JPH09503746A

JPH09503746A - Pyrimidin-4-ylaminoethylquinoline derivatives as pest control agents

Info

Publication number: JPH09503746A
Application number: JP7503793A
Authority: JP
Inventors: ヴァルター，ハーラルト
Original assignee: チバ−ガイギーアクチエンゲゼルシャフト
Priority date: 1993-07-09
Filing date: 1994-06-27
Publication date: 1997-04-15
Also published as: ZA944947B; AU7344794A; MX9405202A; WO1995001975A1; IL110236A0; EP0707582A1

Abstract

(57)【要約】遊離形態または塩形態の次式Ｉ（式中、置換基Ａは６−または７−位にあり；ＸはＯＲ₁₀、ＳＲ₁₀またはＮ（Ｒ₁₁）（Ｒ₁₂）を表し；ならびにＲ₁ないしＲ₁₂は請求の範囲に与えられた意味をもつ。）は有害生物を防除するための農薬の有効成分として使用できる。 (57) [Summary] The following formula I in free or salt form Wherein the substituent A is in the 6- or 7-position; X represents OR ₁₀ , SR ₁₀ or N (R ₁₁ ) (R ₁₂ ); and R ₁ to R ₁₂ are given in the claims. Can be used as an active ingredient of agricultural chemicals for controlling pests.

Description

【発明の詳細な説明】有害生物防除剤としてのピリミジン−４−イルアミノチルキノリン誘導体本発明はそれぞれの場合遊離形態または塩形態の、式Ｉ〔式中、置換基Ａは６−または７−位にあり、Ｒ₁は水素原子、炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルコキシ基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基または炭素原子数１ないし４のアルキルチオ基を表し；Ｒ₂およびＲ₃は互いに独立して、水素原子、炭素原子数１ないし４のアルキル基、１ないし５個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルコキシ基−炭素原子数１ないし４のアルキル基、ニトロ−炭素原子数１ないし４のアルキル基、シアノ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルカノイル−炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルコキシカルボニル−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルキルチオ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルカンスルフィニル−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルカンスルホニル−炭素原子数１ないし４のアルキル基、炭素原子数２ないし４のアルケニル基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数２ないし４のアルケニル基、炭素原子数２ないし４のアルキニル基、炭素原子数３ないし７のシクロアルキル基、炭素原子数１ないし４のアルコキシ基、ハロ−炭素原子数１ないし４のアルコキシ基、炭素原子数１ないし４のアルキルチオ基、ハロ−炭素原子数１ないし４のアルキルチオ基、炭素原子数１ないし４のアルキルスルフィニル基、炭素原子数１ないし４のアルキルスルホニル基、アミノ基、炭素原子数１ないし４のアシルアミノ基、ニトロ基、シアノ基、ヒドロキシル基またはハロゲン原子を表し；Ｒ₄は水素原子、炭素原子数１ないし４のアルキル基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルコキシ−炭素原子数１ないし４のアルキル基、ニトロ−炭素原子数１ないし４のアルキル基、シアノ−炭素原子数１ないし４のアルキル基、炭素原子数３ないし５のシクロアルキル基、ベンジル基、炭素原子数１ないし４のアルカノイル基、ベンゾイル基；そのフェニル基が未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ニトロ基およびシアノ基からなる群から選択された１、２もしくは３個の置換基で置換されたベンゾイル基を表し；Ｒ₅およびＲ₆は、互いに独立して、水素原子、炭素原子数１ないし４のアルキル基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルコキシ−炭素原子数１ないし４のアルキル基、ニトロ−炭素原子数１ないし４のアルキル基、シアノ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルコキシカルボニル−炭素原子数１ないし４のアルキル基または；未置換であるかまたはハロゲン原子および炭素原子数１ないし２のアルキル基からなる群から選択された１もしくは２の置換基により置換された炭素原子数３ないし６のシクロアルキル基を表し；Ｒ₇は水素原子、ハロゲン原子、炭素原子数１ないし４のアルキル基、シクロプロピル基、炭素原子数１ないし４のアルコキシ基または炭素原子数１ないし４のアルキルチオ基を表し；ＸはＯＲ₁₀、ＳＲ₁₀またはＮ（Ｒ₁₁）Ｒ₁₂を表し；Ｒ₁₀は水素原子；置換もしくは未置換である、１２個以下の炭素原子を有する開鎖、飽和または不飽和炭化水素基；置換もしくは未置換である、１０個以下の炭素原子を有する環状、飽和または不飽和炭化水素基；置換もしくは未置換のベンジル基；あるいは置換もしくは未置換の複素環基を表し；Ｒ₁₁は水素原子；８個以下の炭素原子を有し、および未置換であるかまたは１ないし５個のハロゲン原子、炭素原子数１ないし２のアルコキシ基、ヒドロキシル基、ニトロ基、シアノ基、炭素原子数１ないし４のアルカノイル基、ハロ−炭素原子数１ないし４のアルカノイル基もしくは炭素原子数１ないし４のアルコキシカルボニル基によって置換された、開鎖、飽和または不飽和炭化水素基；１０個以下の炭素原子数をもつ、環式、飽和もしくは不飽和炭化水素基；または炭素環が未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ハロメチル基、ニトロ基もしくはシアノ基により一もしくは二置換されたベンジル基；あるいは未置換であるかまたは炭素原子数１ないし２のアルキル基、ハロゲン原子、ハロメチル基、ニトロ基もしくはシアノ基からなる系列からの同じかまたは異なる置換基により一ないし三置換された複素環基を表し；Ｒ₁₂は水素原子または炭素原子数１ないし４のアルキル基を表すか；あるいはＲ₁₁およびＲ₁₂はそれらが結合する窒素原子と一緒になって、未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ハロメチル基もしくはニトロ基からなる系列からの同じかまたは異なる置換基により一ないし三置換された複素環を表す。〕で表される新規な有害生物活性化合物、または適当ならば、その互変異性体に関する。本発明はさらにまた、これらの化合物の製造方法；有効成分としてこれらの化合物の少なくとも１種を含む農薬組成物、ならびに農業または園芸における有効成分または有害生物防除剤、特に殺微生物剤としての使用法に関する。化合物Ｉならびに、適当ならばそれらの互変異性体は塩の形態で存在する。化合物Ｉが少なくとも１つの塩基中心をもつため、それらは例えば酸付加塩を形成できる。これらの塩は例えば、鉱酸例えば硫酸、燐酸もしくはハロゲン化水素酸によって；有機カルボン酸、例えば酢酸、シュウ酸、マロン酸、コハク酸、マレイン酸、フマル酸もしくはフタル酸によって；ヒドロキシカルボン酸例えばアスコルビン酸、乳酸、リンゴ酸、酒石酸もしくはクエン酸によって；または安息香酸によって；あるいは有機スルホン酸例えばメタンスルホン酸もしくはｐ−トルエンスルホン酸によって形成される。さらにまた、少なくとも１つの酸性基をもつ式Ｉの化合物は塩基と塩を形成できる。塩基との適当な塩は、例えばアルカリ金属塩またはアルカリ土類金属塩例えばナトリウム塩、カリウム塩またはマグネシウム塩、あるいはアンモニアとの塩または有機アミンとの塩であり、例えばモルホリン、ピペリジン、ピロリジン、モノ−、ジ−もしくはトリ−低級アルキルアミン例えばエチル−、ジエチル−、トリエチル−もしくはジメチルプロピルアミン、あるいはモノ−、ジ −もしくはトリヒドロキシ−低級アルキルアミン、例えばモノ−、ジ−もしくはトリエタノールアミンである。さらに相当する分子内塩もまた、可能な部分で形成できる。本発明の範囲内の好ましい塩は農薬学的に有利な塩である。他に定義しないかぎり、前述および後述に使用される一般的用語は以下に示された意味を表す。アルキル基は、炭素原子の数に依存して直鎖または枝分かれしたものであり、例えばメチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、第二ブチル基、イソブチル基、第三ブチル基、第二アミル基、第三アミル基、１ −ヘキシル基または３−ヘキシル基である。アルケニル基は、直鎖または枝分かれアルケニル基を意味すると理解されるべきであり、例えばアリル基、メタリル基、１−メチルビニル基またはブテ−２− エニ−１−イル基である，３ないし４個の炭素原子の鎖長を有するアルケニル基は好ましい。アルキニル基もまた、炭素原子の数に依存して直鎖または枝分かれが可能であり、例えば、プロパルギル基、ブチ−１−イニ−１−イル基またはブチ−１−イニ −３−イル基であってよい。プロパルギル基が好ましい。未置換の炭化水素基は３以下の多重結合をもつアルケニル基、アルキニル基またはアルケニニル基、例えば、ブタジエニル基、ヘキサトリエニル基、２−ペンテニ−４−イニル基である。ハロゲン原子またはハロ基は、フッ素原子、塩素原子、臭素原子またはヨウ素原子であり、好ましくは、フッ素原子、塩素原子または臭素原子である。ハロアルキル基は同じかまたは異なるハロゲン原子をもつことができ、言及しえる例はフルオロメチル基、ジフルオロメチル基、ジフルオロクロロメチル基、トリフルオロメチル基、クロロメチル基、ジクロロメチル基、トリクロロメチル基、２，２，２−トリフルオロエチル基、２−フルオロエチル基、２−クロロエチル基、２，２，２−トリクロロエチル基、３，３，３−トリフルオロプロピル基である。アルコキシ基、例えば、メトキシ基、エトキシ基、プロピルオキシ基、ｉ−プロピルオキシ基、ｎ−ブチルオキシ、イソ−ブチルオキシ基、第二ブチルオキシ基および第三ブチルオキシ基であり；好ましくはメトキシ基およびエトキシ基である。ハロアルコキシ基は、例えばジフルオロメトキシ基、トリフルオロメトキシ基、２，２，２−トリフルオロエトキシ基、１，１，２，２−テトラフルオロエトキシ基、２−フルオロエトキシ基、２−クロロエトキシ基および２，２−ジフルオロエトキシ基である。シクロアルキル基は環の大きさによって、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基またはシクロヘプチル基である。環状不飽和炭化水素基は、芳香族基、例えばフェニル基、ナフチル基、あるいは非芳香族基、例えばシクロペンテニル基、シクロヘキセニル基、シクロヘプテニル基およびシクロオクタジエニル基、あるいは部分的に芳香族の基、例えばテトラヒドロナフチル基およびインダニル基であってよい。アルカノイル基は各々の場合、含まれる炭素原子の数が考慮される直鎖または枝分かれしたいずれかである。可能な例は、ホルミル基、アセチル基、プロピオニル基、ブチリル基、ピバロイル基またはオクタノイル基である。アルコキシアルキル、アルキルチオアルキル、アルカンスルフィニルアルキル、アルカンスルホニルアルキル、ニトロアルキル、シアノアルキルおよびシアノアルカンスルホニルのような；アルコキシ−、アルキルチオ−、アルカンスルフィニル−、アルカンスルホニル−、ニトロ−またはシアノ置換炭素含有基および化合物では、これらの基および化合物がベースとする未置換の基本構造における水素原子の一つが、アルコキシ、アルキルチオ、アルカンスルフィニル、アルカンスルホニル、ニトロまたはシアノ基で置換されている。複素環基はヘテロ原子Ｎ、Ｏおよび／またはＳをもつ５−または６−員の、芳香族および非芳香族環と理解するべきである。さらにまた、未置換のまたは置換されたベンゾ基は残りの部分に結合した複素環基のように縮合できる。複素環基の例は、ピリジル基、ピリミジニル基、イミダゾリル基、チアゾリル基、１，３，４− チアジアゾリル基、トリアゾリル基、チエニル基、フラニル基、ピロリル基、モルホリニル基、オキサゾリル基および相当する部分的にまたは完全に水素化された環である。縮合ベンゾ基をもつ複素基の例はキノリル基、イソキノリル基、ベンゾキサゾリル基、キノキサリニル基、ベンゾチアゾリル基、ベンジミダゾリル基、インドリル基、インドリニル基である。前述した総ての列挙は例のためにあって限定のためではない。本発明の範囲内にある好ましい化合物を以下に示す：（１）式中、Ｒ₁₀が８個以下の炭素原子を有しおよび未置換であるかまたは１ないし５個のハロゲン原子、炭素原子数１ないし２のアルコキシ基、ヒドロキシル基、ニトロ基、シアノ基、炭素原子数１ないし４のアルカノイル基、ハロ−炭素原子数１ないし４のアルカノイル基もしくは炭素原子数１ないし４のアルコキシカルボニル基によって置換された、開鎖、飽和または不飽和炭化水素基；１０個以下の炭素原子数をもつ、環式、飽和もしくは不飽和炭化水素基；または炭素環が未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ハロメチル基、ニトロ基もしくはシアノ基により一もしくは二置換されたベンジル基；あるいは未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ハロメチル基、ニトロ基もしくはシアノ基からなる系列からの同じかまたは異なる置換基により一ないし三置換された複素環基あるいは５−ないし７−員ラクトン環を表す、式Ｉで表される化合物。（２）式中、Ｒ₁₀が、水素原子、１２個以下の炭素原子を有しおよび未置換であるかまたはトリ（炭素原子数１ないし４のアルキル）シリル基によりもしくはエポキシ基により置換された、開鎖、飽和または不飽和炭化水素基；あるいは、基：−ＣＨ（Ｕ）（ＣＨ₂）_mＣＯ−Ｗ〔式中、Ｕは水素原子、炭素原子数１ないし４のアルキル基、シアノ基または炭素原子数１ないし６のアルコキシカルボニル基を表し；Ｗは炭素原子数１ないし６のアルコキシ基、炭素原子数３ないし６のシクロアルコキシ基または基：−Ｎ（Ｔ₁）Ｔ₂を表し；ｍは０，１または２を表し；およびＴ₁およびＴ₂は、互いに独立して、水素原子；未置換であるかまたは１ないし３個のハロゲン原子、炭素原子数１ないし２のアルコキシ基、ヒドロキシル基、ニトロ基、シアノ基、炭素原子数１ないし４のアルカノイル基、ハロ−炭素原子数１ないし４のアルカノイル基もしくは炭素原子数１ないし４のアルコキシカルボニル基で置換された炭素原子数１ないし６のアルキル基あるいは未置換であるかまたは１ないし３個のハロゲン原子で置換された炭素原子数１ないし６のアルケニル基、未置換であるかまたは１ないし３個のハロゲン原子で置換された炭素原子数１ないし６のアルキニル基；１０個以下の炭素原子数をもつ、環式、飽和もしくは不飽和炭化水素基；または炭素環が未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ハロメチル基、ニトロ基もしくはシアノ基により一もしくは二置換されたベンジル基；あるいは未置換であるかまたは炭素原子数１ないし２のアルキル基、ハロゲン原子、ハロメチル基、ニトロ基もしくはシアノ基からなる系列からの同じかまたは異なる置換基により一ないし三置換された複素環基を表すか；あるいはＴ₁およびＴ₂はそれらが結合する窒素原子と一緒になってさらに環原子としてＯ、Ｓおよび／またはＮを持つことができる５ないし７−員の複素環（該複素環において、追加の窒素は未置換であるかまたは炭素原子数１ないし４のアルキル基、フェニル基、炭素原子数１ないし４のアルカノイル基、ベンゾイル基またはベンジル基により置換されており、ならびに該複素環の炭素原子は未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ハロメチル基もしくはニトロ基からなる系列からの同じかまたは異なる置換基により一ないし三置換されている。）を形成する。〕を表す、式Ｉで表される化合物。（３）式中、Ｒ₁₀が水素原子、６個以下の炭素原子を有しおよび未置換であるかまたはトリ（炭素原子数１ないし４のアルキル）シリル基によりもしくはエポキシ基により置換された、開鎖、飽和または不飽和炭化水素基；あるいは、基：− ＣＨ₂−ＣＯ−Ｗ〔式中、Ｗは炭素原子数１ないし６のアルコキシ基、炭素原子数３ないし６のシクロアルコキシ基または基：−Ｎ（Ｔ₁）Ｔ₂を表し；Ｔ₁およびＴ₂は互いに独立して水素原子、炭素原子数１ないし６のアルキル基、１ないし３個のハロゲン原子を有するハロ−炭素原子数１ないし６のアルキル基、炭素原子数３ないし６のシクロアルキル基、フェニル基、１ないし３個のハロゲン原子を有するハロ−フェニル基、ピリジル基、ナフチル基を表し；あるいはＴ₁およびＴ₂はそれらが結合する窒素原子と一緒になってピペリジン、ピペラジン、モルホリンまたは２，６−ジメチルモルホリンを表す。〕を表す、式Ｉで表される化合物。（４）式中、Ｒ₁は水素原子または炭素原子数１ないし４のアルキル基を表し；Ｒ₂は水素原子、炭素原子数１ないし４のアルキル基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルコキシ−炭素原子数１ないし４のアルキル基、シクロプロピル基、エチニル基またはハロゲン原子を表し；Ｒ₃はフッ素原子または塩素原子を表し；Ｒ₄は水素原子または炭素原子数１ないし４のアルキル基を表し；Ｒ₅は炭素原子数１ないし４のアルキル基を表し；Ｒ₆が水素原子を表し；Ｒ₇が水素原子またはハロゲン原子を表し；ＸがＯＲ₁₀、ＳＲ₁₀またはＮ（Ｒ₁₁）Ｒ₁₂を表し；Ｒ₁₀が炭素原子数１ないし４のアルキル基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルコキシ−炭素原子数１ないし４のアルキル基、ヒドロキシ−炭素原子数１ないし４のアルキル基、ニトロ−炭素原子数１ないし４のアルキル基、シアノ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルカノイル−炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルコキシカルボニル− 炭素原子数１ないし４のアルキル基；未置換であるかまたはハロゲン原子で一ないし三置換された炭素原子数２ないし４のアルケニル基；炭素原子数２ないし４のアルキニル基、炭素原子数３ないし７のシクロアルキル基、炭素原子数４ないし８のシクロアルケニル基、ベンジル基；未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ニトロ基もしくはシアノ基で一ないし二置換されたフェニル基；またはピリジン基、ピリミジン基またはトリアジン基（これらの複素環は未置換であるかまたは、おのおのハロゲン原子、炭素原子数１ないし２のアルキル基、トリフルオロメチル基もしくはシアノ基からなる系からの同じかまたは異なる基により一ないし三置換される。）か、あるいは５員ラクトン環を表し；Ｒ₁₁は水素原子、炭素原子数１ないし４のアルキル基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルコキシ−炭素原子数１ないし４のアルキル基、ヒドロキシ−炭素原子数１ないし４のアルキル基、ニトロ−炭素原子数１ないし４のアルキル基、シアノ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルカノイル−炭素原子数１ないし４のアルキル基、炭素原子数１ないし４のアルコキシカルボニル−炭素原子数１ないし４のアルキル基；未置換であるかまたはハロゲン原子で一ないし三置換された炭素原子数２ないし４のアルケニル基；炭素原子数２ないし４のアルキニル基、炭素原子数３ないし７のシクロアルキル基、炭素原子数４ないし８のシクロアルケニル基、ベンジル基；未置換であるかまたはハロゲン原子、炭素原子数１ないし２のアルキル基、ニトロ基もしくはシアノ基で一ないし二置換されたフェニル基を表し；Ｒ₁₂は水素原子または炭素原子数１ないし４のアルキル基を表すか；またはＲ₁₁およびＲ₁₂はそれらが結合している窒素原子と一緒になってピロリジン基、ピペリジン基、ピペラジン基、モルホリン基または２，６−ジメチルモルホリン基を表す、式Ｉで表される化合物。（４）に基づいて言及するべき化合物のうちの好ましい基のものはさらに以下に示すものである：（４．１）式中、ＸがＳＲ₁₀である化合物。（４．２）式中、ＸがＯＲ₁₀である化合物。（５）式中、Ｒ₁が水素原子または炭素原子数１ないし４のアルキル基を表し；Ｒ₂が水素原子、炭素原子数１ないし４のアルキル基、１、２もしくは３個のハロゲン原子を有するハロ−炭素原子数１ないし４のアルキル基、炭素原子数１ないし２のアルコキシ基−炭素原子数１ないし４のアルキル基、シクロプロピル基、エチニル基またはハロゲン原子を表し；Ｒ₃が塩素原子を表し；Ｒ₄が水素原子または炭素原子数１ないし４のアルキル基を表し；Ｒ₅が炭素原子数１ないし４のアルキル基を表し；Ｒ₆が水素原子を表し；Ｒ₇が水素原子を表し；ＸがＯＲ₁₀またはＳＲ₁₀を表し；Ｒ₁₀が基：−ＣＨ₂−ＣＯ−Ｗを表し；Ｗが炭素原子数１ないし６のアルコキシ基、炭素原子数３ないし６のシクロアルコキシ基、または基−Ｎ（Ｔ₁）Ｔ₂を表し；Ｔ₁およびＴ₂は、互いに独立して、水素原子、炭素原子数１ないし６のアルキル基、１ないし３個のハロゲン原子を有するハロ−炭素原子数１ないし６のアルキル基、炭素原子数３ないし６のシクロアルキル基、フェニル基、１ないし３個のハロゲン原子を有するハロフェニル基、ピリジル基、ナフチル基を表すか、あるいはＴ₁およびＴ₂はそれらが結合している窒素原子と一緒になってピペリジン基、ピペラジン基、モルホリン基または２，６−ジメチルモルホリン基を表す、式Ｉで表される化合物。（６）次式Ｉ．１〔式中、Ｒ₂は水素原子、メチル基またはエチル基を表し；Ｒ₃はフッ素原子または塩素原子を表し；Ｒ₅はメチル基またはエチル基を表し；Ｒ₇は水素原子またはフッ素原子を表し；ＸはＯＲ₁₀、ＳＲ₁₀またはＮ（Ｒ₁₁）Ｒ₁₂を表し；Ｒ₁₀は炭素原子数１ないし４のアルキル基、ジフルオロメチル基、トリフルオロメチル基、２−フルオロエチル基、２，２，２−トリフルオロエチル基、ビニル基、アリル基、２−プロピニル基、シクロペンチル基、シクロヘキシル基、シクロヘキセニル基、シアノメチル基または炭素原子数１ないし４のアルコキシカルボニルメチル基を表し；Ｒ₁₁は水素原子、炭素原子数１ないし４のアルキル基、シクロヘキシル基、シクロプロピル基またはフェニル基を表し；Ｒ₁₂は水素原子を表し；またはＲ₁₁およびＲ₁₂はそれらが結合している窒素原子と一緒になって、ピペリジン基、モルホリン基または２，６−ジメチルモルホリン基を表す。）で表される化合物。（７）式Ｉ．２（式中、Ｒ₂は水素原子、メチル基またはエチル基を表し；Ｒ₃はフッ素原子または塩素原子を表し；Ｒ₅はメチル基またはエチル基を表し；Ｒ₇が水素原子またはフッ素原子を表し；ＸはＯＲ₁₀、ＳＲ₁₀またはＮ（Ｒ₁₁）Ｒ₁₂を表し；Ｒ₁₀は炭素原子数１ないし４のアルキル基、ジフルオロメチル基、トリフルオロメチル基、２−フルオロエチル基、２，２，２−トリフルオロエチル基、ビニル基、アリル基、２−プロピニル基、シクロペンチル基、シクロヘキシル基、シクロヘキセニル基、シアノメチル基または炭素原子数１ないし４のアルコキシカルボニルメチル基を表し；Ｒ₁₁は水素原子、炭素原子数１ないし４のアルキル基、シクロヘキシル基、シクロプロピル基またはフェニル基を表し；Ｒ₁₂は水素原子を表し；またはＲ₁₁およびＲ₁₂はそれらが結合している窒素原子と一緒になって、ピペリジン基、モルホリン基または２，６−ジメチルモルホリン基を表す。）で表される化合物。（８）式Ｉ．１ａ（式中、Ｒ₁₀は未置換であるかまたはハロゲン原子により一ないし三置換された炭素原子数１ないし５のアルキル基、または未置換であるかまたはハロゲン原子により一ないし三置換された炭素原子数２ないし５のアルケニル基を表す。）で表される化合物。それぞれの場合遊離形態または塩形態の、式Ｉで表される化合物ならびに、適当ならばその互変異性体は以下に示すように製造できる：（Ａ）ａ）ＸがＳＲ₁₀である、式Ｉで表される化合物を製造するために：式II （式中、置換基Ａは６もしくは７−位にあり、ならびにＲ₁ないしＲ₇は式Ｉで定義されたものと同じである。）で表される化合物と式III Ｒ₁₀−Ｚ（III）（式中、Ｒ₁₀は式Ｉで定義されたと同じ意味を表し、およびＺは容易に脱離するヌクレオフュージック基(nucleofugic radical)を表す。）で表される化合物とを、好ましくは塩基の存在下で反応させるが、特に好ましくはまず式IIで表される化合物と塩基とを反応させ、次いで式IIIで表される化合物を反応させるか；あるいはｂ）ＸがＯＲ₁₀またはＮ（Ｒ₁₁）Ｒ₁₂である式Ｉで表される化合物を製造するために：ＸがＳＲ₁₀である式Ｉで表される化合物と、式IV Ｍ−Ｘ（IV）（式中、Ｍは水素原子、Ｌｉ⁺、Ｎａ⁺、Ｋ⁺、1/2Ｍｇ²⁺または第四級アンモニウムイオンを表し；ＸはＯＲ₁₀またはＮ（Ｒ₁₁）Ｒ₁₂を表しおよびＲ₁₀、Ｒ₁₁およびＲ₁₂は式Ｉで定義されたと同じ意味を表す。）で表される化合物とを、適当ならば塩基の存在下で反応させるか、あるいはｃ）Ｒ₄が式Ｉで定義されたものと同じであるが、水素原子以外である式Ｉで表される化合物を製造するため：Ｒ₄が水素原子である、式Ｉで表される化合物と式ＶＲ₄’−Ｚ’ （Ｖ）（式中、Ｒ₄’は式ＩでＲ₄に対して定義されたものと同じであるが、水素原子以外を表しおよびＺ’は容易に脱離するヌクレオフュージック基を表す。）で表される化合物とを、好ましくは塩基の存在下で、反応させる。（Ｂ）式VII （式中、置換基Ａは６もしくは７−位にあり、ならびにＲ₁ないしＲ₇は式Ｉで定義されたものと同じである。）で表される化合物と、オキシ塩化燐、塩化チオニルまたは塩化スルフリルとを反応させて、式VIII で表される化合物を得て、そしてこの化合物を式IV’ Ｍ−Ｘ’ （IV’）（式中、Ｍは水素原子、Ｌｉ⁺、Ｎａ⁺、Ｋ⁺、1/2Ｍｇ²⁺または第四級アンモニウムイオンを表し；Ｘ’はＯＲ₁₀、ＳＲ₁₀またはＮ（Ｒ₁₁）Ｒ₁₂を表しおよびＲ₁₀、Ｒ₁₁およびＲ₁₂ は式Ｉで定義されたと同じ意味を表す。）で表される化合物とを、適当ならば塩基の存在下で反応させる。（Ｃ）式IX （式中、置換基Ａは６もしくは７−位にあり、ならびにＲ₁ないしＲ₇は式Ｉで定義されたものと同じである。）で表される化合物と、酸化剤とを反応させる。適当な酸化剤の例は、鉄（III）塩、ＳｅＯ₂、ＭｎＯ₂、Ｈ₂Ｏ₂、Ｂｒ₂、Ｃｌ₂ 、Ｉ₂、ＳＯ₃、Ｈ₂ＳＯ₄、ＨＮＯ₃、Ｎ−ブロモスクシンイミド、２，３−ジクロロ−５，６−ジシアノ−１，４−ベンゾキノンまたは脱水素化触媒の存在下のＯ₂である。（Ｄ）式IX’ （式中、置換基Ａは６もしくは７−位にあり、ならびにＲ₁ないしＲ₇およびＸは式Ｉで定義されたものと同じでありおよびＺは容易に脱離できるヌクレオフュージック基である。）で表される化合物から、塩基または酸の存在下、ＨＺを脱離させる。前述および後述に記載された反応はそれ自体公知の方法、例えば適当な溶媒または稀釈剤あるいはそれらの混合物の不在下、または都合良くは存在下で行われ；上記方法は例えば、おおよそ−８０℃ないし反応媒体の沸点の、好ましくはおおよそ−２０℃ないしおおよそ＋１５０℃の温度範囲で、適当には冷却しながら、室温で、または加熱しながら；必要ならば密封した容器中、加圧下で、不活性ガス雰囲気中、および／または無水条件下で行われる。代表的な反応条件は実施例に見い出すことができる。ヌクレオフュージック基ＺまたはＺ’の例は：フッ素原子、塩素原子、臭素原子、ヨウ素原子、メチルチオ基、エチルチオ基またはプロピルチオ基のような炭素原子数１ないし８のアルキルチオ基；アセトキシ基のような炭素原子数１ないし８のアルカノイルオキシ基；メタンスルホニルオキシ基、エタンスルホニルオキシ基またはトリフルオロメタンスルホニルオキシ基のような（ハロ−）炭素原子数１ないし８のアルカンスルホニルオキシ基；またはベンゼンスルホニルオキシ基またはｐ−トルエンスルホニルオキシ基のような置換されたまたは未置換のフェニルスルホニルオキシ基、およびさらにまたヒドロキシル基である。適当な塩基は、例えばアルカリ金属またはアルカリ土類金属の水酸化物、水素化物、アミド、アルカノレート、炭酸塩、ジアルキルアミドまたはアルキルシリルアミド、またはアルキルアミン、アルキレンジアミン、遊離もしくはＮ−アルキル化飽和もしくは不飽和シクロアルキルアミン、塩基性複素環式化合物類、水酸化アンモニウムおよび炭素環式アミンである。言及され得る例は水酸化ナトリウム、水素化ナトリウム、ナトリウムアミド、ナトリウムメタノレート、炭酸ナトリウム、カリウム第三ブタノレート、炭酸カリウム、リチウムジイソプロピルアミド、カリウムビス（トリメチルシリル）アミド、水素化カルシウム、トリエチルアミン、トリエチレンジアミン、シクロヘキシルアミン、Ｎ−シクロヘキシル−Ｎ，Ｎ−ジメチルアミン、Ｎ，Ｎ−ジエチルアニリン、ピリジン、４− （Ｎ，Ｎ−ジメチルアミノ）ピリジン、Ｎ−メチルモルホリン、ベンジルトリメチルアンモニウムヒドロキシドならびに１，５−ジアザビシクロ〔５．４．０〕ウンデセ−５−エン（ＤＢＵ）である。反応体はそのまま互いに、すなわち溶媒または希釈剤を添加せずに、例えば溶融体で反応させ得る。しかしながら、多くの場合において、不活性な溶媒もしくは希釈剤またはその混合物を添加することが有利である。言及され得るそのような溶媒または希釈剤の例は、芳香族、脂肪族および脂環式炭化水素およびハロ炭化水素、例えば、ベンゼン、トルエン、キシレン、クロロベンゼン、ジクロロベンゼン、ブロモベンゼン、石油エーテル、ヘキサン、シクロヘキサン、ジクロロメタン、トリクロロメタン、テトラクロロメタン、ジクロロエタンまたはトリクロロエタン；エーテル、例えば、ジエチルエーテル、第三ブチルメチルエーテル、テトラヒドロフランまたはジオキサン；ケトン、例えば、アセトンまたはメチルエチルケトン；アルコール、例えばメタノール、エタノール、プロパノール、ブタノール、エチレングリコールまたはグリセロール；エステル、例えば酢酸エチルまたは酢酸ブチル；アミド、例えばＮ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、Ｎ−メチルピロリドンまたはヘキサメチルリン酸トリアミド；ニトリル、例えば、アセトニトリル；およびスルホキシド、例えばジメチルスルホキシドである。過剰に使用される塩基、例えばトリエチルアミン、ピリジン、Ｎ−メチルモルホリンまたはＮ，Ｎ−ジエチルアニリンは溶媒または希釈剤としてもまた作用し得る。反応は約０℃ないし約＋１８０℃、好ましくは約＋２０℃ないし約＋１３０℃ の温度範囲で、多くの場合使用される溶媒の還流温度の間の範囲で有利に行われる。代わりに、反応は有機溶媒、例えば塩化メチレンまたはトルエン中、水性アルカリ溶液、例えば水酸化ナトリウムの存在下および相転移触媒例えば硫酸水素テトラブチルアンモニウムの存在下で、相転移触媒作用を用いて行われ得る。本発明に従ってまたは他の経路により得られうる化合物または、適当ならばこの化合物の互変異性体は、それ自体公知の方法で、他の置換基により慣用の方法で出発する化合物Ｉの１またはそれ以上の置換基を置き換えることによって、他の化合物Ｉに変換できる。例えば、 − ハロゲン原子を含まない置換基、または非ハロゲン化芳香族もしくはヘテロ芳香族の環の部分−構造はハロゲン化されて、ハロゲン含有置換基、またはハロゲン化芳香族もしくはヘテロ芳香族の環の部分−構造が得られる。 − ハロゲン置換基はシアノ、アルキルチオまたはアルコキシ置換基のような他の置換基に交換できる。 − アルカノイル基、ベンゾイル基またはスルホニル置換基は容易に交換できる水素に交換し得る。 − Ｎ−水素はＮ−アルキル、Ｎ−ベンジル、Ｎ−アリール、Ｎ−ヘテロアリール、Ｎ−アルカノイル、Ｎ−ベンゾイルまたはＮ−スルホニル基に交換可能である。 − スルフィドは酸化されてスルホキシドおよびスルホンを与える。 − カルボニル基は硫酸化されてチオカルボニル基を与える。本発明は可能な上記純粋な異性体および総ての異性体混合物に関する。本発明はまた、式Ｉで表される化合物の製造のために使用される新規な出発物質および中間体、それらの使用法およびそれらの製造方法にも関する。式II、VIIおよびIXで表される化合物は以下の化学反応式に示すような公知の方法で製造できる。この化学式では、Ａ、Ｒ₁₀、Ｚ、ＭおよびＸは上記に定義したと同じ意味である。以下に示すのは酸化剤として適当なものである：鉄（III）塩、ＳｅＯ₂、ＭｎＯ₂、Ｈ₂Ｏ₂、Ｂｒ₂、Ｃｌ₂ 、Ｉ₂、ＳＯ₃、Ｈ₂ＳＯ₄、ＨＮＯ₃、Ｎ−ブロモスクシンイミド、ベンゾキノン例えば、２，３−ジクロロ−５，６−ジシアノ−１，４−ベンゾキノン（ＤＤＱ）または脱水素触媒の存在下でのＯ₂である。加硫剤（thionating agents）の例は、五硫化リンまたは２，４−ビス（４−メトキシフェニル）−１，３−ジチア −２，４−ジホスフェタン−２，４−ジスルフィド〔「ローエッソン試薬(Lawes son's reagent)」〕である。式IX，IX’，XIおよびXIIで表される化合物の製造は、例えばスイス特許出願第509/93-0号（出願日：1993年２月18日）、第617/93-3号（出願日：1993年３月２日）および第1788/93-2号（出願日：1993年６月16日）に記載されている。式III、IV、ＶおよびVIで表される化合物は公知であるかまたは公知の方法により製造できる。４位においてアミノ置換されたピリミジンは例えば国際公開第92/08704号特許出願に既に開示されている。本発明の化合物Ｉは特質においてこれらの公知の化合物と構造的に異り；さらに本発明の式Ｉの化合物は予期できない強力な殺微生物、殺虫、殺線虫および殺ダニ活性をもつ。植物の保護は有害生物において直接作用によりおよびまた植物の防御系（免疫）を活性化しおよび刺激することにより生じる。式Ｉの化合物は、農業の部門においておよび関連する分野において、植物の有害生物を防除するための有効成分として使用できる。本発明による前記有効成分は低い濃度割合における強力な活性によりおよびそれらが植物にとって十分許容性のあるものでありおよび環境に優しいという事実により特徴づけられる。それらは非常に有利な治療特性、予防特性および浸透特性を持ち、そして非常に多くの栽培植物の保護に対して使用できる。式Ｉの有効成分を使用して、有益植物の種々な作物における植物および植物の部位（果実、花、葉、茎、塊茎、根）に見出される有害生物を防除、または破壊することができ、さらに生育の後の段階で生成した植物の部位でさえも例えば植物病原性微生物による損傷を免れたままにある。式Ｉの化合物はさらに、真菌性感染ならびに土壌起源の植物病原性真菌に対する保護のため、植物繁殖材料特に、種子（果実、塊茎、穀粒）および植物の苗木（例えば稲）の処理のための種子粉衣剤（seed dressing agents）としてもまた使用できる。式Ｉの化合物は例えば以下の菌に属する植物病原性菌対して有効である：不完全菌類〔例えば、ボトリチス属(Botrytis)、ピリキュラリア属(pyricularia)、ヘルミンントススポリウム属(Helminthosporium)、フザリウム属(Fuzarium)、セプトリア属(Septoria)、セルコスポラ属（Cercospora）およびアルナアリア属(A lternaria)〕および；担子菌類〔例えば、リゾクトニア属(Rhizoctonia)、ヘミレイア属(Hemileia)、プシニア属（Puccinia ）〕である。さらにそれらは嚢子菌類〔例えばベンチュリア（Venturia）属ならびにエリシフェ属（Brysiphe）、ポドスファエラ属(Podosphaera)、モニリニア属(Monilinia)、アンシヌラ属(Uncinula)〕ならびに卵菌類〔例えばフィトフトラ属(Phytophthora)、ペロノスポラ属(Peronospora)、ピシウム属(Pythium)プラスモパラ属（Plasmopara）〕の菌の類に対して有効である。さらにまた、本発明による化合物Ｉは、農業的作物植物および鑑賞植物、特に綿、野菜および果実植物における、森林における、貯蔵製品および材料の保護におけるおよび衛生部門におけるダニ目(Acarina)および昆虫および線虫綱の有害生物、ならびに例えば家畜および生産家畜のような動物の有害生物を防除するための種々の有効成分である。それらは、種々の発育段階に対して活性がある。これらの活性は有害生物を直ちに殺害または、例えば脱皮期に際して、ほんの数時間後殺害することから、あるいは著しく減少した産卵および／または孵化率から明らかになる。ダニ目は例えばブーフィルス種(Boophilus spp.)およびテトラニクス種(Tetranychus spp.)を含み、線虫類は例えばヘテロデラ・グリシンズ(Het erodera glysines)を含み、および昆虫類は例えばニラバルヴァタ・ルゲンス(Ni laparvata lugens)、プルテラ・キソステラ(Plutella xylostella)およびムスカ・ドメスティカ(Musca domestica)を含む。本発明の範囲にある、作物保護の用途のための目的作物は例えば以下の植物のタイプである：穀類（小麦、大麦、ライ麦、オート麦、米、トウモロコシ、ソルガムおよび関連種）；ビート（砂糖および飼料用ビート）；梨状果、核果および軟果実（リンゴ、梨、プラム、桃、アーモンド、サクランボ、イチゴ、ラズベリーおよびブラックベリー）；マメ科植物（ソラ豆、レンズ豆、エンドウ豆、大豆）；油用植物（アブラナ、マスタード、ポピー、オリーブ、サンフラワー、ココナッツ、ヒマシ油植物、ココア豆、落花生）；ウリ科植物（カボチャ、キュウリ、メロン）；繊維植物（綿、亜麻、大麻、黄麻）；橙属植物（オレンジ、レモン、グレープフルーツ、マンダリン）；野菜（ホウレンソウ、レタス、アスパラガス、キャベツ、ニンジン、玉葱、トマト、ジャガイモ、トウガラシ）；クスノキ科（アボガド、シナモン、樟脳）；および、タバコ、ナッツ、コーヒー、サトウキビ、茶、コショウならびにブドウの木、ホップ、ナス、バショウ科、天然ゴム植物ならびに観賞植物のような他の種の植物。式Ｉの有効成分は通常組合せの形態で施用され、および処理されるべき作地または植物に、同時にまたはそれに引き続いて別の有効成分と共に施用しうる。他の有効成分は例えば肥料、微量元素供給体あるいは植物成長に影響する他の製剤であってよい。使用できる他の物質は選択的除草剤ならびに殺虫剤、殺真菌剤（ fungicides）、殺菌剤(bactericides)、線虫駆除剤、軟体動物駆除剤またはこれらの製剤のいくつかの混合物であり、適当ならば製剤業界にて慣用的に使用される他の担体、表面活性剤または施用増強補助剤と共に使用することもできる。適当な担体および補助剤は固体または液体であり、そして製剤業界で都合よく使用される物質、例えば天然または再生鉱物物質、溶媒、分散剤、水和剤、固着剤(adhesives)、増粘剤、結合剤または肥料である。式Ｉで表される有効成分またはこれらの有効成分の少なくとも１種を含む農薬組成物の好ましい施用法は、葉への施用である（茎葉散布）。施用の回数および施用の割合は問題となる病原による攻撃の危険性に依存する。代わりに、式Ｉの有効成分はまた、液体組成物で植物の作地に含浸させるか、或いは固体の形態、例えば粒剤の形態で土壌に物質を混合すること（土壌施用）により、根系を介して土壌から植物に到達することも可能である（浸透作用）。水稲〔パディライス (paddy rice)〕の場合、このような粒剤は浸水した田の中へ計量して入れることが可能である。しかしながら、式Ｉの化合物はまた、有効成分を含む液体製剤で穀粒(kernels)または塊茎を含浸させるか、あるいは固体製剤でそれらにコーティングするかによって、種粒に施用される（被覆）。式Ｉの化合物はそのままの形体で、あるいは好ましくは製剤業界で慣用の補助剤と共に使用される。この目的のため、それらは、例えば乳剤原液、塗布可能ペースト、直接噴霧可能な又は希釈可能な溶液、希釈乳剤、水和剤、水溶剤、粉剤、粒剤および例えば、ポリマー物質によるカプセル化剤に示される公知の方法により都合良く加工される。施用法例えば、噴霧、霧化、散粉、散水、塗布(brush)または注水、ならびに組成物の性質は意図する目的および使用環境に合わせて選ばれる。都合のよい施用割合は通常１ヘクタール(ha)当たり有効成分（A.I.）５ｇないし２ｋｇ、好ましくは１０ｇないし１ｋｇ A.I.／ｈａ、そして特に好ましくは２０ｇないし６００ｇ A.I.／ｈａである。種子粉衣として使用される場合、種子１ｋｇ当り有効成分１０ｍｇないし１ｇの施用割合が都合良く使用される。製剤、即ち式Ｉの有効成分、および所望ならば、固体又は液体の補助剤を含む組成物、配合物または組合せ剤は公知の方法、例えば有効成分を増量剤例えば、溶媒（混合物）、固体担体材料ならびに、適当ならば表面活性化合物（界面活性剤）と共に緊密に混合および／または粉砕することにより製造される。次に示すものが溶媒として使用可能である：芳香族炭化水素、好ましくは炭素原子数８ないし１２の部分、例えばキシレン混合物または置換されたナフタレン、ジブチルフタレートもしくはジオクチルフタレートのようなフタル酸エステル；脂肪族炭化水素例えばシクロヘキサンまたはパラフィン；アルコールおよびグリコールならびにそれらのエーテルおよびエステル、例えばエタノール、エチレングリコール、エチレングリコールモノメチルエーテルもしくはエチレングリコールモノエチルエーテル；ケトン、例えばシクロヘキサノン；強極性溶媒、例えばＮ−メチル−２−ピロリドン、ジメチルスルホキシドまたはジメチルホルムアミド；ならびにエポキシ化もしくは非エポキシ化植物油、例えば、エポキシ化ココナッツ油または大豆油；および水。例えば、粉剤および分散性粉末に使用される固体担体は通常、方解石、タルク、カオリン、モンモリロナイトまたはアタパルジャイトのような天然鉱物である。物性を改良するために、高分散ケイ酸または高分散吸収性ポリマーを加えることも可能である。適当な粒状化吸着性担体は多孔性型のもので、例えば軽石、破壊レンガ、セピオライトまたはベントナイトであり、または非吸収性担体は例えば、方解石または砂のような物質である。さらに非常に多くの粒状化した無機質および有機質の物質、例えば特にドロマイトまたは粉状化植物残骸を使用し得る。製剤化された式Ｉの化合物の性質により、適当な界面活性化合物は、良好な乳化、分散および水和性を有する非イオン性、陽イオン性および／又は陰イオン性界面活性剤である。界面活性剤はまた界面活性剤の混合物も意味するものと理解すべきである。適当な陰イオン性界面活性剤はいわゆる水溶性石ケンまたは水溶性合成界面活性化合物である。言及するべき非イオン性界面活性剤の例は、ノニルフェノールポリエトキシエタノール、ヒマシ油ポリグリコールエーテル、ポリプロピレン／ポリエチレンオキシド付加物、トリブチルフェノキシポリエトキシエタノール、ポリエチレングリコールおよびオクチルフェノキシポリエトキシエタノールである。さらに、ポリオキシエチレンソルビタンの脂肪酸エステル、例えばポリオキシエチレンソルビタントリオレートもまた適当である。陽イオン性界面活性剤は、主に、Ｎ−置換基として少なくとも一つの炭素原子数８ないし２２のアルキル基と他の置換基として未置換またはハロゲン化低級アルキル基、ベンジル基、または低級ヒドロキシアルキル基とを含む第四級アンモニウム塩である。製剤業界で慣用に使用される界面活性剤は、当業者間で公知のものであり、または関連した専門文献で見出すことができる。農薬製剤は一般に、式Ｉの有効成分を０．１ないし９９重量％、特に０．１ないし９５重量％、固体または液体の補助剤９９．９ないし１重量％、特に９９．８ないし５重量％、および表面活性剤０ないし２５重量％、特に０．１ないし２５重量％を含む。濃縮された組成物は市販品としてしばしば好ましいが、最終消費者は通常希釈組成物を使用するであろう。該組成物はまた、特別な効果を成すために安定剤、消泡剤、粘度調節剤、結合剤、固着剤ならびに肥料または他の有効成分を含むこともできる。以下の実施例は上述した本発明についてその範囲を限定することなく本発明を説明する。温度はセ氏で表記する。以下の略字を使用する：Ａｃ＝アセチル；Ｅｔ＝エチル；ｉ−Ｐｒ＝イソプロピル；Ｍｅ＝メチル；Ｐｈ＝フェニル；Ｐｒ＝ｎ−プロピル；Ｂｕ＝ｎ−ブチル；ｍ．ｐ．＝融点；ｄｓ＝ジアステレオマー；ｒｅｇ＝位置異性体。「ＮＭＲ」は「核磁気共鳴スペクトル」を意味し；「ＭＳ」＝マススペクトルである。適切な濃度を示すために異なる単位を使用しない限り「％」は「重量％」を意味する。本発明による化合物の製造のための実施例実施例Ｈ-1a：７−［１−（５−クロロ−６−エチルピリジミン−４−イルアミノ）エチル］−３，４−ジヒドロ−２−メチルチオキノリン０．９ｇおよび２，３−ジクロロ−５，６−ジシアノ−１，４−ベンゾキノン（ＤＤＱ）０．８６ｇをスルホン化フラスコ中で無水ジオキサン２０ｍｌに室温で導入しそして混合物を８５−９０℃でおおよそ６時間攪拌する。冷却後、混合物を酢酸エチル１００ｍｌおよび水３０ｍｌで稀釈し、有機相を分離し、次に水相を酢酸エチルで２回抽出する。有機相を硫酸ナトリウムを用いて乾燥させ、溶媒を水ポンプの減圧下で蒸留により除去し、そして残渣をシリカゲルによるカラムクロマトグラフィー（溶離液：ｎ−ヘキサン／テトラヒドロフラン３：１）によって精製する。７−［１−（５−クロロ−６−エチルピリジミン−４−イルアミノ）エチル］−２−メチルチオキノリン０．６ｇが白色粉末（ｍ．ｐ．８２−８４℃）の形態で得られる。実施例Ｈ-1aに記載された手順と同様に製造できるかまたは上記手順の１つを使用して製造できる他の化合物を以下の表に列挙する。式Ｉの有効成分の配合実施例実施例Ｆ-1.1ないしＦ-1.3：乳剤原液あらゆる所望の濃度の乳剤が、この原液を水で希釈することによって得られる。実施例Ｆ-2：乳剤原液あらゆる所望の濃度の乳剤が、この原液を水で希釈することによって得られる。実施例Ｆ-3.1ないしＦ-3.4：溶液溶液は微小滴の形態での施用に適する。実施例Ｆ-4.1ないしＦ-4.4：粒剤本発明の有効成分をジクロロメタンに溶解し、溶液を担体上に噴霧し、次いで溶媒を真空で蒸発させる。実施例Ｆ-5.1ないしＦ-5.2：粉剤そのまま使用できる粉剤が、総ての成分を均質に混合することにより得られる。実施例Ｆ-6.1ないしＦ-6.3：水和剤総ての成分を混合し、混合物を適当なミルで十分に粉砕し、水で希釈されてあらゆる所望の濃度の懸濁液を与え得る水和剤を得る。生物学実施例：Ａ．殺微生物活性実施例Ｂ−１：小麦におけるプシニア・グラミニス(Puccinia graminis)に対する活性ａ）残留−保護活性播種６日後、小麦植物を、有効成分の水和剤により調製した水性噴霧混合物（有効成分０．２％）で滴る時点まで噴霧しそして２４時間後、植物を菌の夏胞子懸濁液で感染させる。４８時間の保温時間（環境：２０℃、９５〜〜１００％の相対大気湿度）後、植物を、２２℃の温室中に置く。感染１２日後、真菌の侵攻 (infestation)を評価する。ｂ）浸透活性播種５日後、有効成分の水和剤により調製した水性噴霧混合物（土壌容量に関し有効成分０．００６％）を小麦植物の周囲に注ぐ。噴霧混合物が植物の地上部に触れないように注意する。４８時間後、植物を菌の夏胞子懸濁液で感染させる。４８時間の保温時間（環境：２０℃、９５〜１００％の相対大気湿度）後、植物を、２２℃の温室中に置く。感染１２日後、真菌の侵攻を評価する。表１および２の化合物は良好な活性を示す。実施例Ｂ−２：トマトにおけるフィトフトラ・インフェスタンス(Phytophthora infestans)に対する活性ａ）残留保護活性トマト植物を３週間生長させ、そして有効成分の水和剤により調製した水性噴霧混合物（有効成分０．０２％）で滴る時点まで噴霧しそして２４時間後、菌の胞子嚢懸濁液に感染させる。真菌の侵攻は感染から、期間中相対大気湿度９０ないし１００％および２０℃の温度に保持された５日間の後に評価される。ｂ）浸透活性トマト植物を３週間成長させ、次に有効成分の水和剤により調製した水性噴霧混合物（土壌容量に基づき有効成分０．００６％）をそれらの周囲に注ぐ。噴霧混合物が植物の地上部に触れないように注意する。４８時間後、植物を胞子嚢懸濁液で感染させる。真菌の侵攻は感染から、期間中相対大気湿度９０ないし１００％および２０℃の温度に保持された５日間の後に評価される。表１および２の化合物は良好な活性を示す。実施例Ｂ−３：落花生におけるセルコスポラ・アラキディコラ(Cercospora arac hidicola)に対する活性１０〜１５ｃｍの高さの落花生植物を、有効成分の水和剤配合物で調整された噴霧混合液（有効成分の０．０２％）で滴る時点まで噴霧し、そして４８時間後、菌の分生子懸濁液で感染させる。植物を約２１℃および高湿度で７２時間保温し、そして続いて典型的な病変が生じるまで、温室中に置く。有効成分の活性は感染１２日後病変の数および大きさに基いて評価される。表１および２の化合物は良好な活性を示す。実施例Ｂ−４：ブドウの木におけるプラスモパラ・ヴィチコラ(Plasmopara viti cola)に対する活性４葉ないし５葉期のブドウ苗木を有効成分の水和剤により調製した水性噴霧混合物（有効成分０．０２％）で滴る時点まで噴霧しそして２４時間後、菌の胞子嚢懸濁液に感染させる。真菌の侵攻は感染から、期間中相対大気湿度９０ないし１００％および２０℃の温度に保持された６日間の後に評価される。表１および２の化合物は良好な活性を示す。実施例Ｂ−５：キュウリにおけるコレトトリカム・ラゲナリウム(Colletorichum lagenarium)に対する活性キュウリ植物を２週間生育させそして次に有効成分の水和剤により調製した噴霧混合物（濃度０．００２％）で噴霧する。２日後、植物を菌の胞子混合物（１．５×１０⁵胞子／ｍｌ）で感染させ、２３℃および高湿度で３６時間保温する。次に、保温を通常の湿度および約２２℃で継続する。現れた真菌の侵攻は感染後８日に評価される。表１および２の化合物は良好な活性を示す。実施例Ｂ−６：リンゴにおけるベンチュリア・インアエクアリス(Venturia inae qualis)に対する残留−保護活性１０〜２０ｃｍの高さの若木のリンゴ苗木に、有効成分の水和剤により調製した噴霧混合液（有効成分の０．０２％）で滴る時点まで噴霧し、そして２４時間後、植物を菌の分生子懸濁液で感染させる。植物を５日間、９０〜１００％の相対大気湿度で保温し、さらに１０日間、２０〜２４℃の温室中に置く。感染１２日後に、真菌の侵攻を評価する。表１および２の化合物は良好な活性を示す。実施例Ｂ−７：大麦におけるエリシフェ・グラミニス(Erysiphe graminis)に対する活性ａ）残留−保護活性約８ｃｍの高さの大麦植物に、有効成分の水和剤により調製した水性噴霧混合液（有効成分０．０２％）で滴る時点まで噴霧し、そして３ないし４時間後、菌の分生子をふりかける。感染された大麦植物を約２２℃の温室中におきそして１２日後に真菌の侵攻を評価する。表１および２の化合物は良好な活性を示す。ｂ）浸透活性有効成分の水和剤により調製した水性噴霧混合物（土壌容量に基づいて有効成分０．００２％）を約８ｃｍの高さの大麦植物の周囲に注ぐ。噴霧混合物が植物の地上部に触れないように注意する。４８時間後、植物に菌の分生子をふりかける。感染された植物を約２２℃の温室中におき、感染１２日後、真菌の侵攻を評価する。表１および２の化合物は良好な活性を示す。実施例Ｂ−８：リンゴ若木におけるポドスファエラ・ロイコトリカ(Podosphaera leucotricha)に対する活性残留−保護活性１５ｃｍの高さの若木のリンゴ苗木に、噴霧混合液（有効成分の０．０６％）を噴霧する。２４時間後、処理した植物を菌の分生子懸濁液で感染させ、そして相対大気湿度７０％および２０℃に制御された環境のキャビネットに置く。感染１２日後に、真菌の侵攻を評価する。表１および２の化合物は良好な活性を示す。生物学的実施例：Ｂ．殺ダニ活性、殺虫活性および殺線虫活性実施例Ｂ−９：テトラニクス・ウルチカエ(Tetranychus urticae)〔ダニ目〕に対する活性幼若豆植物にテトラニクス・ウルチカエの混合集団を生息させ、１日後、有効成分４００ｐｐｍを含む水性乳剤混合液を噴霧する。植物は続いて２５℃で６日間保温し、そして評価する。集団における減少率（活性％）は処理された植物上の死滅した卵、幼生および成虫の数と処理しなかった植物上の数とを比較することによって測定する。表１および２の化合物は良好な活性を示す。実施例Ｂ−１０：矮性豆(dwarf beans)におけるテトラニクス・シンナバリヌス( Tetranychus cinnabarinus)〔ダニ目〕に対する活性稀釈シリーズ２葉期の矮性豆にＯＰ−耐性種のテトラニクス・シンナバリヌス種の混合集団（卵、幼生／幼虫および成虫）を生息させる。感染２４時間後、農薬製品を、有効成分２００、１００および５０ｍｇ／ｌの施用割合で自動噴霧室内で植物に施用する。上記物質は製剤化され、水で稀釈されて当該濃度施用割合が得られる。施用２日および７日後この試験は −卵， −幼生／幼虫および −成虫の死滅率により評価される。有効成分５０ｍｇ／ｌと同様の低い稀釈における表１および２の化合物は７０％を超える死滅率を示す。実施例Ｂ−１１：ニラパルヴァタ・ルゲンス(Nilaparavata lugens)〔昆虫類〕に対する活性稲植物を有効成分４００ｐｐｍを含む水性乳剤噴霧混合物で処理する。噴霧付着物が乾燥した後、稲植物に第二および第三期のウンカ幼虫を生息させる。評価は２１日後行われる。個体群の減少率（活性％）は処理された植物の生き残ったウンカの数と未処理植物におけるものとを比較することにより決定される。表１および２の化合物は９０％以上の活性を示す。実施例Ｂ−１２：プルテラ・キロステラ(Plutella xylostella)芋虫〔昆虫類〕に対する活性幼若キャベツ植物を本発明の有効成分４００ｐｐｍを含む水性乳剤噴霧混合物で噴霧する。噴霧付着物が乾燥した後、キャベツ植物に第三期のプルテラ・キロステラの芋虫１０匹を生息させ、プラスチック容器内に入れる。評価は３日後行われる。個体群の減少率および摂食の損傷による減少率は（活性％）は処理された植物上で死んだ芋虫および摂食の損傷をうけた芋虫の数を未処理植物上のものと比較することにより決定される。表１および２の化合物は良好な活性を示す。実施例Ｂ−１３：ムスカ・ドメスティカ(Musca domestica)〔昆虫類〕に対する活性砂糖の塊を、一夜乾燥後砂糖中の試験物質の濃度が２５０ｐｐｍとなるような方法で試験物質の溶液で処理する。湿った脱脂綿球と一緒にこの処理した塊および１０匹のＯＰ−耐性種のムスカ・ドメスティカ成虫をアルミニウム皿に置き、そしてこれをガラスビーカーで覆って、２５℃で保温する。２４時間後、死滅率を測定する。表１および２の化合物は良好な活性を示す。Ｂ−１４：大豆におけるヘテロデラ・グリシンズ(Heterodera glycines)〔線虫類〕に対する活性砂質土壌を１ポット当たりおよそ６０００卵のダイズシストセンチュウ：ヘテロデラ・グリシンズ(Heterode ra glycines)の卵により、汚染させる（infested）。次いで試験物質を適当な濃度で混ぜ込む。次に処理されそして汚染された土壌で1cポット(180ccm)の中を満たしそして１ポットに付きに三個の大豆（cv.Maple Arrow）を播種する。各処理を三回繰り返す。ポットを温室中において約２７℃にて４ないし５週間の間保温する。その後植物をポットより注意深く取り出し、根を洗い、そしてシストの数を測定する。シスト形成の目視上の完全な減少から見られ得るように表１および２の化合物はヘテロデラ・グリシンズに対して良好な活性を示す。Detailed Description of the InventionPyrimidin-4-ylaminotylquinoline derivatives as pest control agents The invention relates in each case to the compounds of the formula I in free or salt form [In the formula, the substituent A is at the 6- or 7-position, R₁Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms Alkoxy group having 1, 2 or 3 halogen atoms, halo-having 1 carbon atom Represents an alkyl group having 4 to 4 or an alkylthio group having 1 to 4 carbon atoms; R₂And R_ThreeAre each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Halo-alkyl having 1 to 4 carbon atoms having 1 to 5 halogen atoms Group, alkoxy group having 1 to 2 carbon atoms-alkyl group having 1 to 4 carbon atoms Nitro-alkyl having 1 to 4 carbon atoms, cyano- having 1 to 4 carbon atoms An alkyl group of alkanoyl having 1 to 4 carbon atoms-having 1 to 4 carbon atoms Alkyl groups, C 1 -C 4 ar Coxycarbonyl-alkyl group having 1 to 4 carbon atoms, 1 to 2 carbon atoms Alkylthio-C1 -C4 alkyl, C1 -C2 Alkanesulfinyl-C1 -C4 alkyl, not C1 2 alkanesulfonyl-C 1 -C 4 alkyl group, C 2 To 4 alkenyl groups, halo-carbons having 1, 2 or 3 halogen atoms An alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, carbon Cycloalkyl group having 3 to 7 elementary atoms, alkoxy group having 1 to 4 carbon atoms , Halo-alkoxy groups having 1 to 4 carbon atoms, alkyl groups having 1 to 4 carbon atoms Ruthio group, halo-alkylthio group having 1 to 4 carbon atoms, 1 to 4 carbon atoms An alkylsulfinyl group having 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, Amino group, acylamino group having 1 to 4 carbon atoms, nitro group, cyano group, hydr Represents a roxyl group or a halogen atom; R_FourIs a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 Halo-halogenated alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom Isocyanate 2 alkoxy-alkyl group having 1 to 4 carbon atoms, nitro-number of carbon atoms 1 to 4 alkyl group, cyano-alkyl group having 1 to 4 carbon atoms, carbon atom A cycloalkyl group having 3 to 5 carbon atoms, a benzyl group, an alkyl group having 1 to 4 carbon atoms Anoyl group, benzoyl group; its phenyl group Is unsubstituted or a halogen atom, an alkyl group having 1 to 2 carbon atoms, With 1, 2 or 3 substituents selected from the group consisting of toro and cyano groups Represents a substituted benzoyl group; R_FiveAnd R₆Are, independently of one another, a hydrogen atom, an alkyl having 1 to 4 carbon atoms Groups having 1, 2 or 3 halogen atoms, halo-having 1 to 4 carbon atoms Alkyl group, alkoxy having 1 to 2 carbon atoms-alkenyl having 1 to 4 carbon atoms Kill group, nitro-alkyl group having 1 to 4 carbon atoms, cyano-group having 1 carbon atom Ishi 4 alkyl group, C 1 -C 4 alkoxycarbonyl-carbon atom Alkyl groups of the numbers 1 to 4; or unsubstituted or halogen atoms and charcoal Substitution of 1 or 2 selected from the group consisting of alkyl groups having 1 to 2 elementary atoms Represents a cycloalkyl group having 3 to 6 carbon atoms substituted by a group; R₇Is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, cyclop Ropyl group, an alkoxy group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms Represents an alkylthio group; X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs a hydrogen atom; substituted or unsubstituted, open having 12 or less carbon atoms Chains, saturated or unsaturated hydrocarbon groups; substituted or unsubstituted, up to 10 charcoals Cyclic, saturated or unsaturated hydrocarbon groups containing elementary atoms; if substituted Or an unsubstituted benzyl group; or a substituted or unsubstituted heterocyclic group; R₁₁Is a hydrogen atom; has 8 or less carbon atoms, and is unsubstituted or 1 5 halogen atoms, an alkoxy group having 1 to 2 carbon atoms, hydroxyl Group, nitro group, cyano group, alkanoyl group having 1 to 4 carbon atoms, halo-carbon Alkanoyl group having 1 to 4 atoms or alkoxy having 1 to 4 carbon atoms 10 open-chain, saturated or unsaturated hydrocarbon groups substituted by carbonyl groups; Cyclic, saturated or unsaturated hydrocarbon groups having the following carbon atoms; or carbocycles Is unsubstituted, a halogen atom, an alkyl group having 1 to 2 carbon atoms, Benzyl mono- or di-substituted by a methyl, nitro or cyano group A group; or an unsubstituted or C 1 -C 2 alkyl group, halogen Same atom from the series consisting of a hydrogen atom, a halomethyl group, a nitro group or a cyano group. Or represents a heterocyclic group which is mono- or tri-substituted by different substituents; R₁₂Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; or R₁₁And R₁₂Are the unsubstituted or substituted, together with the nitrogen atoms to which they are attached. Or a halogen atom, an alkyl group having 1 to 2 carbon atoms, a halomethyl group or Mono- or tri-substituted by the same or different substituents from the series consisting of nitro groups Represents a heterocycle. ] New represented by Pestically active compounds, or tautomers thereof, where appropriate. The present invention also provides a method for producing these compounds; Agrochemical composition containing at least one compound, and effective in agriculture or horticulture Ingredients or pest control agents, in particular their use as microbicides. Compound I and, if appropriate, their tautomers exist in the form of salts. Conversion Since Compound I has at least one basic center, they form, for example, acid addition salts. it can. These salts are, for example, mineral acids such as sulfuric acid, phosphoric acid or hydrohalic acid. By; organic carboxylic acids such as acetic acid, oxalic acid, malonic acid, succinic acid, male With in-, fumaric or phthalic acids; hydroxycarboxylic acids such as as By corbic acid, lactic acid, malic acid, tartaric acid or citric acid; or benzoin By an acid; or an organic sulfonic acid such as methanesulfonic acid or p-tolu Formed by enesulfonic acid. Furthermore, compounds of formula I having at least one acidic group are capable of forming salts with bases. You. Suitable salts with bases are, for example, alkali metal salts or alkaline earth metal salts, for example Sodium, potassium or magnesium salts, or salts with ammonia Or a salt with an organic amine, for example, morpholine, piperidine, pyrrolidine, Mono-, di- or tri-lower alkyl amines such as ethyl-, di- Ethyl-, triethyl- or dimethylpropylamine, or mono-, di- -Or trihydroxy-lower alkylamine, such as mono-, di- or It is triethanolamine. In addition, the corresponding inner salts also form at the possible sites. Can be achieved. Preferred salts within the scope of the present invention are agrochemically advantageous salts. Unless otherwise defined, the general terms used above and below are set forth below. Represents the meaning. An alkyl group is straight or branched depending on the number of carbon atoms, For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, Secondary butyl group, isobutyl group, tertiary butyl group, secondary amyl group, tertiary amyl group, 1 A hexyl group or a 3-hexyl group. An alkenyl group is to be understood as meaning a straight-chain or branched alkenyl group. Such as allyl, methallyl, 1-methylvinyl or bute-2- Any-1-yl group, an alkenyl group having a chain length of 3 to 4 carbon atoms. Is preferred. The alkynyl group can also be straight or branched depending on the number of carbon atoms. , For example, a propargyl group, a but-1-yn-1-yl group or a but-1-yn group. It may be a -3-yl group. A propargyl group is preferred. The unsubstituted hydrocarbon group may be an alkenyl group or an alkynyl group having multiple bonds of 3 or less. Or an alkenynyl group, for example Butadienyl group, hexatrienyl group, and 2-penten-4-ynyl group. Halogen atom or halo group means fluorine atom, chlorine atom, bromine atom or iodine atom. An atom, preferably a fluorine atom, a chlorine atom or a bromine atom. Haloalkyl groups can have the same or different halogen atoms and are mentioned Examples are: fluoromethyl group, difluoromethyl group, difluorochloromethyl group, Trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group Group, 2,2,2-trifluoroethyl group, 2-fluoroethyl group, 2-chloroethyl group Cyl group, 2,2,2-trichloroethyl group, 3,3,3-trifluoropropyl Group. Alkoxy group, for example, methoxy group, ethoxy group, propyloxy group, i-type Ropyloxy group, n-butyloxy group, iso-butyloxy group, sec-butyloxy group And tert-butyloxy groups; preferably methoxy and ethoxy groups is there. A haloalkoxy group is, for example, a difluoromethoxy group or a trifluoromethoxy group. 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroeth Xy group, 2-fluoroethoxy group, 2-chloroethoxy group and 2,2-diflu It is an oroethoxy group. The cycloalkyl group is a cyclopropyl group or a cyclobutyl group depending on the size of the ring. , Cyclopentyl group, cyclohexyl It is a xyl group or a cycloheptyl group. The cyclic unsaturated hydrocarbon group is an aromatic group such as phenyl group, naphthyl group, or Is a non-aromatic group such as cyclopentenyl group, cyclohexenyl group, cycloheptenyl group. Nyl and cyclooctadienyl groups, or partially aromatic groups such as It may be a trahydronaphthyl group and an indanyl group. The alkanoyl group is in each case a straight-chain or It is a branched one. Possible examples are formyl, acetyl, propio. A nyl group, a butyryl group, a pivaloyl group or an octanoyl group. Alkoxyalkyl, alkylthioalkyl, alkanesulfinylalkyl , Alkanesulfonylalkyl, nitroalkyl, cyanoalkyl and cyano Such as alkanesulfonyl; alkoxy-, alkylthio-, alkanesulf An innyl-, alkanesulfonyl-, nitro- or cyano-substituted carbon-containing group and In compounds, these groups and in the unsubstituted basic structure on which the compound is based One of the hydrogen atoms is alkoxy, alkylthio, alkanesulfinyl, alka Substituted with a sulfonyl, nitro or cyano group. Heterocyclic groups are 5- or 6-membered, heterocyclic, with heteroatoms N, O and / or S. It should be understood as aromatic and non-aromatic rings. Furthermore, the unsubstituted or substituted Was done The benzo group can be fused like a heterocyclic group attached to the remainder. Examples of heterocyclic groups are , Pyridyl group, pyrimidinyl group, imidazolyl group, thiazolyl group, 1,3,4- Thiadiazolyl group, triazolyl group, thienyl group, furanyl group, pyrrolyl group, molybdenum A ruforinyl group, an oxazolyl group and the corresponding partially or fully hydrogenated It is a ring. Examples of the hetero group having a condensed benzo group include quinolyl group, isoquinolyl group, Nzoxazolyl group, quinoxalinyl group, benzothiazolyl group, benzimidazolyl group A group, an indolyl group and an indolinyl group. All enumerations set forth above are for purposes of example and not limitation. Preferred compounds within the scope of the invention are shown below: (1) where R_TenHas up to 8 carbon atoms and is unsubstituted or 1 5 halogen atoms, an alkoxy group having 1 to 2 carbon atoms, hydroxyl Group, nitro group, cyano group, alkanoyl group having 1 to 4 carbon atoms, halo-carbon Alkanoyl group having 1 to 4 atoms or alkoxy having 1 to 4 carbon atoms 10 open-chain, saturated or unsaturated hydrocarbon groups substituted by carbonyl groups; Cyclic, saturated or unsaturated hydrocarbon groups having the following carbon atoms; or carbocycles Is unsubstituted, a halogen atom, an alkyl group having 1 to 2 carbon atoms, Benzyl mono- or di-substituted by a methyl, nitro or cyano group Group; or unsubstituted Or a halogen atom, an alkyl group having 1 to 2 carbon atoms, a halomethyl group, a diamine Substituted by the same or different substituents from the series consisting of toro or cyano groups To a trisubstituted heterocyclic group or a 5- to 7-membered lactone ring of formula I A compound represented by the formula: In formula (2), R_TenIs a hydrogen atom, has not more than 12 carbon atoms and is unsubstituted. Or with a tri (C1-4alkyl) silyl group or An open-chain, saturated or unsaturated hydrocarbon group substituted by a poxy group; or Group: -CH (U) (CH₂)_mCO-W [Wherein U is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cyano group or a carbon atom] Represents an alkoxycarbonyl group having 1 to 6 elementary atoms; W is an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl having 3 to 6 carbon atoms Coxy group or group: -N (T₁) T₂Represents; m represents 0, 1 or 2; and T₁And T₂Are, independently of each other, a hydrogen atom; unsubstituted or 1 to 3 Halogen atoms, alkoxy groups having 1 or 2 carbon atoms, hydroxyl groups, Toro group, cyano group, alkanoyl group having 1 to 4 carbon atoms, halo-number of carbon atoms An alkanoyl group having 1 to 4 or an alkoxycarbo having 1 to 4 carbon atoms An alkyl group having 1 to 6 carbon atoms substituted with an nyl group or Not substituted or substituted with 1 to 3 halogen atoms having 1 carbon atom 6 alkenyl groups, unsubstituted or substituted with 1 to 3 halogen atoms An alkynyl group having 1 to 6 carbon atoms; having a carbon number of 10 or less, Cyclic, saturated or unsaturated hydrocarbon radicals; or carbocycles unsubstituted or Rogen atom, alkyl group having 1 to 2 carbon atoms, halomethyl group, nitro group Or a benzyl group mono- or di-substituted by a cyano group; or unsubstituted Or an alkyl group having 1 to 2 carbon atoms, a halogen atom, a halomethyl group, a diene Substituted by the same or different substituents from the series consisting of toro or cyano groups Or represents a tri-substituted heterocyclic group; or T₁And T₂Is a ring atom together with the nitrogen atom to which they are attached , 5 and 7-membered heterocycles which may carry S, S and / or N Wherein the additional nitrogen is unsubstituted or is an alkyl group having 1 to 4 carbon atoms. , A phenyl group, an alkanoyl group having 1 to 4 carbon atoms, a benzoyl group or a phenyl group. Is substituted with a benzyl group and the carbon atoms of the heterocycle are unsubstituted Alternatively, a halogen atom, an alkyl group having 1 to 2 carbon atoms, a halomethyl group or Is mono- or tri-substituted by the same or different substituents from the series consisting of nitro groups Have been. ) Is formed. A compound of formula I (3) where R_TenIs a hydrogen atom, has up to 6 carbon atoms and is unsubstituted Or by a tri (C 1 -C 4 alkyl) silyl group or epoxide An open-chain, saturated or unsaturated hydrocarbon group substituted by a Si group; or a group:- CH₂-CO-W [In the formula, W is an alkoxy group having 1 to 6 carbon atoms, and is an alkoxy group having 3 to 6 carbon atoms. Chalkoxy group or group: -N (T₁) T₂Represents; T₁And T₂Are independently of each other a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, Halo-alkyl groups having 1 to 6 carbon atoms having 1 to 3 halogen atoms , A cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, 1 to 3 halo Represents a halo-phenyl group, a pyridyl group or a naphthyl group having a gen atom; or T₁And T₂Are piperidine, piperazine together with the nitrogen atom to which they are attached Or morpholine or 2,6-dimethylmorpholine. ] Represented by Formula I Compound. In formula (4), R₁Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R₂Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 Halo-halogenated alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom An alkoxy group having 2 carbon atoms and an alkyl group having 1 to 4 carbon atoms, Represents a chloropropyl group, an ethynyl group or a halogen atom; R_ThreeRepresents a fluorine atom or a chlorine atom; R_FourRepresents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R_FiveRepresents an alkyl group having 1 to 4 carbon atoms; R₆Represents a hydrogen atom; R₇Represents a hydrogen atom or a halogen atom; X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 halogen atoms A halo-alkyl group having 1 to 4 carbon atoms, having 1 to 2 carbon atoms. Lucoxy-alkyl group having 1 to 4 carbon atoms, hydroxy-not having 1 carbon atom 4 alkyl group, nitro-alkyl group having 1 to 4 carbon atoms, cyano-carbon An alkyl group having 1 to 4 atoms, an alkanoyl-carbon atom having 1 to 4 carbon atoms An alkyl group having 1 to 4 carbon atoms, an alkoxycarbonyl having 1 to 4 carbon atoms An alkyl group having 1 to 4 carbon atoms; unsubstituted or halogen atom Isocyanate-substituted alkenyl groups having 2 to 4 carbon atoms; 2 to 4 carbon atoms No alkynyl groups, cycloalkyl groups having 3 to 7 carbon atoms, 4 carbon atoms 8 cycloalkenyl group, benzyl group; unsubstituted or halogen atom, 1 to 2 positions of an alkyl group having 1 to 2 carbon atoms, a nitro group or a cyano group Replaced Phenyl group; or pyridine group, pyrimidine group or triazine group (these compounds The elementary rings are unsubstituted or each has a halogen atom or C 1 -C 2 Same bit from a system consisting of alkyl, trifluoromethyl or cyano groups Or mono- to tri-substituted by different groups. ) Or a 5-membered lactone ring Do; R₁₁Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 Halo-halogenated alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom Alkoxy having 1 to 2 carbon atoms, alkyl group having 1 to 4 carbon atoms, hydroxy-carbon atom Alkyl group having 1 to 4 carbon atoms, nitro-alkyl group having 1 to 4 carbon atoms, Ano-C1 to C4 alkyl group, C1 to C4 alkanoy Ru-C1-4 alkyl group, C1-C4 alkoxy group Rubonyl-alkyl group having 1 to 4 carbon atoms; unsubstituted or halogen An alkenyl group having 2 to 4 carbon atoms, which is mono- or trisubstituted with atoms; the number of carbon atoms 2 to 4 alkynyl group, C 3 to C 7 cycloalkyl group, carbon atom A cycloalkenyl group having a child number of 4 to 8, a benzyl group; unsubstituted or halo A gen atom, an alkyl group having 1 to 2 carbon atoms, a nitro group or a cyano group Or represents a disubstituted phenyl group; R₁₂Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; or R₁₁And R₁₂Is a pyrrolidine group together with the nitrogen atom to which they are attached, Piperidine group, piperazine group, morpholine group or 2,6-dimethylmorpholine A compound of formula I which represents a group. Among the compounds to be mentioned on the basis of (4), the preferred ones are Is shown in: In the equation (4.1), X is SR_TenIs a compound. In the formula (4.2), X is OR_TenIs a compound. (5) where R₁Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R₂Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 ha Halo-halogenated alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom Alkoxy group of Ishi-alkyl group having 1 to 4 carbon atoms, cyclopropyl group Represents an ethynyl group or a halogen atom; R_ThreeRepresents a chlorine atom; R_FourRepresents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R_FiveRepresents an alkyl group having 1 to 4 carbon atoms; R₆Represents a hydrogen atom; R₇Represents a hydrogen atom; X is OR_TenOr SR_TenRepresents; R_TenIs based on: -CH₂Represents -CO-W; W is an alkoxy group having 1 to 6 carbon atoms, the number of carbon atoms A cycloalkoxy group of 3 to 6, or a group -N (T₁) T₂Represents; T₁And T₂Are, independently of each other, a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Group having 1 to 3 halogen atoms, halo-alkenyl having 1 to 6 carbon atoms Group, cycloalkyl group having 3 to 6 carbon atoms, phenyl group, 1 to 3 Represents or is a halophenyl group, pyridyl group, or naphthyl group having a halogen atom Iha T₁And T₂Is a piperidine group together with the nitrogen atom to which they are attached, In formula I, which represents a perazine group, a morpholine group or a 2,6-dimethylmorpholine group. The compound represented. (6) The following equation I. 1 [Wherein, R₂Represents a hydrogen atom, a methyl group or an ethyl group; R_ThreeRepresents a fluorine atom or a chlorine atom; R_FiveRepresents a methyl group or an ethyl group; R₇Represents a hydrogen atom or a fluorine atom; X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs an alkyl group having 1 to 4 carbon atoms, difluoromethyl group, trifluoro Methyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, vinyl Group, allyl group, 2-propynyl group, cyclopentyl group, cyclohexyl group, cyclo Rohexenyl group, cyanomethyl group or C1-C4 alkoxycarboxyl Represents a carbonylmethyl group; R₁₁Is a hydrogen atom, alkyl group having 1 to 4 carbon atoms, cyclohexyl group, cyclo Represents a propyl group or a phenyl group; R₁₂Represents a hydrogen atom; or R₁₁And R₁₂Together with the nitrogen atom to which they are attached, the piperidine group , Morpholine group or 2,6-dimethylmorpholine group. Compound represented by) Stuff. (7) Formula I. 2 (Where R₂Represents a hydrogen atom, a methyl group or an ethyl group; R_ThreeRepresents a fluorine atom or a chlorine atom; R_FiveRepresents a methyl group or an ethyl group; R₇Represents a hydrogen atom or a fluorine atom; X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs an alkyl group having 1 to 4 carbon atoms, difluoromethyl group, trifluoro Methyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, vinyl Group, allyl group, 2-propynyl group, cyclopentyl group, cyclohexyl group, cyclo Rohexenyl group, cyanomethyl group or C1-C4 alkoxycarboxyl Represents a carbonylmethyl group; R₁₁Is a hydrogen atom, alkyl group having 1 to 4 carbon atoms, cyclohexyl group, cyclo Represents a propyl group or a phenyl group; R₁₂Represents a hydrogen atom; or R₁₁And R₁₂Together with the nitrogen atom to which they are attached, the piperidine group , Morpholine group or 2,6-dimethylmorpholine group. Compound represented by) Stuff. (8) Formula I. 1a (Where R_TenIs unsubstituted or mono- or trisubstituted by halogen atoms Alky having 1 to 5 carbon atoms Group, or carbon which is unsubstituted or mono- or tri-substituted by halogen atoms It represents an alkenyl group having 2 to 5 elementary atoms. ) The compound represented by. A compound of the formula I, in each case in free or salt form, and If so, the tautomer can be prepared as shown below: (A) a) X is SR_TenIn order to prepare a compound of formula I: Formula II Where the substituent A is in the 6 or 7-position and R₁Through R₇Is defined by Formula I It is the same as the one justified. ) And a compound of formula III R_Ten-Z (III) (Where R_TenHas the same meaning as defined in formula I, and Z is easily eliminated Represents a nucleofugic radical. ) And a compound represented by Is preferably reacted in the presence of a base, but particularly preferably first of formula II React the compound with a base, then Reacting a compound of formula III; or b) X is OR_TenOr N (R₁₁) R₁₂To prepare a compound of formula I In conclusion: X is SR_TenA compound of formula I MX (IV) (In the formula, M is a hydrogen atom, Li⁺, Na⁺, K⁺, 1/2 Mg²⁺Or quaternary Ammoniu Represents Muion; X is OR_TenOr N (R₁₁) R₁₂Represents and R_Ten, R₁₁And R₁₂Is defined by Formula I Has the same meaning as defined. ) In the presence of a base, if appropriate Or react with c) R_FourIs the same as defined in Formula I, but is represented by Formula I where it is other than a hydrogen atom. To produce the compound: R_FourIs a hydrogen atom and a compound of formula I and formula V R_Four‘−Z’ (V) (Where R_Four′ Is R in formula I_FourIs the same as that defined for Outside and Z'represents a nucleofusidic group that is easily removed. ) The compound is reacted, preferably in the presence of a base. (B) Formula VII Where the substituent A is in the 6 or 7-position and R₁Through R₇Is defined by Formula I It is the same as the one justified. ), Phosphorus oxychloride, and thioni chloride. Or sulphuryl chloride to give a compound of formula VIII To obtain a compound of formula IV ' M-X '(IV') (In the formula, M is a hydrogen atom, Li⁺, Na⁺, K⁺, 1/2 Mg²⁺Or quaternary Ammoniu Represents Muion; X'is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents and R_Ten, R₁₁And R₁₂ Represents the same meaning as defined in formula I. ) And a compound represented by React in the presence of groups. (C) Formula IX Where the substituent A is in the 6 or 7-position and R₁Through R₇Is defined by Formula I It is the same as the one justified. ) And the oxidant are reacted with each other. Examples of suitable oxidizing agents are iron (III) salts, SeO.₂, MnO₂, H₂O₂, Br₂, Cl₂ , I₂, SO_Three, H₂SO_Four, HNO_Three, N-bromosuccinimide, 2,3-dic In the presence of loro-5,6-dicyano-1,4-benzoquinone or a dehydrogenation catalyst O₂It is. (D) Formula IX ' Where the substituent A is in the 6 or 7-position and R₁Through R₇And X is Is the same as defined in Formula I and Z is a readily removable nucleofuhe It is a Zick group. ) HZ is eliminated from the compound represented by Let it. The reactions described above and below can be carried out in a manner known per se, for example, with a suitable solvent. Or in the absence or convenient presence of diluents or mixtures thereof. The above-mentioned method is, for example, about -80 ° C to the boiling point of the reaction medium, preferably about Within a temperature range of approximately -20 ° C to approximately + 150 ° C, with proper cooling , At room temperature or with heating; in a sealed container, if necessary, under pressure In an inert gas atmosphere and / or under anhydrous conditions. Typical reaction Conditions can be found in the examples. Examples of nucleofusidic groups Z or Z'are: fluorine atom, chlorine atom, bromine source. Child, iodine atom, charcoal such as methylthio group, ethylthio group or propylthio group Alkylthio group having 1 to 8 elementary atoms; not having 1 carbon atom such as acetoxy group 8 alkanoyloxy group; methanesulfonyloxy group, ethanesulfonyloxy group (Halo-) carbon source such as xy group or trifluoromethanesulfonyloxy group An alkanesulfonyloxy group having 1 to 8 children; or benzenesulfonyloxy A substituted or unsubstituted group such as a Si group or a p-toluenesulfonyloxy group A phenylsulfonyloxy group, and also a hydroxyl group. Suitable bases are, for example, alkali metal or alkaline earth metal hydroxides, hydrogen. Compound, amide, alkanolate, carbonate, dialkylamide or alkylsilyl Lamide or alkylamine, alkylenediamine, free or N-al Killed saturated or unsaturated cycloalkylamines, basic heterocyclic compounds, water Ammonium oxide and carbocyclic amines. Examples that may be mentioned are sodium hydroxide. Sodium, sodium hydride, sodium amide, sodium methanolate, sodium carbonate Thorium, potassium tertiary butanolate, potassium carbonate, lithium diisopro Pyramide, potassium bis (trimethylsilyl) amide, calcium hydride, Liethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl Xyl-N, N-dimethylamine, N, N-diethylaniline, pyridine, 4- (N, N-dimethylamino) pyridine, N-methylmorpholine, benzyl trime Tylammonium hydroxide and 1,5-diazabicyclo [5.4.0] It is undecese-5-ene (DBU). The reactants are intact with each other, i.e. without the addition of solvents or diluents, e.g. It can be reacted in the melt. However, in many cases an inert solvent or It is advantageous to add a diluent or a mixture thereof. So that can be mentioned Examples of suitable solvents or diluents are aromatic, aliphatic and cycloaliphatic hydrocarbons and halocarbons. Hydrogen fluoride, such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene Benzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloro Methane, trichloromethane, tetrachloromethane, dichloroethane or trike Loroethane; ethers such as diethyl ether, tert-butyl methyl ether , Tetrahydrofuran or dioxane; ketones such as acetone or methyl Ruethyl ketone; alcohols such as methanol, ethanol, propanol, Butanol, ethylene glycol or glycerol; esters such as acetic acid Tyl or butyl acetate; amides such as N, N-dimethylform Amide, N, N-dimethylacetamide, N-methylpyrrolidone or hexame Tyrphosphate triamide; Nitriles such as acetonitrile; and sulfoxy A dimethyl sulfoxide, for example. Bases used in excess, such as Trier Cylamine, pyridine, N-methylmorpholine or N, N-diethylaniline May also act as a solvent or diluent. The reaction is about 0 ° C to about + 180 ° C, preferably about + 20 ° C to about + 130 ° C. Of the solvent used, often between the reflux temperatures of the solvents used. You. Alternatively, the reaction is carried out in an aqueous solvent in an organic solvent such as methylene chloride or toluene. Potassium solution, such as sodium hydroxide, and a phase transfer catalyst, such as hydrogen sulfate It can be carried out using phase transfer catalysis in the presence of trabutylammonium. Compounds obtainable according to the invention or by other routes or, where appropriate, The tautomers of the compounds of the above are known per se and can be prepared by conventional methods using other substituents. By substituting one or more substituents of compound I starting with Can be converted to compound I. For example, -Substituents containing no halogen atoms, or non-halogenated aromatics or The aromatic ring part-structure is halogenated to give a halogen-containing substituent, or A partial-structure of a rogenated aromatic or heteroaromatic ring is obtained. It is. -Halogen substituents such as cyano, alkylthio or alkoxy substituents It can be exchanged for other substituents. -Alkanoyl, benzoyl or sulfonyl substituents are easily exchanged Can be replaced with hydrogen. -N-hydrogen is N-alkyl, N-benzyl, N-aryl, N-heteroary. Group, N-alkanoyl, N-benzoyl or N-sulfonyl group is there. -Sulfides are oxidized to give sulfoxides and sulfones. The carbonyl group is sulphated to give the thiocarbonyl group. The invention relates to the possible pure isomers and mixtures of all isomers. The invention also relates to the novel starting materials used for the preparation of the compounds of formula I It also relates to qualities and intermediates, their use and their method of manufacture. The compounds represented by the formulas II, VII and IX are known compounds represented by the following chemical reaction formulas. Can be manufactured by a method. In this chemical formula, A, R_Ten, Z, M and X have the same meanings as defined above. You. The following are suitable as oxidizing agents: iron (III) salts, SeO.₂, Mn O₂, H₂O₂, Br₂, Cl₂ , I₂, SO_Three, H₂SO_Four, HNO_Three, N-bromosuccinimide, benzoquinone For example, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ ) Or O in the presence of a dehydrogenation catalyst₂It is. Examples of thionating agents Is phosphorus pentasulfide or 2,4-bis (4-methoxyphenyl) -1,3-dithia -2,4-diphosphetane-2,4-disulfide ["Lawesson's reagent (Lawes son's reagent) ”]. The preparation of the compounds of the formulas IX, IX ', XI and XII is described, for example, in Swiss patent application No. 509 / 93-0 (filing date: February 18, 1993), No. 617 / 93-3 (filing date: March 1993) 2) and No. 1788 / 93-2 (filing date: June 16, 1993). Compounds of formula III, IV, V and VI are known or known Can be manufactured more. Amino-substituted pyrimidines at the 4-position are described, for example, in WO 92/08704. Already disclosed in the application. The compounds I of the present invention are characterized by these known compounds. Structurally different from compound; furthermore, the compounds of the formula I according to the invention have an unexpectedly strong biocidal activity. It has a phyto-, insecticidal, nematicidal and acaricidal activity. Plant protection directly in pests By acting and also by activating and stimulating the plant defense system (immunity) Occurs. The compounds of the formula I can be used in the agricultural sector and in related fields in plants. Effective composition for controlling pests Can be used as a minute. The active ingredient according to the invention is potent at low concentrations. By activity and they are well tolerated by plants and the environment Characterized by the fact that it is kind to. They have very advantageous therapeutic properties, Has anti-static and permeation properties and is used for the protection of a large number of cultivated plants it can. Using the active ingredient of formula I, plants in various crops of beneficial plants and Controls pests found in plant parts (fruits, flowers, leaves, stems, tubers, roots), and Can be destroyed, and even the parts of the plant that were produced in later stages of growth For example, it remains free from damage by phytopathogenic microorganisms. The compounds of formula I are further efficacious against fungal infections as well as phytopathogenic fungi of soil origin For the purpose of protection, plant propagation material, especially seeds (fruits, tubers, kernels) and plant seedlings Also as seed dressing agents for the treatment of (eg rice) Can be used. The compounds of formula I are effective, for example, against phytopathogenic fungi belonging to the following fungi: incomplete All fungi (e.g., Botrytis), Pyricularia (pyricularia), Helminthosporium, Fuzarium, Genus Septoria, Cercospora and Arnaaria (A lternaria)] and; Basidiomycetes [eg Rhizoctonia, hemi The genus Hemileia and the genus Puccinia )]. In addition they are cystic fungi [eg Venturia Binisiphe, Podosphaera, Moniniline Genus (Monilinia), genus Uncinula] and oomycetes [eg phytoft Phytophthora, Peronospora, Pythium pla It is effective against fungi of the genus Plasmopara. Furthermore, the compounds I according to the invention are suitable for agricultural crop plants and ornamental plants, in particular For the protection of stored products and materials in the forest of cotton, vegetable and fruit plants Acarina and Insect and Nematode Harm in the Home and Sanitation Division To control organisms and pests of animals such as livestock and livestock Various active ingredients for They are active against different stages of development. This Their activity is to kill pests immediately or only for a few hours, for example during the molt period. From later killing, or from significantly reduced spawning and / or hatching rates It becomes clear. The order Acarina includes, for example, Boophilus spp. C. species (Tetranychus spp.), And nematodes include, for example, Heterodera glycins (Het erodera glysines), and insects include, for example, Nilabarvata rugens (Ni laparvata lugens), Plutella xylostella and Musca -Includes domestica (Musca domestica). Target crops for crop protection applications within the scope of the present invention Objects are, for example, the following plant types: cereals (wheat, barley, rye, oats, Rice, corn, sorghum and related species); beet (sugar and forage beet) ); Pear fruit, drupe and soft fruit (apple, pear, plum, peach, almond, cherry) Dragonflies, strawberries, raspberries and blackberries); legumes (broad beans, ren) Beans, peas, soybeans; oil plants (rape, mustard, poppies, ollies) Bu, sunflower, coconut, castor oil plant, cocoa beans, peanuts); Cucurbitaceae plant Objects (pumpkin, cucumber, melon); fiber plant (cotton, flax, cannabis, jute); orange genus Plants (orange, lemon, grapefruit, mandarin); Vegetables (spinach) C, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, Capsicum); Lauraceae (Avocado, Cinnamon, Camphor); and Tobacco, Na Ts, coffee, sugar cane, tea, pepper and vines, hops, eggplants , Plants of other species such as, Musaceae, natural rubber plants as well as ornamental plants. The active ingredients of the formula I are usually applied in the form of combinations and the land to be treated. Alternatively, it may be applied to the plants simultaneously or subsequently with another active ingredient. other The active ingredients of, for example, fertilizers, trace element suppliers or other formulations that affect plant growth It may be. Other substances that can be used are selective herbicides as well as insecticides and fungicides ( fungicides), bactericides, nematicides, molluscicides Or a mixture of several of these formulations, where appropriate in the pharmaceutical industry Can also be used with other carriers, surfactants or application-enhancing aids used in it can. Suitable carriers and auxiliaries are solid or liquid and are convenient in the pharmaceutical industry. Substances used, eg natural or regenerated mineral substances, solvents, dispersants, wettable powders, sticks Adhesives, thickeners, binders or fertilizers. Active ingredients of formula I or pesticides containing at least one of these active ingredients The preferred method of application of the composition is foliar application (foliar application). Number of applications and The rate of application depends on the risk of attack by the pathogen in question. Instead of formula I The active ingredient may also be impregnated into the plant land with a liquid composition or in solid form, For example, by mixing the substance in the soil in the form of granules (soil application), through the root system It is also possible to reach plants from soil (penetration). Paddy rice [Paddy rice (paddy rice)], such granules should be weighed into the flooded rice field. Is possible. However, the compound of formula I is also a liquid formulation containing the active ingredient. Impregnate kernels or tubers or coat them with a solid formulation. It is applied to the seed grain (coating) depending on whether it is winged or not. The compounds of formula I may be used in their neat form or, preferably, with the auxiliaries customary in the pharmaceutical industry. Used with agents. For this purpose, they are, for example, emulsion stock solutions, coatable coatings. The most Directly sprayable or dilutable solutions, diluted emulsions, wettable powders, water solutions, powders, granules And, for example, according to known methods shown in encapsulating agents with polymeric substances. Processed well. Application methods such as spraying, atomizing, dusting, watering, brushing or And the nature of the composition is chosen to suit the intended purpose and environment of use. You. Convenient application rate is usually 5g of active ingredient (A.I.) per hectare (ha) 2 kg, preferably 10 g to 1 kg A.I./ha, and particularly preferably 20 g to 600 g A.I./ha. Seeds when used as seed dressing Application rates of 10 mg to 1 g of active ingredient per kg of offspring are conveniently used. Formulation, ie containing the active ingredient of formula I and, if desired, solid or liquid auxiliaries The compositions, formulations or combinations are prepared in a known manner, for example by extending the active ingredient with a bulking agent, for example: Solvents (mixtures), solid support materials and, if appropriate, surface-active compounds (surfactant It is produced by intimately mixing and / or grinding with an agent). The following can be used as solvents: aromatic hydrocarbons, preferably carbon. Portions of 8 to 12 atoms, eg xylene mixtures or substituted naphthalene , Phthalates such as dibutyl phthalate or dioctyl phthalate Aliphatic hydrocarbons such as cyclohexane or paraffin; alcohols and Recalls and their ethers and esters, eg ethanol Ethylene glycol, ethylene glycol monomethyl ether or ethylene Lenglycol monoethyl ether; ketones such as cyclohexanone; strong polarity Solvent such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethy Ruformamide; and epoxidized or non-epoxidized vegetable oils, such as Poxylated coconut oil or soybean oil; and water. For example, solid carriers used in powders and dispersible powders are typically calcite, talc Natural minerals such as, kaolin, montmorillonite or attapulgite . Add highly dispersed silicic acid or highly dispersed absorbent polymer to improve physical properties. Both are possible. Suitable granulated adsorptive carriers are of the porous type, such as pumice and crushed. Broken brick, sepiolite or bentonite, or non-absorbent carrier For example, calcite or sand-like substances. Even more granulated minerals And organic substances such as dolomite or powdered plant debris, among others, may be used . Due to the nature of the compound of Formula I formulated, suitable surface-active compounds are suitable as good milk. Nonionic, cationic and / or anionic with solubilizing, dispersing and hydrating properties It is a surfactant. Understand that surfactant also means a mixture of surfactants Should. Suitable anionic surfactants are so-called water-soluble soaps or water-soluble synthetic surfactants It is a sex compound. Examples of nonionic surfactants to mention are nonylphenol polyethoxy ethers. Tanol, castor oil polyglycol ether, polypropylene / polyethylene Oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol Recall and octylphenoxypolyethoxyethanol. In addition, Fatty acid esters of rioxyethylene sorbitan, eg polyoxyethylene sol Bitan trioleate is also suitable. Cationic surfactants mainly consist of at least one carbon atom as N-substituent. Alkyl groups of the numbers 8 to 22 and other substituents which are unsubstituted or halogenated lower alkyl groups. A quaternary ammonium group containing an alkyl group, a benzyl group, or a lower hydroxyalkyl group. Is a sodium salt. Surfactants commonly used in the pharmaceutical industry are known to those skilled in the art, and Or in the relevant specialized literature. Agrochemical formulations generally contain 0.1 to 99% by weight of active ingredient of the formula I, in particular 0.1%. 95% by weight, solid or liquid auxiliaries 99.9 to 1% by weight, in particular 99. 8 to 5% by weight, and 0 to 25% by weight of surfactant, especially 0.1 to 2 Contains 5% by weight. Concentrated compositions are often preferred as commercial products, but end consumers usually The composition will be used. The composition also contains stabilizers, defoamers, viscosity modifiers, binding agents to achieve special effects. Agent, sticker and fertilizer or Other active ingredients may also be included. The following examples illustrate the present invention without limiting its scope. explain. Temperature is expressed in degrees Celsius. The following abbreviations are used: Ac = acetyl; E t = ethyl; i-Pr = isopropyl; Me = methyl; Ph = phenyl; Pr = Bu = n-butyl; m. p. = Melting point; ds = diastereomer; reg = positional isomer. "NMR" means "nuclear magnetic resonance spectrum"; "MS ] = Mass spectrum. Unless different units are used to indicate the appropriate concentration "%" Means "% by weight".Examples for the preparation of compounds according to the invention Example H-1a: 7- [1- (5-chloro-6-ethylpyridimine-4-ylami No) ethyl] -3,4-dihydro-2-methylthioquinoline 0.9 g and 2, 3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) 0.86 g Is introduced into 20 ml of anhydrous dioxane in a sulfonation flask at room temperature and the mixture Is stirred at 85-90 ° C for approximately 6 hours. After cooling, the mixture is diluted with ethyl acetate 100 ml and 30 ml of water, separate the organic phase and then the aqueous phase twice with ethyl acetate. Extract. The organic phase is dried with sodium sulphate and the solvent is distilled off under reduced pressure on a water pump. Column chromatography on silica gel (eluent : N-hexane / tetrahydrofuran 3: 1) You. 7- [1- (5-chloro-6-ethylpyridimin-4-ylamino) ethyl ] 0.6 g of 2-methylthioquinoline in the form of white powder (mp 82-84 ° C) Can be obtained in the form A procedure similar to that described in Example H-1a can be prepared or one of the above procedures is performed. Other compounds that can be prepared for use are listed in the table below. Formulation Examples of Active Ingredients of Formula I Examples F-1.1 to F-1.3: Emulsion stock solution Emulsions of any desired concentration are obtained by diluting this stock solution with water.Example F-2: Emulsion stock solution Emulsions of any desired concentration are obtained by diluting this stock solution with water.Examples F-3.1 to F-3.4: Solutions The solution is suitable for application in the form of microdroplets.Examples F-4.1 to F-4.4: Granules The active ingredient of the invention is dissolved in dichloromethane, the solution is sprayed onto the carrier and then dissolved. The medium is evaporated in a vacuum.Examples F-5.1 to F-5.2: Dust A ready-to-use powder is obtained by homogeneously mixing all the ingredients.Examples F-6.1 to F-6.3: wettable powder Mix all the ingredients, grind the mixture thoroughly in a suitable mill, and dilute with water. A wettable powder is obtained which can give a suspension of any desired concentration.BIOLOGICAL EXAMPLES: A. Microbicidal activity Example B-1: Against Puccinia graminis in wheat Activity a) Residual-protective activity Six days after sowing, wheat plants were prepared with an aqueous spray mixture ( After spraying with the active ingredient (0.2%) to the point of dripping and after 24 hours the plants are fungal spores. Infect with suspension. Insulation time of 48 hours (environment: 20 ℃, 95 ~ 100% After (relative atmospheric humidity) the plants are placed in a greenhouse at 22 ° C. 12 days after infection, fungal invasion Evaluate (infestation).b) Penetration activity Five days after sowing, an aqueous spray mixture prepared with a wettable powder of the active ingredient Pour the active ingredient (0.006%) around the wheat plant. The spray mixture is above the plant Be careful not to touch. After 48 hours, the plants are spore suspension of fungi. Infect with suspension. Insulation time of 48 hours (environment: 20 ° C, 95-100% relative After atmospheric humidity) the plants are placed in a greenhouse at 22 ° C. Twelve days after infection, evaluation of fungal invasion Worth. The compounds of Tables 1 and 2 show good activity.Example B-2: Phytophthora in Tomato infestans) activity a) Residual protection activity Tomato plants were allowed to grow for 3 weeks and were prepared with a wettable powder of the active ingredient. Spray up to the point of dripping with a mist mixture (0.02% active ingredient) and after 24 hours Infect the sporangial suspension. The fungal invasion is 90% relative atmospheric humidity during the period from the infection. It is evaluated after 5 days of keeping the chair at 100% and a temperature of 20 ° C.b) Penetration activity Aqueous spray prepared by growing tomato plants for 3 weeks and then wettable powder of the active ingredient Pour the mixture (0.006% active ingredient based on soil volume) around them. Spray Take care that the mixture does not touch the aboveground parts of the plant. After 48 hours, the plants are sporangia suspension. Infect with suspension. The fungal invasion is 90 to 10 relative atmospheric humidity during the period from the infection. It is evaluated after 5 days of keeping at 0% and a temperature of 20 ° C. The compounds of Tables 1 and 2 show good activity.Example B-3: Cercospora arac in peanuts activity against hidicola) Peanut plants with a height of 10-15 cm prepared with a wettable powder formulation of the active ingredient Atomize with spray mixture (0.02% of active ingredient) and after 48 hours , Infected with a conidial suspension of the fungus. Insulate plants at about 21 ° C and high humidity for 72 hours And then place in a greenhouse until typical lesions occur. The activity of the active ingredient 12 days after infection Evaluation is based on the number and size of lesions. Compounds in Tables 1 and 2 Indicates good activity.Example B-4: Plasmopara viticola in vines activity against cola) Aqueous spray mix prepared from a 4- to 5-leaf stage grape seedling with a wettable powder of the active ingredient. Sprayed to the point of dripping with compound (active ingredient 0.02%) and after 24 hours fungal spores Infect the bladder suspension. The fungal invasion is 90% relative atmospheric humidity during the period from the infection. Evaluated after 6 days held at 100% and 20 ° C temperatures. Table 1 and Compound 2 has good activity.Example B-5: Colletorichum lagenarium in cucumber activity against lagenarium) Cucumber plants were grown for 2 weeks and then sprayed with a wettable powder of the active ingredient. Spray with a mist mixture (concentration 0.002%). Two days later, the plants were treated with a mixture of fungal spores (1 . 5 × 10^FiveSpores / ml) and incubate at 23 ° C and high humidity for 36 hours . Insulation is then continued at normal humidity and about 22 ° C. The fungal invasion that emerged is an infection Evaluate in 8 days Is done. The compounds of Tables 1 and 2 show good activity.Example B-6: Venturia inae on Apple qualis) residual-protective activity Prepared with a wettable powder of the active ingredient on a young apple sapling with a height of 10 to 20 cm. Spray mixture (0.02% of active ingredient) until 24 hours and The plants are then infected with a conidial suspension of the fungus. Plant for 5 days at 90-100% phase It is kept at atmospheric humidity and placed in a greenhouse at 20 to 24 ° C for 10 days. Infection 12 After days, evaluate the fungal invasion. The compounds of Tables 1 and 2 show good activity.Example B-7: Against Erysiphe graminis in barley Activity a) Residual-protective activity Aqueous spray mixing prepared with a wettable powder of the active ingredient to a barley plant with a height of about 8 cm. Spray with liquid (0.02% active ingredient) to the point of dripping and after 3 to 4 hours Sprinkle with conidia. Place the infected barley plant in a greenhouse at about 22 ° C and 1 The fungal invasion is evaluated 2 days later. The compounds of Tables 1 and 2 show good activity.b) Penetration activity Aqueous spray mixture prepared by wettable powder of active ingredient (based on soil volume Min. 0.002%) around barley plants about 8 cm high. Spray mixture is plant On the ground Be careful not to touch the parts. After 48 hours, the plants are sprinkled with conidia of the fungus. Feeling Place the dyed plants in a greenhouse at about 22 ° C and evaluate fungal invasion 12 days after infection. . The compounds of Tables 1 and 2 show good activity.Example B-8: Podosphaera in Young Apple Trees leucotricha) Residual-protective activity Spray mixture (0.06% of active ingredient) on young apple saplings with a height of 15 cm To spray. After 24 hours, the treated plants were infected with a conidial suspension of the fungus, and Place in a cabinet with a relative atmospheric humidity of 70% and a controlled environment of 20 ° C. infection After 12 days, fungal invasion is evaluated. The compounds of Tables 1 and 2 show good activity.Biological Examples: B. Acaricidal, insecticidal and nematicidal activity Example B-9: Tetranychus urticae (Acari) Activity against Populate a juvenile bean plant with a mixed population of Tetranyx urticae and one day later Spray an aqueous emulsion mixture containing 400 ppm min. The plants are then kept at 25 ° C for 6 days Keep warm and evaluate. Reduction rate (% activity) in the population is on treated plants Comparing the number of dead eggs, larvae and adults with those on untreated plants Measured by The compounds of Tables 1 and 2 show good activity.Example B-10: Tetranyx cinnavarinus in dwarf beans ( Activity against Tetranychus cinnabarinus) [Acari] Dilution series A mixed population of tetranix cinnavarinus, an OP-resistant variety of dwarf beans in the 2-leaf stage Populate (eggs, larvae / larvae and adults). 24 hours after infection, The active ingredient is applied to the plants in an automatic spraying chamber at an application rate of 200, 100 and 50 mg / l To use. The substance is formulated and diluted with water to give the concentration application rate. 2 and 7 days after application -Egg, -Larvae / larvae and -Adult It is evaluated by the mortality rate of. The compounds of Tables 1 and 2 at a low dilution similar to 50 mg / l of active ingredient are 70 It has a mortality rate of more than%.Example B-11: Nilaparavata lugens [insects] Activity against Rice plants are treated with an aqueous emulsion spray mixture containing 400 ppm active ingredient. With spray After the kimono has dried, rice plants are infested with second and third stage planthopper larvae. Evaluation Will take place 21 days later. Percentage reduction in population (% activity) survived treated plants It is determined by comparing the number of planthoppers with those in untreated plants. Table 1 And conversion of 2 The compound shows an activity of 90% or more.Example B-12: Plutella xylostella caterpillar [insects] Activity against Aqueous emulsion spray mixture of juvenile cabbage plants containing 400 ppm of the active ingredient of the present invention. Spray with. After the spray deposits have dried, the cabbage plants are cultivated in a third season of Plutella kil. Inhabit 10 Stella caterpillars and place them in a plastic container. Evaluation is 3 days later Will be The population reduction rate and the reduction rate due to feeding damage (% activity) are treated On untreated plants the number of dead caterpillars on the affected plants and the caterpillars damaged by feeding It is determined by comparing with. The compounds of Tables 1 and 2 show good activity.Example B-13: Against Musca domestica [insects] Activity Concentration of test substance in sugar is 250 ppm after overnight drying of sugar mass By treatment with a solution of the test substance. This treated mass and the wet cotton ball And 10 OP-resistant species Musca domestica adults are placed in an aluminum dish, Then, this is covered with a glass beaker and kept warm at 25 ° C. Death rate after 24 hours To measure. The compounds of Tables 1 and 2 show good activity.B-14: Heterodera glycines in soybean [Nematodes Activity against About 6000 eggs of soybean cyst nematode per pot in sandy soil: het Rodera Glicins (Heterode Infested with eggs of ra glycines). The test substance is then concentrated Mix in a degree. Then fill a 1c pot (180ccm) with the treated and contaminated soil. Seed and sow three soybeans (cv. Maple Arrow) per pot. Each process Repeat three times. Keep pots in the greenhouse at about 27 ° C for 4-5 weeks I do. Then carefully remove the plants from the pot, wash the roots, and remove the number of cysts. To measure. The compounds of Tables 1 and 2 as can be seen from the complete visual reduction in cyst formation. Shows good activity against Heterodera glycins.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.⁶ 識別記号庁内整理番号ＦＩＣ０７Ｄ 413/14 ２１５ 9159−4ＣＣ０７Ｄ 413/14 ２１５ ─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁶ Identification number Internal reference number FI C07D 413/14 215 9159-4C C07D 413/14 215

Claims

[Claims] 1. In each case in free form or salt form, the formula I [In the formula, the substituent A is at the 6- or 7-position, R₁Represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an alkyl group having 1 to 4 carbon atoms. Of alkoxy groups having 1, 2 or 3 halogen atoms, the number of halo-carbon atoms Represents an alkyl group having 1 to 4 or an alkylthio group having 1 to 4 carbon atoms; R₂And R_ThreeAre, independently of each other, a hydrogen atom or an alkyl having 1 to 4 carbon atoms. Group having 1 to 5 halogen atoms, halo-alkenyl having 1 to 4 carbon atoms Group, alkoxy group having 1 to 2 carbon atoms-alkyl having 1 to 4 carbon atoms Radicals, nitro-alkyl radicals having 1 to 4 carbon atoms, cyano-alkyl radicals having 1 to 4 carbon atoms A C4 alkyl group, a C1-4 alkanoyl-a C1-4 An alkyl group of 1 to 4 alkoxycarbonyl having 1 to 4 carbon atoms-having 1 carbon atom Isyl-4 alkyl group, C1 -C2 alkylthio-no C1 A 4 alkyl group, an alkyl group having 1 to 2 carbon atoms -Sulfinyl-alkyl group having 1 to 4 carbon atoms, having 1 to 2 carbon atoms Alkanesulfonyl-C1-C4 alkyl group, C2-C2 4 alkenyl groups, halo-carbon atoms having 1, 2 or 3 halogen atoms Alkenyl group having 2 to 4 carbon atoms, alkynyl group having 2 to 4 carbon atoms, carbon atom Cycloalkyl group having 3 to 7 carbon atoms, alkoxy group having 1 to 4 carbon atoms, halo -An alkoxy group having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms A group, a halo-alkylthio group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms Rukylsulfinyl group, alkylsulfonyl group having 1 to 4 carbon atoms, amino Group, acylamino group having 1 to 4 carbon atoms, nitro group, cyano group, hydroxy Represents a radical or a halogen atom; R_FourIs a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 Halo-halogen-containing alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom 1 to 2 alkoxy-C1 to C4 alkyl, nitro-carbon Alkyl group having 1 to 4 carbon atoms, cyano-alkyl group having 1 to 4 carbon atoms, carbon A cycloalkyl group having 3 to 5 atoms, a benzyl group, an alkyl group having 1 to 4 carbon atoms Lucanoyl group, benzoyl group; the phenyl group is unsubstituted or halogen Group consisting of atoms, alkyl groups having 1 or 2 carbon atoms, nitro groups and cyano groups Substituted with 1, 2 or 3 substituents selected from Represents a benzoyl group represented by R_FiveAnd R₆Are, independently of each other, a hydrogen atom and an alkyl group having 1 to 4 carbon atoms. Group having 1, 2, or 3 halogen atoms-halo-having 1 to 4 carbon atoms An alkyl group of 1 to 2 alkoxy having 1 to 2 carbon atoms and an alkyl group having 1 to 4 carbon atoms. Alkyl group, nitro-alkyl group having 1 to 4 carbon atoms, cyano-C 1 atom To C4 alkyl group, C1 to C4 alkoxycarbonyl-carbon atom An alkyl group having a child number of 1 to 4; or an unsubstituted or halogen atom and 1 or 2 position selected from the group consisting of alkyl groups having 1 to 2 carbon atoms Represents a cycloalkyl group having 3 to 6 carbon atoms substituted with a substituent; R₇Is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, cyclo Propyl group, alkoxy group having 1 to 4 carbon atoms or 1 to 4 carbon atoms Represents an alkylthio group of X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs a hydrogen atom; substituted or unsubstituted, having up to 12 carbon atoms Open chain, saturated or unsaturated hydrocarbon groups; substituted or unsubstituted, up to 10 Cyclic, saturated or unsaturated hydrocarbon groups containing carbon atoms; substituted or unsubstituted Represents a substituted or unsubstituted heterocyclic group; R₁₁Is a hydrogen atom; has up to 8 carbon atoms, and Substituted or 1 to 5 halogen atoms, alkoxy having 1 to 2 carbon atoms Group, hydroxyl group, nitro group, cyano group, alkanoy having 1 to 4 carbon atoms Radical, halo-alkanoyl group having 1 to 4 carbon atoms or having 1 carbon atom Open-chain, saturated or unsaturated carbon substituted by the alkoxycarbonyl group of 4 Hydrogenated group; cyclic, saturated or unsaturated hydrocarbon having 10 or less carbon atoms A group; or a carbocycle which is unsubstituted or has a halogen atom or 1 to 2 carbon atoms Depending on the alkyl group, halomethyl group, nitro group or cyano group of A substituted benzyl group; or an unsubstituted or C 1 -C 2 System consisting of alkyl group, halogen atom, halomethyl group, nitro group or cyano group Represents a heterocyclic group mono- or tri-substituted by the same or different substituents from a sequence ; R₁₂Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; or R₁₁And R₁₂Is unsubstituted, together with the nitrogen atom to which they are attached Alternatively, a halogen atom, an alkyl group having 1 to 2 carbon atoms, a halomethyl group or Is mono- or tri-substituted by the same or different substituents from the series consisting of nitro groups Represents a heterocycle. ] Or a tautomer thereof, if appropriate . 2. In the above formula, R_TenHas up to 8 carbon atoms and is unsubstituted or 1 to 5 halogen atoms and carbon atoms 1 to 2 alkoxy group, hydroxyl group, nitro group, cyano group, number of carbon atoms Also, an alkanoyl group having 1 to 4 and a halo-alkanoyl group having 1 to 4 carbon atoms Or an alkenyl group substituted with an alkoxycarbonyl group having 1 to 4 carbon atoms, Chain, saturated or unsaturated hydrocarbon group; cyclic, saturated, having 10 or less carbon atoms Or an unsaturated hydrocarbon group; or a carbocycle which is unsubstituted or a halogen atom , Alkyl groups having 1 or 2 carbon atoms, halomethyl groups, nitro groups or cyano A benzyl group mono- or di-substituted by a group; or unsubstituted or ha Rogen atom, alkyl group having 1 to 2 carbon atoms, halomethyl group, nitro group Or 1 to 3 substituents with the same or different substituents from the series consisting of 2. A heterocyclic group which is substituted or a 5- to 7-membered lactone ring is represented. A compound of formula I 3. In the above formula, R_TenHas a hydrogen atom, up to 12 carbon atoms and is unsubstituted Or by a tri (C1-4alkyl) silyl group or An open chain, saturated or unsaturated hydrocarbon group substituted by an epoxy group; or Group: -CH (U) (CH₂)_mCO-W [Wherein U is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cyano group or Represents an alkoxycarbonyl group having 1 to 6 carbon atoms; W is an alkoxy group having 1 to 6 carbon atoms, the number of carbon atoms 3 to 6 cycloalkoxy groups or groups: -N (T₁) T₂Represents; m represents 0, 1 or 2; and T₁And T₂Are, independently of one another, a hydrogen atom; unsubstituted or 1 to 3 halogen atoms, an alkoxy group having 1 to 2 carbon atoms, a hydroxyl group, Nitro group, cyano group, alkanoyl group having 1 to 4 carbon atoms, halo-carbon atom An alkanoyl group having 1 to 4 carbon atoms or an alkoxycarbox having 1 to 4 carbon atoms An alkyl group having 1 to 6 carbon atoms substituted with a bonyl group or unsubstituted Or an alkyl having 1 to 6 carbon atoms substituted with 1 to 3 halogen atoms Kenyl group, carbon which is unsubstituted or substituted by 1 to 3 halogen atoms Alkynyl groups having 1 to 6 atoms; cyclic, saturated, having 10 or less carbon atoms Or an unsaturated hydrocarbon group; or a carbocycle which is unsubstituted or a halogen atom , Alkyl groups having 1 or 2 carbon atoms, halomethyl groups, nitro groups or cyano A benzyl group mono- or di-substituted by a group; or unsubstituted or charcoal If an alkyl group having 1 to 2 elementary atoms, halogen atom, halomethyl group, nitro group Or 1 to 3 substituents with the same or different substituents from the series consisting of Represents a substituted heterocyclic group; or T₁And T₂As ring atoms together with the nitrogen atom to which they are attached Have O, S and / or N A 5- to 7-membered heterocycle, in which the additional nitrogen is unsubstituted Or an alkyl group having 1 to 4 carbon atoms, a phenyl group, or 1 carbon atom Substituted with an alkanoyl group, a benzoyl group or a benzyl group of , And the carbon atom of the heterocycle is unsubstituted or halogen atom, carbon atom From a series consisting of alkyl groups with 1 or 2 children, halomethyl groups or nitro groups Mono- or tri-substituted by the same or different substituents of. ) Is formed. ] The compound of formula I according to claim 1, which represents 4. In the above formula, R_TenIs a hydrogen atom, has up to 6 carbon atoms and is unsubstituted Or by a tri (C1-4 alkyl) silyl group or An open-chain, saturated or unsaturated hydrocarbon group substituted by a xy group; or the group: -CH₂-CO-W [In the formula, W is an alkoxy group having 1 to 6 carbon atoms, or is an alkoxy group having 3 to 6 carbon atoms. Cycloalkoxy group or group: -N (T₁) T₂Represents; T₁And T₂Are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms Halo-alkyl having 1 to 6 carbon atoms having 1 to 3 halogen atoms Groups, cycloalkyl groups having 3 to 6 carbon atoms, phenyl groups, 1 to 3 ha Represents a halo-phenyl group, a pyridyl group or a naphthyl group having a rogen atom; or Is T₁And T₂Together with the nitrogen atom they bind to With piperidine, piperazine, morpholine or 2,6-dimethylmorpholine Represent. ] The compound of formula I according to claim 3, which represents 5. In the above formula, R₁Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R₂Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 Halo-halogen-containing alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom 1-2 alkoxy-C1-4 alkyl, cyclopropyl Represents an ethynyl group or a halogen atom; R_ThreeRepresents a fluorine atom or a chlorine atom; R_FourRepresents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R_FiveRepresents an alkyl group having 1 to 4 carbon atoms; R₆Represents a hydrogen atom; R₇Represents a hydrogen atom or a halogen atom; X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs an alkyl group having 1 to 4 carbon atoms, a halogen source having 1, 2 or 3 carbon atoms Halo having 1 to 4 carbon atoms, having 1 to 2 carbon atoms Alkoxy-C1 -C4 alkyl, hydroxy-C1 Ishi 4 alkyl group, nitro-alkyl group having 1 to 4 carbon atoms, cyano-carbon No prime atom number 1 A C4 alkyl group, C1-4 alkanoyl-C1C4 A C4 alkyl group, a C1-4 alkoxycarbonyl-a C1 To 4 alkyl groups; unsubstituted or mono- or tri-substituted with halogen atoms. An alkenyl group having 2 to 4 carbon atoms; an alkynyl having 2 to 4 carbon atoms Group, cycloalkyl group having 3 to 7 carbon atoms, cycloalkyl group having 4 to 8 carbon atoms Alkenyl group, benzyl group; unsubstituted or halogen atom, 1 carbon atom 1 to 2 alkyl-, nitro- or cyano-substituted mono- or di-substituted phenyl groups Nyl group; or pyridine group, pyrimidine group or triazine group (these heterocycles Is an unsubstituted or halogen atom or an alkyl group having 1 to 2 carbon atoms. The same or from a system consisting of a kill group, a trifluoromethyl group or a cyano group or Mono- to tri-substituted by different groups. ) Or represents a 5-membered lactone ring; R₁₁Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 Halo-halogen-containing alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom 1-2 alkoxy-C1-4 alkyl, hydroxy-carbon An alkyl group having 1 to 4 atoms, a nitro-alkyl group having 1 to 4 carbon atoms, Cyano-alkyl group having 1 to 4 carbon atoms, alkano having 1 to 4 carbon atoms Ile-alkyl group having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms Carbonyl-carbon atom Alkyl groups of the numbers 1 to 4; unsubstituted or halogen atom at 1 to 3 positions A substituted alkenyl group having 2 to 4 carbon atoms; an alkenyl group having 2 to 4 carbon atoms A nyl group, a cycloalkyl group having 3 to 7 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms Chloalkenyl group, benzyl group; unsubstituted or halogen atom, carbon atom Mono- or di-substituted with an alkyl, nitro or cyano group of the formula 1 or 2 Represents a phenyl group; R₁₂Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; or R₁₁And R₁₂Is a pyrrolidine group together with the nitrogen atom to which they are attached , Piperidine group, piperazine group, morpholine group or 2,6-dimethylmorpholine A compound of formula I according to claim 1 which represents a phenyl group. 6. In the above formula, X is SR_TenThe compound according to claim 5, which is 7. In the above formula, X is OR_TenThe compound according to claim 5, which is 8. In the above formula, R₁Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ; R₂Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 1, 2 or 3 Halo-halogen-containing alkyl groups having 1 to 4 carbon atoms, having 1 carbon atom 1 to 2 alkoxy group-C1 to C4 alkyl group, cyclopropyl Group, ethynyl group or halogen atom Do; R_ThreeRepresents a chlorine atom; R_FourRepresents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R_FiveRepresents an alkyl group having 1 to 4 carbon atoms; R₆Represents a hydrogen atom; R₇Represents a hydrogen atom; X is OR_TenOr SR_TenRepresents; R_TenIs based on: -CH₂Represents -CO-W; W is an alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms Lucoxy group, or group -N (T₁) T₂Represents; T₁And T₂Are, independently of each other, a hydrogen atom and an alkyl group having 1 to 6 carbon atoms. Group having 1 to 3 halogen atoms, halo-alkane having 1 to 6 carbon atoms Kill group, cycloalkyl group having 3 to 6 carbon atoms, phenyl group, 1 to 3 Represents a halophenyl group, a pyridyl group or a naphthyl group having a halogen atom of Ruiha T₁And T₂Is a piperidine group together with the nitrogen atom to which they are attached, A piperazine group, a morpholine group or a 2,6-dimethylmorpholine group, A compound represented by formula I according to item 1. 9. The following formula I. 1 [Wherein, R₂Represents a hydrogen atom, a methyl group or an ethyl group; R_ThreeRepresents a fluorine atom or a chlorine atom; R_FiveRepresents a methyl group or an ethyl group; R₇Represents a hydrogen atom or a fluorine atom; X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs an alkyl group having 1 to 4 carbon atoms, a difluoromethyl group, trifluoro Methyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, vinyl Group, allyl group, 2-propynyl group, cyclopentyl group, cyclohexyl group, Chlorohexenyl group, cyanomethyl group or C1-C4 alkoxyl Represents a carbonyl group; R₁₁Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cyclohexyl group, a Represents a chloropropyl group or a phenyl group; R₁₂Represents a hydrogen atom; or R₁₁And R₁₂Together with the nitrogen atom they are attached to, piperidine Group, morpholine group or 2,6- Represents a dimethylmorpholine group. The compound of Claim 1 represented by these. 10. The following formula I. 2 (Where R₂Represents a hydrogen atom, a methyl group or an ethyl group; R_ThreeRepresents a fluorine atom or a chlorine atom; R_FiveRepresents a methyl group or an ethyl group; R₇Represents a hydrogen atom or a fluorine atom; X is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents; R_TenIs an alkyl group having 1 to 4 carbon atoms, a difluoromethyl group, trifluoro Methyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, vinyl Group, allyl group, 2-propynyl group, cyclopentyl group, cyclohexyl group, Chlorohexenyl group, cyanomethyl group or C1-C4 alkoxyl Represents a carbonyl group; R₁₁Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cyclohexyl group, a Represents a chloropropyl group or a phenyl group; R₁₂Represents a hydrogen atom; or R₁₁And R₁₂Together with the nitrogen atom they are attached to, piperidine Represents a group, a morpholine group or a 2,6-dimethylmorpholine group. ) The compound according to claim 1. 11. The following formula I. 1a (Where R_TenIs unsubstituted or mono- or tri-substituted by a halogen atom An alkyl group having 1 to 5 carbon atoms, or an unsubstituted or halogen atom Represents an alkenyl group having 2 to 5 carbon atoms which is mono- or tri-substituted by a child. ) The compound according to claim 1, which is represented by: 12. a) X is SR_TenIn order to prepare a compound of formula I: Formula II Where the substituent A is in the 6 or 7-position and R₁Through R₇Is given by the formula I The same as defined for it. ) And a compound of formula III R_Ten-Z (III) (Where R_TenHas the same meaning as defined in formula I, and Z is easily eliminated Represents a nucleofugic radical. Compound represented by) Reacting, preferably in the presence of a base; particularly preferably first of formula II Reacting a compound of formula III with a base and then reacting a compound of formula III By doing; or b) X is OR_TenOr N (R₁₁) R₁₂To produce a compound of formula I for: X is SR_TenA compound of formula I MX (IV) (In the formula, M is a hydrogen atom, Li⁺, Na⁺, K⁺, 1/2 Mg²⁺Or quaternary ammoni Represents the um ion; X is OR_TenOr N (R₁₁) R₁₂Represents and R_Ten, R₁₁And R₁₂Is in formula I Represents the same meaning as defined. ) And the presence of a base, if appropriate. Reacting under; or c) R_FourIs the same as defined in Formula I, but in formula I To produce the compound represented: R_FourIs a hydrogen atom and a compound of formula I and formula V R_Four‘−Z’ (V) (Where R_Four′ Is R in formula I_FourSame as defined for, but hydrogen atom And Z'represents a nucleofusic group which is easily eliminated. ) Reaction of the compound to be treated, preferably in the presence of a base, Item 10. A method for producing a compound represented by formula I according to item 1. 13. Formula VII Where the substituent A is in the 6 or 7-position and R₁Through R₇Is in formula I Same as defined. ) And a compound represented by Reaction with nyl or sulfuryl chloride to give a compound of formula VIII To obtain a compound of formula IV ' M-X '(IV') (In the formula, M is a hydrogen atom, Li⁺, Na⁺, K⁺, 1/2 Mg²⁺Or quaternary ammoni Represents the um ion; X'is OR_Ten, SR_TenOr N (R₁₁) R₁₂Represents and R_Ten, R₁₁And R₁₂ Represents the same meaning as defined in formula I. ) And a compound represented by A compound of formula I according to claim 1 which comprises reacting in the presence of a base. Method of manufacturing a product. 14． Formula IX Where the substituent A is in the 6 or 7-position and R₁Through R₇Is in formula I Same as defined. ) Is allowed to react with the compound represented by A process for producing the compound of formula I according to claim 1, which comprises 15. The oxidizing agent is iron (III) salt, SeO₂, MnO₂, H₂O₂, Br₂, Cl₂ , I₂, SO_Three, H₂SO_Four, HNO_Three, N-bromosuccinimide, 2,3-dic In the presence of loro-5,6-dicyano-1,4-benzoquinone or a dehydrogenation catalyst O₂15. The compound of claim 14, which is 16. Formula IX ' Where the substituent A is in the 6 or 7-position and R₁Through R₇And X Is the same as defined in Formula I and Z is a readily removable nucleotide. -It is a Zick group. ) In the presence of a base or an acid, the compound represented by A compound of formula I according to claim 1 which comprises reacting Method. 17． As an active ingredient, a formula in free form or in the form of a salt usable as a pesticide At least one of the compounds according to claim 1 represented by I as a suitable carrier material And a composition for protecting plants against attack by pests. 18. 18. The composition of claim 17, wherein the pest is a phytopathogenic microorganism. 19. 18. The pest according to claim 17, wherein the pest is an insect, acarina or nematode. Composition. 20. As an active ingredient, a formula in free form or in the form of a salt usable as a pesticide At least one of the compounds according to claim 2 represented by I as a suitable carrier material To protect plants against attack by pests, including Composition. 21. 21. The composition of claim 20, wherein the pest is a phytopathogenic microorganism. 22. 21. The composition according to claim 20, wherein the pest is an insect, acarid or nematode. . 23. A contract consisting of intimately mixing the active ingredient with auxiliaries and / or carrier materials. A method for producing the composition according to claim 17. 24. A compound according to claim 1 for protecting plants against attack by pests. Usage of things. 25. The use according to claim 24, wherein the pest is a phytopathogenic microorganism. 26. The use according to claim 24, wherein the pest is an insect, a mite or a nematode. 27. A compound according to claim 1 as an active ingredient in plants, plant parts and / or Protects plants against attack by pests consisting of applying to plant habitat how to. 28. Use according to claim 27, wherein the pest is a phytopathogenic microorganism. 29. The use according to claim 27, wherein the pest is an insect, a mite or a nematode. 30. As an active ingredient, the compound according to claim 2 is used for plants, plant parts and / or plants. The plants are protected against attack by pests, which consists of applying them to the habitat of the plants. Those who protect Law. 31. The use according to claim 30, wherein the pest is a phytopathogenic microorganism. 32. 31. Use according to claim 30, wherein the pest is an insect, acarid or nematode. 33. 28. The method of claim 27, wherein the seed is treated. 34. A seed treated according to claim 33.