JP5923040B2 - 繁殖体コーティングのためのアントラニルジアミド組成物 - Google Patents
繁殖体コーティングのためのアントラニルジアミド組成物 Download PDFInfo
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- JP5923040B2 JP5923040B2 JP2012528085A JP2012528085A JP5923040B2 JP 5923040 B2 JP5923040 B2 JP 5923040B2 JP 2012528085 A JP2012528085 A JP 2012528085A JP 2012528085 A JP2012528085 A JP 2012528085A JP 5923040 B2 JP5923040 B2 JP 5923040B2
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Classifications
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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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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Description
(a)約9〜約91重量%の1種以上のアントラニルジアミド殺虫剤と、
(b)20℃にて少なくとも約5重量%の水溶性、少なくとも約5の親水親油バランス値、および約1500〜約20000ダルトンの範囲の平均分子量を有する約9〜約91重量%の非イオン性エチレンオキシド−プロピレンオキシドブロックコポリマー構成成分と
を含み、ここで、構成成分(b)と構成成分(a)の重量比は約1:10〜約10:1である、組成物である。
(a)約9〜約91重量%の1種以上のアントラニルジアミド殺虫剤と;
(b)20℃にて少なくとも約5重量%の水溶性、少なくとも約5の親水親油バランス値、および約1500〜約20000ダルトンの範囲の平均分子量を有する約9〜約91重量%の非イオン性エチレンオキシド−プロピレンオキシド(EO/PO)ブロックコポリマー構成成分と
を含み、ここで、構成成分(b)と構成成分(a)の重量比は約1:10〜約10:1である、組成物。
Xは、N、CF、CCl、CBrまたはCIであり;
R1は、CH3、Cl、BrまたはFであり;
R2は、H、F、Cl、Brまたは−CNであり;
R3は、F、Cl、Br、C1〜C4ハロアルキルまたはC1〜C4ハロアルコキシであり;
R4aは、H、C1〜C4アルキル、シクロプロピルメチルまたは1−シクロプロピルエチルであり;
R4bは、HまたはCH3であり;
R5は、H、F、ClまたはBrであり;そして
R6は、H、F、ClまたはBrである、
組成物。
(a)約9〜約91重量%の1種以上のアントラニルジアミド殺虫剤と、
(b)20℃にて少なくとも約5重量%の水溶性、少なくとも約5の親水親油バランス値、および約1500〜約20000ダルトンの範囲の平均分子量を有する約9〜約91重量%の非イオン性エチレンオキシド−プロピレンオキシドブロックコポリマー構成成分と
を含み、ここで、構成成分(b)と構成成分(a)の重量比は約1:10〜約10:1である、組成物である。
メチル−6−[(メチルアミノ)カルボニル]フェニル]−1H−ピラゾール−5−カルボキサミドおよび提唱された慣用名シアントラニリプロールを有しており、殺虫有効成分として、DuPontによりCYAZYPYRとして商標登録されている。国際公開第2006/062978号パンフレットの実施例15に開示されているように、シアントラニリプロールは、177〜181℃または217〜219℃で融解する固体(すなわち、2つの異なる多形)の形態にある。両方の多形が、本組成物および方法に好適である。
流動床系を、以下の実施例に記載された組成物で種子をコーティングするために使用した。水性組成物を吹付ける間、種子を熱空気の垂直流で吹き上がらせた。この熱空気が、種子に塗布された組成物から水担体を蒸発させた。コーティング系に導入される組成物の量は、有効成分(例えば、化合物1または化合物2)の示された目標塗布量を種子に送達できるように、塗布機から出て失われた、または種子以外の領域をコーティングして失われた材料を補うように調整した。
植物葉は、Geno/Grinder 2000ビーズビーターホモジナイザー(SPEX CertiPrep,Metuchen,NJ,USA)を用いて細断し、次いでアセトニトリル(約5mL/g葉組織)を加えた。この混合物を、Geno/Grinderホモジナイザーを用いて1分間さらに振盪し、次いで遠心分離した。アセトニトリル抽出物の上清を、Waters(Milford,MA USA)のAlliance HT2795クロマトグラフおよびZorbax SB C18(2.1×50mm、5μm)カラムを用い、0.1%(体積/体積)のギ酸を含有する水とアセトニトリルとの混合物で溶離し、Waters Quattro Micro API質量分析器によりエレクトロスプレーイオン化(ESI+)を用いて検出する、タンデム質量分析検出を伴う高速液体クロマトグラフィ(HPLC/MS/MS)により分析した。化合物1および化合物2の標準液を、アセトニトリルまたはテトラヒドロフラン中の化合物1または化合物2の測定量の原液を、処理していない種子から生育させた植物からの葉のアセトニトリル抽出物に加えることにより調製した。
化合物1およびPLURONIC非イオン性EO/POブロックコポリマーを含む水性組成物を、表3に列挙した相対量の成分から調製した。各実施例組成物について、PLURONIC化合物を水に溶かし、この水溶液を他の成分に加え、次いで、結果として生じた混合物をミル粉砕した。実施例1〜6の組成物についてのメジアン粒径を、Malvern Mastersizer測定装置を用いて測定した。
実施例7〜12は、化合物1および非イオン性EO/POブロックコポリマーを含む組成物を調製するためのさらなる方法を例示するものである。実施例7〜9において使用された化合物1は、微粉の形態のものであった。実施例7〜12に記載された組成物を、(1A)殺真菌剤製品のMAXIM 4FS(40.3%フルジオキソニル)とAPRON XL(33.3%メフェノキサム)との重量で1:3の混合物、および(2)着色剤Acid Blue Dyeと混合し、次いで結果として生じた組成物を、種子100g(100gは約23,400個の種子に相当)当たり0.6gの化合物1、0.067mLの殺真菌剤混合物(1A)および0.033gの着色剤(2)の塗布量でカノーラ種子をコーティングするために使用した。コーティングした種子を播種し、生育チャンバ内で生育させ、第二葉を、実施例1〜6について記載した通りに分析した。
化合物1(2g)を、水(14g)に溶解させたPLURONIC F108(2g)の溶液に加えた。この混合物を、250分間超音波浴に入れ、次いで16日間攪拌し、最後に14日間放置した。結果として生じた組成物を、殺真菌剤混合物(1A)および着色剤(2)と混合し、カノーラ種子をコーティングするために使用し、これを播種し、第二葉を上記の通りに分析した。分析により、カノーラ葉1g当たり0.24μgの化合物1の濃度が示された。
PLURONIC F108(10.0g)を、水(80g)に溶解させた。この溶液の一部(12.0g)を、化合物1(5.0g)と合わせ、したがって、約1:3.75の重量比のPLURONIC F108と化合物1を得た。この混合物を18日間攪拌し、次いで4日間放置した。結果として生じた組成物を、殺真菌剤混合物(1A)および着色剤(2)と混合し、カノーラ種子をコーティングするために使用し、これを播種し、第二葉を上記の通りに分析した。分析により、カノーラ葉1g当たり0.12μgの化合物1の濃度が示された。
実施例8のPLURONIC F108水溶液の一部(1.91g)を、化合物1(0.702g)と混合し、したがって、約1:3.3の重量比のPLURONIC F108と化合物1を得た。この組成物を約1分間だけ混合してから、殺真菌剤混合物(1A)および着色剤(2)とさらに混合し、カノーラ種子をコーティングするために使用し、これを播種し、第二葉を上記の通りに分析した。分析により、カノーラ葉1g当たり0.12μgの化合物1の濃度が示された。
化合物1(2.8g)およびPLURONIC P85(0.90g)を、30重量%のエタノールおよび70重量%のジクロロメタンからなる溶液70mLに溶解させた。溶媒を、ロータリーエバポレーションにより除去した。その残留物を水と混合し、次いで殺真菌剤混合物(1A)および着色剤(2)と混合し、カノーラ種子をコーティングするために使用し、これを播種し、第二葉を上記の通りに分析した。分析により、カノーラ葉1g当たり0.12μgの化合物1の濃度が示された。
化合物1(2g)およびPLURONIC F68(2g)を、N−メチル−2−ピロリドン(10mL)に溶解させた。この溶液をジエチルエーテル(200mL)に加えると、固体沈殿物の形成をもたらした。この固体を回収し、ジエチルエーテルで洗浄し、乾燥させた。この固体を水中に懸濁させ、この懸濁液を殺真菌剤混合物(1A)および着色剤(2)と混合し、カノーラ種子をコーティングするために使用し、これを播種し、第二葉を上記の通りに分析した。分析により、カノーラ葉1g当たり0.12μgの化合物1の濃度が示された。
化合物1(3.00g)およびPLURONIC P85(3.00g)を、N−メチル−2−ピロリドン(15mL)に溶解させた。この溶液を、セルロース系透析チューブ(分子量カットオフ約1000ダルトン、長さ14cm)に移した。このチューブの末端を、透析のための内容物を保持するようにクランプで締めた。このチューブを、脱イオン水(約3.8L)に浸漬させ、3日の間に3回交換した。結果として生じた水性スラリーを、殺真菌剤混合物(1A)および着色剤(2)と混合し、カノーラ種子をコーティングするために使用し、これを播種し、第二葉を上記の通りに分析した。分析により、カノーラ葉1g当たり0.28μgの化合物1の濃度が示された。
実施例1の組成物を、(1B)殺真菌剤製品のMAXIM 4FSとAPRON XLとの重量で1.2:3の混合物、および(2)着色剤Acid Blue Dyeと混合し、次いで結果として生じた組成物を、種子100g(100gは約442個の種子に相当)当たり0.11gの化合物1、0.02mLの殺真菌剤混合物(1B)および0.05gの着色剤(2)の塗布量でトウモロコシ種子をコーティングするために使用した。この処理剤は、化合物1およびPLURONIC F68のそれぞれを、種子1個当たり平均約0.25mg提供した。
実施例3の組成物を、殺真菌剤混合物(1B)および着色剤(2)と混合し、トウモロコシ種子をコーティングするために使用し、これを播種し、第三葉を、実施例13に記載した通りに分析した。この処理剤は、種子1個当たり平均約0.25mgの化合物1および0.075mgのPLURONIC F98を提供した。第三葉の分析により、トウモロコシ葉1g当たり1.0μgの化合物1の濃度が示された。
10重量%のPLURONIC F108、33.6重量%の化合物1、48.8重量%の水、0.5重量%のACTI−GEL 208、0.2重量%のRHODOPOL 23、0.3重量%のDOW 2−3101、0.05重量%のLEGEND MK、1.5重量%のプロピレングリコール、および3重量%のAGNIQUE GLY 96を含有する組成物を、実施例1〜6の方法に従って調製した。メジアン粒径は、0.56μmと測定された。この組成物を、殺真菌剤混合物(1B)および着色剤(2)と混合し、トウモロコシ種子をコーティングするために使用し、これを播種し、第三葉を、実施例13に記載した通りに分析した。この処理剤は、種子1個当たり平均約0.25mgの化合物1および0.074mgのPLURONIC F108を提供した。第三葉の分析により、トウモロコシ葉1g当たり1.0μgの化合物1の濃度が示された。
化合物2およびPLURONIC非イオン性EO/POブロックコポリマーを含む水性組成物を、表3に列挙した相対量の成分から調製した。各実施例組成物について、PLURONIC化合物を水に溶かし、この水溶液を他の成分に加え、次いで、結果として生じた混合物をミル粉砕した。実施例18および19の組成物についてのメジアン粒径を、Malvern Mastersizer測定装置を用いて測定した。
化合物2およびPLURONIC非イオン性EO/POブロックコポリマーを含む水性組成物を、まずPLURONIC(25g)を水(75g)と混合し、次いでその水性PLURONIC混合物の一部(20g)を粉末の形態の化合物2(5g)と混合することによって調製した。実施例21、22および23の組成物におけるメジアン粒径は、それぞれ0.84、0.86および0.80μmと測定された。実施例21〜23ならびに比較例BおよびCの組成物を、(1B)殺真菌剤製品のMAXIM F4SとAPRON XLとの1.2:3の重量の混合物および(2)着色剤のAcid Blue Dyeと混合し、次いで結果として生じた組成物を、種子100g(100gは約442個の種子に相当)当たり0.11gの化合物2、0.02mLの殺真菌剤混合物(1B)および0.05gの着色剤(2)の塗布量でトウモロコシ種子をコーティングするために使用した。この処理剤は、種子1個当たり平均約0.25mgの化合物2を提供した。コーティングされたトウモロコシ種子を、実施例13について記載した通りに、各ポットに4個の種子を含有する少なくとも5つのポットに播種し、生育チャンバ内で生育させた。播種から13〜14日後、各ポットから、第三葉を3つのトウモロコシ植物の稈から切り取り、分析のために同じバイアルに合わせた。
Claims (11)
- 殺虫組成物であって、前記組成物の総質量に基づき、
(a)9〜91質量%の1種またはそれ以上のアントラニルジアミド殺虫剤と、
(b)20℃にて少なくとも5質量%の水溶性、少なくとも5の親水親油バランス値、および3000〜20000ダルトンの範囲の平均分子量を有する9〜91質量%のポロキサマー、逆ポロキサマー、ポロキサミンおよび逆ポロキサミンから選択される、非イオン性エチレンオキシド−プロピレンオキシドブロックコポリマー構成成分と
を含み、ここで、構成成分(b)と構成成分(a)の質量比は1:5〜10:1である、組成物。 - 構成成分(a)が、式1:
Xは、N、CF、CCl、CBrまたはCIであり;
R1は、CH3、Cl、BrまたはFであり;
R2は、H、F、Cl、Brまたは−CNであり;
R3は、F、Cl、Br、C1〜C4ハロアルキルまたはC1〜C4ハロアルコキシであり
;
R4aは、H、C1〜C4アルキル、シクロプロピルメチルまたは1−シクロプロピルエチルであり;
R4bは、HまたはCH3であり;
R5は、H、F、ClまたはBrであり;そして
R6は、H、F、ClまたはBrである、
請求項1に記載の組成物。 - 構成成分(a)が、XがNであり;R1がCH3であり;R2がClまたは−CNであり;R3がBrであり;R4aがCH3であり;R4bがHであり;R5がClであり;そしてR6がHである、式1の化合物およびその塩から選択される、請求項2に記載の組成物。
- 構成成分(b)が、前記組成物の少なくとも15質量%である、請求項1〜3のいずれか1項に記載の組成物。
- 構成成分(b)が、ポロキサマーおよびポロキサミンから選択される、請求項1〜4のいずれか1項に記載の組成物。
- 構成成分(b)が、ポロキサマーから選択される、請求項5に記載の組成物。
- 少なくとも1種の殺真菌剤またはアントラニルジアミド殺虫剤以外の殺虫剤をさらに含む、請求項1〜6のいずれか1項に記載の組成物。
- 殺虫有効量の請求項1〜7のいずれか1項に記載の組成物でコーティングされた、屈地性繁殖体。
- 種子である、請求項8に記載の屈地性繁殖体。
- 5〜80質量%の請求項1〜7のいずれか1項に記載の組成物および20〜95質量%の揮発性水性液体キャリアからなる、液体組成物。
- 屈地性繁殖体およびそれに由来する植物を植食性昆虫害虫から保護するための方法であって、殺虫有効量の請求項10に記載の液体組成物で前記繁殖体をコーティングする工程と、次いで前記組成物の前記揮発性水性液体キャリアを蒸発させる工程とを包含する、方法。
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