JP2007515444A - Substituted heterocyclic amides with bactericidal effects - Google Patents

Abstract

（式中、記号は明細書に示した意味を有する。）で示されるアミド、該物質の製造方法、望ましくない微生物を防除するための該物質の使用、並びに式（ＩＩＩａ）及び（ＩＩＩｂ）（式中、記号は明細書に示した意味を有する。）で示される中間体生成物が開示される。Formula (I)

(Wherein the symbols have the meanings indicated in the description), the process for producing the substance, the use of the substance for controlling unwanted microorganisms, and the formulas (IIIa) and (IIIb) ( Wherein the symbols have the meanings indicated in the specification.) Intermediate products are disclosed.

Description

  The present invention relates to amides, a plurality of production methods thereof and uses for controlling this pest.

  Amides having bactericidal properties are known, for example, from JP-A-2001-348378. However, in some cases there is room for enhancing the bactericidal action of these compounds.

  However, the ecological and economic demands made on modern fungicides are constantly increasing, for example with regard to activity spectrum, toxicity, selectivity, application rate, residue formation and preferred production, and also for example resistance issues. There is a continuing need to develop new fungicides that have advantages over conventional fungicides, at least in some areas.

  The present invention relates to a compound of formula (I)

〔式中、
Ｒ^１、Ｒ^２及びＲ^３は、同一であるか又は異なり、互いに独立して水素、ハロゲン、シアノ、ニトロを表すか、
いずれの場合にも１から８個の炭素原子を有する直鎖又は分枝鎖のアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル又はアルキルスルホニルを表すか；
いずれの場合にも２から６個の炭素原子を有する直鎖又は分枝鎖のアルケニル、アルキニル、アルケニルオキシ又はアルキニルオキシを表すか；
いずれの場合にも１から６個の炭素原子と１から１３個の同一又は異なるハロゲン原子を有する直鎖又は分枝鎖のハロアルキル、ハロアルコキシ、ハロアルキルチオ、ハロアルキルスルフィニル又はハロアルキルスルホニルを表すか；
いずれの場合にも２から６個の炭素原子と１から１３個の同一又は異なるハロゲン原子を有する直鎖又は分枝鎖のハロアルケニル又はハロアルケニルオキシを表すか；
いずれの場合にも個々のアルキル部分に１から６個の炭素原子を有する直鎖又は分枝鎖のアルキルアミノ、ジアルキルアミノ、アルキルカルボニル、アルコキシカルボニル、ヒドロキシイミノアルキル又はアルコキシイミノアルキルを表すか；
３から６個の炭素原子を有するシクロアルキルを表し、
（但し、Ｒ^１、Ｒ^２及びＲ^３は、同時に水素を表さないものとする。）、又は
Ｒ^１とＲ^２は、これらを結合している炭素原子と一緒になって炭素環を形成し、
Ｈｅｔは非置換又は置換５員芳香族複素環を表し、
Ｒ^４は水素、ハロゲン、１から８個の炭素原子を有するアルキル、２から８個の炭素原子を有するアルケニル又はアルキニル、又は１から８個の炭素原子と１から９個のハロゲン原子を有するハロアルキルを表し、
Ｒ^５及びＲ^６は、同一であるか又は異なり、互いに独立して非置換であるか又はいずれの場合にもハロゲンもしくはシアノで置換されたアルキル、いずれの場合にもそれぞれのアルキル鎖に１から８個の炭素原子を有するアルコキシアルキル、又はいずれの場合にも２から８個の炭素原子を有するアルケニルもしくはアルキニル、又は３から８個の炭素原子を有するシクロアルキルを表すか、又はアルキル鎖に１から８個の炭素原子を有する非置換又は置換アリールアルキルを表し、
Ａはアルカンジイル又はシクロアルカンジイルを表し、及び
Ｙは酸素又は硫黄を表す。〕
で示される新規化合物を提供する。

[Where,
R ¹ , R ² and R ³ are the same or different and each independently represents hydrogen, halogen, cyano, nitro,
Represents in any case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 8 carbon atoms;
Represents in each case a straight-chain or branched alkenyl, alkynyl, alkenyloxy or alkynyloxy having 2 to 6 carbon atoms;
In each case represents a straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
Represents in each case a straight-chain or branched haloalkenyl or haloalkenyloxy having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
In each case represents a straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, hydroxyiminoalkyl or alkoxyiminoalkyl having 1 to 6 carbon atoms in the individual alkyl part;
Represents a cycloalkyl having 3 to 6 carbon atoms,
(However, R ¹ , R ² and R ³ do not represent hydrogen at the same time.) Or R ¹ and R ² together with the carbon atom to which they are bonded form a carbocycle. And
Het represents an unsubstituted or substituted 5-membered aromatic heterocycle,
R ⁴ is hydrogen, halogen, alkyl having 1 to 8 carbon atoms, alkenyl or alkynyl having 2 to 8 carbon atoms, or haloalkyl having 1 to 8 carbon atoms and 1 to 9 halogen atoms Represents
R ⁵ and R ⁶ are the same or different and are, independently of one another, unsubstituted or in each case alkyl substituted with halogen or cyano, in each case from 1 to each alkyl chain Represents an alkoxyalkyl having 8 carbon atoms, or in each case alkenyl or alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms, or 1 in the alkyl chain Represents an unsubstituted or substituted arylalkyl having from 8 to 8 carbon atoms,
A represents alkanediyl or cycloalkanediyl, and Y represents oxygen or sulfur. ]
The novel compound shown by this is provided.

  In the above definition, a saturated or unsaturated hydrocarbon chain such as alkyl, alkanediyl, alkenyl or alkynyl is linear in any case, including in combination with heteroatoms as in alkoxy, alkylthio or alkylamino. Or it is a branched chain.

  Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

  Aryl represents an aromatic monocyclic or polycyclic hydrocarbon ring, for example phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.

  Cycloalkyl represents a saturated carbocyclic compound that, when appropriate, together with a ring fused or bridged with another carbocycle forms a polycyclic ring system.

  Cycloalkenyl refers to a carbocyclic compound that contains at least one double bond and, where appropriate, a ring fused or bridged with another carbocycle to form a polycyclic ring system.

  Further, it has been found that the novel amide represented by the formula (I) is highly active against pests and has a particularly strong bactericidal action.

  Where appropriate, the compounds of the invention exist as various possible isomers, in particular stereoisomers such as E and Z isomers, cis or trans isomers, threo and erythro isomers, and mixtures of optical isomers. . What is described or claimed is both E and Z isomers, as well as both threo and erythro isomers, optical isomers, and mixtures of these isomers, tautomeric isomers.

  The present invention preferably has the formula (Ia)

〔式中、
Ｒ^１、Ｒ^２及びＲ^３は、同一であるか又は異なり、互いに独立して水素、弗素、塩素、臭素、シアノ、ニトロ、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチル、メトキシ、エトキシ、ｎ−もしくはｉ−プロポキシ、メチルチオ、エチルチオ、ｎ−もしくはｉ−プロピルチオ、メチルスルフィニル、エチルスルフィニル、メチルスルホニルもしくはエチルスルホニル、トリフルオロメチル、トリフルオロエチル、ジフルオロメトキシ、トリフルオロメトキシ、ジフルオロクロロメトキシ、トリフルオロエトキシ、ジフルオロメチルチオ、ジフルオロクロロメチルチオ、トリフルオロメチルチオ、トリフルオロメチルスルフィニルもしくはトリフルオロメチルスルホニル、ジメチルアミノ、ジエチルアミノ、アセチル、プロピオニル、メトキシカルボニル、エトキシカルボニル、ヒドロキシイミノメチル、ヒドロキシイミノエチル、メトキシイミノメチル、エトキシイミノメチル、メトキシイミノエチル又はエトキシイミノエチル、シクロプロピル、シクロブチル、シクロペンチル又はシクロヘキシルを表すか、又は
Ｒ^１とＲ^２は、これらを結合している炭素原子と一緒になって５又は６員炭素環を形成し、
（但し、Ｒ^１、Ｒ^２及びＲ^３は、同時に水素を表さないものとする。）、
Ｒ^４ａは水素、弗素、塩素、臭素、シアノ、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチル、アリル、プロパルギル又はトリフルオロメチルを表し、
Ｒ^５及びＲ^６は、同一であるか又は異なり、互いに独立してメチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチルを表すか、
アリル、メチルアリル、クロトニル、プロピニルもしくはブチニル又はシアノメチルを表すか、
又は場合により水素、弗素、塩素、臭素、シアノ、ニトロ、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチル、メトキシ、エトキシ、ｎ−もしくはｉ−プロポキシ、メチルチオ、エチルチオ、ｎ−もしくはｉ−プロピルチオ、メチルスルフィニル、エチルスルフィニル、メチルスルホニル又はエチルスルホニル、トリフルオロメチル、トリフルオロエチル、ジフルオロメトキシ、トリフルオロメトキシ、ジフルオロクロロメトキシ、トリフルオロエトキシ、ジフルオロメチルチオ、ジフルオロクロロメチルチオ、トリフルオロメチルチオ、トリフルオロメチルスルフィニル又はトリフルオロメチルスルホニル、アセチル、プロピオニル、メトキシカルボニル、エトキシカルボニル、ヒドロキシイミノメチル、ヒドロキシイミノエチル、メトキシイミノメチル、エトキシイミノメチル、メトキシイミノエチル又はエトキシイミノエチル、シクロプロピル、シクロブチル、シクロペンチル又はシクロヘキシルで置換されていてもよいベンジルを表し、
Ａはメタンジイル、エタン−１，１−ジイル、エタン−１，２−ジイル、プロパン−１，１−ジイル、プロパン−１，２−ジイル、プロパン−１，３−ジイル、プロパン−２，２−ジイル、ブタン−１，１−ジイル、ブタン−１，２−ジイル、ブタン−１，３−ジイル、ブタン−１，４−ジイル、ブタン−２，２−ジイル、ブタン−２，３−ジイル、１，１−ジエチルエタン−１，２−ジイル、シクロプロパン−１，１−ジイル又はシクロプロパン−１，２−ジイルを表し、
Ｙは酸素又は硫黄を表し、及び
Ｇ^１は酸素、硫黄又はＮ−Ｒ^７ａを表す（但し、
Ｒ^７ａは水素、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表す。）。〕
で示される化合物を提供する。

[Where,
R ¹ , R ² and R ³ are the same or different and independently of one another hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethyl Sulfonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl R ¹ and R ² together with the carbon atom to which they are attached form a 5- or 6-membered carbocycle,
(Provided that R ¹ , R ² and R ³ do not represent hydrogen at the same time),
R ^4a is hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl Represents propargyl or trifluoromethyl,
R ⁵ and ^{R 6} are identical or different, independently of one another methyl, ethyl, n- or i- propyl, n-, i-, s- or t- butyl, n- pentyl, n- hexyl, represents n-heptyl,
Represents allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl,
Or optionally hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl , Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, Difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetyl, propionyl, methoxycarbonyl, Butoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, represents methoxyiminomethyl, ethoxy imino methyl, methoxyiminoethyl or ethoxy imino ethyl, cyclopropyl, cyclobutyl, benzyl which may be substituted by cyclopentyl or cyclohexyl,
A is methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2- Diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, butane-2,2-diyl, butane-2,3-diyl, Represents 1,1-diethylethane-1,2-diyl, cyclopropane-1,1-diyl or cyclopropane-1,2-diyl;
Y represents oxygen or sulfur, and G ¹ represents oxygen, sulfur or N—R ^7a (provided that
R ^7a represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
The compound shown by this is provided.

  Similarly, the present invention is preferably of formula (Ib)

〔式中、
Ａ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹは、式（Ｉａ）でＡ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹについて好ましいと述べた定義と同じように定義した通りであり、
Ｒ^４ｂは水素、弗素、塩素、臭素、シアノ、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチル、アリル、プロパルギル又はトリフルオロメチルを表し、
Ｇ^２は酸素、硫黄又はＮ−Ｒ^７ｂを表す（但し、
Ｒ^７ｂはメチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表す。）。〕
で示される化合物を提供する。

[Where,
^{A, R 1, R 2,} R 3, R 5, R 6 and Y are defined and described as preferred in formula (Ia) ^A, for ^{R 1, R 2, R 3} , R 5, R 6 and Y As defined in the same way,
R ^4b is hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl Represents propargyl or trifluoromethyl,
G ² represents oxygen, sulfur or N—R ^7b (provided that
R ^7b represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
The compound shown by this is provided.

  The present invention furthermore preferably has the formula (Ic)

〔式中、
Ａ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹは、式（Ｉａ）でＡ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹについて好ましいと述べた定義と同じように定義した通りであり、
Ｒ^４ｃは水素、弗素、塩素、臭素、シアノ、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチル、アリル、プロパルギル又はトリフルオロメチルを表し、
Ｇ^３は酸素、硫黄又はＮ−Ｒ^７ｃを表す（但し、
Ｒ^７ｃは水素、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表す。）。〕
で示される化合物を提供する。

[Where,
^{A, R 1, R 2,} R 3, R 5, R 6 and Y are defined and described as preferred in formula (Ia) ^A, for ^{R 1, R 2, R 3} , R 5, R 6 and Y As defined in the same way,
R ^4c is hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl Represents propargyl or trifluoromethyl,
G ³ represents oxygen, sulfur or N—R ^7c (provided that
R ^7c represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, the s- or t- butyl. ). ]
The compound shown by this is provided.

  The present invention furthermore preferably has the formula (Id)

〔式中、
Ａ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹは、式（Ｉａ）でＡ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹについて好ましいと述べた定義と同じように定義した通りであり、
Ｒ^４ｄは水素、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表し、
Ｇ^４は酸素、硫黄又はＮ−Ｒ^７ｄを表す（但し、
Ｒ^７ｄはメチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表す）〕
で示される化合物を提供する。

[Where,
^{A, R 1, R 2,} R 3, R 5, R 6 and Y are defined and described as preferred in formula (Ia) ^A, for ^{R 1, R 2, R 3} , R 5, R 6 and Y As defined in the same way,
R ^4d represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
G ⁴ are representative of oxygen, sulfur or ^{N-R 7d} (where
R ^7d represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl)]
The compound shown by this is provided.

  The present invention furthermore preferably has the formula (Ie)

〔式中、
Ａ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹは、式（Ｉａ）でＡ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹについて好ましいと述べた定義と同じように定義した通りであり、
Ｇ^５は酸素、硫黄又はＮ−Ｒ^７ｅを表す（但し、
Ｒ^７ｅは水素、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表す。）。〕
で示される化合物を提供する。

[Where,
^{A, R 1, R 2,} R 3, R 5, R 6 and Y are defined and described as preferred in formula (Ia) ^A, for ^{R 1, R 2, R 3} , R 5, R 6 and Y As defined in the same way,
G ⁵ represents an oxygen, sulfur or ^{N-R 7e} (where
R ^7e represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
The compound shown by this is provided.

  The present invention furthermore preferably has the formula (If)

〔式中、
Ａ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹは、式（Ｉａ）でＡ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹについて好ましいと述べた定義と同じように定義した通りであり、
Ｇ^６は酸素、硫黄又はＮ−Ｒ^７ｆを表す（但し、
Ｒ^７ｆは水素、メチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表す。）。〕
で示される化合物を提供する。

[Where,
^{A, R 1, R 2,} R 3, R 5, R 6 and Y are defined and described as preferred in formula (Ia) ^A, for ^{R 1, R 2, R 3} , R 5, R 6 and Y As defined in the same way,
G ⁶ represents oxygen, sulfur or N—R ^7f (provided that
R ^7f represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
The compound shown by this is provided.

  The present invention furthermore preferably has the formula (Ig)

〔式中、
Ａ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹは、式（Ｉａ）でＡ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^５、Ｒ^６及びＹについて好ましいと述べた定義と同じように定義した通りであり、
Ｇ^７は酸素、硫黄又はＮ−Ｒ^７ｇを表す（但し、
Ｒ^７ｇはメチル、エチル、ｎ−もしくはｉ−プロピル、ｎ−、ｉ−、ｓ−もしくはｔ−ブチルを表す。）。〕
で示される化合物を提供する。

[Where,
^{A, R 1, R 2,} R 3, R 5, R 6 and Y are defined and described as preferred in formula (Ia) ^A, for ^{R 1, R 2, R 3} , R 5, R 6 and Y As defined in the same way,
G ⁷ represents oxygen, sulfur or N—R ^{7 g} (provided that
R ^7g represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
The compound shown by this is provided.

In the formulas (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y are Has the following particularly preferred meanings:
R ¹ , R ² and R ³ are identical or different and, independently of one another, particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n -, I-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl Sulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoro Oromethylsulfonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl, cyclopropyl, cyclobutyl, cyclopentyl or Represents cyclohexyl or R ¹ and R ² together with the carbon atom to which they are attached form a 5- or 6-membered carbocyclic ring.

R ¹ , R ² and R ³ shall not simultaneously represent hydrogen.

  A is particularly preferably methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl or propane. It represents -2,2-diyl.

  Y particularly preferably represents oxygen or sulfur.

R ⁵ and R ⁶ are the same or different and, independently of one another, particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl. , N-hexyl, n-heptyl, allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl.

In formula (Ia):
R ^4a particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano, and G ¹ particularly preferably represents oxygen, sulfur or N—R ^7a (provided that
R ^7a particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ).

In formula (Ib):
R ^4b particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorine or cyano, and G ² is in particular Preferably, it represents oxygen, sulfur or N—R ^7b (provided that
R ^7b particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ).

In formula (Ic):
R ^4c particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano, and G ³ particularly preferably represents oxygen, sulfur or N—R ^7c (provided that
R ^7c particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ).

In formula (Id):
R ^4d particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano, and G ⁴ particularly preferably represents oxygen, sulfur or N—R ^7d (provided that
R ^7d particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ).

In formula (Ie),
G ⁵ particularly preferably represents oxygen, sulfur or N—R ^7e (provided that
R ^7e particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl).

In formula (If),
G ⁶ particularly preferably represents oxygen, sulfur or N—R ^7f (provided that
R ^7f particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ).

In formula (Ig):
G ⁷ particularly preferably represents oxygen, sulfur or N—R ^{7 g} (provided that
R ^7g particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ).

  The definitions of the general or preferred groups given above apply both to the final product of formula (I) and to the starting materials or intermediates required for the production as well in each case. Is done.

  For these groups, the group definitions specifically given in the specific combinations or preferred combinations of the various groups are substituted with other preferred ranges of group definitions, irrespective of the respective combinations shown.

Finally, the amide of formula (I) is
a) General formula (II)

（式中、
Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は、前記で定義した通りであり、Ｔはヒドロキシ、ハロゲン又はアルコキシを表す。）
で示されるカルボン酸誘導体を、一般式（ＩＩＩ）

(Where
R ^{1, R} 2, ^{R 3} and ^{R 4} are as defined above, T is representing hydroxy, halogen or alkoxy. )
A carboxylic acid derivative represented by the general formula (III)

（式中、
Ｒ^５、Ｒ^６及びＡは、前記で定義した通りである。）
で示されるアミン又はこの酸付加複合体と、適切ならば酸受容体の存在下で、適切ならば縮合剤の存在下で、適切ならば触媒の存在下で及び適切ならば希釈剤の存在下で反応させると得られるか、又は
ｂ）Ｙが酸素である場合の式（Ｉ）で示されるアミドを、硫化剤と、適切ならば希釈剤の存在下で反応させると得られることが見出された。

(Where
R ⁵ , R ⁶ and A are as defined above. )
Or an acid addition complex as shown above and if appropriate in the presence of an acid acceptor, if appropriate in the presence of a condensing agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent. Or b) obtained by reacting the amide of formula (I) when Y is oxygen with a sulfurizing agent, if appropriate in the presence of a diluent. It was done.

  For example, when 3- (4-chlorophenyl) -5-methylisoxazole-4-carbonyl chloride and (4-ethoxy-3-methoxybenzyl) amine are used as starting materials, the route of method (a) of the present invention is: This can be illustrated by the following formula scheme:

Formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out process a) of the present invention. In this formula (II), R ¹ , R ² , R ³ and R ⁴ are preferably and in particular R ¹ , R ² , R ³ in connection with the description of the compounds of formula (I) of the present invention. and R ⁴ is preferred and particularly preferred and each have the meanings have already described; T is preferably alkoxy having 1 to 4 carbon atoms, or especially a methoxy or ethoxy, represents hydroxy or chlorine.

  The starting materials of formula (II) are known and / or can be prepared by methods known per se [see, for example, J. Org. Org. Chem. 27 (1962) 4305; Chem. Soc. (1963) 5838; Chem. Soc. (1963) 5845; Chem. Ber. 106, 3275 (1973); U.S. Pat. No. 3,479,365; U.S. Pat. No. 3,551,440; Org. Chem. (1967) 32 (10) 3132; Tetrahedron 25, (1969), 389; Synthetic Com. (1987), 17 (2), 165; European Patent No. 352581; European Patent No. 352581; European Patent No. 1186598; Bioor. & Medicinal Chem. Lett. , 11 (5), 641 (2001); Japanese Patent Application Laid-Open No. 2001-101060; Japanese Patent Application Laid-Open No. 2001-1011059; European Patent No. 352581; Lett. 23 (2), 235 (1982); of Org. Chem. 55 (13), 4011 (1990); European Patent No. 352581; European Patent No. 3225281; Synthesis, (1), 64 (1996); British Patent No. 1,058,384; Japanese Patent No. 3,257,411; Am. Chem. Soc. (1969), 89 (21), 5462; Org. Chem. (1967), 27, 4305; U.S. Pat. No. 4,380,465; Chem. Ber. 105, (1972) 196; Tetrahedron Letters 17, (1971), 1281; International Publication No. WO 95/04724; Swiss Patent No. 5022365; European Patent No. 785193; Heterocycles (2000), 53 (1), 159; Aust. J. et al. Chem. (1994), 47, 1375; Bulletin des Soc. Chim. Belgium (1996), 105 (1), 33; Bulletin des Soc. Chim. Belgium (1996), 105 (4), 189].

Formula (III) provides a general definition of the amines further required as starting materials for carrying out the process a) of the present invention. In this formula (III), A, R ⁵ and R ⁶ are preferably and in particular in connection with the description of the compounds according to the invention, the meanings already mentioned as being preferred and particularly preferred for R ⁵ and R ⁶ respectively. Have.

  Some of the amines of formula (III) are known organic chemicals for synthesis and / or can be prepared by methods known per se.

  Formula (III-a)

（式中、
Ａ及びＲ^５は前記で定義した通りであり、Ｒ^８はアリル、プロパルギル、２−ブチニル又はシアノメチルを表す。）
及び式（ＩＩＩ−ｂ）

(Where
A and R ⁵ are as defined above, and R ⁸ represents allyl, propargyl, 2-butynyl or cyanomethyl. )
And the formula (III-b)

（式中、
Ａ及びＲ^５は前記で定義した通りであり、Ｒ^９はアリル、プロパルギル、２−ブチニル又はシアノメチルを表す。）
で示されるアミンは、新規であり、本発明の主題の一部である。

(Where
A and R ⁵ are as defined above, and R ⁹ represents allyl, propargyl, 2-butynyl or cyanomethyl. )
The amines represented by are novel and are part of the subject matter of the present invention.

  The amines represented by formula (III-a) and formula (III-b) are represented by the general formula (IV-a)

（式中、
Ａ及びＲ^５は前記で定義した通りである。）
で示されるヒドロキシル化合物又は一般式（ＩＶ−ｂ）

(Where
A and R ⁵ are as defined above. )
Or a general formula (IV-b)

（式中、
Ａ及びＲ^６は前記で定義した通りである。）
で示されるヒドロキシル化合物を、塩化アリル、臭化アリル又は塩化プロパルギル、臭化プロパルギル又はヨウ化プロパルギル、塩化２−ブチニル、臭化２−ブチニル又はヨウ化２−ブチニル、又はクロロアセトニトリル、ブロモアセトニトリル又はヨウ化アセトニトリルと、適切ならば例えばアセトニトリルのような希釈剤の存在下で、及び適切ならば例えば炭酸カリウムのような酸受容体の存在下で反応させると得られる。

(Where
A and R ⁶ are as defined above. )
A hydroxyl compound represented by the formula: Allyl chloride, allyl bromide or propargyl chloride, propargyl bromide or propargyl iodide, 2-butynyl chloride, 2-butynyl bromide or 2-butynyl iodide, or chloroacetonitrile, bromoacetonitrile or iodine It is obtained by reacting with chlorinated acetonitrile, if appropriate in the presence of a diluent such as acetonitrile, and if appropriate in the presence of an acid acceptor such as potassium carbonate.

Prior to alkylation, the amino groups of the compounds of formulas (IV-a) and (IV-b) are conventionally used for amines such as t-butoxycarbonyl, if appropriate using conventional methods. Protecting groups are provided. In this way, the formula ^{(IV-a *)} or ^(IV-b *)

（式中、
Ｒ^５及びＲ^６は前記で定義した通りであり、ＰＧは保護基を表す。）
で示される化合物が形成される。

(Where
R ⁵ and R ⁶ are as defined above, and PG represents a protecting group. )
Is formed.

Formula (III-a ^* ) or (III-b ^* )

（式中、
Ｒ^８、Ｒ^９、ＰＧ、並びにＲ^５及びＲ^６は、前記で定義した通りである。）
で示される化合物を最初に生成するアルキル化反応の後に、保護基を慣用の方法を使用して再度除去する（製造例も参照）。

(Where
R ⁸ , R ⁹ , PG, and R ⁵ and R ⁶ are as defined above. )
After the alkylation reaction which initially produces the compound of ## STR4 ## the protecting group is removed again using conventional methods (see also the preparation examples).

  For example, using 4- (aminomethyl) -2-methoxyphenol and allyl bromide as starting materials, the route of method c) of the present invention can be illustrated by the scheme of the following formula:

Formula (IV-a) provides a general definition of the hydroxyl compounds required as starting materials for carrying out process c) of the present invention. In this formula (IV-a), R ⁵ is preferably and in particular in the context of the description of the compounds of formula (I) according to the invention, meanings already mentioned as being preferred and particularly preferred for R ⁵ respectively. Have

  The hydroxyl compounds of the formula (IV-a) are commercially available chemicals for synthesis or can be prepared by known methods [see, for example, J. Org. Chem. Soc. 127 (1925) 560 and J.H. Amer. Chem. Soc. 72 (1950), 2781; see JP-A-11-130739 or German Patent 1958165].

Formula (IV-b) provides a general definition of the hydroxyl compounds required as another starting material for carrying out the process c) of the present invention. In this formula (IV-b), R ⁶ is preferably and in particular in connection with the description of the compounds of formula (I) according to the invention, meanings already mentioned as being preferred and particularly preferred for R ⁶ respectively. Have

  The hydroxyl compounds of the formula (IV-b) are commercially available synthetic chemicals or can be obtained by known methods [e.g. German Offenlegungsschrift 4322065; Org. Chem. 53 (5), 1064-71 (1988); Synth. Comm. 7 (1), 71-8 (1977)].

  Further required compounds as starting materials for carrying out process c) according to the invention: allyl chloride, allyl bromide or allyl iodide, propargyl chloride, propargyl bromide or propargyl iodide, 2-butynyl chloride, 2- Butynyl or 2-butynyl iodide, or chloroacetonitrile, bromoacetonitrile or iodoacetonitrile are common customary synthetic chemicals.

  For example, using 3- (4-chlorophenyl) -N- (4-ethoxy-3-methoxybenzyl) -5-methylisoxazole-4-carboxamide and phosphorus pentasulfide as starting materials, The pathway can be illustrated by the following formula scheme.

  The amides required as starting materials for carrying out the process b) according to the invention are the compounds according to the invention and can be obtained according to the process a) according to the invention.

  Suitable vulcanizing agents for carrying out process b) of the present invention are all reagents capable of exchanging carbon-bonded oxygen atoms for sulfur atoms, such as hydrogen sulfide, phosphorus pentasulfide or Lawesson's reagent. It is.

  Hydrogen sulfide, phosphorus pentasulfide or Lawesson reagent are commercially available chemicals for synthesis.

  Process a) according to the invention is carried out in the presence of a diluent, if appropriate. Suitable diluents are water and organic solvents. These diluents include, in particular, aliphatic, alicyclic or aromatic hydrocarbons which may be halogenated, such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane. , Dichloromethane, chloroform, carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones such as acetone, butanone or methyl isobutyl ketone; nitriles such as acetonitrile, Propionitrile or benzonitrile; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformani , N-methylpyrrolidone or hexamethylphosphate triamide; esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol, ethylene glycol Examples thereof include monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and a mixture of these with water or pure water.

  Process a) according to the invention is carried out in the presence of a suitable acid acceptor, if appropriate. Suitable acid acceptors are all customary inorganic and organic bases. These inorganic and organic bases include, for example, alkaline earth metals or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates such as sodium hydride, sodium amide, sodium methoxide. Sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate And tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, A diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU) and the like.

  Process a) according to the invention is carried out, if appropriate, in the presence of a suitable condensing agent. Suitable condensing agents are all condensing agents conventionally used for such amidation reactions. Acid halides such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; acid anhydrides such as ethyl chloroformate, methyl chloroformate, isobutyl chloroformate or methanesulfonyl Chloride; carbodiimide, such as N, N′-dicyclohexylcarbodiimide (DCC), or other conventional condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N′-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl Examples may include -1,2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride.

  Process a) according to the invention is carried out in the presence of a catalyst, if appropriate. As examples, 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide may be mentioned.

  When carrying out the process a) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures between -50 ° C and + 150 ° C, preferably between -20 ° C and 150 ° C.

  When carrying out the process a) according to the invention, the amine is generally used in an amount of 1 to 5 mol, preferably 1.0 to 2.5 mol, per mol of the carboxylic acid derivative of the formula (II). .

  The process a) according to the invention can also be carried out in a two-step process. In this case, the carboxylic acid derivative represented by the general formula (II) is first converted into an activated form and reacted with an amine represented by the general formula (III) in the next step to obtain the general formula of the present invention. An amide of formula (I) is obtained.

  Suitable activated forms of the carboxylic acid derivatives of the general formula (II) are all carboxy activated derivatives such as acid halides, preferably acid chlorides, acid azides, and also symmetrical and hybrid acid anhydrides. Produced in situ, for example, with mixed o-alkyl carboxylic anhydrides, and also with activated esters, such as p-nitrophenyl esters or N-hydroxysuccinimide esters, and condensing agents, such as dicyclohexylcarbodiimides or carboxylic acids Activated form.

  Suitable diluents for carrying out the process b) according to the invention are all inert organic solvents. As inert organic solvents, preferably aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons such as chlorobenzene, Dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxymethane, 1,2 -Diethoxyethane or anisole.

  When carrying out process b) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at a temperature from 0 ° C to 150 ° C, preferably from 0 ° C to 80 ° C.

  When carrying out the process b) according to the invention in order to produce the compounds according to the invention of the formula (I), per mole of the amide of the formula (I) when Y in the formula is oxygen The vulcanizing agent is generally used in an amount of 0.1 to 15 mol, preferably 0.5 to 8 mol.

  The reaction is carried out and work-up and isolation of the reaction product are carried out by known methods (see also production examples).

  The process according to the invention is generally carried out under normal pressure. However, it is also possible to operate under pressure or under reduced pressure, generally from 0.1 to 10 bar.

Conducting the reaction and working up and isolating the reaction products are carried out in a known manner. The compounds according to the invention have a strong fungicidal activity and are used in fungi and bacteria in the protection of crops and in the protection of various substances. Can be used to control unwanted microorganisms such as

Fungicides i.e. fungicide, phytomyxea in crop protection (Plasmodiophoromycetes), Oomycetes (Oomycetes), fungus such (Chytridiomycetes), Zygomycetes (Zygomycetes), Ascomycetes (Ascomycetes), Basidiomycetes (Basidiomycetes) and incomplete It can be used to control fungi ( Deuteromycetes ).

Bactericidal agent, Pseudomonas family in crop protection (Pseudomonadaceae), Rhizobium family (Rhizobiaceae), Enterobacteriaceae (Enterobacteriaceae), for controlling the bacteria Corynebacterium Department (Corynebacteriaceae) and Streptomyces family (Streptomycetaceae) Can be used.

Examples include, but are not limited to, certain pathogens that cause fungal and bacterial diseases and fall within the general names listed above:
Xanthomonas (Xanthomonas) species, for example Xanthomonas oryzae (. Xanthomonas campestris pv oryzae);
Pseudomonas (Pseudomonas) species, such as, for example, spot bacteria fungi of cucurbits (. Pseudomonas syringae pv lachrymans);
Erwinia (Erwinia) species, for example burns fungi (Erwinia amylovora);
Pythium (Pythium) species, for example seedlings rot fungi (Pythium ultimum);
Fitohotora (Phytophothora) species, for example tomatoes, potatoes Phytophthora (Phytophthora infestans);
Pseudoperonospora species, such as hop plague ( Pseudoperonospora humuli ) or cucurbitaceae downy mildew ( Pseudoperonospora cubensis );
Species of Plasmopara , for example, Plasmopara viticola ;
Buremia (Bremia) species, such as, for example, lettuce downy mildew (Bremia lactucae);
Peronospora species such as pea downy mildew ( Peronospora psi ) or rapeseed downy mildew ( P. brassicae );
Erysiphe species, such as Barley powdery mildew (Erysiphe graminis );
Sphaerotheca species, such as powdery mildew ( Sphaerotheca fulignea );
Podosufera (Podosphaera) species, for example apple mildew (Podosphaera leucotricha);
Venturia species, such as Venturia inequalis ;
Pyrenophora species, such as barley reticulum ( Pyrenophora teres ) or leafy fungus ( P. graminea ) [ conidia : Drechslera, syn: Helminthsporium ]
Cochliobolus species, for example, Cochliobolus sativus (conidiophytes: genus Drechslera, syn: genus Helminthosporum );
Uromyces species, such as the legume rust fungus ( Uromyces appendiculatus );
Puccinia species, such as wheat, rye red rust ( Puccinia recondita );
Sclerotinia species, for example, Sclerotinia sclerotiorum ;
Tilletia species, for example, Tilletia caries ;
Kurobokin ( Ustilago ) species such as barley naked smut fungus ( Ustilago nuda ) or oats naked smut ( Ustilago avenae );
Perikyuraria (Pellicularia) species, for example rice sheath blight fungus (Pellicularia sasakii);
Pyricularia species, such as rice blast fungus ( Pyricularia oryzae );
Fusarium (Fusarium) species, such as, for example, Fusarium Kurumoramu (Fusarium culmorum);
Botrytis (Botrytis) species, for example Botrytis cinerea (Botrytis cinerea);
Septoria species, eg, Wheat fungus ( Septoria nodorum );
Leptosphaeria species, such as Leptosphaeria nodorum ;
Cercospora species, such as Cercospora canescens ;
Alternaria species, such as Rapeseed Black Spot ( Alternaria brassicae ); and Pseudocercosporella species, such as Pseudocercosporella herpotrichoids .

  The active compounds according to the invention also show a potent strengthening action in plants. The active compounds according to the invention are therefore suitable for bringing together the internal defenses of plants against attack by unwanted microorganisms.

  As used herein, a plant enhancing (resistance-inducing) compound refers to a plant defense system that exhibits substantial resistance to these microorganisms when the treated plant is subsequently inoculated with undesirable microorganisms. It should be understood to mean a substance that can be stimulated.

  In this case, undesirable microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Accordingly, the compounds of the present invention can be used to protect plants from attack by the pathogens within a certain period of time after treatment. The period during which this protection is achieved generally ranges from 1 to 10 days, preferably from 1 to 7 days after treatment of the plant with the active compound.

  The fact that the active compounds are well tolerated by plants at the concentrations necessary to control plant diseases allows for the treatment of above-ground parts of plants, breeding stocks and seeds, and soil.

The active compounds of the present invention is the cultivation of the viticulture and fruit and vegetable diseases, for example, Alternaria (Alternaria) species can be used with particularly good results Phytophthora (Phytophothora) species and Tanjikutsuyukabi (Plasmopara) species control.

  The active compounds according to the invention are also suitable for increasing the yield of crops. The active compounds according to the invention also exhibit reduced toxicity and are well tolerated by plants.

  If appropriate, the active compounds according to the invention can also be used as herbicides, at a certain concentration and application rate, to regulate the growth of plants and to control animal pests. If appropriate, the active compounds according to the invention can also be used as intermediates and precursors in the synthesis of other active compounds.

  According to the present invention, all plants and plant parts can be treated. Plants are to be understood here as meaning all plants and plant groups, for example desirable and undesired wild plants or crop plants (including naturally occurring crop plants). The crop plant can be a plant, such as a transgenic plant, which can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods, or by a combination of these methods, and for example plant breeding It can be a plant variety that can or cannot be protected by family law. Plant parts are to be understood as meaning all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples of which can be mentioned are leaves, needles, stems, Stems, flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhizomes. Plant parts also include harvested and nutrient and reproductive propagation materials such as seedlings, tubers, rhizomes, short shoots and seeds.

  Treatment of the plants and plant parts according to the invention with the active compounds is carried out directly or by conventional treatment methods around the plants and plant parts, the growing environment or the storage area, for example immersion, spraying, evaporation, soot, It is carried out by application by spraying and application, and in the case of propagation material, in particular in the case of seeds, by applying one or more coatings.

  In protecting materials, the compounds of the present invention can be used to protect industrial materials from infection and destruction by unwanted microorganisms.

  As used herein, industrial material is understood to mean a non-biological material manufactured for use in industry. For example, industrial materials intended to be protected from microbial alteration or destruction by the active compounds of the present invention include adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic products, cooling lubricants As well as other materials that can be infected or destroyed by microorganisms. Parts of the production plant that may be impaired by microbial growth, such as cooling water circuits, may also be included within the scope of the material to be protected. Industrial materials that can be mentioned within the scope of the present invention are preferably adhesives, glues, paper and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.

  Microorganisms that can degrade or alter the industrial materials that may be mentioned are, for example, bacteria, fungi (fungi), yeast, algae and slime organisms. The active compounds according to the invention preferably act against fungi, in particular filamentous fungi, wood discoloring fungi and wood decay fungi (basidiomycetes) and against slime organisms and algae.

Examples of microorganisms from the following genera may be mentioned:
Alternaria genus ( Alternaria tenuis ), for example, Alternaria tenuis ,
Aspergillus genus ( Aspergillus niger), such as Aspergillus niger ,
Chaetomium genus (Chaetomium), for example Chaetomium-Gurobosamu (Chaetomium globosum),
The genus Coniophora , for example Coniophora puetana ,
Lentinus genus, for example Lentinus tigrinus ,
Penicillium (Penicillium) genus, for example Penicillium Guraukumu (Penicillium glaucum),
Polyporus genus, for example Polyporus versicolor ,
Aureobasidium (Aureobasidium) genus, for example, Aureobasidium pullulans (Aureobasidium pullulans),
The genus Sclerophoma , for example, Sclerophoma pitophila ,
Trichoderma (Trichoderma) genus, for example, Trichoderma Viride (Trichoderma viride),
Escherichia (Escherichia) genus, for example, E. coli (Escherichia coli),
Pseudomonas (Pseudomonas) species, for example Pseudomonas aeruginosa (Pseudomonas aeruginosa),
Staphylococcus genus, for example Staphylococcus aureus .

  Depending on the individual physical and / or chemical properties of the active compounds according to the invention, conventional formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and It can be converted into fine capsules in polymeric materials and seed coating compositions, and can be converted into ULV cooled and heated fumes formulations.

  These formulations are prepared in a known manner, for example with the active compound as a bulking agent, ie liquid solvent, pressurized liquefied gas and / or solid carrier, and in some cases surfactants, ie emulsifiers and / or dispersants, and / or Manufactured by mixing with a bubble former. When the extender used is water, for example, an organic solvent can be used as a cosolvent. In essence, suitable liquid solvents are aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, fatty acids. Aromatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong solvents such as Dimethylformamide or dimethyl sulfoxide, or water. A liquefied gaseous extender or carrier should be understood to mean gaseous liquids at standard temperature and atmospheric pressure, such as aerosol propellants such as halogenated hydrocarbons or butane, propane, nitrogen and carbon dioxide. . Suitable solid carriers are, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as fine silica, alumina and silicates. Suitable solid carriers for granules are, for example, crushed and fractionated natural stones such as calcite, pumice, marble, leptose and dolomite, or synthetic granules of inorganic and organic powders, and organic materials such as sawdust, coconut shell, corn Of the cob and tobacco stem. Suitable emulsifiers and / or cell formers are, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkylsulfonates. Alkyl sulfates, aryl sulfonates, or protein hydrolysis products. Suitable dispersing agents are, for example, lignosulfite waste liquor and methylcellulose.

  Tackifiers such as carboxymethyl cellulose and powdered, granular or latex natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids such as cephalins and lecithins and synthetic phospholipids Can be used in the above formulations. Other possible additives are mineral and vegetable oils.

  Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc Can be used.

  Such preparations generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90%.

  The active compounds according to the invention can be used as such or in formulations, or used as a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, for example to broaden the activity spectrum Or the development of resistance can be prevented. In many cases, a synergistic effect is obtained, ie the activity of the mixture is higher than the activity of this individual component.

Suitable mixing components are, for example, the following compounds:
Fungicide:
2-phenylphenol; 8-hydroxyquinoline sulfate; acibenzoral-S-methyl; aldimorph; amidoflumet; ampropylphos; ampropylphos potassium; andoprim; andirazine; azaconazole; azoxystrobin; benalaxyl; Benodanyl; benomyl; bench avaricarb isopropyl; benzacryl; benzacryl isobutyl; vilanaphos; binapacryl; biphenyl; vitertanol; blasticidin S; phoscalide; bromconazole; buprimate; butiobate; butylamine; polysulfide lime; cappsiholcin); captanhol; captan; carbendazim; carboxin; carpropamide; carvone; quinometi Nart; clofenazone; chlorphenazole; chloronebu; chlorothalonil; clozolineate; cloziracone; cyazofamide; cyflufenamide; simoxanyl; cyproconazole; cyprodinil; cyprofram; Dagger G; devacarb; diclofluanid; Diphenocarb; Diphenomeconazole; Diflumetrim; Dimethymol; Dimethomorph; Dimethotrope; Diniconazole; Diniconazole-M; Dinocup; Diphenylamine; Dipyrithion; ; Fenamidon; Fe Phenylmol; Fenbuconazole; Fenhexamide; Fenitropan; Phenoxanyl; Fenpiclonyl; Fenpropidin; Fenpropimorph; Farbum; Fluazinam; Flubenzimine; Fludioxonil; Flumetover; Flumorph; Fluoxastrobine; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriahol; folpette; fosetyl aluminum; fosetyl sodium; fuberidazole; flavaxyl; furametopyr; Guazatine; hexachlorobenzene; hexaconazole; Imazolil; Iminekazine Triacetate; Iminocazine Trialbesylate; Iodocarb; Ipconazole; Iprobenfos; Iprodione; Iprovaricarb; Mepronil; Metalaxyl; Metalaxyl M; Methoconazole; Metasulfocarb; Metofloxam; Methylam; Metominostrobin; Metosulfovax; Mildiomycin; Microbutanyl; Microzoline; Natamycin; Nicobifen; Isopropyl; Nobiflumuron; Nuarimol; Off-race; Orissas Oxodixyl; Oxophosphoric acid; Oxopoconazole; Oxycarboxyl; Oxyfenthine; Paclobutrazole; Pefrazoate; Penconazole; Penclon; Phosfeifene; Fusalide; Picoxtrobin; Piperalin; Polyoxins; Probenazole; Prochloraz; Procymidone; Propamocarb; Propanosine sodium; Propiconazole; Propinezide; Proquinazid; Prothioconazole; Pyraclostrobin; Pyrazophos; Pyrifenox; Pyrimethanil; Quinconazole; quinoxyphene; kintozen; Conazole; Spiroxamine; Sulfur; Tebuconazole; Teclophthalam; Technazen; Tetocyclase; Tetraconazole; Thiabendazole; Ticiofen; Triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin; triflumizole; trifolin; triticonazole; uniconazole; validamycin A; vinclozolin; dineb; dilam; zoxamide; (2S) -N- [2- [4- [ [3- (4-Chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [ Methylsulfonyl) amino] butanamide; 1- (1-naphthalenyl) -1H-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine; 2-amino-4- Methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide; 5-trichloro-2,6-pyridinedicarbonitrile; actinovate; cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol; 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate; hydrogen carbonate N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine; tetrathiocarboxylic acid sodium;
And copper salts and preparations such as Bordeaux liquid; copper hydroxide; copper naphthenate; copper oxychloride; copper sulfate; kufuraneb; cuprous oxide;
Bactericides:
Bromopol, dichlorophen, nitrapirine, nickel dimethyldithiocarbamate, kasugamycin, octyrinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper formulations.
Insecticide / acaricide / nematicide:
1. Inhibitors of acetylcholinesterase (AChE) 1.1 Carbamates [for example, aranicarb, aldicarb, aldoxycarb, alixicarb, aminocarb, azamethifos, bendiocarb, benfuracarb, bufencarb, porcine carb, butcarboxyl, butoxycarboxyl, carbaryl, carbofuran , Carbosulfan, chloetocarb, coumaphos, cyanophenphos, cyanophos, dimethylane, ethiophene carb, fenobucarb, phenothiocarb, formethanate, furthiocarb, isoprocarb, metam sodium, methiocarb, mesomil, metorcarb, oxamyl, pirimicarb, promecarb, thiodicarb Fanox, Triazamate, Trimetacarb, XMC, Ki Cyril carb)
1.2 Organophosphates (eg acephate, azamethiphos, azinephos (-methyl, -ethyl), bromophos-ethyl, bromfenbinphos (-methyl), butathiophos, kazusafos, carbophenothione, chloroethoxyphos, chlorfen Vinphos, Chlormefos, Chlorpyrifos (-Methyl, -Ethyl), Coumafos, Cyanophenphos, Cyanophos, Chlorfenvinphos, Dimeton-S-Methyl, Dimeton-S-Methylsulfone, Diarifos, Diazinon, Diclofenthion, Dichlorvos / DDVP, Dicrotophos, dimethoate, dimethylvinphos, dioxabenzophos, disulfotone, EPN, ethion, ethoprophos, etrimphos, famflu, phenamiphos, fenitrothion, phensulfothion, Enthion, Flupyrazophos, Phonophos, Formothione, Phosmethylan, Phosthiazate, Heptenofos, Iodofenphos, Iprovenfos, Isazofos, Isophenphos, Iso-o-salicylate, Isoxathion, Malathion, Mecarbam, Metacrifos, Metamidophos, Methidathion, Mevinfos, Monomethothoto Oxydimetone methyl, parathion (-methyl, -ethyl), phentoate, folate, hosalon, phosmet, phosphamidone, phosphocarb, phoxime, pyrimifos (-methyl, -ethyl), propenofos, propaphos, propetamphos, prothiophos, protoate, pyraclophos, pyridafenthion , Pyridathion, quinalphos, butylphos, sulfotep, sulp Host, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion]
2. Sodium Channel Modulator / Voltage-Dependent Sodium Channel Blocker 2.1 Pyrethroid [eg, Acrinatrin, Allethrin (d-cis-trans, d-trans), β-Cyfluthrin, Bifenthrin, Bioareslin, Bioareslin-S-cyclopentyl-isomerism Body, bioethanomethrin, biopermethrin, violesmethrin, clobepatrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, crocitrin, cycloprotorin, cyfluthrin, cyhalothrin, cyperthrin, cypermethrin β-, θ-, ζ-), cyphenothrin, DDT, deltamethrin, empentrin (IR-isomer), esfenvalerate, etofenprox, phen Lutorin, fenpropatoline, fenpyritrin, fenvalerate, flubrocitrinate, flucitrinate, flufenprox, flumethrin, fulvalinate, fubfenprox, γ-cyhalothrin, imiprotolin, cadreslin, λ-cyhalothrin, Metofluthrin, permethrin (cis-, trans), phenothrin (1R-trans isomer), plareslin, profluthrin, protrifenbute, pyrethmethrin, resmethrin, RU15525, silafluophene, τ-fulvalinate, tefluthrin, teratrithrin, tetramethrin IR-isomer), tralomethrin, transfluthrin, ZXI8901, pyrethrin (pyretrin)]
2.2 Oxadiazines (eg indoxacarb)
3. Acetylcholine receptor agonists / antagonists 3.1 Chloronicotinyl / neonicotinoids (eg, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithianidine, thiacloprid, thiamethoxam)
3.2 Nicotine, Bensultap, Cartap 4. Acetylcholine receptor modulators 4.1 Spinosins (eg spinosad)
5). GABA-dependent chloride channel antagonists 5.1 Cyclodiene organochlorine agents (eg, camfechlor, chlordane, endosulfan, γ-HCH, HCH, heptachlor, lindane, methoxychlor)
5.2 Fiproles (eg, acetoprole, ethiprole, fipronil, vaniliprole)
6). Chloride ion channel activator 6.1 Mectins (for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin)
7). Juvenile hormone mimetics (eg, diophenolan, epofenanane, phenoxycarb, hydroprene, quinoprene, metoprene, pyriproxyfen, triprene)
8). Ecdysone agonists / disruptors 8.1 diacylhydrazines (eg chromafenozide, halofenozide, methoxyphenozide, tebufenozide)
9. Chitin biosynthesis inhibitors 9.1 Benzoylureas [for example, bistrifluron, clofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, penfluron , Teflubenzuron, Triflumuron)
9.2 Buprofezin 9.3 Cyromazine 10. Inhibitors of oxidative phosphorylation, ATP disturbing substances 10.1 Diafenthiuron 10.2 Organotin (eg azocyclotin, cyhexatin, fenbutatin oxide)
11. Deoxidants of oxidative phosphorylation acting by interrupting the H proton concentration gradient 11.1 Pyrroles (eg chlorfenapyr)
11.2 Dinitrophenols (eg, binapacryl, dinobutone, dinocup, DNOC)
12 Site-I electron transfer inhibitor 12.1 METIs (eg, phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad)
12.2 Hydramethylnon,
12.3 Dicophor 13. Site-II electron transport inhibitor 13.1 Rotenone 14. Site-III electron transfer inhibitor 14.1 Acechinosyl, fluacrylprim 15. Bacillus thuringiensis strain 16, a bacterial disruptor of the insect intestinal membrane Inhibitors of fat synthesis 16.1 Tetronic acids (eg spirodiclofen, spiromesifen)
16.2 Tetramic acids [eg 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-ylethyl carbonate (also known as carvone Acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-ylethyl ester, CAS Reg.No.:382608-10 -8) and carboxylic acids, cis-3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-ylethyl ester (CAS Reg) No .: 203313-25-1)]
17. Carboxamides (eg flonicamid)
18. Octaopaminergic agonist (eg Amitraz)
19. Inhibitors of magnesium-stimulated ATPase (eg, propargite)
20. Phthalamide such ^[e.g., N 2 - [1,1-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo ^-N l - [2-methyl-4- [1,2,2,2-tetrafluoro - 1- (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS Reg. No.:272451-65-7), fulvendiamide]
21. Nereistoxin analogs (eg, thiocyclam oxalate, thiosartap sodium salt)
22. Biologicals, hormones or pheromones [e.g., azadirachtin, Bacillus (Bacillus) species, Beauveria (Beauveria) species, codlemone, Metarhizium (Metharhizium) species, Paecilomyces (Paecilomyces) species, thuringiensis Shin (Thuringiensin), Verticillium potassium ( Verticillium ) species]
23. Active compounds with unknown or non-specific mechanism of action 23.1 Fumigants (eg aluminum phosphide, methyl bromide, sulfuryl fluoride)
23.2 Selective feeding inhibitors (eg cryolite, flonicamid, pymetrozine)
23.3 Tick growth inhibitors (eg, clofentezin, etoxazole, hexythiazox)
23.4 Amidoflumet, Benclothiaz, Benzoximate, Biphenazate, Bromopropyrate, Buprofezin, Quinomethionate, Chlordiforme, Chlorbenzilate, Chlorpicrin, Clothiazoben, Cycloprene, Cyclodiflumet Fentriphanyl, fulbenzimine, fluphenimine, flutenzin, gossypure, hydramethylnon, japonilure, metoxadiazone, mineral oil, piperonylbutoxide, potassium oleate, pyrafluproyl, pyridalyl, pyriproyl p , Tetradiphone, Tetrasal, Triaracene, Verbutin,
Also, compound 3-methylphenylpropylcarbamate (Tsumaside Z), compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] Octane-3-carbonitrile (CAS Reg. No. 185982-80-3) and the corresponding 3-endo-isomer (CAS Reg. No. 185984-60-5) (International Publication No. WO 96/37494, Pamphlet, International And a formulation containing an insecticidal active plant extract, nematode, fungus or virus.

  Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators, safeners and / or information chemicals are also possible.

In addition, the compound represented by the formula (I) of the present invention also has a very good antifungal activity. The compounds are particularly dermatophytes and yeasts, filamentous fungi and biphasic fungi [e.g., Candida species such as Candida albicans (Candida albicans), Candida glabrata (Candida glabrata)], and epi Epidermophyton phytone-Furokkozumu (Epidermophyton floccosum ), Aspergillus species such as Aspergillus niger (Aspergillus niger) and Aspergillus fumigatus (Aspergillus fumigatus), Trichophyton species such as Trichophyton mentagrophytes (Trichophyton mentagrophytes), Microsporum species such as Microsporum canis (Microsporum canis) and Miku It has very broad anti-fungal activity against Suporumu-Ozuani (Microsporum audouinii). These lists of fungi are in no way limited to the fungal spectrum that can be covered, but are merely exemplary.

  The active compounds of the invention can be used as is, can be used in the form of this formulation or can be prepared from such forms, eg ready-to-use solutions, suspensions, wettable powders, pastes, aqueous solvents, It can be used in the form of powder and granules. Application is carried out by conventional methods, for example, watering, liquid spraying, spraying, sowing, dusting, foaming, spreading and the like. Moreover, the active compound of the present invention can be sprayed by a microdispersing method, or the active compound preparation or the active compound itself can be injected into soil. It is also possible to treat plant seeds.

  When the active compounds according to the invention are used as fungicides, the application rates can be varied within a relatively wide range depending on the type of application. For the treatment of plant parts, the application rates of the active compounds according to the invention are generally from 0.1 to 10,000 g / ha, preferably from 10 to 1000 g / ha. For seed dressing, the active compound application rates according to the invention are generally from 0.001 to 50 g / kg seed, preferably from 0.01 to 10 g / kg seed. For soil treatment, the application rates of the active compounds according to the invention are generally from 0.1 to 10,000 g / ha, preferably from 1 to 5000 g / ha.

  As already mentioned above, all plants and their parts can be treated according to the invention. In preferred embodiments, wild plant species and plant varieties, or plant species and plant varieties obtained by conventional biological breeding methods, such as cross-breeding or protoplast fusion methods, and portions thereof are treated. In another preferred embodiment, transgenic plants and plant varieties (genetically modified organisms) obtained by combining genetic engineering methods with, if appropriate, conventional methods, and parts thereof are treated. The terms “parts” or “parts of plants” or “plant parts” have already been explained above.

  Particularly preferably, plants of plant varieties that are commercially available or used in any case are treated according to the invention. Plant varieties are understood as plants having novel properties (“traits”) obtained by conventional breeding methods, by mutagenesis or by recombinant DNA technology. These plants can take cultivars, varieties, biotypes or genotypes.

  Depending on the plant species or plant varieties, their habitat and cultivation conditions (soil, climate, plant period, nutrients), the treatment of the present invention can also provide a superadditive (“synergistic”) effect. Thus, for example, reducing the application rate and / or expanding the activity spectrum and / or increasing the activity of the substances and compositions that can be used according to the invention, better plant growth, increased resistance to high or low temperatures, drought or water or soil Increased tolerance to salt, increased flowering performance, easier harvesting, accelerated ripening, higher yield, better quality and / or higher nutritional value harvest, better storage stability of the harvest and / or Or processability is possible, which exceeds the effects that were actually expected.

Transgenic plants or plant varieties that are preferably treated according to the present invention (ie transgenic plants or plant varieties obtained by genetic engineering methods) are useful properties that are particularly advantageous for these plants in genetic recombination methods. All the plants that have received the genetic material to which ("trait") has been given can be mentioned. Examples of such properties are better plant growth, increased resistance to high or low temperatures, increased resistance to drought or water or soil salinity, enhanced flowering performance, accelerated harvesting, accelerated ripening, higher yields Better quality and / or higher nutritional value harvest, better storage stability and / or processability of the harvest. Another example and particularly important example of such properties is the ability of plants to better defend against animal and microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and certain species. The increased resistance of plants to herbicidally active compounds. Examples of transgenic plants that may be mentioned are important crop plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rape and fruit trees (apples, pears, citrus fruits and grapes), Of particular importance are corn, soybeans, potatoes, cotton, tobacco and rape. Traits of particular importance are genetic materials derived from toxins formed in plants, in particular Bacillus thuringiensis [eg genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry2Bb and CryIF, and combinations thereof] are enhanced defense capabilities of plants against insects, arachnids, nematodes and slugs and snails (hereinafter: "Bt plant"). Also of particular importance are the enhancement of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), cystemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Defense ability. A trait of particular importance is also the increased resistance of plants to certain herbicidally active compounds such as imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg the “PAT” gene). The genes that confer the desired trait can also be present in combination with each other in the transgenic plant. Examples of “Bt plants” that may be mentioned are corn varieties, cotton varieties, soybean varieties and potato varieties, which are trade names YIELD GARD® (eg corn, cotton, soybean), KnockOut® ( For example, corn), StarLink® (eg, corn), Bollgard® (cotta), Nucoton® (cotta), and NewLeaf® (potato). Examples of herbicide resistant plants that may be mentioned are corn varieties, cotton varieties and soybean varieties, which are trade names Roundup Ready® (glyphosate resistant, eg corn, cotton, soybean), Liberty Link®. ) (Phosphinothricin resistance, for example rape), IMI® (imidazolinone resistance) and STS® (sulfonylurea resistance, for example corn). Examples of herbicide-resistant plants that can be cited (plants cultivated in a conventional manner for herbicide resistance) include varieties sold under the trade name Clearfield (registered trademark) (for example, corn). Of course, these descriptions also apply to plant varieties having these genetic characteristics or further genetic characteristics to be developed, and these plants will be developed and / or marketed in the future.

  The plants mentioned above can be treated particularly conveniently with the compounds or active compound mixtures of the general formula (I) according to the invention. The preferred ranges mentioned above for the active compounds or mixtures also apply to the treatment of these plants. It may be particularly important to treat plants with the compounds or mixtures specifically mentioned herein.

  The preparation and use of the active compounds according to the invention is illustrated in the following examples.

Production example
Example 1

室温で、３−（４−クロロフェニル）−５−メチル−４−イソオキサゾールカルボニルクロリド１．２８５ｇ（５．０６１ミリモル）を、ジクロロメタン２０ｍｌに溶解した４−エトキシ−３−メトキシベンジルアミン塩酸塩１．２０１ｇ（５．５１８ミリモル）とトリエチルアミン１．１１７ｇ（１１．０３５ミリモル）との溶液に加え、この混合物を還流下で１時間攪拌した。得られた混合物を室温まで冷却し、氷水１００ｍｌを加え、混合物を濃塩酸で酸性化し、ジクロロメタンを加え、有機相を分離し、水洗し、硫酸ナトリウムで乾燥し、減圧下で濃縮した。残留物をイソプロパノールから再結晶した。これにより、融点１５８℃のＮ４−（４−エトキシ−３−メトキシベンジル）−３−（４−クロロフェニル）−５−メチルイソオキサゾール−４−カルボキサミドを得た。

4-Ethoxy-3-methoxybenzylamine hydrochloride 1.285 g (5.061 mmol) of 3- (4-chlorophenyl) -5-methyl-4-isoxazolecarbonyl chloride dissolved in 20 ml of dichloromethane at room temperature. A solution of 201 g (5.518 mmol) and 1.117 g (11.035 mmol) of triethylamine was added and the mixture was stirred at reflux for 1 hour. The resulting mixture was cooled to room temperature, 100 ml of ice water was added, the mixture was acidified with concentrated hydrochloric acid, dichloromethane was added, the organic phase was separated, washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from isopropanol. As a result, N4- (4-ethoxy-3-methoxybenzyl) -3- (4-chlorophenyl) -5-methylisoxazole-4-carboxamide having a melting point of 158 ° C. was obtained.

  HPLC: Log P = 2.93.

  Further, the compounds represented by the formula (I) described in Table 1 below can also be produced in the same manner as in Example 1 and according to the general description of the production methods a) and b) of the present invention.

The log P value is EEC Directive 79/831 Annex V. HPLC according to A ⁸ (concentration gradient method, acetonitrile 0.1% aqueous phosphoric acid) was measured by.

Example of production of precursor represented by formula (III) (III-a-1)

Method c)
To a solution of 4.1 g (21.620 mmol) of 4-hydroxy-3-methoxybenzylamine hydrochloride and 5 ml of triethylamine dissolved in 50 ml of ethyl acetate, 4.954 g (22.7 mmol) of di-tert-butylpyrocarbonate. And the resulting mixture was stirred at room temperature for 18 hours. Then 100 ml of ethyl acetate was added and the mixture was washed with 50 ml of water, then with 50 ml of dilute citric acid and 50 ml of sodium bicarbonate solution and finally with 50 ml of saturated saline solution. The organic phase was dried over sodium sulfate and concentrated under reduced pressure.

This gave 3.7 g (67% of theory) of tert-butyl 4-hydroxy-3-methoxybenzylcarbamate (VI-a ^* -1).

  HPLC: LogP = 1.91.

To a solution of 3.7 g (14.607 mmol) of tert-butyl 4-hydroxy-3-methoxybenzylcarbamate (VI-a ^* -1) in 50 ml of acetone was added 5.33 g (36.519 mmol) of propargyl bromide. ), 5 g of anhydrous potassium carbonate and 0.15 g of potassium iodide were added, and the resulting mixture was heated under reflux for 18 hours. The reaction mixture was added to 100 ml of water and extracted with 200 ml of ether. The organic phase was washed twice with 10% strength aqueous sodium hydroxide solution, dried over sodium sulfate and concentrated. This gave 3.2 g (73% of theory) of tert-butyl 4- (propargyloxy) -3-methoxybenzylcarbamate (III-a ^* -1).

  (HPLC: LogP = 2.57).

  To a solution of 3.2 g (10.984 mmol) of tert-butyl 4- (propargyloxy) -3-methoxybenzylcarbamate in 50 ml of ethyl acetate was added 3 ml of concentrated hydrochloric acid solution, and the resulting mixture was stirred at room temperature for 18 hours. The resulting precipitate was filtered by stirring for a period of time. The resulting precipitate was washed twice with ethyl acetate and dried under reduced pressure. This gave 2.0 g (79% of theory) of 4- (propargyloxy) -3-methoxybenzylamine hydrochloride (III-a-1).

  (HPLC: Log P = 0.20).

  In a similar manner and according to the general description of the production method c) of the present invention, the compounds of formula (III) described in Table 2 below can also be produced:

The log P value is EEC Directive 79/831 Annex V. HPLC according to A ⁸ (concentration gradient method, acetonitrile 0.1% aqueous phosphoric acid) was measured by.

Example of use
Example A
Plague (tomato) test / protection test Solvent: 24.5 parts by weight of acetone
Dimethylacetamide 24.5 parts by weight Emulsifier: 1 part by weight of alkylaryl polyglycol ether 1 part by weight of active compound is mixed with the above amounts of solvent and emulsifier to produce a suitable formulation of the active compound, and the resulting concentrate The product was diluted with water to a predetermined concentration.

In order to test for protective activity, young seedlings were sprayed with the active compound formulation at the following application rates. After drying the spray coating, the seedlings were inoculated with an aqueous spore suspension of Phytophthora infestans . The plants were then placed in a culture room at about 20 ° C. and 100% relative atmospheric humidity.

  Evaluation was performed on the third day after inoculation. 0% means an effect corresponding to that of the control, whereas an effect of 100% means that no infection is observed.

  In this test, the compounds of the invention listed in Examples 1, 24, 38, 39, 40, 41, 42, 46, 47, 48, 50, 51, 54, 58, 61, 6 and 68 were 100 g / The application rate of ha showed an effect of 94% or more.

Example B
Downy mildew (grape) test / protection test Solvent: 24.5 parts by weight of acetone
Dimethylacetamide 24.5 parts by weight Emulsifier: 1 part by weight of alkylaryl polyglycol ether 1 part by weight of active compound is mixed with the above amounts of solvent and emulsifier to produce a suitable formulation of the active compound, and the resulting concentrate The product was diluted with water to a predetermined concentration.

In order to test for protective activity, young seedlings were sprayed with the active compound formulation at the following application rates. After the spray coating was dried, the seedlings were inoculated with an aqueous spore suspension of Plasmopara viticola and then placed in a culture room at about 20 ° C. and 100% relative atmospheric humidity for 1 day. . The plants were then placed in a greenhouse at about 21 ° C. and a relative atmospheric humidity of about 90% for 4 days. The plants were then moistened and placed in the culture room for 1 day.

  Evaluation was performed 6 days after the inoculation. 0% means an effect corresponding to that of the control, whereas an effect of 100% means that no infection is observed.

  In this test, Examples 1, 24, 35, 36, 38, 39, 40, 41, 42, 43, 44, 46, 47, 48, 49, 50, 51, 54, 56, 58, 61, 62 and The compound of the present invention listed in No. 68 showed an effect of 90% or more at an application rate of 100 g / ha.

Claims (9)

Formula (I)

[Where,
R ¹ , R ² and R ³ are the same or different and each independently represents hydrogen, halogen, cyano, nitro,
Represents in any case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having 1 to 8 carbon atoms;
Represents in each case a straight-chain or branched alkenyl, alkynyl, alkenyloxy or alkynyloxy having 2 to 6 carbon atoms;
In each case represents a straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
Represents in each case a straight-chain or branched haloalkenyl or haloalkenyloxy having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
In each case represents a straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, hydroxyiminoalkyl or alkoxyiminoalkyl having 1 to 6 carbon atoms in the individual alkyl part;
Represents a cycloalkyl having 3 to 6 carbon atoms (provided that R ¹ , R ² and R ³ do not represent hydrogen at the same time), or R ¹ and R ² bind these Together with the carbon atoms that form a carbocycle,
Het represents an unsubstituted or substituted 5-membered aromatic heterocycle,
R ⁴ is hydrogen, halogen, alkyl having 1 to 8 carbon atoms, alkenyl or alkynyl having 2 to 8 carbon atoms, or haloalkyl having 1 to 8 carbon atoms and 1 to 9 halogen atoms Represents
R ⁵ and R ⁶ are the same or different and are, independently of one another, unsubstituted or in each case alkyl substituted with halogen or cyano, in each case from 1 to each alkyl chain Represents an alkoxyalkyl having 8 carbon atoms, or in each case alkenyl or alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms, or 1 in the alkyl chain Represents an unsubstituted or substituted arylalkyl having from 8 to 8 carbon atoms,
A represents alkanediyl or cycloalkanediyl, and Y represents oxygen or sulfur. ]
An amide represented by a) Formula (Ia)

[Where,
R ¹ , R ² and R ³ are the same or different and independently of one another hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethyl Sulfonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl R ¹ and R ² together with the carbon atom to which they are attached form a 5- or 6-membered carbocycle,
^(Wherein, R 1, ^{R 2} and ^{R 3} shall not represent hydrogen at the same time.)
R ^4a is hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl Represents propargyl or trifluoromethyl,
R ⁵ and R ⁶ are the same or different and independently of each other methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, represents n-heptyl,
Represents allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl,
Or optionally hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl , Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, Difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetyl, propionyl, methoxycarbonyl, Butoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, represents methoxyiminomethyl, ethoxy imino methyl, methoxyiminoethyl or ethoxy imino ethyl, cyclopropyl, cyclobutyl, benzyl which may be substituted by cyclopentyl or cyclohexyl,
A is methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2- Diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, butane-2,2-diyl, butane-2,3-diyl, Represents 1,1-diethylethane-1,2-diyl, cyclopropane-1,1-diyl or cyclopropane-1,2-diyl;
Y represents oxygen or sulfur, and G ¹ represents oxygen, sulfur or N—R ^7a (provided that
R ^7a represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
A compound represented by:
b) Formula (Ib)

[Where,
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y are as defined in formula (Ia);
R ^4b is hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl Represents propargyl or trifluoromethyl,
G ² represents oxygen, sulfur or N—R ^7b (provided that
R ^7b represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
A compound represented by:
c) Formula (Ic)

[Where,
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y are as defined in formula (Ia);
R ^4c represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i- propyl, n-, i-, s- or t- butyl, n- pentyl, n- hexyl, n- heptyl, allyl Represents propargyl or trifluoromethyl,
G ³ represents oxygen, sulfur or N—R ^7c (provided that
R ^7c represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
A compound represented by:
d) Formula (Id)

[Where,
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y are as defined in formula (Ia);
R ^4d represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
G ⁴ represents oxygen, sulfur or N—R ^7d (provided that
R ^7d represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
A compound represented by:
e) Formula (Ie)

[Where,
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y are as defined in formula (Ia);
G ⁵ represents oxygen, sulfur or N—R ^7e (provided that
R ^7e represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
A compound represented by:
f) Formula (If)

[Where,
^{A, R 1, R 2,} R 3, R 5, R 6 and Y are as defined in Formula (Ia),
G ⁶ represents oxygen, sulfur or N—R ^7f (provided that
R ^7f represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
And g) Formula (Ig)

[Where,
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y are as defined in formula (Ia);
G ⁷ represents oxygen, sulfur or N—R ^{7 g} (provided that
R ^7g represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ). ]
A compound represented by:
A compound of formula (I) according to claim 1 selected from the group of Said symbols are as defined below:
R ¹ , R ² and R ³ are identical or different and, independently of one another, particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n -, I-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl Sulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or tri Fluoromethylsulfonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl, cyclopropyl, cyclobutyl, cyclopentyl or Represents cyclohexyl, or R ¹ and R ² together with the carbon atoms connecting them form a 5 or 6 membered carbocycle;
(Provided that R ¹ , R ² and R ³ do not represent hydrogen at the same time),
A is particularly preferably methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl or propane. Represents -2,2-diyl,
Y particularly preferably represents oxygen,
R ⁵ and R ⁶ are the same or different and, independently of one another, particularly preferably methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl. , N-hexyl, n-heptyl, allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl,
a) In formula (Ia):
R ^4a represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano, and G ¹ represents oxygen, sulfur Or N—R ^7a (provided that
R ^7a represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ),
b) In formula (Ib):
R ^4b represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorine or cyano, and G ² represents oxygen, sulfur or N—R ^7b (however,
R ^7b represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ),
c) In formula (Ic):
R ^4c represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano, and G ³ represents oxygen, sulfur Or N—R ^7c (provided that
R ^7c represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ),
d) In formula (Id):
R ^4d represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano, and G ⁴ represents oxygen, sulfur Or N—R ^7d (provided that
R ^7d represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ),
e) In formula (Ie):
G ⁵ represents oxygen, sulfur or N—R ^7e (provided that
R ^7e represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ),
f) In formula (If):
G ⁶ represents oxygen, sulfur or N—R ^7f (provided that
R ^7f represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ),
g) In formula (Ig):
G ⁷ represents oxygen, sulfur or N—R ^{7 g} (provided that
R ^7g represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. ),
A compound of formula (Ia) to (Ig) according to claim 2. A process for producing an amide represented by formula (I), comprising:
a) General formula (II)

[Where,
R ¹ , R ² , R ³ and R ⁴ are as defined in formula (I) in claim 1 and T represents hydroxy, halogen or alkoxy. ]
A carboxylic acid derivative represented by the general formula (III)

[Where,
R ⁵ , R ⁶ and A are as defined in formula (I) in claim 1. ]
Or an acid addition complex thereof, if appropriate in the presence of an acid acceptor, if appropriate in the presence of a condensing agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent. React with
b) A process for the preparation of the amide of formula (I), if appropriate (when Y in formula (I) is S) and reacting with a sulfurizing agent in the presence of a diluent if appropriate.   Undesirable, characterized in that it contains at least one amide of formula (I) according to one or more claims 1 to 3 and a bulking agent and / or surfactant A composition for controlling microorganisms.   Use of an amide of formula (I) according to one or more claims 1 to 3 for controlling unwanted microorganisms.   A method for controlling undesired microorganisms, which comprises applying the amide of formula (I) according to one or more of claims 1 to 3 to undesired microorganisms and / or their habitat.   Composition for controlling unwanted microorganisms, characterized in that the amide of formula (I) according to one or more of claims 1 to 3 is mixed with a bulking agent and / or a surfactant. Manufacturing method. Formula (III-a)

[Where,
A and R ⁵ are as defined in formula (I) in claim 1 and R ⁸ represents allyl, propargyl, 2-butynyl or cyanomethyl. ]
Or formula (III-b)

[Where,
A and R ⁵ are as defined in formula (I) in claim 1 and R ⁹ represents allyl, propargyl, 2-butynyl or cyanomethyl. ]
A compound represented by