JP2013536820A - 植物病原性菌類を防除するためのジチイン−テトラ(チオ)カルボキシイミド類 - Google Patents
植物病原性菌類を防除するためのジチイン−テトラ(チオ)カルボキシイミド類 Download PDFInfo
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- 230000007062 hydrolysis Effects 0.000 description 1
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- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- RGCDBVVJUKZRQW-UHFFFAOYSA-M tributyl(methyl)azanium;acetate Chemical compound CC([O-])=O.CCCC[N+](C)(CCCC)CCCC RGCDBVVJUKZRQW-UHFFFAOYSA-M 0.000 description 1
- DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- DXJLCRNXYNRGRA-UHFFFAOYSA-M tributyl(methyl)azanium;iodide Chemical compound [I-].CCCC[N+](C)(CCCC)CCCC DXJLCRNXYNRGRA-UHFFFAOYSA-M 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
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- 229920001285 xanthan gum Polymers 0.000 description 1
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
X1は、O又はSであり;
X2は、O又はSであり;
X3は、O又はSであり;
R1及びR2は、同一であるか又は異なっており、そして、それぞれ、水素であるか、ハロゲン、OR3若しくはCOR4で1置換若しくは多置換されていてもよいC1−C8−アルキルであるか、ハロゲン、C1−C4−アルキル若しくはC1−C4−ハロアルキルで1置換若しくは多置換されていてもよいC3−C7−シクロアルキルであるか、いずれの場合にもハロゲン、C1−C4−アルキル、C1−C4−ハロアルキル、COR4若しくはスルホニルアミノで1置換若しくは多置換されていてもよいアリール若しくはアリール−(C1−C4−アルキル)であり;
R3は、水素、C1−C4−アルキル若しくはC1−C4−アルキルカルボニルであるか、又は、ハロゲン、C1−C4−アルキル若しくはC1−C4−ハロアルキルで1置換若しくは多置換されていてもよいアリールであり;
R4は、ヒドロキシル、C1−C4−アルキル又はC1−C4−アルコキシである〕
で表される新規ジチインテトラ(チオ)カルボキシイミド及びその農薬的に活性な塩が見いだされた。
調製方法A
式(I)で表されるジチインテトラ(チオ)カルボキシイミドは、
第1段階において、式(VI)
で表されるコハク酸モノアミドを、場合により希釈剤の存在下において、過剰量の塩化チオニルと反応させ、次いで、第2段階において、過剰な塩化チオニルを除去し、そのようにして得られた生成物の混合物を、有機溶媒又は有機溶媒と水の混合物の中で、場合により相間移動触媒の存在下において、変換し、及び、最後に、クロマトグラフィープロセスによって、式(I)で表されるジチインテトラ(チオ)カルボキシイミドを単離することによって、調製することができる。
R5、R6、R7及びR8は、同一であるか又は異なっており、そして、それぞれ独立して、直鎖若しくは分子鎖のC1−C28−アルキル、C6−C10−アリール又はベンジルであり;
Xは、ハロゲン、硫酸水素アニオン、硫酸アニオン、リン酸二水素アニオン、リン酸水素アニオン、リン酸アニオン又は酢酸アニオン(好ましくは、臭素、塩素、フッ素、硫酸水素アニオン、硫酸アニオン、リン酸アニオン及び酢酸アニオン)であり;
Aは、N又はPである〕
で表される。
式(I)で表されるジチインテトラ(チオ)カルボキシイミドは、式(VII)
上記活性成分又は組成物を用いた植物及び植物の部分の本発明による処理は、慣習的な処理方法によって、例えば、浸漬、散布、噴霧、灌漑、気化、散粉、煙霧、ばらまき、泡状化、塗布、拡散(spreading−on)、灌水(灌注(drenching))、点滴潅漑などによって、直接的に行うか、又は、該活性成分又は組成物を植物及び植物の部分の周囲、生息環境若しくは貯蔵空間に作用させることにより行い、また、繁殖器官(propagation material)の場合、特に種子の場合には、さらに、乾式種子処理、湿式種子処理、スラリー種子処理、外被化(incrustation)、1層以上の被膜のコーティングによっても行う。さらに、該活性成分を微量散布法(ultra−low volume method)によって施用する(deploy)ことも可能であり、又は、該活性成分調製物若しくは該活性成分自体を土壌中に注入することも可能である。
(1) バシルス・ツリンギエンシス(Bacillus thuringiensis)に由来する殺虫性結晶タンパク質又はその殺虫活性を示す一部分、例えば、クリックモアら「Crickmore et al. (Microbiology and Molecular Biology Reviews 1998, 62, 807−813)」によって編集され、クリックモアら「Crickmore et al. (2005)」によって、オンライン「http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/」上で「バシルス・ツリンギエンシス(Bacillus thuringiensis)毒素命名法」において更新された殺虫性結晶タンパク質又はその殺虫活性を示す一部分、例えば、Cryタンパク質類(Cry1Ab、Cry1Ac、Cry1B、Cry1C、Cry1D、Cry1F、Cry2Ab、Cry3Aa、又は、Cry3Bb)のタンパク質若しくはその殺虫活性を示す一部分(例えば、EP−A 1999141、及び、WO 2007/107302)、又は、例えば米国特許出願第12/249,016号に記載されている合成遺伝子によってコードされているタンパク質;又は、
(2) バシルス・ツリンギエンシス(Bacillus thuringiensis)とは異なる第2の結晶タンパク質又はその一部分の存在下において殺虫活性を示す、バシルス・ツリンギエンシス(Bacillus thuringiensis)に由来する結晶タンパク質又はその一部分、例えば、Cry34結晶タンパク質とCry35結晶タンパク質で構成されているバイナリートキシン(Nat. Biotechnol. 2001, 19, 668−72; Applied Environm. Microbiol. 2006, 71, 1765−1774)、又は、Cry1A若しくはCry1Fタンパク質とCry2Aa若しくはCry2Ab若しくはCry2Aeタンパク質で構成されているバイナリートキシン(米国特許出願第12/214,022号、及び、EP 08010791.5);又は、
(3) バシルス・ツリンギエンシス(Bacillus thuringiensis)に由来する2種類の異なった殺虫性結晶タンパク質の一部分を含んでいる殺虫性ハイブリッドタンパク質、例えば、上記(1)のタンパク質のハイブリッド、又は、上記(2)のタンパク質のハイブリッド、例えば、トウモロコシイベントMON98034で産生されるCry1A.105タンパク質(WO 2007/027777);又は、
(4) 上記項目(1)〜(3)のいずれか1つのタンパク質において、標的昆虫種に対するさらに強い殺虫活性を得るために、及び/又は、影響を受ける標的昆虫種の範囲を拡大するために、及び/又は、クローニング若しくは形質転換に際してコード化DNA中に誘導された変化に起因して、幾つかのアミノ酸(特に、1〜10のアミノ酸)が別のアミノ酸で置き換えられていているもの、例えば、トウモロコシイベントMON863若しくはMON88017におけるCry3Bb1タンパク質又はトウモロコシイベントMIR604におけるCry3Aタンパク質;又は、
(5) バシルス・ツリンギエンシス(Bacillus thuringiensis)又はバシルス・セレウス(Bacillus cereus)に由来する殺虫性分泌タンパク質又はその殺虫活性を示す一部分、例えば、「http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html」において挙げられている栄養生長期殺虫性タンパク質(vegetative insecticidal protein)(VIP)、例えば、VIP3Aaタンパク質類のタンパク質;又は、
(6) バシルス・ツリンギエンシス(Bacillus thuringiensis)又はバシルス・セレウス(Bacillus cereus)に由来する第2の分泌タンパク質の存在下において殺虫活性を示す、バシルス・ツリンギエンシス(Bacillus thuringiensis)又はバシルス・セレウス(Bacillus cereus)に由来する分泌タンパク質、例えば、VIP1aタンパク質とVIP2Aタンパク質で構成されているバイナリートキシン(WO 94/21795);又は、
(7) バシルス・ツリンギエンシス(Bacillus thuringiensis)又はバシルス・セレウス(Bacillus cereus)に由来する異なった分泌タンパク質の一部分を含んでいる殺虫性ハイブリッドタンパク質、例えば、上記(1)のタンパク質のハイブリッド、又は、上記(2)のタンパク質のハイブリッド;又は、
(8) 上記項目(5)〜(7)のいずれか1つのタンパク質において、標的昆虫種に対するさらに強い殺虫活性を得るために、及び/又は、影響を受ける標的昆虫種の範囲を拡大するために、及び/又は、クローニング若しくは形質転換に際してコード化DNA中に誘導された変化(それでも、まだ、殺虫性タンパク質をコードしている)に起因して、幾つかのアミノ酸(特に、1〜10のアミノ酸)が別のアミノ酸で置き換えられていているもの、例えば、ワタイベントCOT102におけるVIP3Aaタンパク質;又は、
(9) バシルス・ツリンギエンシス(Bacillus thuringiensis)に由来する結晶タンパク質の存在下において殺虫活性を示す、バシルス・ツリンギエンシス(Bacillus thuringiensis)又はバシルス・セレウス(Bacillus cereus)に由来する分泌タンパク質、例えば、VIP3とCry1A若しくはCry1Fで構成されているバイナリートキシン(米国特許出願第61/126083号、及び、米国特許出願第61/195019号)、又は、VIP3タンパク質とCry2Aaタンパク質若しくはCry2Abタンパク質若しくはCry2Aeタンパク質で構成されているバイナリートキシン(米国特許出願第12/214,022号、及び、EP 08010791.5);又は、
(10) 上記(9)のタンパク質において、標的昆虫種に対するさらに強い殺虫活性を得るために、及び/又は、影響を受ける標的昆虫種の範囲を拡大するために、及び/又は、クローニング若しくは形質転換に際してコード化DNA中に導入された変化(それでも、まだ、殺虫性タンパク質をコードしている)に起因して、幾つかのアミノ酸(特に、1〜10のアミノ酸)が別のアミノ酸で置き換えられていているもの。
(a) 植物細胞内又は植物体内におけるポリ(ADP−リボース)ポリメラーゼ(PARP)遺伝子の発現及び/又は活性を低減させることが可能な導入遺伝子を含んでいる植物;
(b) 植物又は植物細胞のPARGコード化遺伝子の発現及び/又は活性を低減させることが可能なストレス耐性を強化する導入遺伝子を含んでいる植物;
(c) ニコチンアミダーゼ、ニコチン酸ホスホリボシルトランスフェラーゼ、ニコチン酸モノヌクレオチドアデニルトランスフェラーゼ、ニコチンアミドアデニンジヌクレオチドシンテターゼ又はニコチンアミドホスホリボシルトランスフェラーゼを包含するニコチンアミドアデニンジヌクレオチドサルベージ生合成経路の植物機能性酵素(plant−functional enzyme)をコードするストレス耐性を強化する導入遺伝子を含んでいる植物。
(1) 野生型の植物細胞又は植物において合成された澱粉と比較して、その物理化学的形質〔特に、アミロース含有量若しくはアミロース/アミロペクチン比、枝分かれ度、平均鎖長、側鎖の分布、粘性挙動、ゲル抵抗(gel resistance)、澱粉粒径及び/又は澱粉の粒子形態〕に関して改変されていて、特定の用途により適した変性澱粉を合成するトランスジェニック植物;
(2) 非澱粉炭水化物ポリマーを合成するか、又は、遺伝子組換えがなされていない野生型植物と比較して改変された特性を有する非澱粉炭水化物ポリマーを合成する、トランスジェニック植物〔その例は、ポリフルクトース(特に、イヌリン型及びレバン型のポリフルクトース)を産生する植物、α−1,4−グルカン類を産生する植物、α−1,6−分枝 α−1,4−グルカン類を産生する植物、及び、アルテルナンを産生する植物である〕;
(3) ヒアルロナンを産生するトランスジェニック植物;
(4) トランスジェニック植物又はハイブリッド植物、例えば、「可溶性固形物高含有量」、「低辛味」(LP)及び/又は「長期保存」(LS)などの特性を有するタマネギ。
(a) セルロースシンターゼ遺伝子の改変された形態を含んでいる植物(例えば、ワタ植物);
(b) rsw2相同核酸又はrsw3相同核酸の改変された形態を含んでいる植物(例えば、ワタ植物)、例えば、スクロースリン酸シンターゼの発現が増大しているワタ植物;
(c) スクロースシンターゼの発現が増大している植物(例えば、ワタ植物);
(d) 繊維細胞に基づいた原形質連絡のゲーティングのタイミングが(例えば、繊維選択的β−1,3−グルカナーゼのダウンレギュレーションを介して)改変されている植物(例えば、ワタ植物);
(e) 反応性が(例えば、nodCを包含するN−アセチルグルコサミントランスフェラーゼ遺伝子の発現及びキチンシンターゼ遺伝子の発現を介して)改変されている繊維を有する植物(例えば、ワタ植物)。
(a) オレイン酸含有量が高いオイルを産生する植物(例えば、ナタネ植物);
(b) リノレン酸含有量が低いオイルを産生する植物(例えば、ナタネ植物);
(c) 飽和脂肪酸のレベルが低いオイルを産生する植物(例えば、ナタネ植物)。
− 申請: 当該申請の識別番号。形質転換イベントについての技術的な記述は、APHISからそのウェブサイトにおいて入手可能な特定の申請書類の中に、当該申請番号を介して見いだすことができる。それらの記述は、参照によって本明細書中に開示される。
− 申請の拡張: 範囲又は期間の拡張が請求されている、先の申請についての言及。
− 会社: 当該申請を提出している個人の名称。
− 規制物: 当該植物種。
− トランスジェニック表現型: 形質転換イベントによって植物に付与された形質。
− 形質転換イベント又はライン: 規制除外が請求されている1つ又は複数のイベント(場合により、ラインとも称される)の名称。
− APHIS文書: 申請に関連してAPHISによって刊行されているか、又は、請求することでAPHISから入手することが可能な、種々の文書。
・ 例えば以下のような、うどんこ病病原体に起因する病害: ブルメリア属各種(Blumeria species)、例えば、ブルメリア・グラミニス(Blumeria graminis); ポドスファエラ属各種(Podosphaera species)、例えば、ポドスファエラ・レウコトリカ(Podosphaera leucotricha); スファエロテカ属各種(Sphaerotheca species)、例えば、スファエロテカ・フリギネア(Sphaerotheca fuliginea); ウンシヌラ属各種(Uncinula species)、例えば、ウンシヌラ・ネカトル(Uncinula necator);
・ 例えば以下のような、さび病病原体に起因する病害: ギムノスポランギウム属各種(Gymnosporangium species)、例えば、ギムノスポランギウム・サビナエ(Gymnosporangium sabinae); ヘミレイア属各種(Hemileia species)、例えば、ヘミレイア・バスタトリクス(Hemileia vastatrix); ファコプソラ属各種(Phakopsora species)、例えば、ファコプソラ・パキリジ(Phakopsora pachyrhizi)及びファコプソラ・メイボミアエ(Phakopsora meibomiae); プッシニア属各種(Puccinia species)、例えば、プッシニア・レコンジタ(Puccinia recondita)又はプッシニア・トリシチナ(Puccinia triticina); ウロミセス属各種(Uromyces species)、例えば、ウロミセス・アペンジクラツス(Uromyces appendiculatus);
・ 例えば以下のような、卵菌類(Oomycetes)の群の病原体に起因する病害: ブレミア属各種(Bremia species)、例えば、ブレミア・ラクツカエ(Bremia lactucae); ペロノスポラ属各種(Peronospora species)、例えば、ペロノスポラ・ピシ(Peronospora pisi)又はペロノスポラ・ブラシカエ(P. brassicae); フィトフトラ属各種(Phytophthora species)、例えば、フィトフトラ・インフェスタンス(Phytophthora infestans); プラスモパラ属各種(Plasmopara species)、例えば、プラスモパラ・ビチコラ(Plasmopara viticola); プセウドペロノスポラ属各種(Pseudoperonospora species)、例えば、プセウドペロノスポラ・フムリ(Pseudoperonospora humuli)又はプセウドペロノスポラ・クベンシス(Pseudoperonospora cubensis); ピシウム属各種(Pythium species)、例えば、ピシウム・ウルチムム(Pythium ultimum);
・ 例えば以下のものに起因する、斑点病(leaf blotch disease)及び萎凋病(leaf wilt disease): アルテルナリア属各種(Alternaria species)、例えば、アルテルナリア・ソラニ(Alternaria solani); セルコスポラ属各種(Cercospora species)、例えば、セルコスポラ・ベチコラ(Cercospora beticola); クラジオスポリウム属各種(Cladiosporium species)、例えば、クラジオスポリウム・ククメリヌム(Cladiosporium cucumerinum); コクリオボルス属各種(Cochliobolus species)、例えば、コクリオボルス・サチブス(Cochliobolus sativus)(分生子形態:Drechslera, 同義語:Helminthosporium); コレトトリクム属各種(Colletotrichum species)、例えば、コレトトリクム・リンデムタニウム(Colletotrichum lindemuthanium); シクロコニウム属各種(Cycloconium species)、例えば、シクロコニウム・オレアギヌム(Cycloconium oleaginum); ジアポルテ属各種(Diaporthe species)、例えば、ジアポルテ・シトリ(Diaporthe citri); エルシノエ属各種(Elsinoe species)、例えば、エルシノエ・ファウセッチイ(Elsinoe fawcettii); グロエオスポリウム属各種(Gloeosporium species)、例えば、グロエオスポリウム・ラエチコロル(Gloeosporium laeticolor); グロメレラ属各種(Glomerella species)、例えば、グロメレラ・シングラタ(Glomerella cingulata); グイグナルジア属各種(Guignardia species)、例えば、グイグナルジア・ビドウェリ(Guignardia bidwelli); レプトスファエリア属各種(Leptosphaeria species)、例えば、レプトスファエリア・マクランス(Leptosphaeria maculans); マグナポルテ属各種(Magnaporthe species)、例えば、マグナポルテ・グリセア(Magnaporthe grisea); ミクロドキウム属各種(Microdochium species)、例えば、ミクロドキウム・ニバレ(Microdochium nivale); ミコスファエレラ属各種(Mycosphaerella species)、例えば、ミコスファエレラ・グラミニコラ(Mycosphaerella graminicola)及びミコスファエレラ・フィジエンシス(M. fijiensis); ファエオスファエリア属各種(Phaeosphaeria species)、例えば、ファエオスファエリア・ノドルム(Phaeosphaeria nodorum); ピレノホラ属各種(Pyrenophora species)、例えば、ピレノホラ・テレス(Pyrenophora teres); ラムラリア属各種(Ramularia species)、例えば、ラムラリア・コロ−シグニ(Ramularia collo−cygni); リンコスポリウム属各種(Rhynchosporium species)、例えば、リンコスポリウム・セカリス(Rhynchosporium secalis); セプトリア属各種(Septoria species)、例えば、セプトリア・アピイ(Septoria apii); チフラ属各種(Typhula species)、例えば、チフラ・インカルナタ(Typhula incarnata); ベンツリア属各種(Venturia species)、例えば、ベンツリア・イナエクアリス(Venturia inaequalis);
・ 例えば以下のものに起因する、根及び茎の病害: コルチシウム属各種(Corticium species)、例えば、コルチシウム・グラミネアルム(Corticium graminearum); フサリウム属各種(Fusarium species)、例えば、フサリウム・オキシスポルム(Fusarium oxysporum); ガエウマンノミセス属各種(Gaeumannomyces species)、例えば、ガエウマンノミセス・グラミニス(Gaeumannomyces graminis); リゾクトニア属各種(Rhizoctonia species)、例えば、リゾクトニア・ソラニ(Rhizoctonia solani); タペシア属各種(Tapesia species)、例えば、タペシア・アクホルミス(Tapesia acuformis); チエラビオプシス属各種(Thielaviopsis species)、例えば、チエラビオプシス・バシコラ(Thielaviopsis basicola);
・ 例えば以下のものに起因する、穂の病害(ear and panicle disease)(トウモロコシの穂軸を包含する): アルテルナリア属各種(Alternaria species)、例えば、アルテルナリア属種(Alternaria spp.); アスペルギルス属各種(Aspergillus species)、例えば、アスペルギルス・フラブス(Aspergillus flavus); クラドスポリウム属各種(Cladosporium species)、例えば、クラドスポリウム・クラドスポリオイデス(Cladosporium cladosporioides); クラビセプス属各種(Claviceps species)、例えば、クラビセプス・プルプレア(Claviceps purpurea); フサリウム属各種(Fusarium species)、例えば、フサリウム・クルモルム(Fusarium culmorum); ジベレラ属各種(Gibberella species)、例えば、ジベレラ・ゼアエ(Gibberella zeae); モノグラフェラ属各種(Monographella species)、例えば、モノグラフェラ・ニバリス(Monographella nivalis); セプトリア属各種(Septoria species)、例えば、セプトリア・ノドルム(Septoria nodorum);
・ 例えば以下のものなどの、黒穂病菌類(smut fungi)に起因する病害: スファセロテカ属各種(Sphacelotheca species)、例えば、スファセロテカ・レイリアナ(Sphacelotheca reiliana); チレチア属各種(Tilletia species)、例えば、チレチア・カリエス(Tilletia caries)、チレチア・コントロベルサ(T. controversa); ウロシスチス属各種(Urocystis species)、例えば、ウロシスチス・オクルタ(Urocystis occulta); ウスチラゴ属各種(Ustilago species)、例えば、ウスチラゴ・ヌダ(Ustilago nuda)、ウスチラゴ・ヌダ・トリシチ(U. nuda tritici);
・ 例えば以下のものに起因する、果実の腐敗(fruit rot): アスペルギルス属各種(Aspergillus species)、例えば、アスペルギルス・フラブス(Aspergillus flavus); ボトリチス属各種(Botrytis species)、例えば、ボトリチス・シネレア(Botrytis cinerea); ペニシリウム属各種(Penicillium species)、例えば、ペニシリウム・エクスパンスム(Penicillium expansum)及びペニシリウム・プルプロゲヌム(P. purpurogenum); スクレロチニア属各種(Sclerotinia species)、例えば、スクレロチニア・スクレロチオルム(Sclerotinia sclerotiorum); ベルチシリウム属各種(Verticilium species)、例えば、ベルチシリウム・アルボアトルム(Verticilium alboatrum);
・ 例えば以下のものに起因する、種子及び土壌によって媒介される腐敗病及び萎凋病(seed− and soil−borne rot and wilt disease)並びに実生の病害: フサリウム属各種(Fusarium species)、例えば、フサリウム・クルモルム(Fusarium culmorum); フィトフトラ属各種(Phytophthora species)、例えば、フィトフトラ・カクトルム(Phytophthora cactorum); ピシウム属各種(Pythium species)、例えば、ピシウム・ウルチムム(Pythium ultimum); リゾクトニア属各種(Rhizoctonia species)、例えば、リゾクトニア・ソラニ(Rhizoctonia solani); スクレロチウム属各種(Sclerotium species)、例えば、スクレロチウム・ロルフシイ(Sclerotium rolfsii);
・ 例えば以下のものに起因する、癌性病害(cancer)、こぶ(gall)及び天狗巣病(witches’ broom): ネクトリア属各種(Nectria species)、例えば、ネクトリア・ガリゲナ(Nectria galligena);
・ 例えば以下のものに起因する、萎凋病(wilt disease): モニリニア属各種(Monilinia species)、例えば、モニリニア・ラキサ(Monilinia laxa);
・ 例えば以下のものに起因する、葉、花及び果実の奇形: タフリナ属各種(Taphrina species)、例えば、タフリナ・デホルマンス(Taphrina deformans);
・ 例えば以下のものに起因する、木本植物の衰退性病害(degenerative disease): エスカ属各種(Esca species)、例えば、ファエモニエラ・クラミドスポラ(Phaemoniella clamydospora)及びファエオアクレモニウム・アレオフィルム(Phaeoacremonium aleophilum)及びフォミチポリア・メジテラネア(Fomitiporia mediterranea;
・ 例えば以下のものに起因する、花及び種子の病害: ボトリチス属各種(Botrytis species)、例えば、ボトリチス・シネレア(Botrytis cinerea);
・ 例えば以下のものに起因する、植物塊茎の病害: リゾクトニア属各種(Rhizoctonia species)、例えば、リゾクトニア・ソラニ(Rhizoctonia solani); ヘルミントスポリウム属各種(Helminthosporium species)、例えば、ヘルミントスポリウム・ソラニ(Helminthosporium solani);
・ 例えば以下のものなどの、細菌性病原体に起因する病害: キサントモナス属各種(Xanthomonas species)、例えば、キサントモナス・カムペストリス pv.オリザエ(Xanthomonas campestris pv. oryzae); シュードモナス属各種(Pseudomonas species)、例えば、シュードモナス・シリンガエ pv.ラクリマンス(Pseudomonas syringae pv. lachrymans); エルビニア属各種(Erwinia species)、例えば、エルビニア・アミロボラ(Erwinia amylovora)。
・ 例えば以下のものに起因する、葉、茎、鞘及び種子の菌類病:
アルテルナリア斑点病(Alternaria leaf spot)(Alternaria spec. atrans tenuissima)、炭疽病(Colletotrichum gloeosporoides dematium var. truncatum)、褐紋病(brown spot)(Septoria glycines)、紫斑病(cercospora leaf spot and blight)(Cercospora kikuchii)、コアネホラ葉枯病(choanephora leaf blight)(Choanephora infundibulifera trispora(Syn.))、ダクツリオホラ斑点病(dactuliophora leaf spot)(Dactuliophora glycines)、べと病(Peronospora manshurica)、ドレクスレラ胴枯病(drechslera blight)(Drechslera glycini)、斑点病(frogeye leaf spot)(Cercospora sojina)、そばかす病(leptosphaerulina leaf spot)(Leptosphaerulina trifolii)、灰星病(phyllostica leaf spot)(Phyllosticta sojaecola)、黒点病(pod and stem blight)(Phomopsis sojae)、うどんこ病(Microsphaera diffusa)、ピレノカエタ斑点病(pyrenochaeta leaf spot)(Pyrenochaeta glycines)、葉腐病(rhizoctonia aerial, foliage, and web blight)(Rhizoctonia solani)、さび病(Phakopsora pachyrhizi, Phakopsora meibomiae)、黒とう病(Sphaceloma glycines)、ステムフィリウム葉枯病(stemphylium leaf blight)(Stemphylium botryosum)、褐色輪紋病(Corynespora cassiicola);
・ 例えば以下のものに起因する、根及び茎基部の菌類病:
黒根腐病(Calonectria crotalariae)、炭腐病(Macrophomina phaseolina)、赤かび病(fusarium blight or wilt, root rot, and pod and collar rot)(Fusarium oxysporum、Fusarium orthoceras、Fusarium semitectum、Fusarium equiseti)、ミコレプトジスクス根腐病(mycoleptodiscus root rot)(Mycoleptodiscus terrestris)、根腐病(neocosmospora)(Neocosmopspora vasinfecta)、黒点病(Diaporthe phaseolorum)、茎腐爛病(stem canker)(Diaporthe phaseolorum var. caulivora)、茎疫病(phytophthora rot)(Phytophthora megasperma)、落葉病(brown stem rot)(Phialophora gregata)、根茎腐敗病(pythium rot)(Pythium aphanidermatum、Pythium irregulare、Pythium debaryanum、Pythium myriotylum、Pythium ultimum)、リゾクトニア根腐病(rhizoctonia root rot, stem decay, and damping−off)(Rhizoctonia solani)、菌核病(sclerotinia stem decay)(Sclerotinia sclerotiorum)、スクレロチニアサウザンブライト病(sclerotinia southern blight)(Sclerotinia rolfsii)、チエラビオプシス根腐病(thielaviopsis root rot)(Thielaviopsis basicola)。
・ 植物の部分、例えば、葉を処理する場合: 0.1〜10000g/ha、好ましくは、10〜1000g/ha、さらに好ましくは、50〜300g/ha(灌水又は滴下によって施用する場合、特に、ロックウール又はパーライトなどの不活性底土を用いる場合には、上記施用量はさらに低減させることができる);
・ 種子を処理する場合: 種子100kg当たり2〜200g、好ましくは、種子100kg当たり3〜150g、さらに好ましくは、種子100kg当たり2.5〜25g、さらに一層好ましくは、種子100kg当たり2.5〜12.5g;
・ 土壌処理の場合: 0.1〜10000g/ha、好ましくは、1〜5000g/ha。
実施例1
段階A:
分析HPLC条件
単離されたフラクションを水で1+2に希釈し、45分間以内に、Strata X33 Polymeric Sorbent 60mg固相抽出カートリッジに吸い込ませる。そのカートリッジを、アルゴンを用いて1時間乾燥させ、1mLの重水素−THFで溶離させる。
実施例A: フィトフトラ(Phytophthora)試験(トマト)/保護
溶媒: 24.5重量部のアセトン
24.5重量部のジメチルアセトアミド
乳化剤: 1重量部のアルキルアリールポリグリコールエーテル
活性成分の適切な製剤を調製するために、1重量部の活性成分を上記量の溶媒及び乳化剤と混合し、得られた濃厚物を水で希釈して、所望の濃度とする。保護活性について試験するために、幼植物に、活性成分の該製剤を記載されている施用量で噴霧する。その噴霧による被膜が乾燥した後、該植物に、フィトフトラ・インフェスタンス(Phytophthora infestans)の胞子の水性懸濁液を用いて接種する。次いで、その植物を、約20℃で相対空気湿度100%のインキュベーション室の中に置く。評価は、上記接種の3日後に実施する。0%は、対照の効力に相当する効力を意味し、100%の効力は、感染が観察されないことを意味する。この試験において、以下の本発明化合物は、250ppmの活性成分濃度で、70%以上の効力を示す。
溶媒: 24.5重量部のアセトン
24.5重量部のジメチルアセトアミド
乳化剤: 1重量部のアルキルアリールポリグリコールエーテル
活性成分の適切な製剤を調製するために、1重量部の活性成分を上記量の溶媒及び乳化剤と混合し、得られた濃厚物を水で希釈して、所望の濃度とする。保護活性について試験するために、幼植物に、活性成分の該製剤を記載されている施用量で噴霧する。その噴霧による被膜が乾燥した後、該植物に、プラスモパラ・ビチコラ(Plasmopara viticola)の胞子の水性懸濁液を用いて接種し、次いで、その植物を、約20℃で相対空気湿度100%のインキュベーション室の中に1日間置く。次いで、その植物を、約21℃で空気湿度約90%の温室の中に4日間置く。次いで、その植物を湿らせ、インキュベーション室内に1日間置く。評価は、上記接種の6日後に実施する。0%は、対照の効力に相当する効力を意味し、100%の効力は、感染が観察されないことを意味する。この試験において、以下の本発明化合物は、250ppmの活性成分濃度で、70%以上の効力を示す。
溶媒: 24.5重量部のアセトン
24.5重量部のジメチルアセトアミド
乳化剤: 1重量部のアルキルアリールポリグリコールエーテル
活性成分の適切な製剤を調製するために、1重量部の活性成分を上記量の溶媒及び乳化剤と混合し、得られた濃厚物を水で希釈して、所望の濃度とする。保護活性について試験するために、幼植物に、活性成分の該製剤を記載されている施用量で噴霧する。その噴霧による被膜が乾燥した後、該植物に、リンゴ黒星病の病原であるベンツリア・イナエクアリス(Venturia inaequalis)の分生子の水性懸濁液を用いて接種し、次いで、その植物を、約20℃で相対空気湿度100%のインキュベーション室の中に1日間置く。次いで、その植物を、約21℃で相対空気湿度約90%の温室の中に置く。評価は、上記接種の10日後に実施する。0%は、対照の効力に相当する効力を意味し、100%の効力は、感染が観察されないことを意味する。この試験において、以下の本発明化合物は、250ppmの活性成分濃度で、70%以上の効力を示す。
溶媒: 24.5重量部のアセトン
24.5重量部のジメチルアセトアミド
乳化剤: 1重量部のアルキルアリールポリグリコールエーテル
活性成分の適切な製剤を調製するために、1重量部の活性成分を上記量の溶媒及び乳化剤と混合し、得られた濃厚物を水で希釈して、所望の濃度とする。保護活性について試験するために、幼植物に、活性成分の該製剤を記載されている施用量で噴霧する。その噴霧による被膜が乾燥した後、該植物に、アルテルナリア・ソラニ(Alternaria solani)の胞子の水性懸濁液を用いて接種する。次いで、その植物を、約20℃で相対空気湿度100%のインキュベーション室の中に置く。評価は、上記接種の3日後に実施する。0%は、対照の効力に相当する効力を意味し、100%の効力は、感染が観察されないことを意味する。この試験において、以下の本発明化合物は、250ppmの活性成分濃度で、70%以上の効力を示す。
Claims (11)
- 式(I)
X1は、O又はSであり;
X2は、O又はSであり;
X3は、O又はSであり;
R1及びR2は、同一であるか又は異なっており、そして、それぞれ、水素であるか、ハロゲン、OR3若しくはCOR4で1置換若しくは多置換されていてもよいC1−C8−アルキルであるか、ハロゲン、C1−C4−アルキル若しくはC1−C4−ハロアルキルで1置換若しくは多置換されていてもよいC3−C7−シクロアルキルであるか、いずれの場合にもハロゲン、C1−C4−アルキル、C1−C4−ハロアルキル、COR4若しくはスルホニルアミノで1置換若しくは多置換されていてもよいアリール若しくはアリール−(C1−C4−アルキル)であり;
R3は、水素、C1−C4−アルキル若しくはC1−C4−アルキルカルボニルであるか、又は、ハロゲン、C1−C4−アルキル若しくはC1−C4−ハロアルキルで1置換若しくは多置換されていてもよいアリールであり;
R4は、ヒドロキシル、C1−C4−アルキル又はC1−C4−アルコキシである〕
で表されるジチインテトラ(チオ)カルボキシイミド及びその農薬的に活性な塩。 - R1及びR2が、同一であるか又は異なっており、そして、それぞれ、水素であるか、フッ素、塩素、臭素、OR3若しくはCOR4で1置換若しくは多置換されていてもよいC1−C6−アルキルであるか、塩素、メチル若しくはトリフルオロメチルで1置換若しくは多置換されていてもよいC3−C7−シクロアルキルであるか、いずれの場合にもフッ素、塩素、臭素、メチル、トリフルオロメチル、COR4若しくはスルホニルアミノで1置換若しくは多置換されていてもよいフェニル若しくはフェニル−(C1−C4−アルキル)であり;
R3が、水素、メチル、エチル、メチルカルボニル若しくはエチルカルボニルであるか、又は、フッ素、塩素、メチル、エチル、n−プロピル、イソプロピル若しくはトリフルオロメチルで1置換若しくは多置換されていてもよいフェニルであり;
R4が、ヒドロキシル、メチル、エチル、メトキシ又はエトキシである;
請求項1に記載の式(I)で表されるジチインテトラ(チオ)カルボキシイミド。 - R1及びR2が、それぞれ、メチルである;
請求項1に記載の式(I)で表されるジチインテトラ(チオ)カルボキシイミド。 - 有害な植物病原性菌類を防除する方法であって、請求項1、2、3、4、5又は6に記載の式(I)で表されるジチインテトラ(チオ)カルボキシイミドを有害な植物病原性菌類及び/又はそれらの生息環境に施用することを特徴とする、前記方法。
- 有害な植物病原性菌類を防除するための組成物であって、増量剤及び/又は界面活性剤に加えて請求項1、2、3、4、5又は6に記載の式(I)で表される少なくとも1種類のジチインテトラ(チオ)カルボキシイミドを含んでいることを特徴とする、前記組成物。
- 有害な植物病原性菌類を防除するための、請求項1、2、3、4、5又は6に記載の式(I)で表されるジチインテトラ(チオ)カルボキシイミドの組成物の使用。
- 有害な植物病原性菌類を防除するための組成物を製造する方法であって、請求項1、2、3、4、5又は6に記載の式(I)で表されるジチインテトラ(チオ)カルボキシイミドを増量剤及び/又は界面活性剤と混合させることを特徴とする、前記方法。
- 請求項1、2、3、4、5又は6に記載の式(I)で表されるジチインテトラ(チオ)カルボキシイミドを調製する方法であって、
(A) 第1段階において、式(VI)
で表されるコハク酸モノアミドを、場合により希釈剤の存在下において、過剰量の塩化チオニルと反応させ、次いで、第2段階において、過剰な塩化チオニルを除去し、そのようにして得られた生成物の混合物を、有機溶媒と水の混合物の中で、場合により相間移動触媒の存在下において、変換し、及び、最後に、クロマトグラフィープロセスによって、式(I)で表されるジチインテトラ(チオ)カルボキシイミドを単離すること;
又は、
(B) 式(VII)
で表されるジクロロマレイミドを、溶媒又は溶媒混合物の中で、式(VIII)
で表されるジクロロマレイミド及び無機チオスルフェートと反応させること;
を特徴とする、前記方法。
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US20120225923A1 (en) | 2012-09-06 |
AU2011298432A1 (en) | 2013-03-28 |
GT201300056A (es) | 2014-07-23 |
TWI496540B (zh) | 2015-08-21 |
EP2611813A1 (de) | 2013-07-10 |
AR082800A1 (es) | 2013-01-09 |
AU2011298432B2 (en) | 2015-04-09 |
ZA201302371B (en) | 2014-09-25 |
CN103328484A (zh) | 2013-09-25 |
UA109669C2 (uk) | 2015-09-25 |
TW201216857A (en) | 2012-05-01 |
CL2013000597A1 (es) | 2013-08-09 |
RU2013114730A (ru) | 2014-10-10 |
WO2012028587A1 (de) | 2012-03-08 |
JP5869573B2 (ja) | 2016-02-24 |
CA2809908A1 (en) | 2012-03-08 |
CO6690750A2 (es) | 2013-06-17 |
EP2611813B1 (de) | 2015-01-21 |
ECSP13012501A (es) | 2013-05-31 |
US8524916B2 (en) | 2013-09-03 |
KR20140000671A (ko) | 2014-01-03 |
BR112013005230A2 (pt) | 2016-05-03 |
MX2013002260A (es) | 2013-05-22 |
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