JP2021527105A - チオシクラム塩基及び塩の調製プロセス - Google Patents
チオシクラム塩基及び塩の調製プロセス Download PDFInfo
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- 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
- A01N43/02—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
- A01N43/24—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 two or more hetero atoms
- A01N43/32—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 two or more hetero atoms six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D341/00—Heterocyclic compounds containing rings having three or more sulfur atoms as the only ring hetero atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本出願は、米国特許法第119条(e)の下で、2018年6月13日出願の米国特許仮出願第62/684,530号の利益を主張するものであり、当該仮出願は、「MANUFACTURING METHOD FOR AND INSECTICIDAL COMPOSITIONS COMPRISING THIOCYCLAM HYDROCHLORIDE」と題する2016年9月19日出願の、本願と同じ譲受人に譲渡された係属中の米国特許出願第15/268,734号に関連する。
本発明が一般に関連する技術分野は、殺虫性組成物である。
Na2S・9H2O(15.3g)の水性塩溶液を、4時間かけて温度を−15℃〜−18℃に維持しながら、モノスルタップ(25g)、水酸化ナトリウム(3.16g)、及びトルエン/塩溶液の撹拌混合物に添加した。反応混合物を、完全になるまで−15℃で撹拌し、その後濾過して無機塩を除去した。ケークをトルエンで洗浄し、洗浄液を濾過液と組み合わせた。相分離させ、トルエン溶液を水で洗浄した後、ブラインで洗浄し、硫酸ナトリウムで乾燥させた。2Mのエーテル性塩酸(50mL)を添加し、混合物を1時間撹拌した。形成した固形物を濾過により回収し、氷冷MTBEで洗浄し、乾燥させて、0.22%の残留トルエンを含む、収率76%(12.4g)及び純度98.3%のチオシクラム塩酸塩を得た。しかしながら、実験室環境外、例えば商業環境において、エーテル性塩酸を使用することは非常に困難であろう。
モノスルタップ(450g)、水酸化ナトリウム(51.3g)及び塩溶液の混合物を、トルエンを含有する反応器に−15℃〜−20℃で添加した。Na2S・9H2O(308g)の水性塩溶液をバッチに4時間かけて添加し、温度を−15℃に維持した。反応混合物を、完全になるまで−15℃で撹拌した後、相分離させた。水性処理の後、有機層を硫酸マグネシウムで乾燥させ、2Mのエーテル性塩酸(710mL)を加えた。混合物を1時間撹拌した後、形成した固形物を濾過により回収した。ケークをトルエンで洗浄し、乾燥させて、0.55%の残留トルエンを含む、収率68%(214g)及び純度94.2%のチオシクラム塩酸塩を得た。しかしながら、実験室環境外、例えば商業環境において、エーテル性塩酸を使用することは非常に困難であろう。
Na2S・9H2O(239.5g)の水性塩溶液を、3.5時間かけて温度を−16℃〜−18℃に維持しながら、モノスルタップ(350g)、水酸化ナトリウム(39.9g)、及びトルエン/塩溶液の撹拌混合物に添加した。反応混合物を、完全になるまで−16℃〜−18℃で撹拌し、その後濾過して無機塩を除去した。ケークをトルエンで洗浄し、洗浄液を濾過液と組み合わせた。相分離させ、トルエン溶液を水で洗浄した後、ブラインで洗浄し、硫酸ナトリウムで乾燥させた。2Mのエーテル性塩酸(680mL)をバッチに30分かけて添加し、混合物を1時間撹拌した。形成された固形物を濾過により回収し、氷冷MTBEで洗浄し、乾燥させて、0.05%の残留トルエンを含む、収率33%(76.1g)及び純度95.2%のチオシクラム塩酸塩を得た。
Na2S・水和物(53.05g)の水性塩溶液を、1.5時間かけてバッチ温度を−15℃未満に維持しながら、モノスルタップ(100g)、水酸化ナトリウム(10.8g)、及びトルエン/塩溶液/イソプロパノールの撹拌混合物に添加した。反応混合物を、完全になるまで−20℃〜−15℃で撹拌した。CELITE材料(100g)を混合物に投入し、撹拌を−20℃〜−15℃で10分間継続した。バッチをCELITE材料のパッドを通して濾過し、濾過ケークをトルエンで洗浄した。合わせた濾液を分離し、有機物を水で洗浄した後、ブラインで洗浄し、硫酸ナトリウムで乾燥させた。イソプロパノール中2Mの塩酸(213mL)をバッチに30分かけて添加し、混合物を1時間撹拌した。形成された固形物を濾過により回収し、トルエンで洗浄し、乾燥させて、収率80%(50.0g)及び純度97.6%のチオシクラム塩酸塩を得た。
Na2S・水和物(26.5g)の水性塩溶液を、1.5時間かけてバッチ温度を−15℃未満に維持しながら、モノスルタップ(50g)、水酸化ナトリウム(5.4g)、及びトルエン/塩溶液/イソプロパノールの撹拌混合物に添加した。反応混合物を、完全になるまで−20℃〜−15℃で撹拌した。CELITE材料(50g)を混合物に投入し、撹拌を−20℃〜−15℃で10分間継続した。バッチをCELITE材料のパッドを通して濾過し、濾過ケークをトルエンで洗浄した。合わせた濾液を分離し、有機物を水で洗浄した後、ブラインで洗浄し、硫酸ナトリウムで乾燥させた。イソプロパノール中5Mの塩酸(4.2mL)をバッチに30分かけて添加し、混合物を1時間撹拌した。形成された固形物を濾過により回収し、トルエンで洗浄し、乾燥させて、収率82%(25.5g)及び純度97.9%のチオシクラム塩酸塩を得た。
Na2S・水和物(53.05g)の水性塩溶液を、1.5時間かけてバッチ温度を−15℃未満に維持しながら、モノスルタップ(100g)、水酸化ナトリウム(10.8g)、及びトルエン/塩溶液/イソプロパノールの撹拌混合物に添加した。反応混合物を、完全になるまで−20〜−15℃で撹拌した。CELITE材料(100g)を混合物に投入し、撹拌を−20〜−15℃で10分間継続した。バッチをCELITE材料のパッドを通して濾過し、濾過ケークをトルエンで洗浄した。合わせた濾液を分離し、有機物を水で洗浄した後、ブラインで洗浄し、硫酸ナトリウムで乾燥させた。HClガスをバッチを通して2.5時間かけてバブリングし、得られた混合物を16時間撹拌した。形成された固形物を濾過により回収し、トルエンで洗浄し、乾燥させて、収率88%(56.0g)及び純度95.4%のチオシクラム塩酸塩を得た。
溶液A:モノスルタップ(200g)及び水酸化ナトリウム(21.6g)を塩溶液に溶解し、溶液を濾過して微粒子を除去した後、0℃に冷却した。
コドリンガ(Coding moth)、Cydia pomonella−新生(onate)幼虫
餌への組み込みによるバイオアッセイ;
処理2日後の死亡率評価。
a.i.は活性成分を指す
大豆シャクトリムシ(Soybean looper)、Chrysodeixis includens−第3幼虫期
餌表面への組み込みによるバイオアッセイ
処理3日後の死亡率評価
a.i.は活性成分を指す
アブラムシ、Myzus persicae−幼虫
IRAC n°019法に基づく試験、適用法を適応
植物:大根
幼虫を入れたペトリ皿にブームスプレーヤー装置を用いて適用
塗布3日及び4日後の死亡率を評価
a.i.は活性成分を指す
コナジラミ、Trialeurodes vaporarium−幼虫
IRAC n°015法に基づく試験、ステージ及び適用法を適応
植物:豆
適用:幼虫を入れたペトリ皿にブームスプレーヤー装置を用いる
塗布7日、9日及び14日後の死亡率を評価
a.i.は活性成分を指す
Claims (17)
- N,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩の製造方法であって、
(a)チオ硫酸S,S’−[2−(ジメチルアミノ)トリメチレン]エステル一ナトリウム塩と水酸化ナトリウムとの混合物を提供する工程と、
(b)チオ硫酸S,S’−[2−(ジメチルアミノ)トリメチレン]エステル一ナトリウム塩と水酸化ナトリウムとの前記混合物に水性塩溶液を添加する工程と、
を含み、
前記N,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩の収率が、工程b)に珪藻土を加え、前記珪藻土と前記工程b)の組成物との混合物を形成し、前記混合物を珪藻土媒体を通して濾過することによって増加する、方法。 - (c)前記混合物の相を分離する工程と、
(d)濾過を使用して前記混合物から固形物を回収する工程と、
(e)前記固形物を有機溶媒で洗浄する工程と、
(f)前記固形物を乾燥させる工程と、を追加的に含み、
前記乾燥固形物が、N,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩を含む、請求項1に記載の方法。 - 前記有機溶媒が、メチル−t−ブチルエーテル、トルエン、イソプロパノール、又はこれらの混合物を含む、請求項1に記載の方法。
- 前記水性塩溶液が塩化ナトリウムを含む、請求項1に記載の方法。
- 工程b)中の温度が−10℃〜−25℃である、請求項1に記載の方法。
- N,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩の純度が90%超である、請求項1に記載の方法。
- N,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩の純度が95%超である、請求項6に記載の方法。
- 90%超の純度を有するN,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩。
- 90%超の純度を有するN,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩を含む殺虫性組成物であって、90%超の純度を有するN,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩の有効量が、90%未満の純度を有する化合物と比較して実質的に低減される、殺虫性組成物。
- ある場所で害虫を防除する方法であって、前記方法が、約1〜2000gの量の90%超の純度を有するN,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩を含む組成物を前記場所に適用することを含み、90%超の純度を有するN,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩の有効量が、90%未満の純度を有する化合物と比較して実質的に低減される、方法。
- 前記組成物が、適用前に水で最大約600倍以上、好ましくは100倍以上、より好ましくは40倍以上に希釈される、請求項10に記載の方法。
- 前記組成物が、約60〜約600L/haに希釈後の総適用量が、約0.1〜約30リットル/ヘクタールである、請求項10に記載の方法。
- 90%超の純度を有するN,N−ジメチル−1,2,3−トリチアン−5−イルアミン塩酸塩の殺虫剤としての使用。
- 前記化合物の純度が100%のとき、前記化合物のLC50が約2.0〜約3.50μg a.i./mLであるか、又は前記化合物のLC90が約8.0〜約15.00μg a.i./mLである、請求項13に記載の使用。
- 前記化合物の純度が100%のとき、前記化合物のLC50が約6.5〜約13.00μg a.i./mLであるか、又は前記化合物のLC90が約100.0〜約550.0μg a.i./mLである、請求項13に記載の使用。
- 前記化合物の純度が100%のとき、前記化合物のLC50が約12.0g a.i./haであるか、又は前記化合物のLC90が約30.00g a.i./haである、請求項13に記載の使用。
- 前記化合物の純度が100%のとき、前記化合物のLC50が約7.0〜約8.50g a.i./haであるか、又は前記化合物のLC90が約2.0〜約30.00g a.i./mLである、請求項13に記載の使用。
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化学工学協会, 化学工学便覧, vol. 第3版 第13刷, JPN7023002356, 10 April 1977 (1977-04-10), pages 938 - 941, ISSN: 0005092145 * |
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