JP5818073B2 - O−エチルS−n−プロピル(E)−[2−(シアノイミノ)−3−エチルイミダゾリジン−1−イル]ホスホノチオアートの製造方法 - Google Patents
O−エチルS−n−プロピル(E)−[2−(シアノイミノ)−3−エチルイミダゾリジン−1−イル]ホスホノチオアートの製造方法 Download PDFInfo
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- JP5818073B2 JP5818073B2 JP2011156572A JP2011156572A JP5818073B2 JP 5818073 B2 JP5818073 B2 JP 5818073B2 JP 2011156572 A JP2011156572 A JP 2011156572A JP 2011156572 A JP2011156572 A JP 2011156572A JP 5818073 B2 JP5818073 B2 JP 5818073B2
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- ethyl
- cyanoimino
- propyl
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- phosphonothioate
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- 238000000034 method Methods 0.000 title description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- FJOWWXPCMHSECA-UHFFFAOYSA-N (1-ethyl-4,5-dihydroimidazol-2-yl)cyanamide Chemical compound CCN1CCNC1=NC#N FJOWWXPCMHSECA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CTXTURKLZDCOPJ-PKNBQFBNSA-N CCCOP(ON(CCN1CC)/C\1=N/C#N)=S Chemical compound CCCOP(ON(CCN1CC)/C\1=N/C#N)=S CTXTURKLZDCOPJ-PKNBQFBNSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- -1 cyanoimino Chemical group 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RFDPHKHXPMDJJD-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one;hydron;chloride Chemical compound Cl.C1CC2C(=O)CN1CC2 RFDPHKHXPMDJJD-UHFFFAOYSA-N 0.000 description 1
- BZLBBZLOMXKMTA-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane;chloride Chemical compound Cl.C1CC2CCN1CC2 BZLBBZLOMXKMTA-UHFFFAOYSA-N 0.000 description 1
- JRKLWGJUSOHFCO-UHFFFAOYSA-N 10,10,10-triphenyldecylphosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(CCCCCCCCC[PH3+])C1=CC=CC=C1 JRKLWGJUSOHFCO-UHFFFAOYSA-N 0.000 description 1
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PPCUNNLZTNMXFO-ACCUITESSA-N Imicyafos Chemical compound CCCSP(=O)(OCC)N1CCN(CC)\C1=N/C#N PPCUNNLZTNMXFO-ACCUITESSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- IUSOXUFUXZORBF-UHFFFAOYSA-N n,n-dioctyloctan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC IUSOXUFUXZORBF-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明方法において使用するアルカリ金属水酸化物、アルカリ土類金属水酸化物又は金属アルコキシドとしては、例えば、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化マグネシウム、水酸化カルシウム、ナトリウムメトキシド、ナトリウムエトキシド、カリウムエトキシド、カリウムt−ブトキシドなどが挙げられるが、望ましくは水酸化ナトリウム、水酸化カリウム、ナトリウムメトキシド、ナトリウムエトキシドやカリウムエトキシド、より望ましくは水酸化ナトリウム、ナトリウムメトキシドである。
次に本発明の実施例を記載する。
99%水酸化ナトリウム10.15g(0.254モル)をトルエン250mlに懸濁させ、2−(シアノイミノ)−1−エチルイミダゾリジン(CEIM)35.58g(0.258モル)を室温で撹拌しながら加えた。加熱還流1.5時間行い、ディンスタークトラップで水4.5mlを留去した。さらに還流しながらトルエン200mlを留去した。その後100mlのトルエンを加え-15℃に冷却した溶液へ、85.1%のO−エチル-S−n−プロピルホスホロクロリドチオアート(OESP)のトルエン溶液59.53g(0.250モル)を30分間で滴下した。滴下後-10℃で約1時間、-10℃〜0℃で1時間撹拌、0℃〜20℃で3時間撹拌して反応させた。反応終了後、反応液を水100mlで洗浄した後、溶媒を留去して油状のO−エチル S−n−プロピル (E)−[2−(シアノイミノ)−3−エチルイミダゾリジン−1−イル]ホスホノチオアート 生成物76.0gを得た(収率99.9%)。この生成物はHPLCによる分析の結果、純度95.0%であった。
28%ナトリウムメトキシドのメタノール溶液48.23g(0.250モル)に2−(シアノイミノ)−1−エチルイミダゾリジン(CEIM)35.58g(0.258モル)を室温で撹拌しながら加えた。その後トルエン80mlを加え、加温してメタノールとトルエンを減圧留去した。さらにトルエン50mlを加えた後、加熱減圧留去してメタノールを完全に除いた。その後150mlのトルエンを加え-15℃に冷却した溶液へ、85.1%のO−エチル-S−n−プロピルホスホロクロリドチオアート(OESP)のトルエン溶液59.53g(0.250モル)を30分間で滴下した。滴下後-10℃で約1時間、-10℃〜0℃で1時間撹拌、0℃〜20℃で3時間撹拌して反応させた。反応終了後、反応液を水70mlで洗浄した後、溶媒を留去して油状のO−エチル S−n−プロピル (E)−[2−(シアノイミノ)−3−エチルイミダゾリジン−1−イル]ホスホノチオアート 生成物75.0gを得た(収率98.6%)。この生成物はHPLCによる分析の結果、純度94.0%であった。
O−エチル-S−n−プロピル(3−エチル−2−シアノイミノ−1−イミダゾリジニル)ホスホノチオレート(化合物番号4)(イミシアホス)の製造
60%水素化ナトリウム0.44g(0.0011モル)及びN,N−ジメチルホルムアミド50mlの混合物に2−(シアノイミノ)−1−エチルイミダゾリジン(CEIM)1.38g(0.0010モル)を徐々に添加した。しばらくしてO−エチル-S−n−プロピルホスホロクロリドチオアート(OESP)の88.2%トルエン溶液2.76g(0.0012モル)を徐々に滴下した。滴下終了後、反応液を氷水へ投入し、クロロホルムで抽出した。クロロホルム層を水洗後、無水硫酸マグネシウムで乾燥し、クロロホルムを減圧留去後、シリカゲルカラムクロマトグラフィー(溶媒=クロロホルム:メタノール=97:3)を用いて精製して油状の表題化合物1.50g(収率49.3%)を得た。
Claims (1)
- 不活性溶媒及び塩基性物質の存在下、2−(シアノイミノ)−1−エチルイミダゾリジンと、O−エチル-S−n−プロピルホスホロクロリドチオアートとを反応させてO−エチル S−n−プロピル (E)−[2−(シアノイミノ)−3−エチルイミダゾリジン−1−イル]ホスホノチオアートを製造する方法において、前記塩基性物質が、水酸化ナトリウム又はナトリウムメトキシドであることを特徴とする方法。
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JP2011156572A JP5818073B2 (ja) | 2011-07-15 | 2011-07-15 | O−エチルS−n−プロピル(E)−[2−(シアノイミノ)−3−エチルイミダゾリジン−1−イル]ホスホノチオアートの製造方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2771882B2 (ja) * | 1990-03-09 | 1998-07-02 | 石原産業株式会社 | S,o―ジアルキル(2―オキソ―3―チアゾリジニル)ホスホノチオレートの製造法 |
JPH0739430B2 (ja) * | 1990-07-06 | 1995-05-01 | アグロカネショウ株式会社 | 有機リン化合物、その製造法および該化合物を含有する殺虫、殺ダニ、殺線虫剤 |
DE4132492A1 (de) * | 1991-09-30 | 1993-04-01 | Bayer Ag | Phosphorylierte diazacycloalkane |
JPH10109994A (ja) * | 1996-10-03 | 1998-04-28 | Sumitomo Chem Co Ltd | アミドチオリン酸エステル誘導体の製造方法 |
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