JP2010509276A - フィプロニルの結晶変態 - Google Patents
フィプロニルの結晶変態 Download PDFInfo
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- JP2010509276A JP2010509276A JP2009535707A JP2009535707A JP2010509276A JP 2010509276 A JP2010509276 A JP 2010509276A JP 2009535707 A JP2009535707 A JP 2009535707A JP 2009535707 A JP2009535707 A JP 2009535707A JP 2010509276 A JP2010509276 A JP 2010509276A
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- Prior art keywords
- fipronil
- crystal modification
- modification
- mixture
- composition
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- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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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
- A01N47/02—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 no bond to a nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
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- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
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- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
【選択図】なし
Description
(1)d=8.55±0.1Å 2θ=10.3±0.2°
(2)d=7.94±0.07Å 2θ=11.1±0.2°
(3)d=6.78±0.05Å 2θ=13.0±0.2°
(4)d=5.43±0.05Å 2θ=16.2±0.2°
(5)d=4.35±0.05Å 2θ=20.3±0.2°
(6)d=2.83±0.03Å 2θ=31.5±0.2°。
(i)結晶変態Vとは異なる固体形態のフィプロニルの、高温ジメチルスルホキシド又は高温アセトニトリルから選択される溶媒S中の溶液を調製するステップ;
(ii)高温溶液からフィプロニルの結晶化を行うステップ;並びに
(iii)得られた沈澱を単離するステップ
を含む方法を用いて製造することができる。
ステップ(i)で使用する、結晶変態Vとは異なる好適なフィプロニル形態は、例えば、非晶質フィプロニル、又は結晶性フィプロニル、例えば空間群C2/cの単斜晶系フィプロニル、空間群P21/cの単斜晶系フィプロニル、そしてまたフィプロニルの結晶変態の混合物から選択される。
本発明の方法のステップ(ii)では、続いてフィプロニルを結晶化する。
本発明の方法のステップ(iii)では、結晶変態Vを、液体から固体成分を分離する通例の技術を使用して、例えば、ろ過、遠心分離、又はデカントによって単離する。一般に、単離した沈殿は、例えば結晶化に使用した溶媒Sで洗浄する。洗浄は、1つ又は複数のステップで実施することができる。洗浄は、価値ある生成物の損失をできる限り小さくするために、典型的に30℃未満、特に25℃未満の温度で実施する。次いで、得られた結晶性フィプロニル又は変態Vを乾燥し、さらなる処理に供することができる。
アリ、ハチ、スズメバチ、ハバチ(膜翅目:Hymenoptera)、例えばアッタ・カピグアラ(Atta capiguara)、アッタ・セファロテス(Atta cephalotes)、アッタ・ラエビガタ(Atta laevigata)、アッタ・ロブスタ(Atta robusta)、アッタ・セクスデンス(Atta sexdens)、アッタ・テクサナ(Atta texana)、クレマトガスターspp.(Crematogaster spp.)、ホプロカムパ・ミヌタ(Hoplocampa minuta)、ホプロカヌパ・テスツジネア(Hoplocampa testudinea)、モノモリウム・ファラオニス(Monomorium pharaonis)、ソレノプシス・ジェミナタ(Solenopsis geminata)、ソレノプシス・インビクタ(Solenopsis invicta)、ソレノプシス・リクテリ(Solenopsis richteri)、ソレノプシス・キシロニ(Solenopsis xyloni)、フェイドール・メガセファラ(Pheidole megacephala)、収穫アリ(ポゴノミルメクス・バルバツス(Pogonomyrmex barbatus)及びポゴノミルメクス・カリフォルニクス(Pogonomyrmex californicus)など)、ダシムチラ・オシデンタリス(Dasymutilla occidentalis)、ボンバスspp.(Bombus spp.)、ベスプラ・スクアモサ(Vespula squamosa)、パラベスプラ・ブルガリス(Paravespula vulgaris)、パラベスプラ・ペンシルバニカ(Paravespula pennsylvanica)、パラベスプラ・ゲルマニカ(Paravespula germanica)、ドリコベスプラ・マクラタ(Dolichovespula maculata)、ベスパ・クラブロ(Vespa crabro)、ポリステス・ルビギノサ(Polistes rubiginosa)、カンポノツス・フロリダヌス(Camponotus floridanus)及びリネピテマ・フミレ(Linepithema humile)。
1.茎葉処理用に水で希釈する製品。種子処理に関しては、そのような製品は希釈若しくは未希釈で種子に施用することができる。
10重量部の活性化合物を90重量部の水又は水溶性溶媒に溶かす。別法として、湿展剤その他の補助剤を加える。活性化合物は、水で希釈すると溶解し、それによって10%(重量基準)の活性化合物を含む製剤が得られる。
20重量部の活性化合物を、例えばポリビニルピロリドンなどの10重量部の分散剤を加えて70重量部のシクロヘキサノンに溶解させる。水で希釈すると分散剤が得られ、それによって20%(重量基準)の活性化合物を含む製剤が得られる。
15重量部の活性化合物を、ドデシルベンゼンスルホン酸カルシウム及びヒマシ油エトキシレート(各場合で5重量部)を加えて80重量部のキシレンに溶解させる。水で希釈することで、乳濁液が得られ、それによって15%(重量基準)の活性化合物を含む製剤が得られる。
25重量部の活性化合物を、ドデシルベンゼンスルホン酸カルシウム及びヒマシ油エトキシレート(各場合で5重量部)を加えて35重量部のキシレンに溶解させる。この混合物を乳化器(例:Ultraturrax)によって30重量部の水に導入し、均一な乳濁液とする。水で希釈することで乳濁液が得られ、それによって25%(重量基準)の活性化合物を含む製剤が得られる。
撹拌ボールミルで、20重量部の活性化合物を10重量部の分散剤、湿展剤及び70重量部の水又は有機溶媒とともに粉砕して、微細な活性化合物懸濁液を得る。水で希釈することで、活性化合物の安定な懸濁液が得られ、それによって20%(重量基準)の活性化合物を含む製剤が得られる。
50重量部の活性化合物を50重量部の分散剤及び湿展剤を加えて微粉砕し、工業用機器(例えば押出器、噴霧塔、流動床)によって水分散性粒剤又は水溶性粒剤として製造する。水で希釈することで、活性化合物の安定な分散液又は溶液が得られ、それによって50%(重量基準)の活性化合物を含む製剤が得られる。
75重量部の活性化合物を25重量部の分散剤、湿展剤及びシリカゲルを加えてローター-ステーターミルで粉砕する。水で希釈することで、活性化合物の安定な分散液又は液剤が得られ、それによって75%(重量基準)の活性化合物を含む製剤が得られる。
撹拌ボールミルで、20重量部の活性化合物を、10重量部の分散剤、1重量部のゲル化剤/湿展剤及び70重量部の水若しくは有機溶媒を加えて粉砕して、微細な活性化合物懸濁液を得る。水で希釈することで、活性化合物の安定な懸濁液が得られ、それによって20%(重量基準)の活性化合物を含む製剤が得られる。
5重量部の活性化合物を微粉砕し、95重量部の微粉砕カオリンと十分に混和する。それによって5%(重量基準)の活性化合物を含むダスト製品が得られる。
0.5重量部の活性化合物を微粉砕し、95.5重量部の担体と混合することで、0.5%(重量基準)の活性化合物を含む製剤が得られる。現行の方法は、押し出し、噴霧乾燥又は流動床である。それによって、茎葉用途に未希釈施用される粒剤が得られる。
10重量部の活性化合物を90重量部の有機溶媒、例えばキシレンに溶かす。それによって、茎葉用途に未希釈施用される10%(重量基準)の活性化合物を含む製品が得られる。
アセフェート、アザメチホス、アジンホス-メチル、クロルピリホス、クロルピリホス−メチル、クロルフェンビンホス、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジスルホトン、エチオン、フェニトロチオン、フェンチオン、イソキサチオン、マラチオン、メタミドホス、メチダチオン、メチル-パラチオン、メビンホス、モノクロトホス、オキシデメトン-メチル、パラオクソン、パラチオン、フェントエート、ホサロン、ホスメット、ホスファミドン、ホレート、ホキシム、ピリミホス-メチル、プロフェノホス、プロチオホス、スルプロホス、テトラクロルビンホス、テルブホス、トリアゾホス、トリクロルホン;
A.2.カルバメート:
アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、カルバリル、カルボフラン、カルボスルファン、フェノキシカルブ、フラチオカルブ、メチオカルブ、メソミル、オキサミル、ピリミカルブ、プロポキスル、チオジカルブ、トリアザメート;
A.3.ピレスロイド:
アレスリン、ビフェントリン、シフルトリン、シハロトリン、シフェノトリン、シペルメトリン、α-シペルメトリン、β-シペルメトリン、ζ-シペルメトリン、デルタメトリン、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、イミプロトリン、λ-シハロトリン、ペルメトリン、プラレトリン、ピレトリンI及びII、レスメトリン、シラフルオフェン、τ-フルバリネート、テフルトリン、テトラメトリン、トラロメトリン、トランスフルトリン、プロフルトリン、ジメフルトリン;
A.4.成長調節剤:
(a)キチン合成阻害薬:ベンゾイル尿素類:クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、テフルベンズロン、トリフルムロン;ブプロフェジン、ジオフェノラン、ヘキシチアゾックス、エトキサゾール、クロフェンタジン(clofentazine);
(b)エクジソン拮抗薬:ハロフェノジド、メトキシフェノジド、テブフェノジド、アザジラクチン;
(c)幼若ホルモン様物質:ピリプロキシフェン、メトプレン、フェノキシカルブ;
(d)脂質生合成阻害薬:スピロジクロフェン、スピロメシフェン、スピロテトラマト;
A.5.ニコチン受容体作働薬/拮抗薬化合物:
クロチアニジン、ジノテフラン、イミダクロプリド、チアメトキサム、ニテンピラム、アセタミプリド、チアクロプリド;
下記式Γ1のチアゾール化合物:
アセトプロール、エンドスルファン、エチプロール、フィプロニル、バニリプロール(vaniliprole)、ピラフルプロール、ピリプロール、下記式Γ2の5-アミノ-1-(2,6-ジクロロ-4-トリフルオロメチル-フェニル)-4-トリフルオロメタンスルフィニル-1H-ピラゾール-3-カルボチオ酸アミド:
アバメクチン、エマメクチン、ミルベメクチン、レピメクチン(lepimectin)、スピノサド;
A.8.METI I化合物:
フェナザクイン(fenazaquin)、ピリダベン、テブフェンピラド、トルフェンピラド、フルフェネリム;
A.9.METI II及びIII化合物:
アセキノシル、フルアシプリム(fluacyprim)、ヒドラメチルノン;
A.10.脱共役剤化合物:
クロルフェナピル;
A.11.酸化的リン酸化阻害薬化合物:
シヘキサチン、ジアフェンチウロン、酸化フェンブタスズ、プロパルギット;
A.12.脱皮撹乱剤化合物:
シロマジン;
A.13.混合機能オキシダーゼ阻害薬化合物:
ピペロニルブトキシド;
A.14.ナトリウムチャンネル遮断薬化合物:
インドキサカルブ、メタフルミゾン、
A.15.各種:
ベンクロチアズ(benclothiaz)、ビフェナゼート、カルタップ、フロニカミド、ピリダリル、ピメトロジン、硫黄、チオシクラム、フルベンジアミド、シエノピラフェン、フルピラゾホス、シフルメトフェン、アミドフルメト、
式Γ3のアントラニルアミド化合物:
A1はCH3、Cl、Br、Iであり、
XはC-H、C-Cl、C-F又はNであり、
Y’はF、Cl又はBrであり、
Y”は水素、F、Cl又はCF3であり、
B1は水素、Cl、Br、I、CNであり、
B2はCl、Br、CF3、OCH2CF3、OCF2Hであり、
RBは水素、CH3又はCH(CH3)2である。〕;
並びに、JP 2002 284608号、WO 02/89579号、WO 02/90320号、WO 02/90321号、WO 04/06677号、WO 04/20399号、JP 2004 99597号、WO 05/68423号、WO 05/68432号又はWO 05/63694号に記載されているマロノニトリル化合物、特にはマロノニトリル化合物CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-オクタフルオロペンチル)-2-(3,3,3-トリフルオロプロピル)マロノニトリル)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H(2-(2,2,3,3,4,4,5,5,6,6,7,7-ドデカフルオロ−ヘプチル)-2-(3,3,3-トリフルオロ−プロピル)-マロノニトリル)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-テトラフルオロ-3-トリフルオロメチル-ブチル)-2-(3,3,3-トリフルオロ-プロピル)-マロノニトリル)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-ノナフルオロ-ヘキシル)-2-(3,3,3-トリフルオロ-プロピル)-マロノニトリル)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-ビス-(2,2,3,3,4,4,5,5-オクタフルオロ-ペンチル)-マロノニトリル)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-ノナフルオロ-ペンチル)-2-(3,3,3-トリフルオロ-プロピル)-マロノニトリル)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-ヘプタフルオロ-ブチル)-2-(2,2,3,3,4,4,5,5-オクタフルオロ-ペンチル)-マロノニトリル)及びCF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-オクタフルオロ-ペンチル)-2-(2,2,3,3,3-ペンタフルオロ-プロピル)-マロノニトリル)。
化合物IIAがトリフロキシストロビンであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表2
化合物IIAがアゾキシストロビンであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表3
化合物IIAがピラクロストロビンであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表4
化合物IIAがボスカリドであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表5
化合物IIAがメタラキシルであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
化合物IIAがメタラキシル-Mであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表7
化合物IIAがシプロコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表8
化合物IIAがエポキシコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表9
化合物IIAがフェンブコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表10
化合物IIAがフルキンコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
化合物IIAがフルトリアホールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表12
化合物IIAがイプコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表13
化合物IIAがメトコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表14
化合物IIAがプロピコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表15
化合物IIAがプロチオコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
化合物IIAがテブコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表17
化合物IIAがトリアジメノールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表18
化合物IIAがトリチコナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表19
化合物IIAがイマザリルであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表20
化合物IIAがプロクロラズであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
化合物IIAがカルベンダジムであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表22
化合物IIAがチアベンダゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表23
化合物IIAがエタボキサムであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表24
化合物IIAがヒメキサゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表25
化合物IIAがピリメタニルであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
化合物IIAがフルジオキソニルであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表27
化合物IIAがアルジモルフであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表28
化合物IIAがドデモルフであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表29
化合物IIAがフェンプロピモルフであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表30
化合物IIAがイプロジオンであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
表31
化合物IIAがカプタンであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表32
化合物IIAがフェノキサニルであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表33
化合物IIAがプロベナゾールであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表34
化合物IIAがマンコゼブであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表35
化合物IIAがメチラムであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
化合物IIAがチラムであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表37
化合物IIAがジラムであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表38
化合物IIAがグアザチンであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表39
化合物IIAがチオファネートメチルであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表40
化合物IIAがクロロタロニルであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物
表41
化合物IIAがメトラフェノンであり、各場合における化合物IIB1及びIIB2の組み合わせが表Qの列に対応する混合物。
以下の製造手順の全ては、WO 01/30760号に記載された手順に従って70℃〜35℃の温度でモノクロロベンゼン/エタノール(結晶化開始のエタノールの重量%:13%)の溶媒混合物から生成物の最終結晶化を行って得られた固体フィプロニルの2つのサンプルを出発物質として用いて実施した。X線粉末回折図試験において、この固体形態は、いくつかの結晶変態の混合物の結晶性フィプロニルであると証明された。この混合物は、結晶変態I及び結晶変態Vからなると特性決定され、同時係属中の特許出願において初めて特定され、記載された。変態I及び変態Vの単結晶データからシミュレーションしたX線粉末回折図パターンを用いたTopasプログラムによる最小二乗精密化は、これら2つの実施例サンプルにおいて、形態Iの割合が30%〜70%で変動することを示す。2つのサンプルのX線粉末回折図を図3に示す。
化学純度約96重量%の結晶性フィプロニル1 gを75〜81℃において還流しながら25gのアセトニトリルに溶解した。この溶液をこの温度に維持し、溶媒を穏やかな不活性N2ガス流を用いてゆっくりとエバポレートした。溶媒が蒸発するように3日間放置し、その後、サンプルを20〜25℃に冷却し、得られた乾燥結晶物質を減圧を用いて残留溶媒からろ紙上にろ別した。結晶化収量>95%、融点:202℃。得られた物質は、以下の表2に示す反射を有する図1に示すX線粉末回折図を有した。
化学純度約96重量%の結晶性フィプロニル0.5 gを丸底フラスコ中で138〜142℃において10mlのDMSOに溶解した。この溶液をこの温度に維持し、溶媒を穏やかな不活性N2ガス流を用いてゆっくりとエバポレートした。溶媒が蒸発するように約15時間放置し、その後、サンプルを20〜25℃に冷却し、得られた結晶物質を減圧を用いて残留溶媒からろ紙上にろ別した。結晶化収量>85%、融点:202.5℃。得られた物質は、以下の表2に示す反射を有する図1に示すX線粉末回折図を有した。
図1に示したX線粉末回折図の写真は、25℃でのCu-Kα放射線を用いて0.02°ずつ増加させながら2θ=2°〜60°の範囲の反射配置でシーメンス(Siemens)D-5000回折計(製造者:ブルカー(Bruker)AXS)を用いて取得した。
Claims (28)
- 30℃でのX線粉末回折図において、下記の反射:
(1)d=8.55±0.1Å
(2)d=7.94±0.07Å
(3)d=6.78±0.05Å
(4)d=5.43±0.05Å
(5)d=4.35±0.05Å
(6)d=2.83±0.03Å
のうちの少なくとも5つを示すフィプロニルの結晶変態V。 - 201〜203℃の範囲の融点を有する、請求項1記載の結晶変態V。
- 中心対称性の空間群P-1を有する三斜晶系で存在する、請求項1又は2記載の結晶変態V。
- 少なくとも98重量%のフィプロニル含有量を有する、請求項1〜3のいずれか1項に記載の結晶変態V。
- 請求項1〜4のいずれか1項に記載の結晶変態Vと、結晶変態Vとは異なる形態のフィプロニルとを含む固体フィプロニル。
- 請求項1〜4のいずれか1項に記載の結晶変態Vを少なくとも85重量%で含む、請求項5記載の固体フィプロニル。
- (i)結晶変態Vとは異なる固体形態のフィプロニルの、100℃〜150℃の温度のジメチルスルホキシド又は60℃〜81℃の温度のアセトニトリルから選択される溶媒S中の溶液を調製するステップ;
(ii)溶液からフィプロニルの結晶化を行うステップ;並びに
(iii)得られた沈澱を単離するステップ
を含む、請求項1〜4のいずれか1項に記載の結晶変態Vの製造方法。 - 溶媒Sが、130℃〜150℃の温度のジメチルスルホキシド又は70℃〜81℃の温度のアセトニトリルである、請求項7記載の方法。
- 溶媒Sがアセトニトリルである、請求項7又は8記載の方法。
- 溶媒Sがジメチルスルホキシドである、請求項7又は8記載の方法。
- ステップ(ii)において、フィプロニルの結晶化を、ステップ(i)で得られた溶液の濃縮により行う、請求項6〜10のいずれか1項に記載の方法。
- ステップ(ii)を、請求項1〜4のいずれか1項に記載の結晶変態Vのシード結晶の存在下で行う、請求項6〜11のいずれか1項に記載の方法。
- 活性成分として、請求項1〜4のいずれか1項に記載の結晶変態V、及び1以上の殺虫性又は殺寄生虫性化合物を含む、相乗的な殺虫又は殺寄生虫混合物。
- 請求項1〜4のいずれか1項に記載の結晶変態V又は請求項13記載の混合物、並びに殺虫又は殺寄生虫のために許容される担体及び/又は補助剤を含む、殺虫又は殺寄生虫組成物。
- 水系懸濁液濃縮物の形態である、請求項14記載の組成物。
- 水分散性粒剤の形態である、請求項14記載の組成物。
- 水分散性粉剤の形態である、請求項14記載の組成物。
- 害虫防除のための、請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物の使用。
- 害虫又はその食料源、生息場所、繁殖地若しくはその場所を、殺虫有効量の請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物と接触させるステップを含む、害虫の防除方法。
- 植物の葉又は茎に、殺虫有効量の請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物を施用するステップを含む、害虫による侵入及び攻撃から植物を保護する方法。
- 請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物を5g/ha〜2000g/haの量で施用する、請求項19又は20記載の方法。
- 前記害虫が、昆虫、クモ形類又は植物線虫である、請求項18記載の使用又は請求項19〜21のいずれか1項に記載の方法。
- 殺虫有効量の、請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物と種子を接触させるステップを含む、種子の保護方法。
- 請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物を0.1g〜10kg/種子100kgの量で施用する、請求項23記載の方法。
- 請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物を0.1g〜10kg/種子100kgの量で含む種子。
- 動物の体内及び体表における寄生虫を駆除するための、請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物の使用。
- 殺寄生虫有効量の請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物を、動物に対して経口、局所若しくは非経口的に投与又は施用するステップを含む、寄生虫による侵入又は感染に対して動物を治療、制御、予防又は保護する方法。
- 殺寄生虫有効量の請求項1〜4のいずれか1項に記載の結晶変態V又は請求項5若しくは6記載の固体フィプロニル又は請求項13記載の混合物又は請求項14〜17のいずれか1項に記載の組成物を含む、寄生虫による侵入又は感染に対して動物を治療、制御、予防又は保護するための組成物の製造方法。
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JP2014139189A (ja) * | 2006-11-10 | 2014-07-31 | Basf Se | フィプロニルの結晶変態 |
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JP5396085B2 (ja) | 2005-12-14 | 2014-01-22 | マクテシム・ケミカル・ワークス・リミテツド | 5−アミノ−1−[2,6−ジクロロ−4−(トリフルオロメチル)フェニル]−4−[(トリフルオロメチル)スルフィニル]−1h−ピラゾール−3−カルボニトリルの多形および非晶形 |
SI2083629T2 (sl) | 2006-11-10 | 2015-03-31 | Basf Se | Kristalna modifikacija fipronila |
UA110598C2 (uk) | 2006-11-10 | 2016-01-25 | Басф Се | Спосіб одержання кристалічної модифікації фіпронілу |
AU2007316639B2 (en) | 2006-11-10 | 2012-12-20 | Basf Se | Crystalline modification of fipronil |
CN102160207A (zh) * | 2008-09-19 | 2011-08-17 | 巴斯夫欧洲公司 | 二苯并四苯基二茚并(1,2,3-cd:1’,2’,3’-lm)苝在有机太阳能电池中的用途 |
CN103313604B (zh) | 2011-01-14 | 2016-03-02 | K·H·伽达 | [5-氨基-1-(2,6-二氯-4-三氟甲苯基)-3-腈-4-三氟甲基亚磺酰基吡唑]中的多晶体 |
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- 2007-11-05 CN CN200780044898.0A patent/CN101557712B/zh active Active
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JP2014139189A (ja) * | 2006-11-10 | 2014-07-31 | Basf Se | フィプロニルの結晶変態 |
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IL198265A0 (en) | 2009-12-24 |
CA2667112C (en) | 2015-08-11 |
UA95991C2 (ru) | 2011-09-26 |
ZA200903972B (en) | 2012-02-29 |
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AU2007316640B2 (en) | 2012-11-29 |
EA200900630A1 (ru) | 2009-12-30 |
JP5931322B2 (ja) | 2016-06-08 |
NZ576592A (en) | 2012-06-29 |
EP2083628A1 (en) | 2009-08-05 |
JP2014139189A (ja) | 2014-07-31 |
US20100041727A1 (en) | 2010-02-18 |
IL198265A (en) | 2017-08-31 |
EA018341B1 (ru) | 2013-07-30 |
US8188136B2 (en) | 2012-05-29 |
WO2008055883A1 (en) | 2008-05-15 |
MA30928B1 (fr) | 2009-11-02 |
US9913473B2 (en) | 2018-03-13 |
KR101540122B1 (ko) | 2015-07-28 |
CN101557712B (zh) | 2014-03-12 |
TW200829168A (en) | 2008-07-16 |
AR063650A1 (es) | 2009-02-04 |
AU2007316640A1 (en) | 2008-05-15 |
TWI434652B (zh) | 2014-04-21 |
BRPI0718720A2 (pt) | 2013-12-03 |
MX2009004486A (es) | 2009-05-12 |
CN101557712A (zh) | 2009-10-14 |
CA2667112A1 (en) | 2008-05-15 |
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