JPH02207083A - Production of 2-nitroiminoimidazolidines - Google Patents
Production of 2-nitroiminoimidazolidinesInfo
- Publication number
- JPH02207083A JPH02207083A JP1024782A JP2478289A JPH02207083A JP H02207083 A JPH02207083 A JP H02207083A JP 1024782 A JP1024782 A JP 1024782A JP 2478289 A JP2478289 A JP 2478289A JP H02207083 A JPH02207083 A JP H02207083A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- methyl
- nitroiminoimidazolidines
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- DJZWNSRUEJSEEB-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)nitramide Chemical class [O-][N+](=O)NC1=NCCN1 DJZWNSRUEJSEEB-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 239000012442 inert solvent Substances 0.000 claims abstract description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- -1 methoxy, phenyl Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 229940100198 alkylating agent Drugs 0.000 claims abstract 3
- 239000002168 alkylating agent Substances 0.000 claims abstract 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 2
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- QDUFZQAVFCKSPU-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-3-methylimidazolidin-2-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(C)CCN1CC1=CC=C(Cl)N=C1 QDUFZQAVFCKSPU-UHFFFAOYSA-N 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
【発明の詳細な説明】
本発明は２−ニトロイミノイミダゾリジン類の製法に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2-nitroiminoimidazolidines.
式：
〔式中、Ｘはハロゲン原子又はアルキル基を示し、そし
て
Ｒはアルキル基、アルケニル基、アルキニル基、ハロア
ルキル基、ハロアルケニル基、アルコキシアルキル基、
アルキルチオアルキル基、アラルキル基又は芳香族へテ
ロ環式基と結合したメチル基を示す、〕
で表わされる２−ニトロイミノイミダゾリジン類は、特
開昭６２−８１３８２号に記載される殺虫活性を有する
化合物である。Formula: [wherein, X represents a halogen atom or an alkyl group, and R represents an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, an alkoxyalkyl group,
2-Nitroiminoimidazolidines represented by ], which represents a methyl group bonded to an alkylthioalkyl group, an aralkyl group, or an aromatic heterocyclic group, have insecticidal activity as described in JP-A-62-81382. It is a compound.
特開昭６２−８１３８２号によれば、式（１）の化合物
は、エチレンジアミン類とニトログアニジンとを反応さ
せるか、又は、相当する２−ニトロイミノイミダゾリジ
ン類と、３−ピリジルメチルノ１ライド類とを反応させ
ることにより、得られる。According to JP-A No. 62-81382, the compound of formula (1) can be prepared by reacting ethylenediamines with nitroguanidine, or by reacting the corresponding 2-nitroiminoimidazolidine with 3-pyridylmethylno1lide. It can be obtained by reacting with
本発明者等は、前記式（１）の２−ニトロイミノイミダ
プリジン類をより簡便且つ効率的に得る方法を検討した
結果、この度、下記で示される方法を見出した。即ち、
前記式（１）の２−ニトロイミノイミダゾリジン類を製
造するに、式：
〔式中、Ｘは前記と同じ、〕
で表わされる化合物と、
式：
％式％（［）
（式中、Ｒは前記と同じ、そして
Ｍはハロゲン原子又は−０ＳＯ＊Ｔ を示し、ここで
Ｔはメチル、メトキシ、フェニル又はＰ−）リルを示す
、］
で表わされるアルキル化剤とを、塩基及び相聞移動触媒
の存在下、不活性溶媒中で反応させることを特徴とする
、前記式（１）の２−ニトロイミノイミダゾリジン類の
製造方法。The present inventors investigated a method for obtaining the 2-nitroiminoimidapridine of the formula (1) more easily and efficiently, and as a result, they discovered the method shown below. That is,
To produce the 2-nitroiminoimidazolidine of the formula (1), a compound represented by the formula: [wherein X is the same as above] and the formula: %formula%([) (wherein, R is the same as above, and M represents a halogen atom or -0SO*T, where T represents methyl, methoxy, phenyl or P-)lyl, and a base and a phase transfer catalyst. A method for producing 2-nitroiminoimidazolidines of the formula (1), characterized by carrying out the reaction in the presence of an inert solvent.
本発明の方法は、文献未記載の新規方法であり、目的の
式（１）の化合物を、高収率、高純度で得ることを可能
にすると共に、操作上も簡便である。The method of the present invention is a novel method that has not been described in any literature, and allows the target compound of formula (1) to be obtained in high yield and purity, and is also operationally simple.
本発明の方法に於ける式（Ｉ［）の化合物は、特開昭６
１−２６７５７５号に記載される公知のものであり、そ
の具体例としては、
１−（２−クロロ−５−ピリジルメチル）−２ニトロイ
ミノイミダゾリジン、
１−（２−メチル−５−ピリジルメチル）−２＝ニトロ
イミノイミダゾリジン、
を例示できる。The compound of formula (I[) in the method of the present invention is
1-267575, and specific examples thereof include 1-(2-chloro-5-pyridylmethyl)-2nitroiminoimidazolidine, 1-(2-methyl-5-pyridylmethyl )-2=nitroiminoimidazolidine, can be exemplified.
同様に式（ｌ［［）の化合物は、有機化学の分野でよく
知られたものである。Similarly, compounds of formula (l[[) are well known in the field of organic chemistry.
本発明の方法を実施するに際して、用いられる塩基とし
ては、水酸化ナトリウム、水酸化カリウム等のアルカリ
金属水酸化物、ナトリウムメトキシド、ナトリウムエト
キシド又はボタシウムーｔｅｒ ｔ−ブトキシド等のア
ルカリ金属のアルコキシド類を挙げることができる。In carrying out the method of the present invention, the bases used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and bota-tert-butoxide. can be mentioned.
同様に相間移動触媒としては、トリエチルベンジルアン
モニウムクロライド、テトラブチルアンモニウムブロマ
イド等の４級アンモニウム塩又は１８−クラウン−６等
を挙げることができる。Similarly, examples of the phase transfer catalyst include quaternary ammonium salts such as triethylbenzylammonium chloride and tetrabutylammonium bromide, or 18-crown-6.
同様に不活性溶媒としては、塩化メチレン、ベンゼン、
トルエン、ヘキサン等を挙げることができる。Similarly, inert solvents include methylene chloride, benzene,
Examples include toluene and hexane.
本発明の方法は、反応温度として、約−１Ｏ°Ｃ〜約６
０℃、好ましくは約０°Ｃ〜約３０℃の間で行うことが
できる。In the method of the present invention, the reaction temperature ranges from about -10°C to about 6°C.
It can be carried out at 0°C, preferably between about 0°C and about 30°C.
また反応は、常圧の下で行うことが好ましいが、加圧ま
たは減圧下で操作することもできる。Although the reaction is preferably carried out under normal pressure, it can also be carried out under increased pressure or reduced pressure.
次に本発明の方法を、下記の実施例により具体的に示す
が、本発明はこれのみに限定されるべきものではない。Next, the method of the present invention will be specifically illustrated by the following examples, but the present invention should not be limited thereto.
実施例１
実施例２
ｌ−（２−クロロ−５−ピリジルメチル〕−２−ニトロ
イミノイミダゾリジン（２５５，５ｇ）を、塩化メチレ
ン（１，５ｊりに加える。この溶液にトリエチルベンジ
ルアンモニウムクロライド（１１，４ｇ）と水酸化カリ
ウム（８５，６ｇ）を加え、室温で３０分撹拌すると、
均一な溶液となる０反応フラスコを水浴中で冷却しなが
ら、６〜１３℃でジメチル硫ＩＩ！ １５０ ｇを１時
間にわたって滴下する。Example 1 Example 2 l-(2-chloro-5-pyridylmethyl)-2-nitroiminoimidazolidine (255.5 g) is added to methylene chloride (1.5 g). To this solution is added triethylbenzylammonium chloride ( 11.4 g) and potassium hydroxide (85.6 g) and stirred at room temperature for 30 minutes.
Dimethyl sulfur II! at 6-13° C. while cooling the reaction flask in a water bath to form a homogeneous solution! 150 g are added dropwise over the course of 1 hour.
その後、６〜１３℃で３時間撹拌する。塩化メチレン層
を分液後、１％塩酸水溶液、水で洗い無水硫酸ナトリウ
ムで乾燥する。減圧下に塩化メチレンを留去し、残渣を
エタノールより再結晶すると、目的の−ｐ、１０７．５
〜１０８．５°Ｃの１−（２−クロロ−５−ピリジルメ
チル）−３−メチル−２−ニトロイミノイミダゾリジン
（２２２ｇ）が得られる。Then, stir at 6-13°C for 3 hours. After separating the methylene chloride layer, it is washed with a 1% aqueous hydrochloric acid solution and water, and dried over anhydrous sodium sulfate. Methylene chloride was distilled off under reduced pressure, and the residue was recrystallized from ethanol to obtain the desired -p, 107.5
1-(2-chloro-5-pyridylmethyl)-3-methyl-2-nitroiminoimidazolidine (222 g) at ~108.5°C is obtained.
収率８２％。Yield 82%.
１−（２−クロロ−５−ピリジルメチル）−２ニトロイ
ミノイミダゾリジン（２５５，５ｇ）を、塩化メチレン
（１，！Ｍりに加える。この溶液にトリエチルベンジル
アンモニウムクロライド（１１，４ｇ）と水酸化カリウ
ム（８５，６ｇ）を加え、室温で３０分攪拌すると、均
一な溶液となる０反応フラスコを水浴中で８〜１５°Ｃ
に冷却しながら、アリルブロマイド（１４０ｇ）を２時
間にわたって滴下する。その後１５°Ｃで８時間攪拌す
る。内容物を氷に注ぎ、塩化メチレン層を分液後、１％
塩酸水溶液、水で洗い、無水硫酸ナトリウムで乾燥する
。減圧下に塩化メチレンを留去し、残渣をエタノールよ
り再結晶すると、目的の諷ｐ、 １０３〜１０５℃の１
−アリル−３−（２−クロロ−５ピリジルメチル）−２
−ニトロイミノイミダゾリジン（２０１ｇ）が得られる
。収率６８％。1-(2-chloro-5-pyridylmethyl)-2nitroiminoimidazolidine (255.5 g) is added to methylene chloride (1,!M). To this solution is added triethylbenzylammonium chloride (11.4 g) and water. Add potassium oxide (85,6 g) and stir for 30 minutes at room temperature, resulting in a homogeneous solution.The reaction flask was heated in a water bath at 8-15 °C.
Allyl bromide (140 g) is added dropwise over 2 hours while cooling to . Then stir at 15°C for 8 hours. Pour the contents onto ice, separate the methylene chloride layer, and add 1%
Wash with aqueous hydrochloric acid and water, and dry with anhydrous sodium sulfate. Methylene chloride was distilled off under reduced pressure, and the residue was recrystallized from ethanol to obtain the desired solution, 1 at 103-105°C.
-Allyl-3-(2-chloro-5pyridylmethyl)-2
- Nitroiminoimidazolidine (201 g) is obtained. Yield 68%.
上記実施例１及び２と同様の方法に従って得られる式（
１）の化合物を下記表に示す。The formula (
The compounds of 1) are shown in the table below.
（以下余白） 第 １ 表(Margin below) Table 1
Claims (1)
て Ｒはアルキル基、アルケニル基、アルキニル基、ハロア
ルキル基、ハロアルケニル基、アルコキシアルキル基、
アルキルチオアルキル基、アラルキル基又は芳香族ヘテ
ロ環式基と結合したメチル基を示す。〕 で表わされる２−ニトロイミノイミダゾリジン類を製造
するに、 ▲数式、化学式、表等があります▼（II） 〔式中、Ｘは前記と同じ。〕 で表わされる化合物と、 式： Ｒ−Ｍ（III） 〔式中、Ｒは前記と同じ、そして Ｍはハロゲン原子又は−ＯＳＯ＿２Ｔを示し、ここで Ｔはメチル、メトキシ、フェニル又はｐ−トリルを示す
。〕 で表わされるアルキ化剤とを、塩基及び相間移動触媒の
存在下、不活性溶媒中で反応させることを特徴とする、
上記式（ I ）の２−ニトロイミノイミダゾリジン類の
製造方法。[Claims] Formulas: ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X represents a halogen atom or an alkyl group, and R represents an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, haloalkenyl group, alkoxyalkyl group,
Indicates a methyl group bonded to an alkylthioalkyl group, an aralkyl group, or an aromatic heterocyclic group. ] To produce 2-nitroiminoimidazolidines represented by ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼ (II) [In the formula, X is the same as above. ] A compound represented by the formula: RM(III) [wherein R is the same as above, and M represents a halogen atom or -OSO_2T, where T represents methyl, methoxy, phenyl or p-tolyl. show. ] is characterized by reacting it with an alkylating agent represented by in an inert solvent in the presence of a base and a phase transfer catalyst,
A method for producing 2-nitroiminoimidazolidines of the above formula (I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1024782A JP2822050B2 (en) | 1989-02-04 | 1989-02-04 | Method for producing 2-nitroimino imidazolidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1024782A JP2822050B2 (en) | 1989-02-04 | 1989-02-04 | Method for producing 2-nitroimino imidazolidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02207083A true JPH02207083A (en) | 1990-08-16 |
| JP2822050B2 JP2822050B2 (en) | 1998-11-05 |
Family
ID=12147755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1024782A Expired - Lifetime JP2822050B2 (en) | 1989-02-04 | 1989-02-04 | Method for producing 2-nitroimino imidazolidines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2822050B2 (en) |
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| WO2002043494A2 (en) | 2000-11-30 | 2002-06-06 | Bayer Healthcare Llc | Compositions for enhanced acaricidal activity |
| US6528079B2 (en) | 1996-06-04 | 2003-03-04 | Bayer Aktiengesellschaft | Shaped bodies which release agrochemical active substances |
| US6534529B2 (en) | 1995-12-27 | 2003-03-18 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
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| CZ300093B6 (en) * | 1999-06-23 | 2009-01-28 | Syngenta Participations Ag | Process for preparing thiamethoxam |
| US7728011B2 (en) | 2001-04-09 | 2010-06-01 | Bayer Animal Health Gmbh | Dermally applicable liquid formulations for controlling parasitic insects on animals |
| US8232261B2 (en) | 2003-07-18 | 2012-07-31 | Bayer Cropscience Lp | Method of minimizing herbicidal injury |
| US8268750B2 (en) | 2003-11-14 | 2012-09-18 | Bayer Cropscience Ag | Combination of active substances with insecticidal properties |
| US9919979B2 (en) | 2005-01-21 | 2018-03-20 | Bayer Cropscience Lp | Fertilizer-compatible composition |
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-
1989
- 1989-02-04 JP JP1024782A patent/JP2822050B2/en not_active Expired - Lifetime
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|---|---|---|---|---|
| US6534529B2 (en) | 1995-12-27 | 2003-03-18 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
| US7659228B2 (en) | 1995-12-27 | 2010-02-09 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
| US6680065B2 (en) | 1996-06-04 | 2004-01-20 | Bayer Aktiengesellschaft | Shaped bodies which release agrochemical active substances |
| US6528079B2 (en) | 1996-06-04 | 2003-03-04 | Bayer Aktiengesellschaft | Shaped bodies which release agrochemical active substances |
| US7001903B2 (en) | 1998-05-26 | 2006-02-21 | Bayer Aktiengesellschaft | Synergistic insecticidal mixtures |
| US6828275B2 (en) | 1998-06-23 | 2004-12-07 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
| US6149913A (en) * | 1998-11-16 | 2000-11-21 | Rhone-Poulenc Ag Company, Inc. | Compositions and methods for controlling insects |
| US6716874B1 (en) | 1999-03-24 | 2004-04-06 | Bayer Aktiengesellschaft | Synergistic insecticide mixtures |
| US6894074B2 (en) | 1999-03-24 | 2005-05-17 | Bayer Aktiengesellschaft | Synergistic insecticidal mixtures |
| US6156703A (en) * | 1999-05-21 | 2000-12-05 | Ijo Products, Llc | Method of inhibiting fruit set on fruit producing plants using an aqueous emulsion of eicosenyl eicosenoate and docosenyl eicosenoate |
| CZ300093B6 (en) * | 1999-06-23 | 2009-01-28 | Syngenta Participations Ag | Process for preparing thiamethoxam |
| US8841294B2 (en) | 1999-10-07 | 2014-09-23 | Bayer Cropscience Ag | Active ingredient combinations having insecticidal and acaricidal properties |
| US6893651B1 (en) | 1999-10-07 | 2005-05-17 | Bayer Aktiengesellschaft | Active ingredient combinations having insecticidal and acaricidal properties |
| WO2002043494A2 (en) | 2000-11-30 | 2002-06-06 | Bayer Healthcare Llc | Compositions for enhanced acaricidal activity |
| US7728011B2 (en) | 2001-04-09 | 2010-06-01 | Bayer Animal Health Gmbh | Dermally applicable liquid formulations for controlling parasitic insects on animals |
| US8232261B2 (en) | 2003-07-18 | 2012-07-31 | Bayer Cropscience Lp | Method of minimizing herbicidal injury |
| US8426339B2 (en) | 2003-07-18 | 2013-04-23 | Bayer Cropscience Lp | Method of minimizing herbicidal injury |
| US8268750B2 (en) | 2003-11-14 | 2012-09-18 | Bayer Cropscience Ag | Combination of active substances with insecticidal properties |
| US8993483B2 (en) | 2003-11-14 | 2015-03-31 | Bayer Intellectual Property Gmbh | Combination of active substances with insecticidal properties |
| US9919979B2 (en) | 2005-01-21 | 2018-03-20 | Bayer Cropscience Lp | Fertilizer-compatible composition |
| CN110922390A (en) * | 2019-12-31 | 2020-03-27 | 上海汉维生物医药科技有限公司 | Preparation method of imidacloprid impurity |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2822050B2 (en) | 1998-11-05 |
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