JP2001247539A - Biocidal alkyl-substituted (hetero)aryl-ketoxime-o-ether, and method of producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an alkyl-substituted-(hetero)aryl-ketoxime-O-ether compound represented by a series of general formula (1), an intermediate ketone and oxime compounds represented by a series of general formulas (II) and (III), a method of producing them, and biological activities. SOLUTION: The compound represented by general formula (I) has the excellent biological activities for controlling insects, bacteria and weeds, and especially exhibits high activities in the control of an insect pest in the fields of agriculture, horticulture, cultivation of a flower, and hygiene. The compound represented by general formula (I) has the rapid and sustained insecticidal activities without damaging crops. The compounds represented by general formulas (II) and (III) acting as the intermediates have also considerably good biological activities.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a series of biocidal alkyl-substituted (hetero) aryl-ketoximes.
The present invention relates to O-ethers, intermediate ketones and oxime compounds and methods for producing them.

[0002]

BACKGROUND OF THE INVENTION There is a great deal of national and international literature on the research and application of alkyl-substituted (hetero) aryl-ketoxime-O-ethers as pesticides, some of which are sold as agricultural chemicals. I have. Related literature and patents are as follows: Bull.
M. J. , Davics, J. et al. H. Seele, J .;
G. FIG. Henry, A .; G. FIG. , Pestic. Sc
i. , II, 249 (1980); Paul, Jill.
Helaine et al., European Patent Application 4,75
4, U.S. Patent Application 891,991;
No. 5,864; Kuhn, G .; Zabek et al.
CN 1077709A (DE P 421 149.
9); CN 1059515A; DE 4444230
A; DE 2806664A; Nishioka
JP-A-55-17323, JP-A-54-13
No. 852. The agricultural chemicals are as follows: oxime ether pyrethrum esters (CA registration number N
o. 69043-27-2) and the like. Alkyl-substituted (hetero) aryl-ketoxime-O-ethers have excellent biocidal activity. They have a number of characteristic features, such as a broad spectrum, high efficiency and low toxicity, as well as a biocidal activity of the pyrethram type, for example a rapid killing power. Alkyl-substituted (hetero) aryl-ketoxime-O-ethers can be considered a new type of pesticide and are worthy of extensive development and use. To find a new class of alkyl-substituted (hetero) aryl-ketoxime-O-ether pesticides, the Hunan Chem.
medical and Industrial Rese
arch Institute) has conducted extensive research on compounds of this type and has filed patent applications for some of the new biologically active compounds (Filing no.
98-112666.0). After further study, we have developed a series of novel alkyl-substituted (hetero) with excellent pesticidal properties, especially with excellent pesticidal properties.
Aryl-ketoxime-O-ether compounds have been found.

[0003]

The present invention provides a compound represented by the general formula (I):
And a series of intermediate ketone and oxime compounds of general formulas (II) and (III), respectively.

[0004]

Embedded image

The general formulas (I), (II) and (III)
In: I. Ar1 and Ar2 can be the same or different.
Represents the following groups: (a) (C₆~ C₁₂) Aryl groups or up to 10
A heteroaryl group having carbon atoms, or (b) I.I.
Group defined in (a), described below if necessary
Substituted with up to 5 same or different substituents
: Halogen, nitro group, cyano group, (C₁~ C₆) Al
Kill group, (C₁~ C₆) Halogen-substituted alkyl groups, cyano
-(C ₁~ C₆) Alkyl group, (C₁~ C₆) Alkoxy-
(C₁~ C₆) Alkyl group, (C ₁~ C₆) Alkylthio group
-(C₁~ C₆) Alkyl group, (C₁~ C₆) Alkoxy
Group, (C₁~ C₆) Alkoxy- (C₁~ C₆) Alkoxy
Group, (C₁~ C₆) A halogen-substituted alkoxy group, (C₁~
C₆) A halogen-substituted alkoxy-alkyl group, (C₁~ C
₆) Alkylthio group, (C₁~ C₆) Halogen-substituted alkyl
Luthio group, (C₁~ C ₆) Alkylsulfonyl group, (C₁
~ C₆) Alkyl-sulfinyl group, (C₁~ C ₆) Al
Coxy-carbonyl group, (C₁~ C₆) Alkylamino
Group, 2- (C₁~ C ₆) Alkylamino group, linear (C_Two~
C₆) Alkenyl group, linear (C_Two~ C₆) Alkenoxy
(Alkenoxy) group, linear (C_Two~ C₆) Alkeno
Xyalkyl group, linear (C_Two~ C₆) Halogen substituted alke
Nyl group, linear (C_Two~ C₆) Halogen-substituted alkeneoxy
Basic, linear (C_Two~ C₆) Halogen-substituted alkeneoxy-a
Alkyl group, (C_Two~ C₆) Alkynyl group, (C_Two~ C₆A)
A alkynoxy group, (C_Two~ C₆) C
Logen-substituted alkynyl group, (C_Two~ C₆) Halogen-substituted
Rukinoxy group, (C_Three~ C₈) Cycloalkyl group, (C
_Three~ C₈) Cycloalkyloxy group, (C_Three~ C₈) Cyclo
An alkylamino group, (C₆~ C₁₂) Aryl group, (C₆~
C₁₂) Aryl-thio group, (C₆~ C₁₂) Aryl-
(C₁~ C_Four) Alkyl group, (C₆~ C₁₂) Aryloki
C-carbonyl group, (C₆~ C₁₂) Aryl-sulfoni
Group, (C₆~ C₁₂) Aryl-sulfinyl group, (C₆
~ C₁₂) Arylamino group, heteroaryl group, hetero
Aryloxy group, heteroaryl- (C₆~ C₁₂A)
Alkyl, heteroaryl-thio, heteroaryl
Xy-carbonyl group, heteroaryl-sulfonyl group,
A heteroaryl-sulfinyl group, and 1) I.I. The substituent in (b) is an aryl group or
When it is a loaryl group, the group is (C₁~ C₆) Al
Kill group, (C₁~ C₆) Alkoxy group, (C₁~ C₆)Halo
Gen-substituted alkyl group, (C₁~ C₆) Halogen substituted alco
At least one of the same selected from a xy group and a halogen
Or substituted with a different group,
A reel group is a group having 10 or less carbon atoms; The cycloalkyl group described in (b) is a halo
Gen and (C₁~ C_Four) 5 or more selected from alkyl groups
Can be substituted with the same or different groups below
3) I. Two of the substituents described in (b) are
Represents a tylenedioxy group and an ethylene dioxide group,
These include halogen and (C₁~ C₆) From alkyl group
One or two selected same or different substituents
4) I. (A) and I.I. Aryl as defined in (b)
Groups and heteroaryl groups may be partially or fully hydrogenated.
One or two CHs_TwoThe group is CO
II. R₁And R_TwoAre the same or different
And represents the following groups: hydrogen, halogen, (C₁~
C₆) Alkyl group, (C₁~ C₆) Alkyl halide
Group, cyano- (C₁~ C₆) Alkyl group, (C₁~ C₆A)
Lucoxy- (C₁~ C₆) Alkyl group, (C₁~ C₆) Al
Kirchio- (C₁~ C₆) Alkyl group, (C₁~ C₆) Al
Koxy- (C₁~ C₆) Alkoxy group, (C₁~ C₆) Al
Coxy group, (C₁~ C₆) Alkylthio group, (C₁~ C₆)
Alkylsulfonyl group, (C₁~ C₆) Alkyl-sulf
Inyl group, (C₁~ C₆) Alkoxy-carbonyl group,
(C₁~ C₆) Alkylamino group, 2- (C₁~ C₆) Al
A killamino group, (C₁~ C₆) Halogen-substituted alkoxy
Basic, linear (C_Two~ C₆) Alkenyl group, linear (C_Two~ C₆)
Alkenoxy group, linear (C_Two~ C₆) Halogenated alke
Nyl group, linear (C_Two~ C₆) Halogenated alkeneoxy
Group, (C_Two~ C₆) Alkynyl group, (C_Two~ C₆) Alkyne
An oxy group, (C_Two~ C₆) A halogenated alkynyl group, (C
_Two~ C₆) Halogenated alkyneoxy group, (C_Three~ C₈)
Chloroalkyl group, (C_Three~ C₈) Cycloalkyloxy
Group, (C_Three~ C₈) Cycloalkylamino group, (C₆~ C
₁₂) Aryl group, (C₆~ C₁₂) Aryloxy groups,
(C₆~ C₁₂) Aryl- (C₁~ C_Four) Alkyl groups,
(C₆~ C₁₂) Aryl-thio group, (C₆~ C₁₂) Ally
A ruoxy-carbonyl group, (C₆~ C₁₂) Aryl-s
A ruphonyl group, (C₆~ C₁₂) Aryl-sulfinyl
Group, (C₆~ C₁₂) Arylamino group, heteroaryl
Group, heteroaryloxy group, heteroaryl- (C₁
~ C_Four) Alkyl, heteroarylthio, hetero
Reeloxy-carbonyl group, heteroaryl-sulfo
A nyl group, and a heteroaryl-sulfinyl group, III. R_ThreeRepresents the following groups: (a) hydrogen, (b) (C₁~ C₆) Alkyl group, (C₆~
C₁₂) Aryl groups having not more than 10 carbon atoms
Low aryl group, linear (C_Two~ C₆) Alkenyl group, (C_Two
~ C₆) Alkynyl group and (C₁~ C_Four) Acyl group. I
Scarlet, III. The group described in (b) is a halogen,
(C₁~ C_Four) Alkyl group, (C₁~ C_Four) Alkoxy groups,
(C₁~ C_Four) A halogen-substituted alkyl group, (C₁~ C_FourA)
Alkylthio group and (C₁~ C_Four) Halogenated alkoxy
Substituted with the same or different groups selected from groups
IV. X is O, S, SO, SO_Two, NH or NR^a
Represents (R^aIs (C₁~ C _FourA.) Represents an alkyl group); Y is hydrogen, cyano group, halogen, (C₁~ C_FourA)
Alkyl group or (C₁~ C_FourVI.) Represents an alkoxy group; M is hydrogen or a monobasic metal atom (monoba)
sic metallic atom), and VII. m or n independently represents 0, 1, 2 or 3
Represent. The above-mentioned alkyl group, linear alkenyl group and
A rukinyl group can be straight or branched.
At the same time, it derives groups derived therefrom, such as
Alkyloxy groups derived from
Bonyl group, alkylthio group, halogenated alkyl group and
And arylalkyl groups.

[0006] Alkyl halide, linear alkenyl halide and alkynyl halide are alkyl, linear alkenyl and alkynyl groups in which one, more or all hydrogen atoms are substituted by halogen. It is. At the same time it applies to the groups derived from them. For example, groups derived from halogenated alkyl groups are halogenated alkyloxy, halogenated alkylthio, halogenated alkyloxycarbonyl, and aryl halogenated alkyl groups.

[0007] Halogen is fluorine, chlorine, bromine or iodine; preferred halogens are fluorine, chlorine and bromine. Preferred (C ₆ -C ₁₂ ) aryl groups are phenyl and groups derived from phenyl, such as naphthyl and biphenyl.

Preferred heteroaryl groups having 10 or less carbon atoms are monocyclic or bicyclic aryl groups, the formula of which includes at least one N, O or S, such as thiophene, benzo Thiophene group, furan group, benzofuran group, pyrrole group, indole group, imidazole group, pyrazole group, pyridine group, pyrazine group, pyrimidine group, diazine group, oxazole group, isoxazole group, thiazole group and isothiazole group. (C ₆ ~C ₁₂₎ heteroaryl group having an aryl group and more than 10 carbon atoms, which may optionally be hydrogenated partially or entirely. Further, one or two CH ₂ groups are substituted with CO, for example, a cyclohexene group, a cyclohexadione group and the like. In the general formulas (I), (II) and (III): Ar1 is preferably the following groups:

[0009]

Embedded image

Z is O, S or NR^FiveAnd R^FiveIs
Hydrogen, (C₁~ C₆) Alkyl group, (C₁~ C₆)halogen
Substituted alkyl group, (C₁~ C₆) Alkoxy- (C₁~
C₆) Alkyl group, (C₁~ C₆) Alkylthio- (C₁~
C₆) Alkyl groups, cyano- (C ₁~ C₆) Alkyl groups,
(C₁~ C₆) Alkyloxy-carbonyl group, linear (C
_Two~ C₆) Alkenyl group, linear (C_Two~ C₆) Halogenated
Alkenyl group, (C_Two~ C₆) Alkynyl group, (C_Two~ C₆)
An alkynyl halide group, (C_Three~ C₈) Cycloalkyl
A cycloalkyl group is halogen, (C₁~
C_Four) Alkyl group, (C₆~ C₁₂) Aryl group, (C₆~
C₁₂) Aryl- (C₁~ C_Four) Alkyl group, (C₆~ C
₁₂) Aryloxy-carbonyl groups, heteroaryl
Group, heteroaryloxy-carbonyl group and hetero
Aryl- (C₁~ C_Four) Alkyl groups (up to 10 carbon atoms)
5 or less same or different selected from
And P is an integer of 0 to 5
A number, R^FourAre the same or different, hydrogen, halogen
Nitro group, cyano group, (C₁~ C ₆) Alkyl groups,
(C₁~ C₆) Halogenated alkyl groups, cyano- (C₁~
C₆) Alkyl group, (C₁~ C₆) Alkoxy- (C₁~ C
₆) Alkyl group, (C₁~ C₆) Alkylthio- (C₁~ C
₆) Alkyl group, (C₁~ C₆) Alkoxy group, (C₁~ C
₆) Alkoxy- (C₁~ C₆) Alkoxy group, (C₁~ C
₆) Halogenated alkoxy group, (C₁~ C₆) Halogenation
An alkoxy-alkyl group, (C₁~ C₆) Alkylthio
Group, (C₁~ C₆) Halogenated alkylthio group, (C₁~
C₆) Alkylsulfonyl group, (C₁~ C₆) Alkyl-
Sulfinyl group, (C₁~ C₆) Alkoxy-carbonyl
Group, (C₁~ C₆) Alkylamino group, 2- (C₁~ C₆)
Alkylamino group, linear (C_Two~ C₆) Alkenyl group, line
Shape (C_Two~ C₆) Alkeneoxy group, linear (C_Two~ C₆A)
Alkeneoxyalkyl group, linear (C_Two~ C₆) Halogenation
Alkenyl group, linear (C_Two~ C₆) Alkenyl halide
Oxy group, linear (C_Two~ C₆) Halogenated alkeneoxy
Alkyl group, (C_Two~ C₆) Alkynyl group, (C_Two~ C₆)
Alkeneoxy group, (C_Two~ C₆) Alkynyl halide
Group, (C_Two~ C₆) Halogenated alkyneoxy group, (C_Three
~ C₈) Cycloalkyl group, (C_Three~ C₈) Cycloalkyl
Roxy group, (C_Three~ C₈) Cycloalkylamino group,
(C₆~ C₁₂) Aryl group, (C₆~ C₁₂) Aryloki
Group, (C₆~ C₁₂) Aryl-thio group, (C₆~ C₁₂)
Aryl- (C₁~ C_Four) Alkyl group, (C₆~ C₁₂A)
Reeloxy-carbonyl group, (C₆~ C₁₂) Aryl
-Sulfonyl group, (C₆~ C₁₂) Aryl-sulfini
Group, (C₆~ C₁₂) Arylamino group, heteroaryl
Group, heteroaryloxy group, heteroaryl- (C
₁~ C_Four) Alkyl, heteroarylthio, hetero
Reeloxy-carbonyl group, heteroaryl-sulfo
And a heteroaryl-sulfinyl group
And preferred R^FourThe groups are hydrogen, halogen, (C₁~ C₆)
Alkyl group, (C₁~ C₆) Halogenated alkyl group, (C
₁~ C₆) Alkoxy group, (C₁~ C₆) Alkoxy- (C
₁~ C₆) Alkyl group, (C₁~ C₆) Alkoxy- (C₁
~ C₆) Alkoxy group, (C₁~ C₆) Halogenated alco
A xy group, (C₁~ C₆) Alkylsulfonyl group, linear (C
_Two~ C₆) Alkenyl group, linear (C_Two~ C₆) Alkenoki
Si base, linear (C _Two~ C₆) Halogenated alkenyl group, linear
(C_Two~ C₆) Halogenated alkeneoxy group, (C_Two~
C₆) Alkynyl group, (C_Two~ C₆) Alkyneoxy group,
(C_Two~ C₆) A halogenated alkynyl group, (C_Two~ C₆) C
A logenated alkyneoxy group, (C_Three~ C₈) Cycloalkyl
Group, (C_Three~ C₈) Cycloalkyloxy group, (C_Three~
C₈) A halogenated cycloalkyl group, (C₆~ C₁₂Ant
Group, (C₆~ C₁₂) Aryloxy group, (C₆~
C₁₂) Aryl- (C₁~ C_Four) Alkyl group, (C₆~ C
₁₂) Aryl-thio groups having up to 10 carbon atoms
Heteroaryl group, heteroaryloxy group, heteroa
Reel-(C₁~ C_Four) Alkyl group etc., 1) R^FourIs an aryl group or a heteroaryl
When the group is a group represented by the formula (C)₁~ C₆) Alkyl
Group, (C₁~ C₆) Alkoxy group, (C₁~ C₆)halogen
Substituted alkyl group, (C₁~ C₆) Halogenated alkoxy group
And one or more same or different selected from halogen
A heteroaryl group which may be substituted with
Is a group having 10 or less carbon atoms, 2) R^FourThe cycloalkyl group described in
And (C₁~ C_Four) Up to 5
3) R can be substituted directly or^Four2 of the substituents described in
Represents a dioxy group or an ethylenedioxy group.
Is halogen and (C₁~ C₆) Selected from alkyl groups
With one or two identical or different substituents
be able to. Formulas (I), (II) and (II)
In I), Ar1 is preferably as described below
Group.

[0011]

Embedded image

In these formulas, Z is O, S or NR ⁵ , wherein R ⁵ is hydrogen, a (C ₁ -C ₆ ) alkyl group,
(C ₁ ~C ₆₎ halogenated alkyl, (C ₁ ~C ₆₎ alkoxy - (C ₁ ~C ₆₎ alkyl group, (C ₁ ~C ₆₎ alkoxy - carbonyl group, a linear (C ₂ -C ₆ ) alkenyl group,
Linear (C ₂ ~C ₆₎ halogenated alkenyl group, (C ₂ ~
C ₆₎ alkynyl group, and (C ₂ ~C ₆₎ halogenated alkynyl.

R ⁴ is hydrogen, halogen, (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) halogenated alkyl group, (C ₁
-C ₆₎ alkoxy - (C ₁ ~C ₆₎ alkyl group, (C ₁ ~
C ₆₎ alkoxy - (C ₁ ~C ₆₎ alkoxy groups, (C ₁ ~
C ₆₎ halogenated alkoxy groups, (C ₁ ~C ₆₎ alkylsulfonyl group, a linear (C ₂ ~C ₆₎ alkenyl group, a linear (C ₂ ~C ₆₎ alkenoxy group, a linear (C ₂ ~ C ₆₎ halogenated alkenyl radical, a linear (C ₂ ~C ₆₎ halogenated alkene group, (C ₂ ~C ₆₎ alkynyl, (C ₂ ~
C ₆ ) alkynoxy group, (C ₂ -C ₆ ) halogenated alkynyl group, (C ₂ -C ₆ ) halogenated alkynoxy group,
(C ₃ ~C ₈₎ cycloalkyl group and (C ₃ ~C ₈₎ halogenated cycloalkyl group.

R^FourTwo of the substituents in
Represents a range oxide group and an ethylene dioxide group,
These include halogen and (C₁~ C₆) From alkyl group
With one or two selected same or different groups
Can be Formulas (I), (II) and (II)
R in I)₁And R_TwoAre the same or different
And preferably hydrogen, halogen, (C₁~ C_Four) Archi
Group, (C ₁~ C_Four) Alkoxy group, (C₁~ C_Four) Haloge
Alkyl group, (C₁~ C_Four) Alkylthio group, linear
(C₁~ C₄) Alkenyl group, (C₁~ C₄) Alkini
Base, linear (C₁~ C₄) A halogenated alkenyl group,
(C₁~ C₄) A halogenated alkynyl group, (C₁~ C_Four)
Alkylsulfonyl group, (C₁~ C_Four) Alkylsulfi
Nil group and (C₁~ C_Four) An alkylamino group.

Formulas (I), (II) and (III)
R in_ThreeIs preferably hydrogen, (C₁~ C_Four) Archi
Group, (C₁~ C_Four) Halogenated alkyl group, linear (C₁
~ C ₄) Alkenyl group, (C₁~ C₄) Alkynyl group,
Linear (C₁~ C₄) An alkenyl halide group, (C₁~
C₄) An alkynyl halide group and (C₆~ C₁₂A)
It is a reel group. Formulas (I), (II) and (II)
In I), m is preferably 0 and n is preferably
Is 1. Formulas (I), (II) and (III)
In the above, preferred Ar2 is the following group:

[0016]

Embedded image

R represents N or CH, and q represents O, S,
NH or CH ₂ , preferably O or CH ₂ . R ⁶ is hydrogen, halogen, acryloxy group or propargyloxy. B.

[0018]

Embedded image

F represents fluorine, and t and g are the same
Or differently represents 0, 1, 2, 3 or 4 and t
And the sum of g is 5 or less,⁷Is the same or
Can be different, hydrogen, halogen, (C₁~ C₆) Al
Kill group, (C₁~ C₆) Halogenated alkyl group, (C₁~
C₆) Alkoxy group, (C ₁~ C₆) Alkoxy- (C₁~
C₆) Alkyl group, (C₁~ C₆) Alkoxy- (C ₁~ C
₆) Alkoxy group, (C₁~ C₆) Halogenated alkoxy
Group, (C₁~ C₆) Alkylsulfonyl group, linear (C_Two~
C₆) Alkenyl group, linear (C_Two~ C₆) Alkenoxy
Basic, linear (C_Two~ C₆) Alkeneoxy-alkyl groups, line
Shape (C_Two~ C₆) Halogenated alkenyl groups, linear (C_Two~
C₆) Halogenated alkeneoxy group, linear (C_Two~ C₆)
A halogenated alkeneoxy-alkyl group, (C_Two~ C₆)
Alkynyl group, (C_Two~ C₆) Alkeneoxy group, (C_Two
~ C₆) A halogenated alkynyl group, (C_Two~ C₆) Haloge
Alkyneoxy group, (C_Three~ C₈) Cycloalkyl
Group, (C _Three~ C₈) Cycloalkyloxy group, (C_Three~
C₈) A halogenated cycloalkyl group, (C₆~ C₁₂Ant
Group, (C₆~ C₁₂) Aryloxy group, (C₆~
C₁₂) Aryl- (C₁~ C_Four) Alkyl group, (C₆~ C
₁₂) Aryl-thio groups having up to 10 carbon atoms
Heteroaryl group, heteroaryloxy group, heteroa
Reel-(C₁~ C_FourC.) represents an alkyl group;

[0020]

Embedded image

In the above formula, w is 1, 2 or 3, and Z
Is O, S or NR ⁵ , wherein R ⁵ is hydrogen, (C _1-
C ₆₎ alkyl groups, (C ₁ ~C ₆₎ halogenated alkyl, (C ₁ ~C ₆₎ alkoxy - (C ₁ ~C ₆₎ alkyl, (C ₁ ~C ₆₎ alkylthio - (C ₁ ~ C ₆₎ alkyl group, cyano - (C ₁ ~C ₆₎ alkyl, (C ₁ ~C ₆₎ alkoxy - carbonyl group, a linear (C ₂ ~C ₆₎ alkenyl group, a linear (C ₂ -C ₆ ) A halogenated alkenyl group, (C ₂
-C ₆ ) alkynyl group, (C ₂ -C ₆ ) halogenated alkynyl group, and (C ₃ -C ₈ ) cycloalkyl group,
Cycloalkyl groups, halogen, (C ₁ ~C ₄₎ alkyl, (C ₆ ~C ₁₂₎ aryl group, (C ₆ ~C ₁₂₎ aryl - (C ₁ ~C ₄₎ alkyl group, (C ₆ ~ C ₁₂₎ aryloxy - carbonyl group, a heteroaryl group having 10 or fewer carbon atoms, heteroaryl - carbonyl group and heteroaryl - (C ₁ ~C ₄₎ differs no more than 5 identical or selected from an alkyl group It can be substituted with a substituent.

R⁸Can be the same or different,
Hydrogen, halogen, (C₁~ C₆) Alkyl group, (C₁~
C₆) Halogenated alkyl group, (C₁~ C₆) Alkoxy
Group, (C ₁~ C₆) Alkoxy- (C₁~ C₆) Alkyl
Group, (C₁~ C₆) Alkoxy- (C ₁~ C₆) Alkoxy
Group, (C₁~ C₆) Halogenated alkoxy group, linear (C_Two
~ C₆) Alkenyl group, linear (C_Two~ C₆) Alkenylo
A xy group, (C_Two~ C₆) Alkynyl group, (C_Two~ C₆) Al
A quinoxy group, (C_Two~ C₆) A halogenated alkynyl group,
(C_Two~ C₆) Halogenated alkyneoxy group, (C₆~ C
₁₂) Aryloxy group, (C₆~ C₁₂) Aryl- (C₁
~ C_Four) Alkyl group, (C₆~ C₁₂) Aryl-thio groups,
Heteroaryloxy having up to 10 carbon atoms
Group, heteroaryl-thio group, and heteroaryl-
(C₁~ C_Four) Represents an alkyl group. And R⁸A
The substituent of the reel group or the heteroaryl group is (C₁~
C₆) Alkyl group, (C₁~ C₆) Alkoxy group, (C₁~
C₆) Halogenated alkyl group, (C₁~ C₆) Halogenation
Can be selected from an alkoxy group and a halogen,
Can be the same or different.

Preferred R ⁸ is benzyl, phenoxy, acryl, propargyl, methyl and trifluoromethyl. D.

[0024]

Embedded image

F represents fluorine, R ⁹ is hydrogen, fluorine or a methyl group, and p is 0, 1 or 2. E. FIG.

[0026]

Embedded image

R represents a (C ₁ -C ₆ ) alkyl group or (C
₁ -C ₆₎ halogenated alkyl group, preferably a methyl group, A is oxygen, sulfur or NH. B is nitrogen or CH. In the general formulas (I), (II) and (III), preferred Ar2 are as follows:

[0028]

Embedded image

R ⁴ is a hydrogen, 3-fluoro, 4-fluoro or 4-chloro group. s is O, S, NH or CH ₂ , preferably O or CH ₂ . B.

[0030]

Embedded image

R ⁷ is a (C ₁ -C ₆ ) alkyl group, preferably CH ₃ , (C ₁ -C ₆ ) halogenated alkyl group, (C ₁ -C ₆ ) alkyl group.
-C ₆ ) alkoxy groups and (C ₁ -C ₆ ) halogenated alkoxy groups.

[0032]

Embedded image

R ⁷ is H, CH ₃ , or OCH ₃ . C.

[0034]

Embedded image

A is CH ₂ or O, and Z is O or S. D.

[0036]

Embedded image

F is fluorine, R ⁹ is hydrogen, fluorine or a methyl group, and p is 0, 1 or 2. E. FIG.

[0038]

Embedded image

R is a methyl group. A is oxygen, sulfur or NH. B is nitrogen or CH. Particularly preferred examples of compounds for formulas (I), (II) and (III) include the following compounds:
Ar1 is a substituted or unsubstituted aryl or heteroaryl group, and Ar2 is the particularly preferred A
r2. R ₁ and R ₂ are hydrogen, a methyl group or an ethyl group. R ₃ is a methyl group. m is 0,
n is 1, X is S, O or SO _2,.

The compounds of formulas (I) and (III) can exist in two types of geometric isomers: "cis" (formula Z) and "trans" (formula E). In the "cis" form (Formula Z), the oxime oxygen and the aryl or heteroaryl group Ar1 are located on the same side of the C = N double bond. In the “trans” form (Formula E), the oxime oxygen and the aryl or heteroaryl group Ar
1 are located on different sides of the C = N double bond. When transformed, its geometric structure does not change. Therefore, the formula (II)
In compounds of I), the "cis" type gives the corresponding "cis" type (I) oxime ether. The "trans" type (Formula E) (III) yields the corresponding "trans" type (I) oxime ether (Formula E).

[0041]

Embedded image

In addition, the alkyl-substituted- (hetero) aryl-ketoxime-O-ethers described in general formula (I), the intermediate ketones and oxime compounds described in general formulas (II) and (III), If it contains one or more asymmetric carbon atoms, it can be a racemate, a diastereoisomer or a pure optical isomer. The alkyl-substituted- (hetero) aryl-ketoxime-O-ethers described in general formula (I) and the intermediate oximes described in general formula (III) can be used in the “cis” form (formula Z),
The "trans" form (Formula E) is also referred to, as well as mixtures of both. Alkyl substitution described in the general formula (I)
(Hetero) aryl-ketoxime-O-ethers, intermediate ketones and oxime compounds described in general formulas (II) and (III), refer to the pure optical isomers as well as the racemic and diastereoisomers .

Alkyl substitution described in the general formula (I)
(Hetero) aryl-ketoxime-O-ethers, intermediate ketones and oxime compounds described in general formulas (II) and (III) refer not only to the pure isomers, but also to various isomer mixtures. Alkyl-substituted- (hetero) aryl-ketoxime-O- described in general formula (I)
Ethers, intermediate ketones and oxime compounds described in general formulas (II) and (III) are shown in Table 1, where the group Ar2 is simply indicated as G ^k (k = 1 to 35). However, formulas (I), (II) and (I)
The compound of II) is not limited to the compounds shown in Table 1.

The process for the preparation of the alkyl-substituted- (hetero) aryl-ketoxime-O-ethers of the invention of the formula (I), the intermediate ketones and the oxime compounds of the general formulas (II) and (III) Described below: a) A compound of the formula (III) and a compound of the formula (IV) are used.

[0045]

Embedded image

In the formula (IV), L represents a removable group. Thus, if M in formula (III) is hydrogen, a suitable base such as an alkali metal hydroxide, alkali metal carbonate, alkali metal bicarbonate, alkali metal alcohol, alkali metal, alkali metal hydride, pyridine or tertiary In the presence of a secondary amine, a suitable solvent, for example, one or two selected from water, tetrahydrofuran, toluene, benzene, acetonitrile and / or dimethylsulfoxide, is added, and a phase transfer catalyst (PTC), Butylammonium iodide, tetrabutylammonium bromide, tetraethylammonium bromide or 18-crown ether
6 and 0 to 120 ° C. under atmospheric pressure for 1 to 20
It can be obtained by performing a time reaction. If in formula (III) M is an alkali metal atom, for example sodium, the alkylation of the oxime salt is carried out under the same conditions, but without the presence of an alkali. Alternatively, the compound represented by the formula (II) is reacted with the compound represented by the formula (V) or a salt thereof, if necessary, in the presence of a suitable base.

[0047]

Embedded image

The compound (III) of the present invention can be produced by the following method. Reacting a compound of formula (II) with hydroxylamine hydrochloride or hydroxylamine sulfate in a suitable solvent (preferably water and / or alcohol) at 0-100 ° C. under atmospheric pressure Synthesized. If necessary, the synthesis can be carried out by adding a suitable base, for example an alkali metal hydroxide , alkali metal carbonate, alkali metal bicarbonate or pyridine. The compound (I) of the present invention represented by the formula (II)
I) is manufactured as follows. Compounds of formula (II) having different structures are synthesized using appropriate starting materials and corresponding synthetic methods. If X in the compound represented by the general formula (II) is S, the compound represented by the formula (VI) can be used.

[0049]

Embedded image

In the above formula, Ar 1, R ₁ , R ₂ , n and m have the same meanings as in claim 1, and the compound is obtained in an aqueous solvent at 30 to 100 ° C. under atmospheric pressure at 30 to 100 ° C.
Obtained by reacting with the corresponding sodium salt of sulfate alcohol for 10 hours. Alkyl-substituted- (hetero) aryl-ketoximes proposed in the present invention
O-ethers, intermediate ketones and oxime compounds
It has biological activity, and some compounds have particularly good biological activity. They show remarkable activity in the field of pest control, especially in agriculture, horticulture, flower cultivation and hygiene. They do not hurt crops and show a fast and sustained insecticidal effect in a satisfactory manner. here,
Pests include, but are not limited to, the following:

Insect pests: Orthoptera , such as roach, thrips,
For example, cotton sleeps (cotton thri)
ps), rice plant sleeps (rice p
lanth trips ) and cumber sleeps ; Homop
tera , such as leafhoppers,
Plant hoppers and arimaki; Lepidoptera , e.g., Eastern army worm
rm), cotton leaf worm (cotton le)
af worm, moth and cabage army worm; Hyme
noptera , such as wasp larvae; Dipter
a , for example, mosquitoes and flies; ticks and the like.

Fungal pathogen: Powdery mildew (Powdery)
mildew, downy mildew
w), Sclerotium , Venturi
a , Giberella , Fusarium et al. Weeds: Barnyard grass, Showtown Foxtail (shortawn f)
oxtail), wild sorghum (wild sou)
rghum); broadleaf tobacco weed (broadleaf)
weed), such as succulent plants (fat hen) ( Ch
enopodium ) and cornflower (bitte)
rpress).

By using the alkyl-substituted- (hetero) aryl-ketoxime-O-ethers, intermediate ketones or oxime compounds of the invention as active ingredients in agricultural pesticides, any desired type of agent, such as Emulsion oil, wettable powder (wettable p)
powder, suspensions, granules and the like. Suitable auxiliaries include carriers (diluents) and other auxiliaries, such as extenders, emulsifiers, wetting agents, dispersants,
Adhesives, and disintegrants.

Examples for the preparation of agricultural pesticides: Preparation of emulsion oils: 20 parts by weight of an alkyl-substituted- (hetero) aryl-ketoxime-O-ether, intermediate ketone or oxime compound according to the invention, 73 parts by weight Parts of a diluent (eg toluene) and 7 parts by weight of a suitable auxiliary were homogeneously mixed to produce an emulsion oil which, when applied, was diluted with water. Preparation of wettable powder: 20 parts by weight of alkyl-substituted- (hetero)
Aryl-ketoxime-O-ether, intermediate ketone or oxime compound, 53 parts by weight of clay, 20 parts by weight of bleached carbon black, 5 parts by weight of silicate lignin and 2 parts by weight of polyoxymethyl alkyl ether And crushed (gross)
und) and pulverized (pulverize)
d), a wettable powder was produced. The following examples are provided to further illustrate the present invention.

[0055]

EXAMPLES Example 1 1- (4-chlorophenyl) -2
-Methylthio-O-((3-phenoxyphenyl) methyl
1) 1-propanone oxime-Compound No. 30
- 1- (4-chlorophenyl) mixture of 2-methylthio-1-propanone oxime (Z and E isomers of, content =
1.7 g (0.007 mol) of 90%) were weighed and dissolved in 18 ml of water-free acetonitrile (containing 0.20 g of metallic sodium). After reacting at 30 to 40 ° C for 2 to 3 hours, 0.3 g of tetrabutylammonium iodide was added. Next, 1.91 g (0.008 mol) of m-phenoxybenzyl chloride (content = 90%) was added dropwise. After the addition, the temperature was slowly raised to 60-65 ° C, and the reaction was carried out for 8-9 hours. After treatment, 2.85 g of crude oil product (mixture of Z and E isomers) was obtained. Purified by petroleum ether-methyl acetate by vacuum column chromatography. Thus, pure Z isomer and pure E isomer were obtained. The product was a slightly yellow viscous liquid. The total weight of pure Z isomer and pure E isomer was 1.49 g. Purity: Z isomer = 92%, E
Isomer = 93% (gas chromatography). Yield 4
7%. NMR (δ ^CDCl3 _TMS ): E isomer: 1.26 (d, 3H, CH ₃ ), 2.05
_{(S, 3H, SCH 3)} , 4.76 (q, 1H, -CH
-S-), 5.15 (s, 2H, C = NO-CH
_{2 -), 6.96~7.66 (m,} 13H, protons on the benzene ring) Z isomer: 1.27 (d, 3H, CH 3), 1.93
_{(S, 3H, SCH 3)} , 3.60 (q, 1H, -CH
-S-), 5.02 (s, 2H, C = NO-CH
_{2 -), 6.88~7.38 (m,} 13H, protons on the benzene ring) Elemental analysis :( Found / calc): C%: 67.4
1 / 67.07, H%: 5.06 / 5.35, N%:
3.32 / 3.40, S%: 7.25 / 7.77

Example 2 1- (4-chlorophenyl)-
2-methylthio-O-((3-phenoxyphenyl) meth
Tyl) ethanone oxime-compound (1) 5
- of 1- (4-chlorophenyl) -2-methylthio - ethanone oxime (E-isomer, content = 90%) 1.7g (0.
007 mol), 1.76 g (0.007 mol) of m-phenoxybenzyl chloride (content = 90%), 0.3 g of tetrabutylammonium iodide and 4 m of toluene
1 was weighed and added to the reaction vessel. With constant stirring,
4 ml of an aqueous solution (containing 0.63 g of NaOH) were added in one portion. Slowly raise the temperature to 58-60 ° C, 7-8
A time reaction was performed. After treatment, the crude oily product 2.6
7 g (E isomer) were obtained. Purification by vacuum column chromatography with petroleum ether-ethyl acetate gave 1.39 g (E isomer) of a slightly yellow viscous liquid. The purity is 94% (gas chromatography),
The yield was 44%. NMR δ ^CDCl3 _TMS : 1.98 (s, 3H, S
_{CH 3), 3.72 (s,} 2H, -CH 2 -S), 5.1
9 (s, 2H, C = N-O-CH 2 -), 6.89~
7.66 (m, 13H, proton on benzene ring) Result of elemental analysis: (actual / calculated): C%: 66.4
1 / 66.08, H%: 5.06 / 4.88, N%:
3.52 / 3.50, S%: 8.05 / 8.54 Mass spectrum: ion peak M ⁺ (397)

Example 3 1- (4-chlorophenyl)-
2-methylthioethanone oxime-compound (II
I), No. 1 in Table 1. Synthesis of 5- 1- (4-chlorophenyl) -2-methylthio-ethanone 27.0 g (0.13 mol), ethanol 35 ml,
14 ml of water and 12.80 of hydroxylamine hydrochloride
g (0.18 mol) was added to a 250 ml three-necked flask equipped with a reflux condenser, thermometer and magnetic stirrer. While stirring, 16.0 g of solid NaOH
(0.4 mol) were added all at once. After the addition, room temperature (about 25
C), and reacted for 15 to 20 minutes. Next, the temperature was slowly increased to 45 ° C., and the reaction was performed for 45 minutes.
Next, the mixture was heated to the reflux temperature and reacted for 5 to 6 hours.
After cooling, treat to give off-white needle-like crystals 29g
(Mixture of Z and E isomers) was obtained. 90% purity
(Gas chromatography), the yield was 90%, and the melting point was 93.6-96.6 ° C. Elemental analysis result: (actual / calculated): C%: 50.4
2 / 50.11, H%: 4.83 / 4.64, N%:
6.47 / 6.49, S%: 13.82 / 14.80 Mass spectrum: ion peak M ⁺ (215)

Example 4: 1- (4-chlorophenyl)-
2-methylthioethanone (or 4'-chloro-2-
Methylthioacetophenone) -compound (II),
No. 5-Synthetic sodium methyl mercaptan aqueous solution (content = 37
%) (41.0 g, 0.217 mol) was added to a 250 ml three-necked flask equipped with a reflux condenser, a thermometer and a magnetic stirrer. At room temperature, 1- (4-chlorophenyl) -2-chloroacetophenone (content = 95
%) 24.75 g (0.124 mol) were added in one portion.
Next, the reaction was carried out at 60 to 80 ° C. under atmospheric pressure for 3 to 5 hours. The reaction mixture was cooled and worked up to give 27 g of an oily liquid product. The purity was 90% (gas chromatography) and the yield was 97%. Elemental analysis result: (actual value / calculated value): C%: 53.8
0 / 53.86, H%: 4.30 / 4.52, S%: 1
5.28 / 15.97 Mass spectrum: ion peak M ⁺ (200)

Example 5: 1- (4-chlorophenyl)-
2-chloroethanone (or 4'-chloro-2-chloro
Roasetofenon) Synthesis chlorobenzene 135g (1.2 mol) and anhydrous aluminum tetrachloride 88.8 g (0.667 mol), dropping funnel, magnetic stirrer, thermometer and reflux condenser (anhydrous calcium chloride drying agent tube With a desiccant tube and an alkali absorbing liquid)
Add to 0 ml 3-neck flask. After 69.5 g (0.615 mol) of chloroacetyl chloride was slowly added dropwise from an automatic dropping funnel at 5 to 15 ° C, the temperature was slowly increased to about 70 ° C, and tail gas was released. The reaction mixture was cooled and worked up to give 118 g of white needles. The purity is 90% (gas chromatography), the yield is 91%, and the melting point is 97.9-99.
0 ° C. (mp = 98-100 ° C. reported in the literature). Elemental analysis result: (actual / calculated): C%: 50.3
8 / 50.82, H%: 3.02 / 3.19 Mass spectrum: ion peak M ⁺ (188)

The compounds of formulas (I), (II) and (III) can be synthesized by the same method. All synthesized compounds were identified and confirmed by NMR analysis, infrared analysis, mass spectrum analysis and / or elemental analysis. Examples of Determination of Biological Activity: Z and E isomers showed different biological activities. In general, the biological activity of the E isomer is higher than the Z isomer, and the activity data is based on the activity data of the E isomer or the mixture of the Z and E isomers.

Embodiment 6: Mythymne par
Tests for Biological Activity against ata Alkyl-substituted- (hetero) aryl-ketoxime-O-ethers of the invention, prepared by the process described in the examples for the preparation of pesticides in agriculture described above, intermediates An emulsion oil or wettable powder of a ketone or active oxime compound was diluted with water to produce a pesticide solution having a predetermined concentration.

[0062] 10 Mythimne separa
ta and 5 pieces of corn debris were placed in a Petri dish and sprayed with an amount of pesticide solution. After exposure, they were kept indoors for normal cultivation. After 24 hours, the number of live and dead insects was counted. The test was performed three times and the results were averaged. A series of compounds (I) [Code No. 5,6
7, 8, 9, 10, 11, 12, 21, 22, 23, 3
0, 31, 32, 33, 34, 35, 36, 37, 4
6,47,48,213,216,229,230,2
31, 238, 254, 629, 632, 645, 64
6,647,654,657], but the concentration is 500p
pm (calculated as active ingredient content), 100
% Of mortality. Some compounds (I) [for example, code No. 5,8 and 30] have a concentration of 50
Even below 0 ppm gave 100% mortality.

Example 7 Aphid Aphis Faba
e) Biological activity against e The alkyl-substituted- (hetero) aryl-ketoxime-O-ether, ketone intermediate or ketone intermediate of the present invention prepared by the method described in the examples for the preparation of pesticides in agriculture The emulsion oil or wettable powder of the active oxime compound was diluted with water to produce a pesticide solution having a predetermined property. New seedlings were inoculated with Arimaki (15
More than one). The seedlings were then immersed (along with Arimaki) in a solution of the agricultural pesticide for 5 seconds, removed and the excess liquid was dropped. They were placed on a water-absorbing sponge and held with a glass rod. Twenty-four hours later, the number of live and dead arimaki was determined. The test was performed three times and the results were averaged. A series of compounds (I) [Code N
o. 5,8,21,22,23,30,33,46,4
7,48], when the concentration was 250 ppm (calculated as the content of the active ingredient), Arimaki was killed 100%. Some compounds (I) [Code No.
5,8 and 30] gave 100% mortality for Arimaraki, even at lower concentrations.

Example 8: Leafhopper Nephotetti
about biological activity against x cimetipes
Emulsion oil of an alkyl-substituted- (hetero) aryl-ketoxime-O-ether, ketone intermediate or active oxime compound of the present invention prepared by the process described in the examples for the preparation of pesticides in test agriculture Alternatively, the wettable powder was diluted with water to produce a pesticide solution having a predetermined property. Rice seedlings (second half-year seedlings (second
semester)) was immersed in a solution of an agricultural pesticide for 5 seconds and then removed. The liquid was dropped and then placed in a large test tube. Each test tube contained 20 seedlings. Next, 20 leafhoppers (5th instar) were introduced into the tube, and the mouth of the tube was covered with white cheesecloth. The tubes were kept at room temperature and the number of live and dead leafhoppers was determined after 24 hours. The test was performed three times and the results were averaged.
A series of compounds (I) [Code No. 5,6,7,
8, 9, 10, 11, 12, 21, 22, 23, 30,
31, 32, 33, 34, 36, 37, 46, 47, 4
8,188] was found to kill 100% of leafhoppers at a concentration of 250 ppm (calculated as active ingredient content). Some compounds (I) [Code No. 5,8,30,33,188] showed 100% insecticidal rates, even at lower concentrations.

All of the synthesized compounds also showed excellent biological activity against other insect pests. Compound (I) [Code No. Biological activity of 5] were as follows: Spinach armyworm E- forms _{LC 50 (ppm) <5 (} spinach army worm) plaques cutworm E- forms _{LC 50 (ppm) <5 (} spotted cutworm) American tobacco cutworm E- forms _{LC 50 (ppm) <10 (} American tobacco cutworm) Green peach aphid E- forms _{LC 50 (ppm)> 100 (} Green peach aphid) compound (I) [Table 1 code No. Biological activity of 30] were as follows: Spinach armyworm E- forms _{LC 50 (ppm) <5 (} spinach army worm) Z- form LC ₅₀ (ppm)> 150 plaques cutworm E- form LC _{50 (ppm) <1.5 (spotted} cutworm) Z- form LC ₅₀ (ppm)> 150 American tobacco cutworm E- forms _{LC 50 (ppm) <5 (} American tobacco cutworm) Z- form LC ₅₀ (ppm)> 150 Green peach aphids E- form _{LC 50 (ppm) <15 (} Green peach aphid) Z- form LC ₅₀ (ppm)> 150

Example 9: Test for antimicrobial activity The alkyl-substituted- (hetero) aryl-ketoxime-O-ether, ketone intermediate or active oxime compound of the present invention is diluted with a suitable diluent (eg, propanone),
A parent solution having a predetermined was prepared. 1 ml of this solution
Pipette into 0 ml of molten PDA medium. After shaking well, two identical samples were made by pouring into two Petri dishes. After cooling, mycelial pad (diameter = about 4mm)
Was collected and inoculated in the center of the culture dish. Diluent was used as a control. After inoculation, the dishes were kept in an incubator set at the appropriate temperature. After culturing for 72 hours, the growth length of the mycelium (diameter of the colony) was measured, and the bacterial growth inhibition rate was calculated. A series of compounds (III) [Code No.
5 and 7] were found to exhibit a growth inhibition of greater than 90% against one or more bacterial pathogens at a concentration of 100 ppm (calculated as the content of active ingredient).

Example 10: Test for herbicidal activity Alkyl-substituted- (hetero) aryl-ketoxime-O-ethers, ketones prepared by the method described in the examples for the preparation of pesticides in agriculture described above The emulsion oil or wettable powder of the intermediate or active oxime compound was diluted with water to produce a parent solution having the above-mentioned concentrations. Weeds (eg Echinochloa
(Crusgalli et al., height = about 0.3 cm) were placed on filter paper in a 9 cm petri dish. Next, the seedlings were covered with a piece of filter paper. An amount of the agricultural pesticide solution was added to the dish using a pipette. The dish was covered and placed in an illuminated incubator maintained at the appropriate temperature. Three
〜4 days later, root length, seedling height and its biomass were measured and% rejection was calculated. Certain compounds have a concentration (calculated as active ingredient content) of 100 ppm
It was found to exhibit growth inhibitory or growth promoting activity against one or more monocotyledonous and dicotyledonous weeds.

The Ar2 group in the formula (I) is simply G
^k (k = 1 to 35). Thus, in Table 1, general formula (VII) can be used to represent a compound having general formula (I). Part of formula (VII) is represented by formula (II)
And they are shown in Table 1 along with compounds having formula (II) and formula (III). However, the compounds of formulas (I), (II) and (III) are not limited to the compounds shown in Table 1.

[0069]

Embedded image

[0070]

[Table 1]

[0071]

[Table 2]

[0072]

[Table 3]

[0073]

[Table 4]

[0074]

[Table 5]

[0075]

[Table 6]

[0076]

[Table 7]

[0077]

[Table 8]

[0078]

[Table 9]

[0079]

[Table 10]

[0080]

[Table 11]

[0081]

[Table 12]

[0082]

[Table 13]

[0083]

[Table 14]

[0084]

[Table 15]

[0085]

[Table 16]

[0086]

[Table 17]

[0087]

[Table 18]

[0088]

[Table 19]

[0089]

[Table 20]

[0090]

[Table 21]

[0091]

[Table 22]

[0092]

[Table 23]

[0093]

[Table 24]

[0094]

[Table 25]

[0095]

[Table 26]

[0096]

[Table 27]

[0097]

[Table 28]

[0098]

[Table 29]

[0099]

[Table 30]

[0100]

[Table 31]

[0101]

[Table 32]

[0102]

[Table 33]

[0103]

[Table 34]

[0104]

[Table 35]

[0105]

[Table 36]

[0106]

[Table 37]

[0107]

[Table 38]

[0108]

[Table 39]

[0109]

[Table 40]

[0110]

[Table 41]

[0111]

[Table 42]

[0112]

[Table 43]

[0113]

[Table 44]

[0114]

[Table 45]

[0115]

[Table 46]

[0116]

[Table 47]

[0117]

[Table 48]

[0118]

[Table 49]

[0119]

[Table 50]

[0120]

[Table 51]

[0121]

[Table 52]

[0122]

[Table 53]

[0123]

[Table 54]

[0124]

[Table 55]

[0125]

[Table 56]

[0126]

[Table 57]

[0127]

[Table 58]

[0128]

[Table 59]

[0129]

[Table 60]

[0130]

[Table 61]

[0131]

[Table 62]

[0132]

[Table 63]

[0133]

[Table 64]

[0134]

[Table 65]

[0135]

[Table 66]

[0136]

[Table 67]

[0137]

[Table 68]

[0138]

[Table 69]

[0139]

[Table 70]

[0140]

[Table 71]

[0141]

[Table 72]

[0142]

[Table 73]

[0143]

[Table 74]

[0144]

[Table 75]

[0145]

[Table 76]

[0146]

[Table 77]

[0147]

[Table 78]

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) A01N 43/10 A01N 43/10 A 43/12 43/12 B 43/40 101 43/40 101C 43/54 43/54 B 47/02 47/02 C07B 61/00 300 C07B 61/00 300 C07C 319/14 C07C 319/14 323/22 323/22 323/47 323/47 (72) Inventor Shenyu Long 410007 Hunan, China Ministry, Changsha, Fulong Road M. 399, Hunan Research Institute of Chemical Industry (72) Inventor Shao Ming Ou 410007 China Hunan, Changsha, Fullon Road M. 399, Hunan Research Institute of Chemical Industry (72) Inventor Shunhe Leng, China 410007 Hunan Province, Changsha, Hulong Road M. 399, Hunan Research Research Institution Within the To of Chemical Industry (72) Inventor Shudong Liu 410007 China, Hunan Province, Changsha, Fulong Road M. 399, Hunan Research Institute of Chemical Industry (72) Inventor Yongjiang Wan, China 410007 Hunan Province, Changsha, Fulong Road M. 399, Hunan Research Institute of Chemical Industry (72) Inventor Chongke Hou China 410007 Hunan Province, Changsha, Hulong Road M. 399, Hunan Research Institute of Chemical Industry (72) Inventor Cheng Yin Hunan Province, China 410007 Hunan Province, Changsha, Fullon Road M. 399, within the Hunan Research Institute of Chemical Industry (72 ) Inventor Minch Huwan 410007 China, Hunan Province, Changsha, Fullon Road M. 399, Hunan Research Institute of Chemical Industry (72) Inventor Jiang Binh Sue China 410007 Hunan Province, Changsha, Fulong Road M. 399, Hunan Research Institute of Chemical Industry F-term (reference) 4H006 AA01 AA02 AB03 AC24 AC43 AC44 AC59 AC62 BA01 BA28 BA30 BA32 BB11 BB15 BB21 BB22 BB31 TA04 TB02 TB57 4H011 AA01 AA03 AB01 AB03 AC01 BA01 BB05 BB06 BB07 BB08 BB09 DA15 DA16 DD03 4H039 CA61 CD20 CD30

Claims (13)

[Claims] 1. The compounds of the general formulas (I), (II) and (II)
A biocidal alkyl-substituted (hetene)
B) Aryl-ketoxime-O-ether, intermediate keto
And oxime compounds, their enantiomers and stereoisomers
Form, and cis and trans forms:Here, Ar1 and Ar2 are the same or different
To represent the following groups: (a) (C₆~ C₁₂) Aryl groups or up to 10
A heteroaryl group having a carbon atom, or (b) or less
5 or less same or different substituents selected from
A group defined in (a) substituted with: halogen, nitro
B, cyano, (C₁~ C₆) Alkyl group, (C₁~
C₆) Halogen-substituted alkyl groups, cyano- (C₁~ C₆)
Alkyl group, (C₁~ C₆) Alkoxy- (C₁~ C₆A)
Alkyl group, (C₁~ C₆) Alkylthio group- (C₁~ C₆)
Alkyl group, (C₁~ C₆) Alkoxy group, (C₁~ C₆)
Alkoxy- (C₁~ C₆) Alkoxy group, (C₁~ C₆)
A halogen-substituted alkoxy group, (C₁~ C₆) Halogen substitution
An alkoxy-alkyl group, (C₁~ C₆) Alkylthio
Group, (C₁~ C₆) A halogen-substituted alkylthio group, (C₁
~ C₆) Alkylsulfonyl group, (C₁~ C₆) Alkyl
-Sulfinyl group, (C₁~ C₆) Alkoxy-carboni
Group, (C₁~ C₆) Alkylamino group, 2- (C₁~
C₆) Alkylamino group, linear (C_Two~ C₆) Alkenyl
Basic, linear (C_Two~ C₆) Alkeneoxy group, linear (C_Two~
C₆) Alkeneoxyalkyl group, linear (C_Two~ C₆) C
Logene-substituted alkenyl group, linear (C_Two~ C₆) Halogen storage
Substituted alkeneoxy group, linear (C_Two~ C₆) Halogen-substituted
Alkeneoxy-alkyl group, (C_Two~ C₆) Alkynyl
Group, (C_Two~ C₆) Alkenyloxy group, (C_Two~ C₆) C
Logen-substituted alkynyl group, (C_Two~ C ₆) Halogen-substituted
Rukinoxy group, (C_Three~ C₈) Cycloalkyl group, (C
_Three~ C ₈) Cycloalkyloxy group, (C_Three~ C₈) Cyclo
An alkylamino group, (C₆~ C ₁₂) Aryl group, (C₆~
C₁₂) Aryl-thio group, (C₆~ C₁₂) Aryl-
(C₁~ C_Four) Alkyl group, (C₆~ C₁₂) Aryloki
C-carbonyl group, (C₆~ C₁₂) Aryl-sulfoni
Group, (C₆~ C₁₂) Aryl-sulfinyl group, (C₆
~ C₁₂) Arylamino group, heteroaryl group, hetero
Aryloxy group, heteroaryl- (C₆~ C₁₂A)
Alkyl, heteroaryl-thio, heteroaryl
Xy-carbonyl, heteroaryl-sulfonyl and
And heteroaryl-sulfinyl group, wherein 1) (b) the substituent is an aryl group or a heteroaryl group;
When it is a reel group, the group is (C₁~ C₆) Alkyl
Group, (C₁~ C₆) Alkoxy group, (C₁~ C₆)halogen
Substituted alkyl group, (C₁~ C₆) Halogen-substituted alkoxy
Group, and one or more of the same or
Can be substituted with different groups,
2) a cycloalkyl group described in (b) is a group having 10 or less carbon atoms;
And (C₁~ C_Four) 5 or less selected from alkyl groups
3) two of the substituents described in (b) may be substituted with
When representing a dioxy group or an ethylenedioxy group,
These include halogen and (C₁~ C₆) Select from alkyl groups
With one or two identical or different substituents
And 4) an aryl group as defined in (a) and (b), and
Heteroaryl groups are partially or fully hydrogenated
One or two CHs_TwoGroup is substituted with CO
R₁And R_TwoAre the same
Or can be different and represent the following groups: hydrogen, halo
Gen, (C₁~ C₆) Alkyl group, (C₁~ C₆)halogen
Alkyl group, cyano- (C₁~ C₆) Alkyl group, (C
₁~ C₆) Alkoxy- (C₁~ C₆) Alkyl group, (C₁
~ C₆) Alkylthio- (C₁~ C₆) Alkyl group, (C₁
~ C₆) Alkoxy- (C₁~ C₆) Alkoxy group, (C₁
~ C₆) Alkoxy group, (C₁~ C₆) Alkylthio groups,
(C₁~ C₆) Alkylsulfonyl group, (C₁~ C₆) Al
A kill-sulfinyl group, (C₁~ C₆) Alkoxy-cal
Bonyl group, (C₁~ C₆) Alkylamino group, 2- (C₁
~ C₆) Alkylamino group, (C₁~ C₆) Halogen substitution
Alkoxy group, linear (C_Two~ C₆) Alkenyl group, linear
(C_Two~ C₆) Alkeneoxy group, linear (C_Two~ C₆)Halo
Genkated alkenyl group, linear (C_Two~ C₆) Halogenated al
A kenoxy group, (C_Two~ C₆) Alkynyl group, (C_Two~
C₆) Alkyneoxy group, (C_Two~ C₆) Halogenated al
Quinyl group, (C_Two~ C₆) Halogenated alkyneoxy groups,
(C_Three~ C₈) Cycloalkyl group, (C_Three~ C₈) Cycloa
Alkyloxy group, (C_Three~ C₈) Cycloalkylamino
Group, (C₆~ C₁₂) Aryl group, (C₆~ C₁₂) Aryl
An oxy group, (C₆~ C₁₂) Aryl- (C₁~ C_Four) Al
Kill group, (C₆~ C₁₂) Aryl-thio group, (C₆~
C₁₂) Aryloxy-carbonyl group, (C₆~ C₁₂)
An aryl-sulfonyl group, (C₆~ C₁₂) Aryl-s
Rufinyl group, (C₆~ C₁₂) Arylamino group, hete
Roaryl group, heteroaryloxy group, heteroaryl
Le- (C₁~ C_Four) Alkyl, heteroarylthio,
Heteroaryloxy-carbonyl group, heteroaryl
-Sulfonyl group and heteroaryl-sulfinyl
Group; R_ThreeRepresents the following groups: (a) hydrogen; (b) (C₁~ C₆) Alkyl group, (C₆~ C₁₂) Ally
Heteroaryl having up to 10 carbon atoms
Basic, linear (C_Two~ C₆) Alkenyl group, (C_Two~ C₆) Al
Quinyl group and (C₁~ C_Four) Acyl group; wherein (b)
Are halogen, (C₁~ C_Four) Alkyl
Group, (C ₁~ C_Four) Alkoxy group, (C₁~ C_Four)halogen
Substituted alkyl group, (C₁~ C_Four) Alkylthio and
(C₁~ C_Four) The same selected from halogenated alkoxy groups
Or substituted with a different group; X
Are O, S, SO, SO_Two, NH or NR^aRepresents
(R^aIs (C₁~ C_Four) Represents an alkyl group); Y is water
Element, cyano group, halogen, (C₁~ C_Four) Alkyl group or
Is (C₁~ C_Four) Represents an alkoxy group; M is hydrogen or
M or n is independently 0,
Represents 1, 2 or 3. 2. An alkyl-substituted (hetero) aryl-ketoxime-O-ether, intermediate ketone and oxime compound according to claim 1, wherein Ar1 is one of the following groups: Here, Z is O, S or NR ⁵ , and R ⁵ is hydrogen, a (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) halogen-substituted alkyl group, (C ₁ -C ₆ ) Alkoxy- (C ₁ -C ₆ )
Alkyl group, (C ₁ -C ₆ ) alkylthio- (C ₁ -C ₆ )
Alkyl group, cyano- (C ₁ -C ₆ ) alkyl group, (C ₁
-C ₆ ) alkyloxy-carbonyl group, linear (C ₂ -C
₆₎ alkenyl group, a linear (C ₂ -C ₆₎ halogenated alkenyl group, (C ₂ -C ₆₎ alkynyl, (C ₂ -C ₆₎ halogenated alkynyl, (C ₃ -C ₈₎ cycloalkyl a group, cycloalkyl group, halogen, (C ₁ ~C ₄₎ alkyl, (C ₆ ~C ₁₂₎ aryl group, (C ₆ ~C ₁₂₎ aryl - (C ₁ ~C ₄₎ alkyl group, (C ₆ -C ₁₂ ) aryloxy-carbonyl, heteroaryl, heteroaryloxy-carbonyl and heteroaryl-
It can be substituted with up to 5 same or different groups selected from (C ₁ -C ₄ ) alkyl groups (with up to 10 aryl carbon atoms); P is an integer from 0-5 Each R ⁴ is the same or different and is a halogen, nitro group, cyano group, (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ )
Halogenated alkyl group, cyano- (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy- (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylthio- (C ₁ -C ₆₎ alkyl, (C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆₎ alkoxy - (C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆₎ halogenated alkoxy group, (C ₁ ~ C ₆ ) Halogenated alkoxy-
Alkyl group, (C ₁ ~C ₆₎ alkylthio groups, (C ₁ ~
C ₆₎ a halogenated alkylthio group, (C ₁ ~C ₆₎ alkylsulfonyl groups, (C ₁ ~C ₆₎ alkyl - sulfinyl group, (C ₁ ~C ₆₎ alkoxy - carbonyl group, (C ₁ ~
C ₆₎ alkylamino group, 2- (C ₁ ~C ₆₎ alkylamino group, a linear (C ₂ ~C ₆₎ alkenyl group, a linear (C ₂ ~
C ₆₎ alkenoxy group, a linear (C ₂ ~C ₆₎ alkenoxy group, a linear (C ₂ ~C ₆₎ halogenated alkenyl group, a linear (C ₂ ~C ₆₎ halogenated alkene group,
Linear (C ₂ -C ₆ ) alkeneoxyalkyl halide groups, (C ₂ -C ₆ ) alkynyl groups, (C ₂ -C ₆ ) alkeneoxy groups, (C ₂ -C ₆ ) alkynyl halide groups, C
₂ -C ₆₎ halogenated alkyne group, (C ₃ ~C ₈₎ cycloalkyl group, (C ₃ ~C ₈₎ cycloalkyl group, (C ₃ ~C ₈₎ cycloalkylamino groups, (C ₆ ~ C
₁₂₎ aryl groups, (C ₆ -C ₁₂₎ aryloxy group,
(C ₆ ~C ₁₂₎ aryl - thio, (C ₆ ~C ₁₂₎ aryl - (C ₁ ~C ₄₎ alkyl, (C ₆ ~C ₁₂₎ aryloxy - carbonyl group, (C ₆ ~C ₁₂ ) aryl - sulfonyl group, (C ₆ -C ₁₂₎ aryl - sulfinyl group,
(C ₆ -C ₁₂ ) arylamino group, heteroaryl group,
Heteroaryloxy group, heteroaryl- (C _1-
C ₄ ) represents an alkyl group, a heteroarylthio group, a heteroaryloxy-carbonyl group, a heteroaryl-sulfonyl group, and a heteroaryl-sulfinyl group;
However, 1) when the substituent in R ⁴ is an aryl group or a heteroaryl group, the group is (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆₎ ) May be substituted with one or more same or different groups selected from halogen-substituted alkyl groups, (C ₁ -C ₆ ) halogen-substituted alkoxy groups and halogen; 2) the cycloalkyl group described for R ⁴ can be substituted with up to 5 same or different groups selected from halogen and (C ₁ -C ₄ ) alkyl group; 3) When the two substituents described for R ⁴ represent a methylenedioxy group and an ethylenedioxy group,
1 selected from halogen and (C ₁ -C ₆ ) alkyl groups
Or two or more of the same or different substituents. 3. An alkyl-substituted (hetero) aryl-ketoxime-O-ether, intermediate ketone and oxime compound according to claim 1, wherein Ar1 is one of the following groups: Here, Z is O, S or NR ⁵ , and R ⁵ is hydrogen, a (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) halogen-substituted alkyl group, (C ₁ -C ₆ ) Alkoxy- (C ₁ -C ₆ )
Alkyl group, (C ₁ -C ₆ ) alkylthio- (C ₁ -C ₆ )
Alkyl group, cyano- (C ₁ -C ₆ ) alkyl group, (C ₁
-C ₆ ) alkyloxy-carbonyl group, linear (C ₂ -C
₆₎ alkenyl group, a linear (C ₂ -C ₆₎ halogenated alkenyl group, (C ₂ -C ₆₎ alkynyl, (C ₂ -C ₆₎ halogenated alkynyl, (C ₃ -C ₈₎ cycloalkyl a group, cycloalkyl group, halogen, (C ₁ ~C ₄₎ alkyl, (C ₆ ~C ₁₂₎ aryl group, (C ₆ ~C ₁₂₎ aryl - (C ₁ ~C ₄₎ alkyl group, (C ₆ -C ₁₂ ) aryloxy-carbonyl, heteroaryl, heteroaryloxy-carbonyl and heteroaryl-
Each R ⁴ can be the same or different and can be substituted with up to 5 same or different groups selected from (C ₁ -C ₄ ) alkyl groups (with up to 10 aryl carbon atoms). , Halogen, nitro group, cyano group, (C
₁ -C ₆₎ alkyl group, (C _{1 ~C 6)} halogenated alkyl group, cyano - (C _{1 ~C 6)} alkyl, (C _{1 ~C 6)} alkoxy - (C _{1 ~C 6)} alkyl group (C ₁ -C ₆ ) alkylthio- (C ₁ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₆ ) alkoxy- (C ₁ -C ₆ ) alkoxy, C ₁ -C ₆ ) halogenated alkoxy group, (C
₁ -C ₆₎ halogenated alkoxy - alkyl group, (C ₁ ~
(C ₆ ) alkylthio group, (C ₁ -C ₆ ) halogenated alkylthio group, (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁
-C ₆ ) alkyl-sulfinyl group, (C ₁ -C ₆ ) alkoxy-carbonyl group, (C ₁ -C ₆ ) alkylamino group, 2- (C ₁ -C ₆ ) alkylamino group, linear (C ₂ ~
C ₆₎ alkenyl group, a linear (C ₂ -C ₆₎ alkenoxy group, a linear (C ₂ -C ₆₎ alkenoxy group, a linear (C ₂ -C ₆₎ halogenated alkenyl group, a linear ( C ₂ ~
C ₆ ) Halogenated alkeneoxy group, linear (C ₂ -C ₆ )
Halogenated alkenes oxyalkyl group, (C ₂ ~C ₆₎ alkynyl, (C ₂ ~C ₆₎ alkenoxy group, (C ₂ ~
C ₆ ) halogenated alkynyl group, (C ₂ -C ₆ ) halogenated alkyneoxy group, (C ₃ -C ₈ ) cycloalkyl group,
(C ₃ ~C ₈₎ cycloalkyl group, (C ₃ ~C ₈₎ cycloalkylamino groups, (C ₆ ~C ₁₂₎ aryl group,
(C ₆ ~C ₁₂₎ aryloxy group, (C ₆ ~C ₁₂₎ aryl - thio, (C ₆ ~C ₁₂₎ aryl - (C ₁ ~C ₄₎ alkyl, (C ₆ ~C ₁₂₎ aryl oxy - carbonyl group, (C ₆ ~C ₁₂₎ aryl - sulfonyl group, (C ₆ -C
₁₂₎ aryl - sulfinyl group, (C ₆ -C ₁₂₎ arylamino group, a heteroaryl group, heteroaryloxy group, heteroaryl - (C ₁ -C ₄₎ alkyl group, heteroarylthio group, heteroaryloxy - carbonyl A heteroaryl-sulfonyl group, a heteroaryl-sulfonyl group, and a heteroaryl-sulfinyl group. 4. R ₁ and R ₂ are the same or different and each is hydrogen, halogen, (C ₁ -C ₄ ) alkyl, (C ₁
-C ₄ ) alkoxy group, (C ₁ -C ₄ ) halogenated alkyl group, (C ₁ -C ₄ ) alkylthio group, linear (C ₁ -C ₄ )
(C ₄ ) alkenyl group, (C ₁ -C ₄ ) alkynyl group, linear (C ₁ -C ₄ ) halogenated alkenyl group, (C ₁ -C ₄ )
₄₎ a halogenated alkynyl group, a (C ₁ -C ₄₎ alkylsulfonyl groups, (C ₁ -C ₄₎ alkylsulfinyl group or a (C ₁ -C ₄₎ alkylamino group, the alkyl-substituted according to claim 1 (Hetero) aryl-ketoxime-O-ethers, intermediate ketones and oxime compounds. Is wherein R _3, hydrogen, (C ₁ ~C ₄₎ alkyl, (C ₁ ~C ₄₎ halogenated alkyl group, a linear _(C 1 ~
(C ₄ ) alkenyl group, (C ₁ -C ₄ ) alkynyl group, linear (C ₁ -C ₄ ) halogenated alkenyl group, (C ₁ -C ₄ )
₄₎ a halogenated alkynyl or (C ₆ -C ₁₂₎ was substituted according to claim 1, wherein an aryl group (hetero) aryl - ketoxime -O- ether, Intermediate ketone and oxime compound. 6. Ar2 in the general formula (I) is a group represented by the following:
The alkyl-substituted (hetero) according to claim 1, which represents
Aryl-ketoxime-O-ether, intermediate ketone and
And oxime compounds: A)Where r represents N or CH; q is O, S, NH
Or CH_TwoAnd R⁶Are hydrogen, halogen,
B) a riloxy group or a propargyloxy group;Where F represents fluorine; t and g are the same or
Are different and represent 0, 1, 2, 3 or 4, and t and
And the sum of g is 5 or less;⁷Are the same or different
Can be a halogen, (C₁~ C₆) Alkyl groups,
(C₁~ C₆) Halogenated alkyl group, (C₁~ C₆) Al
Coxy group, (C₁~ C₆) Alkoxy- (C₁~ C₆) Al
Kill group, (C₁~ C₆) Alkoxy- (C₁~ C₆) Arco
A xy group, (C₁~ C₆) Halogenated alkoxy group, (C₁
~ C₆) Alkylsulfonyl group, linear (C_Two~ C₆) Al
Kenyl group, linear (C_Two~ C₆) Alkenoxy group, linear
(C_Two~ C₆) Alkeneoxy-alkyl groups, linear (C_Two
~ C₆) Halogenated alkenyl groups, linear (C_Two~ C₆) C
Logenated alkeneoxy group, linear (C_Two~ C₆)halogen
Alkeneoxy-alkyl group, (C_Two~ C₆) Alkini
Group, (C_Two~ C₆) Alkenyloxy group, (C_Two~ C₆)
An alkynyl halide group, (C_Two~ C₆) Halogenated al
A quinoxy group, (C_Three~ C₈) Cycloalkyl group, (C _Three
~ C₈) Cycloalkyloxy group, (C_Three~ C₈) Haloge
Cycloalkyl group, (C₆~ C₁₂) Aryl groups,
(C₆~ C₁₂) Aryloxy group, (C₆~ C₁₂) Ally
Le- (C₁~ C_Four) Alkyl group, (C₆~ C₁₂) Aryl
-Thio groups, heteroaryls with up to 10 carbon atoms
Group, heteroaryloxy group and heteroaryl-
(C₁~ C_Four) Represents an alkyl group; C)Where Z is O, S or NR^FiveAnd R^FiveIs the water
Element, (C₁~ C₆) Alkyl group, (C₁~ C₆) Halogen storage
A substituted alkyl group, (C₁~ C₆) Alkoxy- (C₁~ C₆)
Alkyl group, (C₁~ C₆) Alkylthio- (C₁~ C₆)
Alkyl group, cyano- (C₁~ C₆) Alkyl group, (C₁
~ C₆) Alkyloxy-carbonyl group, linear (C_Two~ C
₆) Alkenyl group, linear (C_Two~ C₆) Halogenated alke
Nyl group, (C_Two~ C₆) Alkynyl group, (C_Two~ C₆)Halo
Alkynyl group, (C_Three~ C₈) With a cycloalkyl group
And the cycloalkyl group is halogen, (C₁~ C_FourA)
Alkyl group, (C₆~ C₁₂) Aryl group, (C₆~ C₁₂A)
Reel-(C₁~ C_Four) Alkyl group, (C₆~ C₁₂Ant
Oxy-carbonyl group, heteroaryl group, hetero
Aryloxy-carbonyl and heteroaryl-
(C₁~ C_Four) Alkyl groups (up to 10 aryl carbon atoms)
5 or less same or different selected from
W is 0, 1, 2, or 3
And each R⁸Are the same or different
N, (C₁~ C₆) Alkyl group, (C₁~ C₆) Halogenation
Alkyl group, (C₁~ C₆) Alkoxy group, (C₁~ C₆)
Alkoxy- (C₁~ C₆) Alkyl group, (C₁~ C₆A)
Lucoxy- (C₁~ C₆) Alkoxy group, (C₁~ C₆) C
Alkoxylated alkoxy group, linear (C_Two~ C₆) Alkenyl
Basic, linear (C_Two~ C₆) Alkeneoxy group, (C_Two~ C₆)
Alkynyl group, (C_Two~ C₆) Alkyneoxy group, (C_Two
~ C₆) A halogenated alkynyl group, (C_Two~ C₆) Haloge
Alkyloxy group, (C₆~ C₁₂) Aryloxy
Group, (C₆~ C₁₂) Aryl- (C₁~ C_Four) Alkyl
Group, (C₆~ C₁₂) Aryl-thio groups, up to 10 chars
Heteroaryloxy group having a hydrogen atom, heteroaryl
Ru-thio group and heteroaryl- (C₁~ C_Four) Al
Represents a alkyl group; and⁸The aryl group in
Or a heteroaryl group is represented by (C₁~ C₆) Alkyl groups,
(C₁~ C₆) Alkoxy group, (C₁~ C₆) Halogenated
Alkyl group, (C₁~ C₆) Halogenated alkoxy groups and
Can be substituted with halogen and the substituents are the same
Or can be different; D)Here, F represents fluorine, R⁹Is a hydrogen, fluorine or methyl group, and p is
0, 1 or 2; or E)Here, R is (C₁~ C₆) Alkyl group or (C₁~
C₆A) is a halogenated alkyl group; A is oxygen, sulfur,
Or NH; and B is nitrogen or CH. 7. A compound of the general formula: A method for producing a compound represented by the formula: With a compound of the formula [Wherein, R ¹ , R ² , R ³ , X, m, n, Ar1, M, A
r2 and Y have the same meaning as in claim 1 and L represents a leaving group], and in a solvent in the presence of a base or a phase transfer catalyst under atmospheric pressure at 0 to 120 ° C. A method comprising a step of reacting at a temperature for 1 to 20 hours. 8. The general formula: A method for producing a compound represented by the formula: With a compound of the formula [Wherein, R ¹ , R ² , R ³ , X, m, n, Ar1, Ar2
And Y has the same meaning as in claim 1, wherein L represents a leaving group], and a reaction in a solvent in the presence of a suitable base or a phase transfer catalyst. 9. L is selected from the group consisting of chlorine, bromine and —OSO ₂ ; wherein the base is an alkali metal oxide, an alkali metal carbonate, an alkali metal bicarbonate, an alkali metal alcohol salt, an alkali metal, an alkali metal. The phase transfer catalyst is selected from the group consisting of tetrabutylammonium iodide, tetrabutylammonium bromide, tetraethylammonium bromide and 18-crown ether-6; selected from the group consisting of metal hydrides, pyridine and tertiary amines; The method according to claim 7 or 8, wherein the solvent is selected from the group consisting of water, tetrahydrofuran, toluene, benzene, acetonitrile and dimethylsulfoxide. 10. The formula: embedded image [Wherein, R ¹ , R ² , R ³ , X, m, n, Ar 1 and M
Has the same meaning as in claim 1], wherein the compound has the formula: A method comprising reacting the compound of formula (I) with hydroxylamine hydrochloride or hydroxylamine sulfate in a suitable solvent at atmospheric pressure at a temperature of 0 to 100 ° C in the presence of an optional base. 11. The formula: embedded image Wherein R ¹ , R ² , R ³ , X, m, n and Ar 1 are
A method for producing a compound represented by the following formula: The in compound represented by the formula R ³ -X ^- of a salt having an anion, in an aqueous solution, 3 at atmospheric pressure
A method comprising a step of reacting at a temperature of 0 to 100 ° C. for 2 to 10 hours. 12. A biocidal composition comprising a compound according to claim 1 and a carrier, and optionally comprising one or more extenders, emulsifiers, wetting agents, dispersants, adhesives and disintegrants. 13. A method for controlling pests selected from the group consisting of insect pests, fungal pathogens and weeds, comprising contacting an effective amount of the biocidal composition of claim 12 with pests.