JP7348904B2 - 新規な結晶形態 - Google Patents
新規な結晶形態 Download PDFInfo
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- JP7348904B2 JP7348904B2 JP2020543281A JP2020543281A JP7348904B2 JP 7348904 B2 JP7348904 B2 JP 7348904B2 JP 2020543281 A JP2020543281 A JP 2020543281A JP 2020543281 A JP2020543281 A JP 2020543281A JP 7348904 B2 JP7348904 B2 JP 7348904B2
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- methyl
- dichlorophenyl
- species
- trifluoromethyl
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
a=15.52ű0.01Å、b=7.24ű0.01Å、c=16.64ű0.01Å、α=90°±0.01°、β=105.03±0.01°、γ=90°±0.01°、Z=4。
a=7.27ű0.01Å、b=9.32ű0.01Å、c=14.11ű0.01Å、α=75.53°±0.01°、β=87.03±0.01°、γ=71.48°±0.01°、Z=2。
内部寄生性線虫、半内部寄生性線虫及び外部寄生性線虫、特に、植物寄生線虫、例えば、ネコブ線虫、キタネコブセンチュウ(Meloidogyne hapla)、サツマイモネコブセンチュウ(Meloidogyne incognita)、ジャワネコブセンチュウ(Meloidogyne javanica)、アレナリアネコブセンチュウ(Meloidogyne arenaria)及び他のネコブセンチュウ(Meloidogyne)種;嚢腫形成線虫、ジャガイモシストセンチュウ(Globodera rostochiensis)及び他のグロボデラ(Globodera)種;ムギシストセンチュウ(Heterodera avenae)、ダイズシストセンチュウ(Heterodera glycines)、テンサイシストセンチュウ(Heterodera schachtii)、クロバーシストセンチュウ(Heterodera trifolii)、及び他のシストセンチュウ(Heterodera)種;タネコブ線虫、アングイナ(Anguina)種;ナミクキ線虫、アフェレンコイデス属(Aphelenchoides)の種;刺毛線虫、エエロノライムス・ロンギカウダツス(Eelonolaimus longicaudatus)及び他のベロノライムス(Belonolaimus)種;マツ線虫、マツノザイセンチュウ(Bursaphelenchus xylophilus)及び他のマツノザイセンチュウ(Bursaphelenchus)種;ワ線虫、クリコネマ(Criconema)種、クリコネメラ(Criconemella)種、クリコネモイデス(Criconemoides)種、メソクリコネマ(Mesocriconema)種;ナミクキ線虫、イモグサレセンチュウ(Ditylenchus destructor)、ナミクキセンチュウ(Ditylenchus dipsaci)及び他のジチレンクス(Ditylenchus)種;キリ線虫、ドリコドルス(Dolichodorus)種;ラセン線虫、ヘリオコチレンクス・マルチシンクツス(Heliocotylenchus multicinctus)及び他のヘリオコチレンクス(Helicotylenchus)種;鞘及び鞘様線虫、ヘミシクリオホラ(Hemicycliophora)種及びヘミクリコネモイデス(Hemicriconemoides)種;ヒルシュマンニエラ(Hirshmanniella)種;ヤリ線虫、ホプロアイムス(Hoploaimus)種;ニセネコブ線虫、ナコッブス(Nacobbus)種;ハリ線虫、ロンギドルス・エロンガツス(Longidorus elongatus)及び他のロンギドルス(Longidorus)種;ピン線虫、プラチレンクス(Pratylenchus)種;病巣線虫、ムギネグサレセンチュウ(Pratylenchus neglectus)、キタネグサレセンチュウ(Pratylenchus penetrans)、プラチレンクス・クルビタツス(Pratylenchus curvitatus)、プラチレンクス・ゴオデイ(Pratylenchus goodeyi)及び他のプラチレンクス(Pratylenchus)種;ネモグリ線虫、ラドホルス・シミリス(Radopholus similis)及び他のラドホルス(Radopholus)種;ニセフクロ線虫、ロチレンクス・ロブスツス(Rotylenchus robustus)、ロチレンクス・レニホルミス(Rotylenchus reniformis)及び他のロチレンクス(Rotylenchus)種;スクテロネマ(Scutellonema)種;ユミハリ線虫、トリコドルス・プリミチブス(Trichodorus primitivus)及び他のトリコドルス(Trichodorus)種、パラトリコドルス(Paratrichodorus)種;イシュク線虫、チレンコリンクス・クライトニ(Tylenchorhynchus claytoni)、チレンコリンクス・ズビウス(Tylenchorhynchus dubius)及び他のチレンコリンクス(Tylenchorhynchus)種;ミカン線虫、チレンクルス(Tylenchulus)種;オオハリ線虫、キシフィネマ(Xiphinema)種;並びに他の植物寄生線虫種、例えば、スバングイナ(Subanguina)亜種、ヒプソペリン(Hypsoperine)亜種、マクロポストニア(Macroposthonia)亜種、メリニウス(Melinius)亜種、プンクトデラ(Punctodera)亜種、及びキニスルシウス(Quinisulcius)亜種
である。
不完全菌類(fungi imperfecti)(例えば、ボトリチス属(Botrytis)、ピリクラリア属(Pyricularia)、ヘルミントスポリウム属(Helminthosporium)、フザリウム属(Fusarium)、セプトリア属(Septoria)、セルコスポラ属(Cercospora)及びアルテルナリア属(Alternaria));担子菌綱(Basidiomycetes)(例えば、リゾクトニア属(Rhizoctonia)、ヘミレイア属(Hemileia)、プッシニア属(Puccinia));子嚢菌綱(Ascomycetes)(例えば、ベンツリア属(Venturia)及びエリシフ属(Erysiphe)、ポドスファエラ属(Podosphaera)、モニリニア属(Monilinia)、ウンシヌラ属(Uncinula));卵菌綱(Oomycetes)(例えば、フィトフトラ属(Phytophthora)、フィチウム属(Pythium)、プラスモパラ属(Plasmopara));接合菌綱(Zygomycetes)(例えば、リゾプス属(Rhizopus)の種);ファコプソラ科(Phakopsoraceae)、特に、ファコプソラ(Phakopsora)属のもの、例えば、アジアダイズさび病とまた呼ばれるファコプソラ・パキリジ(Phakopsora pachyrhizi)、及びプクキニア科(Pucciniaceae)のもの、特に、プッシニア(Puccinia)属のもの、例えば、穀類用植物における問題のある病害であるムギ黒さび病又は黒さび病としてもまた知られているプッシニア・グラミニス(Puccinia graminis)、及び褐さび病としてまた知られているプッシニア・レコンジタ(Puccinia recondita)
である。
-コムギ、下記の種子病害の防除に関して:フザリウム(fusaria)(ミクロドキウム・ニバル(Microdochium nivale)及びフザリウム・ロゼウム(Fusarium roseum))、ムギ黒穂病(チレチア・カリエス(Tilletia caries)、チレチア・コントロベルサ(Tilletia controversa)又はチレチア・インジカ(Tilletia indica))、セプトリア病(セプトリア・ノドルム(Septoria nodorum))及び裸黒穂病;
-コムギ、植物の地上部の下記の病害の防除に関して:穀類眼紋病(タペシア・ヤルンダ(Tapesia yallundae)、タペシア・アクイホルミス(Tapesia acuiformis))、立枯れ病(ガオイマンノミセス・グラミニス(Gaeumannomyces graminis))、赤かび病(フザリウム・クルモルム(F.culmorum)、フザリウム・グラミネアルム(F.graminearum))、ブラックスペック(リゾクトニア・セレアリス(Rhizoctonia cerealis))、ウドンコ病(エリシフェグラミニスフォルマスペキエトリティキ(Erysiphe graminis forma specie tritici))、サビ病(プッシニア・ストリイホルミス(Puccinia striiformis)及びプッシニア・レコンジタ(Puccinia recondita))並びにセプトリア病(セプトリア・トリチシ(Septoria tritici)及びセプトリア・ノドルム(Septoria nodorum));
-コムギ及びオオムギ、細菌性及びウイルス性病害の防除に関して、例えば、オオムギ黄色モザイク病;-オオムギ、下記の種子病害の防除に関して:網斑病(ピレノホラ・グラミネア(Pyrenophora graminea)、ピレノホラ・テレス(Pyrenophora teres)及びコクリオボルス・サチブス(Cochliobolus sativus))、裸黒穂病(ウスチラゴ・ヌダ(Ustilago nuda))並びにフザリウム(fusaria)(ミクロドキウム・ニバル(Microdochium nivale)及びフザリウム・ロゼウム(Fusarium roseum));
-オオムギ、植物の地上部の下記の病害の防除に関して:穀類眼紋病(タペシア・ヤルンダ(Tapesia yallundae))、網斑病(ピレノホラ・テレス(Pyrenophora teres)及びコクリオボルス・サチブス(Cochliobolus sativus))、ウドンコ病(エリシフェグラミニスフォルマスペキエホルデイ(Erysiphe graminis forma specie hordei))、小さび病(プッシニア・ホルデイ(Puccinia hordei))並びに葉枯病(リンコスポリウム・セカリス(Rhynchosporium secalis));
-ジャガイモ、塊茎の病害の防除に関して(特に、ヘルミントスポリウム・ソラニ(Helminthosporium solani)、ホマ・ツベロサ(Phoma tuberosa)、リゾクトニア・ソラニ(Rhizoctonia solani)、フザリウム・ソラニ((Fusarium solani))、ウドンコ病(プルリトプトラ・インフェスタンス(Plrytopthora infestans))並びに特定のウイルス(ウイルスY);
-ジャガイモ、下記の葉の病害の防除に関して:夏疫病(アルテルナリア・ソラニ(Alternaria solani))、ウドンコ病(フィトフトラ・インフェスタンス(Phytophthora infestans));
-ワタ、種子から成長させた若い植物の下記の病害の防除に関して:立枯れ病及び輪紋病(リゾクトニア・ソラニ(Rhizoctonia solani)、フザリウム・オキシスポラム(Fusarium oxysporum))並びに黒根病(チエラビオプシス・バシコラ(Thielaviopsis basicola));
-タンパク質産生植物、例えば、エンドウマメ、下記の種子病害の防除に関して:炭疽病(アスコキタ・ピシ(Ascochyta pisi)、ミコスファエレラ・ピノデス(Mycosphaerella pinodes))、フザリウム(fusaria)(フザリウム・オキシスポラム(Fusarium oxysporum))、灰色かび病(ポトリティス・シネレア(Botrytis cinerea))並びにウドンコ病(ペロノスポラ・ピシ(Peronospora pisi));
-含油植物、例えば、セイヨウアブラナ、下記の種子病害の防除に関して:ホマ・リンガム(Phoma lingam)、アルテルナリア・ブラッシカ(Alternaria brassicae)及びスクレロチニア・スクレロチオルム(Sclerotinia sclerotiorum);
-トウモロコシ、種子病害の防除に関して:(リゾプス属(Rhizopus)の種、ペニシリウム属(Penicillium)の種、トリコデルマ属(Trichoderma)の種、アスペルギルス属(Aspergillus)の種、及びジベル・エラフジクロイ(Gibber ellafujikuroi));
-アマ、種子病害の防除に関して:アルテルナリア・リニコラ(Alternaria linicola);
-森林樹、立枯れ病の防除に関して(フザリウム・オキシスポラム(Fusarium oxysporum)、リゾクトニア・ソラニ(Rhizoctonia solani));
-イネ、地上部の下記の病害の防除に関して:いもち病(マグナポルト・グリセア(Magnaporthe grisea))、赤色菌核病(リゾクトニア・ソラニ(Rhizoctonia solani));
-マメ科植物、種子又は種子から成長させた若い植物の下記の病害の防除に関して:立枯れ病及び輪紋病(フザリウム・オキシスポラム(Fusarium oxysporum)、フザリウム・ロゼウム(Fusarium roseum)、リゾクトニア・ソラニ(Rhizoctonia solani)、フィチウム属(Pythium)の種);
-マメ科植物、地上部の下記の病害の防除に関して:灰色かび病(ボトリチス属(Botrytis)の種)、ウドンコ病(特に、エリシフ・シコラセアルム(Erysiphe cichoracearum)、スファエロテカ・フリギネア(Sphaerotheca fuliginea)及びレベイルラ・タウリカ(Leveillula taurica))、フザリウム(fusaria)(フザリウム・オキシスポラム(Fusarium oxysporum)、フザリウム・ロゼウム(Fusarium roseum))、斑点病(クラドスポリウム属(Cladosporium)の種)、アルテルナリア斑点病(アルテルナリア属(Alternaria)の種)、炭疽病(コレトトリクム属(Colletotrichum)の種)、セプトリア斑点病(セプトリア属(Septoria)の種)、ブラックスペック(リゾクトニア・ソラニ(Rhizoctonia solani))、ウドンコ病(例えば、ブレミア・ラクツカ(Bremia lactucae)、ペロノスポラ属(Peronospora)の種、プソイドペロノスポラ属(Pseudoperonospora)の種、フィトフトラ属(Phytophthora)の種);
-果樹、地上部の病害に関して:モニリア病(モニリア・フルクチゲナ(Monilia fructigenae)、モニリア・ラキサ(M.laxa))、瘡痂病(ベンツリア・イナエクアリス(Venturia inaequalis))、ウドンコ病(ポドスファエラ・ロイコトリカ(Podosphaera leucotricha));-つる植物、葉の病害に関して:特に、灰色かび病(ボトリチス・シネレア(Botrytis cinerea))、ウドンコ病(ウンシヌラ・ネカトル(Uncinula necator))、黒腐れ病(グイグナルジア・ビウェリ(Guignardia biwelli))並びにウドンコ病(プラスモパラ・ビチコラ(Plasmopara viticola));
-ビートの根、地上部の下記の病害に関して:セルコスポラ葉枯病(セルコスポラ・ベチコラ(Cercospora beticola))、ウドンコ病(エリシフ・ベチコラ(Erysiphe beticola))、斑点病(ラムラリア・ベチコラ(Ramularia beticola))
について記述し得る。
乳化性濃縮物:
有効成分:1~95%、好ましくは60~90%
表面活性剤:1~30%、好ましくは5~20%
液体担体:1~80%、好ましくは1~35%
有効成分:0.1~10%、好ましくは0.1~5%
固体担体:99.9~90%、好ましくは99.9~99%
有効成分:5~75%、好ましくは10~50%
水:94~24%、好ましくは88~30%
表面活性剤:1~40%、好ましくは2~30%
有効成分:0.5~90%、好ましくは1~80%
表面活性剤:0.5~20%、好ましくは1~15%
固体担体:5~95%、好ましくは15~90%
有効成分:0.1~30%、好ましくは0.1~15%
固体担体:99.5~70%、好ましくは97~85%
I+ジアリホス、I+ジアミダホス、I+ジアジノン、I+ジカプトン、I+ジクロフェンチオン、I+ジクロルボス、I+ジクリホス、I+ジクレシル、I+ジクロトホス、I+ジシクラニル、I+ジエルドリン、I+ジエチル5-メチルピラゾール-3-イルホスフェート、I+ジフルベンズロン、I+ジロール、I+ジメフルトリン、I+ジメホックス、I+ジメタン、I+ジメトエート、I+ジメトリン、I+ジメチルビンホス、I+ジメチラン、I+ジネクス、I+ジネクス-ジクレキシン、I+ジノプロプ、I+ジノサム、I+ジノセブ、I+ジノテフラン、I+ジオフェノラン、I+ジオキサベンゾホス、I+ジオキサカルブ、I+ジオキサチオン、I+ジスルホトン、I+ジチクロホス、I+DNOC、I+ドラメクチン、I+DSP、I+エクジステロン、I+EI 1642、I+エマメクチン、I+エマメクチン安息香酸塩、I+EMPC、I+エンペントリン、I+エンドスルファン、I+エンドチオン、I+エンドリン、I+EPBP、I+EPN、I+エポフェノナン、I+エプリノメクチン、I+エスフェンバレレート、I+エタホス、I+エチオフェンカルブ、I+エチオン、I+エチプロール、I+エトエート-メチル、I+エトプロホス、I+ギ酸エチル、I+エチル-DDD、I+二臭化エチレン、I+二塩化エチレン、I+エチレンオキシド、I+エトフェンプロックス、I+エトリムホス、I+EXD、I+ファンファー、I+フェナミホス、I+フェナザフロル、I+フェンクロルホス、I+フェネタカルブ、I+フェンフルトリン、I+フェニトロチオン、I+フェノブカルブ、I+フェノキサクリム、I+フェノキシカルブ、I+フェンピリトリン、I+フェンプロパトリン、I+フェンピラド、I+フェンスルホチオン、I+フェンチオン、I+フェンチオン-エチル、I+フェンバレレート、I+フィプロニル、I+フロニカミド、I+フルベンジアミド、I+フルコフロン、I+フルシクロクスロン、I+フルシトリネート、I+フルエネチル、I+フルフェネリム、I+フルフェノクスロン、I+フルフェンプロックス、I+フルメトリン、I+フルバリネート、I+FMC 1137、I+ホノホス、I+ホルメタネート、I+塩酸ホルメタネート、I+ホルモチオン、I+ホルムパラネート、I+ホスメチラン、I+ホスピレート、I+ホスチアゼート、I+ホスチエタン、I+フラチオカルブ、I+フレトリン、I+γ-シハロトリン、I+γ-HCH、I+グアザチン、I+酢酸グアザチン、I+GY-81、I+ハルフェンプロックス、I+ハロフェノジド、I+HCH、I+HEOD、I+ヘプタクロル、I+ヘプテノホス、I+ヘテロホス、I+ヘキサフルムロン、I+HHDN、I+ヒドラメチルノン、I+シアン化水素、I+ハイドロプレン、I+ヒキンカルブ、I+イミダクロプリド、I+イミプロトリン、I+インドキサカルブ、I+ヨードメタン、I+IPSP、I+イサゾホス、I+イソベンザン、I+イソカルボホス、I+イソドリン、I+イソフェンホス、I+イソラン、I+イソプロカルブ、I+イソプロピルO-(メトキシアミノチオホスホリル)サリチレート、I+イソプロチオラン、I+イソチオエート、I+イソキサチオン、I+イベルメクチン、I+ジャスモリンI、I+ジャスモリンII、I+ヨードフェンホス、I+幼若ホルモンI、I+幼若ホルモンII、I+幼若ホルモンIII、I+ケレバン、I+キノプレン、I+λ-シハロトリン、I+ヒ酸鉛、I+レピメクチン、I+レプトホス、I+リンダン、I+リリムホス、I+ルフェヌロン、I+リチダチオン、I+m-クメニルメチルカルバメート、I+リン化マグネシウム、I+マラチオン、I+マロノベン、I+マジドックス、I+メカルバム、I+メカルフォン、I+メナゾン、I+メホスホラン、I+塩化第一水銀、I+メスルフェンホス、I+メタフルミゾン、I+メタム、I+メタム-カリウム、I+メタム-ナトリウム、I+メタクリホス、I+メタミドホス、I+フッ化メタンスルホニル、I+メチダチオン、I+メチオカルブ、I+メトクロトホス、I+メトミル、I+メトプレン、I+メトキン-ブチル、I+メトトリン、I+メトキシクロル、I+メトキシフェノジド、I+臭化メチル、I+メチルイソチオシアネート、I+メチルクロロホルム、I+塩化メチレン、I+メトフルトリン、I+メトルカルブ、I+メトキサジアゾン、I+メビンホス、I+メキサカルベート、I+ミルベメクチン、I+ミルベマイシンオキシム、I+ミパホックス、I+ミレックス、I+モノクロトホス、I+モルホチオン、I+モキシデクチン、I+ナフタロホス、I+ナレド、I+ナフタレン、I+NC-170、I+NC-184、I+ニコチン、I+硫酸ニコチン、I+ニフルリジド、I+ニテンピラム、I+ニチアジン、I+ニトリラカルブ、I+ニトリラカルブ1:1塩化亜鉛錯体、I+NNI-0101、I+NNI-0250、I+ノルニコチン、I+ノバルロン、I+ノビフルムロン、I+O-5-ジクロロ-4-ヨードフェニルO-エチルエチルホスホノチオエート、I+O,O-ジエチルO-4-メチル-2-オキソ-2H-クロメン-7-イルホスホロチオエート、I+O,O-ジエチルO-6-メチル-2-プロピルピリミジン-4-イルホスホロチオエート、I+O,O,O’,O’-テトラプロピルジチオピロホスフェート、I+オレイン酸、I+オメトエート、I+オキサミル、I+オキシデメトン-メチル、I+オキシデプロホス、I+オキシジスルホトン、I+pp’-DDT、I+パラ-ジクロロベンゼン、I+パラチオン、I+パラチオン-メチル、I+ペンフルロン、I+ペンタクロロフェノール、I+ラウリン酸ペンタクロロフェニル、I+ペルメトリン、I+石油、I+PH 60-38、I+フェンカプトン、I+フェノトリン、I+フェントエート、I+ホレート+TX、I+ホサロン、I+ホスホラン、I+ホスメット、I+ホスニクロール、I+ホスファミドン、I+ホスフィン、I+ホキシム、I+ホキシム-メチル、I+ピリメタホス、I+ピリミカルブ、I+ピリミホス-エチル、I+ピリミホス-メチル、I+ポリクロロジシクロペンタジエン異性体、I+ポリクロロテルペン、I+亜ヒ酸カリウム、I+カリウムチオシアネート、I+プラレトリン、I+プレコセンI、I+プレコセンII、I+プレコセンIII、I+プリミドホス、I+プロフェノホス、I+プロフルトリン、I+プロマシル、I+プロメカルブ、I+プロパホス、I+プロペタンホス、I+プロポクサー、I+プロチダチオン、I+プロチオホス、I+プロトエート、I+プロトリフェンビュート、I+ピメトロジン、I+ピラクロホス、I+ピラゾホス、I+ピレスメトリン、I+ピレトリンI、I+ピレトリンII、I+ピレトリン、I+ピリダベン、I+ピリダリル、I+ピリダフェンチオン、I+ピリミジフェン、I+ピリミテート、I+ピリプロキシフェン、I+クアッシア、I+キナルホス、I+キナルホス-メチル、I+キノチオン、I+キンチオキス、I+R-1492、I+ラフォキサニド、I+レスメトリン、I+ロテノン、I+RU 15525、I+RU 25475、I+リアニア、I+リアノジン、I+サバジラ、I+シュラーダン、I+セブホス、I+セラメクチン、I+SI-0009、I+SI-0205、I+SI-0404、I+SI-0405、I+シラフルオフェン、I+SN 72129、I+亜ヒ酸ナトリウム、I+シアン化ナトリウム、I+フッ化ナトリウム、I+ヘキサフルオロケイ酸ナトリウム、I+ナトリウムペンタクロロフェノキシド、I+セレン酸ナトリウム、I+ナトリウムチオシアネート、I+ソファミド、I+スピノサド、I+スピロメシフェン、I+スピロテトラマト、I+スルコフロン、I+スルコフロン-ナトリウム、I+スルフルアミド、I+スルホテップ、I+フッ化スルフリル、I+スルプロホス、I+タール油、I+τ-フルバリネート、I+タジムカルブ、I+TDE、I+テブフェノジド、I+テブフェンピラド、I+テブピリムホス、I+テフルベンズロン、I+テフルトリン、I+テメホス、I+TEPP、I+テラレトリン、I+テルバム、I+テルブホス、I+テトラクロロエタン、I+テトラクロルビンホス、I+テトラメトリン、I+θ-シペルメトリン、I+チアクロプリド、I+チアフェノックス、I+チアメトキサム、I+チクロホス、I+チオカルボキシム、I+チオシクラム、I+チオシクラムシュウ酸水素塩、I+チオジカルブ、I+チオファノックス、I+チオメトン、I+チオナジン、I+チオスルタップ、I+チオスルタップ-ナトリウム、I+ツリンギエンシン、I+トルフェンピラド、I+トラロメトリン、I+トランスフルトリン、I+トランスペルメトリン、I+トリアミホス、I+トリアザメート、I+トリアゾホス、I+トリアズロン、I+トリクロルホン、I+トリクロルメタホス-3、I+トリクロロナート、I+トリフェノホス、I+トリフルムロン、I+トリメタカルブ、I+トリプレン、I+バミドチオン、I+バニリプロール、I+ベラトリジン、I+ベラトリン、I+XMC、I+キシリルカルブ、I+YI-5302、I+ζ-シペルメトリン、I+ゼータメトリン(zetamethrin)、I+リン化亜鉛、I+ゾラプロホス及びZXI 8901、I+シアントラニリプロール、I+クロラントラニリプロール、I+シエノピラフェン、I+シフルメトフェン、I+ピリフルキナゾン、I+スピネトラム、I+スピロテトラマト、I+スルホキサフロール、I+フルフィプロール、I+メペルフルトリン、I+テトラメチルフルトリン、I+トリフルメゾピリムが挙げられる。
1.1 形態A
形態Aを調製するための方法は、国際公開第2015/003951号(実施例P5)に開示されている。形態Aを調製するための一例は、下記の通りである。
FT-IR3282、3077、2981、2952、1650、1593、1543、1473、1353、1187、1138、1074、1066、1054cm-1
形態Aを、HPLCバイアル中で10%水/メタノールに溶解した。溶媒を室温にて蒸発させた。
0.02gの形態AをHPLCバイアル中で秤量し、0.3mlの50%水/メタノールを加えた。試料を25℃にて1週間撹拌し、形態Bの結晶を得た。
N-[(1S,2S)-2-(2,4-ジクロロフェニル)シクロブチル]-2-(トリフルオロメチル)ピリジン-3-カルボキサミドの形態A(80g)を、Ti=55℃(槽内のTi=温度)にてアセトン(240g、4.1mol)及び水(80g、4.4mol)の混合物に溶解した。次いで、混合物をTi=8℃へと冷却し、種結晶をTi=29℃にて加えた。反応混合物が8℃の温度に達すると、水(86g、4.8mol)を60分に亘り反応混合物に加えた。さらなる一定分量の水(174g、9.7mol)を1時間に亘り加えた後、反応混合物を30分間撹拌した。それに続き、最終の一定分量の水(340g、18.9mol)を加え、懸濁液を80分間撹拌した。懸濁液を濾過し、濾過ケークを水(2×80g、4.)で洗浄し、その後、これを減圧下で35℃にて乾燥させ、N-[(1S,2S)-2-(2,4-ジクロロフェニル)シクロブチル]-2-(トリフルオロメチル)ピリジン-3-カルボキサミド(94.6g)の一水和物を得た。
1H NMR(400MHz,CDCl3)δ 8.65(dd,J=4.6Hz,J=1.2Hz,1H),7.60-7.58(m,1H),7.47-7.44(m,1H),7.41-7.40(m,1H),7.33-7.25(m,2H),5.54(br d,J=7.8Hz,1H),5.03(五重項,J=7.3Hz,1H),4.24(q,J=7.8Hz,1H),2.65-2.56(m,1H),2.44-2.28(m,2H),2.10-2.01(m,1H).
FT-IR 3403,3232,3079,2948,1660,1645,1593,1575,1471,1326,1186,1126,1076,1054 cm-1.
Cis-N-[2-(2,4-ジクロロフェニル)シクロブチル]-2-(トリフルオロメチル)ピリジン-3-カルボキサミドラセミ化合物(調製方法は、国際公開第2013/143811号に開示されている)を、バイアル中で一次溶媒(メタノール、アセトン又はアセトニトリル)に溶解し、水を加えて、化合物を沈殿させた。次いで、懸濁液を10~50℃にて温度サイクルにかけ、室温に冷却し(自然冷却)、48時間静置し、その後、結晶を得た。
2つのエナンチオマーであるN-[(1S,2S)-2-(2,4-ジクロロフェニル)シクロブチル]-2-(トリフルオロメチル)ピリジン-3-カルボキサミド及びN-[(1R,2R)-2-(2,4-ジクロロフェニル)シクロブチル]-2-(トリフルオロメチル)ピリジン-3-カルボキサミドのラセミ化合物であるCis-N-[2-(2,4-ジクロロフェニル)シクロブチル]-2-(トリフルオロメチル)ピリジン-3-カルボキサミドは、国際公開第2013/143811号に記載されているように調製することができ、ここで、cis-N-[2-(2,4-ジクロロフェニル)シクロブチル]-2-(トリフルオロメチル)ピリジン-3-カルボキサミドは、表57、実施例57.011において例示されている。
2.1 実験条件:
粉末X線回折分析(pXRD):
固体材料の粉末X線回折分析を、室温及び40%超の相対湿度にてBruker D8粉末回折計を使用して行った。試料をPerspex試料保持器中に乗せ、試料を平坦化した。試料保持器を回転させ、25~30分のスキャン時間を伴って、パターン強度によって4°から34°の2シータでX線を収集した。多形形態A、B及びCについての測定した粉末X線回折パターンを、それぞれ、図2、5及び8において示す。
形態A:単結晶強度データを、Cu Kα照射(λ=1.5418Å)を使用して黒鉛モノクロメーターを備えたOxford Xcalibar PX Ultra回折計上で収集した。結晶を、データ収集のために100KにてNVH油中で乗せた。CRYSTALSソフトウェアパッケージを使用してデータを解析した。このデータを使用して、多形形態Aについての予測した粉末X線回折パターンを生じさせた(図1)。
Mettler Toledo DSC1を使用して、DSCを行った。概ね5mgの試料充填を使用し、これを10℃/分の速度で25℃から250℃へと加熱した。DSCるつぼの蓋に穴を開け、試料の加熱の間に形成される気体が漏れることを可能とした。
a)pXRD
形態Aの粉末X線回折パターンを、図2に示す。
a)pXRD
形態BのX線粉末回折パターンを、図5に示す。
結晶形態(形態B)の融解ピークは、約65℃にてDSCトレースにおいて広範な水吸熱反応である。
a)X線粉末回折
形態CのX線粉末回折パターンを、図5に示す。
結晶形態(形態C)の融解ピークは、約85℃にてDSCトレースにおいて広範な水吸熱反応である。
a)X線粉末回折
形態DのX線粉末回折パターンを、図10に示す。
DSCトレースにおける結晶形態(形態D)の融解ピークは、約157℃におけるものである。
多形形態A及びBを含む製剤は、同じ処方を使用して種子処理FS200のためにフロアブル濃縮物として製剤化した。使用した処方を、表8において示す。
本発明のまた別の態様は、以下のとおりであってもよい。
〔1〕21~26℃の温度にて6.1±0.2、11.2±0.2、14.0±0.2、16.7±0.2、17.2±0.2、18.5±0.2、20.8±0.2、21.3±0.2、22.3±0.2、23.6±0.2、23.9±0.2及び24.5±0.2の群から選択される4以上の2シータ角度値を含むX線粉末回折パターンによって特性決定される、式(I)
〔2〕21~26℃の温度にて6.1±0.2、11.2±0.2、14.0±0.2、16.7±0.2、17.2±0.2、18.5±0.2、20.8±0.2、21.3±0.2、22.3±0.2、23.6±0.2、23.9±0.2及び24.5±0.2の群から選択される6以上の2シータ角度値を含むX線粉末回折パターンによって特性決定される、前記〔1〕に記載の結晶形態。
〔3〕前記X線粉末回折パターンが、21~26℃の温度にて図5に示すX線粉末回折スペクトルと実質的に同じである、前記〔1〕又は〔2〕に記載の結晶形態。
〔4〕下記の単位格子パラメーター:
a=15.52ű0.01Å、b=7.24ű0.01Å、c=16.64ű0.01Å、α=90°±0.01°、β=105.03±0.01°、γ=90°±0.01°、Z=4によって特性決定される、前記〔1〕~〔3〕のいずれか一項に記載の結晶形態。
〔5〕融解ピークが、約65℃におけるものである、前記〔1〕~〔3〕のいずれか一項に記載の結晶形態。
〔6〕21~26℃の温度にて10.8±0.2、14.5±0.2、17.5±0.2、19.0±0.2、23.5±0.2、24.5±0.2、26.0±0.2、30.2±0.2、32.6±0.2、33.3±0.2、34.1±0.2及び35.5±0.2の群から選択される4以上の2シータ角度値を含むX線粉末回折パターンによって特性決定される、式(I)
〔7〕21~26℃の温度にて10.8±0.2、14.5±0.2、17.5±0.2、19.0±0.2、23.5±0.2、24.5±0.2、26.0±0.2、30.2±0.2、32.6±0.2、33.3±0.2、34.1±0.2及び35.5±0.2の群から選択される6以上の2シータ角度値を含むX線粉末回折パターンによって特性決定される、前記〔6〕に記載の結晶形態。
〔8〕前記X線粉末回折パターンが、21~26℃の温度にて図8に示すX線粉末回折スペクトルと実質的に同じである、前記〔6〕又は〔7〕に記載の結晶形態。
〔9〕融解ピークが、約85℃におけるものである、前記〔6〕~〔8〕のいずれか一項に記載の結晶形態。
〔10〕下記の単位格子パラメーター:
a=7.27ű0.01Å、b=9.32ű0.01Å、c=14.11ű0.01Å、α=75.53°±0.01°、β=87.03±0.01°、γ=71.48°±0.01°、Z=2によって特性決定される、前記〔6〕~〔9〕のいずれか一項に記載の結晶形態。
〔11〕前記〔1〕~〔10〕のいずれか一項に記載の結晶形態及び少なくとも1種の許容される担体又は賦形剤を含む、農業組成物又は医薬組成物。
〔12〕1種の殺虫、殺ダニ、殺線虫又は殺真菌活性剤をさらに含む、前記〔11〕に記載の組成物。
〔13〕線虫有害生物又は真菌によってもたらされる損傷に対する有用な植物の保護において使用するための、前記〔1〕~〔10〕のいずれか一項に記載の結晶形態。
〔14〕線虫有害生物によってもたらされる損傷に対して、有用な植物の作物を保護する方法であって、前記植物又はその生息地を、前記〔11〕又は〔12〕に記載の組成物で処理することを含む、方法。
〔15〕線虫有害生物によってもたらされる損傷に対して植物繁殖材料を保護する方法であって、この材料を、前記〔11〕又は〔12〕に記載の組成物で処理することを含む、方法。
Claims (11)
- 21~26℃の温度にて6.1±0.2、11.2±0.2、14.0±0.2、16.7±0.2、17.2±0.2、18.5±0.2、20.8±0.2、21.3±0.2、22.3±0.2、23.6±0.2、23.9±0.2及び24.5±0.2の群から選択される6以上の2シータ角度値を含むX線粉末回折パターンによって特性決定される、請求項1に記載の結晶。
- 下記の単位格子パラメーター:
a=15.52ű0.01Å、b=7.24ű0.01Å、c=16.64ű0.01Å、α=90°±0.01°、β=105.03±0.01°、γ=90°±0.01°、Z=4によって特性決定される、請求項1又は2に記載の結晶。 - 融解ピークが、約65℃におけるものである、請求項1~3のいずれか一項に記載の結晶。
- 請求項1~4のいずれか一項に記載の結晶及び少なくとも1種の許容される担体又は賦形剤を含む、農業組成物。
- 少なくとも1種の殺虫、殺ダニ、殺線虫又は殺真菌活性剤をさらに含む、請求項5に記載の組成物。
- 線虫有害生物又は真菌によってもたらされる損傷から有用な植物を保護するための、請求項1~4のいずれか一項に記載の結晶の使用。
- 線虫有害生物によってもたらされる損傷に対して、有用な植物の作物を保護する方法であって、前記植物又はその生息地を、請求項5又は6に記載の組成物で処理することを含む、方法。
- 線虫有害生物によってもたらされる損傷に対して植物繁殖材料を保護する方法であって、この材料を、請求項5又は6に記載の組成物で処理することを含む、方法。
- 真菌によってもたらされる損傷に対して、有用な植物の作物を保護する方法であって、前記植物又はその生息地を、請求項5又は6に記載の組成物で処理することを含む、方法。
- 真菌によってもたらされる損傷に対して植物繁殖材料を保護する方法であって、この材料を、請求項5又は6に記載の組成物で処理することを含む、方法。
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