.4915 115 n _D ^20.9 1.4371 116 n _D ^20.9 1.5287 117 n _D ^20.8 1.5064 118 mp 144-146 ° C 119 mp 106-108 ° C 120 mp 90-92 ° C 121 n _D ^20.9 1.5500 122 n _D ^21.0 1.5624 123 n _D ^24.8 1.4728 124 n _D ^24.8 1.4526 125 n _D ^24.8 1.4522 126 n _D ^24.8 1.4238 127 mp 94-96 ° C 128 n _D ^24.8 1.4403 129 n _D ^24.5 1.5052 130 n _D ^24.5 1.5035 131 n _D ^24.5 1.5490 132 n _D ^24.6 1.5142 133 mp 94-96 ° C 134 n _D ^24.7 1.5292 135 n _D ^24.6 1.5477 136 n _D ^24.6 1.5234 ────────────────────────────────────

[0066]

[Table 14] Compound No. Physical properties ^{_{──────────────────────────────────── 137 n D 24.6 1.4261 138 n}} D 24.5 1.4860 139 n _D ^24.5 1.4326 140 n _D ^24.6 1.5587 141 n _D ^25.0 1.5637 142 mp 162-163 ° C 143 n _D ^25.1 1.5327 144 mp 116-118 ° C. 145 n _D ^24.8 1.5386 146 n _D ^24.8 1.5142 147 n _D ^25.2 1.5330 148 n _D ^25.4 1.5274 本 The present invention synthesized according to the above scheme or example Table 3 shows the compounds including the compounds synthesized in the above Examples, but the present invention is not limited by these.

[Table 3]

[0068]

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[0069]

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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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[0078]

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[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087]

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[0088]

[Table 15] ──────────────────────────────────── Y ───────── ＮＨ NHMe, NHEt, NHPr, NHPr ^iso , NHBu, NHBu ^sec , NHBu ^tert , NHBu ^iso , NHCH ₂ CH ＣＨCH ₂ , NHCH ₂ C≡CH, NHCH (Me) CH ＝ CH ₂ , NHHex, NHCH (Me) C≡CH, NHC (Me) ₂ C≡CH, NHC (Me) ₂ CH ＝ CH ₂ , C≡ N, NH ₂ , N (Me) ₂ , N (Et) ₂ , N (Pr) ₂ , N (Pr ^iso ) ₂ , N (CH ₂ CH = CH ₂ ) ₂ , N (CH ₂ C≡CH) ₂ , NHPh, NH- (2-Cl-Ph), NH- (3-Cl-Ph), NH- (4-Cl-Ph), NH- (2-F-Ph), H- (3-F-Ph), NH- (4-F-Ph), NH- (2-Br-Ph), NH- (3-Br-Ph), NH- (4-Br-Ph), NH- (2-Me-Ph), NH- (3-Me-Ph), NH- (4-Me-Ph), NH- (2-MeO-Ph), NH- (3-MeO-Ph), NH- (4-MeO-Ph) , NH- (2-CF 3 -Ph), NH- (3-CF 3 -Ph), NH- (4-CF 3 -Ph), NH- (2-NO 2 -Ph), NH- (3-NO 2 -Ph), NH- (4-NO 2 -Ph), NH- (2-CF 3 O-Ph), NH- (3-CF 3 O-Ph), _{NH- (4-CF 3 O-} Ph), NH- (2,4-Cl 2 -Ph), NH- (3,4-Cl 2 -Ph), NH- (2,3-Cl 2 -Ph) , NH- (2,5-C l ₂ -Ph), NH- (2,6-Cl ₂ -Ph), NH- (3,5-Cl ₂ -Ph), NHCH ₂ Ph, NHCH _2- (2-Cl-Ph), ─── ─────────────────────────────────

[0089]

[Table 16] {Y} ＮＨ NHCH _2- (3-Cl-Ph), NHCH _2- (4-Cl-Ph), NHCH _2- (2-F-Ph), NHCH _2- (3-F-Ph), NHCH _2- (4-F-Ph), NHCH _2- (2-Br-Ph), NHCH _2- (3-Br _{-Ph), NHCH 2 - (4} -Br-Ph), NHCH 2 - (2-Me-Ph), NHCH 2 - (3-Me-Ph), NHCH 2 - (4-Me-Ph), NHCH 2 _{- (2-MeO-Ph)} , NHCH 2 - (3-MeO-Ph), NHCH 2 - (4-MeO-Ph), NHCH 2 - (2-CF 3 -Ph), NHCH 2 - (3-C _{3 -Ph), NHCH 2 - (} 4-CF 3 -Ph), NHCH 2 - (2-CF 3 O-Ph), NHCH 2 - (3-CF 3 O-Ph), NHCH 2 - (4-CF ₃ O-Ph), NHCH _2- (2-NO ₂ -Ph), NHCH _2- (3-NO ₂ -Ph), NHCH _2- (4-NO ₂ -Ph), NHCH _2- (2,4- _{Cl 2 -Ph), NHCH 2 -} (3,4-Cl 2 -Ph), NHCH 2 - (2,3-Cl 2 -Ph), NHCH 2 - (2,5-Cl 2 -Ph), NHCH 2 _{- (2,6-Cl 2 -Ph)} , NHCH 2 - (3,5-Cl 2 -Ph), NHCH 2 - (2-F-4-Cl-Ph), NHCH 2 - (3-F-4 -Cl-Ph), NHCH _2- (2,6-F ₂ -Ph), NHCH _2- (3,4-F ₂ -Ph), NHCH _2- (2,4 −F ₂ −Ph), ────────────────────────────────────

[0090]

[Table 17] {Y} ─────────────────────────── NHCH _2- (3-Me-4-F-Ph), NHCH _2- (3-Me- 4-Cl-Ph), NHOMe, NHOEt, NHOPr, NHOPr ^iso , NHOCH ₂ CH = CH ₂ , NHOCH ₂ C≡CH, NHOBu, NHOCH ₂ Ph, NHOCH _2- (4-Cl-Ph), NHOCH _2- ( 3-Cl-Ph), NHOCH 2 - (2-Cl-Ph), OMe, OEt, OPr, OPr iso, OBu, OBu sec, OBu tert, OBu iso, OCH 2 CH = CH 2, OCH 2 C≡CH , OCH (Me) CH = CH 2, OHex, OCH (Me) C≡CH, OC (M _{) 2 C≡CH, OC (Me)} 2 CH = CH 2, OPh, O- (2-Cl-Ph), O- (3-Cl-Ph), O- (4-Cl-Ph), O- (2-F-Ph), O- (3-F-Ph), O- (4-F-Ph), O- (2-Br-Ph), O- (3-Br-Ph), O- (4-Br-Ph), O- (2-Me-Ph), O- (3-Me-Ph), O- (4-Me-Ph), O- (2-MeO-Ph), O- (3-MeO-Ph), O- (4-MeO-Ph), O- (2-CF 3 -Ph), O- (3-CF 3 -Ph), O- (4-CF 3 -Ph) _{, O- (2-NO 2 -Ph} ), O- (3-NO 2 -Ph), O- (4-NO 2 -Ph), O- (2-CF 3 O-Ph), O- (3 _{-CF 3 O-Ph), O-} (4-CF 3 O-Ph), O- ( _{, 4-Cl 2 -Ph),} O- (3,4-Cl 2 -Ph), O- (2,3-Cl 2 -Ph), O- (2,5-Cl 2 -Ph), ── ──────────────────────────────────

[0091]

[Table 18] {Y} _{─────────────────────────── O- (2,6-Cl 2 -Ph} ), O- (3,5-Cl 2 - Ph), O- (2,6-F 2 -Ph), O- (2,4-F 2 -Ph), O- (3,4-F 2 -Ph), O- (2-F-4 _{-Cl-Ph), OCH 2 Ph} , OCH 2 - (2-Cl-Ph), OCH 2 - (3-Cl-Ph), OCH 2 - (4-Cl-Ph), OCH 2 - (2-F _{-Ph), OCH 2 - (3} -F-Ph), OCH 2 - (4-F-Ph), OCH 2 - (2-Br-Ph), OCH 2 - (3-Br-Ph), OCH 2 - (4-Br-Ph) , OCH 2 - (2-Me-Ph), OCH 2 - (3-M _{-Ph), OCH 2 - (4} -Me-Ph), OCH 2 - (2-MeO-Ph), OCH 2 - (3-MeO-Ph), OCH 2 - (4-MeO-Ph), OCH 2 _{- (2-CF 3 -Ph)} , OCH 2 - (3-CF 3 -Ph), OCH 2 - (4-CF 3 -Ph), OCH 2 - (2-CF 3 O-Ph), OCH 2 - _{(3-CF 3 O-Ph} ), OCH 2 - (4-CF 3 O-Ph), OCH 2 - (2-NO 2 -Ph), OCH 2 - (3-NO 2 -Ph), OCH 2 - _{(4-NO 2 -Ph),} OCH 2 - (2,4-Cl 2 -Ph), OCH 2 - (3,4-Cl 2 -Ph), OCH 2 - (2,3-Cl 2 -Ph) _{, OCH 2 - (2,5-Cl} 2 -Ph), OCH 2 - (2,6-Cl 2 -Ph), OCH 2 - (3,5-Cl 2 -Ph), OCH 2 - 2-F-4-Cl- Ph), OCH 2 - (3-F-4-Cl-Ph), ──────────────────────── ────────────

[0092]

[Table 19] Ｙ Y ───────── ─────────────────────────── OCH _2- (2,6-F ₂ -Ph), OCH _2- (3,4-F _{2 -Ph), OCH 2 - (} 2,4-F 2 -Ph), OCH 2 - (3Me-4-F-Ph), OCH 2 - (3Me-4-Cl-Ph), SMe, SEt , SPr, SPr ^iso , SBu, SBu ^sec , SBu ^tert , SBu ^iso , SCH ₂ CH = CH ₂ , SCH ₂ C≡CH, SCH (Me) CH = CH ₂ , SHex, SCH (Me) C≡CH, SC (Me) ₂ C≡CH, SC (Me) ₂ CH = CH ₂ , SPh, S- (2-Cl-Ph), S- (3-Cl-Ph), S- (4-Cl-Ph), S- (2- -Ph), S- (3-F-Ph), S- (4-F-Ph), S- (2-Br-Ph), S- (3-Br-Ph), S- (4-Br) -Ph), S- (2-Me-Ph), S- (3-Me-Ph), S- (4-Me-Ph), S- (2-MeO-Ph), S- (3-MeO -Ph), S- (4-MeO -Ph), S- (2-CF 3 -Ph), S- (3-CF 3 -Ph), S- (4-CF 3 -Ph), S- ( _{2-NO 2 -Ph), S-} (3-NO 2 -Ph), S- (4-NO 2 -Ph), S- (2-CF 3 O-Ph), S- (3-CF 3 O -Ph), S- (4-CF 3 O-Ph), S- (2,4-Cl 2 -Ph), S- (3,4-Cl 2 -Ph), S- (2,3-Cl _{2 -Ph), S- (2,5-} Cl 2 -Ph), ────────── ─────────────────────────

[0093]

[Table 20] {Y} _{─────────────────────────── S- (2,6-Cl 2 -Ph} ), S- (3,5-Cl 2 - Ph), S- (2,6-F 2 -Ph), S- (2,4-F 2 -Ph), S- (3,4-F 2 -Ph), S- (2-F-4 -Cl-Ph), SCH ₂ Ph, SCH _2- (2-Cl-Ph), SCH _2- (3-Cl-Ph), SCH _2- (4-Cl-Ph), SCH _2- (2-F -Ph), SCH _2- (3-F-Ph), SCH _2- (4-F-Ph), SCH _2- (2-Br-Ph), SCH _2- (3-Br-Ph), SCH ₂ - (4-Br-Ph) , SCH 2 - (2-Me-Ph), SCH 2 - (3-M _{-Ph), SCH 2 - (4} -Me-Ph), SCH 2 - (2-MeO-Ph), SCH 2 - (3-MeO-Ph), SCH 2 - (4-MeO-Ph), SCH 2 _{- (2-CF 3 -Ph)} , SCH 2 - (3-CF 3 -Ph), SCH 2 - (4-CF 3 -Ph), SCH 2 - (2-CF 3 O-Ph), SCH 2 - _{(3-CF 3 O-Ph} ), SCH 2 - (4-CF 3 O-Ph), SCH 2 - (2-NO 2 -Ph), SCH 2 - (3-NO 2 -Ph), SCH 2 - _{(4-NO 2 -Ph),} SCH 2 - (2,4-Cl 2 -Ph), SCH 2 - (3,4-Cl 2 -Ph), SCH 2 - (2,3-Cl 2 -Ph) _{, SCH 2 - (2,5-Cl} 2 -Ph), SCH 2 - (2,6-Cl 2 -Ph), SCH 2 - (3,5-Cl 2 -Ph), SCH 2 - 2-F-4-Cl- Ph), SCH 2 - (3-F-4-Cl-Ph), ──────────────────────── ────────────

[0094]

[Table 21] {Y} ＣＨ SCH _2- (2,6-F ₂ -Ph), SCH _2- (3,4-F _{2 -Ph), SCH 2 - (} 2,4-F 2 -Ph), SCH 2 - (3Me-4-F-Ph), SCH 2 - (3Me-4-Cl-Ph), NHCH 2 CH _{2 OMe, NHCH 2 CH 2 OEt} , NHCH 2 CH 2 CH 2 OMe, NHCH 2 CH 2 CH 2 OEt, NHCOMe, NHCOEt, NHCOPr iso, NHCOPr, NHCOBu, NHCOBu sec, NHCOBu iso, NHCOBu tert, NHCO 2 Me, NHCO ₂ Et, NHCO ₂ Pr, NHCO ₂ Pr ^iso , NHCO ₂ Bu, NHC ^{_{O 2 Bu sec, NHCO 2 Bu}} iso, NHCO 2 Bu tert, NHNH 2, NHNHMe, NHNHEt, NHNHPr, NHNHBu tert, NHN (Me) 2, NHN (Et) 2, NHN (Pr) 2, NHN (Pr iso) ₂ , NH ₂ , NHCON (Me) ₂ , NHCONHMe, NHCONHPr, ─────────────────────────────────── ─

[0095]

[Table 22] {Y} ＮＨ NHCON (Et) ₂ , NHCONHEt, NHCONHPr ^iso , NHCONHBu ^tert , NHCONHBu, NHCONHBu ^sec , NHCONHBu ^iso , NHCONH ₂ , NHSO ₂ NH ₂ , NHSO ₂ NHMe, NHSO ₂ NHEt, NHSO ₂ NHPr, NHSO ₂ NHPr ^iso , NHSO ₂ NHBu, NHSO ₂ NHBu ^tert , NHSO ₂ N (Me) ₂ , NHSO ₂ N (Et) ₂ NHSO _{2 N (Pr) 2, NHSO 2} N (Pr iso) 2, NHSO 2 N (Bu) 2, NHC (Me) 2 - (4-Cl-Phenyl), NHC (Me) 2 - (4-F-P _{enyl), NHC (Me) 2} CH 2 -Phenyl, NHCH (Me) - (4-Cl-Phenyl), NHCH (Me) -Phenyl, 1-imidazolyl, pyrazole-1-yl, morpholino, triazole-1-yl , Phtalimido, CH (CO ₂ Me) ₂ , CH (CO ₂ Et) ₂ , CH (CN) ₂ , OCH ₂ C (Me) ₃ , OC (Me) ₂ Et, OCH (Me) CH ₂ CH ₂ CH ₃ , OCH (Et) ₂ , ────────────────────────────────────

[0096]

[Table 23] ──────────────────────────────────── Y ───────── ^{─────────────────────────── OCH (Me) -Pr cyclo,} OPr cyclo, OHex cyclo, OPen cyclo, OCH 2 CH 2 OMe, _{OCH 2 CH 2 OEt, OCH 2} OMe, OCH 2 OEt, OCH 2 CH 2 N (Me) 2, OCH (Me) CH 2 OCH 3, OCH (Me) CH 2 OEt, OCH 2 C (Me) = CH 2 _{, OCH 2 CH = C (Me} ) 2, OCH (Et) CH 2 Cl, OCH (CH 2 Cl) 2, OCH 2 CF 3, NHOCH 2 CO 2 Me, NHOCH 2 CO 2 Et, 3- (3-fluoropropyl) _{thiazoline-2-imino, OPn, OCH 2 CH 2 OPr} , OCH 2 CH 2 OPr iso, OCH 2 CH 2 OBu, OCH 2 CH 2 OBu iso, OCH 2 CH 2 OPr cyclo, OCH _{^{2 CH 2 OPn cyclo, OCH 2}} CH 2 Si (Me) 3 OCH 2 CH 2 OCH 2 CH 2 OMe, OCH 2 CH 2 OCH 2 CH 2 OEt, OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 Cl, OCH ₂ CH ₂ OCH ₂ CH ₂ OPr, ────────────────────────────────────

[0097]

[Table 24] {Y} ─────────────────────────── OCH ₂ CH ₂ OPh, OCH ₂ CH ₂ O- (3-F-Ph), OCH ₂ CH _{2 O- (4-Cl-Ph} ), OCH 2 CH 2 O- (2-Cl-Ph), OCH 2 CH 2 O- (3-Cl-Ph), OCH 2 CH 2 O- (4-F- _{Ph), OCH 2 CH 2 O-} (2-F-Ph), OCH 2 CH (Me) O- (2-Cl-Ph), OCH 2 CH (Me) O- (3-Cl-Ph), OCH _{2 CH (Me) O- (4} -Cl-Ph), OCH 2 CH (Me) OPh, OCH 2 CH (Me) OMe, OCH 2 CH (Me) OEt, OCH 2 CH (Me) OPr, OCH 2 CH Me) OPn, OCH (Me) CH 2 OPh, OCH (Me) CH 2 OBu, OCH (Me) CH 2 OBu tert, OCH (Me) CH 2 OMe, OCH (Me) CH 2 OEt, OCH (Me) CH ₂ OPr, OCH (Me) CH ₂ OPn, OCH ₂ CH ₂ CH ₂ OMe, OCH ₂ CH ₂ CH ₂ OEt, OCH ₂ CH ₂ CH ₂ OPro ^iso , OCH ₂ CH ₂ CH ₂ OPr, OCH ₂ CH ₂ CH ₂ OBu, OCH ₂ CH ₂ CH ₂ CH ₂ OMe, OCH ₂ CH ₂ CH ₂ CH ₂ OEt, OCH ₂ CH ₂ CH ₂ CH ₂ OPr ^iso , OCH ₂ CH ₂ CH ₂ CH ₂ OPr, OCH ₂ CH ₂ CH _{2 2} OBu, OCH ₂ CH ₂ CH ₂ CH ₂ CH ₂ OMe, OCH ₂ CH ₂ CH ₂ CH ₂ CH ₂ OEt, ─────────────────────── ─────────────

[0098]

[Table 25] {Y} ───────────────────────────OCH ₂ CH ₂ OCH ₂ CH ＝ CH ₂ , OCH ₂ CH ₂ OCH ₂ C≡CH, OCH ₂ CH ₂ OCH (Me) CH = CH ₂ , OCH ₂ CH ₂ OC (Me) ₂ CH = CH ₂ , OCH ₂ CH ₂ OCH ₂ CH ₂ Cl, OCH ₂ CH ₂ OCH = CH ₂ , OCH (CH ₂ OMe) _{2, OCH (CH 2 OEt)} 2, OCH (Me) CH 2 O- (2-Cl-Ph), OCH (Me) CH 2 O- (3-Cl-Ph), OCH (Me) CH 2 O- (4-Cl-Ph), OCH (Et) CH 2 OMe, OCH (Et) CH 2 OEt, OCH 2 CH 2 SMe, OCH 2 CH 2 SEt, _{CH 2 CH 2 SPr, OCH 2} CH 2 SPr iso, OCH 2 CH 2 CH 2 Cl, OCH 2 CH 2 Cl, OCH 2 CH 2 CH 2 CH 2 Cl, OCH 2 CH 2 CHCl 2, OCOMe, OCOEt, OCOPr, ^{OCOPr iso, OCOBu, OCOBu sec,} OCOBu iso, OCOBu tert, OCOPn, OCOPn cyclo, OCOPr cyclo, OCOHex, Q 1, Q 2, Q 3, Q 4, Q 5 or Q 6 ─────────記号 The symbols in the table have the following meanings.

Ph: Phenyl Me: CH ₃ Et: C ₂ H ₅ Pr, Pr ⁿ : CH ₂ CH ₂ CH ₃ Pr ^iso : CH (CH ₃ ) ₂ Pr ^cyclo : CH (CH ₂ ) ₂ Bu, Bu ⁿ : _{CH 2 CH 2 CH 2 CH 3} Bu sec: CH (CH 3) C 2 H 5 Bu iso: CH 2 CH (CH 3) 2 Bu tert: C (CH 3) 3 Bu cyclo: CH (CH 2) 3 Pn ^{_{, Pn n: CH 2 CH 2}} CH 2 CH 2 CH 3 Pn cyclo: CH (CH 2) 4 Pn iso: CH 2 CH 2 CH (CH 3) 2 Pn neo: CH 2 C (CH 3) 3 Hex, Hex ^{_{n: CH 2 (CH 2)}} 4 CH 3 Hep, Hep n: CH 2 (CH 2) 5 CH 3 Oct, Oct n: CH 2 (CH 2) 6 CH 3 4-Cl-Ph: 4-Cl-Phenyl In the table, Q ¹ to Q ⁶ represent the following substituents.

[0100]

Embedded image

In applying the compound of the present invention as a herbicide and a plant growth regulator, a suitable carrier is generally used, such as a solid carrier such as clay, talc, bentonite, urea, ammonium sulfate, walnut powder, diatomaceous earth, white carbon, or water. , Alcohols (isopropanol, butanol, ethylene glycol, benzyl alcohol,
Furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, methylnaphthalene, etc.), ethers (anisole, etc.), vegetable oils (soybean oil, cottonseed oil, etc.), ketones (cyclohexanone, isophorone, etc.), esters (acetic acid) Butyl, etc.), acid amides (N-methylpyrrolidone, etc.)
Or, it can be applied by mixing with a liquid carrier such as halogenated hydrocarbons (chlorobenzene and the like), and if desired, a surfactant, an emulsifier, a dispersant, a penetrant, a spreading agent, a thickener, a deicing agent. And an anti-caking agent, a stabilizer and the like, and can be put to practical use in any dosage form such as a liquid, an emulsion, a wettable powder, a dry flowable, a flowable, a powder and a granule.

The compound of the present invention may be added to other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, when necessary, in the preparation or spraying. You may mix and apply with a soil improving agent etc. In particular, by mixing and applying other pesticides, the cost can be reduced by reducing the amount of applied medicine, the spectrum can be expanded by the synergistic action of the mixed medicine,
A higher herbicidal effect or a plant growth regulating effect can be expected. At this time, a combination with a plurality of known agricultural chemicals is possible at the same time. Examples of the kind of agrochemical used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm Chemicals Handbook)
And the compounds described in the 1995 edition.

The amount of the compound of the present invention to be applied varies depending on the application scene, application time, application method, weather condition, preparation form, soil condition, cultivated crops and the like, but generally the amount of the active ingredient is 0.1 to 0.1 ha / ha. About 0001-10kg,
Preferably about 0.001 to 5 kg is appropriate. However, when used for germination of plant seeds and promotion of initial growth, it is preferable to adjust and use the active ingredient concentration to be 0.01 to 100 ppb.

Next, specific examples of the formulation of the preparation when the compound of the present invention is used will be shown. However, the composition examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight. [Wettable powder] Compound of the present invention────────0.1-80 parts Solid carrier────────10-90 parts Surfactant────────1-10 Part Others # 1-5 Part Others include, for example, an anti-caking agent.

[Emulsion] Compound of the present invention (0.1 to 30 parts) Liquid carrier (30 to 95 parts) Surfactant (5) To 15 parts [Flowable agent] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 65 parts Surfactant 5 １２12 parts Others ────────5-30 parts Others include, for example, an antifreezing agent and a thickener.

[Granular wettable powder (dry flowable)] Compound of the present invention {0.1 to 90 parts Solid carrier {10 to 70 parts Surfactant} {1 to 20 parts [granule] Compound of the present invention} 0.0001 to 10 parts Solid carrier {90 to 99.99999 parts Others} ──────0.1 to 10 parts [Solution] Compound of the present invention ────────0.00001 to 30 parts Liquid carrier 部 0.1 to 50 parts Water {50-99.99 parts Others} 0-10 parts [Coating agent] Compound of the present invention {1-50 parts Liquid carrier} ──────30-95 parts Thickener ────────5-50 parts [Trunk injection agent] Compound of the present invention ────────0.01-30 parts Liquid carrier # 70 to 99.99 parts [Compounding Example 1] Water-dispersible compound of the present invention. 1 $ 50 part Sieglite PFP $ 43 part (Kaolin based clay: trade name of Geek Light Industry Co., Ltd.) Solpol 5050 $ 2 Part (anionic surfactant: Toho Chemical Industry Co., Ltd.) Lunox 1000C # 3 part (anionic surfactant: Toho Chemical Industry Co., Ltd.) Carplex # 80 ( Anti-caking agent) 2 parts (white carbon: trade name of Shionogi & Co., Ltd.) The above ingredients are uniformly mixed and pulverized into a wettable powder.

[Formulation Example 2] Emulsion Inventive compound No. 14───────3 parts Xylene ─────────76 parts Isophorone ─────────15 parts Solpol 3005X ────────6 parts (nonionic A mixture of a surfactant and an anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above are uniformly mixed to form an emulsion.

[Formulation Example 3] Flowable agent Compound No. 1 of the present invention. 26 ──────35 parts Agrisol S-711 ───────8 parts (Nonionic surfactant: trade name of Kao Corporation) Lunox 1000C ────────0.5 Part (anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) 1% rhodopol water ─────────20 parts (thickener: trade name of Lone Poulin Co.) Ethylene glycol (antifreeze ) ───8 parts water ─────────28.5 parts The above are mixed uniformly to form a flowable agent.

[Formulation Example 4] Granular wettable powder (dry flowable agent) 42 # 75 part Isoban No. 1 $ 10 parts (anionic surfactant: Kuraray Isoprene Chemical Co., Ltd.) Vanirex N $ 5 parts (anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd.) Carplex # 80 ────────10 parts (white carbon: Shionogi & Co., Ltd. Co., Ltd.) The above components are uniformly mixed and pulverized to prepare a dry flowable agent.

[Formulation Example 5] Granules Compound of the present invention No. 5 45 ──────0.1 parts Bentonite ─────────50.0 parts Talc ─────────44.9 parts Toxanone GR-31A ─────── 5 parts (anionic surfactant: Sanyo Kasei Kogyo Co., Ltd.) After uniformly mixing and pulverizing the above, adding a small amount of water, mixing and kneading, granulating with an extruder, and drying. Into granules.

[Formulation Example 6] Solution Compound of the present invention No. 5 26 {3 parts 1-methoxy-2-propanol} 20 parts Water {77 parts The above are mixed to form a uniform solution to form a liquid preparation.

[Formulation Example 7] Solution Compound of the present compound No. 5 1 {0.0001 part 1-methoxy-2-propanol} 1.0 part Water 98.9999 parts Mix the above to make a homogeneous solution and make a liquid. [Formulation Example 8] Coating agent Compound of the present invention No. 5 15 10 parts Thixogel VP 10 parts (Nissan Gardler Catalyst Co., Ltd. trade name) Xylene # 80 parts [Formulation Example 9] Coating agent Compound of the present invention 41 15 parts Thixogel VP 10 parts (Nissan Gardler Catalysts Co., Ltd. trade name) Hisol 100 No. 75 parts (Nisseki Chemicals trade name) [Formulation Example 10] Trunk injection agent Compound of the present invention 1 6 parts isopropanol 94 parts [Formulation Example 11] Trunk injection agent Compound of the present invention No. 1 26 5 parts ethanol 95 parts When using the above wettable powder, emulsion, flowable, The particulate wettable powder is diluted 50 to 1000 times with water and dispersed so that the active ingredient becomes 0.0001 to 10 kg per hectare (ha).

Next, the usefulness of the compound of the present invention as a herbicide, a plant growth regulator and a fungicide will be specifically described in the following test examples. [Test Example-1] Herbicidal effect test by weed generation pretreatment under flooded conditions After placing alluvial soil in a 1/10000 arel Wagner pot, water was added and mixed to obtain a flooded condition with a water depth of 4 cm. The above-mentioned pot is transplanted with rice at the 2 leaf stage, and the seeds of Nobie, Firefly, Konagi, Kikasigusa, Urikawa,
A tuber of Spodoptera mori was mixed and sowed. Pot at 25-30 ° C
The plants of the present invention were prepared according to the formulation examples so that the plants were grown in the greenhouse on the first day after the sowing, so that a predetermined dose was applied to the surface of the water. Three weeks after the treatment, the herbicidal effect on various weeds was visually inspected according to the following criteria. 0 is no effect and 5 is a 5-point scale showing complete withering. The results are shown in Table 3-1.

It should be noted that in each table, No. Is the compound No. described in the examples. And the symbols have the following meanings. A: nobie, B: firefly, C: corn, D: smelt, E: urikawa, F: moss, a: rice Criteria 5: Herbicidal rate 90% or more (almost completely withered) 4 ... Herbicidal rate 70-90% 3 ... weed kill rate 40-70% 2 ... weed kill rate 20-40% 1 ... weed kill rate 5-20% 0 ... weed kill rate 5% or less (almost no effect) Herbicidal effect test After placing alluvial soil in a Wagner pot of 1 / 10,000 ares, water is added and mixed, so that the water is immersed at a depth of 4 cm. Seeds of nobies, fireflies, pearls, and red stag beetles were mixed into the above pots. The pot was grown in a greenhouse at 25 to 30 ° C., and on the 14th day after sowing, the compound of the present invention prepared according to the formulation example was treated so as to have a predetermined dose on the water surface. Three weeks after the treatment, the herbicidal effect on various weeds and the effect on rice were visually examined according to the criteria of Test Example-1. 0 is no effect and 5 is a 5-point scale showing complete withering. The results are shown in Table 3-2.

It should be noted that in each table, No. Is the compound No. described in the examples. And the symbols have the following meanings. A: Nobie, B: Firefly, C: Konagi, D: Kikashigusa [Test Example-3] Herbicidal effect test by soil treatment Put sterilized flood soil in a plastic box having a length of 33 cm, a width of 33 cm and a depth of 8 cm. , Enokorogusa, oats, blackgrass, strawberries, fir,
The present invention prepared according to a blending example so as to have a predetermined dosage after mixing seeds of Aobuyu, Morning Glory, Ooinufufuguri, Hakobe, Rice, Maize, Wheat, Soybean, Cotton, Beet and covering about 1.5 cm, so as to have a predetermined dosage. The compound was evenly sprayed on the soil surface. Three weeks after the application of the chemical solution, the herbicidal effect on various weeds and the effect on crops were visually inspected in accordance with the criteria of Test Example-1. 0 is no effect and 5 is a 5-point scale showing complete withering. Third result
The results are shown in Table-3.

It should be noted that in each table, No. Is the compound No. described in the examples. And the symbols have the following meanings. G: Nobie, H: Enokorogosa, I: Oats, J:
Blackgrass, K: Ichibai, L: Onami-momi, M: Aoyama, N: Asagao, O: Oyanofuguri, P: Hakobe, a: Rice, b: Maize, c: Wheat, d: Soybean, e: Cotton, f: Beat [Test Example-4] Herbicidal effect test by foliage treatment Put sterilized flood soil in a plastic box having a length of 33 cm, a width of 33 cm, and a depth of 8 cm, and add nobie, enokorogosa, oat, blackgrass, ibis, onamimi,
Mixed seeds of Aobuyu, Morning Glory, Ooinufuguri, Chickweed, Rice, Maize, Wheat, Soybean, Cotton, Beetroot, cover about 1.5 cm, then grow the plants at room temperature of 25 to 30 ° C for 14 days, The compound of the present invention prepared according to the formulation example was uniformly applied to the foliage. Test Example 1 on herbicidal effects on various weeds and effects on crops 3 weeks after spraying the chemical solution
Was visually inspected according to the criteria of the above. 0 has no effect,
5 is a 5-grade evaluation indicating complete withering. Result 3-4
It is shown in the table.

It should be noted that in each table, No. Is the compound No. described in the examples. And the symbols have the following meanings. G: Nobie, H: Enokorogosa, I: Oats, J:
Blackgrass, K: Ichibai, L: Onami-momi, M: Aoyama, N: Asagao, O: Oyanofuguri, P: Hakobe, a: Rice, b: Maize, c: Wheat, d: Soybean, e: Cotton, f: Beat [Test Example-5] Test of dwarfing effect by foliage treatment Put sterilized flood soil in a plastic pot having an inner diameter of 12 cm and a depth of 11 cm, and sown rice, wheat, bermudagrass, and bentgrass seeds separately in each pot. The soil was covered by 1 cm. The pot is placed in a greenhouse at 25 to 30 ° C. to grow the plant, and when the various plants reach the 1-2 leaf stage, the compound of the present invention, which is adjusted according to the formulation examples, is used in a predetermined ratio of the amount of the active ingredient. Then, the entire foliage of various plants was evenly sprayed with a small spray. Two weeks after spraying the chemical, the dwarfing effect on various plants was investigated. The survey measured plant height and leaf age. Compound No. 1 showed a good dwarfing effect. [Test Example-6] Dwarfing effect test under flooding condition After placing alluvial soil in a plastic pot of 1 / 10,000 ares, water is added and mixed, and the condition of flooding at a depth of 4 cm is set. The rice of about 2 leaves grown in the nursery box is transplanted into a pot, and the pot is placed in a greenhouse at 25 to 30 ° C. to grow the rice. When the rice reaches the 3.5 leaves, The compound of the present invention prepared according to the formulation example was treated so as to have a predetermined ratio. Two weeks after the chemical treatment, the dwarfing effect on rice was investigated. The survey measured plant height and leaf age. Compound No. 1 showed a good dwarfing effect.

[0118]

[Table 26] Herbicidal effect test by weed pretreatment under flooded conditions ───────── Compound No. dose g / a ABCDEF a ─────────────────────────────── １ 1 10 5 4 5 5-3 3 2 2.52 3 0 5 5 0 0 0 3 2.52 2 0 5 5 0-0 4 2.52 5 2 5 5 0 0 0 5 2.52 0 2 4 5-0 0 6 2.52 3 0 2 2-0 0 7 2.52 5 5 5 5-0 0 8 2.52 5 5 5 5-0 0 9 2.52 5 5 5 5-0 0 10 2.52 5 5 5 5-0 0 11 2.52 3 0 0 3-0 0 12 2.52 0 0 0 5-0 0 13 2.52 2 0 0 2-0 0 14 2.52 5 5 5 5-0 0 15 2.52 5 5 5 5-0 0 16 2.52 4 4 5 5-2 0 17 2.52 5 5 5 5-0 0 18 2.52 5 5 5 5-2 0 19 2.52 5 5 5 5-2 0 20 2.52 0 0 2 3-0 0 21 2.52 5 3 5 5-2 0 22 2.52 5 3 5 5 -2 0 ────────────────────────────── ─────

[0119]

[Table 27] 化合物 Compound No. Dose g / a ABCDEF a ２３ 23 2.52 2 0 3 2-0 0 24 2.52 0 0 2 0-0 0 25 2.52 2 0 2 2-0 0 26 2.52 5 5 5 5-0 0 27 2.52 0 0 2 4-0 0 28 2.52 0 0 3 3-0 0 29 2.52 3 2 2 4-0 0 30 2.52 2 2 0 3-0 0 31 2.52 4 3 5 5-0 0 32 2.52 5 5 5 5-0 0 33 2.52 5 4 5 5-0 0 34 2.52 4 3 5 5-0 0 35 2.52 0 0 2 4 -0 0 36 2.52 2 3 5 5-0 0 37 2.52 5 3 5 5-0 0 38 2.52 0 0 2 4-0 0 41 2.52 5 5 5 5-0 0 42 2.52 5 5 5 5-0 0 44 10 5 5 5 5-0 0 45 2.52 5 5 5 5 0 0 0 46 2.52 5 5 5 5 0 4 0 48 10 5 5 5 5 5 5 0 49 10 5 5 5 5 5 5 0 0 ─────── ─────────────────────────────

[0120]

[Table 28] 化合物 Compound No. Dose g / a ABCDEF a ５０ 50 2.52 2 0 0 0 0 0 0 51 10 4 0 4 5 0 0 0 52 10 5 5 5 5 5 5 0 53 10 2 0 0 0 0 0 0 54 2.52 5 5 5 5 0 0 0 55 2.52 5 4 5 5 0-0 56 2.52 5 1 5 5 4 0 0 57 2.52 5 5 5 5 0 1 0 58 2.52 5 5 5 5 0 0 0 59 2.52 2 0 0 0 0 0 0 60 2.52 5 5 5 5 4-0 61 2.52 5 5 5 5 0-0 62 2.52 2 0 0 0 0 0 0 63 2.52 0 0 1 0 0 0 0 65 2.52 5 5 5 5 3 5 0 66 2.52 5 5 5 5 3 5 0 68 2.52 5 5 5 5 0 0 0 69 2.52 5 5 5 5 3 0 0 70 2.52 5 0 5 5 0 0 0 71 2.52 5 5 5 5 0 0 0 72 2.52 5 5 5 5 2 0 0 73 2.52 5 5 5 5 2-0 74 2.52 5 5 5 5 0 0 0 ─────── ─────────────────────────────

[0121]

[Table 29] ──────────────────────────────────── Compound No. Drug dose g / a ABCDEF a ──────────────────────────────────── 75 2.52 5 5 5 5 0 2 0 76 2.52 4 3 5 5 0 0 0 77 2.52 5 2 5 5 0 5 0 79 2.52 5 5 5 5 0 0 0 80 2.52 5 2 5 5 0 0 0 81 2.52 5 5 5 5 5 0 0 83 2.52 5 1 5 5 4 0 0 84 2.52 5 4 5 5 0 0 0 85 2.52 5 5 5 5 0 0 0 86 2.52 5 4 5 5 5 0 0 87 2.52 5 3 5 5 0 0 0 88 2.52 5 5 5 5 0 0 0 89 2.52 5 4 5 5 0 0 0 90 2.52 4 5 5 5 0 0 0 92 2.52 5 5 5 5 4-0 93 2.52 5 5 5 5 2 0 0 94 2.52 5 1 5 5 5 0 0 95 2.52 5 5 5 5 0 0 0 96 2.52 5 5 5 5 5 0 0 97 2.52 5 5 5 5 3 0 0 98 2.52 5 5 5 5 0 3 0 99 2.52 5 5 5 5 0 1 0 100 2.52 5 4 5 5 0 5 0 ─────── ─────────────────────────────

[0122]

[Table 30] ──────────────────────────────────── Compound No. Dose g / a ABCDEF a １０１ 101 2.52 5 5 5 5 0 0 0 102 2.52 5 1 5 5 0 5 0 103 2.52 5 1 5 5 0 0 0 104 2.52 5 0 5 5 0 0 0 105 2.52 2 0 0 0 0 0 0 106 2.52 5 4 5 5 0 0 0 107 2.52 5 4 5 5 0 0 0 108 2.52 5 3 5 5 0 00 0 109 2.52 5 2 5 5 0 5 0 110 2.52 4 0 5 5 0 0 0 111 2.52 5 5 5 5 0 0 0 112 2.52 5 4 5 5 0 0 0 113 113 2.52 5 5 5 5 0 3 0 115 2.52 4 4 5 5 0 0 0 116 2.52 3 0 5 3 0 0 0 117 2.55 5 5 5 5 1 2 0 119 2.52 4 5 5 5 0 0 0 120 2.52 5 5 5 5 0 0 0 121 2.52 5 0 5 5 0 0 0 122 2.52 5 0 5 5 0 0 0 123 2.52 4 5 5 5 0 0 0 124 2.52 4 5 5 5 0 0 0 125 2.52 5 5 5 5 0 0 0 ─────── ───────────── ───────────────

[0123]

[Table 31] 化合物 Compound No. Dose g / a ABCDEF a ──────────────────────────────────── 126 2.52 5 5 5 5 5 0 0 127 2.52 5 5 5 5 0 0 0 128 2.52 5 5 5 5 3 0 0 129 2.52 5 0 5 5 0 0 0 130 2.52 5 3 5 5 0 0 0 131 2.52 5 1 5 5 0 0 0 132 2.52 5 1 5 5 0 0 0 133 2.52 5 1 5 5 0 0 0 134 2.52 5 3 5 5 0 0 0 135 2.52 4 3 5 5 0 0 0 136 2.52 4 3 5 5 0 0 0 137 2.52 1 0 0 2 0 0 0 138 2.52 5 5 5 5 0-0 139 2.52 5 0 5 5 0 0 0 140 2.52 5 5 5 5 0 0 0 143 2.52 0 2 5 4 00 0 144 144 2.52 5 3 5 5 0 0 0 145 2.52 5 4 5 5 0 2 0 146 2.52 5 4 5 5 4 2 0 147 2.52 4 4 5 5 0 0 0 148 2.52 4 3 5 5 0-0 ───────────────────────── ───────────

[0124]

[Table 32] [Table 3-2] Test of herbicidal effect by post-weed treatment under flooded conditions化合物 Compound No. Drug dose g / a ABCD １ 1 10 5 3 5 5 2 2.52 0 0 0 5 3 2.52 0 0 0 5 4 2.52 0 2 2 5 5 2.52 2 2 5 5 6 2.52 0 2 3 0 7 2.52 5 3 5 5 8 2.52 3 3 5 4 9 2.52 5 5 5 5 10 2.52 5 5 5 5 12 2.52 0 0 2 0 13 2.52 0 0 0 2 14 2.52 4 3 5 5 15 2.52 5 3 5 4 16 2.52 2 2 5 5 17 2.52 4 3 5 5 18 2.52 5 3 5 5 19 2.52 5 3 5 5 20 2.52 0 0 0 4 21 2.52 5 3 5 5 22 2.52 5 3 5 5 23 2.52 3 0 5-────────────────────────── ────

[0125]

[Table 33] 化合物 Compound No. Dose g / a ABCD ─────── ─────────────────────── 24 2.52 0 2 4 4 25 2.52 3 3 5 5 26 2.52 5 5 5 5 27 2.52 0 0 0 3 28 2.52 2 0 0 0 29 2.52 2 2 2 2 30 2.52 3 2 3-31 2.52 0 0 0 5 32 2.52 5 3 5 5 33 2.52 2 3 5 5 34 2.52 2 3 5-36 2.52 2 2 2 3 37 2.52 2 2 5 5 38 2.52 0 0 2 2 41 2.52 3 3 5 5 42 2.52 5 3 5 5 44 10 5 4 5 5 45 2.52 0 4 5 5 46 2.52 3 3 5 5 48 10 4 5 5 5 49 10 4 4 5 5 50 10 4 4 5 5 51 10 2 0 5 4 ──────────────────────────────

[0126]

[Table 34] ────────────────────────────── Compound No. Dose g / a ABCD ─────── ５２ 52 10 5 5 5 5 53 10 2 0 0 0 54 2.52 0 5 5 5 55 2.52 3 4 5 5 56 2.52 0 1 5 5 57 2.52 3 4 5 5 58 2.52 1 4 5 5 60 2.52 3 5 5 5 61 2.52 5 5 5 5 65 2.52 4 4 4 5 66 2.52 4 5 5 5 68 2.52 2 4 5 5 69 2.52 0 3 5 5 70 2.52 2 1 5 5 71 2.52 1 1 5 5 72 2.52 4 4 5 5 73 2.52 5 4 5 5 74 2.52 4 4 5 5 75 2.52 4 3 5 5 76 2.52 0 0 5 5 77 2.52 0 0 3 5 79 2.52 3 4 5 5 80 2.52 1 0 5 5 ──────────────────────────────

[0127]

[Table 35] 化合物 Compound No. Positive dose g / a ABCD ─────── ８１ 81 2.52 5 4 5 5 83 2.52 3 0 0 5 84 2.52 3 5 5 5 85 2.52 5 5 5 5 86 2.52 0 0 5 5 87 2.52 0 2 5 5 88 2.52 2 4 5 5 89 2.52 0 4 5 5 90 2.52 0 0 5 5 92 2.52 3 3 5 5 93 2.52 0 2 4 5 94 2.52 0 1 5 5 95 2.52 5 5 5 5 96 2.52 5 5 5 5 97 2.52 3 4 5 5 98 2.52 4 5 5 5 99 2.52 4 5 5 5 100 2.52 0 3 5 5 101 2.52 3 5 5 5 103 2.52 5 3 5 5 104 2.52 5 2 5 5 106 2.52 2 3 5 5 107 2.52 0 1 5 5 ──────────────────────────────

[0128]

[Table 36] 化合物 Compound No. Positive dose g / a ABCD ─────── １０８ 108 2.52 1 2 5 5 109 2.52 3 2 5 5 110 2.52 2 2 5 5 111 2.52 5 1 5 5 112 2.52 5 2 5 5 113 2.52 5 0 5 5 115 2.52 2 3 5 5 116 2.52 3 0 5 0 117 2.52 5 3 5 5 119 2.52 5 2 5 5 120 2.52 4 2 5 5 121 121 2.52 0 0 5 5 122 2.52 0 0 0 5 123 2.52 1 1 5 5 124 2.52 0 0 5 5 125 2.52 4 1 5 5 126 2.52 4 2 5 5 127 2.52 1 1 5 5 128 2.52 4 4 5 5 129 2.52 0 1 5 5 130 2.52 1 1 5 5 131 2.52 1 0 0 1 132 2.52 3 5 5 5 ──────────────────────────────

[0129]

[Table 37] 化合物 Compound No. Drug dose g / a ABCD ─────── １３ 133 2.52 2 0 0 3 134 2.52 3 2 5 4 135 2.52 1 2 5 5 136 2.52 1 0 5 5 137 2.52 1 0 5 5 138 2.52 5 5 5 5 139 2.52 3 5 5 5 140 2.52 0 5 5 144 144 2.52 4 3 5 5 145 2.52 4 4 5 5 146 2.52 3 2 4 5 147 2.52 1 0 5 5 148 2.52 1 3 5 4 ──────────────────────────────

[0130]

[Table 38] Herbicidal effect test by soil treatment化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 1 25 5 5 5 4 5 5 5 5 5 5 4 1 0 0 3 4 2 6.3 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 4 6.3 2 2 0 0 0 0 2 0 0 0 0 0 0 0 0 0 6 6.3 0 3 0 0 3 0 5 0 0 0 0 0 0 0 0 1 7 6.3 0 3 0 0 2 0 5 0 0 0 0 0 0 0 0 4 8 6.3 0 3 0 0 2 0 5 0 0 0 0 0 0 0 0 3 9 6.3 0 4 0 0 0 0 3 0 2 0 0 0 0 0 0 1 10 6.3 0 5 0 0 4 0 3 0 4 2 0 0 0 0 0 2 11 6.3 0 3 0 0 0 0 3 0 0 0 0 0 0 0 0 1 12 6.3 0 3 0 0 0 0 4 0 0 0 0 0 0-0 1 14 6.3 3 5 3 2 3 0 5 2 5 5 0 0 0 0 0 4 15 6.3 0 3 0 0 3 0 5 2 4 5 0 0 0 0 0 4 16 6.3 2 2 0 2 3 0 4 0 4 5 0 0 0 0 0 1 17 6.3 4 5 0 0 3 0 2 0 0 0 0 0 0 0 0 1 18 6.3 5 5 5 2 5 0 5 0 5 2 0 0 0 0 1 4 19 6.3 5 5 3 3 4 0 5 0 3 3 0 0 0 0 0 4 21 6.3 5 5 2 0 3 0 5 0 3 0 0 0 0 0 0 1 22 6.3 3 5 0 0 2 0 4 0 0 0 0 0 0 0 0 3 24 6.3 0 0 0 0 3 0 2 0-5 0 0 0 0 0 1 25 6.3 0 0 0 0 3 0 3 0 3 3 0 0 0 0 0 3 26 6.3 5 5 2 3 5 3 5 0 5 5 0 0 0 0 0 5 27 6.3 4 0 0 0 3 0 5 0 0 0 0 0 0 0 0 0 ────────────────────────────────── ──

[0131]

[Table 39] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ２８ 28 6.3 3 3 0 0 3 0 3 0 0 0 0 0 0 0 0 1 29 6.3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 1 30 6.3 0 0 0 2 0 0-0 0 0 0 0 0 0 0 0 31 6.3 0 0 0 0 0 0-0 4 0 0 0 0 0 0 0 32 6.3 0 0 0 0 0 0 2 0 2 2 0 0 0 0 0 1 33 6.3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 34 6.3 0 0 0 0 0 0 3 0 4 0 0 0 0 0 0 1 35 6.3 0 0 0 2 2 0 2 0 0 0 0 0 0 0 0 1 36 6.3 0 3 0 0 3 0 5 0 5 3 0 0 0 0 0 3 37 6.3 3 5 0 2 4 0 5 0 4 4 0 0 0 0 0 4 38 6.3 0 0 0 0 3 0 4 0 2 0 0 0 0 0 0 4 40 6.3 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 41 6.3 3 5 0 0 4 0 5 0 5 5 0 0 0 0 0 4 42 6.3 4 5 0 0 4 0 5 0 5 5 0 0 0 0 0 4 43 25 3 3 1 1 1 0 5 0 5 2 0 0 0 0 0 1 44 25 5 5 3 3 5 5 5 5 5 5 0 5 0 3 4 4 45 6.3 3 4 3 1 4 0 5 0 5 5 0 0 0 0 1 2 46 6.3 4 5 1 1 4 0 5 3 5 5 0 0 0 0 3 3 48 25 5 5 4 3 5 2 5 2 5 5 1 3 0 0 2 3 49 25 5 5 1 1 1 1 5 1 5 5 0 1 0 0 3 3 50 6.3 0 0 0 0 1 0 5 0 2 3 0 0 1-0 0 52 25 25 5 5 5 5 5 4 5 4 5 5 1 4 0 0 4 4 53 25 3 0 0 4 0 0 3 0 3 0 0 0 0 0 0 4 ───────────────────────────────── ───

[0132]

[Table 40] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ５４ 54 6.3 1 4 0 0 1 0 5 0 5 3 1 0 0 0 0 1 55 6.3 3 3 1 1 0 0 4 0 5 3 0 0 0 0 0 1 56 6.3 4 5 0 0 0 0 5 0 5 4 1 0 0 0 0 1 57 6.3 6.3 0 4 0 0 1 0 4 0 0 0 0 0 0 0 0 0 58 6.3 3 4 0 0 0 0 5 0 5 2 0 0 0 0 0 1 59 6.3 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 60 6.3 3 5 0 0 0 0 4 0 3 0 0 0 0 0 0 0 61 6.3 3 2 0 3 0 0 4 0 5 3 0 0 0 0 0 2 63 6.3 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 64 6.3 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 65 6.3 5 5 0 0 4 0 5 0 5 5 0 2 0 0 0 3 66 6.3 4 5 3 3 4 0 5 0 5 5 0 0 0 0 0 3 68 6.3 5 4 1 0 4 0 5 0 5 5 0 2 0 0 0 3 69 6.3 4 5 0 0 1 0 5 0 5 5 0 1 0 0 0 3 70 6.3 5 5 0 0 0 0 0 0 5 4 0 0 0 0 0 0 71 6.3 5 5 0 0 1 0 5 0 5 5 0 0 0 0 0 2 72 6.3 3 4 0 0 5 1 3 1 5 5 0 0 0 0 0 3 73 6.3 5 5 0 0 4 1 5 1 5 5 0 1 0 0 0 3 74 6.3 3 1 5 2 5 0 5 0 5 5 0 0 0 0 2 4 75 6.3 3 5 1 0 4 0 5 0 5 5 0 0 0 0 0 4 76 6.3 0 0 2 2 0 0 5 0 5 5 0 0 0 0 0 4 77 6.3 1 1 0 0 0 0 5 0 5 5 0 0 0-0 4 79 6.3 0 0 0 0 0 0 3 0 5 5 0 0 0 0 0 3 ──────────────────────────────── ────

[0133]

[Table 41] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ８０ 80 6.3 3 4 0 0 0 0 4 0 5 5 0 0 0 0 0 0 81 6.3 5 1 0 0 0 0 3 0 4 5 0 0 0 0 0 2 82 6.3 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 84 6.3 325 0 0 2 0 2 0 5 4 0 3 0 0 0 4 85 6.3 2 4 0 0 3 0 5 0 5 5 0 0 0 0 0 4 86 6.3 3 3 0 0 0 0 3 0 4 5 0 0 0 0 0 2 87 6.3 0 0 0 0 0 0 0 0 5 4 0 0 0 0 0 2 88 6.3 2 3 0 0 0 0 3 0 5 0 0 0 0 0 0 0 89 6.3 0 0 2 0 0--0 0 5 0 0 0 0 0 3 90 6.3 0 2 0 0 0 0 3 0 5 3 1 5 0 0 0 2 91 6.3 2 2 0 0 2 0 3 0 0 0 0 0 0 0 0 0 92 6.3 1 3 0 0 1 0 3 0 5 4 0 5 0 5 0 0 93 6.3 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 95 6.3 1 1 0 5 0 1 4 0 5 5 0 0 0 0 0 4 96 6.3 5 4 1 4 5 0 5 0 5 4 0 0 0 0 0 4 97 6.3 1 3 0 0 0 0 3 0 5 5 0 0 0 0 0 2 98 6.3 3 3 2 0 4 0 4 0 5 5 0 2 0 0 0 4 99 6.3 3 3 4 0 5 0 5 0 5 5 0 0 0 0 1 4 100 6.3 0 2 0 0 0 0 4 0 4 5 1 0 0 1 0 3 101 25 0 1 0 0 0 0 0 0 5 5 0-0 0 0 3 102 6.3 5 5 0 0 1 0 5 0 5 4 0 0 0 0 0 2 103 6.3 3 5 1 3 0 0 2 0 5 4 0 0 0 0 0 2 104 6.3 4 5 0 0 0 0 1 0 5 5 0 0 0 0 0 2 ──────────────────────────────── ────

[0134]

[Table 42] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 105 6.3 4 3 0 0 1 2 1 0 0 0 0 0 0 0 0 0 106 6.3 3 5 0 0 4 0 5 0 5 5 0 0 0 0 0 3 107 6.3 0 0 0 0 0 0 3 0 5 4 0-0 0 0 2 108 6.3 1 2 0 0 0 0 4 0 5 5 0 0 0 0 0 2 109 6.3 0 3 0 0 0 0 0 0 5 4 0-0 0 0 2 110 6.3 0 1 0 0 0 0 5 0 4 3 0 0 0 0 0 2 111 6.3 0 5 0 0 1 0 3 0 5 5 0-0 0 0 1 112 6.3 5 2 0 0 0 0 0 0 0 4 0-0 0 0 2 113 6.3 1 4 0 0 0 0 3 0 5 5 0-0 0 0 2 115 6.3 0 0 0 0 0 0 0 0 5 3 0-0 0 0 0 116 6.3 0 0 5 0 0 0 1 0 5 0 0 0 0 0 0 1 117 6.3 0 5 0 0 0 0 1 0 0 0 0 0 0 0 0 0 118 6.3 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0 0 119 6.3 0 5 5 1 5 0 5 0 5 4 0 1 0 0 0 4 120 6.3 0 1 0 0 5 0 4 0 5 1 0 0 0 0 0 0 123 6.3 0 0 0 0 0 0 3 0 3 0 0 0 0 0 0 0 124 6.3 3 0 0 0 0 0 0 0 5 0 0 0 0 0 0 1 125 6.3 0 0 0 0 3 0 2 0 3 4 0 0 0 0 0 0 126 6.3 1 0 0 0 0 0 3 0 5 2 0 0 0 0 0 0 128 6.3 5 5 0 0 5 0 5 0 0 0 0 0 0 0 0 0 129 6.3 6.3 0 0 0 0 1 0 5 0 5 0 0 0 0 0 0 0 130 6.3 0 3 0 0 0 0 4 0 4 3 0 0 0 0 0 1 131 6.3 0 0 0 0 0 0 4 0 4 5 0 0 0 0 0 1 ──────────── ────────────────────────

[0135]

[Table 43] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 132 6.3 0 5 0 0 5 0 5 0 4 4 0 0 0 0 0 2 133 6.3 0 0 0 0 0 0 2 0 4 0 0 0 0 0 0 1 134 6.3 0 3 0 0 0 0 5 0 4 4 0 0 0 0 0 0 135 135 6.3 0 3 0 0 3 0 5 0 5 3 0 0 0 0 0 0 136 6.3 1 3 0 0 4 0 5 0 5 4 0 0 0 0 0 3 137 6.3 0 0 0 0 0 0 1 0 4 1 0 0 0 0 0 0 138 6.3 2 4 0 0 0 0 3 0 4 4 0 0 0 0 0 3 139 6.3 0 0 0 0 0 0 1 0 4 3 0 0 0 0 0 0 140 6.3 0 4 0 2 5 0 5 0 5 5 0 0 0 0 0 2 141 6.3 0 0 0 2 2 0 3 0 3 3 0 0 0 0 0 3 142 6.3 1 1 0 0 2 0 3 0 0 0 0 0 0 0 0 0 143 6.3 6.3 0 0 2 0 0 0 0 0 1 3 0 0 0 0 0 2 144 6.3 3 2 0 0 0 0 5 0 3 3 0 0 0 0 0 3 145 6.3 4 5 1 0 1 0 5 0 5 5 0 0 0 0 0 3 146 6.3 0 0 0 0 2 0 5 0 1 1 0 1 0 0 0 1 147 6.3 3 2 5 0 0 0 5 0 1 1 0 0 0 0 0 3 148 6.3 3 3 1 2 3 0 5-5 5 0 0 0 0 0 2 ──────────────────── ────────────────

[0136]

[Table 44] Herbicidal effect test by foliage treatment化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 1 25 5 4 3 4 5 5 5 3 5 5 2 3 1 0 1 3 2 6.3 0 0 0 2 0 0 0 0 3 3 0 0 0 0 0 1 3 6.3 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 4 6.3 0 2 2 0 0 0 0 0 3 3 0 0 0 0 0 1 5 6.3 0 0 0 0 3 1 3 1 2 2 0 0 0 2 0 0 6 6.3 0 0 0 0 3--0 0 0 0 0 0 1 0 0 7 6.3 0 3 0 0 4 5 3 4 5 0 0 0 1 2 0-8 6.3 3 2 0 0 3 3 5 3 5 0 0 0 0 1 0 1 9 6.3 0 3 0 0 4 4 3 3 5 3 0 0 0 1 0 2 10 6.3 0 0 0 0 3-2 0 5 0 0 0 0 2 0 0 11 6.3 0 0 0 0 0 0-0 0 0 0 0 0 1 0 0 12 6.3 0 0 0 0 3 0 3 0 4 0 0 0 0 1 0 0 13 6.3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 14 6.3 4 4 0 0 4 3 4 4 5 4 0 1 0 2 0 1 15 6.3 2 3 0 2 5 4 4 4 5 4 0 0 1 1 0 1 16 6.3 2 3 0 2 3 3 5 3 3 3 0 0 0 0 0 0 17 6.3 0 0 0 0 2 0 3 0 5 0 0 0 1 1 0 0 18 6.3 4 3 3 3 2 4 3 4 5 2 0 0 1 2 1 1 19 6.3 4 4 3 2 2 2 4 3 5 3 0 0 1 1 0 1 20 6.3 0 0 0 0 2 3 3 2 5 0 0 0 0 1 0 1 21 6.3 0 2 0 2 2 4 3 4 5 3 0 0 1 2 0 1 22 6.3 4 4 0 0 3 3 3 3 5 3 0 0 1 2 0 2 ────────────────────────────────────

[0137]

[Table 45] ──────────────────────────────────── Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 23 6.3 0 0 0 0 0 2 2 2 0 0 0 0 0 0 0 1 24 6.3 0 0 0 0 0 0 2 0 5 0 0 0 0 1 0 1 25 6.3 0 0 0 0 0 0 0 0 4 3 0 0 0 1 0 1 26 6.3 0 0 0 2 2 3 3 0 5 3 0 0 0 0 0 2 27 6.3 0 2 0 0 3 3 3 2 0 0 0 0 1 1 0 0 28 6.3 0 0 0 2 3 3 3 3 5 0 0 0 1 1 0 0 29 6.3 0 2 0 0 0 0 2 0 0 0 0 0 0 0 0 0 30 6.3 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 0 31 6.3 0 0 0 2 3 5 4 4 5 2 0 0 2 2 0 0 32 6.3 -3 0 0 3 5 4 4 5 4 0 0-2 0 3 33 6.3 0 2 0 0 0 4 2 4 5 2 0 0 0 0 0 2 34 6.3 0 3 0 2 0 4 3 3 4 2 0 0 0 0 0 1 35 6.3 0 2 0 0 2 2 3 0 4 0 0 0 1 1 0 1 36 6.3 0-0 2 3 3 3 0 3 3 0 0 1 1 0 1 37 6.3 0-0 0 3 3 4 3 5 3 0 0 1 1 0 1 38 6.3 0 0 0 0 2 2 3 2 5 3 0 0 0 0 0 1 39 6.3 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 40 6.3 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 41 6.3 2 2 0 0 2 3 2 4 5 3 0 0 1 2 0 2 42 6.3 3 3 0 0 2 2 3 2 5 3 0 0 1 1 0 1 43 25 0 0 1 1 0-3 0 4 0 0 0 0 0 0 0 44 25 5 5 0 2 5 2 5 1 5 3 0 1 0 1 1 3 45 6.3 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 ──────────────────────────────── ────

[0138]

[Table 46] ──────────────────────────────────── Compound No. Drug dose g / a GHIJKLMNOP abcdef ４６ 46 6.3 0 0 0 0 0 1 0 0 1 1 0 0 0 0 0 0 47 6.3 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 48 25 1 0 0 1 2 0 1 0 4 4 0 0 0 0 1 3 49 25 0 0 0 0 2 3 1 0 5 3 0 0 0 0 0 0 52 25 2 3 1 2 1 3 0 2 5 4 2 1 0 1 1 3 53 25 0 0 0 0 0 2 0 0 5 1 0 0 0 0 0 0 54 6.3 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 55 6.3 0 0 0 0 0 0 0-5 0 0 0 0 0 0 0 56 6.3 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 57 6.3 0 0 0 0 0 0 0 0 5 2 0 0 0 0 0 0 58 6.3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 60 6.3 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 61 6.3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 65 6.3 0 0 0 0 0 1 0 0 3 0 0 0 0 0 0 0 66 6.3 0 0 0 0 0 1 0 0 4 0 0 0 0 0 0 0 68 6.3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 69 69 6.3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 70 6.3 0 0 0 0 0 1 0 0 5 0 0 0 0 0 0 0 71 6.3 0 0 0 0 0 0 0 0 5 4 0 0 0-0 0 72 6.3 0 0 0 1 0 1 0 0 5 0 0 0 0 0 0 0 73 6.3 0 0 0 0 0 0 0 0 0 3 0 0 0 0-0 0 74 6.3 0 0 0 0 0 1 0 0 3 2 0 0 0 0 0 0 75 6.3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 ────────────────────────────────── ──

[0139]

[Table 47] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 76 6.3 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 1 77 6.3 0 0 0 0 0 0 0 0 3 1 0 0 0 0 0 0 79 6.3 0 0 0 0 0 1 0 0 4 1 0 0 0 0 0 0 80 6.3 0 0 0 0 0 3 1 0 5 3 0 0 0 0 0 1 81 6.3 0 0 0 0 0-0 0 5 0 0 0 0 0 0 0 83 6.3 0 0 0 0 0 0-0 4 0 0 0 0 0 2 0 84 6.3 0 0 0 0 0 2 1 1 3 0 0 0 0 0 0 0 85 6.3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 86 6.3 0 0 0 0 0 0 1 0 0 2 0 0 0 0 0 0 87 6.3 0 0 0-0 0 0 0 3 0 0 0 0 0 2 0 88 6.3 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 89 6.3 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 90 6.3 0 0 0 0 0 2 0 0 2 0 0 0 0 0 0 0 92 6.3 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 93 25 0 0 0 0 0 0 1 0 4 2 0 0 0 0 0 0 94 25 0 0 0 0 1 0 1 5 3 0 0 0 0 0 0 0 95 6.3 0 0 0 0 0 0 0 0 3 2 0 0 0 0 0 1 96 6.3 0 0 2 1 2 1 0 0 5 3 0 0 0 0 0 0 97 6.3 0 0 0 0 0 0 0 0 3 1 0 0 0 0 0 0 98 25 0 0 0 0 0 0 0 0 4 1 0 0 0 0 1 1 99 25 0 0 0 1 0 0 0 0 5 3 0 0 0 0 1 2 100 6.3 0 0 0 0 0 0 0 0 5 1 0 0 0 0 0 1 101 6.3 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 ───────────────────────────────── ───

[0140]

[Table 48] ──────────────────────────────────── Compound No. Positive dose g / a GHIJKLMNOP abcdef １０３ 103 6.3 0 0 0 0 0 0 0 0 3 1 0 0 0 0 0 0 104 6.3 0 0 0 0 0 1 0 0 1 1 0 0 0 0 0 0 105 6.3 0 0 0 0 0 0 0 0 1 2 0 0 0 0 0 0 106 6.3 0 0 0 0 0 3 0 0 2 0 0 0 0 0 0 0 107 6.3 0 0 0 0 0 1 0 0 2 0 0 0 0 0 0 1 108 6.3 0 0 0 0 0 0 0 0 5 2 0 0 0 0 0 1 109 6.3 0 0 0 0 0 2 0 0 5 3 0 0 0 0 0 2 110 6.3 0 0 0 0 5-5 0 3 0 0 0 0 4 0 1 111 6.3 6.3 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 1 112 6.3 0 0 0 0 0 2 0 0 5 2 0 0 0 0 0 0 113 6.3 6.3 0 0 0 0 0 0 0 0 4 1 0 0 0 0 0 1 115 6.3 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 117 6.3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 119 6.3 0 0 0 2 0 1 0 0 5 0 0 0 0 0 0 0 120 6.3 0 0 0 0 0 3 0 1 5 1 0 0 0 0 0 1 121 6.3 0 0 0 0 0 0 0 0 5 1 0 0 0 0 0 1 122 6.3 0 0 0 0 0 2 0 0 5 1 0 0 0 0 0 1 126 6.3 0 0 0 0 0 0 0 0 4 1 0 0 0 0 0 0 127 6.3 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 128 6.3 0 0 0 0 0 2 4 0 0 0 0 0 0 0 0 0 129 6.3 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 1 130 6.3 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 131 6.3 0 0 0 0 0 0 0 0 5 3 0 0 0 0 0 2 ──────────── ────────────────────────

[0141]

[Table 49] 化合物 Compound No. Dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 132 6.3 0 0 0 0 0 0 0 0 4 2 0 0 0 0 0 0 133 6.3 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 1 134 6.3 0 0 0 0 0 0 0 0 5 1 0 0 0 0 0 1 135 135 6.3 0 0 0 0 0 0 0 0 4 1 0 0 0 0 0 1 136 6.3 0 0 0 0 0 0 0 0 4 2 0 0 0 0 0 0 137 6.3 6.3 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 138 6.3 0 0 0 0 0 0 0 0 5 3 0 0 0 0 0 2 139 6.3 0 0 0 0 0 0 0 0 5 3 0 0 0 0 0 1 140 6.3 0 0 0 0 0 0 0 0 3 1 0 0 0 0 0 0 141 141 6.3 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 143 6.3 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 144 144 6.3 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 1 145 6.3 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 146 6.3 0 0 0 0 0 0 0 0 1 2 0 0 0 0 0 0 147 6.3 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 ─────────── ──────────────────────── [Test Example-7] Cucumber powdery mildew control effect test 1.5-leaf stage grown in a 7 cm diameter pot A cucumber (variety: Sagami Hanjiro) was sprayed with a chemical solution prepared by diluting the compound emulsion of the present invention with water to a concentration of 500 ppm using a spray gun and spraying 20 ml per pot.

The day after spraying, cucumber powdery mildew ( Spha)
by spraying a spore suspension (3 × 10 ⁵ cells / ml) of erotheca fuliginea), it was inoculated. afterwards,
In a greenhouse, the ratio of the lesion area formed 9 days after inoculation to the inoculated leaves was measured, and the control value was calculated according to the following formula. Control value = [1- (area ratio of lesion in treated group / area ratio of lesion in untreated section)] × 100 As a result, the following compounds showed a control value of 100.

Compound No. 2, No. 3, No. 4,
No. 9, No. 10, No. 14, No. 15, N
o. 17, No. 19, no. 21, no. 41, N
o. 42, No. 50, no. 51, No. 52, N
o. 54, no. 55, no. 57, no. 59, N
o. 60, no. 61, no. 62, No. 64, N
o. 65, no. 66, no. 67, no. 68, N
o. 69, no. 70, no. 71, No. 72, N
o. 73, no. 75, no. 76, no. 77, N
o. 79, no. 80, no. 81, no. 82, N
o. 83, no. 84, no. 85, no. 86, N
o. 87, no. 91, no. 93, no. 94, N
o. 96, no. 97, no. 98, no. 106, N
o. 108, no. 110, no. 113, no. 11
9, No. 120, no. 121, no. 131, N
o. 133, no. 134, no. 136, no. 14
1, No. 143, no. 145, no. 146, N
o. 148 [Test Example-8] Barley powdery mildew control effect test A 3.5-leaf stage barley (cultivar: Saitama Sekitori No. 2) grown in a pot having a diameter of 5.5 cm was diluted with water to dilute the present compound emulsion. The chemical solution adjusted to 500 ppm was sprayed using a spray gun at 20 ml per pot.

On the day after spraying, spores of barley powdery mildew ( Erysiphe graminis ) formed on the diseased leaves were directly inoculated. Then, the plant was placed in a greenhouse, the ratio of the lesion area formed 9 days after inoculation to the inoculated leaves was measured, and the control value was calculated according to the following formula. Control value = [1- (area ratio of lesion in treated area / area ratio of untreated area)] × 100 As a result, the following compounds exhibited a control value of 70 to 100.

Compound No. 2, No. 3, No. 4,
No. 6, no. 9, No. 10, No. 12, No.
14, No. 15, No. 17, No. 19, no. 2
1, No. 36, no. 37, no. 39, no. 4
0, No. 42, No. 44, no. 45, no. 4
6, no. 47, no. 48, no. 50, no. 5
1, No. 52, no. 53, no. 54, no. 5
5, no. 56, no. 57, no. 58, no. 5
9, No. 60, no. 61, no. 62, No. 6
4, no. 65, no. 66, no. 67, no. 6
8, No. 69, no. 70, no. 71, No. 7
2, No. 73, no. 75, no. 76, no. 7
7, no. 79, no. 80, no. 81, no. 8
2, No. 83, no. 84, no. 85, no. 8
6, no. 87, no. 89, no. 90, no. 9
2, No. 93, no. 94, no. 95, no. 9
6, no. 97, no. 98, no. 99, no. 10
0, No. 101, No. 102, no. 103, N
o. 104, no. 105, no. 111, No. 11
2, No. 113, no. 114, No. 115, N
o. 116, no. 117, no. 119, no. 12
0, No. 121, no. 122, No. 125, N
o. 126, no. 127 [Test Example-9] Wheat leaf rust control test A 3.5-leaf wheat (cultivar: Norin 61) grown in a pot having a diameter of 5.5 cm was diluted with water to prepare a compound emulsion of the present invention at 500 ppm. The sprayed chemical was sprayed with a spray gun at a rate of 20 ml per pot.

The day after spraying, wheat leaf rust fungus ( Pucci)
nia recondita ) (3 × 10
⁵ cells / ml) and inoculated. The inoculated wheat was placed in an inoculation box at a temperature of 25 ° C. and a humidity of 95% or more all day and night. Then, it was placed in a greenhouse, the lesion area formed 9 days after inoculation was measured, and the control value was calculated according to the following formula. Control value = [1- (area ratio of lesion in treated area / area ratio of untreated area)] × 100 As a result, the following compounds exhibited a control value of 70 to 100.

Compound No. 2, No. 3, No. 4,
No. 6, no. 9, No. 10, No. 12, N
o. 14, No. 15, No. 17, No. 19, N
o. 21, no. 37, no. 39, no. 40, N
o. 42, No. 44, no. 52, no. 53, N
o. 54, no. 57, no. 60, no. 61, N
o. 65, no. 69, no. 70, no. 71, N
o. 72, no. 73, no. 74, no. 75, N
o. 76, no. 77, No. 79, no. 80, N
o. 81, no. 82, no. 83, no. 84, N
o. 85, no. 86, no. 87, no. 92, N
o. 93, no. 94, no. 95, no. 96, N
o. 97, no. 98, no. 99, no. 100, N
o. 101, No. 102, no. 103, no. 10
4, no. 111, No. 112, No. 113, N
o. 115, no. 116, no. 117, no. 11
8, No. 119, no. 120, no. 121, N
o. 122, No. 129, no. 130, no. 13
1, No. 132, no. 133, no. 134, N
o. 135, no. 136, no. 138 [Test Example-10] Cucumber powdery mildew control effect test (low concentration) The following compound emulsions of the present invention were added to cucumber (variety: Sagamihanjiro) at the 1.5 leaf stage grown in a 7 cm diameter pot. The solution diluted to 100 ppm was prepared by spraying 20 ml per pot using a spray gun.

Compound No. 2, No. 4, no. 1
7, no. 41, no. 42, No. 60, no. 6
1, No. 65, no. 67, no. 68, no. 6
9, No. 70, no. 73, no. 77, No. 7
9, No. 80, no. 81, no. 84, no. 8
6, no. 87, no. 93, no. 97, no. 10
8, No. 110, no. 131, no. 133, N
o. 134 Cucumber powdery mildew on the day after spraying ( Sphaerothe
ca fuliginea spore suspension (3 × 10 ⁵⁾
Per ml) and inoculated. Then put it in the greenhouse,
The ratio of the lesion area formed 9 days after the inoculation to the inoculated leaves was measured, and the control value was calculated according to the following formula.

Control value = [1- (area ratio of lesion in treated area / area ratio of untreated area)] × 100 As a result, all the compounds subjected to the test showed a control value of 90 or more. [Test Example-11] Barley powdery mildew control effect test (low concentration) The following compound emulsion of the present invention was applied to 3.5-leaf barley (variety: Saitama Sekitori No. 2) grown in a pot having a diameter of 5.5 cm. Was diluted with water and adjusted to 50 ppm, and a spray gun was used to spray 20 ml per pot.

Compound No. 39, no. 42, No. 4
4, no. 45, no. 46, no. 47, no. 4
8, No. 51, No. 52, no. 53, no. 5
5, no. 56, no. 57, no. 58, no. 6
0, No. 61, no. 62, No. 68, no. 6
9, No. 70, no. 71, No. 72, no. 7
3, No. 75, no. 76, no. 77, No. 8
0, No. 81, no. 83, no. 84, no. 8
5, no. 86, no. 87, no. 90, no. 9
2, No. 93, no. 94, no. 95, no. 9
6, no. 97, no. 98, no. 99, no. 10
0, No. 101, No. 102, no. 103, N
o. 104, no. 105, no. 111, No. 11
2, No. 113, no. 114, No. 115, N
o. 116, no. 117, no. 119, no. 12
0, No. 121, no. 122, No. 125, N
o. 126, no. 127 Barley powdery mildew fungus ( Er ) formed on diseased leaves the day after spraying
spores of Ysiphe graminis ) were inoculated directly. Then, put in a greenhouse, measure the ratio of the lesion area formed 9 days after inoculation to the inoculated leaves, according to the following formula,
The control value was calculated.

Control value = [1- (area ratio of lesion in treated area / area ratio of untreated area)] × 100 As a result, all compounds used in the test showed a control value of 90.
The above is shown. [Test Example-12] Wheat leaf rust control test (low concentration) The following compound emulsions of the present invention were each added to water in 3.5-leaf stage wheat (cultivar: Norin 61) grown in a 5.5 cm diameter pot. The chemical solution diluted to 50 ppm was sprayed using a spray gun to spray 20 ml per pot.

Compound No. 14, No. 42, No.
44, no. 74, no. 83, no. 86, no. 9
2, No. 93, no. 94, no. 96, no. 9
7, no. 98, no. 100, no. 102, no.
103, no. 104, no. 111, No. 112,
No. 116, no. 117, no. 118, no. 1
19, no. 120, no. 121, no. 122, N
o. 133, no. 134, no. 135, no. 13
8 The day after spraying, wheat leaf rust fungus ( Puccinia re)
spore suspension condita) (3 × 10 ⁵ cells / ml)
Was sprayed and inoculated. Inoculated wheat at a temperature of 25
They were placed in an inoculation box at 95 ° C. and a humidity of 95% or more all day and night. afterwards,
Placed in a greenhouse, the lesion area formed 9 days after inoculation was measured, and the control value was calculated according to the following formula.

Control value = [1- (area ratio of lesion in treated area / area ratio of untreated area)] × 100 As a result, all of the following compounds subjected to the test showed a control value of 90 or more.

[0154]

The compounds of the present invention have excellent effects as herbicides, plant growth regulators and fungicides.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/88 C07D 401/12 239 C07D 401/12 239 403/06 209 403/06 209 233 233 403/12 231 403/12 231 405/06 239 405/06 239 413/06 239 413/06 239 413/12 239 413/12 239 A01N 43/82 101 (72) Inventor Takumi Mikashima 722 Tsuboi-cho, Funabashi-shi, Chiba 1 Nissan Chemical Industries Co., Ltd. (72) Inventor Tsutomu Nawamaki 1470, Shirooka, Shirooka-cho, Minami-Saitama-gun, Saitama Nissan Kagaku Kogyo Co., Ltd. (72) Kazuhisa Sudo, 1470, Shirooka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industries, Ltd. Within the Institute for Biological Sciences (72) Inventor Takashi Furusato 1470, Shirooka, Shirooka-cho, Minami-Saitama-gun, Saitama Nissan Kagaku Kogyo Co., Ltd. Biological Science Laboratory Co., Ltd.

Claims (7)

[Claims] 1. A compound of formula (I):[Wherein X is a fluorine atom, a chlorine atom, a bromine atom or an iodine
R represents C₁-C_TenAlkyl group, optionally substituted
Optionally substituted phenyl group (provided that the substituent is C ₁-C
₈Alkyl group, C₁-C₈Alkoxy group, C₁-C₈C
Loalkyl group, halogen atom, cyano group, C₁-C₈C
Lower alkoxy, nitro or C₁-C _FourAlkoxy
It is arbitrarily selected from carbonyl groups. ), -Q-place
A substituted phenyl group [Q is a saturated or unsaturated branched
Good C₁-C₆Represents an alkylene chain of a substituted phenyl
Represents an optionally substituted phenyl group (provided that the
The group is C₁-C₈Alkyl group, C₁-C₈An alkoxy group,
C₁-C₈Haloalkyl group, halogen atom, cyano group,
Nitro group, C₁-C₈Haloalkoxy group or C₁-C
_FourArbitrarily selected from among alkoxycarbonyl groups
You. ). ], -QO-substituted phenyl group (Q and
And substituted phenyl groups have the same meaning as described above. )
Or optionally substituted unsaturated, saturated, or
Is a partially saturated 5- or 6-membered heterocyclic ring (a heterocyclic
Gin, pyrimidine, triazine, pyridazine, pyrazo
, Imidazole, oxazole, oxadiazole
Or a thiazole ring. As a substituent, halogen
Atom, C₁-C_FourAlkoxy group, C ₁-C_FourAlkyl
Group, a phenyl group which may be substituted with a halogen atom,
C₁-C_FourHaloalkyl group or C₁-C_FourHalo alco
Xyl groups. Y represents -N (R1) R
2 [where R1 is a hydrogen atom, C₁-C₈Alkyl group, C
_Three-C₈Alkenyl group, C_Three-C₈Alkynyl group or
C₁-C_FourAlkoxy (C₁-C_Four) Alkyl group
And R2 is a hydrogen atom, C₁-C₈Alkyl group, C₁-C
₈Haloalkyl group, C_Three-C₈Alkenyl group, C_Three-C
₈Alkynyl group, C _Three-C₈Cycloalkyl group, C_Three−
C₈Cycloalkyl (C₁-C_Four) Alkyl group, C₁−
C₈Alkoxy (C₁-C_Four) Alkyl group, (C₁-C
_FourAlkyl) _TwoAmino (C₁-C_Four) Alkyl group, C₁
-C₆An alkoxy group, (C₁-C_Four)_ThreeCyril (C₁−
C_Four) Alkyl group, (C₁-C_Four) Alkoxy (C₁−
C_Four) Alkoxy (C₁-C_Four) Alkyl group, substituted
Nyloxy (C₁-C_Four) Alkyl group, (halogen atom
Substitutes an optionally substituted phenyloxy group with
Expressed as a phenyloxy group. ), 2-tetrahydropyrani
Le (C₁-C_Four) Alkyl group, 2-tetrahydrofurani
Le (C₁-C_Four) Alkyl groups, 2,2-dimethyl-1,
3-dioxolan-4-yl- (C₁-C_Four) Alkyl
Group, -Q-0-substituted phenyl group (Q-substituted phenyl group is
Represents the same meaning as above. ), C₁-C₈Acyl group, C
_Two-C₈Alkenyloxy (C₁-C_Four) Alkyl group, C_Three
-C₈Alkynyloxy (C₁-C_Four) Alkyl group, C₁−
C_FourHaloalkoxy (C₁-C_Four) Alkyl group, [C₁-C
_FourAlkoxy (C₁-C_Four) Alkyl)_Two(C₁-C_Four) Al
Kill group, 3-tetrahydrofuranyl group, 2,2- (C₁
-C_FourAlkoxy)_Two-Cyclohexyl group, C₁-C_FourAl
Kirchio (C₁-C_Four) Alkyl group, C₁-C_FourHalo alco
Kishi (C₁-C_Four) Alkoxy (C₁-C_Four) Alkyl groups,
Cyano (C₁-C_Four) Alkyl group, C₁-C_FourAlkoxyka
Rubonil (C₁-C_Four) Alkyl groups, optionally substituted
A phenyl group (substituent is a halogen atom, C₁
-C₆Alkyl group, C₁-C_FourAlkoxy group, C₁-C
_FourHaloalkyl group, or C₁-C_FourHaloalkoxy group
Arbitrarily selected from ) Or -Q-substituted phenyl group
(Q and substituted phenyl have the same meaning as described above.)
Represents ], -NHOR3 (R3 is C₁-C₈Archi
Group, C_Three-C₈Alkenyl group, C_Three-C₈Alkynyl
Group optionally substituted with a group or a halogen atom.
Represents an benzyl group. ), -NHCH_TwoCO_Two(C₁-C_ThreeA
Alkyl), a nitrile group, a halogen atom, -NHCON
(R4) R5 (R4 and R5 are each independently a hydrogen atom
Or C₁-C₈Represents an alkyl group. ), Phthalimi
Group, morpholino group, 1-imidazolyl group, pyrazole
-1-yl group, triazol-1-yl group, 3- (3-
Fluoropropyl) thiazoline-2-imino group, 2-
(4-chlorophenyl) -5,6-dihydro-1,3,
4-oxadiazin-4-yl group, -NHN (R4) R
5 (R4 and R5 represent the same meaning as described above), -N
HSO_TwoN (R4) R5 (R4 and R5 are as defined above)
Represents taste. ), -NHCO_TwoR3 (R3 is the same as above
Represents the meaning of ), -NHCOR3 (R3 is as defined above)
Express the meaning of ), -OR2 (R2 is as defined above)
Represents the meaning of ), -S-R2 (R2 is as defined above)
Indicates meaning. ) Or CH (R6)_Two(R6 is C₁−
C_FourRepresents an alkoxycarbonyl group or a nitrile group
You. ) Wherein R7 is a hydrogen atom, C₁-C_FourAlkyl
Group, C₁-C_FourHaloalkyl group, or substituted
Phenyl group (substituent is a halogen atom, C₁
-C_FourAlkyl group, C₁-C_FourAlkoxy group, C ₁-C_Four
Haloalkyl group, or C₁-C_FourHaloalkoxy group
Arbitrarily selected from ). A compound represented by the formula:
And their salts. 2. An agricultural chemical comprising the compound according to claim 1. 3. A herbicide comprising the compound according to claim 1. A fungicide containing the compound according to claim 1. 5. A plant growth regulator comprising the compound according to claim 1. 6. The compound according to claim 1, wherein X is a chlorine atom or a bromine atom, and salts thereof. 7. The compound according to claim 1, wherein R7 is a hydrogen atom, and salts thereof.