JP2017508778A - 殺虫性および殺線虫性を有する活性成分組み合わせ物 - Google Patents
殺虫性および殺線虫性を有する活性成分組み合わせ物 Download PDFInfo
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- JP2017508778A JP2017508778A JP2016559281A JP2016559281A JP2017508778A JP 2017508778 A JP2017508778 A JP 2017508778A JP 2016559281 A JP2016559281 A JP 2016559281A JP 2016559281 A JP2016559281 A JP 2016559281A JP 2017508778 A JP2017508778 A JP 2017508778A
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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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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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
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- A—HUMAN NECESSITIES
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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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
- A01N43/90—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
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
AはA−1.0またはA−2.0であり、ここで点線はQのN原子への結合を表しており;
QはQ−1.0またはQ−2.0であり、ここで、窒素は環Aに結合しており、矢印はいずれの場合にもNHCO部分への結合を表しており;
WはW1〜W11:
テトラメチルフルトリン(tetramethylfluthrin)、テトラニリプロール(tetraniliprole)、テトラクロラントラニリプロール(tetrachlorantraniliprole)、トリフルメゾピリム(triflumezopyrim)およびヨードメタン、チオキサザフェン(tioxazafen)およびジメチル−ジスルフィド、チモール、ハルピン(harpin)並びに以下の活性化合物:1−{2−フルオロ−4−メチル−5−[(2,2,2−トリフルオロエチル)スルフィニル]フェニル}−3−(トリフルオロメチル)−1H−1,2,4−トリアゾール−5−アミン(WO2006/043635から公知)、{1’−[(2E)−3−(4−クロロフェニル)プロパ−2−エン−1−イル]−5−フルオロスピロ[インドール−3,4’
−ピペリジン]−1(2H)−イル}(2−クロロピリジン−4−イル)メタノン(WO2003/106457から公知)、2−クロロ−N−[2−{1−[(2E)−3−(4−クロロフェニル)プロパ−2−エン−1−イル]ピペリジン−4−イル}−4−(トリフルオロメチル)フェニル]イソニコチンアミド(WO2006/003494から公知)、3−(2,5−ジメチルフェニル)−4−ヒドロキシ−8−メトキシ−1,8−ジアザスピロ[4.5]デカ−3−エン−2−オン(WO2009/049851から公知)、3−(2,5−ジメチルフェニル)−8−メトキシ−2−オキソ−1,8−ジアザスピロ[4.5]デカ−3−エン−4−イル−エチルカルボネート(WO2009/049851から公知)、4−(ブタ−2−イン−1−イルオキシ)−6−(3,5−ジメチルピペリジン−1−イル)−5−フルオロピリミジン(WO2004/099160から公知)、4−(ブタ−2−イン−1−イルオキシ)−6−(3−クロロフェニル)ピリミジン(WO2003/076415から公知)、PF1364(CAS登録番号1204776−60−2)、メチル2−[2−({[3−ブロモ−1−(3−クロロピリジン−2−イル)−1H−ピラゾール−5−イル]カルボニル}アミノ)−5−クロロ−3−メチルベンゾイル]−2−メチルヒドラジンカルボキシレート(WO2005/085216から公知)、メチル2−[2−({[3−ブロモ−1−(3−クロロピリジン−2−イル)−1H−ピラゾール−5−イル]カルボニル}アミノ)−5−シアノ−3−メチルベンゾイル]−2−エチルヒドラジンカルボキシレート(WO2005/085216から公知)、メチル2−[2−({[3−ブロモ−1−(3−クロロピリジン−2−イル)−1H−ピラゾール−5−イル]カルボニル}アミノ)−5−シアノ−3−メチルベンゾイル]−2−メチルヒドラジンカルボキシレート(WO2005/085216から公知)、
メチル2−[3,5−ジブロモ−2−({[3−ブロモ−1−(3−クロロピリジン−2−イル)−1H−ピラゾール−5−イル]カルボニル}アミノ)ベンゾイル]−2−エチルヒドラジンカルボキシレート(WO2005/085216から公知)、N−[2−(5−アミノ−1,3,4−チアジアゾール−2−イル)−4−クロロ−6−メチルフェニル]−3−ブロモ−1−(3−クロロピリジン−2−イル)−1H−ピラゾール−5−カルボキサミド(CN102057925から公知)、8−クロロ−N−[(2−クロロ−5−メトキシフェニル)スルホニル]−6−(トリフルオロメチル)イミダゾ[1,2−a]ピリジン−2−カルボキサミド(WO2010/129500から公知)、4−[5−(3,5−ジクロロフェニル)−5−(トリフルオロメチル)−4,5−ジヒドロ−1,2−オキサゾール−3−イル]−2−メチル−N−(1−オキシドチエタン−3−イル)ベンズアミド(WO2009/080250から公知)、N−[(2E)−1−[(6−クロロピリジン−3−イル)メチル]ピリジン−2(1H)−イリデン]−2,2,2−トリフルオロアセトアミド(WO2012/029672から公知)、1−[(2−クロロ−1,3−チアゾール−5−イル)メチル]−4−オキソ−3−フェニル−4H−ピリド[1,2−a]ピリミジン−1−イウム−2−オレート(WO2009/099929から公知)、1−[(6−クロロピリジン−3−イル)メチル]−4−オキソ−3−フェニル−4H−ピリド[1,2−a]ピリミジン−1−イウム−2−オレート(WO2009/099929から公知)、4−(3−{2,6−ジクロロ−4−[(3,3−ジクロロプロパ−2−エン−1−イル)オキシ]フェノキシ}プロポキシ)−2−メトキシ−
6−(トリフルオロメチル)ピリミジン(CN101337940から公知)、N−[2−(tert−ブチルカルバモイル)−4−クロロ−6−メチルフェニル]−1−(3−クロロピリジン−2−イル)−3−(フルオロメトキシ)−1H−ピラゾール−5−カルボキサミド(WO2008/134969から公知 、3−[ベンゾイル(メチル)アミノ]−N−[2−ブロモ−4−[1,2,2,2−テトラフルオロ−1−(トリフルオロメチル)エチル]−6−(トリフルオロメチル)フェニル]−2−フルオロ−ベンズアミド(WO2010018714から公知)、ブチル[2−(2,4−ジクロロフェニル)−3−オキソ−4−オキサスピロ[4.5]デカ−1−エン−1−イル]カルボネート(CN102060818から公知)、4−[5−(3,5−ジクロロフェニル)−5−(トリフルオロメチル)−4H−イソキサゾール−3−イル]−N−[(Z)−メトキシイミノメチル]−2−メチル−ベンズアミド(WO2007/026965から公知)、3E)−3−[1−[(6−クロロ−3−ピリジル)メチル]−2−ピリジリデン]−1,1,1−トリフルオロ−プロパン−2−オン(WO2013/144213から公知)、
N−(メチルスルホニル)−6−[2−(ピリジン−3−イル)−1,3−チアゾール−5−イル]ピリジン−2−カルボキサミド(WO2012/000896から公知)、N−[3−(ベンジルカルバモイル)−4−クロロフェニル]−1−メチル−3−(ペンタフルオロエチル)−4−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミド(WO2010/051926から公知)。
アグロバクテリウム・ラジオバクター(Agrobacterium radiobacter)、バチルス・アキドカルダリウス(Bacillus acidocaldarius)、バチルス・アキドテレストリス(Bacillus acidoterrestris)、バチルス・アグリ(Bacillus agri)、バチルス・アイザワイ(Bacillus aizawai)、バチルス・アルボラクティス(Bacillus albolactis)、バチルス・アルカロピルス(Bacillus alcalophilus)、バチルス・アルベイ(Bacillus alvei)、バチルス・アミノグルコシディクス(Bacillus aminoglucosidicus)、バチルス・アミノボランス(Bacillus aminovorans)、バチルス・アミロリティクス(Bacillus amylolyticus)(パエニバチルス・アミロリティクス(Paenibacillus amylolyticus)としても知られている)、特に、バチルス・アミロリケファシエンス(Bacillus amyloliquefaciens)、特に、IN937a株、またはFZB42株(DSM231179)(RhizoVitalとして知られる製品、ABiTEP社製、ドイツ)、またはB3株、バチルス・アネウリノリティクス(Bacillus aneurinolyticus)、バチルス・アトロパエウス(Bacillus atrophaeus)、バチルス・アゾトフォルマンス(Bacillus azotoformans)、バチルス・バディウス(Bacillus badius)、またはセレウス菌(Bacillus cereus)(同義:
バチルス・エンドリトモス(Bacillus endorhythmos)、バチルス・メドゥサ(Bacillus medusa))、特に、セレウス菌(B. cereus)CNCMI−1562株の胞子(US6,406,690を参照)、バチルス・キチノスポルス(Bacillus chitinosporus)、バチルス・サークランス(Bacillus circulans)、バチルス・コアグランス(Bacillus coagulans)、バチルス・エンドパラシティクス(Bacillus endoparasiticus)、バチルス・ファスティディオスス(Bacillus fastidiosus)、またはバチルス・フィルムス(Bacillus firmus)、特に、I−1582株(Bionem、FlocterまたはVOTIVOとして知られる製品、バイエル・クロップサイエンス社(Bayer CropScience)製)、バチルス・クルスタキ(Bacillus kurstaki)、バチルス・ラクティコラ(Bacillus lacticola)、バチルス・ラクティモルブス(Bacillus lactimorbus)、バチルス・ラクティス(Bacillus lactis)、バチルス・ラテロスポルス(Bacillus laterosporus)(ブレビバチルス・ラテロスポルス(Brevibacillus laterosporus)としても知られている)、バチルス・ラウツス(Bacillus lautus)、バチルス・レンティモルブス(Bacillus lentimorbus)、バチルス・レンツス(Bacillus lentus)、リケニホルミス菌(Bacillus licheniformis)、バチルス・マロカヌス(Bacillus maroccanus)、巨大菌(Bacillus megaterium)(BioArcとして知られる製品)、バチルス・メティエンス(Bacillus metiens)、根状菌分離菌J(Bacillus mycoides isolate J)、なっとう菌(Bacillus natto)、
バチルス・ネマトキダ(Bacillus nematocida)、バチルス・ニグリフィカンス(Bacillus nigrificans)、バチルス・ニグルム(Bacillus nigrum)、バチルス・パントテンティクス(Bacillus pantothenticus)、バチルス・ポピラエ(Bacillus popillae)(Cronoxとして知られる製品)、バチルス・サイクロサッカロリティクス(Bacillus psychrosaccharolyticus)、またはバチルス・プミル(Bacillus pumilus)、特に、GB34株(受入番号ATCC700814)、(Yield Shieldとして知られる製品、バイエル・クロップ・サイエンス社(Bayer Crop Science)(ドイツ)製)、およびQST2808株(受入番号NRRL B−30087)、(Sonata QST 2808として知られる製品、アグラクエスト社(AgraQuest)製、米国)、またはバチルス・シアメンシス(Bacillus siamensis)、バチルス・スミティ(Bacillus smithii)、バチルス・スファエリクス(Bacillus sphaericus)(VectoLexsとして知られる製品)、枯草菌(Bacillus subtilis)、特に、GB03株(受入番号ATCC SD−1397)、(Kodiakとして知られる製品、バイエル・クロップ・サイエンス社(Bayer Crop Science)(ドイツ)製)、およびQST713/AQ713株(受入番号NRRL B−21661)、(Serenade QST 713、Serenade SoilおよびSerenade Maxとして知られる製品、アグラクエスト社(AgraQuest)製、米国)、またはQST30002/AQ30002株(受入番号NRRL B−50421、WO2012/087980を参照)、またはQST30004/AQ30004株(受入番号NRRL B−50455、WO2012/087980を参照
)、または枯草菌変種アミロリクエファキエンス(B. subtilis var. amyloliquefaciens)FZB24株(Taegroとして知られる製品)、バチルス・チューリンゲンシス(Bacillus thuringiensis)、特に、バチルス・スリンジェンシス亜種イスラエレンシス(B. thuringiensis subspecies israelensis)(血清型H−14)、AM65−52株(受入番号ATCC1276)、(VectoBacとして知られる製品、バレント・バイオサイエンス社(Valent BioSciences)製、米国)、またはバチルス・スリンジェンシス亜種アイザワイ(B. thuringiensis subsp. aizawai)、特に、ABTS−1857(SD−1372)株、(XenTariとして知られる製品、バイエル・クロップ・サイエンス社(Bayer Crop Science)(ドイツ)製)、またはバチルス・スリンジェンシス亜種クルスタキ(B. thuringiensis subsp. kurstaki)HD−1株、(Dipel ESとして知られる製品、バレント・バイオサイエンス社(Valent BioSciences)製、米国)、またはバチルス・スリンジェンシス亜種テネブリオニス(B. thuringiensis subsp. tenebrionis)NB176(SD−5428)株、(Novodor FCとして知られる製品、BioFa社製、ドイツ)、またはバチルス・スリンジェンシス変種アエギプティ(B. th. var. aegypti)(Agerinとして知られる製品)、またはバチルス・スリンジェンシス変種コルメリ(B. th. var. colmeri)(TianBaoBTcとして知られる製品)、またはバチルス・スリンジェンシス変種ダルムスタディエンシス(B. th. var. darmstadiensis)(Baciturin、Kolepterinとして知られる製品)、
またはバチルス・スリンジェンシス変種デンドロリムス(B. th. var. dendrolimus)(Dendrobacillinとして知られる製品)、またはバチルス・スリンジェンシス変種ガレリアエ(B. th. var. galleriae)((Enterobactinとして知られる製品)、またはバチルス・スリンジェンシス変種ジャポネンシス(B. th. var. japonensis)(Buihunterとして知られる製品)、またはバチルス・スリンジェンシス亜種モリソニ(B.th. subsp. Morrisoni)、またはバチルス・スリンジェンシス変種サンディエゴ(B. th. var. san diego)、またはバチルス・スリンジェンシス亜種トリンギエンシス(B. th. subsp. thuringiensis)MPPL002株、またはバチルス・スリンジェンシス変種トリンギエンシス(B. th. var. thuringiensis)(Bikolとして知られる製品)、またはバチルス・スリンジェンシス変種7216(B. th. var 7216)(Amactic、Pethianとして知られる製品)、またはバチルス・スリンジェンシス変種T36(B. th. var T36)(Cahatとして知られる製品)、またはバチルス・スリンジェンシス(B. thuringiensis)BD#32株(受入番号NRRL B−21530)(アグラクエスト社(Agraquest)製)、またはバチルス・スリンジェンシス(B. thuringiensis)AQ52株(受入番号NRRL B−21619)(アグラクエスト社(Agraquest)製)、バチルス・ウニフラゲラツス(Bacillus uniflagellatus)、ブラディリゾビウム・ジャポニクム(Bradyrhizobium japonicum)(共生生物(Symbiont)、
SoySelectとして知られる製品)、ブレビバチルス・ブレビス(Brevibacillus brevis)(以前は、短バチルス(Bacillus brevis))、特に、SS86−3株、SS86−4株、SS86−5株、2904株、ブレビバチルス・ラテロスポルス(Brevibacillus laterosporus)(以前は、バチルス・ラテロスポルス(Bacillus laterosporus))、特に、64株、1111株、1645株、1647株、クロモバクテリウム・スプトスガエ(Chromobacterium subtsugae)、特に、PRAA4−1T株(Gandevoとして知られる製品)、デルフチア・アシドボランス(Delftia acidovorans)、特に、RAY209株(BioBoostとして知られる製品)、フラボバクテリウム属(Flavobacterium)MBI−302、好酸性乳酸桿菌(Lactobacillus acidophilus)(Fruitsanとして知られる製品)、リソバクテル・アンティビオティクス(Lysobacter antibioticus)、特に、13−1株(Biological Control 2008, 45, 288-296を参照)、リソバクテル・エンジモゲネス(Lysobacter enzymogenes)、特に、C3株(J Nematol. 2006 6月; 38(2): 233−239を参照)、パエニバチルス・アルベイ(Paenibacillus alvei)
、特に、III3DT−1A株、III2E株、46C3株、2771株(バチルス属遺伝ストックセンター(Bacillus genetic stock center)、2001年11月)、パエニバチルス・ポリミクサ(Paenibacillus polymyxa)、パエニバチルス・ポピリアエ(Paenibacillus popilliae)(以前は、バチルス・ポピリアエ(Bacillus popilliae))、パントエア・アグロメランス(Pantoea agglomerans)、パスツリア・ペネトランス(Pasteuria penetrans)(以前は、バチルス・ペネトランス(Bacillus penetrans)、Pasteuria水和剤として知られる製品、パスツリア・バイオサイエンス社(Pasteuria Bioscience)製)、パスツリア・ウスガエ(Pasteuria usgae)(Econem(商標)として知られる製品、パスツリア・バイオサイエンス社(Pasteuria Bioscience)製)、パスツリア・ニシザワエ(Pasteuria nishizawae)、パスツリア属種(Pasteuria spp.)Pr3、軟腐病菌(Pectobacterium carotovorum)(以前は、軟腐病菌(Erwinia carotovora))BioKeeperとして知られる製品、緑膿菌(Pseudomonas aeruginosa)(Guiticidとして知られる製品)、シュードモナス・アウレオファキエンス(Pseudomonas aureofaciens)(Agate−25Kとして知られる製品)、シュードモナス・セパシア(Pseudomonas cepacia)(旧称:セパシア菌(Burkholderia cepacia))、特に、M54株またはJ82株、シュードモナス・クロロラピス(Pseudomonas chlororaphis)、特に、MA342株(Cedomonとして知られる製品)、蛍光菌(Pseudomonas fluorescens)(Sudozoneとして知られる製品)、シュードモナス・プロラディクス(Pseudomonas proradix)(Proradixとして知られる製品)、プチダ菌(Pseudomonas putida)(Nematsidとして知られる製品、シュードモナス・レシノボランス(Pseudomonas resinovorans)(Solanacureとして知られる製品)、シリンゲ菌(Pseudomonas syringae)(Biosaveとして知られる製品)、ロドコッカス・グロベルルス(Rhodococcus globerulus)AQ719株(受入番号NRRL B21663)(アグラクエスト社(AgraQuest)社製、米国)、セラチア・エントモピラ(Serratia entomophila)(invadeとして知られる製品)、霊菌(Serratia marcescens)、特に、SRM株(MTCC8708)またはR35株、ストレプトマイセス属種(Streptomyces sp.)NRRL B−30145株(アグラクエスト社(Agraquest)製)、
ストレプトマイセス・カンジダス(Streptomyces candidus)(BioAidTMとして知られる製品)、ストレプトマイセス・コロムビエンシス(Streptomyces colombiensis)(Mycosideとして知られる製品)、ストレプトマイセス・ガルブス(Streptomyces galbus)(=ストレプトマイセス・グリセオビリディス(Streptomyces griseoviridis))、特に、K61株(受入番号DSM7206)(Mycostopとして知られる製品、ベルデラ社(Verdera)製、Crop Protection 2006, 25, 468-475を参照)またはQST6047株(=NRRL B−30232株)(Virtuosoとして知られる製品、アグラクエスト社(Agraquest)製、米国)、ストレプトマイセス・ミクロフラブス(Streptomyces microflavus)AQ6121株(=QRD31.013、NRRL B−50550)(アグラクエスト社(Agraquest)製、米国)ストレプトマイセス・ゴシキエンシス(Streptomyces goshikiensis)(Safegroとして知られる製品)、ストレプトマイセス・グリセオビリディス(Streptomyces griseoviridis)(Mycostopとして知られる製品、カナダの微生物db(Microbial db)を参照)、ストレプトマイセス・ラベンジュレ(Streptomyces lavendulae)(Phytolavin−300として知られる製品、ストレプトマイセス・リディクス(Streptomyces lydicus)、特に、WYCD108株(ActinovateSPとして知られる製品)またはWYEC108株(Actino−ironとして知られる製品)、ストレプトマイセス・プラシヌス(Streptomyces prasinus)("Prasinons A and B: potent insecticides from Streptomyces prasinus" Applied microbiology 1973 Novを参照)、ストレプトマイセス・リモスス(Streptomyces rimosus)(Rhitovitとして知られる製品)、ストレプトマイセス・サラケティクス(Streptomyces saraceticus)(Clandaとして知られる製品)、ストレプトマイセス・ベネズエラエ(Streptomyces venezuelae)、ザントモナス・カンペストリス(Xanthomonas campestris)(除草活性)、ゼノラブダス・ルミネスケンス(Xenorhabdus luminescens)、およびゼノラブダス・ネマトフィラ(Xenorhabdus nematophila)。
アムペロミケス・クイスクアリス(Ampelomyces quisqualis)、特に、AQ10株(受入番号CNCM I−807)(AQ10として知られる製品、イントラケムバイオ社(IntrachemBio)(イタリア)製)、アウレオバシディウム・プルランス(Aureobasidium pullulans)、特に、DSM14940株の分芽胞子もしくはDSM14941株の分芽胞子またはこれらの混合物、アスケルソニア・アレイロデス(Aschersonia aleyrodes)、アスペルギルス・フラバス(Aspergillus flavus)、特に、NRRL21882株(Afla−Guardとして知られる製品、シンジェンタ社(Syngenta)製)、アルトロボトリス・スペルバ(Arthrobotrys superba)(Corda1839)、ビューベリア・バシアナ(Beauveria bassiana)、特に、ATCC74040株(Naturalisとして知られる製品、イントラケムバイオ社(Intrachem Bio)(イタリア)製)およびGHA株(Mycotrol、BotaniGardとして知られる製品、ビューベリア・ブロングニアルティ(Beauveria brongniartii)(Beauproとして知られる製品、アンダーマット・バイオコントロールAG社(Andermatt Biocontrol AG)製)、カンディダ・オレオピラ(Candida oleophila)、特に、O株(製品名Nexy、Aspire)
、)カエトミウム・クプレウム(Chaetomium cupreum)(Ketocinとして知られる製品)、クラドスポリウム・クラドスポリオイデス(Cladosporium cladosporioides)、
特に、H39株、コニディオボルス・オプスクルス(Conidiobolus obscurus)、コニオチリウム・ミニタンス(Coniothyrium minitans)、特に、CON/M/91−8株(受入番号DSM−9660)、(Contansとして知られる製品、プロフィタ社(Prophyta)(ドイツ)製)、クリプトコッカス・アルビドゥス(Cryptococcus albidus)(YieldPlusとして知られる製品、アンカー・バイオテクノロジーズ社(Anchor Bio-Technologies)製、南アフリカ共和国(ZA))、ディロポスポラ・アロペクリ(Dilophosphora alopecuri)(Twist Fungusとして知られる製品)、エントモプトラ・ビルレンタ(Entomophthora virulenta)(Vektorとして知られる製品)、フザリウム・オキシスポラム(Fusarium oxysporum)、特に、Fo47株(非病原性)(Fusacleanとして知られる製品)、グリオクラディウム・カテヌラツム(Gliocladium catenulatum)、特に、J1446株(PrestopまたはPrimastopとして知られる製品)、ヒルステラ・トムプソニイ(Hirsutella thompsonii)
(MycohitまたはABTECとして知られる製品、アグロ・バイオテック・リサーチ・センター社(Agro Bio-tech Research Centre)製 、ラゲニディウム・ギガンテウム(Lagenidium giganteum)(Laginexとして知られる製品、アグラクエスト社(AgraQuest))、レカニキリウム属種(Lecanicillium spp.)、特に、プロフィタ社(Prophyta)製のHRO LEC12株、レカニキリウム・レカニイ(Lecanicillium lecanii)(旧称:ベルチシリウム・レカニイ(Verticillium lecanii))、特に、KV01株の分生子(MycotalまたはVertalecとして知られる製品、コパート/アリスタ社(Koppert/Arysta))、レカニキリウム・ムスカリウム(Lecanicillium muscarium)(旧称:ベルチシリウム・レカニイ(Verticillium lecanii))、特に、プロフィタ社(Prophyta)製の1/1株、メタリジウム・アニソプリアエ(Metarhizium anisopliae)、特に、F52株(DSM3884/ATCC90448)(BIO1020として知られる製品、バイエル・クロップ・サイエンス・AG社(BayerCrop Science AG)、またはMet52として知られる製品、ノボザイムズ社(Novozymes))、またはメタリジウム・アニソプリアエ変種アクリドゥム(M. anisopliae var acridum)(GreenGuardまたはGreen Muscleとして知られる製品、バッカー・アンダーウッド社(Becker Underwood)、米国)、またはメタリジウム・フラボビリデ(Metarhizium flavoviride)、メトスクニコビア・フルクティコラ(Metschnikovia fructicola)、特に、NRRL Y−30752株(Shemerとして知られる製品、バイエル・クロップ・
サイエンス社(Bayer Crop Science)(ドイツ)製)、ミクロスパエロプシス・オクラケア(Microsphaeropsis ochracea)(Microxとして知られる製品、プロフィタ社(Prophyta)(ドイツ)製)、ムコール・ヒエマリス(Mucor hiemalis)(BioAvardとして知られる製品)、ムスコドル・アルブス(Muscodor albus)、特に、QST20799株(受入番号NRRL30547)(ArabesqueTM、Glissade(商標)、またはAndanteTMとして知られる製品、アグラクエスト社(Agraquest)製、米国)、ムスコドル・ロセウス(Muscodor roseus)A3−5株(受入番号NRRL30548)、ミロテキウム・ベルカリア(Myrothecium verrucaria)、特に、AARC−0255株(DiTeraTMとして知られる製品、バレント・バイオサイエンス社(Valent Biosciences)製)、ノムラエア・リレユィ(Nomuraea rileyi)、特に、SA86101株、GU87401株、SR86151株、CG128株およびVA9101
株(Kongoとして知られる製品)、オピオストマ・ピリフェルム(Ophiostoma piliferum)、特に、D97株(Sylvanexとして知られる製品)、ペシロマイセス・フモソロセウス(Paecilomyces fumosoroseus)(新:イサリア・フモソロセア(Isaria fumosorosea))、特に、IFPC200613株、またはapopka97株(PreFeRal WGとして知られる製品、バイオベスト社(Biobest)製)、ペシロマイセス・リラキヌス(Paecilomyces lilacinus)、特に、ペシロマイセス・リラキヌス(P. lilacinus)251株の胞子(AGAL89/030550)、(BioActとして知られる製品、プロフィタ社(Prophyta)(ドイツ)製;Crop Protection 2008, 27, 352-361を参照、ペシロマイセス・バリオティ(Paecilomyces variotii)、特に、Q−09株(Nemaquimとして知られる製品)、パンドラ・デルパキス(Pandora delphacis)、ペニシリウム・ビライイ(Penicillium bilaii)、特に、ATCC22348株、ペニシリウム・ベルミクラツム(Penicillium vermiculatum)(Vermiculenとして知られる製品)、プレビオプシス・ギガンテア(Phlebiopsis gigantea)(=プレビア・ギガンテア(Phlebia gigantea)=ペニオポラ・ギガンテア(Peniophora gigantea))(Rotstopとして知られる製品)、ピキア・アノマラ(Pichia anomala)、特に、
WRL−076株、ポコニア・クラミドスポリア(Pochonia chlamydosporia)、プセウドジマ・フロクロサ(Pseudozyma flocculosa)、特に、PF−A22 UL株、ピティウム・オリガンドルム(Pythium oligandrum)DV74、タラロミセス・フラブス(Talaromyces flavus)、特に、V117b株(PROTUS WGとして知られる製品、プロフィタ社(Prophyta)(ドイツ)製)、トリコデルマ・アルブム(Trichoderma album)(Bio Zeidとして知られる製品、オーガニック・バイオテクノロジー社(Organic Biotechnology)製、エジプト)、トリコデルマ・アスペレルム(Trichoderma asperellum)、特に、ICC012株、トリコデルマ・アトロビリデ(Trichoderma atroviride)、特に、アグラクエスト社(Agraquest)(米国)製のSC1株、トリコデルマ・ガムシイ(Trichoderma gamsii)(旧称:トリコデルマ・ビリデ(T. viride))、特に、ICC080株(IMI CC 392151 CABI)(Biodermaとして知られる製品)、トリコデルマ・ハルマツム(Trichoderma harmatum)、トリコデルマ・ハルジアヌム(Trichoderma harzianum)、特に、トリコデルマ・ハルジアヌム・リファイ(T. harzianum rifai)T39(Trichodexとして知られる製品、マクテシム社(Makhteshim)製、米国)、またはトリコデルマ・ハルジアヌム・リファイ(T. harzianum rifai)KRL−AG2株(T−22株、/ATCC208479)(PLANTSHIELD T−22G、RootshieldおよびTurfShieldとして知られる
製品、バイオワークス社(BioWorks)製、米国)、トリコデルマ・サツルニスポリウム(Trichoderma saturnisporium)、特に、プロフィタ社(Prophyta)製のPBP−TH−001株、トリコデルマ・コニンギイ(Trichoderma koningii)(Trikot−S Plusとして知られる製品)、トリコデルマ・リグノルム(Trichoderma lignorum)(Mycobacとして知られる製品)、トリコデルマ・ポリスポルム(Trichoderma polysporum)、特に、IMI206039株、トリコデルマ・ビレンス(Trichoderma virens)(Gliocladium virensとしても知られている)、特に、GL−21株(SoilGardとして知られる製品、セルティス社(Certis)製、米国)、トスカムレッラ・パウロメタボラ(Tsukamurella paurometabola)(HeberNemとして知られる製品)、ウロクラディウム・オウデマンシイ(Ulocladium oudemansii)(Botry−Zenとして知られる製品)、ベルティシリウム・アルボ−アトルム(Verticillium albo-atrum)、特に、WCS850株、ベルティシリウム・クラミドスポリウム(Verticillium chlamydosporium)(Varshaとして知られる製品)、ベルティシリウム・ダフリアエ(Verticillium dahliae)(Dutch Trigとして知られる製品)、およびゾオプトラ・ラディカンス(Zoophtora radicans)。
アドクソフィエス・オラナ(Adoxophyes orana)(サマーフルーツハマキガ(summer fruit tortrix))顆粒病ウイルス(GV)、(BIOFA−Capexとして知られる製品)、アグロティス・セゲツム(Agrotis segetum)(カブラヤガ(turnip moth))核多核体病ウイルス(NPV)、アンティカルシア・ゲムマタリス(Anticarsia gemmatalis)
(ウッディピロールモス(woolly pyrol moth))mNPV(Polygenとして知られる製品)、オートグラファ・カリフォルニカ(Autographa californica)(アルファルファルーパー(alfalfa looper))mNPV(VPN80として知られる製品、アグリコラ・EI・ソル社(Agricola El Sol)製)、ビストン・スプレサリア(Biston suppressaria)(ティールーパー(tea looper))NPV、カイコ(Bombyx mori)(カイコ(silkworm))NPV、クリプトプレビア・レウコトレタ(Cryptophlebia leucotreta)(フォールスコドリンガ(false codling moth))GV(Cryptexとして知られる製品)、キディア・ポモネラ(Cydia pomonella)(コドリンガ(codling moth))顆粒病ウイルス(GV)(Madex Plusとして知られる製品)、デンドロリムス・プンクタツス(Dendrolimus punctatus)(マッソンパインモス(masson pine moth))CPV、オオタバコガ(Helicoverpa armigera)NPV(AgBiTech−ViVUS Maxとして知られる製品)、ヘリコベルパ・ゼア(Helicoverpa zea)(以前はヘリオティス・ゼア(Heliothis zea))(コーンイアーワーム(corn earworm))NPV(Elcarとして知られる製品)、レウコマ・サリキス(Leucoma salicis)(ヨーロッパヤナギドクガ(satin moth))NPV、マイマイガ(Lymantria dispar)(マイマイガ(gypsy moth))NPV(Gypcheckとして知られる製品)、ネオディプリオン・アビエティス(Neodiprion abietis)(バルサムモミハバチ(balsam-fir sawfly))NPV(
Abietivとして知られる製品)、ネオディプリオン・レコンテイ(Neodiprion lecontei)(レッドヘッディドパインソーフライ(red-headed pinesawfly))NPV(Lecontvirusとして知られる製品)、ネオディプリオン・セルティフェル(Neodiprion sertifer)(マツハバチ(pine sawfly))NPV(Neocheck−Sとして知られる製品)、オルギア・プセウドトスガタ(Orgyia pseudotsugata)(米マツドクガ(douglas-fir tussock moth))NPV(Virtussとして知られる製品)、プトリマエア・オペルクレラ(Phthorimaea operculella)(タバコリーフマイナー(tobacco leaf miner))GV(Matapolとして知られる製品)、モンシロチョウ(Pieris rapae)(モンシロチョウ(small white))GV、プルテラ・クシロステラ(Plutella xylostella)(コナガ(diamondback moth))GV(Plutecとして知られる製品)、スポドプテラ・アルブラ(Spodoptera albula)(グレイストリーキッドアーミーワームモス(gray-streaked armywom moth))mNPV(VPN82として知られる製品)、スポドプテラ・エクセムプタ(Spodoptera exempta)(トゥルーアーミーワーム(true armyworm))mNPV(Spodecとして知られる製品)、スポドプテラ・エクシグア(Spodoptera exigua)(サトウダイコンアーミーワーム(sugarbeet armyworm))mNPV(Spexitとして知られる製品、アンダーマット・バイオコントロール社(Andermatt Biocontrol)製)、ヨトウガ(Spodoptera frugiperda)(フォールアーミーワーム(fall armyworm))mNPV(Baculovirus VPNとして知られる製品)、エジプトヨトウ(Spodoptera littoralis)(タバコカットワーム(tobacco cutworm))NPV(Spodoptrinとして知られる製品、NPPカリオペ社(NPP Calliope)、フランス)、およびハスモンヨトウ(Spodoptera litura)(オリエンタルリーフワームモス(oriental leafworm moth))NPV(Littovirとして知られる製品)。
アブレビアタ・カウカシカ(Abbreviata caucasica)、アクアリア属種(Acuaria spp.)、アガメルミス・デカウダタ(Agamermis decaudata)、アラントネマ属種(Allantonema spp.)、アムピメルミス属種(Amphimermis spp.)、ベディンギア・シリディコラ(Beddingia siridicola(=デラデヌス・シリディコラ(Deladenus siridicola))、ボビエ
ネマ属種(Bovienema spp.)、カメロニア属種(Cameronia spp.)、キトウッディエラ・オボフィラメンタ(Chitwoodiella ovofilamenta)、コントルチレンクス属種(Contortylenchus spp.)、クリキメルミス属種(Culicimermis spp.)、ディプロトリアエナ属種(Diplotriaena spp.)、エムピドメルミス属種(Empidomermis spp.)、フィリプイェビメルミス・レイプサンドラ(Filipjevimermis leipsandra)、ガストロメルミス属種(Gastromermis spp.)、ゴンギロネマ属種(Gongylonema spp.)、ギノポエキリア・プセウドビパラ(Gynopoecilia pseudovipara)、ヘテロラブディティス属種(Heterorhabditis spp.)、特に、ヘテロラブディティス・バクテリオポラ(Heterorhabditis bacteriophora)(B−GreenまたはLarvanem、KoppertまたはNemasys
Gとして知られる製品、バッカー・アンダーウッド社(Becker Underwood))、またはヘテロラブディティス・バウヤルディ(Heterorhabditis baujardi)、またはヘテロラブディティス・ヘリオティディス(Heterorhabditis heliothidis)(Nematonとして知られる製品、バイオヘルプ有限責任会社(biohelp GmbH))、またはヘテロラブディティス・インディカ(Heterorhabditis indica)、ヘテロラブディティス・マレラツス(Heterorhabditis marelatus)、またはヘテロラブディティス・メギディス(Heterorhabditis megidis)(Larvanem M、KoppertもしくはMeginem、アンダーマット・バイオコントロールAG社(Andermatt Biocontrol AG)、またはNemasys−Hとして知られる製品)、ヘテロラブディティス・ゼアランディカ(Heterorhabditis zealandica)、ヘクサメルミス属種(Hexamermis spp.)、ヒドロメルミス属種(Hydromermis spp.)、イソメルミス属種(Isomermis spp.)、リムノメルミス属種(Limnomermis spp.)、マウパシナ・ウェイシ(Maupasina weissi)、メルミス・ニグレスケンス(Mermis nigrescens)、メソメルミス属種(Mesomermis spp.)、ネオメソメルミス属種(Neomesomermis spp.)、ネオパラシチレンクス・ルグロシ(Neoparasitylenchus rugulosi)、オクトミオメルミス属種(Octomyomermis spp.)、パラシタペレンクス属種(Parasitaphelenchus spp.)、パラシトラブディティス属種(Parasitorhabditis spp.)、パ
ラシチレンクス属種(Parasitylenchus spp.)、ペルティリメルミス・クリキス(Perutilimermis culicis)、パスマラブディティス・ヘルマプロディタ(Phasmarhabditis hermaphrodita)、フィサロプテラ属種(Physaloptera spp.)、プロトレラツス属種(Protrellatus spp.)、プテリゴデルマティテス属種(Pterygodermatites spp.)、ロマノメルミス属種(Romanomermis spp.)、セウラツム・カダラケンセ(Seuratum cadarachense)、スパエルラリオプシス属種(Sphaerulariopsis spp.)、スピルラ・グイアネンシス(Spirura guianensis)、ステイネルネマ属種(Steinernema spp.)(=ネオアプレクタナ属種(Neoaplectana spp.))、特に、ステイネルネマ・カルポカプサエ(Steinernema carpocapsae)(Biocontrol、Nemasys−C、NemAttackとして知られる製品)、またはステイネルネマ・フェルティアエ(Steinernema feltiae)(=ネオアプレクタナ・カルポカプサエ(Neoaplectana carpocapsae))、(Nemasys、Nemaflor、Nemaplus、NemaShieldとして知られる製品)、
またはステイネルネマ・グラセリ(Steinernema glaseri)(Biotopiaとして知られる製品)、またはステイネルネマ・クラウセイ(Steinernema kraussei)(Larvesureとして知られる製品)、またはステイネルネマ・リオブラベ(Steinernema riobrave)(Biovectorとして知られる製品)、またはステイネルネマ・スカプテリスキ(Steinernema scapterisci)(Nematac Sとして知られる製品)、またはステイネルネマ・スカラバエイ(Steinernema scarabaei)、またはステイネルネマ・シアムカヤイ(Steinernema siamkayai)、ストレルコビメルミス・ペテルセニ(Strelkovimermis peterseni)、スブルラ属種(Subulura spp.)、スルプレチレンクス・エロンガツス(Sulphuretylenchus elongatus)、およびテトラメレス属種(Tetrameres spp.)。
またはキツネタケ(Laccaria laccata)、ブーフナー菌(Lactobacillus buchneri)、パラグロムス属種(Paraglomus spp.)、ピソリトゥス・ティンクトルス(Pisolithus tinctorus)、シュードモナス属種(Pseudomonas spp.)、根粒菌属種(Rhizobium spp.)、特に、リゾビウム・フレディ(Rhizobium fredii)、またはエンドウ根粒菌(Rhizobium leguminosarum)、またはリゾビウム・ロティ(Rhizobium loti)、またはリゾビウム・メリロティ(Rhizobium meliloti)、またはリゾビウム・トリフォリイ(Rhizobium trifolii)、またはリゾビウム・トロピシ(Rhizobium tropici)、リゾポゴン・アミロポゴン(Rhizopogon amylopogon)、またはリゾポゴン・フルビグレバ(Rhizopogon fulvigleba)、またはリゾポゴン・ルテオルス(Rhizopogon luteolus)、またはリゾポゴン・ティンクトルス(Rhizopogon tinctorus)、またはリゾポゴン・ビロスルス(Rhizopogon villosullus)、またはスクレロデルマ属種(Scleroderma spp.)、特に、スクレロデルマ・ケパ(Scleroderma cepa)、またはスクレロデルマ・キトリヌム(Scleroderma citrinum)、スイルス属種(Suillus spp.)、特に、スイルス・グラヌラテス(Suillus granulates)、またはスイルス・プンクタタピエス(Suillus punctatapies)およびストレプトマイセス属種(Streptomyces spp.)。
アントレヌス属種(Anthrenus spp.)、アピオン属種(Apion spp.)、アポゴニア属種(Apogonia spp.)、アトマリア属種(Atomaria spp.)、アッタゲヌス属種(Attagenus spp.)、バリス・カエルレスケンス(Baris caerulescens)、ブルキディウス・オプテクツス(Bruchidius obtectus)、ブルクス属種(Bruchus spp.)、カッシダ属種(Cassida spp.)、セロトマ・トリフルカタ(Cerotoma trifurcata)、ケウトリンクス属種(Ceutorrhynchus spp.)、カエトクネマ属種(Chaetocnema spp.)、クレオヌス・メンディクス(Cleonus mendicus)、コノデルス属種(Conoderus spp.)、コスモポリテス属種(Cosmopolites spp.)、コステリトラ・ゼアランディカ(Costelytra zealandica)、クテニケラ属種(Ctenicera spp.)、クルクリオ属種(Curculio spp.)、サビカクムネヒラタムシ(Cryptolestes ferrugineus)、クリプトリンクス・ラパティ(Cryptorhynchus lapathi)、キリンドロコプツルス属種(Cylindrocopturus spp.)、デルメステス属種(Dermestes spp.)、ディアブロティカ属種(Diabrotica spp.)、ディコクロシス属種(Dichocrocis spp.)、ディクラディスパ・アルミゲラ(Dicladispa armigera)、ディロボデルス属種(Diloboderus spp.)、エピラクナ属種(Epilachna spp.)、エピトリクス属種(Epitrix spp.)、ファウスチヌス属種(Faustinus spp.)、ギビウム・プシロイデス(Gibbium psylloides)、グナトケルス・コルヌツス(Gnathocerus cornutus)、ヘルラ・ウンダリス(Hellula undalis)、ヘテロニクス・アラトル(Heteronychus arator)、ヘテロニクス属種(Heteronyx spp.)、ヒラモルパ・エレガンス(Hylamorpha elegans)、オウシュウイエカミキリ(Hylotrupes bajulus)、アルファルファタコゾウムシ(Hypera postica)、ヒポメケス・スクアモサス(Hypomeces squamosus)、ヒポテネムス属種(Hypothenemus spp.)、ラクノステルナ・コンサングイネア(Lachnosterna consanguinea)、ラシオデルマ・セリコルネ(Lasioderma serricorne)、ラテティクス・オリザエ(Latheticus oryzae)、ラトリディウス属種(Lathridius spp.)、レマ属種(Lema spp.)、
レプチノタルサ・デケムリネアタ(Leptinotarsa decemlineata)、レウコプテラ属種(Leucoptera spp.)、リソロプトルス・オリゾピルス(Lissorhoptrus oryzophilus)、リストロノツス属(Listronotus)(=ヒペロデス属(Hyperodes))種、リクスス属種(Lixus spp.)、ルペロモルパ・クサントデラ(Luperomorpha xanthodera)、ルペロデス属種(Luperodes spp.)、リクツス属種(Lyctus spp.)、メガスケリス属種(Megascelis spp.)、メラノツス属種(Melanotus spp.)、メリゲテス・アエネウス(Meligethes aeneus)、メロロンタ属種(Melolontha spp.)、ミグドルス属種(Migdolus spp.)、モノカムス属種(Monochamus spp.)、ナウパクツス・クサントグラプス(Naupactus xanthographus)、ネクロビア属種(Necrobia spp.)、ニプツス・ホロレウクス(Niptus hololeucus)、サイカブト(Oryctes rhinoceros)、ノコギリヒラタムシ(Oryzaephilus surinamensis)、オリザパグス・オリザエ(Oryzaphagus oryzae)、オティオリンクス属種(Otiorrhynchus spp.)、オキシケトニア・ユクンダ(Oxycetonia jucunda)、パエドン・
コクレアリアエ(Phaedon cochleariae)、フィロパガ属種(Phyllophaga spp.)、フィロパガ・ヘレリ(Phyllophaga helleri)、フィロトレタ属種(Phyllotreta spp.)、マメコガネ(Popillia japonica)、プレムノトリペス属種(Premnotrypes spp.)、プロステパヌス・トルンカツス(Prostephanus truncatus)、プシリオデス属種(Psylliodes spp.)、プティヌス属種(Ptinus spp.)、リゾビウス・ベントラリス(Rhizobius ventralis)、リゾペルタ・ドミニカ(Rhizopertha dominica)、シトフィルス属種(Sitophilus spp.)、シトピルス・オリザエ(Sitophilus oryzae)、スペノポルス属種(Sphenophorus spp.)、ステゴビウム・パニケウム(Stegobium paniceum)、ステルネクス属種(Sternechus spp.)、シムフィレテス属種(Symphyletes spp.)、タニメクス属種(Tanymecus spp.)、テネブリオ・モリトル(Tenebrio molitor)、テネブリオイデス・マウレタニクス(Tenebrioides mauretanicus)、コクヌストモドキ属種(Tribolium spp.)、トロゴデルマ属種(Trogoderma spp.)、チキウス属種(Tychius spp.)、キシロトレクス属種(Xylotrechus spp.)、ザブルス属種(Zabrus spp.)、ハチノスムクゲケシキスイ(Aethina tumida)、エピカエルス属種(Epicaerus spp.)、ネオガレルケラ属種(Neogalerucella spp.)、オウレマ属種(Oulema spp.)、オウレマ・オリザエ(Oulema oryzae)、リンコポルス属種(Rhynchophorus spp.)、リンコポルス・フェルギネウス(Rhynchophorus ferrugineus)、リンコポルス・パルマルム(Rhynchophorus palmarum)、シノクシロン・ペルフォランス(Sinoxylon perforans);
エキノクネムス属種(Echinocnemus spp.)、ヒメイエバエ属種(Fannia spp.)、ウマバエ属種(Gasterophilus spp.)、ツェツェバエ属種(Glossina spp.)、ハエマトポタ属種(Haematopota spp.)、ヒドレリア属種(Hydrellia spp.)、ヒドレリア・グリセオラ(Hydrellia griseola)、ヒレミア属種(Hylemya spp.)、シラミバエ属種(Hippobosca spp.)、ヒポデルマ属種(Hypoderma spp.)、リリオミザ属種(Liriomyza spp.)、キンバエ属種(Lucilia spp.)、ルツォミヤ属種(Lutzomyia spp.)、マンソニア属種(Mansonia spp.)、イエバエ属種(Musca spp.)、ヒツジバエ属種(Oestrus spp.)、オスキネラ・フリト(Oscinella frit)、パラタニタルスス属種(Paratanytarsus spp.)、
パララウテルボルニエラ・スブキンクタ(Paralauterborniella subcincta)、ペゴミア属種(Pegomyia spp.)、サシチョウバエ属種(Phlebotomus spp.)、ポルビア属種(Phorbia spp.)、ポルミア属種(Phormia spp.)、チーズバエ(Piophila casei)、プロディプロシス属種(Prodiplosis spp.)、プシラ・ロサエ(Psila rosae)、ラゴレティス属種(Rhagoletis spp.)、ニクバエ属種(Sarcophaga spp.)、ブユ属種(Simulium spp.)、サシバエ属種(Stomoxys spp.)、アブ属種(Tabanus spp.)、テタノプス属種(Tetanops spp.)、ティプラ属種(Tipula spp.)、ケラティティス属種(Ceratitis spp.)、オウトウショウジョウバエ(Drosophila suzukii)、エウレイア・ヘラクレイ(Euleia heraclei)、プラチパレア・ポエキロプテラ(Platyparea poeciloptera)、蛹生類(Pupipara)、トキソトリパナ・クルビカウダ(Toxotrypana curvicauda);
、ブレビコリネ・ブラシカエ(Brevicoryne brassicae)、カコプシラ属種(Cacopsylla spp.)、カリギポナ・マルギナタ(Calligypona marginata)、カプリニア属種(Capulinia spp.)、カルネオケパラ・フルギダ(Carneocephala fulgida)、ケラトバクナ・ラニゲラ(Ceratovacuna lanigera)、アワフキムシ科、ケロプラステス属種(Ceroplastes spp.)、カエトシポン・フラガエフォリイ(Chaetosiphon fragaefolii)、キオナスピス・テガレンシス(Chionaspis tegalensis)、クロリタ・オヌキイ(Chlorita onukii)、
コンドラクリス・ロセア(Chondracris rosea)、クロマピス・ユグランディコラ(Chromaphis juglandicola)、クリソムパルス・フィクス(Chrysomphalus ficus)、キカドゥリナ・ムビラ(Cicadulina mbila)、ココミティルス・ハリ(Coccomytilus halli)、コクス属種(Coccus spp.)、クリプトミズス・リビス(Cryptomyzus ribis)、クリプトネオサ属種(Cryptoneossa spp.)、クテナリタイナ属種(Ctenarytaina spp.)、ダルブルス属種(Dalbulus spp.)、ミカンコナジラミ(Dialeurodes citri)、ミカンキジラミ(Diaphorina citri)、ディアスピス属種(Diaspis spp.)、ドロシカ属種(Drosicha spp.)、ディサピス属種(Dysaphis spp.)、ディスミコクス属種(Dysmicoccus spp.)、エムポアスカ属種(Empoasca spp.)、エリオソマ属種(Eriosoma spp.)、エリトロネウラ属種(Erythroneura spp.)、エウカリプトリマ属種(Eucalyptolyma spp.)、エウフィルラ属種(Euphyllura spp.)、エウスケリス・ビロバツス(Euscelis bilobatus)、フェリシア属種(Ferrisia spp.)、ゲオコクス・コフェアエ(Geococcus coffeae)、グリカスピス属種(Glycaspis spp.)、ヘテロプシラ・クバナ(Heteropsylla cubana)、ヘテロプシラ・スピヌロサ(Heteropsylla spinulosa)、ホマロディスカ・コアグラタ(Homalodisca coagulata)、ヒアロプテルス・アルンディニス(Hyalopterus arundinis)、
ワタフキカイガラムシ属種(Icerya spp.)、イディオケルス属種(Idiocerus spp.)、イディオスコプス属種(Idioscopus spp.)、ラオデルパクス・ストリアテルス(Laodelphax striatellus)、レカニウム属種(Lecanium spp.)、レピドサペス属種(Lepidosaphes spp.)、ニセダイコンアブラムシ(Lipaphis erysimi)、マクロシプム属種(Macrosiphum spp.)、マクロステレス・ファキフロンス(Macrosteles facifrons)、マハナルバ属種(Mahanarva spp.)、メラナピス・サカリ(Melanaphis sacchari)、メトカルフィエラ属種(Metcalfiella spp.)、メトポロピウム・ディロドゥム(Metopolophium dirhodum)、モネリア・コスタリス(Monellia costalis)、モネリオプシス・ペカニス(Monelliopsis pecanis)、ミズス属種(Myzus spp.)、ナソノビア・リビスニグリ(Nasonovia ribisnigri)、ツマグロヨコバイ属種(Nephotettix spp.)、ネティゴニクラ・スペクトラ(Nettigoniclla spectra)、ニラパルバタ・ルゲンス(Nilaparvata lugens)、オンコメトピア属種(Oncometopia spp.)、オルテジア・プラエロンガ(Orthezia praelonga)、オクシア・キネンシス(Oxya chinensis)、パキプシラ属種(Pachypsylla spp.)、ヤマモモコナジラミ(Parabemisia myricae)、パラトリオザ属種(Paratrioza spp.)
、パルラトリア属種(Parlatoria spp.)、ペムピグス属種(Pemphigus spp.)、ペレグリヌス・マイディス(Peregrinus maidis)、ペナコクス属種(Phenacoccus spp.)、ドロノキワタアブラムシ(Phloeomyzus passerinii)、ポロドン・フムリ(Phorodon humuli)、ネアブラムシ属種(Phylloxera spp.)、ピンナスピス・アスピディストラエ(Pinnaspis aspidistrae)、プラノコクス属種(Planococcus spp.)、プロソピドプシラ・フラバ(Prosopidopsylla flava)、ナシガタカタカイガラムシ(Protopulvinaria pyriformis)、クワシロカイガラムシ(Pseudaulacaspis pentagona)、プセウドコクス属種(Pseudococcus spp.)、プシロプシス属種(Psyllopsis spp.)、プシラ属種(Psylla spp.)、プテロマルス属種(Pteromalus spp.)、ピリラ属種(Pyrilla spp.)、クアドラスピディオツス属種(Quadraspidiotus spp.)、クエサダ・ギガス(Quesada gigas)、ラストロコクス属種(Rastrococcus spp.)、ロパロシプム属種(Rhopalosiphum spp.)、サイセティア属種(Saissetia spp.)、スカポイデウス・ティタヌス(Scaphoideus titanus)、スキザピス・グラミヌム(Schizaphis graminum)、セレナスピドゥス・アルティクラツス(Selenaspidus articulatus)、ソガタ属種(Sogata spp.)、ウンカ(Sogatella furcifera)、ソガトデス属種(Sogatodes spp.)、スティクトケパラ・フェスティナ(Stictocephala festina)、シポニヌス・ピリレアエ(Siphoninus phillyreae)、テナラパラ・マライェンシス(Tenalaphara malayensis)、テトラゴノケペラ属種(Tetragonocephela spp.)、ティノカリス・カリアエフォリアエ(Tinocallis caryaefoliae)、トマスピス属種(Tomaspis spp.)、トクソプテラ属種(Toxoptera spp.)、トリアレウロデス・バポラリオルム(Trialeurodes vaporariorum)、トリオザ属種(Trioza spp.)、
チプロキバ属種(Typhlocyba spp.)、ウナスピス属種(Unaspis spp.)、ビテウス・ビティフォリイ(Viteus vitifolii)、ジギナ属種(Zygina spp.)、アレウロカンツス属種(Aleurocanthus spp.)、クリソムパルス・アオニドゥム(Chrysomphalus aonidum)、ディアレウロデス・キテンデニ(Dialeurodes chittendeni)、ディウラピス属種(Diuraphis spp.)、フィオリニア属種(Fiorinia spp)、フルカスピス・オケアニカ(Furcaspis oceanica)、ロポレウカスピス・ヤポニカ(Lopholeucaspis japonica)、ネオマスケリア属種(Neomaskellia spp.)、ペルキンシエラ属種(Perkinsiella spp.)、プルビナリア属種(Pulvinaria spp.);
クネパシア属種(Cnephasia spp.)、コノポモルパ属種(Conopomorpha spp.)、コノトラケルス属種(Conotrachelus spp.)、コピタルシア属種(Copitarsia spp.)、キディア属種(Cydia spp.)、ダラカ・ノクツイデス(Dalaca noctuides)、ディアパニア属種(Diaphania spp.)、ディアトラエア・サカラリス(Diatraea saccharalis)、エアリアス属種(Earias spp.)、エクディトロパ・アウランティウム(Ecdytolopha aurantium)、エラスモパルプス・リグノセルス(Elasmopalpus lignosellus)、エルダナ・サッカリナ(Eldana saccharina)、エペスティア属種(Ephestia spp.)、エピノティア属種(Epinotia spp.)、エピフィアス・ポストビタナ(Epiphyas postvittana)、エティエラ属種(Etiella spp.)、エウリア属種(Eulia spp.)、エウポエキリア・アムビグエラ(Eupoecilia ambiguella)、ドクガ属種(Euproctis spp.)、エウクソア属種(Euxoa spp.)、フェルティア属種(Feltia spp.)、ハチノスツヅリガ(Galleria mellonella)、グラキラリア属種(Gracillaria spp.)、グラポリタ属種(Grapholitha spp.)、ヘディレプタ属種(Hedylepta spp.)、ヘリコベルパ属種(Helicoverpa spp.)、ヘリオティス属種(Heliothis spp.)、ホフマンノピラ・プセウドスプレテラ(Hofmannophila pseudospretella)、ホモエオソマ属種(Homoeosoma spp.)、ホモナ属種(Homona spp.)、ヒポノメウタ・パデラ(Hyponomeuta padella)、カキボリア・フラボファスキアタ(Kakivoria flavofasciata)、ラフィグマ属種(Laphygma spp.)、ラスペユレシア・モレスタ(Laspeyresia molesta)、レウキノデス・オルボナリス(Leucinodes orbonalis)、レウコプテラ属種(Leucoptera spp.)、リトコレティス属種(Lithocolletis spp.)、リトパネ・アンテンナタ(Lithophane antennata)、ロベシア属種(Lobesia spp.)、ロクサグロティス・アルビコスタ(Loxagrotis albicosta)、マイマイガ属種(Lymantria spp.)、
リオネティア属種(Lyonetia spp.)、マラコソマ・ネウストリア(Malacosoma neustria)、マルカ・テストラリス(Maruca testulalis)、マムストラ・ブラシカエ(Mamstra brassicae)、メラニティス・レダ(Melanitis leda)、モキス属種(Mocis spp.)、モノピス・オブビエラ(Monopis obviella)、アワヨトウ(Mythimna separata)、ネマポゴン・クロアケルス(Nemapogon cloacellus)、ニムプラ属種(Nymphula spp.)、オイケティクス属種(Oiketicus spp.)、オリア属種(Oria spp.)、オルタガ属種(Orthaga spp.)、オストリニア属種(Ostrinia spp.)、パノリス・フラムメア(Panolis flammea)、パルナラ属種(Parnara spp.)、ペクティノポラ属種(Pectinophora spp.)、ペリレウコプテラ属種(Perileucoptera spp.)、プトリマエア属種(Phthorimaea spp.)、フィロクニスティス・キトレラ(Phyllocnistis citrella)、フィロノリクテル属種(Phyllonorycter spp.)、ピエリス属種(Pieris spp.)、プラチノタ・スツルタナ(Platynota stultana)、プロディア・インテルプンクテラ(Plodia interpunctella)、プルシア属種(Plusia spp.)、プルテラ・クシロステラ(Plutella xylostella)、プライス属種(Prays spp.)、プロデニア属種(Prodenia spp.)、プロトパルケ属種(Protoparce spp.)、プセウダレティア属種(Pseudaletia spp.)、プセウダレティア・ウニプンクタ(Pseudaletia unipuncta)、プセウドプルシア・インクルデンス(Pseudoplusia includens)、ピラウスタ・ヌビラリス(Pyrausta nubilalis)、ラキプルシア・ヌ(Rachiplusia nu)、スコエノビウス属種(Schoenobius spp.)、スキルポパガ属種(Scirpophaga spp.)、スキルポパガ・インノタタ(Scirpophaga innotata)、スコティア・セゲツム(Scotia segetum)、セサミア属種(Sesamia spp.)、セサミア・インフェレンス(Sesamia inferens)、スパルガノティス属種(Sparganothis spp.)、スポドプテラ属種(Spodoptera spp.)、スポドプテラ・プラエフィカ(Spodoptera praefica)、スタトモポダ属種(Stathmopoda spp.)、ストモプテリクス・スプセキベラ(Stomopteryx subsecivella)、シナンテドン属種(Synanthedon spp.)、テキア・ソラニボラ(Tecia solanivora)、
テルメシア・ゲムマタリス(Thermesia gemmatalis)、ティネア・クロアケラ(Tinea cloacella)、イガ(Tinea pellionella)、コイガ(Tineola bisselliella)、トルトリクス属種(Tortrix spp.)、ジュウタンガ(Trichophaga tapetzella)、トリコプルシア属種(Trichoplusia spp.)、トリポリザ・インケルツラス(Tryporyza incertulas)、ツタ・アプソルタ(Tuta absoluta)、ビラコラ属種(Virachola spp.)、オートグラファ属種(Autographa spp.)、ブラストダクナ・アトラ(Blastodacna atra)、コレウティス・パリアナ(Choreutis pariana)、クリソデイクシス・カルキテス(Chrysodeixis chalcites)、ディパロプシス属種(Diparopsis spp.)、エランニス属種(Erannis spp.)、エルスコビエラ・ムスクラナ(Erschoviella musculana)、エウドキマ属種(Eudocima spp.)、ラムピデス属種(Lampides spp.)、マルカ属種(Maruca spp.)、オムピサ属種(Omphisa spp.)、オペロプテラ属種(Operophtera spp.)、ステノマ属種(Stenoma spp.)、タウメトポエア属種(Thaumetopoea spp.);
、肺吸虫属種(Paragonimus spp.)、スキストソメン属種(Schistosomen spp.)、ストロンギロイデス・フエレボルニ(Strongyloides fuelleborni)、糞線虫(Strongyloides stercoralis)、糞線虫属種(Strongyloides spp.)、無鉤条虫(Taenia saginata)、有鉤条虫(Taenia solium)、旋毛虫(Trichinella spiralis)、トリキネラ・ナティバ(Trichinella nativa)、トリキネラ・ブリトビ(Trichinella britovi)、トリキネラ・ネルソニ(Trichinella nelsoni)、トリキネラ・プセウドプシラリス(Trichinella pseudopsiralis)、トリコストロングルス属種(Trichostrongulus spp.)、トリクリス・トリクリア(Trichuris trichuria)、バンクロフト糸状虫(Wuchereria bancrofti);
N−[1−(2,6−ジフルオロフェニル)−1H−ピラゾール−3−イル]−2−(トリフルオロメチル)ベンズアミド(化合物(Ia))の調製
まず、2,6−ジフルオロフェニルヒドラジンヒドロクロリド(2.00g)をエタノール(20ml)に加え、ナトリウムエトキシド(エタノール中21%、3.02g)を室温でゆっくりと滴加し、この混合物を10分間撹拌し、アクリロニトリル(0.80ml)を加え、この混合物を一晩加熱還流した。この反応混合物を次に、減圧濃縮し、ジクロロメタンに溶解させ、水で洗浄し、硫酸ナトリウムで乾燥させ、減圧下で濃縮乾固した。残留物は1.40gの表題化合物であり、これを次の段階でさらなる精製無しで使用した。
氷冷しながら、1−(2,6−ジフルオロフェニル)−4,5−ジヒドロ−1H−ピラゾール−3−アミン(Ia−1)(前段階からの1.40g)を、無水酢酸(6ml)に溶解させ、室温で一晩撹拌した。この混合物を次に、酢酸エチルで希釈し、水で洗浄し、硫酸ナトリウムで乾燥させ、減圧下で濃縮乾固した。残渣を移動相シクロヘキサン/酢酸エチル(勾配=2時間、100%シクロヘキサン〜100%酢酸エチル)を用いるシリカゲルカラムクロマトグラフィで精製した。これにより、537mgの表題化合物が得られた。HPLC-MS: logP = 1.46; 質量(m/z): 240.0 (M+H)+; 1H-NMR (DMSO-D6) 1.99 (s, 3H), 3.26 (t, 2H), 3.65 (t, 2H), 7.04 ‐ 7.10 (m, 2H), 7.11 ‐ 7.18 (m, 1H), 10.59 (br. s, 1H).
N−[1−(2,6−ジフルオロフェニル)−4,5−ジヒドロ−1H−ピラゾール−3−イル]アセトアミド(Ia−2)(200mg)をまず1,4−ジオキサン(1ml)に加え、2,3−ジクロロ−5,6−ジシアノ−1,4−ベンゾキノン(209mg)を加え、この混合物を室温で30分間撹拌した。反応混合物を濾過し、濾液を減圧下で濃縮乾固した。残渣を移動相シクロヘキサン/酢酸エチル(勾配=2時間、100%シクロヘキサン〜100%酢酸エチル)を用いるシリカゲルカラムクロマトグラフィで精製した。これにより、140mgの表題化合物が得られた。
N−[1−(2,6−ジフルオロフェニル)−1H−ピラゾール−3−イル]アセトアミド(Ia−3)(50mg)をまず水(1ml)に加え、濃塩酸(0.07ml)を加え、この混合物を8時間加熱還流した。この反応混合物を次に、濃水酸化ナトリウム水溶液でアルカリ性にし、ジクロロメタンで抽出した。有機相を減圧下で濃縮乾固した。これにより、25mgの表題化合物が得られた。
1−(2,6−ジフルオロフェニル)−1H−ピラゾール−3−アミン(Ia−4)(1g)をまずジクロロメタン(10ml)に加えた。この反応混合物を0℃に冷却し;2.142mLのトリエチルアミンを加えた。次に、2−(トリフルオロメチル)ベンゾイルクロリド(1.175g)を0℃〜5℃の温度で滴加した。この反応混合物を室温で一晩撹拌した。次に、いくらかのジクロロメタンおよび水を加えた。有機相を分離し、乾燥させ、蒸発させた。得られた残渣を、シクロヘキサン/酢酸エチルの勾配を用いるシリカゲルカラムクロマトグラフィで精製した。これにより、1.2gの表題化合物が得られた。
1H−ピラゾール−3−アミン(1.80g)をまずアセトニトリル(50ml)に加え、2,3,5−トリフルオロピリジン(2.88g)および炭酸カリウム(5.99g)を加え、この混合物を一晩加熱還流した。この反応混合物を次に、減圧濃縮し、ジクロロメタンに溶解させ、水で洗浄し、硫酸ナトリウムで乾燥させ、減圧下で濃縮乾固した。残渣を移動相シクロヘキサン/酢酸エチル(勾配=2時間、100%シクロヘキサン〜100%酢酸エチル)を用いるシリカゲルカラムクロマトグラフィで精製した。これにより、610mgの表題化合物が得られた。
1−(3,5−ジフルオロピリジン−2−イル)−1H−ピラゾール−3−アミン(Ib−1)(300mg)をまずジクロロメタン(2ml)に加えた。この反応混合物を0℃に冷却し;0.640mlのトリエチルアミンを加えた。次に、2−(トリフルオロメチル)ベンゾイルクロリド(0.256ml)を0℃〜5℃の温度で滴加した。この反応混合物を室温で一晩撹拌した。次に、いくらかのジクロロメタンおよび水を加えた。有機相を分離し、乾燥させ、蒸発させた。得られた残渣を、シクロヘキサン/酢酸エチルの勾配を用いるシリカゲルカラムクロマトグラフィで精製した。これにより、506mgの表題化合物が得られた。
0.1molの2,6−ジフルオロフェニルヒドラジンおよび0.12molのイソニトロソアセトンをエタノール中で3時間加熱還流した。室温に冷却した後、沈殿した固体を濾去し、エタノールで洗浄し、乾燥させた。これにより、表題化合物(理論値の75%)が得られた。
無水酢酸中の0.1molの2−[2−(2,6−ジフルオロフェニル)ヒドラジニリデン]プロパナルオキシム(Ic−1)の溶液を、120℃にゆっくりと加熱し、この温度で2時間撹拌した。過剰の無水酢酸をロータリーエバポレーターで除去した。表題化合物を得て(理論値の65%)、さらなる精製無しで使用した。
0.2molの二クロム酸ナトリウムを、66%硫酸中の0.1molの2−(2,6−ジフルオロフェニル)−4−メチル−2H−1,2,3−トリアゾール(Ic−2)の十分に撹拌した溶液に加えた。フラスコ中のCr6+の黄色〜オレンジ色が消えた後に初めて、二クロム酸塩の各々の部分を加えた。さらに、フラスコ内の温度が約80〜90℃のままであるように、前記部分を加えた。次に、この混合物を1時間加熱した。冷却後、この混合物をおよそ同量の氷に注ぎ、一晩放置した。沈殿した酸(Ic−3)を濾去し、水で洗浄し、乾燥させた。これにより、表題化合物(理論値の50%)が得られた。
塩化水素を、メタノール中の2−(2,6−ジフルオロフェニル)−2H−1,2,3−トリアゾール−4−カルボン酸(Ic−3)の沸騰溶液に2時間バブリングさせた。冷却後、表題化合物の白色結晶を濾去(filtered off)した(理論値の85%)。
メチル2−(2,6−ジフルオロフェニル)−2H−1,2,3−トリアゾール−4−カルボキシレート(Ic−4)を、過剰量の1.5等量のエタノール中ヒドラジン水和物と共に4時間煮沸した。冷却後、ヒドラジド(Ic−5)の結晶を水と共に煮沸し、乾燥させた。これにより、表題化合物(理論値の90%)が得られた。
亜硝酸ナトリウム水溶液を、20%塩酸水溶液中の2−(2,6−ジフルオロフェニル)−2H−1,2,3−トリアゾール−4−カルボヒドラジド(Ic−5)の懸濁液に加えた。10℃でさらに撹拌した後、アシルアジド(Ic−6)の結晶を濾去し、水で洗浄し、室温の減圧下で乾燥させた。これにより、表題化合物(理論値の75%)が得られた。
乾燥させた2−(2,6−ジフルオロフェニル)−2H−1,2,3−トリアゾール−4−カルボニルアジド(Ic−6)を、気体の発生が終わるまで(約2時間)トルエン中で煮沸した。次に、トルエンをロータリーエバポレーターで除去したところ、粘稠性残渣であるイソシアネート(Ic−7)は、直接的に、さらなる精製無しで次の段階への準備ができていた。これにより、表題化合物(理論値の90%)が得られた。
2−(2,6−ジフルオロフェニル)−2H−1,2,3−トリアゾール−4−カルボニルイソシアネート(Ic−7)を、30分間の塩酸中での煮沸によって加水分解した。残渣の揮発性物質をロータリーエバポレーターで除去し、残渣を炭酸ナトリウム溶液で処理した。沈殿した結晶を濾去し、水で洗浄し、ヘキサンから再結晶させた。これにより、表題化合物(理論値の70%)が得られた。
2,2−(2,6−ジフルオロフェニル)−2H−1,2,3−トリアゾール−4−アミン(Ic−8)(150mg)を、3.9mlのジクロロメタン中の2−(トリフルオロメチル)ベンゾイルクロリド(160mg)およびトリエチルアミン(0.21ml)と反応させた。カラムクロマトグラフィおよび分取HPLCによる精製によって、143mgの表題化合物を得た。HPLC-MS: logP = 2.80;質量(m/z): 369.1 (M+H)+; 1H-NMR (CD3CN) 7.45 ‐ 7.49 (m, 2H), 7.70 ‐ 7.77 (m, 4H), 7.78 ‐ 7.88 (m, 1H), 8.45 (s, 1H), 11.83 (s, 1H).
2つの化合物の組合せ有効性についての式
2つの化合物の所与の組合せの予測される有効性は、以下のように算出される(Colby, S.R., “Calculating Synergistic and antagonistic Responses of Herbicide Combinations”, Weeds 15, pp. 20-22, 1967を参照):
Yが、n ppmまたはn g/haの濃度の試験化合物Bについての、無処理対照の%死亡率で表される有効性であり、
Eが、それぞれmおよびn ppm、mおよびn g/haのAおよびBの混合物を用いる、無処理対照の%死亡率で表される有効性である場合、
サツマイモネコブセンチュウ(Meloidogyne incognita)試験
溶媒:125.0重量部のアセトン
適切な活性化合物調製物を作製するため、1重量部の活性化合物を記載量の溶媒と混合し、濃縮物を水で所望の濃度に希釈する。適切な胞子懸濁液調製物を作製するため、胞子を所望の濃度に水で希釈する。
ヨトウガ(Spodoptera frugiperda)−灌注試験
溶媒:7重量部のジメチルホルムアミド
乳化剤:2重量部のアルキルアリールポリグリコールエーテル
適切な活性化合物調製物を作製するため、1重量部の活性化合物を記載量の溶媒および乳化剤と混合し、水で所望の濃度に希釈する。濃度の算出には、土壌体積が含まれなければならない。土壌中の乳化剤濃度が40ppmを超えないように注意する必要である。さらなる試験濃度は水での希釈によって準備する。
サツマイモネコブセンチュウ(Meloidogyne incognita)−灌注試験
溶媒:7重量部のジメチルホルムアミド
乳化剤:2.5重量部のアルキルアリールポリグリコールエーテル
適切な活性化合物調製物を作製するため、1重量部の活性化合物を記載量の溶媒および乳化剤と混合し、水で所望の濃度に希釈する。濃度の算出には、土壌体積が含まれなければならない。土壌中の乳化剤濃度が20ppmを超えないように注意する必要である。さらなる試験濃度は水での希釈によって準備する。
ミズス・ペルシカエ(Myzus persicae)−灌注試験
溶媒:7重量部のジメチルホルムアミド
乳化剤:2重量部のアルキルアリールポリグリコールエーテル
適切な活性化合物調製物を作製するため、1重量部の活性化合物を記載量の溶媒および乳化剤と混合し、水で所望の濃度に希釈する。濃度の算出には、土壌体積が含まれなければならない。土壌中の乳化剤濃度が40ppmを超えないように注意する必要である。さらなる試験濃度は水での希釈によって準備する。
ナミハダニ(Tetranychus urticae)−灌注試験;OP耐性
溶媒:7重量部のジメチルホルムアミド
乳化剤:2重量部のアルキルアリールポリグリコールエーテル
適切な活性化合物調製物を作製するため、1重量部の活性化合物を記載量の溶媒および乳化剤と混合し、水で所望の濃度に希釈する。濃度の算出には、土壌体積が含まれなければならない。土壌中の乳化剤濃度が40ppmを超えないように注意する必要である。さらなる試験濃度は水での希釈によって準備する。
Claims (10)
- 式(I):
AがA−1.0またはA−2.0であり、点線がQのN原子への結合を表しており;
QがQ−1.0またはQ−2.0であり、窒素が環Aに結合しており、矢印がいずれの場合にもNHCO部分への結合を表しており;
WがW1〜W11:
の化合物、並びに、下記の表:
を含んでなる、活性成分組み合わせ物。 - 式(I)において、AがA−1.0であり、QがQ−1.0であり、WがW1である、請求項1に記載の活性成分組み合わせ物。
- 式(I)において、AがA−2.0であり、QがQ−1.0であり、WがW1である、請求項1に記載の活性成分組み合わせ物。
- 式(I)において、AがA−1.0であり、QがQ−2.0であり、WがW1である、請求項1に記載の活性成分組み合わせ物。
- 式(I)の化合物に加えて、前記表に特定される化合物から選択されるただ1つの化合物/生物防除剤が存在する、請求項1〜4のいずれか一項に記載の活性成分組み合わせ物。
- 動物害虫を防除するための、請求項1〜5のいずれか一項に記載の活性成分組み合わせ物の使用。
- 種子、土壌および植物を処理するための、請求項1〜5のいずれか一項に記載の活性成分組み合わせ物の使用。
- トランスジェニック植物に対する、請求項1〜5のいずれか一項に記載の活性成分組み合わせ物の使用。
- 請求項1〜5に記載の活性成分組み合わせ物、並びに1つもしくは2つ以上の増量剤および/または1つもしくは2つ以上の界面活性剤を含有する、組成物。
- 請求項1〜5のいずれか一項に記載の活性成分組み合わせ物を、1つもしくは2つ以上の増量剤および/または1つもしくは2つ以上の界面活性剤と混合することを特徴とする、作物保護組成物を製造するための方法。
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PCT/EP2015/056219 WO2015144683A1 (en) | 2014-03-27 | 2015-03-24 | Insecticidal and nematocidal active ingredient combinations |
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PE20161029A1 (es) | 2016-11-09 |
PH12016501883B1 (en) | 2016-12-19 |
CL2016002300A1 (es) | 2017-06-23 |
ES2762787T3 (es) | 2020-05-25 |
TW201622570A (zh) | 2016-07-01 |
DOP2016000257A (es) | 2016-10-31 |
GT201600198A (es) | 2019-07-29 |
US10757939B2 (en) | 2020-09-01 |
EP3122188B1 (en) | 2019-10-09 |
EP3122188A1 (en) | 2017-02-01 |
BR112016022213B1 (pt) | 2021-06-29 |
US20190281827A1 (en) | 2019-09-19 |
WO2015144683A1 (en) | 2015-10-01 |
US20170188581A1 (en) | 2017-07-06 |
MX2016012059A (es) | 2017-01-19 |
CR20160391A (es) | 2016-10-05 |
AR099827A1 (es) | 2016-08-24 |
JP6464186B2 (ja) | 2019-02-06 |
PH12016501883A1 (en) | 2016-12-19 |
BR112016022213A2 (pt) | 2017-10-31 |
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