JP2000247975A - Heterocycle-condensed pyrimidinone derivative and herbicide containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound having high safety to important crops including rice and soybean, having high herbicidal activity against weeds including Scirpus juncoides and Monochoria vaginalis, therefore useful as a herbicide. SOLUTION: This new compound is a compound of formula I (Rf is a 1-4C haloalkyl; X and Y are each C, N or the like; X-Y is N=N or the like; A is N or CH; Z is O, S or the like; Rg is H, cyano or the like; R1 and R5 are each H or a halogen; R2 is nitro or the like; R3 is a 3-8C alkenyloxycarbonyl 1-4C alkyl or the like; R4 is H, OH or the like), e.g. 8-[2,7-difluoro-3,4-dihydro-3- oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-7,8-dihydro-5-trifluorometh ylimidazo[1,2- a]pyrimidin-7-one. The compound of formula I is obtained, for example, by reaction between a compound of formula II (R' is a 1-4C alkyl) and a compound of formula III and the like to form a compound of formula IV (Me is CH3) which is then reacted with sodium azide.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a herbicide containing a heterocyclic fused pyrimidinone derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, many herbicides have been put into practical use to protect important crops such as rice, soybean, wheat, corn, cotton, beet and the like from weed damage and to increase the productivity of these important crops. However, existing drugs still do not fulfill all the required functions.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies on the herbicidal action of a heterocyclic fused pyrimidinone derivative, and as a result, have found that the compound of the present invention represented by the following formula has an excellent herbicidal action. It was completed.

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

[0005]

Embedded image

[Wherein Rf is C₁-C_FourHaloalkyl group
X and Y each independently represent a carbon atom, nitrogen
X, Y and N represent an atom, an oxygen atom or a sulfur atom,
N, C (Ra) = C (Rb) (Ra and Rb are each independently
Standing hydrogen atom, halogen atom, C₁-C_FourAlkyl
Group, C₁-C_FourAlkoxy group, C₁-C_FourHaloalkyl
Group, hydroxyl group, amino group, mercapto group, carboxyl
Group, hydroxymethyl group, carbamoyl group, formyl
Group, C₁-C_FourAlkylcarbonyl group, C₁-C_FourArco
Xycarbonyl group, C₁-C_FourAlkylamino group, C_Two
-C ₆Alkenyl group, C_Two-C₆Alkynyl group, C₁-C
_FourAlkyl mercapto group, C_Three -C₆Alkenylamino
Group, C_Three-C₆Alkynylamino group, benzyloxy
Group, benzylamino group, C₁-C_FourAlkylsulfini
Group, C₁-C_FourAlkylsulfonyl and pyridyl groups
Or an optionally substituted phenyl (SP1) group (substituted
The optionally substituted phenyl (SP1) group refers to a halogen
Atom, C₁-C_FourAlkyl group, C₁-C_FourAn alkoxy group,
C₁-C_FourHaloalkyl group, C₁-C_FourHaloalkoxy group
Or phenyl which may be substituted by a phenyl group
Represents a radical. ). ), C (Ra) = N (Ra
Represents the same meaning as described above. ), N = C (Ra) (R
a has the same meaning as described above. ), CH (Ra) CH
(Rb) (Ra and Rb represent the same meaning as described above.)
You. ), CH_TwoCH_TwoCH_Two, CH = CHCH_Two, CH_TwoC
H = CH, NHC (Ra) Rb (Ra and Rb are as defined above.
Represents the same meaning as ), C (Ra) (Rb) NH
(Ra and Rb represent the same meaning as described above), C
(= O) C (= O), CH_TwoC (= O) NH, CH_TwoCH
_TwoSO_Two, C (= O) CH (Ra) (Ra is as defined above)
Indicates meaning. ), CH (Ra) C (= O) (Ra is before
Represents the same meaning as ), C (= O) NH, C (=
S) NH, NHC (= O), NHC (= S), C (=
O) C (Ra) = N (Ra represents the same meaning as described above.)
You. ), C (= O) C (Ra) = C (Rb) (Ra and
And Rb have the same meaning as described above. ), C (Ra) =
C (Rb) C (＝ O) (Ra and Rb are the same as above)
Indicates meaning. ), N = C (Ra) C (= O) (Ra is
Represents the same meaning as above. ), CH (Ra) C (=
O) NH (Ra represents the same meaning as described above), C
(= O) N (Ra) C (= O) (Ra is the same as above.
Represents taste. ), C (Ra) = NC (= O) (Ra is before
Represents the same meaning as ), C (Ra) O (Ra is before
Represents the same meaning as ), C (= O) O, OC (=
O) or SC (= O), wherein A is a nitrogen atom or
CH represents an oxygen atom, a sulfur atom, NRc (Rc
Is a hydrogen atom, C₁-C_FourAlkyl group, C₁-C_FourAlkoki
Cicarbonyl group, C₁-C_FourAlkoxycarbonylmethy
Or a phenyl (SP2) group which may be substituted
(An optionally substituted phenyl (SP2) group refers to
Logen atom, C₁-C_FourAlkyl group, C₁-C_FourAlkoki
Si group or C₁-C_FourSubstituted by a haloalkyl group
Represents a phenyl group which may be optionally substituted) or NNHRc
(Rc has the same meaning as described above), and Rg
Represents a hydrogen atom, a halogen atom, a cyano group, C₁-C_FourAl
Coxycarbonyl group, C_Three-C₆Alkenyl group, C_Three−
C₆Alkynyl group or C₁-C_FourRepresents an alkyl group,
R1 represents a hydrogen atom or a halogen atom, and R5 represents water
R 2 represents a hydrogen atom,
Halogen atom, nitro group, cyano group, thiocarbamoyl
Group, carbamoyl group, mercapto group, hydroxyl group,
Amino group, formyl group, carboxyl group, vinyl group,
Thynyl group, trimethylsilylethynyl group, cyanomethyl
Group, sulfamoyl group, phenyl group, benzyl group, C₁
-C₈Alkyl group, C_Three -C₈Alkenyl group, C_Three-C₈A
Rukinyl group, C₁-C_FourHaloalkyl group, C₁-C_FourAl
Coxy group, C₁-C_FourHaloalkoxy group, C_Three-C₈Halo
Alkenyl group, C_Three-C₈Haloalkynyl group, C₁-C_Four
Acyl group, C₁-C_FourAlkylsulfonyl group, C₁-C_Four
Alkylthio group, C₁-C_FourAlkoxy (C₁-C_Two) Al
Kill group, -CO_Two(C₁-C_FourAlkyl) group, -CON
(C₁-C_FourAlkyl)_TwoGroup, -CONH (C₁-C_FourA
Alkyl) group, -NH- (C₁-C_FourAlkyl) group, -N
(C ₁-C_FourAlkyl)_TwoGroup, -S-CO_Two(C₁-C_FourA
Alkyl) group, —O—Q—CO _Two(C₁-C_FourAlkyl) group
(However, Q may be saturated or unsaturated branched
, Halogen atom, C₁-C_FourAlkoxy group, C₁-C_Four
Alkoxycarbonyl group, cyano group, phenyl group, C₁
-C_FourHaloalkyl group, C₁-C_FourAlkoxy (C ₁-C
_Four) Alkoxy group, C₁-C_FourAcyl group, C₁-C_FourAl
Koxy (C₁-C_Four) With an alkyl group or oxygen atom
C which may be replaced₁-C₈Represents an alkylene chain of
You. ), Phenylethyl group, -Q-CO_Two(C₁-C_FourA
Alkyl) group (however, Q represents the same meaning as described above)
Or -NH-Q-CO_Two(C₁-C_FourAlkyl) group (however,
And Q has the same meaning as described above. ), R3
Is -O-R11 (R11 is C_Three-C₈Cycloalkenyl
Group, C_Three-C₈Cycloalkenyl (C₁-C_Four) Alkyl
Group, cyano (C_Two-C₆) Alkyl group, cyano (pheny
Ru) methyl group, indanyl group, (C₁-C_FourAlkoxy)
_Two(C₁-C_Four) Alkyl group, C₁-C_FourAlkoxy (C₁−
C_Four) Alkoxy (C₁-C_Four) Alkyl group, C₁-C_FourC
Lower alkoxy (C₁-C_Four) Alkyl group, C₁-C_FourArco
Kishi (C₁-C_Four) Haloalkyl group, C₁-C_FourHalo alco
Kishi (C₁-C_Four) Alkoxy (C₁-C_Four) Alkyl groups,
C_Two-C₆Alkenyloxy (C₁-C_Four) Alkyl group, C
_Two-C₆Alkynyloxy (C₁-C_Four) Alkyl group, C₁
-C_FourAlkylthio (C₁-C_Four) Alkyl group, keto (C_Three
-C₈) Cycloalkyl group, C₁-C_FourAcyl (C₁−
C_Four) Alkyl group, C₁-C_FourAlkylsulfonyl (C₁−
C_Four) Alkyl group, (C₁-C_FourAlkoxycarbonyl)_Two
Methyl group, pyridyl (C₁-C_Four) Alkyl groups, 5-tri
A fluoromethyl-3-chloro-2-pyridyl group, (substituted
Optionally substituted phenyl (SP3) group) carbonyl
Group, (optionally substituted phenyl (SP1) group and
Is a halogen atom, C₁-C_FourHaloalkyl group, C₁−
C_FourAlkyl group, C₁-C_FourAlkoxy group, C₁-C_FourC
Lower alkoxy group, methanesulfonyl group, C₁-C_FourAl
Coxycarbonyl group, nitro group, hydroxyl group, amine
, A cyano group, -O-CH (CH_Three) CO_Two(C₁-C
_FourAlkyl) group or -O-CH_TwoCO_Two(C₁-C_FourAl
A phenyl group which may be substituted by
), (Optionally substituted phenyl (SP1)
Group) oxy (C₁-C_Four) Alkyl groups, (substituted
The phenyl (SP1) group has the same meaning as described above.
You. ), (Optionally substituted phenyl (SP1)
Group) -Q- (C₁-C_Four) Alkyl groups, (Q and substituted
The optionally substituted phenyl (SP1) group has the same meaning as described above.
Represents taste. ), Het group (Het group means one oxygen atom
Or saturated or unsaturated, characterized by containing two
Represents a 3- to 6-membered heterocycle containing a bond. ) Or-
Q-Het group (Q and Het groups have the same meaning as described above.)
Express. ). ), -NH-R11 (R11 is
Represents the same meaning as ), -S-R11 (R11 is
Represents the same meaning as above. ), C_Three-C₈Alkenylo
Xycarbonyl (C₁-C_Four) Alkyl group, C_Three-C₈Al
Quinyloxycarbonyl (C₁-C_Four) Alkyl group, -N
HCO- (C₁-C_Four) Alkyloxycarbonyl (C₁
-C_Four) Alkyl group, —N (R15) CO— (C₁−
C_Four) Alkyloxycarbonyl (C₁-C_Four) Alkyl
Group (R15 is C₁-C₆Alkyl group, C_Three-C₈Alkene
Group, C_Three-C₈Alkynyl group, C₁-C_FourHaloalkyl
Group, C_Three-C₈Haloalkenyl group, C_Three-C₈Halo alkini
Group, C₁-C₆Acyl group, formyl group, cyano (C₁−
C_Four) Alkyl group, C₁-C_FourAlkoxy (C₁-C_Four)
Alkyl group, C₁-C_FourAn alkoxycarbonyl group or
—C (＝ O) (optionally substituted phenyl (SP
3) group) group (provided that phenyl (S
The group P3) has the same meaning as described above. ) And R
4 is a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group,
No group, C₁-C_FourAlkyl group, C₁-C_FourAn alkoxy group or
Represents a mercapto group, and R3 and R4 represent oxygen, nitrogen, sulfur
Yellow, saturated or characterized by optionally containing carbon atoms
May form a 5- or 6-membered ring having an unsaturated bond.
R2 and R3 are the same as those shown in equations (a) to (f).
May form a ring,

[0007]

Embedded image

Note that Rf, R in equations (a) to (f)
g, A, X, Y, Z, R1, R4 and R5 represent the same meanings as defined above, R17 is a hydrogen atom, a hydroxyl group, an amino group, C ₁ -C ₆ alkyl, C ₃ -C ₈ alkenyl group, C
₃ -C ₈ alkynyl group, C ₁ -C ₄ haloalkyl groups, C ₃ -
C ₈ haloalkenyl group, C ₃ -C ₈ haloalkynyl group, C
₁ -C ₆ acyl group, a formyl group, a benzoyl groups, C ₁ -C
₆ alkoxy group, C ₂ -C ₈ alkenyloxy group, C ₂ -C
₈ alkynyloxy group, C ₁ -C ₆ haloalkoxy group, C
₁ -C ₄ alkoxy (C ₁ -C ₄₎ alkoxy group, CH ₂
CONH ₂ , CH (CO _2- (C ₁ -C ₄ alkyl))
₂ group, CH ₂ - (pyridyl) groups, C ₁ -C ₆ haloalkylcarbonyl group, phenacyl group, C ₃ -C ₈ cycloalkyl (C ₁ -C ₄₎ alkyl group, C ₁ -C ₄ alkoxy (C ₁
—C ₄ ) alkyl group, —Q—CO ₂ (C ₁ -C ₄ ) alkyl group (however, Q represents the same meaning as described above).
CN group (where Q represents the same meaning as described above) or -Q- (phenyl which may be substituted (SP3)
(Wherein Q and the optionally substituted phenyl (SP3) group represent the same meaning as described above), and R28 and R29 each independently represent a hydrogen atom,
A cyano group, a halogen atom, C ₁ -C ₆ alkyl, C ₂ -
C ₈ alkenyl group, C ₂ -C ₈ alkynyl group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄ acyl group, C ₁ -C ₄ alkoxy (C ₁ -C ₄₎ alkoxy group, C ₁ -C ₄ Alkoxy group, C
₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkoxy (C ₁ -C ₄₎ alkyl group, C ₁ -C ₄ alkylthio group or an optionally substituted phenyl (SP3) group (which may be substituted The phenyl (SP3) group has the same meaning as described above, provided that R28 and R28 in the formula (a)
29 is a hydrogen atom and R28 and R in the formula (b)
R28 except when all of 29 and R30 are hydrogen atoms.
When R29 is may represent an oxygen atom together, R30 represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₄
Haloacyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl group, C ₁ -C ₆ acyl group,
Represents a C ₁ -C ₄ alkoxycarbonyl group or a C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl group, provided that when these compounds have optical isomers, diastereomers, and geometric isomers, Includes both the respective compounds and the isolated isomers. And a herbicide containing them as an active ingredient.

[0009]

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION In the formula (I), Rf is CF ₃ ,
Examples include CF ₂ Cl, CF ₂ H, CFClH, CF ₃ CF ₂ , or CF ₂ ClCF ₂ , and preferably CF ₃ .

Rg is H, F, Cl, Br, C≡
N, CO ₂ Me, CH ₂ CH = CH ₂ , CH ₂ C≡CH, M
e, Et, Pr, iso-Pr or Bu;
Preferably, H or F is used.

Z represents an oxygen atom, a sulfur atom, NH, N
Me, NEt, NPr, NBu, N-tert-Bu,
NCO ₂ Me, NCO ₂ Et, NCH ₂ CO ₂ Me, NCH
₂ CO ₂ Et, NPh, N- (4-Cl-Pheny
l), N- (3-Cl-Phenyl), N- (2-C
l-Phenyl), NNHMe, NNHEt, NNH
Pr, NNHBu, NNH-tert-Bu, NNH-
(4-Cl-Phenyl), NNH ₂ , NNH- (3
-Cl-Phenyl), NNH- (2-Cl-Phe)
nyl), NNHCH ₂ CO ₂ Me, NNHCH ₂ CO ₂ E
t, NNHPh, NNHCO ₂ Me or NNHCO ₂ E
t, and preferably an oxygen atom.

A is CH or N, preferably N.

X = Y, N = N, CH = N, N = C
H, C (Cl) = N, N = C (Cl), C (Br) =
N, N = C (Br), CH = CH, C (Cl) = CH,
CH = C (Cl), C (Br) = CH, CH = C (B
r), C (Me) = CH, CH = C (Me), N = C
(Me), N = C (Ph), C (Me) = N, C (P
h) = N, C (Et) = CH, CH = C (Et), C
(Pr) = CH, CH = C (Pr), CH ₂ CH ₂ , CH
₂ CH (Me), CH (Me) CH ₂ , CH ₂ CH (E
t), CH (Et) CH ₂ , CH ₂ CH (Pr), CH
(Pr) CH ₂ , CH ₂ CH ₂ CH ₂ , CH = CHCH ₂ ,
CH ₂ CH = CH, CH ₂ C (＝ O) NH, CH ₂ CH ₂ S
O ₂ , C (＝ O) C (O ＝ O), CH ₂ C (＝ O), (C
= O) NH, (C = S) NH, NHC (= O), NHC
(= S), C (= O) CH = N, C (= O) CH = C
H, CH = CHC (= O), N = CHC (= O), CH
₂ C (= O) NH, C (= O) NHC (= O), C (=
O) N (Me) C (= O), CH = NC (= O), CH
₂ O, C (= O) O, OC (= O), SC (= O) or C (= O) S, preferably CH = N, N =
CH, CH = CH, CH ₂ CH ₂ , C (CH ₃ ) = CH,
_{C (C 2 H 5) =} CH, CH = C (CH 3), CH = C
(C ₂ H ₅ ), CH (CH ₃ ) CH ₂ , CH (C ₂ H ₅ ) CH
₂ , CH ₂ CH (CH ₃ ), CH ₂ CH (C ₂ H ₅ ), C (C
_{H 2 CH 2 CH 3) =} CH or _{CH = C (CH 2 CH 2} ,
CH ₃ ), and more preferably CH ＝ CH.

R1 is H, Cl, F, Br or I, preferably H, Cl or F.

R5 is H, Cl, F or Br, and preferably H.

R2 is H, Cl, F, Br, I, C
N, CSNH_Two, CONH_Two, C≡CH, C≡CSiMe
_Three, CH = CH_Two, Me, Et, Pr, iso-Pr, O
-Me, O-Et, SO_TwoNH_Two, OCH_TwoCO_TwoMe, O
CH_TwoCO_TwoEt, OCH_TwoCH_TwoCO_TwoEt, CF_Three, CF
_TwoCF_Three, CF_TwoCl, CF_TwoH, CF_ThreeO, NO_Two, HCF
_TwoO, ClCH_Two, BrCH_Two, SMe, SO_TwoMe, O
H, SH, NH_Two, CHO, CO_TwoH, CO_TwoMe, CO_Two
Et, CH_TwoCN, NHMe, NMe_Two, OCH_TwoOM
e, OCH_TwoPh, OCH_Two(4-Cl-pheny
l), OCH_Two(4-Br-phenyl), OCH
_Two(4-Me-phenyl), OCH_Two(4-Cl-2
-(OCH (Me) CO_TwoMe) -phenyl), O
CH_Two(4-Me-2- (OCH (Me) CO_TwoMe)-
phenyl), OCH_Two(4-Cl-2- (OCH
(Me) CO_TwoEt) -phenyl), OCH _Two(4-
Me-2- (OCH (Me) CO_TwoEt) -pheny
l), OCH_Two(4-Et-2- (OCH (Me) CO_Two
Me) -phenyl), OCH_Two(4-Et-2-
(OCH (Me) CO_TwoEt) -phenyl), OC
H_Two(4-Pr-2- (OCH (Me) CO_TwoMe) -p
henyl), OCH_Two(4-Pr-2- (OCH (M
e) CO_TwoEt) -phenyl), C≡CPh, CH
= CHCO_TwoEt, NHCH_TwoPh, NHCH_Two(4-C
l-phenyl), NHCH_Two(4-Br-phen
yl), NHCH_Two(4-Me-phenyl), NH
CH_Two(4-Cl-2- (OCH (Me) CO_TwoMe)-
phenyl), NHCH_Two(4-Me-2- (OCH
(Me) CO_TwoMe) -phenyl), SCH_TwoPh,
SCH_Two(4-Cl-phenyl), SCH_Two(4-B
r-phenyl), SCH_Two(4-Me-pheny
l), SCH_Two(4-Cl-2- (OCH (Me) CO_Two
Me) -phenyl), SCH_Two(4-Me-2-
(OCH (Me) CO _TwoMe) -phenyl), OC
H (Me) CO_TwoMe, OCH (Me) CO_TwoEt, NH
CH_TwoCO_TwoMe, NHCH_TwoCO_TwoEt, SCH_TwoCO_TwoM
e or SCH _TwoCO_TwoEt, and preferably F,
Cl, Br, I, CN, NO_TwoOr CSNH_TwoBut
It is.

R3 is OCH_TwoSMe, O- (t
Etrahydrofuran-3-yl), O-
(2,3-epoxypropyl), O- (3-Cl
-5-CF_Three-2-pyridyl), OCH_TwoOCH_Two
Ph, O- (tetrahydrofuran-2-y
l), OCH_TwoOCH_TwoCH_TwoOMe, OC (= O) (4
-MeO-Phenyl), OC (= O) (4-FP)
henyl), OCH_Two-(Tetrahydrofu
ran-2-yl), OCH_Two− (2,2-dimet
hyl-1,3-dioxolane-4-yl), O
CH (CH_TwoOEt)_Two, -OCH_Two− (Tetrahy
dropyran-2-yl), OCH (CO_TwoE
t)_Two, OCH_Two-(2-furyl), OCH_TwoCH_TwoO
CH = CH_Two, OCH_TwoCH_TwoSMe, O- (2-cyc
lohexen-1-yl), OCH_TwoCH_TwoOCH_TwoC
H_TwoCl, OCH_TwoCH_TwoOCH_TwoCH = CH_Two, OCH_TwoC
H_TwoOPh, OCH_TwoCH_TwoO- (2-Cl-pheny)
l), OCH_TwoCH_TwoOCH_TwoCH_TwoOMe, OCH_TwoCH_Two
OCH_TwoCH_TwoOCH_TwoCH_TwoCl, OCH_TwoCH (Me)
OPh, OCH (Me) CH_TwoOPh, OCH_Two− (Te
trahydrofuran-3-yl), OCH_TwoC
H_TwoCH_TwoSMe, OCH_TwoCH_TwoOCH_TwoCH_TwoOEt, O
-(Indan-2-yl), O- (indan-1-
yl), O- (tetrahydropyran-4-
yl), OCH (CH_TwoCl) CH_TwoOMe, OCH _Two−
(2H, 3H-benzo [e] 1,4-dioxin
-2-yl), OCH_TwoCOMe, OCH_TwoCOEt, O
CH_TwoCOPr, OCH_Two-(2-pyridyl), O
CH_Two-(3-pyridyl), OCH_Two-(3-me
Tyloxetan-3-yl), OCH (Ph) C
≡N, OCH (Me) C≡N, OCH (Et) C≡N,
OCH_Two-(Cyclohex-3-enyl), OC
H (Pr) C≡N, OCH (Me) COMe, OCH
(Et) COMe, OCH (Pr) COMe, OCH_Two
CH_TwoSO_TwoMe, OCH (Me) COEt, OCH (M
e) COPr, O- (cyclohexan-1-on)
e-2-yl), N (COCF_Three) CH_TwoC≡CH, N
(COPh) CH_TwoC≡CH, NHCOCH_TwoOC (=
O) Me, N (COCH_TwoOC (= O) Me) CH_TwoC≡
CH, CO_TwoC (Me)_TwoCO_TwoCH_TwoCH = CH_TwoOr
C (= O) NHCH (Me) Ph is mentioned.

R4 is H, F, Cl, Me, Et,
Pr, iso-Pr, MeO, EtO, PrO, N
O ₂ , NH ₂ , NHCO-tert-Bu, CH ₂ C (M
e) = CH ₂ , CH ₂ CH = CH ₂ , CH ₂ C≡CH, 2
Examples include 3-epoxy-2-methylpropyl or 2,3-epoxypropyl, preferably H or F. Incidentally, when the R4 is 2,3-epoxy-2-methylpropyl or _{CH 2 C (Me) = CH} 2, as the R3 include a substituted group attached to the phenyl group with an oxygen atom.

R2 and R3 may form a ring.
In the case, -R2 to R3- are -OC (R28) (R29) C
(= O) N (R17)-, -OC (= O) N (R17)
-, -N = C (R28) C (= O) N (R17)-,-
OC (R28) (R29) SO _TwoN (R17)-, -O
C (R28) (R29) C (= NCH = C (R17)
-)-N-, -SC (= O) N (R17)-or -N
(R30) C (R28) (R29) C (= O) N (R1
7)-. Preferably, -OC (R28)
(R29) C (= O) N (R17)-.

R17 includes the following substituents.
You. Me, Et, Pr, iso-Pr, Bu, sec-
Bu, iso-Bu, H, NH_Two, OH, CH_TwoCONH
_Two, CH_Twocyclo-Pr, CH_TwoCO_TwoMe, CH_TwoC
O_TwoEt, COMe, COEt, COPr, CO-is
o-Pr, COBu, CO-tert-Bu, CO-c
Cyclo-Pr, COCF_Three, CH (Me) CO_TwoMe,
CH (Me) CO_TwoEt, CH_TwoPh, CH_Two− (2-C
l-Phenyl), CH_Two-(3-Cl-Pheny
l), CH_Two-(4-Cl-Phenyl), CH_Two−
(2-pyridyl), CH_Two-(3-pyridy
l), CH_Two-(4-pyridyl), CH (CO_TwoE
t)_Two, CH (CO_TwoMe)_Two, OPr, O-iso-P
r, OBu, O-tert-Bu, OCH_TwoCH = C
H_Two, OCH (Me) CH = CH_Two, OC (Me)_TwoCH
= CH_Two, OCH_TwoC≡CH, OCH (Me) C≡CH,
OC (Me)_TwoC≡CH, OCH_TwoCH_TwoCH_TwoF, OCH
_TwoCH_TwoF, OCH_TwoCH_TwoCF_Three, OCH_TwoCH_TwoCH_TwoC
1, OCH (CH_TwoF)_Two, OCH_TwoOMe, OCH_TwoOE
t, OCH_TwoCH_TwoOMe, OCH_TwoCH_TwoOEt, OCH
_TwoCH_TwoOCH_TwoCH_TwoOMe, CH_TwoCH = CH_Two, CH_Two
C≡CH, CH_TwoC≡N, CH_TwoCH_TwoF, CH_TwoCH_TwoC
l, CH_TwoCH_TwoCH_TwoF, CH_TwoOMe, OMe, OE
t, CH_TwoOEt, CH _TwoCH_TwoCH_TwoCl, CH_TwoCH_TwoC
H_TwoCH_TwoF, CH_TwoCCl = CH_Two, CH_TwoCBr = C
H_Two, CH (Me) C≡CH, CH (Me) CH = CH_Two
Or CH (Me) C≡N.

R28 and R29 each independently include the following substituents. H, C≡N, F, C
1, Br, I, Me, Et, Pr, iso-Pr, B
u, sec-Bu, iso-Bu, tert-Bu, C
H = CH ₂ , CH ₂ CH = CH ₂ , CH (Me) CH = C
H ₂ , C (Me) ₂ CH = CH ₂ , CH (Et) CH = C
H ₂ , C≡CH, CH ₂ C≡CH, CH (Me) C≡C
H, C (Me) ₂ C≡CH, CH (Et) C≡CH, C
H (Pr) C≡CH, CF ₃ , CF ₂ Cl, CH ₂ Cl,
CH ₂ F, CHF ₂ , CH ₂ CF ₃ , CH ₂ CH ₂ CH ₂ F,
CH ₂ CH ₂ F, CHCl ₂ , CH ₂ CH ₂ Cl, CH ₂ CH
₂ CH ₂ Cl, COMe, COEt, COPr, CO-t
ert-Bu, OMe, OEt, OPr, O-iso-
Pr, OBu, O-iso-Bu, O-sec-Bu,
O-tert-Bu, CO ₂ Me, CO ₂ Et, CO ₂ P
_{r, CO 2 -iso-Pr,} CO 2 -tert-Bu, C
H ₂ OMe, CH ₂ CH ₂ OMe, CH ₂ CH ₂ OEt, O
CH ₂ OMe, OCH ₂ CH ₂ OMe, CH ₂ SMe, P
h, 2-Cl-Ph, 3-Cl-Ph, 4-Cl-P
h, 2-F-Ph, 3-F-Ph, 4-F-Ph or 4-Me-Ph.

When R28 and R29 are taken together, an oxygen atom is exemplified.

As R30, H, Me, Et, Pr, C
H ₂ CH = CH ₂ , CH ₂ C≡CH, CH (Me) C≡C
H, COMe, COEt, COPr, CO-tert-
Bu, CO ₂ Me, CO ₂ Et, CH ₂ OMe, CH ₂ OE
t, CH ₂ CH ₂ OMe or CH ₂ CH ₂ OEt.

[0025] R3 and R4 may be the wound ring, in which case, = The -R4~R3- -CH CH-CH ₂ -
O -, - CH = CH- O -, - CH 2 CH 2 O -, - O-
CH = CH -, - O- CH 2 CH 2 -, - CH = C (M
e) -O -, - O- C (Me) = CH -, - O-CH 2
C (= O) N (CH ₂ C≡CH)-, -OCH ₂ C (=
_{O) NH -, - CH 2} SO 2 NH -, - CH 2 SO 2 N (C
_{OMe) -, - CH 2 SO} 2 N (CH 2 C≡CH) -, -
O (C = O) N (CH ₂ C≡CH)-, -SC (M
e) = N-, -OC (Me) = N-, -S-CH = N
-, -O-CH = N- or -OC (Me) _2- O-
Is mentioned.

The symbols in the text have the following meanings. _{Me: CH 3 Et: CH 2} CH 3 Pr: CH 2 CH 2 CH 3 iso-Pr: CH (CH 3) 2 cyclo-Pr: CH (CH 2) 2 Bu: CH 2 CH 2 CH 2 CH 3 sec- _{Bu: CH (CH 3) C} 2 H 5 iso-Bu: CH 2 CH (CH 3) 2 tert-Bu: C (CH 3) 3 cyclo-Bu: CH (CH 2) 3 Pn: CH 2 CH 2 CH ₂ CH ₂ CH ₃ cyclo-Pn: CH (CH ₂ ) ₄ iso-Pn: CH ₂ CH ₂ CH (CH ₃ ) ₂ neo-Pn; CH ₂ C (CH ₃ ) ₃ cyclo-Hex: CH (CH ₂ ) ₅ tert-Pn: C (CH ₃ ) ₂ C ₂ H ₅ Hex: (CH ₂ ) ₅ CH ₃ Hep: (CH ₂ ) ₆ CH ₃ Oct: (CH ₂ ) ₇ CH ₃ Ph, Phenyl: C ₆ H ₅ 4-Cl-Ph: 4-Cl-Phenyl With the compound of the present invention As a herbicide for field and non-cultivated land, it can be used in any of soil treatment and foliage treatment methods, such as Solanum nigrum , Datura stramonium, etc.
naceae) weeds, Malvaceae weeds represented by scabs ( Abutilon theophrasti ), American sika deer ( Sida spinosa ), etc., and Malva asagao ( Ipomoea purpur)
ea ) and morning glory ( Ipomoea spps.) and convolvulus ( Ca
Convolvu (Convolvu) represented by lystegia spps.
laceae), Amaranthaceae weeds represented by Amaranthus lividus , Amaranthus retroflexus, etc., and Xanthium pensylvan
icum ), ragweed ( Ambrosia artemisiaefolia ), sunflowers ( Helianthus annuus) , and cornflowers ( Galinsoga )
ciliata) , Atlantic thistle ( Cirsium arvense) , Noborogiku ( Senecio vulgaris ), Himejon ( Erigeron )
annus) Asteraceae represented by such (Compositae) weeds, field cress (Rorippa indica), Noharagarashi (Sinapis
arvensis), shepherd's purse (Capsella Bursapastoris) Brassicaceae represented by such (Cruciferae) weeds, knotweed (Po
lygonum Blumei , buckwheat ( Polygonum convolvulu )
s) and the like, Polygonaceae weeds such as Portulaca oleracea , and Portulacaceae weeds such as Portulaca oleracea and Chenopodium albu
m) , Chenopodium fi cifolium , Kochia scoparia, etc.
iaceae) weeds, Caryophyllaceae weeds such as Stellaria media, Scrophulariaceae weeds such as Veronica persica, etc., Commelina comm
Laminaceae (Commelinaceae) weeds, such as unis ), Labiadenaceae ( Lamium amplexicaule) , and Labiatae (Labi), such as Lamium purpureum
atae) weed, Euphorbia supina , Euphorbia maculata and other Euphorbiaceae weeds, and Galium ( Galium )
spurium ), Rubiaceae weeds such as Rubia akane, Violaceae weeds such as violet ( Viola mandshurica) , Sesbania exaltata , and Cassia o.
btusifolia) legume that typified by (Leguminosae) broad-leaved weeds such as weeds (Broad-leaved weeds), wild sorghum (Sorgham bicolor), fall panicum (Panicum dichotom
iflorum) , Johnsongrass ( Sorghum halepense) , Barnyardgrass ( Echinochloa crus-galli var. crus-galli ),
Echinochloa crus-galli var. Praticol
a), cultivation Bie (Echinochloa utilis), crabgrass (Digi
taria adscendens ), oats ( Avenafatua ), hawksbill ( Eleusine indica) , enokorogosa ( Setaria viri )
dis) , various weeds (Croplandous weeds) such as Graminaceous weeds such as sparrows ( Alopecurus aegualis) and Cyperaceous weeds such as Cyperus rotundus and Cyperus esculentus. It has high herbicidal activity at low dose.

In addition, as a herbicide for paddy fields, soil treatment under flooding
And foliage treatment,
Modaka (Alisma canaliculatum), Omodaka (Sagittar
ia trifolia), Urikawa (Sagittaria pygmaea)
Represented Omodacae (Alismataceae) weed, Tamakayatsu
Li (Cyperus difformis),Cyperus sero
tinus), Firefly (Scirpus juncoides), Krogwai
(Eleocharis kuroguwai)Cyperus represented by etc.
Family (Cyperaceae) weed, Azena (Lindernia pyxidari
a)Scrothulariacea (Scrothulariacea)
e) Weeds, conger (Monochoria vaginalis)Etc.
Weed, Potenderiaceae Weed, Hirumushiro
(Potamogeton distinctus) Etc.
Family (Potamogetonaceae) weedsRotala ind
ica)(Lythraceae) weeds, such as
Dog millet ((Echinochloa oryzicola), Himetamebie
(Echinochloa crus-galli var.formosensis), Inubi
D (Echinochloa crus-galli var. crus-galli)weed
Various kinds of paddy weeds, low herbicide and high weed killing
Have power.

Some of the compounds of the present invention are important crops such as rice, wheat, barley, sorghum, peanuts,
Highly safe against corn, soybeans, cotton, beets, etc.

The compounds of the present invention can be prepared, for example, from Schemes 1 to 15
(Scheme 1)
To 15, Z, A, Ra, Rc, Rf, Rg and R1
~R5 represents the same meaning as defined above, R 'and R "each independently represent a C ₁ -C ₄ alkyl group, Hal represents a halogen atom, n represents an integer of 2 or 3.)

[0030]

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[0031]

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[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[0038]

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[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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(Scheme 1) The aminocrotonate derivative (II) and the phenylisothiocyanate derivative (III) are reacted in an inert solvent in the presence of a base,
A 2-mercaptopyrimidine derivative (IV) can be obtained.

Compound (II) is prepared according to Org. Che
m. , 21 , 1358-61 (1956); Het
erocycl. Chem. , 513 (1972); Z
hur. Org. Kim. , 22 (8), 1603-9
(1986); can be synthesized with reference to JP-A-5-140060 and the like. Compound (III) can be obtained from the corresponding aniline derivative by Sandler, S .; R. , Karo, W.C.
“Organic Functional Group
Preparations "Academic, Ne
w York, 1968, Vol. 1, pp312-3
It can be prepared according to the method described in No. 15.

Compound (IV) is converted to an alkylating agent such as dimethyl sulfate or methyl iodide (for alkyl as M
e, Et, etc.) in the presence of a base to synthesize, for example, a 2-methylmercaptopyrimidine derivative (V). Compound (V) can be derived to 2-methanesulfonylpyrimidine derivative (VI) using, for example, an oxidizing agent such as hydrogen peroxide, air, and metachloroperbenzoic acid. The compound (VI) is reacted with sodium azide (which may be potassium azide or trimethylsilyl azide) to give the compound of the present invention (I: X to Y → N
= N, A = N, Z = O).

The compound (VI) can be reacted with ammonia or ammonium acetate to lead to a 2-aminopyrimidine derivative (VII), or can be reacted with hydrazine to lead to a 2-hydrazinopyrimidine derivative (VIII).

However, by increasing the reaction conditions, compound (VII), (VIII) or (I: X to Y → N =
N, A = N, Z = O) can also be synthesized. (Scheme 2) Compound (VIII) is converted to, for example, “Com
prehensive Heterocyclic C
hemistry "Vol.5, Part4A, 890
The compound of the present invention (I: XY → C (Ra)) is reacted with an orthoester derivative with reference to the method described in
= N, A = N, Z = O).

Compound (VII) was prepared according to the method described in Chem, Pham.
Bull. 40 (1) With reference to 235-237 (1992) and the like, a halogenoacetaldehyde dialkyl acetal derivative (a chlorine atom and a bromine atom are preferable as a halogen atom) to react with the compound of the present invention (I: X to Y → CH)
= CRa, A = N, Z = O) or the compound of the present invention (I: XY → C (Ra) = CH, A = N, Z
= O) can be synthesized. (Scheme 3) Derivation of pseudothiourea (IX) and formylaniline derivative (X) to guanidine derivative (XI). Further, compound (XI) was converted to β-keto acid ester derivative (XII) and Helvetica Chimica.
Acta, Vol. 59, Fasc. 4 (1976) p
The compound of the present invention (I: XY → CH ₂ CH ₂ , A = N, Rg =
H, Z = O) can be obtained.

1,2,4- having a methyl mercapto group
Triazole (XIII) and imidazole (XV)
Compounds (XIV) and (XVI) can be synthesized by reacting with formylaniline derivative (X), respectively. Subsequently, these and β-ketoester derivative (XII)
Are reacted to obtain a compound of the present invention (I: X to Y → N = CRa, A = N, Rg = H, Z = O
And the compound of the present invention (I: XY → C (Ra))
= CHand / orCH = CRa, A = N, Rg = H,
Z = O) can be synthesized. In some cases, the MeS group of (XIII) or (XV) is oxidized to
It can also be subjected to the reaction as an SO ₂ group. (Scheme 4) Compound (I: Z = O, A = N, Rg ≠ C
N) with phosphorus pentasulfide (P ₂ S ₅ ) or Lawesson's Reagent: 2,4-
bis (4-methoxyphenyl) -1,3-
dithia-2,4-diphosphetane-
The compound of the present invention (I: Z = S, A = N, R
g ≠ CN) can be synthesized. (Scheme 5) Compound (XVII) prepared from compound (VI) and aziridine can be prepared, for example, according to the method described in J. Am. Org. Che
m. , Vol. 39, no. 24, 3508 (197
4) and the like, and reacted in the presence of sodium iodide or potassium iodide.
Y → CH ₂ CH ₂ , A = N, Z = O) can be synthesized. Subsequently a suitable oxidizing agent, for example air, NaOCl,
DDQ, potassium permanganate or chloranil (c
hloranil) and the like, and the compound of the present invention (I: X to
Y → CH = CH, A = N, Z = O). (Scheme 6) YAKUGAKU ZASSHI, 94
(12) The compound (VI) and the compound (XVIII) obtained from the amino alcohol are reacted with thionyl chloride or phosphorus oxychloride with reference to the method described in pp1503-1514 (1974) to give the compound (XI
X). For example, DBU, pyridine, KOH,
Base with the invention compounds are reacted, such as sodium methoxide _{(I: X~Y → CH 2 CH} 2 orCH 2 CH 2 CH 2, A
= N, Z = O, n = 2 or 3) can be obtained.

If the amino alcohol used in this reaction has a substituent such as methyl or phenyl at the carbon atom, a substituent corresponding to the methylene moiety of X to Y of the compound of the present invention can be introduced. (Scheme 7) Compound (VII) is reacted with a halogenopropylaldehyde dialkyl acetal (halogen is preferably chlorine or bromine), and then treated with a base to give the compound of the present invention (I: XY → CH ₂ CHＣＨCH, A = N, Z = O) or the compound of the present invention (I: X to Y → CH =
CHCH ₂ , A = N, Z = O) can be synthesized. (Scheme 8) Compound (V) is combined with an aminoacetaldehyde dialkyl acetal derivative, for example, as described in J. Am. Hete
rocyclic Chem. , 26 , 205-207
(1989), and a 2,2-dialkoxyethylamino group is introduced into the 2-position to synthesize compound (XX). Further, compound (XX) is prepared under acidic conditions, for example,
In the presence of concentrated sulfuric acid, methanesulfonic acid, polyphosphoric acid, concentrated hydrochloric acid, paratoluenesulfonic acid, etc., the compound of the present invention (in the case of I: XY → CH = CH, A = N, Z = O) is subjected to a ring-closure reaction. Can be synthesized. (Scheme 9) The compound of the present invention (I: Z = O) is reacted with phosphorus oxychloride and then with NH ₂ —Rc with reference to, for example, EP 168262, etc.
NRc) can be synthesized. (Scheme 10) Compound (VII) is converted to isocyanate R'NCO (R 'is preferably potassium, sodium or ammonium) or alkyl isocyanate R'NCO (R' is methyl, ethyl, propyl, etc.) Urea derivative (XXI) can be synthesized. Compound (XXI)
Is reacted with dimethylformamide dimethyl acetal, and the compound of the present invention (I: XY → CH ＝ NC (（O),
A = N, Z = O) can be synthesized.

The compound (XXI) is reacted with a phosgene derivative such as phosgene, phosgene dimer, triphosgene or a chloroformate to give a compound of the present invention (I: XY → C (＝ O) N (R ′) C ( = O), A =
N, Z = O) can be synthesized.

The compound (VII) is reacted with a 3,3-dialkoxypropionic acid derivative to give the compound of the present invention (I: X
~ Y → C (= O) CH = CH, A = N, Z = O)
Can be synthesized.

Compound (VII) and chlorocarbonyl isocyanate can be prepared, for example, according to the method described in Bull. Chem. S
oc. Jpn. , 61 , 2217-2219 (198
8), the compound of the present invention (I: XY → C (（O) NHC (＝ O),
A = N, Z = O) can be synthesized.

Compound (VII) is reacted with acetic anhydride or acetyl chloride to give an acetamide derivative (XX).
II). Compound (XXII) is converted to D
The compound of the present invention (I: XY → CH ＝ CHC (＝ O), A = N, Z ＝ O
) Can be synthesized. (Scheme 11) Compound (VII) is reacted with chloroacetic acid chloride or bromoacetic acid chloride, and the compound of the present invention (I: XY → CH ₂ C (＝ O), A = N, Z =
O) can be synthesized.

The compound (VII) is reacted with oxalyl chloride to give the compound of the present invention (I: XY → C (＝ O) C
(= O), A = N, Z = O) can be synthesized.

Compound (VII) and ethenesulfonyl fluoride or chloroethylsulfonyl chloride can be prepared, for example, according to the method described in J. Am. Org. Chem. , Vol. 4
4, No. 22, 3847-3858 (1979) and the like, whereby the compound of the present invention (I: X to Y → CH ₂ CH ₂ SO ₂ , where A = N, Z = O) can be synthesized. it can. (Scheme 12) Compound (VIII) is reacted with chloroacetic acid chloride or bromoacetic acid chloride, and the compound of the present invention (I: XY → CH ₂ C (＝ O) NH, A =
N, Z = O) can be synthesized.

The compound (VIII) is reacted with glyoxylic acid (may be an ester form) or dimethyl acetal glyoxylate to give the compound of the present invention (I: XY → C
(= O) CH = N, A = N, Z = O) can be synthesized.

Compound (VIII) is converted to, for example, phosgene,
By reacting with a phosgene derivative such as phosgene dimer or triphosgene, the compound of the present invention (I: XY → C (＝ O) N
H, A = N, Z = O) can be synthesized. (Scheme 13) The compound (VI) is reacted with hydroxylamine to give a compound (XXIII), which is subsequently reacted with, for example, a phosgene derivative such as phosgene, phosgene dimer, triphosgene or a chloroformate to give the compound of the present invention (I : X to Y → C (=
O) O, A = N, Z = O) can be synthesized. (Scheme 14) Compound (XXIV) and bromoacetaldehyde or chloroacetaldehyde can be prepared, for example, according to the method described in J. Am. Org. Chem. , Vol. 42, no. 1
4,2448-2454 (1977) and the like to give the compound of the present invention (I: X to Y → C
H = CH, A = CH, Z = O) can be synthesized.

The compound (XXIV) is reacted with a halogenating agent such as NBS, NCS, chlorine or bromine in the presence of BPO or AIBN to synthesize a halogenomethyl compound (XXV), which is subsequently reacted with formamide to form a dehydration ring. The compound of the present invention (I: XY → CH
= N, A = CH, Z = O) can be synthesized.

Alternatively, after introducing an amino group into compound (XXV) to obtain compound (XXVI), for example, USP
4,044,015, etc., formylation with formic acid, followed by dehydration with phosphorus oxychloride to give the compound of the present invention (I: XY → CH = N, A = CH, Z = O)
Can be synthesized. (Scheme 15) The compound (XXVII) is reacted with a β-keto acid ester derivative (XII) or a 2,2-ethoxyvinylhaloalkyl ketone (XXVIII),
Compound of the present invention (I: XY → N = CH, A = CH, Z =
O, Rg = H) can be synthesized.

Compound (V) or (V
Although the methylmercapto group and the methanesulfonyl group of I) are respectively used as leaving groups in the next reaction, the reaction may be carried out using a compound containing a chlorine atom as the leaving group.

[0066]

The synthesis examples of the compounds and intermediates of the present invention are specifically described below by way of examples, but the present invention is not limited by these examples. [Example 1] 8- [2,7-difluoro-3,4-dihydro-3-oxo-4- (2-propynyl) -2H-
1,4-benzoxazin-6-yl] -7,8-dihydro-5-trifluoromethylimidazo [1,2-a]
Synthesis of Pyrimidin-7-one (Compound No. 244 of the present invention)

[0067]

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8- [2,7-difluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-
6-yl] -7,8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one 0.6
g, propargyl bromide 1.0 g, potassium carbonate 0.1 g.
A mixture of 6 g and 30 ml of acetonitrile was heated under reflux for 3 hours. The solvent was distilled off under reduced pressure, 200 ml of saturated saline was added, and the mixture was extracted with ethyl acetate. The extract layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by a silica gel preparative thin layer plate (developing solvent: ethyl acetate / hexane = 1/1) to obtain 0.45 g of the desired product as white crystals. ¹ H-NMR (ppm) 2.23 to 2.24 (m, 1
H), 4.61-4.77 (m, 2H), 6.06.
(D, J = 50 Hz, 1H), 6.64 (s, 1H),
7.02 to 7.40 (m, 4H) [CDCl ₃ ] mp 102-104 ° C. [Example 2] 8- [3,4-dihydro-3-oxo-4]
-(2-propynyl) -2,2,7-trifluoro-2
H-1,4-benzoxazin-6-yl] -7,8-
Dihydro-5-trifluoromethylimidazo [1,2-
a] Pyrimidin-7-one (Compound No. 24 of the present invention)
Synthesis of 5)

[0069]

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8- [3,4-dihydro-3-oxo-
0.3 g of 2,2,7-trifluoro-2H-1,4-benzoxazin-6-yl] -7,8-dihydro-5-trifluoromethylimidazo [1,2-a] pyrimidin-7-one A mixture of 0.7 g of propargyl bromide, 0.3 g of potassium carbonate and 10 ml of dimethylformamide was stirred at 130 ° C. for 30 minutes. Mix the mixture with saturated saline 10
Poured into 0 ml and extracted with ethyl acetate. The extract layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by a silica gel preparative thin layer plate (developing solvent: ethyl acetate / hexane = 1/1) to obtain 0.12 g of the desired product as pale yellow crystals. ¹ H-NMR (ppm) 2.39 to 2.42 (m, 1
H), 4.65-4.82 (m, 2H), 6.69.
(S, 1H), 7.03 to 7.51 (m, 4H) [CD
Cl ₃ ] mp 192-194 ° C. Table 1 shows the structural formula and physical properties of the compound of the present invention synthesized according to the above Examples, including the above Examples.

[Table 1]

[0072]

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[0073]

[Table 1] ――――――――――――――――――――――――――――――――― Compound No. R2 R3 R4 ――――― ―――――――――――――――――――――――――――――― 209 Cl OCH ₂ SMe H mp 39- 41 ℃ 210 Cl O- (tetrahydrofuran-3- yl) H mp 133-135 ℃ 211 Cl O- (2,3-epoxypropyl) H mp 126-128 ℃ 212 Cl O- (3-Cl-5-CF ₃ -2-pyridyl) H mp 61-65 ℃ 213 Cl OCH ₂ OCH ₂ Ph H n _D ²⁰ . ⁷ 1.4368

214 Cl O- (tetrahydrofuran-2-yl) H mp 175-179 ° C. 215 Cl OCH ₂ OCH ₂ CH ₂ OMe H n _D ^21.0 1.5263 216 Cl OC (= O)-(4-MeO-phenyl) H mp 70- 73 ℃ 217 Cl OC (= O)-(4-F-phenyl) H mp 75- 78 ℃ 218 Cl OCH _2- (tetrahydrofuran-2-yl) H mp 134-137 ℃ 219 Cl OCH _2- ( 2,2-dimethyl-1,3-dioxolane-4-yl) H mp 45-48 ° C 220 Cl CO ₂ C (Me) ₂ CO ₂ CH ₂ CH = CH ₂ Hmp 129-131 ° C 221 Cl OCH (CH ₂ OEt) ₂ H mp 86-88 ° C 222 Cl OCH _2- (tetrahydropyran2-yl) H mp 167-169 ° C 223 Cl OCH (CO ₂ Et) ₂ H mp 30- 33 ° C 224 Cl OCH _2- (2-furyl ) H mp 170-173 ° C 225 Cl OCH ₂ CH ₂ OCH = CH ₂ H mp 163-166 ° C 226 Cl OCH ₂ CH ₂ SMe H mp 88-90 ° C 227 Cl O- (2-cyclohexen-1-yl) H _{mp 37- 40 ℃ 228 Cl OCH 2} CH 2 OCH 2 CH 2 Cl H mp 105-107 ℃ 229 Cl OCH 2 CH 2 OCH 2 CH = CH 2 H mp 78- 80 ℃ 230 Cl OCH 2 CH 2 OPh H mp 35 -38 ° C ―――――――――――――――――――――――――――――――――――

[0075]

[Table 2] ――――――――――――――――――――――――――――――――― Compound No. R2 R3 R4 ――――― ―――――――――――――――――――――――――――――― 231 Cl OCH ₂ CH ₂ O- (2-Cl-phenyl) H mp 137-139 ℃ 232 Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OMe H mp 98-100 ℃ 233 Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OCH ₂ CH ₂ Cl H mp 67- 70 ℃ 234 Cl OCH ₂ CH (Me) OPh H mp 105-107 ℃ 235 Cl OCH (Me) CH 2 OC 6 H 5 H n D 24.9 1.4918 236 Cl OCH 2 - (tetrahydrofuran-3-yl) H mp 123-125 ℃ 237 Cl OCH 2 CH 2 CH 2 SMe H mp 60-62 ° C 238 Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OEt H mp 98-100 ° C 239 Cl O- (indan-2-yl) H mp 151-153 ° C 240 Cl O- (indan-1-yl) H mp 69-71 ° C 241 Cl NHCOCH ₂ OC (= O) Me H mp 195-198 ° C 242 Cl N (COCH ₂ OC (= O) Me) CH ₂ C≡CH H mp 140-142 ° C 243 OC (= O ) N (CH ₂ C≡CH) H mp 80-82 ° C 244 OC (F) HC (= O) N (CH ₂ C≡CH) H mp 102-104 ° C 245 OCF ₂ C (= O) N (CH ₂ C≡CH) H mp 192-194 ° C 246 Cl O- (tetrahydropyran-4-yl) H mp 180-182 ° C 247 Cl OCH (CH ₂ Cl) CH ₂ OMe H mp 94-96 ℃ 248 Cl OCH _2- (2H, 3H-benzo [e] 1,4-dioxin-2-yl) H mp 63-66 ℃ 249 Cl OCH ₂ COMe H mp 202-205 ℃ 250 Cl OCH (Me) C≡NH mp 182-184 ℃ 251 OCH ₂ C (= O) NH H mp 198-201 ℃ 252 Cl OCH _2- (2-pyridyl) H mp 147-150 ℃ ――――― ――――――――――――――――――――――――――――――

[0076]

[Table 3] ――――――――――――――――――――――――――――――――― Compound No. R2 R3 R4 ――――― ―――――――――――――――――――――――――――――― 253 Cl OCH _2- (3-methyloxetan-3-yl) H mp 156-158 ℃ 254 Cl OCH (Ph) C≡NH mp 80-88 ℃ 255 Cl OCH _2- (cyclohex-3-enyl) H mp 96-99 ℃ 256 Cl OCH (Me) COMe H mp 51-53 ℃ 257 Cl OCH ₂ CH ₂ SO ₂ Me H mp 155-158 ° C 258 OCH (Me) C (= O) NH H mp 123-125 ° C 259 OCH (Me) C (= O) N (CH ₂ C≡CH) H mp 199-202 ° C 260 OC (Me) ₂ C (= O) NH H mp 134-136 ° C 261 OC (Me) ₂ C (= O) N (CH ₂ C≡CH) H mp 201-204 ° C 262 Cl O- (cyclohexan -1-one-2-yl) H mp 84-89 ℃ 263 Cl OCH ₂ CH = CH mp 52-55 ℃ 264 OCH ₂ C (= O) N (CH ₂ C (= O) NH ₂ ) H mp> 280 ° C (dec.) 265 OCH ₂ C (= O) N (CH _2- (2-pyridyl)) H n _D ^22.3 1.5524 266 OCH ₂ C (= O) N (OCH ₂ C≡CH) H mp 84- 86 ℃ 267 OCH ₂ C (= O) N (CH (CO ₂ Et) ₂ ) H mp 58-60 ℃ 268 Cl OC (Me) = CH mp 185-188 ℃ ――――――――――― ――――――――― The compounds of the present invention synthesized according to the above scheme or Examples are shown in Tables 2 and 3 including the compounds synthesized in the Examples. The invention is not limited by these.

[Table 2]

[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]

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[0089]

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[0090]

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[0091]

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[0092]

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[0093]

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[0094]

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[0095]

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[0096]

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[0097]

[Table 4] ――――――――――――――――――――――――――――――――――― R3 ―――――――――― ――――――――――――――――――――――――― OCH_TwoSMe, O- (tetrahydrofuran-3-yl), O- (2,3-epoxypropyl), O- (3-Cl-5-CF_Three-2-pyridyl), OCH_TwoOCH_TwoPh, O- (tetrahydrofuran-2-yl), OCH_TwoOCH_TwoCH_TwoOMe, OC (= O) (4-MeO-Phenyl), OC (= O) (4-F-Phenyl), OCH_Two-(Tetrahyrofuran-2-yl), OCH_Two-(2,2-dimethyl-1,3-dioxolane-4-yl), OCH (CH_TwoOEt)_Two, -OCH_Two-(Tetrahydropyran-2-yl), OCH (CO_TwoEt)_Two, OCH_Two-(2-furyl), OCH_TwoCH_TwoOCH = CH_Two, OCH_TwoCH_TwoSMe, O- (2-cyclohexen-1-yl), OCH_TwoCH_TwoOCH_TwoCH_TwoCl, OCH_TwoCH_TwoOCH_TwoCH = CH_Two, OCH_TwoCH_TwoOPh, OCH_TwoCH_TwoO- (2-Cl-phenyl), OCH_TwoCH_TwoOCH_TwoCH_TwoOMe, OCH_TwoCH_TwoO CH_TwoCH_TwoOCH_TwoCH_TwoCl, OCH_TwoCH (Me) OPh, OCH (Me) CH_TwoOPh, OCH_Two-(Tetrahydrofuran-3-yl), OCH _Two CH_TwoCH_TwoSMe, OCH_TwoCH_TwoOCH_TwoCH_TwoOEt, O- (indan-2-yl), O- (indan-1-yl), O- (tetrahydropyran an-4-yl), OCH (CH_TwoCl) CH_TwoOMe, OCH_Two-(2H, 3H-benzo [e] 1,4-dioxin-2-yl), OCH_TwoCOMe, O CH_TwoCOEt, OCH_TwoCOPr, OCH_Two-(2-pyridyl), OCH_Two -(3-pyridyl), OCH_Two-(3-methyloxetane-3-yl), OCH (Ph) C≡N, OCH (Me) C≡N, OCH (Et) C≡N, OCH_Two− (Cyclohex-3-enyl), OCH (Pr) C≡N, OCH (Me) COMe, OCH (Et) COMe, ―――――――――――――――――――― ―――――――――――――――

[0098]

[Table 5] ――――――――――――――――――――――――――――――――― R3 ―――――――――― ――――――――――――――――――――――――― OCH (Pr) COMe, OCH ₂ CH ₂ SO ₂ Me, OCH (Me) COEt, OCH (Me) COPr , O- (cyclohexan-1-one-2-yl), N (COCF ₃ ) CH ₂ C≡CH, N (COPh) CH ₂ C≡CH, NHCO CH ₂ OC (＝ O) Me, N (COCH ₂₎ OC (= O) Me) CH 2 C≡CH, C O 2 C (Me) 2 CO 2 CH 2 CH = CH 2 or C (= O) NHCH (Me ) Ph ---------- ――――――――――――――――――――――――― [Table 3]

[0099]

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[0100]

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[0101]

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[0102]

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[0103]

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[0104]

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[0105]

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[0106]

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[0107]

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[0108]

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[0109]

[Table 6] ――――――――――――――――――――――――――――――――――― R17 ―――――――――― ――――――――――――――――――――――――― Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, H, NH _{2 , OH, CH 2 CONH 2,} CH 2 cyclo-Pr, CH 2 CO 2 Me, CH 2 CO 2 Et, COMe, COEt, COPr, CO-iso-Pr, cOBu, CO-tert-Bu, CO-cyclo- Pr, COCF ₃ , CH (Me) CO ₂ Me, CH (Me) CO ₂ Et, CH ₂ Ph, CH _2- (2-Cl-Phenyl), CH _2- (3-Cl-Phenyl), CH _{2 - (4-Cl-Phenyl} ), CH 2 - (2-pyridyl), CH 2 - (3-pyridy _{), CH 2 - (4-} pyridyl), CH (CO 2 Et) 2, CH (CO 2 Me) 2, OPr, O-iso-Pr, OBu, O-tert-Bu, OCH 2 CH = CH 2, OCH (Me) CH = CH ₂ , OC (Me) ₂ CH = CH ₂ , OCH ₂ C≡CH, OCH (Me) C≡CH, OC (Me) ₂ C≡CH, OCH ₂ CH ₂ CH ₂ F _{, OCH 2 C H 2 F,} OCH 2 CH 2 CF 3, OCH 2 CH 2 CH 2 Cl, OCH (CH 2 F) 2, O CH 2 OMe, OCH 2 OEt, OCH 2 CH 2 OMe, OCH 2 CH 2 _{OEt, OC H 2 CH 2 OCH} 2 CH 2 OMe, CH 2 CH = CH 2, CH 2 C≡CH, CH 2 C≡ N, CH 2 CH 2 F, CH 2 CH 2 Cl, CH 2 CH 2 CH 2 F, CH ₂ OMe, OMe, OEt, CH ₂ OEt, CH ₂ C _{H 2 CH 2 Cl, CH 2} CH 2 CH 2 CH 2 F, C H 2 CCl = CH 2, CH 2 CBr = CH 2, CH (Me) C≡CH, CH (Me) CH = CH 2 or CH ( Me) C≡N ――――――――――――――――――――――――――――――――― The symbols in the table mean the following Represents _{Me: CH 3 Et: CH 2} CH 3 Pr: CH 2 CH 2 CH 3 iso-Pr: CH (CH 3) 2 cyclo-Pr: CH (CH 2) 2 Bu: CH 2 CH 2 CH 2 CH 3 sec- _{Bu: CH (CH 3) C} 2 H 5 iso-Bu: CH 2 CH (CH 3) 2 tert-Bu: C (CH 3) 3 cyclo-Bu: CH (CH 2) 3 Pn: CH 2 CH 2 CH ₂ CH ₂ CH ₃ cyclo-Pn: CH (CH ₂ ) ₄ iso-Pn: CH ₂ CH ₂ CH (CH ₃ ) ₂ neo-Pn; CH ₂ C (CH ₃ ) ₃ cyclo-Hex: CH (CH ₂ ) ₅ tert-Pn: C (CH ₃ ) ₂ C ₂ H ₅ Hex: (CH ₂ ) ₅ CH ₃ Hep: (CH ₂ ) ₆ CH ₃ Oct: (CH ₂ ) ₇ CH ₃ Ph, Phenyl: C ₆ H ₅ 4-Cl-Ph: 4-Cl-Phenyl The compound of the present invention is used. In doing so, it is usually mixed with a suitable solid carrier or liquid carrier, and further, if desired, a surfactant, a penetrant, a spreading agent, a thickener, an antifreezing agent, a binder, an anti-caking agent, a disintegrant, Add foaming agents, preservatives, anti-decomposition agents, etc., and prepare solutions, emulsions, wettable powders, aqueous solvents, wettable granules, aqueous granules, suspensions, emulsions, suspoemulsions, microemulsions It can be put to practical use in preparations of any dosage form such as powders, granules and gels. Further, from the viewpoint of labor saving and improvement of safety, the above-mentioned preparation of any dosage form can be provided by being enclosed in a water-soluble package. If necessary, it can be mixed with a plurality of other herbicides, insecticides, fungicides, plant growth regulators, fertilizers and the like at the time of preparation or spraying.

Examples of the solid carrier include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. And the like, synthetic silicic acid and synthetic silicate.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone;
Esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil; and water.

These solid and liquid carriers may be used alone or in combination of two or more.

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, and polyoxyethylene polyoxypropylene block copolymer. Nonionic surfactants such as oxyethylene sorbitan fatty acid esters, alkyl sulfates, alkyl benzene sulfonates,
Lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of alkyl naphthalene sulfonic acid formalin condensate,
Anionic surfactants such as polyoxyethylene alkyl aryl ether sulfates and phosphates, polyoxyethylene styryl phenyl ether sulfates and phosphates, polycarboxylates and polystyrene sulfonates, alkylamine salts and alkyl quaternary ammonium salts; Examples include cationic surfactants and amphoteric surfactants such as amino acid type and betaine type.

The content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 20 parts by weight based on 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

Next, a formulation example of a preparation using the compound of the present invention 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 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others, for example, anti-caking agent, anti-decomposition agent, etc. I can give you.

[Emulsion] Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents and decomposition inhibitors. Can be

[Suspension] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others, for example, antifreezing agents, thickeners And the like.

[Water dispersible granules] Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, a binder and a decomposition inhibitor. No.

[Solution] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, an antifreezing agent and a spreading agent.

[Granules] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, a binder and a decomposition inhibitor.

[Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, an anti-drift agent and an anti-decomposition agent.

When used, the above preparation is mixed with water for 1 to 100 times.
With or without dilution, the active ingredient is sprayed at a rate of 0.001 to 50 kg, preferably 0.01 to 10 kg, per hectare (ha).

Formulation Examples Specific examples of agrochemical formulations containing the compound of the present invention as an active ingredient are shown below, but the invention is not limited thereto. In addition,
In the following formulation examples, “parts” means parts by weight.

[Formulation Example 1] Water-dispersible compound of the present compound No. 1 243 20 parts Pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Carplex # 80D 2 parts (synthetic hydrous silicic acid: Shiono The above is uniformly mixed and pulverized into a wettable powder.

[Formulation Example 2] Emulsion Compound of the present compound no. 244 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) And

[Formulation Example 3] Suspending agent (flowable agent) 245 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C 0.5 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd.) Xanthan gum 0.2 Part Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspending agent.

[Compounding Example 4] Water dispersible granule (dry flowable) 250 75 parts Hytenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd.) Vanirex N 10 parts (Anionic surfactant: Nippon Paper Industries Co., Ltd.) Carplex # 80D 10 parts (synthetic hydrous silicic acid: trade name of Shionogi & Co., Ltd.) After uniformly mixing and pulverizing the above, adding a small amount of water, stirring and mixing, granulating with an extrusion granulator, drying and granulating water. It should be a sum.

[Formulation Example 5] Granules Compound of the present invention. 259 5 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed by stirring, granulated by an extrusion granulator, and dried to obtain granules.

[Formulation Example 6] Powder Compound No. 268 3 parts Carplex # 80D 0.5 parts (Synthetic hydrated silica: trade name of Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to form a powder.

For use, the above-mentioned wettable powder, emulsion, flowable powder and particulate wettable powder are diluted 50 to 1000 times with water so that the active ingredient is reduced to 0.000 per hectare (ha).
Spray to 1 to 10 kg.

Next, the usefulness of the compound of the present invention as a herbicide 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 cylindrical plastic cup with an inner diameter of 3.2 cm and a depth of 9 cm, water was added and mixed, and the water depth was 4
cm. Rice at the two leaf stage was transplanted to the above pot, and seeds of Nobie, Firefly and Konagi were mixed and sown. The pot was grown in a greenhouse at 25 to 30 ° C, and the compound of the present invention prepared according to the formulation example was treated on the water surface on the first day after sowing so as to have a predetermined dose. Three weeks after the treatment, the herbicidal effect on various weeds and the effect on rice were visually examined 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 4-1.

[0133] In each table, the No. Is the compound No. described in the examples. And the symbols have the following meanings. A: Nobie, B: Firefly, C: Onion, a: Rice Criteria 5: 90% or more of herbicide rate (almost completely withered) 4 ... 70% or more and less than 90% of herbicide rate 3 ... 40% or more and less than 70% of herbicide rate 2 ... Herbicidal rate 20% or more and less than 40% 1 ... Herbicidal rate 5% or more and less than 20% 0 ... Herbicidal rate less than 5% (almost no effect) [Test Example-2] Herbicidal effect test by treatment after weed emergence in flooded conditions After putting alluvial soil in a 3.2 cm, 9 cm deep cylindrical plastic cup, add water and mix to obtain a water depth of 4 cm.
cm. The above pots were mixed with soybean, firefly and corn seeds. Plants were grown in a greenhouse at 25 to 30 ° C. in a pot, and the compound of the present invention prepared according to the formulation example was treated on the 14th day after sowing so that a predetermined dose was applied to the water surface. Three weeks after the treatment, the herbicidal effect on various weeds was visually inspected according to the criteria of Test Example 1. The results are shown in Table 4-2. In addition, No. in each table. Is the compound No. described in the examples. And the symbols have the following meanings. A: Nobie, B: Firefly, C: Eel [Test Example-3] Herbicidal effect test by soil treatment Put sterilized flood soil in a plastic box of 33 cm in length, 33 cm in width and 8 cm in depth. , Black grass, strawberry, ragweed,
Blue-eyed totoro, shiroza, oak, oinu-nofuguri,
After mixing seeds of chickweed, corn, soybean, cotton, wheat and beet and covering about 1.5 cm, the compound of the present invention prepared according to the formulation example is evenly sprayed on the soil surface so as to have a predetermined amount. did. Three weeks after spraying 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. The results are shown in Table 4-3.

Note that, in each table, No. Is the compound No. described in the examples. And the symbols have the following meanings. D: Meishishiba, E: Enokorogosa, F: Oats,
G: black grass, H: strawberry, I: ragweed, J:
Blue-toed, K: Shiroza, L: Inodate, M: Big-nosed puffer, N: Hawk-be, b: Maize, c: Soybean, d: Cotton, e: Wheat, f: Beet [Test Example-4] Herbicidal effect test by foliage treatment Vertical Put the sterilized flood soil in a plastic box of 33cm, 33cm in width and 8cm in depth, and add crabgrass, enokorogusa, oats, blackgrass, ibis, ragweed,
Blue-eyed totoro, shiroza, oak, oinu-nofuguri,
Mixed seeds of chickweed, corn, soybean, cotton, wheat and beet, covered about 1.5 cm, and then 25 to 30 ° C
Were grown in a greenhouse for 14 days, and the compound of the present invention prepared according to the formulation example was evenly applied to the foliage so as to have a predetermined amount. Test example on herbicidal effects on various weeds and effects on crops 3 weeks after application of chemical solution-
It was visually inspected according to the criteria of 1. 0 is no effect and 5 is a 5-point scale showing complete withering. 4th result
-4 is shown in 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. D: Meishishiba, E: Enokorogosa, F: Oats,
G: black grass, H: strawberry, I: ragweed, J:
Blue-toed, K: White, L: Inuta, M: Big-nosed, N: Hawk, b: Maize, c: Soybean, d: Cotton, e: Wheat, f: Beet [Table 4-1]

[0136]

[Table 7] ――――――――――――――――――――――――――――――――― Compounds Dose No. g / a ABCa ――――――――――――――――――――――――――――――――――― 209 0.64 5 5 5 2 210 0.64 5 5 5 4 211 211 0.64 0 5 5 1 212 0.64 3 15 0 213 0.64 5 5 5 1 214 0.64 5 5 5 3 215 0.64 5 5 5 5 3216 0 .64 4 3 5 1 217 0.64 4 5 5 1 218 0.64 5 5 5 3 219 0.64 5 4 5 4 220 220 0.64 5 4 5 1 221 0.64 5 4 5 5 1 222 0.64 5 3 5 1 223 0.64 3 15 0 224 0.64 5 2 5 1 225 0.64 5 3 5 1 226 0.64 2 3 5 2 227 0.64 5 3 5 1 228 0.64 5 5 5 1 229 0.64 5 5 5 1 230 0.64 5 3 5 1 ――― -------------------------------

[0137]

[Table 8] ――――――――――――――――――――――――――――――――― Compounds Dose No. g / a ABCa ―――――――――――――――――――――――――――――――――― 231 0.64 5 2 5 0 232 0.64 5 4 5 3 233 0.64 5 5 5 1 234 0.64 5 4 5 1 235 0.64 5 5 5 2 236 0.64 5 5 5 3 237 0.64 3 225 1 238 0 .64 5 5 5 4 239 0.64 5 1 5 0 240 0.64 5 1 5 0 241 0.64 2 3 5 0 242 0.64 0 3 5 1 243 0.64 5 5 5 3 244 0.64 5 5 5 5 245 0.64 5 5 5 5 246 0.64 5 5 5 1 247 0.64 5 5 5 2 248 0.64 5 4 5 1 249 0.64 5 5 5 3 250 250 0.64 5 5 5 4 251 0.64 5 5 5 1 252 0.64 5 5 5 1 ――― -------------------------------

[0138]

[Table 9] ――――――――――――――――――――――――――――――――― Compounds Dose No. g / a ABCa ―――――――――――――――――――――――――――――――― 253 0.64 5 5 5 2 254 0.64 5 4 5 1 255 0.64 5 4 5 1 256 0.64 5 5 5 1 257 0.64 3 3 5 0 258 0.64 4 15 1 259 0.64 5 5 5 5 260 0 .64 004 261 0.64 5 5 5 3 262 0.64 4 5 5 2 263 0.64 3 5 5 1 264 0.64 1 -3 1 265 0.64 5 3 5 1 266 0.64 5 5 5 2 267 0.64 5 3 5 1 ――――――――――――――――――――――――――――――――― -2 table)

[0139]

[Table 10] ――――――――――――――――――――――――――――――――― Compound Dose No. g / a A B C ――――――――――――――――――――――――――――――――――― 209 0.64 4 4 4 210 0 .64 5 55 211 0.64 25 5 213 0.64 33 35 214 0.64 43 3 215 0.64 500 5 216 0.64 400 217 0.64 5 225 218 0. 64 5 5 5 219 0.64 5 4 5 220 220 0.64 1 1 221 0.64 4 3 4 222 0.64 4 1 4 223 0.64 10 2 224 0.64 4 3 4 225 0.64 4 3 5 226 0.64 0 1 4 227 0.64 5 2 4 228 0.64 5 1 5 229 0.64 5 2 5 230 230 0.64 5 2 4 231 0.64 10 0 3 ------ ――――――――――――――――――――――――――――― ―

[0140]

[Table 11] ――――――――――――――――――――――――――――――――― Compounds Dose No. g / a A B C ――――――――――――――――――――――――――――――――― 232 0.64 5 2 4 233 0 .64 3 3 5 234 0.64 3 2 4 235 0.64 5 3 5 236 0.64 5 3 5 237 0.64 0 0 3 238 0.64 4 4 4 239 0.64 100 0 240 0. 64 102 241 0.64 004 242 0.64 00 243 0.64 5 445 444 0.64 5 5 5 245 0.64 5 5 246 0.64 5 4 5 5 247 0.64 5 4 5 248 0.64 5 4 4 249 0.64 5 4 5 250 0.64 5 5 5 251 0.64 5 4 5 252 0.64 5 4 5 253 0.64 5 4 5 ---- ――――――――――――――――――――――――――――― ―

[0141]

[Table 12] ――――――――――――――――――――――――――――――――― Compounds Dose No. g / a A B C ――――――――――――――――――――――――――――――――――― 254 0.64 4 4 4 255 0 0.645 44 256 0.64 55 55 257 0.641 11-258 0.642 21 259 0.645 54 45 260 0.640-3 261 0.645 54 52 62 0. 64 4 44 263 0.64 4 -4 264 0.641 -1 265 0.64 4 3 3 266 0.64 5 4 4 267 0.64 4 4 4 ――――――――――― ―――――――――――――――――――――――― [Table 4-3]

[0142]

[Table 13] ――――――――――――――――――――――――――――――――――― Compound No. Positive dose g / a DEFGHIJKLMN bcdef ― ―――――――――――――――――――――――――――――――――― 209 1.6 5 5 5 4 5 5 5 5-5 5 3 1 0 4 5 210 1.6 5 5 4 4 5 5 5 5-5 5 4 1 0 4 5 211 1.6 5 1 1 0 5 4 5 5 5 1 1 0 0 0 0 5 212 1.6 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 1 213 1.6 1 2 1 0 2 0 3 4 5 5 5 1 0 0 0 5 214 1.6 4 4 4 3 5 3 1 5 3 5 3 4 4 3 4 5 215 1.6 5 5 4 4 5 4 5 5 5 5 5 4 3 5 3 5 216 1.6 3 3 1 0 5 1 1 5 0 3 0 0 1 0 0 0 217 1.6 4 4 1 2 5 2 0 5 1 2 1 4 3 3 1 4 218 1.6 5 5 2 3 5 5 5 5 5 5 5 4 4 3 1 5 219 1.6 5 5 2 3 5 5 5 5 5 5 5 4 3 3 2 5 220 1.6 3 3 0 1 3 4 5 4 4-0 2 0 0 1 1 221 1.6 5 4 1 1 5 0 4 5 5 5 1 5 4 3 1 5 222 1.6 5 5 1 2 5 5 5 5 5 5 4 5 4 4 2 5 223 1.6 0 0 0 0 0 0 0-0 4 1 0 0 0 1 2 224 1.6 4 3 0 0 3 0 4 4 5 0 0 0 0 0 0 2 225 1.6 5 4 0 0 4 4 5 5 5 5 5 0 1 2 0 5 226 1.6 2 0 0 0 3 2 5 5 5 0 0 1 0 0 0 5 227 1.6 5 4-4 5 1 5-5 5 5 1 0 0 1 5 228 1.6 5 5-4 5 5 5-5 5 5 4 1 0 2 5 229 1.6 5 5-5 5 5 5-5 5 5 4 1 0 3 5 230 1.6 5 4 5 5 3 2 5-5 5 5 0 0 0 5 5 231 1.6 2 1 0-3 5 4-5 5 5 0 0 0 0 4 ――――――――― ――――――――――――――――――――――――――

[0143]

[Table 14] ――――――――――――――――――――――――――――――――― Compound No. Drug dose g / a DEFGHIJKLMN bcdef ― ―――――――――――――――――――――――――――――――――― 232 1.6 5 5 2 4 5 5 5-5 5 5 5 3 4 1 5 233 1.6 5 4 0 0 5 3 5 5 5 5 3 2 0 1 2 5 234 1.6 0 1 1-2 0 4 1 4 4 4 0 0 0 0 5 235 1.6 5 4 1 2 5 2 5 5 5 5 4 0 1 1 1 5 236 1.6 5 5 3 4 5 5 5 5 5 5 5 5 3 3 4 5 237 1.6 4 4 0 0 5 5 5 5 5 5 1 4 2 2 1 5 238 1.6 5 4 4 2 5 5 5 5 5 5 5 4 2 3 4 5 239 1.6 4 4 2 3 2 1 4 5 0 4 5 0 0 0 1 5 240 1.6 4 3 2 3 5 1 5 5 5 5 4 0 0 0 1 5 241 1.6 4 0 0 0 3 1 2 5 0 0 0 0 0 0 0 0 242 1.6 3 1 0 0 3 1 4 5 5 1 0 0 1 1 0 3 243 1.6 5 5 5 5 5 5 5 5 5 5 5 5 3 4 4 5 244 1.6 5 5 4 4 5 5 5 5 5 5 5 4 1 5 4 5 245 1.6 5 5 5 4 5 5 5 5 5 5 5 5 1 5 4 5 246 1.6 5 3 2 3 5 3 5 5 5 5 4 1 1 2 4 5 247 1.6 5 4 2 3 5 4 5 5 4 5 5 4 0 0 3 5 248 1.6 4 4 0 0 3 1 4 5 5 5 4 0 0 0 0 4 249 1.6 5 4 2 2 4 2 4 5 5 2 5 0 0 0 3 4 250 1.6 5 5 4 4 5 5 5 5 5 5 5 4 2 4 4 5 251 1.6 5 5 1 5 5 4 5 5 5 5 5 4 1 1 3 5 252 1.6 5 4 1 2 5 3 5 5 3 5 5 0 0 0 3 5 253 1.6 5 5 3 3 5 4 5 5 5 5 5 3 1 1 3 5 254 1.6 5 4 1 1 5 3 5 5 4 5 4 0 0 0 1 5 ――――――――― ――――――――――――――――――――――――――

[0144]

[Table 15] ――――――――――――――――――――――――――――――――――― Compound No. Positive dose g / a DEFGHIJKLMN bcdef ― ―――――――――――――――――――――――――――――――――― 255 1.6 4 3 0 0 3 2 5 4 5-2 0 0 0 0 0 256 1.6 5 5 3 1 5 5 5 5 5-4 4 3 2 2 5 257 1.6 0 0 0 0 3 2 5 5 5-0 0 0 0 0 5 258 1.6 3 3 0 0 1 3 5 5 4 2 0 0 1 0 0 4 259 1.6 5 5 4 4 5 5 5 5 5 5 5 5 4 5 4 5 260 1.6 0 0 0 0 1 3 5 5 5 0 0 0 0 0 0 4 261 1.6 5 5 3 5 5 5 5 5 5 5 5 5 4 4 3 5 262 1.6 5 5 2 1 5 5 5 5 5 5 3 4 1 1 2 5 263 1.6 5 4 1 1 5 5 5 5 5 5 3 4 2 1 1 5 264 1.6 1 0 0 0 1 1 3--5 0 0 0 0 0 5 265 1.6 5 5 3 4 5 4 4-3 5 5 1 3 1 3 5 266 1.6 5 5 3 3 5 4 5 5-5 5 3 0 1 1 5 267 1.6 5 5 1 3 5 4 5 5 4 5 5 4 1 3 1 5 ―――――――――――――――――――――――――――――――― ――― [Table 4-4]

[0145]

[Table 16] ――――――――――――――――――――――――――――――――― Compound No. Positive dose g / a DEFGHIJKLMN bcdef ― ―――――――――――――――――――――――――――――――――― 209 1.6 5 5 5 4 5 5 5 5 5 5 5 4 5 5 4 5 210 1.6 5 5 5 5 5 5 5 5 5 5 5 4 5 5 4 5 211 1.6 5 4 2 2 5 5 5 5 5-5 3 4 4 2 5 212 1.6 2 1 1 1 4 3 5 4 5 4 3 2 2 5 1 4 213 1.6 5 5 2 3 5 5 5 5 5 5 5 3 4 5 2 5 214 1.6 5 5 5 4 5 5 5 5 5 5 5 4 5 5 4 5 215 1.6 5 5 4 4 5 5 5 5 5 5 5 4 4 5 4 5 216 1.6 4 4 2 2 5 5 4 5 5 5 5 3 5 5 2 5 217 1.6 4 4 3 2 5 4 4 5 4 5 5 4 4 5 4 5 218 1.6 5 5 2 4 5 5 5 5 5 5 5 5 5 5 2 5 219 1.6 5 5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 220 1.6 4 4 1 1 5 4 5 5 5 5 5 2 3 5 2 5 221 1.6 5 4 1 2 5 4 4 5 5 5 5 5 4 5 1 3 222 1.6 5 5 1 3 5 5 5 5 5 5 5 5 4 5 1 5 223 1.6 0 0 1 0 3 4 5 5 5 1 3 0 2 3 1 1 224 1.6 3 2 1 2 5 4 5 5 5 5 5 1 2 5 1 5 225 1.6 2 1 1 1 5 5 5 5 5 5 5 0 3 5 1 1 226 1.6 3 4 1 1 5 5 5 5 5 5 5 2 5 5- 5 227 1.6 5 5 3 2 5 5 5 5 5 5 5 4 5 5 1 5 228 1.6 4 5-4 5 5 5 5 5 5 5 4 4 5 2 5 229 1.6 5 5 5 5 5 5 5 5 5 5 5 3 5 5 5 5 230 1.6 4 5 5 3 5 5 5 5 5 5 5 3 5 5 2 5 231 1.6 0 2 1 0 5 4 5-5 5 5 1 5 5 1 5 ――――――――― ――――――――――――――――――――――――――

[0146]

[Table 17] ――――――――――――――――――――――――――――――――― Compound No. Positive dose g / a DEFGHIJKLMN bcdef ― ―――――――――――――――――――――――――――――――――― 232 1.6 5 5 4 5 5 5 5-5 5 5 5 5 5 5 3 5 233 1.6 4 4 2 3 5 5 5 5 5 5 5 1 4 5 1 5 234 1.6 2 3 0 2 5-5 5 5 5 5 1 4 5 0 5 235 1.6 5 5 5 5 5 5 5 5 5 5 5 2 5 5 4 5 236 1.6 5 5 4 3 5 5 5 5 5 5 5 4 5 5 4 5 237 1.6 5 5 3 1 5 5 5 5 5 5 4 2 4 5 1 5 238 1.6 5 5 3 2 5 5 5 5 5 5 5 5 5 5 4 5 239 1.6 5 4 2 4 5 5 5 5 5 5 5 2 3 5 2 5 240 1.6 5 5 0 4 4 5 5 5 5 5 5 2 4 5 1 5 241 1.6 4 2 0 0 5 3 5 5 4 5 3 1 2 5 0 5 242 1.6 3 1 0 0 5 3 5 4 5 3 3 1 4 5 0 5 243 1.6 5 4 5 4 5 5 5 5 5 5 5 4 5 5 5 5 244 1.6 5 5 5 5 5 5 5 5 5 5 5 4 5 5 4 5 245 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 246 1.6 5 4 4 3 5 5 5 5 5 5 5 3 5 5 4 5 247 1.6 5 4 4 3 5 5 5 5 5 5 5 3 5 5 2 5 248 1.6 5 4 1 2 5 5 5 5 5 5 5 3 4 5 2 5 249 1.6 5 5 4 2 5 5 5 5 5 5 5 3 5 5 3 5 250 1.6 5 4 5 5 5 5 5 5 5 5 5 5 5 5 4 5 251 1.6 5 5 1 5 5 4 5 5 5 5 5 4 4 5 5 2 5 252 1.6 5 4 5 5 5 5 5 5-5 5 3 4 5 2 5 253 1.6 5 5 5 4 5 5 5 5 5 5 5 3 5 5 3 5 254 1.6 5 4 2 3 5 5 5 5 5 5 5 4 4 5 1 5 ――――――――― ――――――――――――――――――――――――――

[0147]

[Table 18] ――――――――――――――――――――――――――――――――――― Compound No. Positive dose g / a DEFGHIJKLMN bcdef ― ―――――――――――――――――――――――――――――――――― 255 1.6 5 4 1 0 5 5 5 5 1 5 5 3 4 5 1 5 256 1.6 5 5 2 3 5 5 5 5 5 5 5 4 4 5 1 5 257 1.6 4 1 1 2 5 5 5 5 5 5 5 2 4 5 0 5 258 1.6 5 4 1 2 5 4 5 5 5 5 5 3 4 5 0 5 259 1.6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 260 1.6 2 1 0 0 5 3 5 5 5 5 2 3 3 5 0 5 261 1.6 5 5 4 4 5 5 5 5 5 5 5 5 4 5 3 5 262 1.6 5 5 3 2 5 4 5 5 5 5 5 4 4 5 2 5 263 1.6 5 5 2 1 5 5 5 5 5 5 4 4 4 5 1 5 264 1.6 5 3 1 1 5 5 5-3 5 4 3 3 5 1 5 265 1.6 5 5 5 4 5 4 5-4 5 5 5 5 5 3 5 266 1.6-5 5 4 5 5 5-5 5 5 4 5 5 3 5 267 1.6 5 4 4 5 5 5 5 5 5 4 5 5 4 5 2 5 ―――――――――――――――――――――――――――――――― ―――

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 487/04 148 C07D 487/04 148 A01N 43/90 104 A01N 43/90 104 105 105 105 106 106 106 C07D 498 / 04 105 C07D 498/04 105 513/04 381 513/04 381 519/00 301 519/00 301 (72) Inventor, Kennari 722, Tsuboi-cho, Funabashi-shi, Chiba Pref. 72) Inventor Shigeomi Watanabe 1470 Shirooka, Shirooka-machi, Shiraoka-cho, Minami-Saitama-gun, Saitama (72) Inventor Kunimitsu Nakahira 1470 Shirooka, Shirooka-cho, Shiraoka-cho, Minami-Saitama-gun, Saitama Nissan Kagaku Kogyo Co., Ltd. In the laboratory (72) Inventor Tohru Oki Nissan 1470, Shirooka, Shirooka-cho, Minamisaitama-gun, Saitama Bioscience Research Institute, Gaku Kogyo Co., Ltd. EE04 EE05 FF02 FF03 FF05 GG02 GG03 GG04 GG05 HH01 HH02 4C072 AA01 BB02 CC03 CC11 CC16 EE02 EE15 FF09 GG07 HH02 MM06 UU02 4H011 AB01 AB02 BA05 BB09 BC06 BC07 DA02 DA13 DA15 DA16 DD04

Claims (2)

[Claims] (1) Formula (1):[Where Rf is C₁-C_FourX represents a haloalkyl group;
And Y are each independently a carbon atom, a nitrogen atom, an oxygen atom
X to Y represent N = N, C (Ra) = C (Rb) (Ra, Rb
Is independently a hydrogen atom, a halogen atom, C₁-C_Four
Alkyl group, C₁-C_FourAlkoxy group, C₁-C_FourHaloa
Alkyl, hydroxyl, amino, mercapto, carboxyl
Sil group, hydroxymethyl group, carbamoyl group, holmi
Group, C₁-C_FourAlkylcarbonyl group, C₁-C_FourAl
Coxycarbonyl group, C₁-C_FourAlkylamino group, C
_Two-C ₆Alkenyl group, C_Two-C₆Alkynyl group, C₁−
C_FourAlkyl mercapto group, C_Three -C₆Alkenylamino
Group, C_Three-C₆Alkynylamino group, benzyloxy
Group, benzylamino group, C₁-C_FourAlkylsulfini
Group, C₁-C_FourAlkylsulfonyl and pyridyl groups
Or an optionally substituted phenyl (SP1) group (substituted
The optionally substituted phenyl (SP1) group refers to a halogen
Atom, C₁-C_FourAlkyl group, C₁-C_FourAn alkoxy group,
C₁-C_FourHaloalkyl group, C₁-C_FourHaloalkoxy group
Or phenyl which may be substituted by a phenyl group
Represents a radical. ). ), C (Ra) = N (Ra
Represents the same meaning as described above. ), N = C (Ra) (R
a has the same meaning as described above. ), CH (Ra) CH
(Rb) (Ra and Rb represent the same meaning as described above.)
You. ), CH_TwoCH_TwoCH_Two, CH = CHCH_Two, CH_TwoC
H = CH, NHC (Ra) Rb (Ra and Rb are as defined above.
Represents the same meaning as ), C (Ra) (Rb) NH
(Ra and Rb represent the same meaning as described above), C
(= O) C (= O), CH_TwoC (= O) NH, CH_TwoCH
_TwoSO_Two, C (= O) CH (Ra) (Ra is as defined above)
Indicates meaning. ), CH (Ra) C (= O) (Ra is before
Represents the same meaning as ), C (= O) NH, C (=
S) NH, NHC (= O), NHC (= S), C (=
O) C (Ra) = N (Ra represents the same meaning as described above.)
You. ), C (= O) C (Ra) = C (Rb) (Ra and
And Rb have the same meaning as described above. ), C (Ra) =
C (Rb) C (＝ O) (Ra and Rb are the same as above)
Indicates meaning. ), N = C (Ra) C (= O) (Ra is
Represents the same meaning as above. ), CH (Ra) C (=
O) NH (Ra represents the same meaning as described above), C
(= O) N (Ra) C (= O) (Ra is the same as above.
Represents taste. ), C (Ra) = NC (= O) (Ra is before
Represents the same meaning as ), C (Ra) O (Ra is before
Represents the same meaning as ), C (= O) O, OC (=
A represents a nitrogen atom or CH, Z represents an oxygen atom, a sulfur atom, NRc (Rc is a hydrogen atom, C
₁-C_FourAlkyl group, C₁-C_FourAlkoxycarbonyl
Group, C₁-C_FourAlkoxycarbonylmethyl group or position
Optionally substituted phenyl (SP2) group (substituted
A phenyl (SP2) group which may be present is a halogen atom,
C₁-C_FourAlkyl group, C₁-C_FourAlkoxy group or C
₁-C_FourMay be substituted by a haloalkyl group
A phenyl group) or NNHRc (Rc is as defined above)
Represents the same meaning. Rg represents a hydrogen atom, a halogen atom, a cyano group, C₁-C_Four
Alkoxycarbonyl group, C_Three-C₆Alkenyl group, C
_Three-C₆Alkynyl group or C₁-C_FourRepresents an alkyl group
R1 represents a hydrogen atom or a halogen atom, R5 represents a hydrogen atom or a halogen atom, R2 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group,
Thiocarbamoyl group, carbamoyl group, mercapto group,
Hydroxyl group, amino group, formyl group, carboxyl
Group, vinyl group, ethynyl group, trimethylsilylethynyl
Group, cyanomethyl group, sulfamoyl group, phenyl group,
Benzyl group, C₁-C₈Alkyl group, C_Three -C₈Alkene
Group, C_Three-C₈Alkynyl group, C₁-C_FourHaloalkyl
Group, C₁-C_FourAlkoxy group, C₁-C_FourHaloalkoxy
Group, C_Three-C₈Haloalkenyl group, C_Three-C₈Haloalk
Nyl group, C₁-C_FourAcyl group, C₁-C_FourAlkylsulfo
Nyl group, C₁-C_FourAlkylthio group, C₁-C_FourAlkoki
Shi (C₁-C_Two) Alkyl group, —CO_Two(C₁-C_FourArchi
) Group, -CON (C₁-C_FourAlkyl)_TwoGroup, -CON
H (C₁-C_FourAlkyl) group, -NH- (C₁-C_FourAl
Kill) group, -N (C ₁-C_FourAlkyl)_TwoGroup, -S-CO
_Two(C₁-C_FourAlkyl) group, —O—Q—CO _Two(C₁−
C_FourAlkyl) group (where Q is a saturated or unsaturated moiety)
May be branched, halogen atom, C₁-C_FourAlkoki
Si group, C₁-C_FourAlkoxycarbonyl group, cyano group,
Phenyl group, C₁-C_FourHaloalkyl group, C₁-C_FourAl
Koxy (C ₁-C_Four) Alkoxy group, C₁-C_FourAcyl
Group, C₁-C_FourAlkoxy (C₁-C_Four) With an alkyl group
Or C which may be substituted by an oxygen atom₁-C₈Al
Represents a kylene chain. ), Phenylethyl group, -Q-CO
_Two(C₁-C_FourAlkyl) group (where Q is as defined above)
Represents taste. ) Or -NH-Q-CO_Two(C₁-C_FourA
Alkyl) group (however, Q represents the same meaning as described above)
R3 represents -O-R11 (R11 is C_Three-C₈Cycloalkene
Nyl group, C_Three-C₈Cycloalkenyl (C₁-C_Four) Al
Kill group, cyano (C_Two-C₆) Alkyl group, cyano (fe
Nyl) methyl group, indanyl group, (C₁-C_FourAlkoki
Shi)_Two(C₁-C_Four) Alkyl group, C₁-C_FourAlkoxy
(C₁-C_Four) Alkoxy (C₁-C_Four) Alkyl group, C₁
-C_FourHaloalkoxy (C₁-C_Four) Alkyl group, C₁-C
_FourAlkoxy (C₁-C_Four) Haloalkyl group, C₁-C_FourC
Lower alkoxy (C₁-C_Four) Alkoxy (C₁-C_Four) Al
Kill group, C_Two-C₆Alkenyloxy (C₁-C_Four) Archi
Group, C _Two-C₆Alkynyloxy (C₁-C_Four) Alkyl
Group, C₁-C_FourAlkylthio (C₁-C_Four) Alkyl group
To (C_Three-C₈) Cycloalkyl group, C₁-C_FourAcyl (C
₁-C_Four) Alkyl group, C₁-C_FourAlkylsulfonyl (C
₁-C_Four) Alkyl group, (C₁-C_FourAlkoxycarboni
Le)_TwoMethyl group, pyridyl (C₁-C_Four) Alkyl group, 5
A trifluoromethyl-3-chloro-2-pyridyl group,
(Optionally substituted phenyl (SP3) group) carbo
Nyl group, (optionally substituted phenyl (SP1) group
Is a halogen atom, C₁-C_FourHaloalkyl group, C₁
-C_FourAlkyl group, C₁-C_FourAlkoxy group, C₁-C_Four
Haloalkoxy group, methanesulfonyl group, C₁-C_FourA
Alkoxycarbonyl group, nitro group, hydroxyl group,
Amino group, cyano group, -O-CH (CH_Three) CO_Two(C₁−
C_FourAlkyl) group or -O-CH_TwoCO_Two(C₁-C_FourA
Phenyl) group which may be substituted by
Phenyl) (optionally substituted phenyl (SP1)
Group) oxy (C₁-C_Four) Alkyl groups, (substituted
The phenyl (SP1) group has the same meaning as described above.
You. ), (Optionally substituted phenyl (SP1)
Group) -Q- (C₁-C_Four) Alkyl groups, (Q and substituted
The optionally substituted phenyl (SP1) group has the same meaning as described above.
Represents taste. ), Het group (Het group means one oxygen atom
Or saturated or unsaturated, characterized by containing two
Represents a 3- to 6-membered heterocycle containing a bond. ) Or-
Q-Het group (Q and Het groups have the same meaning as described above.)
Express. ). ), -NH-R11 (R11 is
Represents the same meaning as ), -S-R11 (R11 is
Represents the same meaning as above. ), C_Three-C₈Alkenylo
Xycarbonyl (C₁-C_Four) Alkyl group, C_Three-C₈Al
Quinyloxycarbonyl (C₁-C_Four) Alkyl group, -N
HCO- (C₁-C_Four) Alkyloxycarbonyl (C₁
-C_Four) Alkyl group, —N (R15) CO— (C₁−
C_Four) Alkyloxycarbonyl (C₁-C_Four) Alkyl
Group (R15 is C₁-C₆Alkyl group, C_Three-C₈Alkene
Group, C_Three-C₈Alkynyl group, C₁-C_FourHaloalkyl
Group, C_Three-C₈Haloalkenyl group, C_Three-C₈Halo alkini
Group, C₁-C₆Acyl group, formyl group, cyano (C₁−
C_Four) Alkyl group, C₁-C_FourAlkoxy (C₁-C_Four)
Alkyl group, C₁-C_FourAn alkoxycarbonyl group or
—C (＝ O) (optionally substituted phenyl (SP
3) group) group (provided that phenyl (S
The group P3) has the same meaning as described above. ) And R
4 is a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group,
No group, C₁-C_FourAlkyl group, C₁-C_FourAn alkoxy group or
Represents a mercapto group, and R3 and R4 optionally include oxygen, nitrogen, sulfur, and carbon atoms
5 having a saturated or unsaturated bond.
R2 and R3 may be a heterocyclic ring as shown in formulas (a) to (f).
May be formed,Note that Rf, Rg, A, X,
Y, Z, R1, R4 and R5 represent the same meaning as described above.
R17 is a hydrogen atom, a hydroxyl group, an amino group, C₁-C₆Al
Kill group, C_Three-C₈Alkenyl group, C_Three-C₈Alkynyl
Group, C₁-C_FourHaloalkyl group, C_Three-C₈Haloalkenyl
Group, C_Three-C₈Haloalkynyl group, C₁-C₆Acyl group,
Formyl group, benzoyl group, C₁-C₆Alkoxy group, C
_Two-C₈Alkenyloxy group, C_Two-C₈Alkynyloxy
Group, C₁-C₆Haloalkoxy group, C₁-C_FourAlkoxy
(C₁-C_Four) Alkoxy group, CH_TwoCONH_Two, CH
(CO_Two− (C₁-C_FourAlkyl))_TwoGroup, CH_Two-(Piri
Jil) group, C₁-C₆Haloalkylcarbonyl group,
Nasyl group, C_Three-C₈Cycloalkyl (C₁-C_Four) Al
Kill group, C₁-C_FourAlkoxy (C₁-C_Four) Alkyl
Group, -Q-CO_Two(C₁-C_Four) Alkyl group (where Q is
Represents the same meaning as above. ) -Q-CN group (however, Q
Represents the same meaning as described above. ) Or -Q- (substituted
Phenyl (SP3) group which may be
And the optionally substituted phenyl (SP3) group
Represents the same meaning as Wherein R28 and R29 each independently represent a hydrogen atom,
Group, halogen atom, C₁-C₆Alkyl group, C_Two-C₈A
Lucenyl group, C_Two-C₈Alkynyl group, C₁-C_FourHaloal
Kill group, C₁-C_FourAcyl group, C₁-C_FourAlkoxy (C₁
-C_Four) Alkoxy group, C₁-C_FourAlkoxy group, C₁-C
_FourAlkoxycarbonyl group, C₁-C_FourAlkoxy (C₁−
C_Four) Alkyl group, C₁-C_FourAlkylthio group or substitution
An optionally substituted phenyl (SP3) group (substituted
The phenyl (SP3) group which may be represented has the same meaning as described above.
I forgot. Where R28 and R29 in the formula (a) are both hydrogen atoms
When R28, R29 and R30 in the formula (b) are all water
R28 and R29 work together to form an acid
R30 may be a hydrogen atom, C₁-C₆Alkyl group, C₁-C_FourHalo
Acyl group, C₁-C₆Haloalkyl group, C_Two-C₈Alkene
Group, C_Two-C₈Alkynyl group, C₁-C₆Acyl group, C₁
-C_FourAlkoxycarbonyl group or C₁-C_FourAlkoki
Shi (C₁-C_Four) Represents an alkyl group, provided that these compounds have optical isomers and diastereomers
-When there is a geometric isomer,
And both isolated isomers. ]
Compounds and salts thereof. 2. A herbicide comprising the compound according to claim 1 as an active ingredient.