JPH01250361A - Pyridazinone derivative and insect pest controller - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [R is alkenyl, alkinyl, alkyl which may be substituted with alkoxy, G-Ra (G is H, RbO, RbS, RhNH, CN where Rb is alkyl); Ra is alkylene, alkenylene, cycloalkylene; A is H, halogen, alkyl, alkoxy, alkylthio; R<1> is H, halogen, alkoxy, hydroxyl; X is O, S; J is formulas II-IV (R<2>, Rc-Rf are H, alkyl; Q is substituted phenyl, naphthyl)]. EXAMPLE:5-(4-t-Butylbenzylthio)-4-chloro-2-[(2,2-dichloro-1,1-dimethyl )-ethyl]-3(2H)- pyridazinone. USE:Insecticide, acaricide, nematocide and repellent against mites living upon animals. PREPARATION:For example, a compound of formula V (Z<1> is halogen, azole) is allowed to react with an alcohol or thiol of the formula: HX-J in a solvent, in the presence of a base to give the compound of formula I.

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a novel 3(2+1)-pyridazinone derivative and an insecticide containing the derivative as an active ingredient. This invention relates to an acaricide, a nematocide, and an exterminator for mites parasitic on animals. [Prior Art] The following patents are related to the present invention. European Patent Publication 0088384 European Patent Publication 0134439 European Patent Publication 0183212 European Patent Publication 0199281 European Patent Publication 0210647 European Patent Publication 0193853 European Patent Publication 0232825 The known compounds contained in these patents have the general formula ( IT
). The characteristics of these patents are 2For example, European Patent Publication 00
No. 88384 1 European Patent Publication No. 0134439. European Patent Publication No. 0183212, European Patent Publication No. 0199281 and European Patent Publication No. 023
No. 2825 is characterized in that Y'' is an oxygen atom or a sulfur atom, but R1 is an alkyl group, and European Patent Publication No. 0210647 is characterized in that Ro is an aryl group. European Patent Publication No. 0193853 is characterized in that Ro is an aryl group. yl is a nitrogen atom or an oxygen atom, and R1 is a hydrogen atom or an alkyl group. The compound of the present invention is a novel compound not covered by these prior art. On the other hand, West German Publication No. 3328770 In this publication, the compound represented by the following formula is disclosed. In this publication, the above compound A is only disclosed as a synthetic intermediate, and the target compound derived from this compound A is not suitable for agricultural use. It has been described that it has a bactericidal effect. However, it has a different chemical structure and different uses than the compound [1] of the present invention. Pl [wherein, R is an alkenyl group having 2 to 16 carbon atoms, 2 carbon atoms]
~16 alkynyl group, C3-8 alkoxy substituted with C1-6 alkoxy or G-R
Represents a-. (G is a hydrogen atom, Rb0-. OOO 1?bO(:NH-, RbN11COz-, l1lbN
Represents I+-, (1?b) ZN- or a cyano group. (R
b represents an alkyl group having 1 to 4 carbon atoms. ) Ra is an alkylene group having 3 to 16 carbon atoms substituted with a halogen atom,
An alkenylene group having 2 to 16 carbon atoms substituted with a halogen atom, and an alkynylene group having 2 to 16 carbon atoms substituted with a halogen atom. A cycloalkylene group having 3 to 8 carbon atoms substituted with a halogen atom, a cycloalkenylene group having 5 to 8 carbon atoms substituted with a halogen atom, and a cycloalkenylene group having 5 to 8 carbon atoms substituted with a halogen atom
~8 oxacycloalkylene group, a thiacycloalkylene group having 5 to 8 carbon atoms substituted with a halogen atom, a cycloalkyl group having 3 to 8 carbon atoms, and an alkylene group having 1 to 4 carbon atoms substituted with a halogen atom, An oxirane group and a halogen atom-substituted alkylene group having 1 to 4 carbon atoms, an optionally substituted phenyl group and a halogen atom-substituted alkylene group having 1 to 4 carbon atoms, or an optionally substituted heterocyclic group and represents an alkylene group having 1 to 4 carbon atoms substituted with a halogen atom. ) A is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; 4 represents an alkylsulfonyl group. R1 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or a hydroxy group. X represents an oxygen atom or a sulfur atom. J is -CII-Q, -CIICI+-B,
-CIICIICH-Q, -C)lc=c-Q. RcRd RcRdRe R
cRdReII Ill l1l -CIICX'-Q, -CIICIIICII-CO
□Rf, -CIIC=C-CO2Rf. Re -CIICIIX'CRf, -CIICIIX'C
0Jf, -CIICHCII-C=C-11al. -CIIC11C=CC1hORf, -C11C=N
ORf or =C1 (represents CIIO-N=CHRf. (R", Rc, Rd, Re and Rf each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Rg XI represents 10-, - represents S-, -NH- or -N-,
(Rg represents an alkyl group having 1 to 4 carbon atoms.) H
al represents a /S rogen atom. ) Q represents a substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted heterocyclic group, and Ql represents an optionally substituted phenyl group, an optionally substituted funathyl group, or an optionally substituted heterocyclic group. Represents a ring group. ] represented by 3(2
+1)-pyridazinone derivative. This invention relates to a method for producing the derivative, and an insecticide, acaricide, nematicide, and a mite repellent that parasitizes animals, which contain one or more of the derivatives as an active ingredient. It has been found that the compound of the present invention represented by the linear formula (1) has excellent insecticidal, acaricidal, and nematocidal effects. For example, a group of known compounds represented by the -line formula [■] have strong insecticidal, acaricidal, nematicidal, and bactericidal activities. Although it has a wide insecticidal spectrum and is excellent in fast-acting properties, the compound of the present invention has a slow-acting effect because it has the effect of inhibiting the metamorphosis of pests. In addition, the compounds of the present invention are effective against various harmful pests at extremely low drug concentrations, such as agricultural pests such as the black leafhopper, brown planthopper, green peach aphid, and diamondback moth, and sanitary pests such as Culex mosquito, house fly, and German cockroach. , ants etc.
These include the grain storage pests such as the brown elephant, the white-spotted moth, and the termites, which are household pests, and mites and lice, which are livestock pests. That is, it has been found that Orthoptera, Termite, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, mites, and lice can be effectively controlled. This effect was specifically described in the biological test examples described later. In J of the above-mentioned linear formula (1), when Q is an aryl group, it means a phenyl group having a substituent or a naphthyl group which may be substituted. In the case of 1, it means an optionally substituted phenyl group or an optionally substituted naphthyl group. The types of substituents include 2, for example, a halogen atom, an alkyl group, an alkenyl group, and an alkynyl group. Cycloalkyl group, alkyloxy group, alkenyloxy group, alkynyloxy group, methylenedioxy group, halogenomethylenedioxy group, alkylthio group, alkenylthio group, alkylsulfinyl group, alkylsulfonyl group, cycloalkyloxy group, haloalkyl group, Haloalkyloxy group. Haloalkylthio group, alkylamino group, alkylcarbonylamino group, nitro group, cyano group, hydroxyl group, alkylcarbonyl group, alkoxycarbonyl group, carboxyl group, aryl group, aryloxy group, arylthio group, arylamino group. Arylcarbonyl group, arylmethyleneoxy group, aryloxymethyl group, arylmethylenecarbonyl group, unsubstituted or substituted pyridyloxy group, hydroxyalkyl group, alkylcarbonyloxyalkyl group, alkoxyalkyl group, alkylthioalkyl group, alkylcarbonyl Examples include an alkyl group, an alkoxycarbonylalkyl group, a cyanoalkyl group, and a haloalkylcarbonyl group. Above − wire system (

In J of [ ], Q or 01 is a heterocyclic ring
In the case of a group, the heterocycle is, for example, thiophene, fluoride, etc.
Lan, pyrrole, imidazole, thiazole, oxazo
ole, pyrazole, pyridine. Pyridazine, pyrimidine, pyrazine, benzoxazole
benzthiazole, benzothiophene. Dibenzothiophene, benzofuran, benzimidazole
ru, indole, indazole, quinoline 1 isoquinol
Examples include quinoxaline and quinoxaline. In the case of a heterocyclic group having a substituent, the type of the substituent
As 1, for example, a halogen atom, an alkyl group, an alkoxy
cy group, alkylthio group, alkylsulfonyl group, halo
alkyl group, haloalkoxy group. Nitro group, cyan group, alkylcarbonyl group, phenyl
group, substituted aryl group, etc. Compounds of the invention can be prepared by a number of methods. Two of these methods are as follows. (Method 1-a) 1 Compound of the present invention (1) (Method 1-b) 1 Compound of the present invention [! ] Mother -mυ- (Method 2-a) 1 Compound of the present invention (1) (Method 2-b) 1 (IX) (X) K. Compound of the present invention (1) (Method 2-C) H゛0゛9 Compound of the present invention (I) Figure-j;
LL (Method 3-a) H" (Ill) 01)e (XI[I) (XI[[) + Z3-oI ・(XIV) 0 0e Compound of the present invention Compound of the present invention Compound of the present invention (hereinafter referred to as the margin) [ In diagram (1), diagram (2) and diagram (3),
RlA, R', X, X', Rc, R,,
R,, R,, 0 times and J represent the same meaning as above, Z
l represents a halogen atom or an azole group, and Z2 represents a halo
Gen atom, alkyl sulfonate group and aryl sulfonate group
represents a phonate group, Z″ represents a halogen atom, and R3 represents a
Represents a compound with a double bond, R4 is a reactive functional group
represents a substituent having ] Diagram (1), diagram (2) and
In the reaction shown in Scheme (3), the solvent is
alcohols (e.g. methanol, ethanol, etc.),
Ketones (e.g. acetone, methyl ethyl ketone, etc.)
, hydrocarbons (e.g. benzene, toluene, etc.),
esters (e.g. isopropyl ether, tetrahydro
furan, 1,4-dioxane, etc.), amides (e.g.
N,N-dimethylformamide, hexamethylphosphoryl
(e.g. triamide), halogenated hydrocarbons (e.g.
(chloromethane, dichloroethane, etc.) can be used.
Wear. Also, if necessary, use a mixed solvent of these solvents or water.
A mixed solvent with can also be used. As a base
, inorganic bases (e.g., sodium hydride, sodium hydroxide)
potassium hydroxide, sodium carbonate, potassium carbonate
, sodium bicarbonate, etc.) and organic bases (e.g., sodium bicarbonate, etc.) and organic bases (e.g., sodium
Thorium methoxide, sodium ethoxide, tri
ethylamine, pyridine, etc.) can be used. Ma
In addition, if necessary, add a tetraammonium salt (e.g.
For example, triethylbenzylammonium chloride, etc.)
may be added as a catalyst. The reaction temperature is -2
The range is from 0'C to the boiling point of the solvent used in the reaction.
However, the boiling temperature of the solvent used in the reaction can be lowered from -5°C.
The range of points is more desirable, and the molar ratio of raw materials can be set arbitrarily.
However, it is possible to carry out the reaction at equimolar or close to equimolar ratios.
is advantageous. More specifically, the (1-a method) in diagram (1) is expressed by the -line formula (
21 of the compound represented by III) is represented by the general formula (IV)
alcohols or thiols in the presence of a base.
The compounds of the present invention can be prepared by reacting them in a suitable solvent with
N) can be produced. Zl is a halogen atom, especially a chlorine atom
A bromine atom is preferred, and azoles, especially l-imida
A sol group is preferred. As a solvent, N,N-dimethylformamide, methanol
solution, ethanol, toluene and toluene-water mixture
A medium is preferable, and an inorganic base is preferable as a base, especially an inorganic base.
Sodium carbonate, potassium carbonate, sodium hydroxide, water
Potassium oxide is preferred, and the reaction temperature is 20°C.
to 50'C is preferred. In this reaction, -a formula [I
V) Compounds substituted with alcohols or thiols
Materials may be produced as by-products. In that case, separate this by-product.
It became necessary to separate the compounds of the present invention and purify them by conventional methods.
Depending on the method (recrystallization, column chromatography, etc.)
Separate and purify. The (1-b method) in diagram (1) is expressed by the -line formula (V)
Pyridazinone derivatives are alkyl represented by the general formula [■]
Halides or alkyl sulfonates in the presence of a base
The compounds of the present invention can be prepared by reacting them in a suitable solvent under
Can manufacture things. Z2 is preferably a chlorine atom or a bromine atom
, as a solvent, N,N-dimethylformamide, meth
alcohol, ethanol, acetonitrile, toluene, toluene
A mixed solvent of ene-water is preferable, and the base is an inorganic base.
are preferred, especially sodium carbonate, potassium carbonate, hydroxide
Sodium hydroxide and potassium hydroxide are preferred. The reaction temperature is preferably 20"C to 120"C.
, when XH of the pyridazinone derivative (V) is OH,
Preferably from 20°C to 120°C, when XH is SH
The temperature is preferably 20°C to 50°C. (Method 2-a) of scheme (2) is based on the pyridazinone derivative [■
] to alkylate the 2nd position with R-Z” [■]
Therefore, the compound (1) of the present invention can be produced. By adding an inorganic or organic base to the reaction system.
Increasing the reactivity of pyridazinone derivative [■] and making it into the present invention
Facilitates the manufacture of compounds. The (2-b method) in diagram (2) is expressed by the − line formula (IX).
N-halogenoviridazinone represented by the general formula (X)
The compound of the present invention (
1) can be manufactured. (tX) (2-b method) is based on related technology, British Patent No. 999448.
The compound (I) of the present invention can be prepared by referring to
This method is suitable for Zl is a halogen atom, especially a chlorine atom, a bromine atom, an iodine atom
Elementary atoms are preferred, and the pyridazinone derivative (IX) and the
Mol or excess amount (10 times the mole) of olefin (X)
By reacting with at a temperature of -5°C to 120°C.
Therefore, the compound CI of the present invention can be produced. with a suitable solvent
This reaction proceeds well even if the reaction system is diluted. as a solvent
Hydrocarbons, halogenated hydrocarbons, ketones,
alcohols and lower alcohols are preferred, and more preferred.
Benzene, toluene, hexane, heptane, chloride
Methylene, chloroform, carbon tetrachloride, methyl ethyl chloride
ton, methyl isobutyl ketone, isopropyl ether
, 1,4-dioxane, methanol, ethanol are preferred.
Yes. When using a low boiling point olefin (X),
This can be achieved by using a pressurized reactor such as an autoclave.
Good results can be obtained. N-halogenopyridazinone derivative (IX) of raw material compound
according to West German Patent No. 1122069 or
It can be synthesized by the improvement method of drying. (2- of diagram (2))
Method c) is a pyridazinone derivative represented by -form (XI)
Chemically modifying the functional group within the N-substituent (R4) of the body
The compound of the present invention is converted into the desired N-substituent (R) by
This is a method for manufacturing a product CI). Specifically, the halogen atom contained in R4 is treated with a nucleophile (
R'O-, R'S-, CN-, R'COO-, etc.)
Substitution method, the oxirane group contained in R4 is
Nuclear or electrophilic reagents (alkyl halides, Lewis
A method of opening the ring with an acid reagent). There is a double bond contained in R4
Another method is to add a halogen molecule to the triple bond. to R4
The above nucleophile is attached to the double bond adjacent to the contained electron-withdrawing group.
Method for Michael-type addition of drugs, halogen contained in R4
By dehydrohalogenating the ion atom in the presence of a base,
method of forming a double bond, alcohol contained in R4
Oxidize the group to form an aldehyde group, ketone group or carboxyl group.
Method of oxidation to xyl group. The double bond contained in R4 is
Method of converting into oxirane group using a converting agent, containing in R4
aldehyde group, ketone group, carboxyl group or
A method for reducing carboxylic acid ester groups to alcohols. R
Reduction method for dehalogenating halogen atoms contained in 4
. The alcohol group contained in R4 can be treated with a halogenating reagent.
How to convert into halides. Al contained in R4
The call group and halogen atom are intramolecularly closed in the presence of a base.
How to synthesize oxacycloalkyl group by
Law. The thiol group and halogen atom contained in R4 are combined with a base.
thiacycloalkate by intramolecular ring closure in the presence of
How to synthesize kill groups. Examples of methods include: The (3-a method) in diagram (3) is expressed in the -form [mj
and a compound represented by -form EX II]
by reacting with in a suitable solvent in the presence of a base.
Thus, to produce a compound represented by the form [X I ]
Ru. Furthermore, this and - expressed in the form [XIV]
Heterocyclic halides or acid halides in the presence of a base.
The compound of the present invention is produced by reacting in a suitable solvent as follows.
It's a method. Specifically, the compounds included in the present invention include, for example:
The compounds shown in Tables 1, 2 and 3 below are listed.
It will be done. However, compounds in Tables 1, 2 and 3
are for illustrative purposes only, and the present invention is not limited to these.
[However, in the table, Me is methyl
group, Et is an ethyl group, P is a propyl group, Bu is a propyl group,
Butyl group, Pen means pentyl group, Hex means hexyl group.
group, Ph is unsubstituted phenyl group, t is tertiary
, S stands for secondary, i stands for iso, and C stands for cyclo.
vinegar. ] Note that among the compounds included in the present invention, asymmetric carbon atoms
In the case of compounds with atoms, optically active compounds (
+) body and (-) body are also included. Furthermore, among the compounds encompassed by the present invention, configurational isomers
If present, it also includes cis and trans forms.
It is something. (Hereafter, blank space) Table 1 RAXR'R"Y RAXI?'R"Y RAXR'R"Y MeCIICICII [lr CI
OHH4-IMeCllBrCIInr
CI OHII 4-C1RAXR'R"
Y RAXrl'l? ”Y [1rCIlzCII[1rCIIIlr
CI OII It 4-CIBrCtb
CIIBrCIIBr CI OII
II 4-1BrCII□CI[trCIIB
r Br OII It 4-
CIBrCIIzCIl[1rCIIBr
I OIt II 4-CICIC1l
zCChClh CI OHIt
4-CICIClbCCI□C1I□C
IO111+ 4-1CICIIxCCIz
CII* Or OII It
4-CICICII□CCI□CIl□
I OII II 4-CICICl
hCCIzCIIz CI OHII
4-DrCICIIzCChCII□
HOII II 4-CICI(1, It□
CChC1lt HOII H4-r
CICII□CChCII□ l0HH4-
1clclltccl□C1l! C.I.
OIf II 2,4-CIICICIIz
CCIzC! It Pr OIf
II 4-CICICIIzCCIzcIl□
5IEt OHII 4-1CI
CIhCChCIIt Or OCI
If 4-CICICIlyCCI□C11z
CI OHIt 2.3,4,
516-FsCICIIICGI□C11z
CI OIf H2,6-Ch,4-FC
ICII□CChCIh CI S
II II 4-CICICIIzCCh
CIIz CI S It ) I
4-Bu-tCIClhCCIzCIIt
CI S If H4-0 (Cllz
)sO4-0(Cllz)sO□CII□
CI S HH4-flitCICII□CC
ItCH1CI S II II 4
-CIl□OEtCICI1gCBrCICIlx
CI OHIt 4-CICIC1
lzCBrCICllz CI OI
t H4-1CICIItCBrC1 (&
Br OHtl 4-CICICIIz
CBrCICIb I OIt
H4-CICICIltCBrCICIIz
C1OIt If 4-BrCIC11g
4-BrCIC1l CI OIt
H2,4-ClICICHgCBrCICIb
Pr-1011It 4-CICICIlz
CBrCICHt SPr OIt
It 4-CICICHzCBrCIClllz
Br OOMe II 4-CI
CICHzCBrCICllz CI
OIt II 4-Bu-tCICIIzCB
rCIC) It C1OHH2-OMe, 4
-CICICIltCBrCICIIz
CI S■It 4-CICIC1lzCBr
CIC1lz CI S II
II 4-Bu-tRAXR'R1Y CICIItCBrCICHg CI
S H)I 4-CaH+tCICIIzCB
rCIC1li CJ S fl
H4-OCIIzCJIaCI-4゜CIC1lz
CBrCICHt CI SHI
t4-OCHtC4-0CHtCH=CII[1
rCICHt C1OHII 4-CI
BrCIlzCBrCICIl* CI
OII It 4-1BrCIlzCBrCIC
Hz Or OHII 4-CII
C11zCBrCICIIx I OIt
II 4-CI[]rCIhCBrCICHt
CI OII If 4-B
rBrCHzCBrCICllt Bu
OIt It 4-CIBrCH, CBrC
ICHx SOMe OIf II
4-CIBrCIIzCBrCICHt
CI OHIt 4-OBu-sBrCH
zCBrCICIIz CI S
HH44-ClBrC11tCBrCICHCI
S HIf 4-CIltOMeBrC1l
zCB4-Cl1tOCI S HH4-CI
+2-QIBrCIlzCBrCICIlg
CI S It If 4-OP
hBrClhCBrzCllz CI
OHIf 4-CIIC1hCBrzC1lz
CI OII It 4-[Br
Cl1tCBrzCIIz Br O
l(If 4-CIBrCIbCBrzCIIg
IOHfl 4-CIBrC
IIzCBriCIIi cl OI
I H4-BrBrCIIzC[lr*CHt
OMe OHII 4-BrBrC
HzCBrzCllt 5(hl!t O
HH4-CI[1rCHtCBrzC1lz
C1OHII 2,4.5-ChBrCHzC
BrgCIIg CI S It
If 4-CIBrCIIgCBrzCll
g cl S HII 4-
But-tBrCllzCBrzCHz C
I S H If 4-ChHaCI-4'
BrCToCBrgCHx CI S
If H4-C11g-(CI4-C1l,
4) BrCHzCBrgCHt -CIS
II It 4-NMetMeCHBrCC
Iz CI OHII 4-C
IMeCIIBrCClt C1Otl
H4-1M0CIICICCI!
CI OH+1 4-CIMeCIICICC
Iz CI OHH4-TCICH
iCllCICHx CI Ol(1
14-CICICII□CIICICIIx
CI OIf It 2,4-ChC
ICII□ClICIC11tCI OHH4-1
RAXR'l? ”Y CICIItCllBrCIlt cl
OIf II 4-ICIClhCIIBr
Cllz CI S I (H4-C
IBrClhCIICICIlz C1OH
II 4-C1 rcIlicllcIcHi
CI S II
If 4-CIBrClltCIICI
Cllt CI S HII
4-Bu-tBrCIIzCIl[1rCI11
cl OIf It 4-CIB
rCIIzCIIBrCIIg CI
OIt If 2.4-C1tBrCIIzCH
BrCIb C1OII If
4-rBrCllxCll[1rC11, Br O
HII 4-CIBrCIIgCII[1rC1h
IOHII 4-CIBrCI
I*CllBrCHg It OI
I H4-C1RAXR'R”Y BrCIlzC1lBrCH* II
OIt II 4-TBrCII*C11
BrCHHz CI S II
II 4-CIBrCIIz(:HBrCl1x
CI S It If
4-Bu-tBrCIIzCIIBr(Jlz
CI S II H4-CIlzP
hrcIItcHcIclI□ CI
OHII 4-C1rclhcHcI(Jb
C1Otl If 4-T[CI
IzCllCICIh Br OH
It 4-CIICII□CHCIGHz
IOH114-CIICIIICII
CIC11! I OIt II
44IC) 12CIICICIl□ CI
S II II 4-CIIClh
CIICCICIlz CI S
II II 4-Bu-trcIhcHcI
clh CI S tl
It 4-OEt[CHzCIICICIIz
CI S It If 3
．． 4-CI□ICl1zCIIBrCIlz
CI OII II 4-CIIC
IhCHBrCIIz C1OHII
2.4-C1zIC1ltCIIBrCIIt
cl OIf II 4-11
CIhCIIBrCllt Br
OHIf 4-C1rcIlzcHBrcIIf
I OII H4-CIIC
llzCIIBrCIlt CI
S If II 4-CIICHzCII
BrCIlz CI S II
H4-Bu-tMeCHCICCl(Me)
CI OHIt 4-CIMeCl
lCICCI(Me) CI OII
II 4-1MeCIICICBr(Me)
CI OII If 4-CIM
eCIICICBr(Me) CI O
II H4-1MeCIIBrCC1(Me)
CI OIf II 4-CI
MeCIIBrCCI(Me) C1OI
tIf 4-1MeCIIBrCBr(Me
) CI OIt II 4
-CIMeCHBrCBr(Me) CI
OHIf 4-1MeCCItCIl(Me
) CI OII H4-CIM
eCCItCIl(Me) CI O
HII 4-1MeC[lrCICII(Me)
CI OII II 4-C
IMeCBrCICll(Me) CI
OIt tl 4-[MeCBrzCIl
(Me) CI OHtl 4-
CIMeCBrzCIl(Me) C1O
HIf 4-1MezCCICIICI
CI OIt If 4-CIM
ezCCICICCI Cl OHI
f 2.4-ChRAXR'R”Y MezCCICHCI CI O
It)l 4-EMezCCICIICI
Br OIt II 4
-CIMezCCICIICI Or
OIt II 4-TMezCCICl
lCI I OIf H4
-CIMezCCICIICI I
OII It 4-1CIIzCII=
CII CI S tl
II 4-CIMetCCICIICI
CI S It H4-B
u4MezCCICIIC] CI
SHIt 4-0(Cllt)sOMe4
-0(Cllt)sOCI S HH4-[!
tMezCCIC1lCI cl
S It II 4-OChMezCCI
4-0Ch C1OIt H4-CIMe
zCCICHBr CI OHH
4-1MezCCIC1lBr Br
OIt H4-CIMezCCICIIBr
I OHII'LCIM
ezCCICIIBr CI S
II II 4-CIMezCCICII
Br CI S HH4-B
u-tMezCCICIIBr CI
S If If 4-OCIlzCJ
lnCI-4゜MezCCICIIBr
CI S If H4-4-3OEt
, CCICHBr CI S I
I If 4-OCIIzCII=CI4-0C
IIzCII=CII CI O
tl If 4-CIMe, CBrCllCl
CI OIf II 2
．． 4-ChMezCBrCIICI C
I OIf H4-1MezCBrC1lCI
Br OII H4-CI
MezCBrCHCI I O
HII 4-CIMezCBrCIICI
CI S II H4-CIM
ezCBrCIICI CI S
HH4-Bu-LMezC[1rCIICI
CI S H It 4-OP
hMetCBr4-0Ph cl
S It H4-(Ql)MezCBrCII
CI CI S H If
4-4-3Bu*CBrCllBr
CI OHII 4-CIMegCBrCH
Br CI OIf H2,4
-ClgMetCBrCIIBr CI
OHH4-1Bu*CBrCllBr
Br OIt 1+ 4-CIMe
zCBrCtlBr I OHH
4-CIMetCBrCIIBrH
O) I It 4-CIMezCBrCII[
lr II OHH4-1RAX
R'R”Y CICIlxCBr(CIIJr)CHg CI
OHH4-C1RAXR'R”Y CICIIzCCI(Me)C1lz OMe
OII It 4-CICICIIgCCI
(Me) CIlt OMe OHH4-1R
AXR'R”Y CICIItCBr(Me)CHtOMe
OHIf 4-1 ・ClCl, CBr(M
e) CHg SMe OII It
4-CICICHtCBr(Me)C1lz
Pr OHtl 4-CICICHzCBr
(Me)CHz SBu OHII 2
-F, 4-CICIC4-CICIC1ltCBr(c
l OOHtl 4-CICIC4-CICI
Cl1zCBr(CI OIt II 2-
CI, 4-FCICll*CBr(Me)C1li
CI S tl H4-CICICH
,CBr(Me)CHz CI S
)I H4-Bu-tCICII□CHCICB(C
HzCI) CI Otl If 4
-CICIC1lxC1lCICll (CHtCl)
CI Otl II 4-rCICI
liCIICICIl(CHzCI) Br
OHII 4-CICICH*CHClCl1(C
1ltC1) I OHII 4-CI
CIC1lCBrCl1(CHtCI) CI
OIt H4-CICIC1lzCIIBrCI
l(C1lxCI) C1OII 11 4
-1BrC11zC1lCICII(C)IJr)
C1OHIt 4-CIBrCHzCHCICH
(CHJr) CI O11II 4-1
BrCHiCHBrCll(CHt[lr) CI
OIf 11 4-CIBrCIIgCHB
rCIl(C1ltBr) CI 0 11
H44BrCHtCHBrCII (CIIJr)
Br OHIf 4-CIBrCllz
CIIBrCII(C1hBr) r OH
It 4-CIMeCCIzCH (CIltCI)
CI OHII 4-CIMeCG
IzCll(C1ltC1) CI O)
I H4-1MeCCIgCII (CHtCI)
Br OIt II 4-CIM
eCCIzCIl(CIIgCI) I
OIt It 4-CIRAXR'R"Y RAXR'R"Y RAXR'R"Y ChCllCChClh CI S
If H4-Bu-tCIBrCIICCI[
1rCIlz Br OII II
4-CICIBrCIICCIBrCHt
II OIf H4-CICIBrCllCC
IBrCIh HOIt II 4-I
CIBrCIICCl[1rCII* Bu
OIf If 4-C1RAXR'R”Y RAXR'R”Y MetCCICII Kano Clh Cl, O
If If 4-CIMexCCICIIBrC
Ht CI OHH4-1MevCBr
C1lCICHx CI OHH4-C
IMezCBrCIICICIIz C1O
HH4-IMexCBrCIICICHx
I OHII 4-CIMe, CBrC dish
rCllz CI OHIf 4-C
IMezCBrCIIBrClli CI
OIf II 4-IMetCBrCII
BrCIlt Br OHIf 4
-CIMetCBrCllBrCHg I
OHII 4-CICICHzCIICI
ClbCIh CI OIt H4-C
ICICII＊CIICICIIyoCl1m
CI OHH4-ICICHgCHCICII□C
11 layers Kano OHH4-CICICIIzCl
lCICtlgCHt I OIt
It4-CIBrCHzCIIBrCllzC
IIi CI OIt If 4-
C1[1rCIIzCIIBrCIIzCIIt
CI OHH44BrCH1CRBrCIlx
CIIx Br OII H4-CIB
rCIIgCIIBrCHiCHtI
OIt If 4-CIMeCCIzCII
CICIIz CI OHIt 4
-CIMeCCItCIICCHt cl
OHIf 4-IMeCClxCIICICI
lg Br OIf II 4-C
IMeCCIgCIICICIIt l
OHII 4-CIMeCCIBrCllBr
CIlt cl OHIf 4-CI
MeCCIBrClllBrCllt cl
o II II 4-IBr(CHI
e) iclIclcHi Cl 0 1
1 II 4-CIBr(CIli)scIlc
IclIg CI OIf II
4-1Or(CIlz)zcllBrcHt
CI OHIf 4-CIBr(Ctlz)
z forceBrCHt CI OIf It
4-IPrCCI(CIhCI)CIlg
cl OII II 4-CIPrCCl
(CIItCl)Cut CI OIf
H4-IPrCCI(CIlzCI)CHt
IOHH4-IPrCBr(CHmCl)
CHI CI OIt II 4-
CIPrCBr(CIItCl)CHx cl
OHH4-IBr(CHt)ncHclc)It
cl OHl(4-CIBr(CHg)
nclIcIcHm C1OHII 4-
IBr(C1ls)ncHBrclIt CI
OII H4-CIBr(CHi)acIIB
rcHx CI OII H4-1RA
XR'R”Y Br(Cllz)icIlc]clIz CI
OII it 4-CIBr(Cllz
), C11CIC1lz CI OI
If 4-1Br(CIIJiCIIBrCHt
CI O ■ II 4-C111
r(C1li)acIIBrcIIz CI
OHIt 4-14-1CIC1ltCII(
cl OHIf 4-CICICIIzCII
(Me) clo 11
1+ 4-[CICIIzC(Me)z
CI OIt If 4-CI4-
CICICl1zC(cl OIt It
4-ICI (CHZ)3 CI
ORII 4-CICI (CIRI 2
C1O I+ 4-ICI (CHIff
CI OH112,4-C1f
f1C1 (CIIJs Br
OII II 4-CIC1(CHt)s
IOHIf 4-CIC
I (CHz) + CI S
H)I4-CICI(C112)3
CI S II It 4-
Bu-tBr(C1h)s cl
OHH4-CIBr(C1li)z
CI OHIf 4-IBr (CIIJx
CI OHIf 2.4-
ChOr(CIIJs Br O
HII 4-CIOr(Cllt)z
I OIt If 4-CIB
r(Cllt)s cl S
II If 4-CIBr(CHtL
cl S It It
4-Bu-tl(CHJs CI
OHIt 4-C11(CIlg)s
CI OHH4-11 (CHtL
CI OHIf 2.4-
Cbl(C1li)z Br
OHIf 4-C11(CIl□)s
I OH! + 4-C11<C,H
,)3 CI S II
II 4-(:+1(CHZ)s
CI S HH4-Bu-tMeC)
ICICHHz CI OHtl
4-CIMeCIICICHt
cl OHIt 4-1MeCHBrC1lz
CI OHIt 4-CI
MeCHBrCIl* CI O
Hl(44MezCCIC(Me)*C
IOHII 4-CIMevCCIC(Me
)z CI OHH4-IMezCB
rC(Me)x C1OHH4-C1RA
XR'R”Y MetCBrC(Me)z cl O
HII 4-IMeCIICICIl(lit)
CI OHIf 4-CIMeC
IICICll(Et) CI OI
t H4-IMeCIl[1rC1l([iL)
CI OHII 4-CIMeC
IIBrCll(Et) CI OH
It 4-IMeCIICICII(Pr)
CI OIt H4-CIMeCII
CICII(Pr) CI Otl
H4-IMeCIIBrCII(Pr)
CI OII It 4-CIMeC
)IBrCII(Pr) C1OIf
H4-IMeCIICICII (Pr-i)
CI OHH4-C1 ecIIcIcIl (
Pr-i) C1OII If 4
-IMeCIIBrCII(Pr-i) C
I OHH4-CIMeCIIBrCll(Pr-
i) CI OHII 4-IMe
CllCICll(Bu) CIO
II H4-(:IMeCIICICtl(Bu)
CI OHII 4-1-ac
IIBrclI(Bu) C1Otl
II 4-CIMeCIIBrCH(Bu)
CI Ofl If 4-TM
eCHCICH(Pen) CI OI
t II 4-CIMeCHCICll(Pe
n) CI OIf II 4
-IMeCIIBrCII(Pen) C
I Oll II 4-CIMeCIIB
rCII(Pen) CI OIt
II 4-IMexCCICllz
CI OII tl 4-CIMe
gCCICHt ct OIf
H4-BrMevCCICHt
Br OII If 4-CIMetCC
ICIlx Dr OII
H4-IMezCCICIIz r
OIf II 4-CIMetCCIC
Ilx I OII It
4-rMexCCICllt
CI OHII 2.4-ClzMet4-C
1z* Pr-10II II
4-CIMexCCICllx
SPr OII H4-CIMegCCICH
t Br OOMe If
4-CIMezCCIClli CI
OHII 4-Bu-LMexCCICll
i CI OII H3-O
BuMexCC3-0Bu CI
OII It 4-FllezccIcIl
t CI S It H
4-CIMexCCICHx cl
S II If 4-Bu-tRAX
R'R'Y MetCCICL cl S H
If 4-OCIltCII=4-0CIltCI
I=CHCI Otl tl 4-CIMe
zCBrCHz CI OHH4
-BrMezCBrCHz Br
OHH4-CIRAXR'l? "Y RAXR'R" Y l (CHtyo) 6 CI O
II H4-C11(CHz)i
CI OII It 4-Tor(C
llx) * CI OHIf
4-CIOr(C1h)s CI
OIt H4-11(C1lt)s
C1OIt 11 4-C11(CH
J* CI OII II
4-1ELCHCICII□C
I OII II 4-CIEtCHCI
CII□ CI O)l II
4-11itcIIBrcHz
CI OHIt 4-CIEtCII[1r
CIlz C1OII If
4-1i-PrCCI(Et)CHz C
1OII H4-CIi-PrCCI(Et)Ct
h cl OHH4-[1ri-PrC
Cl(Et)Cllt cl OII
It 4-1i-PrCCI(Et)Cllt
ar OIt If 4-C
Ii-PrCC1(Et)CHz Br
OHII 4-Ti-PrCCI(Bt)C1l
z I OHtl 4-CIi-
PrCCI(Et)C1lx [OH114
4i-PrCCI(Et)CHg CI
OHIt 2,4-C1zi-PrCCI(Et)
Cut OMe OHH4-Bri-Pr
CCI(Et)CHz 5O2Pr OHH
4-CIi-PrCCI(Et)CHx CI
OIt H4-OPri-PrCCI(Et)
C1lx cl OHII 4-C
FIi-PrCCI(Et)C1lt cl
OHH2,4,55-Cl5i-PrCC1(EL
) C11CI S HH4-CIi-PrCC
1(Et)CHz CI S HH4
-5iMesi-PrCBr(Et)4-5i
CI OHII 4-CIi-PrCBr
(EL) Cllx C1OHH4-Bri-P
rCBr(Et)C1li CI OHH
4-1i-PrCBr(Et)Cut Dr
OHH4-CIi-PrCBr(Et)CHg1
0 It H4-CIi-PrCBr(E
t) CHt HOHH4-CIi-PrCBr
(Et)CHt II OHH4-1
i-PrCBr(EL)CH,CI OHH2,4
-CHgRAXll'R”Y i-PrCBr(EL)C1lt CI
OIf It 2-P, 4-C11-1'rCB
r(Et)C1lt CI S HH
4-CIEtCCl(Me)C1li CI
OHH4-C1RAXR'l? ”Y EtCCl(Me)CHg cl O
II II 2.4-Ft [! tccl(Me
)CHg CI S HH4-C
IEtCCl(Me)CHz CI
S II It 4-Bu-tEtCCI
(Me)Cllt CI S )
I II 4-MeEtCCI(Me)C1l
t CI S It II
4-OPrEt4-0PrEtCCI (CI
S II H4-CHx-(C61hCh-2
+ 4) ELCCI(Me)CIltCI
S Htl 4-COC&l14CI-4'E
tCCI(Me)CHx CI S
HH4-OCII4-0CII (*OEtEtCB
r(Me)C1lt CI OHl(
4-CIEtCBr(Me)CllzC
I OHH4-Br[itCBr(Me)CIlz
CI OIt If 4-
1EtC4-1EtCBr(CI OIf It
2,4-ChEtCBr(Me)Cllt
Br OII If 4-CIE
tCBr(Me)C1lt Br O
HH4-1EtC4-1EtCBr(I OIf
It 4-CIEtCBr(Me)CIlt
IOIt H4-11Et
4-11EtCIlr(F Otl II
4-CIEtCBr(Me)Cl1g
Me OII H4-CIELCBr(Me)
Cl1g OMe OIt It
4-CIRtCBr(Me)C11g
SMe OIf H4-CI[itCBr(M
e) CIlz CI OHMe 4
-CI[tCBr(Me)CIltBr
OHMe 4-CIIEtCBr(Me)C
1lt CI OHIt 3-C
FsHL(Jlr(Me)CHx CI
OIt It 4-PhEtCBr(Me
)CHz cl OHIt 4-
OCHxC4-0CHxCFsEtCBr(CI
OHII 2,6-ChEtCBr(Me)CIl
t CI S It II
4-CIEtCBr(Me)C1lz
CI S H It 4-Bu-LEtCB
r(Me)CHx cl S H
H4-OC+JIz+EtCBr(Me)CHz
CIS It H4-CillJ-
4'EtCBr(Me)C1lx CI
S 11 It 4-CTo-(CJs
Ch-3,5) [1ttCCIC1lx CI
OHII 4-CIEhCCICIlz
CI OHH4-OrEhCCICHt
CI Otl H4-1RA
XR'R”Y EtxCCICII□ CI OI
f If 2.4-CIiEL, CClCl1
．． Br OIt H4-C
IELxCCICIIz Br
OIt 1+ 4-1EttCCICIIt
IOII 8 4-C
IEtzCCICHZ I O
HH4-rIEttCCICIIt
FOIt H4-CIEhCCICIh
Me OIf II 4
-CIEtzCCICIlz OMe
OHH4-CI[! tgccIcllx
OMe OII If 44E
LgCCICIIx SMe O
If H4-CI[1LtCCICIIt
CI OIt It 4-OC
I@II! IEt*CCICIIt
5OJe OIt It 4-CIEbCCI
CIIz CI OIf M
e 4-CIEttCCIllz
CI OCI H4-CIEhCCICHz
FOIt It
4-1EtzCCICIIi SMe
OHH2,4-C1zεtzccIcHg
I OIt Me 4-CI
[! hccIclI* CI OI
t H4-CJIaCI-4'EtzCCICII□
CI OII H4-CNE
hCCICHz CI OHH4
-OCH*CIIg-NHCOOEt EtxCCICIIx CI S
If H4-CIEtgCCICllt
CI S HH4-Bu-tE
tzCCICHZ CI S
If H4-HexELgCCIClli
CI S II II 4-
QC(Me)xcIlgOPrEtgCCICIli
CI S If H4-
OCII□C! I=C)rIEttCCICIIt
CI S If H4-C
HzCIIzPhELxCBrCIlz
CI OIt 11 4-CIEhC[
1rC1lz C1OHH4-BrE
tzCBrCHt CI OIt
H4-1fitg4-1fit
CI OHH2,4-ClgEttCBrCIIx
Br OIt H4-CI
! ! txCBrCIIt T
OIt H4-CIEbCBrCIIt
If OII If 4-C1
1! tzcBrclh HOHH4-
1[1hCBrCll* F O
If tl 4-CIRAXR'R”Y EtICBrCL Me OIt
H4-CIEtzCBrCIIx
OMe OHl-14-CIEtzCBrCl
lz SMe OHtl 4
-CIEttCBrCHx Me
OHIf 4-BrIEhCBrCllz
CI O011It 4-CIE
tzCBrCllz cl OH
H4-PrEtgCBrClb CI
OHIf 2-CI, 4-FEhCBrCI
Iz CI S HH4-C
IEtzCBrCllz CI
S HII 4-Bu-tEtICBrCIl
ffi CI S
II II 4-(mouth 4)E
ttCBrCHt CI S
HIt 4-OClhCllz-NIICOOE
t t-BuCIICICIIt CI
OHIt 4-CIt-BuCIICICIIt
CI OHII 4-1t-
BuCIICCHt Br OH
II 4-CIt-BuCHCICIlz
IOHII 4-CIt-BuC
IIBrCIIx CI OII
II 4-CIt-BuCIIBrCllz
CI OHIt 4-14-1
EtCIICIC) I (CI Otl II
4-CIEtCIICICH(Me)
CI OII H4-14-1EtCllB
rCH (CI OIf H4-CIEL CII
BrCII(Me) C1OHH4-1E
tc) ICICH(El) CI O
II H4-CIEtCIICICI(Et)
CI OHH4-14-1EtCIIB
rC)I(C1OHII 4-CIEtCllBr
Cl((Et) C1OIt It
44EtC1lCIC1l(Pr)
CI OII H4-CIELCIICICI
I(Pr) CI OII If
4-1EtCHBrCH(Pr)
CI OIt II 4-CIEtCHB
rCH(Pr) CI OHH4-T
i-PrCHClC11g CI
OHH4-CIi-PrCHCICHz
CI O11II 44-1i-PrCII
BrCHCI OIt It 4-CIi-
PrC) IBrCIIz CI OIt
If 4-place CIICIC(Me)z
CI OIf II 4-CIEtC
llCIC(Me)z CI OHH
4-TRAXR'l? ”Y IEtCHBrC(Me)t CI
OIt II 4-CIE tCH Kano C (Ml
L-ri! CI OII If 4
-IEtCCI(Me)C1l(Me)Cl
OIt If 4-CIEtCCI(M
e) CIi (Me) CI OIt l
I4-IEtCBr(Me)C1l(Me)
CI OEl II 4-CIEt
CBr(Me)Cll(Me) CI O
If If 4-ri-PrCIICICII
(Me) CI OHH4-C4-C1
i-PrCIICICH(cl OHH44i-P
rCIl[lrCIl(Me) CI
OIf It 4-C4-C1i-PrCHB
rCIl(CI OIt H4-IL-BuC
CI(Me)CHx C1OIt H4-C
IL-BuCCI(Me)Cilt cl
OII If 4-Brt-BuCCI (
Me) CIlt CI OII H44
L-BuCCI(Me)CIltBr
OII If 4-C1t-Bu-C1t-
BuCCI (Br OII If 4-1
t-Bu4-1t-BuCCl(l OIt
H4-Clt-4-Clt-BuCCI(IO
II H4-1t-Bu4-1t-BuCCl (cl
OII It 2.4-C11L:BuC
Cl(Me)CIltFOII
It4-C1t4-C1t-BuCCI(*
Me OHH4-CIL-BuCCl(Me
) C) It OMe Otl If
4-CIL-BuCCI(Me)C1lt
OMe OII It 4-1t-Bu4-
1t-BuCCl(SMe OII H4-C1
t-Bu-C1t-BuCCI (Out OHH4-
C1t-4-C1t-BuCCI (cl OIf
Me 4-Tt-BuCCI(Me)C1lt
CI OHH4-OCHFz4-0CHF
zt-BuCCI (CI S It If
4-CIL-BuCCI(Me)C)I,
CI S II If 4-But
t-BuCCI(Me)C1lt CI
S HII 3-Met-BuCCI(Me)
CHt CI S If It
4-3Met-BuCCI(Me)Cllt
cl S It It 4-Tt
-BuCCI(Me)CIl, CIS
It H4-5PrRAXR'R”Y t-BuCBr(Me)Cllz CI
OIt II 4-CIt-BuCBr(M
e) CHz CI OHH4-Brt-
BuCBr(Me)CIlt cl O
HII 4-rt-BuCBr(Me)CHz
Br OHII 4-CIL-BuC
Br(Me)CHz Br OIt
If 4-1t-BuCBr (phylum e) C1lt
[OIt It 4-CIt-Bu
CBr(Me)Cllz I OIf
II 4-1t-Bu4-1t-BuCBr
(CIOIt)l 2.4-ChL-
BuCCI(Me)CHz F OH
II 4-CIt-BuCBr(Me)C1lz
Me OHtl 4-CIt-Bu
CBr(Me)C1lz OMe OI
f II 4-CIL-BuCBr(Me)C
1lz OMe OII It
4-1t-Bu4-1t-BuCBr(SMe
OIf H4-CIt-BuCBr(Me)CHz
SMe OHtl 4-rt-B
uCBr(Me)C1lz CI OI
I II 2.4-FIL-BuCBr(Me
)Cllt OBu OII II
4-CIt-BuCBr(Me)Cllt
CI OHEt 4-CIt-BuCB
r(Me)CHz CI OII
It4-Bu-st-BuC[lr(Me)C1
lz CI OII II 3
,4-C1zt-4-C1zt-BuCBr(cl
OHIt 4-OCF34-0CF3t-BuC
Br(CIS If H4-CIL-Bu
CBr(Me)C1lz CI S
It It 4-Bu-tt-BuCBr(
Me) CHz CI S H It
4-Met-BuCBr(Me)C1lz
CI S II II 4-CO
Cyll+st-BuCBr(Me)C1lt
cl S It II 4-SF
3-5 Pht-BuCHCIC (CI OHtl
4-CIt-BuCHCIC(Me)x
CI OHH4-1t4-1t-BuCHBrC
(cl OIt)l 4-CIt-Bu
CII[lrC(Me)x CI OI
I It 4-1PrCHCICIIz
CI OIt If 4-C
IPrCIICCICIlx CI
OIf It 44PrCHBrCIlz
CI OHH4-CIPrCIIB
rCHHz CI OItt
l 4-14-1PrCIICICII (CI
OHII 4-CIPrCIICICII(Me
) CI OII II 4
-11'rC1lBrCII(Me) C1
OIt II 4-CIRAXR'R”Y PrCIIBrCII(Me) CI
OIt H44PrCHCICII(Et)
CI OIt II 4-CI
PrCIICICII([Et) CI
0 11 H4-1PrCllBrCII(
Et) CI OHIf 4-C
IPrCIIBrCll(Et) CI
OHIf 4-1PrCIICICIl(Pr
) CI OII fl 4
-CIPrCIICICII(Pr) C
I OHIf 4-1PrCIIBrC1l(
Pr) CI OII It
4-CIPrCIInrCII(Pr)
CI OIt It 4-1PrCC4
-1PrCCI (C1OII II 4-CI
PrCCI(Me)Cllz CI
OII 11 4-BrPrCCI(Me)C1
lz CI OHIf 4-rP
rCCl(Me)C1lt CI O
If II 2,4-ChPrCCI(Me)C
1lt Br OHIt 4-C
IPrCCI(Me)CIlz Br
OIt H44PrCCI(Me)C1lz
r OHI 4-CIPrCCI(
Me) C1li I OII
H4-rPrCCI(Me)CHxF
OII If 4-ClPrCC-Cl
PrCC-1(Me OIf If 4-C
IPrCCI(Me)Cllt OMe
OHH4-CIPrCCI(Me)CHt
OMe OII II 4-1PrCC
4-1PrCCI (SMe OHII 4-CI
PrCCI(Me)Cllz SMe
OHII 4-1PrCC4-1PrCCI (CI
OHH2-F, 4-ClPrCC-ClPrCC
1 (CI OII If 4-rPrCCI
(Me) CIlj CI OIf
H4-OrPrC4-0rPrCCl (CI OH
II 4-ClPrCC1(Me)C1l*
C1OIf H4-MePrCCI(Me)
CHz CI S If If
4-Bu-tRAXR'R”Y PrCBr(Me)CIlx CI
OHH4-TPrCBr(Me)CHg
Br OHtl 44PrCBr(Me)C)
It I OII H4-CI
PrCBr(Me)CHtIO
H)+4-Tr'rcBr(Me)CIlz
F OHIf 4-CIPrCB
r(Me) C1lt Me OIt
It4-CIPrCBr(Me)C1lt
OMe OII ■ 4-CIPr
CBr(Me)CIlx OMe OH
H44PrCBr(Ms)CHx SMe
OHH4-CIPrCBr(Me)C1lt
SMe OHH44PrCBr(Me)CH
t SO*Me OHIt 4-CI
PrCBr(Me)C1lt C1OII
Me4-CIPrCBr(Me)C1lz
CI OCI H4-CIPrC
Br(Me)Cl1g Pr Otl
H4-CIPrCBr(Me)CIlg
SEtOHII 4-IPrCBr(M
e) C1 (* Br OCI H4
-CIPrCBr(Me)C1lt CI
OH113-CIPrCBr(Me)CHx
C1OHH2,3,4,5,6-FsPrC
Br(Me)C1lz CI OHI
t 4-011e4-011exPrCBr(C1
OHH2,6-CHg, 4-FPrCIlr(Me)C
H-rich CI S HH4-CIPrCBr(Me
)CHt CI S HH4-B
u-tPrCBr(Me)CHx CI
S HH4-4-0(CHgOMePrCBr
(Me)CHg CI SHH
4-OCIlzCJlaCFs-4'PrCBr(Me
)CHg CI S HII
4-EtPrCBr(Me)CHgC
I S II II 4-C(Me)*
CIIzOHPrCBr(Me)CHg
CI S EI H4-COCJl+qRA
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C1OII C1bC)lzO-Q17■e
zcyo clI cl OIf
CIIzC1lzOPhMezC=CII
C1Otl CHtCH=N
OPr gate e2c=clI cl
OII CtlzCIIJIICOtEtR
AXR' J MeC(Et)=CII CI
OItCIlzCIlCl1zCIl=NO
Pr □CII CI OIt
CIItCHzOPhMeC(Pr)=C1l
CI OII CII
zCIl=NOPr eC(Pr)=C1l
Br OIt C
IIzCllgO-ro17MeCII=C(Me)CI
l* HOIf CIIzCII
zOPhRAXR' J MezC(OMe)C1lz cl
OIf CIlzCIIzSPhMCllzC
IIzSPh Br OII
CIIzCII=NOPrMezC(OEt)C1lz
CI O)l CIlzCI
lzON=CIIMCl1zCIlzON=CII
CI OIt C1l, Cl1z
OPh Q1 to Q in Tables 1, 2 and 3 above
56 is a group represented by the following structural formula. Next, specific examples will be presented regarding the method for producing the compounds of the present invention.
However, the present invention is not limited to these.
It's not. 1 Eidoku 5-(4-t-butylbenzylthio)-4-chloro-2
-((2,2-dichloro-1,1-dimethyl)-ethyl
)-3(2+1)-Synthesis of pyridazinone [Compound of the present invention
Synthesis of Nα2] 4.5-dichloro-2-((2,2-dichloro-1,1
-dimethyl)-ethyl)-3(2n)-pyridazinone 0
．． 73g, 4-t-butylbenzylmercaptan 0,4
Dissolve 5 g in 10 ml of methanol, add sodium carbonate
0.27 g was suspended. After stirring at room temperature for 3 hours
, pour the solution into ice water, separate it by filtration, and store the obtained crystals in a vent.
Recrystallization from zene-hexane yielded 0.8 g of the desired product. Melt
Point 162-163℃ Production penetration 4-bromo-5-(4-chloro-benzyloxy)
-2-((2,3-dichloro-2-methyl)-propyl
)-3(211)-Synthesis of pyridazinone [Compound of the present invention
Synthesis of No. 12] 4.5-dibromo-2-((2,3-dichloro-2-methane)
(propyl)-3(2+1)-pyridazinone 1.
90g, 4-chlorobenzyl alcohol 0.71g
, dissolved in 10mf of N-dimethylformamide and diluted with hydroxyl
Suspend 0.33 g of potassium chloride powder and stir overnight at room temperature.
did. The solution was poured into ice water, extracted with benzene, and saturated
After washing with brine and then water, the solvent was distilled off under reduced pressure to obtain
The oily substance obtained was subjected to column chromatography (silica gel column chromatography).
Separate and purify with 1.10 g of target product
Obtained. Melting point 1- L-2 ~ 114'C 1 blood ■1 2- (3'-bromopropyl)-4-chloro-5-(
4'-chlorobenzyloxy) -3(2H) -
Synthesis of pyridazinone [Synthesis of the present compound 19] 4.5-dichloro-2-(3'-hydroxypropyl
)-3(211)-pyridazinone 22.3g (0°1 mo
), 19.6 g (0.35 mol) of potassium hydroxide in water
150III! ! , and a mixed solution of 150 mf of ethanol.
The mixture was added to the medium and heated under reflux for about 10 hours. After the reaction, evaporate under reduced pressure.
Tanol was removed, water was added, and insoluble matter was filtered. Dilute the filtrate
Acidify with hydrochloric acid, remove the resulting crystals by filtration, wash with water, and dry.
and 4-chloro-5-hydroxy-2-(3'-hydro
xypropyl) -3(2n)-pyridazinone 14.5
I got g. 4-chloro-5-hydroxy-2-(3'-hydroxy
cypropyl) -3(2+1)-pyridazinone 10.2
g (0.05 mol), 4-chlorobenzyl chloride 8
．． 4 g (0,052 mol) and 1 anhydrous potassium carbonate
0.4 g (0,075 mol) of N,N-dimethylphos
Lumamide 150 Sho 2 plus about 100-120'C
Heated for 3 hours. After the reaction, pour into water and extract with ethyl acetate.
After washing with water and 5% sodium hydroxide aqueous solution, saturated salt
Washed with water. After drying with anhydrous sodium sulfate, remove the solution under reduced pressure.
The medium was distilled off. The obtained solid was washed with n-hexane,
Dry, 4-chloro-5-(4'-chlorobenzyl)
xy)-2-(3'-hydroxypropyl)-3(2
11) -12.3 g of -pyridazinone was obtained. 4-chloro-5-(4'-chlorobenzyloxy)-
2-(3'-hydroxypropyl)-3(2+1)
- 9.9 g (0.03 mol) of pyridazinone was added to chloroform.
Add thionyl bromide to 170 mff1 at -5 to 5°C.
Slowly add 9.4 g (0,045 mol) for about 2 hours.
Stir for a while. After the reaction, add water little by little to remove the chloroform layer.
The liquid was separated. Wash with water and then with 5% sodium bicarbonate aqueous solution.
After further washing with saturated saline, wash with anhydrous sodium sulfate.
Dry. The solid obtained by distilling off the solvent under reduced pressure was
Crystallization with a mixed solvent of sulfur and benzene to obtain white crystals
Compound 2- (3'-bromopropyl)-4-chloro-
5-(4'-chlorobenzyloxy)-3(2H)-
5.2 g of pyridazinone (melting point 83-87°C) was obtained. Engineering】■Soil 4-chloro-2-((2-chloro-2-methyl)-pen
)-5-(4-iodobenzyloxy)-3(2+
1) Synthesis of -pyridazinone [Synthesis of present invention compound No. 33] 4.5-dichloro-2-[(2-chloro-2-methyl)
-pentyl)-3(2+1)-pyridazinone 1.42g
Example of manufacturing 1.17 g of 4-iodobenzyl alcohol
1.72 g of the target product was obtained in the same manner as in 2. Melting point 114
~115°C 4-chloro-2-((2,3-dichloro-2-methyl)
-propyl)-5-((2-iodo-5-pyridyl)-
Synthesis of 4.5-dichloro-2-((2,3-dichloro-2-methoxy)-3(2+1)-pyridazinone [Synthesis of present compound No. 202]
(propyl)-3(2+1)-pyridazinone 1.
45g, 2-iodo-5-pyridinemethanol 1,18
1.33 g of the target product was obtained by the same operation as in Production Example 2. Melting point 117-120'C (hereinafter referred to as blank space) Production plate 1 4-chloro-2-(2-chloro-2-methyl
2-(2-chloro-2-methylpropyl)-4,5-
1.85 g of dichloro-3(2H)-pyridazinone and
and 2-phenoxyethanol1. OOg to N, N-di
Powdered potassium hydroxide dissolved in 10mf of methylformamide
0.48 g of aluminum was added thereto, and the mixture was stirred at room temperature overnight. Implemented below
By the same operation as in Example 2, 1.9g of the target material was obtained. Melting point 82
-83℃ 1LiaL Medical Engineering 5-(4-t-butyl-α-methylbenzene)
2-(2-bromoethyl)-4,5-dichloro-3(2-bromoethyl)-4,5-dichloro-3(
2.7 g of 2H)-pyridazinone and 4-t-butyl-
1.8 g of α-methyl-benzyl alcohol was added to N,N-di
Methylformamide 60n/! Nitokaji. Furthermore, add 1.4 g of powdered potassium hydroxide and leave at room temperature.
Stir overnight. After the reaction, it was poured into water and subjected to Hensen's extraction. ben
The Zen layer was washed with water, dried over anhydrous sodium sulfate, and then dried under reduced pressure.
The solvent was distilled off. Column chromatography of viscous liquid with residual aroma
(silica gel: benzene-ethyl acetate)
2.2 g of the target compound was obtained. Viscous liquid 'H-NMR (CDC/!!, δ+ ppm) 1.37
(9H,s), 1.80(311,d, J=611z
). 4.95 (IH, d, J=911z), 5.66 (I
H, q, J = 611z). 5.67 (LH, d, J=1511z), 7.17
~7.53 (411, m). 7.68 (IH, d, d, J=911z, 1511z)
, 7.78 (III, s) Production ■D 4-chloro-2
-(2-chloro-2-methylpentyl)-5-(4-ethyl)
Synthesis of 2-(2-chloro-2-methylpentyl)-4,5-
Dichloro-3(2H)-pyridazinone 1.2g and 4
- 0.64 g of ethylbenzyl alcohol
Dissolve in 20mf of chillformamide. Add 0.31 g of powdered potassium hydroxide onto a water-cooled top and bring to room temperature.
The mixture was stirred for 1 day. The purpose is as follows by the same operation as in Example 2.
600 mg of the compound was obtained. Melting point: 81-83°C
4-chloro-2-(2-chloro-2-methylpentyl
)-5-(4-)lifluoromethylbenzyloxy)-3(21+)-pyri
Synthesis of dazinone (synthesis of the present compound Nα56) 2-(2-chloro-2-methylpentyl) -4,5-
Dichloro-3(2H)-pyridazinone 1.2g and 4
-Trifluoromethylbenzyl alcohol 0.78 g
20mj of N,N-dimethylformamide! dissolved in
Add 1.46 g of anhydrous potassium carbonate and heat at 50°C for 8 hours.
Stirred. The target compound 1 was obtained using the same procedure as in Example 2.
．． Obtained 0g. Melting point 105-106°C manufacturing base 4-
Chloro-2-(2-chloro-2-methylpropyl)-5
-((2-iodo-5-pyridyl)-methoxy]-3(2H)-pyridazinone and 4-chloro-5-((2-iodo-5-pyridyl)-methoxy)-2-(2-methyl-1 -propenyl)-3(2H)-Synthesis of pyridazinone [Synthesis of compounds of the present invention Nα237 and Nα255] 2-(2-chloro-2-methylpropyl)-4,5-
Dichloro-3(2H)-pyridazinone 1.4g and 2
-Iodo-5-pyridylmethanol 1.29g N,N
- dimethylformamide and water-cooled powdered potassium hydroxide 0. Add 3 3 g
The mixture was stirred at room temperature for 1 day. The following operations are similar to those in Example 2.
4-chloro-2-(2-chloro-2-methylpropyl
)-5-((2-iodo-5-pyridyl)-methoxy)
-3 (2H)-pyridazinone 0.74 g (melting point 119
~123 °C) and 4-chloro-5-((2-iodo
-5-pyridyl)methoxy)-2-(2-methyl-l
-propenyl)-3 (2H)-pyridazinone 0.24
g (melting point 141-142'C) was obtained. 1 armor ± and 2 (2-chloro-2-methylpropyl)
-Synthesis of -5-(4-iodobenzyloxy)-4-methyl-3(2H)-pyridazinone [Synthesis of the present compound Na, 167] 5-chloro-2-(2-chloro-2-methylpropyl)
-4-Methyl-3(2H)-pyridazinone 0.33gb
and 0.33 g of 4-iodobenzyl alcohol with N,
Dissolve in 5 ml of N-dimethylformamide and cool with water.
Add 0.1 g of powdered potassium hydroxide and proceed as in Example 2.
0.3 g of the target product was obtained by the following operations. Melting point 121-12
3°C Next flame ■ 4,5-dichloro-2-(3-chloro-tetate)
lahydro-2-pyranyl)-3(211)-pyridazi
Synthesis of Non 2.4.5-Trichloro-3(2H)-pyridazinone 4
g of methylene chloride 20+/! Dissolve in water and cool under water. 2.5 g of 2.3-dihydro-bilane was added dropwise. 30 minutes
After stirring, the by-produced 4,5-dichloro-3(28)-pyri
Dazinone was filtered off, and the filtrate was distilled off under reduced pressure. The obtained oil was subjected to column chromatography (silicage gel).
(benzene), and the first fraction is the trans form.
1.5 g (melting point 136-137°C). As the second fraction, 1.3 g of cis isomer (melting point 109-110'
C) Obtained. 'HNMR (CDC1z, δ, TMS) trans form
1.50-2.20 (m, 411), 3.50-4
．． 60 (n+, 311), 5.86 (d, III, 1
011z), 7.77 (s, LH) Cis body 1.9 (1-2.50 (m, 411L
3.50-4.60 (m, 311), 6.05 (d
, III, 311z), 7.83<s, 111) 4,5-dichloro-2-(2,3-dichloro
-2-propenyl)-3(2H)-pyridazinone synthesis 4.5-dichloro-3(2H)-pyridazinone 10,8
g and 9.5 g of anhydrous potassium carbonate to
Add formamide 65112 and stir at room temperature for 10 minutes.
did. Then 1.2.3-trichloro-1-propene (
Add 10.0g (mixture of 8 bodies and 2 bodies) and heat at 40°C for 6 hours.
After stirring for a while, pour into a large amount of water. Extract with benzene and remove the solvent under reduced pressure to obtain the target compound.
6.0 g (mixture of 8 bodies and 2 bodies) was obtained. Column this
Melting point 9 by chromatography (silica gel, benzene)
3.7~94.6°C, 112,8~114.8°C
The isomers were separated. 'H-N M R (CDCl 3.δ, TMS) isomerism
Body 1 (melting point 93.7-94.6°C): 5.15 (s
, 211), 6.47(s, IH). 7.84 (s, 1ll) Isomer 2 (melting point 112.8-114.8°C): 5.00
(s, 211), 6.70 (s, IH). 7.84 (s, 1ll) Production characteristics ■ 4,5-dichloro-2-(2-methyl-2-
Synthesis of propenyl)-3(2H)-pyridazinone 4. 10 g of 5-dichloro-3(2H)-pyridazinone,
27 g of 3-chloro-2-medylbropene and potassium carbonate
8.4 g of aluminum was suspended in N,N-dimethylformamide.
The mixture was stirred at 40°C for 5 hours. Thereafter, 4.9 g of the target product was obtained in the same manner as in Example 2. Melting point: 52-54°C 1:2 (2-chloro-2-methylpropyl)
Synthesis of -4,5-dichloro-3(2H)-pyridazinone
4.5-dichloro-2-(2-methyl-2-propenyl
)-3(2H)-pyridazinone 5g and trioc chloride
0.1 g of methylammonium to 100 g of carbon tetrachloride
nf! Add 30ml of concentrated hydrochloric acid and leave at room temperature for 3 days.
Stirred. The organic layer was separated, washed with water, and diluted with anhydrous sulfuric acid 1-1,
After drying at 1 um, the solvent was distilled off under reduced pressure to obtain 4.7 g of the target product.
Obtained. Melting point 61-66°C Production Example 1 to Production Example 11
Compounds actually produced according to any of the methods shown
The physical properties are shown in Tables 4, 5 and 6. [However, 2
In the table. Me is a methyl group, Et is an ethyl group, Pr is a pro
Bu stands for butyl group, Pen stands for pentyl group.
,, l1ex is hexyl group, Ph is unsubstituted phenyl
group, t is tertiary, S is secondary, i is
C represents iso, and C represents cyclo. ] The numbers of the compounds in Tables 4, 5 and 6 are as follows. Referenced in manufacturing examples, formulation examples, and test examples. (Hereafter, blank space) Table 4 No. RA XR'R" Y
Melting point (°C) No, RA XR'R" Y
Melting point ('C) No, RA XR'R
” Y Melting point (°C) 86 PrCC
I(Me)C1lx CI OII H3-
0\105-106CH No, RA XR'R" Y
Melting point (°C) No, RA XR'R"
Y Melting point (C) (below, margin) No, RA XR'R” Y
Melting point (°C) +30 CIl, CII
CI OII H3-F
10841913I CIl□・CII
CI OII H4-CI
151-153132 CIl□・CII
CI OII II 4-CF3
175-177133 CIl□・C
II CI O)l II 4
-Ph 189-191 (CJ14F-
4) 13G Cl12=CIICII2
CI S H If 4-But
131-1341.37 C1l□, ClICl1.
C1OII II 4-CI
74-77 (C, lI, Cl-4) NOMaCIl=CIIC1lz cl
OII H4-Me 101-102
141 MeCII=CIICI1.
CI OII II 4-Pr-+
118-119142 MeCII=CIICl
lz cl OII If 4-Bu
-L 112-114143 MeCI
I=CIIC11, C1OII H4-F
132-133+44 MeCIl=C1l
CIlz cl OII II 'L
CI 118-119145 Me
CII□ClICl1t Cl OHII
3,4-Ch 143-144+46
MeCII=CIICtlz cl O
HII 4-CO-127-136 (C, lI, Cl
-4) 147 lICECC1h cl S
If If 4-flu-t 1
00-102148 11C=CCII□
CI S II II 4-CI
135-140156 Pr(Me>=CI
I Me OII II 4-1
106-108+60 PrCC1(
Gate e) C1lz CI OII H4-O
CFi 84-85No, RA
XR'R'' Y Melting point (°C) (below
, margin) Table 5 O No, RA XR'R” 0
Melting point (°C) No, RA XR'R"
Q Melting point ('C) (N): TL
C (Silica gel: CJ, (10)-C
Il*C00Et(1)) Rfii, 0
．． 15 (Umbrella*): TLC (Silica g
el: CJla(10)-CHzCOOIEt(1
)) Rf value = 0.22 (hereinafter, margin) Table 6 No. RAXR' J Fusing
Point ('C) No, RA χ R' J
Melting point (°C) Tables 4, 5 and above
The definition of Q in Table 1, Table 2 and Table 3 is as follows.
This is the same as the definition of Q in (Hereinafter, blank space) The compounds of the present invention can be used as insecticides, acaricides, nematicides, and animals.
When used as a repellent for living mites, general
A suitable carrier 2, such as clay. Solid carriers such as talc, bentonand, diatomaceous earth, etc. or water
, alcohols (methanol, ethanol, etc.), aromatics
Hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers. Ketone neck, esters (ethyl acetate, etc.), acid amides (
It can be used in combination with a liquid carrier such as dimethylformamide (dimethylformamide, etc.).
Emulsifiers, dispersants, suspending agents can be used as desired.
, penetrants, spreading agents, stabilizers, etc. are added to form emulsions, oils,
It can be used in any dosage form such as wettable powders, 9-grain powders, and flowables.
It can be used for any purpose. In addition, if necessary,
When spraying, other herbicides, various insecticides, fungicides, and plant
It may also be used in combination with length regulators, synergists, etc. invention
The amount of compound to be applied depends on the application situation, application period, application method, and target.
Although there are differences depending on pests, cultivated crops, etc., in general, it is an effective product.
The quantity is approximately 0.005 to 50 kg per hekdale.
is appropriate. Next, the compounding ratios and types of various preparations of the present invention are described below.
I will post it. agent l~2552~953~20 0~20 agent
1~30 70~9907 pull
1~70 10~90 1~
20 0-10 with Japanese additives 1-7015-93
3-10 0-5) Agent 0.01-3
0 67-99.50-3η agent 0.01-306
7-99.5 0-8 Values in the table above are weight%
represents. When used, emulsions, oils, flowables and hydrating agents
For powders and granules, dilute them with a specified amount of water and spray.
Spray directly without diluting. In addition,
Granules also include bait agents. Next, examples of each component in each of the above formulations are given. ■ Active ingredient: Compound of the present invention Carrier: xylene, dimethylformamide, methylnaf
Talene, cyclohexanone, dichlorobenzene, isophoric
Ron surfactant: Tsurupol 2680, Tsurupol 300
5X Trupol 3353 Other ingredients: piperonyl ptoxide, benzotri
Amount of azole active ingredient Carrier of the compound of the present invention: xylene, methyl cellosolve, kerosene (hereinafter referred to as
, margin) Flowable active ingredient z Compound carrier of the present invention: Water surfactant: Lunox 100OC, Tsurpol 33
53, Sobrofer PL, Nippol, Agrisol S-710, sodium lignin sulfonate and other ingredients: xanthan gum, formalin, ethylene
Recall, propylene glycol aqueous phase M Active ingredients: Compound of the present invention Carrier: Calcium carbonate, kaolinite, siecrite
D, Zikrite PFP, diatomaceous earth, talc surfactant: Tsurupol 5039, Lunox 100
0C. Calcium lignin sulfonate, sodium dodecylbenzenesulfonate Tsurupol 5050, Tsurupol 005D. Tsurupol 5029-0 Other ingredients: Carbrex #80 ■Active ingredients: Compound of the present invention Carrier: Calcium carbonate, kaolinite, Siegrite
D. Talc and other ingredients diisopropyl phosphate, carpre
Box #80 Grain layer (1) Amount of active ingredient Compound carrier of the present invention: Calcium carbonate, kaolinite, bentonite
, talc and other ingredients: calcium lignin sulfonate, poly
1 sip of vinyl alcohol 1 (2) (Bait agent j Active ingredient: Compound of the present invention Carrier: Flour, wheat bran, corn grid, Zicra
Item D Other ingredients: paraffin, soybean oil, and insecticides and acaricides containing the compound of the present invention as active ingredients. Examples of formulations for nematocides and insecticides that kill mites that parasitize animals.
However, it is not limited to these. In addition, the following
In the formulation examples below, "parts" mean parts by weight. a Emulsion compound of the present invention -------5 parts
Silene -------70 parts N
, N-dimethylformamide---20 parts
Paul 2680 ---------- 5 parts (non-
Mixing of ionic surfactants and anionic surfactants
Product: Toho Chemical Industry ■Product name) Mix the above ingredients uniformly to make an emulsion.
shall be. When using, increase the above emulsion by 50 to 20,000 times.
The amount of active ingredient when diluted to 0.005~
Spread it to a total weight of 50 kg. 1"1"D Wettable powder Compound of the present invention ------- 25 parts
Sieglite P P P ---------------------
66 parts (mixture of kaolinite and sericite; Zeeklite Industries ■trade name) Tsurupol 5039 ------- 4 parts (
Anionic surfactant: Toho Chemical Industry ■Product name) Carplex #80 -------- 3 parts (
White carbon: Shionogi & Co., Ltd. ■Product name) Ligninsul
Calcium phonate------ 2 parts or more mixed uniformly
Grind and use as a hydrating agent. When using, dilute the above hydrating agent 50 to 20,000 times.
The amount of active ingredient is 0.005~50k per hekdale.
Spread it so that it becomes g. ■■ Oil agent Compound of the present invention ------10 parts
Methyl cellosolve -------90 parts
Mix the above ingredients uniformly to make an oil agent. When using the above oil
The amount of active ingredient is o, oos ~ 50k per hekdale.
Spread it so that it becomes g. ■Powder Compound of the present invention ------3.0 parts
Carplex #80 -------0.5 parts
(White carbon: Shionogi & Co., Ltd. ■Product name) Clay
-------95 parts diisopropylene phosphate
Lopil ------- Mix 1.5 parts or more evenly.
Combine and crush to make powder. When using the above powder,
The amount will be 0.005 to 50 kg per hekdale.
Spray on sea urchins. Wantsake Granule Compound of the Invention ------5 parts Ben
Tonite -------54 parts talc
--------40 parts lignin
Calcium sulfonate---1 part or more evenly
Mix and grind, add a small amount of water, stir and mix, and extrude granulation.
Granulate it in a machine and dry it to make granules. When using the above particles
The active ingredient amount is 0.005 to 50k per hekdale.
Spread it so that it becomes g. Birth of jLM - Flowable agent Compound of the present invention - Heh - 35 parts
Paul 3353 ------- 10 copies (non-
Ionic surfactant: Toho Chemical Industry ■Product name) Runonku
100OC---0.5 parts (anionic surfactant)
Sex agent: Toho Chemical Industry ■Product name) 1% xanthan gum aqueous solution
----------20 parts (natural polymer) Water ----------
34.5 parts The above ingredients excluding the active ingredient (the compound of the present invention)
Uniformly dissolve, then add the compound of the present invention and stir well.
After that, wet grinding is performed in a sand mill to obtain a flowable agent.
. When using, add the above flowable agent to 50 to 2000
The amount of active ingredient when diluted to 0 times is 0.00 per Hekdale.
Spread it to a weight of 5 to 50 kg. (Hereinafter, blank space) Next, the usefulness of the compound of the present invention as a pest control agent is as follows.
This will be specifically explained in the test example. Insecticide test specification against black leafhopper
5χ emulsion of the described compounds of the present invention (depending on the compound)
25χ hydrating agent sample) was diluted with water containing a spreading agent,
The drug solution was adjusted to a concentration of 500 ppm. Rice plants planted with this chemical solution in 1/20,000 are pots
After spraying a sufficient amount on the leaves and leaves, and after air-drying,
Black leafhopper showing resistance to carbamate insecticides
20 2nd instar larvae of rice were released per pot, and
It was covered with a cylindrical cage made of wire mesh and stored in a constant temperature room. The survey was conducted 30 days later, and each rice plant was found to be infected.
We investigated the number of parasites (number of surviving insects) of leafhoppers and
The insect mortality rate was calculated using the following formula. The test was conducted in two replicates per section. As a result, the following compounds are highly effective with a 100% insect mortality rate.
showed that. Compound No. of the present invention: 9.10.12.15.1
7, 19.24.25.27.28.32.33.38
．． 39.45.49.50.52.53.75.76.
77.78.80.81.85.87.92.97.1
04.105.107.108.109.110.11
11112.113.114.115.116.117
．． 118.120.122.124.125.126.
127.155.156.201.202.203.2
04.206.207.208.209.211.21
2.218.219.226.228.229.230
．． 231.234.236.237.238.239.
240,244.245.247.250.251.3
14.321.324.325 (Hereinafter, blank) Insecticidal test against brown planthopper Organophosphorus system
Tumors that are resistant to insecticides and carbamate insecticides
Instead of the 2nd instar larva of the black leafhopper, the larva of the brown planthopper
The test was carried out in the same manner as Test Example 1 except that 2nd instar larvae were used. As a result, the following compounds are highly effective with a 100% mortality rate.
showed that. Compound No. of the present invention: 11.25.34.48.93.
201,202.203.204.205.207.2
0.8.209.211.212.214.215.2
19.228.229.230.231.234.23
6.237.238.239.240.243.244
．． 245.246.247.249.250,? 51.
254.255.256.257.259.263.2
64.265.271.302 (hereinafter referred to as blank space)
5x emulsion of the compound of the present invention (25x emulsion depending on the compound)
Wettable powder or 20% oil solution) in a transparent spitch tube.
Add acetone to the solution to a concentration of 500 ppn+.
A setone solution was obtained. Put 10cc of this acetone solution into a Petri dish with a diameter of 9cm.
Add to 10g of wheat flour, stir, and add acetone.
was removed. And in this petri dish, there is
Ten male and female adults were released and stored in a constant temperature room. The survey was conducted after 90 days and the number of adult insects that appeared in the next generation and beyond was observed.
I guessed it. The test was conducted in two replicates per section. As a result, the following compounds are completely absorbed by newly emerged adults.
It was not recognized very well. Compound No. of the present invention: 9.10.12.15.1
9.24.25.32.33.39.70.71.75
．． 76.77.78.79.80.81.84.85.
86.87.92.93.94.95.97.100,
101.102.103, 104, 105, 106, 1
07.108, 109, 110, 111, 112.11
3, 114, 115, 116, 117.118, 119
, 120, 121, 122.123, 124, 125,
126, 127.155, 156, 159, 160, 1
61.163, 164, 168, 169, 173.20
1.202.203, 204.206.207.208
．． 209.211212.226.227.228.2
29.230.231, 232, 234, 235.23
6.237.238.239.240, 241.242
．． 243.244.245.246.247.248.
249, 250.251.255.257.263.2
64, 266, (hereinafter in the margin) "μ3L example" recorded in the insecticidal test specification against Culex Culex.
5x emulsion of the compound of the present invention (depending on the compound, 2x emulsion)
5χ hydrating powder or 20% oil solution) was diluted with water.
A chemical solution with a concentration of 10 ppm was prepared. Place this chemical solution in a waist-high petri dish with a diameter of 9 cm and a height of 6 cm.
Pour 200ml and release 10 Culex Culex final instar larvae.
Ta. Store this waist-high petri dish in a constant temperature room at 25°C.
After 7 days, the number of adults that emerged was counted. The test was conducted in two replicates per section. As a result, the following compounds are completely absorbed by newly emerged adults.
It was not recognized very well. Compound No. of the present invention: 1.2.3.4.5.6.
9.10.12.14.15.17.18.19.24
．． 25.27.28.30.32.33.34.35.
38.39.45.49.52.53.70.71.7
2.73.75.76.77.78.79.80.81
．． 82.83.84.85.86.87.88.90.
92.93.94.95.96.97.98, 99.1
00.101.102.103.104.105.10
7.108.109.110.111.112.113
．． 114.115, 116, 117, 118.119.
120, 122, 123.124, 125.126,!
27.155, 156.158.160.163, 16
4.168, 169.173.201.202.203
．． 204.205.206.207.208.209.
211.212.215.217.218.219.2
24.225.226.227.228.229.23
0.231.232.233.234.236.237
．． 238.239.240.241242.244.2
45.246.250.251.255.257.26
4.266.301 (Hereinafter, blank space) μ3 support example - Specification of insecticidal test against the striped spotted moth
5x emulsion of the compound of the present invention described in
test 25χ hydrating agent or 20% oil agent) on a transparent screen.
Add acetone to the pitch tube and make it 500ppm concentrated.
An acetone solution was obtained. Put 10cc of this acetone solution into a Petri dish with a diameter of 9cm.
Add to 10g of rice bran, stir, and add acetone.
Distilled away. And in this petri dish, there are striped porcupine moth larvae.
The IO heads were released and stored in a constant temperature room. The investigation will take place in 30 days.
The number of adult insects that appeared was observed. The test was conducted in two replicates per section. As a result, the following compounds are completely absorbed by newly emerged adults.
It was not recognized very well. Compound No. of the present invention: 9.10.11.12.1
5.19.24.25.27.28.32.33.34
．． 38.39.52.53.70.71.73.74.
75.76.77.78.79.80.81.84.8
5.86.87.89.90.92.93.94.95
．． 97.98.100.101, 102.103.10
4.105.106.107.108.109.110
, 111.112.113.114.115.116.
117.118.119, 120.124.125, 1
26.127.155.156.160.162.16
3.164.166.167.168.169.171
．． 172.173.201゜202.203.204.
206.207.208.209.211, 212.2
14.215.217.218.219.225.22
6.227.228.229.230.231.232
．． 233.234.235.236.237.238.
239.240.241.242.243.244.2
45.246.247.249.250.251125
6.257.258.259.260.261262.
263.264.265.266.268.270.2
71.302.314.318.319 Insecticide test specification against peach aphid
5x emulsion of the compound of the present invention described in
252 Permanent Agent) was diluted with water containing a spreading agent.
The chemical solution was adjusted to a concentration of 500 ppm. Place in a 3cm diameter sieve containing filter paper moistened with water.
Insert a disk of orchid leaves and remove the 3rd instar green peach aphid.
Release 5 insects per petri dish, and apply the above medicine from the spray base.
The solution was sprayed and stored in a constant temperature room. The survey was conducted after 7 days, and the number of surviving insects in each petri dish was
was investigated, and the mortality rate was calculated in the same manner as in Test Example 1. Na
Oh, the test was conducted with 4 repetitions per section. As a result, the following compounds are highly effective with a mortality rate of 100%.
showed that. Compound No. of the present invention: 9.10.12.15.2
5.27.28.32.33.34.36.37.38
．． 39.54.55.56.58.59.61.62.
64.75.76.84.85.87.93.95.9
6.97.100, IO Engineering, 102.103.104.
105, 107, 10B, 110, 111, 115.
116, 11B, 119, 120, 123.124,
125, 126, 156, 159.160, 161, 1
63, 164, 165.167, 168, 169, 17
0, 173.201.202.203.204.207
．． 208.209.211.212.215.228.
231.234.244.245.246.247.2
50.251.255.257.259.260.26
1262.264.265.266.268.270.
271.301.302.303.305.306.3
07.310, 314.318.319.320.32
1 (hereinafter, blank) 5χ emulsion of the compound of the present invention (compound
Therefore, a 25χ hydrating agent was tested) with water containing a spreading agent.
The drug solution was diluted to have a concentration of 500 ppm. Soak the Cilantro leaves in this chemical solution, and after air drying, the diameter is 7 CII.
Place the 3rd instar larvae of the diamondback moth in a petri dish.
Ten insects were released and kept in a constant temperature room. The survey was conducted 20 days later, and the number of adult insects that emerged (surviving insects)
The mortality rate was calculated using the same formula as Test Example 1.
. The test was conducted in two replicates per section. As a result, the following compounds are highly effective with a mortality rate of 100%.
showed that. Compound No. of the present invention: 9.10.11.12.1
5.17.19.24.25.27.28.32.33
．． 34.38.39.80.81.85.104.10
5.118.119.124.125.127.155
．． 156.201.202.203.204.206.
207.211.212.214.215.230.2
31.234.236.237.243.244.24
5.246.247.249.250.251.255
．． 256.257.263.264, 265, 271 (Hereinafter, blank) 5χ emulsion of the compound of the present invention (compound
Therefore, test 25z hydrating powder) with water containing a spreading agent.
The drug solution was diluted to have a concentration of 500 ppm. this medicine
Soak 10g of brown rice in a 9cm diameter petri dish in the liquid.
After air-drying, 10 adult male and female brown elephants were released.
, and stored in a constant temperature room. The survey was conducted after 90 days and the number of adult insects that appeared in the next generation and beyond was observed.
I guessed it. The test was conducted in two replicates per section. As a result, the following compounds are completely absorbed by newly emerged adults:
I was not able to admit. Compound No. of the present invention: 24.33.62.85.1
00.104.106.109.115.116.11
B, 119.120.155.160.164.165
．． 168.203.205.206.207.211.
212.228.231.237.239.240.2
43.244.245.246.247.249.25
7.264.266 X Described in the insecticidal test specification against German cockroach
5x emulsion of the compound of the present invention (25x emulsion depending on the compound)
χ hydrating agent or 20% oil solution) was added to transparent spitch.
Weigh and add acetone to the tube to give a concentration of 500ppo+.
An acetone solution was obtained. Put 10cc of this acetone solution into a Petri dish with a diameter of 9cm.
Add acetone to the powdered feed for small animals and stir.
Distilled away. Then, use this Petri dish with a diameter of 20cIIl.
It was placed in a large petri dish and used as bait. And in this large petri dish, 5th instar German cockroach larva l.
The O-heads were grown as adults and stored in a constant temperature room. In addition, use a large Petri dish containing absorbent cotton soaked with water.
I put it inside and gave it water. The investigation was conducted after 60 days, and the number of adult insects that appeared was observed. The test was conducted in two replicates per section. As a result, the following compounds showed no appearance of adult worms.
There wasn't. Compound No. of the present invention: 201.202.203.
204.206.207.211.212.230.2
36.237.239.243.244.245.24
6.247.250.251.257.265.266 Patent applicant Nissan Chemical Industries, Ltd.

Claims (2)

[Claims] (1) General formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [I] [In the formula, R is an alkenyl group with 2 to 16 carbon atoms, 2 carbon atoms
-16 alkynyl group, C3-8 alkyl group substituted with C1-6 alkoxy, or G-Ra-
represents. {G is a hydrogen atom, RbO-, RbS-, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, RbSO_2-, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, RbCO_2- ,▲There are mathematical formulas, chemical formulas, tables, etc.▼, RbNHCO_2-, RbNH-, (Rb
)_2N- or a cyano group. (Rb has 1 or more carbon atoms
4 represents an alkyl group. ) Ra is an alkylene group having 3 to 16 carbon atoms substituted with a halogen atom, an alkenylene group having 2 to 16 carbon atoms substituted with a halogen atom, an alkynylene group having 2 to 16 carbon atoms substituted with a halogen atom, a halogen atom A cycloalkylene group having 3 to 8 carbon atoms substituted with , a cycloalkenylene group having 5 to 8 carbon atoms substituted with a halogen atom, and a cycloalkenylene group having 5 to 8 carbon atoms substituted with a halogen atom
oxacycloalkylene group, thiacycloalkylene group having 5 to 8 carbon atoms substituted with a halogen atom, 3 to 8 carbon atoms
8 cycloalkyl group and an alkylene group having 1 to 4 carbon atoms substituted with a halogen atom, an oxirane group and an alkylene group having 1 to 4 carbon atoms substituted with a halogen atom, an optionally substituted phenyl group, and a halogen atom. Substituted alkylene group having 1 to 4 carbon atoms or optionally substituted heterocyclic group and halogen atom having 1 carbon number
~4 alkylene group. } A is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms; 4 represents an alkylsulfonyl group. R^1 represents a hydrogen atom, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or a hydroxy group. X represents an oxygen atom or a sulfur atom. J is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas , tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Represents. {R^2, Rc, Rd, Re and Rf each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. X^1 represents -O-, -S-, -NH- or -N-. (Rg represents an alkyl group having 1 to 4 carbon atoms.)Hal
represents a halogen atom. } Q represents a substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted heterocyclic group, and Q^1 represents an optionally substituted phenyl group, an optionally substituted naphthyl group, or a substituted represents a good heterocyclic group. ] 3
(2H)-Pyridazinone derivative. (2) An insecticide, acaricide, nematicide, and an agent for killing mites parasitic on animals, which contain as an active ingredient one or more of the 3(2H)-pyridazinone derivatives according to claim (1).