JPH04139170A - Substituted pyridinesufonylcarbamate-based compound, its production and production of substituted pyridinesulfonamide-based compound - Google Patents
Substituted pyridinesufonylcarbamate-based compound, its production and production of substituted pyridinesulfonamide-based compoundInfo
- Publication number
- JPH04139170A JPH04139170A JP26339290A JP26339290A JPH04139170A JP H04139170 A JPH04139170 A JP H04139170A JP 26339290 A JP26339290 A JP 26339290A JP 26339290 A JP26339290 A JP 26339290A JP H04139170 A JPH04139170 A JP H04139170A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- substituted pyridine
- substituted
- general formula
- production
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical class NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- -1 pyridine sulfonyl carbamate compound Chemical class 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000004009 herbicide Substances 0.000 abstract description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WYFKZPLSYVJLRB-UHFFFAOYSA-N n,n-dimethyl-2-sulfamoylpyridine-3-carboxamide Chemical compound CN(C)C(=O)C1=CC=CN=C1S(N)(=O)=O WYFKZPLSYVJLRB-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、除草剤の有効成分として有用な、後記−数式
（ＩＶ）で表わされる置換ピリジンスルホンアミド系化
合物（以下置換ピリジンスルホンアミド系化合物と略す
）を製造するための中間体として有用な、後記−数式（
Ｉ）で表わされる置換ピリジンスルホニルカーバメート
系化合物及びその製造方法並びに該中間体を用いた前記
置換ピリジンスルホンアミド系化合物の製造方法に関す
る。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a substituted pyridine sulfonamide compound (hereinafter referred to as a substituted pyridine sulfonamide compound) represented by formula (IV) below, which is useful as an active ingredient of a herbicide. (abbreviated as ) is useful as an intermediate for producing the formula (
The present invention relates to a substituted pyridine sulfonyl carbamate compound represented by I), a method for producing the same, and a method for producing the substituted pyridine sulfonamide compound using the intermediate.
（先行技術及び本発明に至った経緯）
前記置換ピリジンスルホニルカーバメート系化合物に近
接した化合物は、特開昭６２−２２３１８０号公報に開
示されている。ここで開示されている化合物は後記−数
式（Ｉ）中、Ｒかフェニル基のもの（Ｒ’及びＲ２はと
もにメチル基である）であるか、このものは、反応条件
次第では反応中に分解したりして、生成取得てきなかっ
たり、また、たとえ生成取得できたとしても室温におけ
る通常の保存状態でさえ分解するというような種々の問
題を有している。(Prior Art and Background of the Present Invention) Compounds close to the above-mentioned substituted pyridine sulfonyl carbamate compounds are disclosed in JP-A-62-223180. The compound disclosed herein is a phenyl group (R' and R2 are both methyl groups) in formula (I), or this compound may be decomposed during the reaction depending on the reaction conditions. They have various problems such as not being able to produce them, or even if they can be produced, they decompose even under normal storage conditions at room temperature.
このようなことから本発明者等は、後記−数式（Ｉ）中
、Ｒかフェニル基以外のものについて種々検討したとこ
ろ、Ｒかアルキル基である置換ピリジンスルホニルカー
バメート系化合物か高収率かつ安定に生成取得でき、さ
らにそれか除草剤の有効成分として有用な置換ピリジン
スルホンアミド系化合物を製造するための中間体として
非常に有用であることを見出し、本発明を完成した。For this reason, the present inventors conducted various studies regarding R in formula (I) below, and found that a substituted pyridine sulfonyl carbamate-based compound in which R is an alkyl group has high yield and stability. The present invention has been completed based on the discovery that it is very useful as an intermediate for producing substituted pyridine sulfonamide compounds useful as active ingredients of herbicides.
（発明の開示）
本発明は、−数式（Ｉ）；
（式中、Ｒ，Ｒ’及びＲ２は各々アルキル基である）で
表わされる置換ピリジンスルホニルカーバメート系化合
物（以下ＡＳＤＭ−Ｃと略す）、−数式（■）：
（式中、Ｒ１及びＲ２は前述の通りである）と、−数式
（Ｉ［）； ＸＣ０ＯＲ・・・（■） （式中、Ｒ
は前述の通りであり、Ｘはハロゲン原子である）で表わ
される化合物とを反応させることを特徴とスル、ＡＳＤ
Ｍ−Ｃ（７）製造方法、及びＡＳＤＭ−Ｃと２−アミノ
−４，６−シメトキシピリミジンとを反応させることを
特徴とする、
一般式（■）；
（式中、Ｒ１及びＲ２は前述の通りである）で表わされ
る、置換ピリジンスルホンアミド系化合物の製造方法に
関する。(Disclosure of the Invention) The present invention provides a substituted pyridine sulfonyl carbamate compound (hereinafter abbreviated as ASDM-C) represented by formula (I); (wherein R, R' and R2 are each an alkyl group); - Formula (■): (In the formula, R1 and R2 are as described above) and - Formula (I[); XC0OR... (■) (In the formula, R
is as described above, and X is a halogen atom).
M-C (7) production method, characterized by reacting ASDM-C and 2-amino-4,6-simethoxypyrimidine, general formula (■); The present invention relates to a method for producing a substituted pyridine sulfonamide compound represented by:
前記−数式（Ｉ）〜（ＩＶ）中Ｒ，Ｒ’及びＲ２て表わ
されるアルキル基としては、炭素数１〜６を有するもの
、例えばメチル基、エチル基、プロピル基、ブチル基な
どが挙げられ、それらは直鎖又は枝分れ脂肪鎖の幾何異
性のものを含み、なかでもＲとしてはエチル基か望まし
い。The alkyl groups represented by R, R' and R2 in the formulas (I) to (IV) include those having 1 to 6 carbon atoms, such as methyl group, ethyl group, propyl group, butyl group, etc. , they include linear or branched aliphatic chain geometric isomers, and among them R is preferably an ethyl group.
前記一般式（Ｉ［）中Ｘて表わされるハロゲン原子とし
ては、塩素原子、臭素原子、沃素原子か挙げられ、なか
でも塩素原子が望ましい。The halogen atom represented by X in the general formula (I[) includes a chlorine atom, a bromine atom, and an iodine atom, of which a chlorine atom is preferred.
本発明に係るＡＳＤＭ−Ｃの製造方法を以下に詳述する
。The method for manufacturing ASDM-C according to the present invention will be described in detail below.
（ｎ） （Ｉ） （Ｉ）（
式中、Ｒ，Ｒ’ 、Ｒ’及びＸは前述の通りである）。(n) (I) (I)(
(wherein R, R', R' and X are as defined above).
一般式（ＩＩＩ）で表わされる化合物の使用量は一概に
規定てきないか、一般式（Ｉｔ）で表わされる化合物に
対して通常１〜２倍モル、望ましくは１．２〜１．５倍
モルである。The amount of the compound represented by the general formula (III) to be used cannot be absolutely defined, or is usually 1 to 2 times the amount of the compound represented by the general formula (It), preferably 1.2 to 1.5 times the amount of the compound represented by the general formula (It). It is.
上記反応で使用される塩基としては例えば、無水炭酸カ
リウム、水酸化ナトリウム、水酸化カリウムなどが挙げ
られ、その使用量は一概に規定てきないか、一般式（Ｉ
Ｉ）で表わされる化合物に対して通常２〜４倍当量、望
ましくは２．４〜３．０倍当量である。Examples of the base used in the above reaction include anhydrous potassium carbonate, sodium hydroxide, potassium hydroxide, etc., and the amount used cannot be unconditionally specified, or the general formula (I
The amount is usually 2 to 4 times equivalent, preferably 2.4 to 3.0 times equivalent, relative to the compound represented by I).
また、上記反応で使用される溶媒としては例えば、アセ
トンなとのケトン類、アセトニトリルなどのニトリル類
、前記溶媒と水との混合物などが挙げられ、その使用量
は一概に規定てきないか、一般式（Ｉ［）で表わされる
化合物１ｇに対して通常３〜２０ｍ１、望ましくは５〜
１０ｍ１である。Examples of solvents used in the above reaction include ketones such as acetone, nitriles such as acetonitrile, and mixtures of the above solvents and water. Usually 3 to 20 ml, preferably 5 to 20 ml per 1 g of the compound represented by formula (I[)
It is 10m1.
上記反応の反応条件は一概（こ規定てきないか、反応温
度は通常ｌＯ〜１００°Ｃ１反応時間は通常０．５〜１
０時間である。The reaction conditions for the above reaction are general (reaction temperature is usually 10 to 100°C, reaction time is usually 0.5 to 1
It is 0 hours.
上記製造方法で得られるＡＳＤＭ−Ｃを原料として使用
して、下記製造方法により、一般式（ＩＶ）て表わされ
る置換ピリジンスルホンアミド系化合物を製造すること
かできる。A substituted pyridine sulfonamide compound represented by general formula (IV) can be produced by the following production method using ASDM-C obtained by the above production method as a raw material.
前記２−アミノ−４，６−ジメトキシピリミジンの使用
量は一概に規定できないか、ＡＳＤＭ−Ｃに対して通常
１〜２モルである。The amount of the 2-amino-4,6-dimethoxypyrimidine to be used cannot be unconditionally defined, or is usually 1 to 2 moles relative to ASDM-C.
上記反応で使用される溶媒としては例えば、ベンゼン、
トルエンなどの芳香族炭化水素類か挙げられ、その使用
量は一概に規定できないか、ＡＳＤＭ−Ｃ１ｇに対して
通常３〜３０７ｎ１１望ましくは５〜１５ｒｎｌである
。Examples of the solvent used in the above reaction include benzene,
Examples include aromatic hydrocarbons such as toluene, and the amount to be used cannot be absolutely specified, but is usually 3 to 307 n1, preferably 5 to 15 rnl, per gram of ASDM-C.
上記反応の反応条件は一概に規定できないが、反応温度
は通常、使用する溶媒の還流温度であり、反応時間は通
常１〜１５時間である。Although the reaction conditions for the above reaction cannot be absolutely defined, the reaction temperature is usually the reflux temperature of the solvent used, and the reaction time is usually 1 to 15 hours.
（実施例）
本発明をより詳しく述べるため、以下に実施例を記載す
るか、これらは本発明を限定するものではない。(Examples) In order to describe the present invention in more detail, examples are described below, but these examples are not intended to limit the present invention.
実施例１． エチル＜３−（（Ｎ、Ｎ−ジメチルアミノ
カルボニル）−２−ピリジニル〕ス
ルホニル）カーバメートの合成
３１四つロフラスコに、２−アミノスルホニル−Ｎ、Ｎ
−ジメチルニコチンアミド ２０６．１ ｇ（０，９ｍ
ｏｌ）、無水炭酸カリウム１６１．５ ｇ （１，１７
ｍｏｌ）及びアセトニトリル２１を仕込み、室温でクロ
ル炭酸エチルエステル１２２．１ ｇ （１，１３ｍｏ
ｌ）を２０分間を要して攪拌下に滴下した。Example 1. Synthesis of ethyl<3-((N,N-dimethylaminocarbonyl)-2-pyridinyl]sulfonyl)carbamate 31 In a four-loaf flask, 2-aminosulfonyl-N,N
-dimethylnicotinamide 206.1 g (0.9 m
ol), anhydrous potassium carbonate 161.5 g (1,17
mol) and acetonitrile, and at room temperature 122.1 g (1,13 mo
1) was added dropwise over a period of 20 minutes while stirring.
その後、還流温度で１時間反応させ、次いてアセトニト
リルを留去した。四つロフラスコに水５００ｍ１を加え
反応物を溶解させ、濃塩酸てｐＨ２以下に調整して結晶
を析出させた。Thereafter, the reaction was carried out at reflux temperature for 1 hour, and then acetonitrile was distilled off. 500 ml of water was added to a four-bottle flask to dissolve the reactant, and the pH was adjusted to below 2 with concentrated hydrochloric acid to precipitate crystals.
得られた結晶を濾過、水洗後乾燥し、融点１６０〜１６
４°Ｃの目的物２４６ｇを得た（収率９０．８％）。The obtained crystals were filtered, washed with water and dried, and the melting point was 160-16.
246 g of the target product was obtained at 4°C (yield: 90.8%).
実施例２． Ｎ−Ｃ（４，６−シメトキシビリミジン
ー２−イル）アミノカルボニルシー
３−ジメチルアミノカルボニル−２＝
ピリジンスルホンアミドの合成
２００イ四つロフラスコに前記実施例１で得た目的物５
．１ ｇ （０，０１７ｍｏｌ）、２−アミノ−４，６
−シメトキシピリミジン２．６ ｇ （０，０１７ｍｏ
ｌ）及びトルエン５０ｍ１を仕込み、還流下、留出物を
２０ｍ１／時間の割合で留去し、同時に同じ割合でトル
エンを投入しながら５時間反応させた。Example 2. Synthesis of N-C(4,6-cymethoxypyrimidin-2-yl)aminocarbonyl-3-dimethylaminocarbonyl-2=pyridine sulfonamide 200 Into a four-necked flask, put the target product 5 obtained in Example 1 above.
．． 1 g (0,017 mol), 2-amino-4,6
-cymethoxypyrimidine 2.6 g (0,017 mo
1) and 50 ml of toluene were charged, and the distillate was distilled off at a rate of 20 ml/hour under reflux, and the reaction was allowed to proceed for 5 hours while simultaneously adding toluene at the same rate.
反応終了後、２０°Ｃまて冷却して１．５％水酸化ナト
リウム水溶液を投入し、１５分間攪拌した。After the reaction was completed, the mixture was cooled to 20°C, a 1.5% aqueous sodium hydroxide solution was added, and the mixture was stirred for 15 minutes.
その後、水層をトルエン層と分液し、５０％硫酸でｐＨ
２に調整して結晶を析出させた。After that, the aqueous layer was separated from the toluene layer, and the pH was adjusted with 50% sulfuric acid.
2 to precipitate crystals.
得られた結晶を濾取した後、乾燥し目的物６．６２ｇを
得た（収率９４．９％）。The obtained crystals were collected by filtration and dried to obtain 6.62 g of the target product (yield: 94.9%).
Claims (1)
）で表わされる、置換ピリジンスルホニルカーバメート
系化合物。 ２、Ｒがエチル基であり、Ｒ＾１及びＲ＾２がともにメ
チル基である、請求項１に記載の置換ピリジンスルホニ
ルカーバメート系化合物。 ３、一般式（II）； ▲数式、化学式、表等があります▼・・・（II） （式中、Ｒ＾１及びＲ＾２は各々アルキル基である）て
表わされる化合物と、一般式（III）； ＸＣＯＯＲ・・・（III） （式中、Ｒはアルキル基であり、Ｘはハロゲン原子であ
る）で表わされる化合物とを反応させることを特徴とす
る、一般式（ I ）； ▲数式、化学式、表等があります▼・・・（ I ） （式中、Ｒ、Ｒ＾１及びＲ＾２は前述の通りである）で
表わされる、置換ピリジンスルホニルカーバメート系化
合物の製造方法。 ４、Ｒがエチル基であり、Ｒ＾１及びＲ＾２がともにメ
チル基である、請求項３に記載の置換ピリジンスルホニ
ルカーバメート系化合物の製造方法。 ５、一般式（ I ）； ▲数式、化学式、表等があります▼・・・（ I ） （式中、Ｒ、Ｒ＾１及びＲ＾２は各々アルキル基である
）で表わされる置換ピリジンスルホニルカーバメート系
化合物と、２−アミノ−４，６−ジメトキシピリミジン
とを反応させることを特徴とする、 一般式（IV）； ▲数式、化学式、表等があります▼・・・（IV） （式中、Ｒ＾１及びＲ＾２は前述の通りである）で表わ
される、置換ピリジンスルホンアミド系化合物の製造方
法。 ６、Ｒがエチル基であり、Ｒ＾１及びＲ＾２がともにメ
チル基である、請求項５に記載の置換ピリジンスルホン
アミド系化合物の製造方法。[Claims] 1. General formula (I); ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R, R^1 and R^2 are each an alkyl group) A substituted pyridine sulfonyl carbamate compound represented by: 2. The substituted pyridine sulfonyl carbamate compound according to claim 1, wherein R is an ethyl group, and R^1 and R^2 are both methyl groups. 3. General formula (II); ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R^1 and R^2 are each an alkyl group) A compound represented by the following and the general formula (III); General formula (I) characterized by reacting with a compound represented by XCOOR...(III) (wherein R is an alkyl group and X is a halogen atom); ▲ There are mathematical formulas, chemical formulas, tables, etc.▼...(I) A method for producing a substituted pyridine sulfonyl carbamate compound represented by (in the formula, R, R^1 and R^2 are as described above). 4. The method for producing a substituted pyridine sulfonyl carbamate compound according to claim 3, wherein R is an ethyl group, and R^1 and R^2 are both methyl groups. 5. General formula (I); ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) Substituted pyridine sulfonyl represented by (in the formula, R, R^1 and R^2 are each an alkyl group) General formula (IV) characterized by reacting a carbamate compound and 2-amino-4,6-dimethoxypyrimidine; ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(IV) (In the formula , R^1 and R^2 are as described above), a method for producing a substituted pyridine sulfonamide compound. 6. The method for producing a substituted pyridine sulfonamide compound according to claim 5, wherein R is an ethyl group, and R^1 and R^2 are both methyl groups.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26339290A JP2931064B2 (en) | 1990-10-01 | 1990-10-01 | Substituted pyridinesulfonyl carbamate compound, method for producing the same, and method for producing substituted pyridinesulfonamide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26339290A JP2931064B2 (en) | 1990-10-01 | 1990-10-01 | Substituted pyridinesulfonyl carbamate compound, method for producing the same, and method for producing substituted pyridinesulfonamide compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04139170A true JPH04139170A (en) | 1992-05-13 |
| JP2931064B2 JP2931064B2 (en) | 1999-08-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26339290A Expired - Lifetime JP2931064B2 (en) | 1990-10-01 | 1990-10-01 | Substituted pyridinesulfonyl carbamate compound, method for producing the same, and method for producing substituted pyridinesulfonamide compound |
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| Country | Link |
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| JP (1) | JP2931064B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011039276A1 (en) | 2009-10-01 | 2011-04-07 | Bayer Cropscience Ag | Oxathiazinyl(het)arylsulfonylureas, processes and intermediates for preparation thereof and use thereof as crop protection agents and crop growth regulators |
| CN103073488A (en) * | 2012-12-28 | 2013-05-01 | 合肥久易农业开发有限公司 | Synthesis method of sulfonamide formate |
| CN112645930A (en) * | 2020-12-30 | 2021-04-13 | 邯郸市瑞田农药有限公司 | Nicosulfuron water-phase method synthesis process |
-
1990
- 1990-10-01 JP JP26339290A patent/JP2931064B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011039276A1 (en) | 2009-10-01 | 2011-04-07 | Bayer Cropscience Ag | Oxathiazinyl(het)arylsulfonylureas, processes and intermediates for preparation thereof and use thereof as crop protection agents and crop growth regulators |
| CN103073488A (en) * | 2012-12-28 | 2013-05-01 | 合肥久易农业开发有限公司 | Synthesis method of sulfonamide formate |
| CN112645930A (en) * | 2020-12-30 | 2021-04-13 | 邯郸市瑞田农药有限公司 | Nicosulfuron water-phase method synthesis process |
| CN112645930B (en) * | 2020-12-30 | 2022-08-09 | 邯郸市瑞田农药有限公司 | Nicosulfuron water-phase method synthesis process |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2931064B2 (en) | 1999-08-09 |
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