CN100424074C - 具有除草活性的n-异吲哚二酮取代苯基脲类化合物 - Google Patents
具有除草活性的n-异吲哚二酮取代苯基脲类化合物 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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Abstract
本发明公开了通式(I)所示的具有除草活性的N-异吲哚二酮取代苯基脲类化合物。其中X为氢，卤素，氰基，甲基，卤素指氟和氯；Y为氢，卤素，卤素指氟和氯；R1为(C1-C6)直链或支链烷基，(C1-C6)卤代烷基，单取代或多取代苯基，单取代或多取代苯甲酰基；R2为氢，(C1-C4)直链或支链烷基。本发明化合物在75g ai/ha的剂量下苗前土壤处理或苗后茎叶处理时，对苘麻、藜、凹头苋等双子叶杂草表现出较好的除草活性，防效≥80%，对马唐、稗草和狗尾草等部分单子叶杂草也有一定的防效。
Description
技术领域：
本发明涉及具有除草活性的N-异吲哚二酮取代苯基脲类化合物及其制备方法。
背景技术：
到目前为止，有关原卟啉原氧化酶抑制剂除草剂和脲类除草剂多有报导，如：吲哚酮草酯、丙炔氟草胺、唑啶草酮、杀草隆、伏草隆，但末见有N-异吲哚二酮取代苯基脲类结构化合物的报道。而且由于除草剂存在杀草谱单一或使用一段时间后，杂草产生抗性等缺点，因此，需要发明新型和改进的除草化合物及组合物。
发明内容：
本发明的目的在于提供一种具有除草活性的N-异吲哚二酮取代苯基脲类化合物及其制备方法。
本发明用结构通式(I)表示：
其中
X为氢，卤素，氰基，甲基，卤素指氟和氯；
Y为氢，卤素，卤素指氟和氯；
R1为(C1-C6)直链或支链烷基，(C1-C6)卤代烷基，单取代或多取代苯基，单取代或多取代苯甲酰基；
R2为氢，(C1-C4)直链或支链烷基。
本发明中通式(I)化合物可采用中间体2-(5-氨基-2，4-二取代苯基)-4，5，6，7-四氢-2H-异吲哚-1，3-二酮A为起始原料通过两种不同路线分别合成不同取代基的脲类化合物：
(1)当R2为氢原子时，通式(I)的制备方法是：采用异氰酸酯法合成双取代脲，即在溶剂中加入一定量的烷基异氰酸酯、取代苯基异氰酸酯或取代苯甲酰基异氰酸酯B，氮气保护下滴加相应量的中间体2-(5-氨基-2，4-二取代苯基)-4，5，6，7-四氢-2H-异吲哚-1，3-二酮A，滴加完毕，在一定的温度下反应1-12小时得到目标化合物(I)。上述反应中较好的溶剂是二氯乙烷；较好的摩尔比为A∶B＝1∶1.3；较佳的反应温度是所选溶剂回流温度；较优的反应时间为5小时。具体合成路线用方程式(1)表示。
(2)当R2不为氢原子时，通式(I)的制备方法是：采用一锅法合成三取代脲，即在溶剂中加入一定量的固体光气，然后在氮气保护下滴加相应量的中间体2-(5-氨基-2，4-二卤代苯基)-4，5，6，7-四氢-2H-异吲哚-1，3-二酮A和三乙胺，室温下反应半小时，再次滴加相应量的二取代胺C和三乙胺，滴加完毕在一定的温度下反应1-12小时得到目标化合物(I)。上述反应中较好的溶剂是二氯乙烷；较好的摩尔比为A∶C(R1R2NH)∶固体光气∶三乙胺＝1∶1∶0.35∶4；较佳的反应温度为25℃左右；较优的反应时间为半小时。具体合成路线用方程式(2)表示。
中间体(A)采用参考文献EP0786453描述的方法合成。
根据本发明活性化合物的制备和应用通过下述实施例例示，但这些实施例的技术内容不限制本发明的范围。
合成的部分本发明通式(I)所示的化合物见表1。
表1：部分本发明通式(I)所示的化合物的化学结构与熔点
本发明通式(I)化合物具有高效、安全除草效果，在苗前苗后使用能有效控制双子叶杂草。
具体实施方式：
实施例1：1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-3-(3-三氟甲基苯基)脲(表1中化合物01)的制备。
向装有干燥管和回流冷凝管的100mL三口烧瓶中加入30mL二氯乙烷和0.97g(5.2mmol)间三氟甲基苯基异氰酸酯，磁力搅拌，氮气保护下滴加1.17g(4mmol)2-(5-氨基-4-氯-2-氟苯基)异吲哚-1，3-二酮，滴毕室温反应0.5h，加热至回流反应5h。脱溶得浅黄色固体，经柱层析得到目标产物1.44g，即1-[2-氯-5-(1，3-二样-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-3-(3-三氟甲基苯基)脲，含量95％，m.p.215.3～217.1℃，收率85％。
1H NMR(CDCl3，ppm)δ：1.88(s，4H，cyclohexene)，2.48(s，4H，cyclohexene)，7.11(s，1H，m-F3C-Ph-N-H)，7.32～8.25(m，6H，Ar-H)，7.68(s，1H，NH)。
实施例2：1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-3-(2，6-二氟-苯甲酰基)脲(表1中化合物07)的制备。
向装有干燥管和回流冷凝管的100mL三口烧瓶中加入30mL二氯乙烷和0.42g(2.3mmol)间三氟甲基苯甲酰基异氰酸酯，磁力搅拌，氮气保护下滴加0.57g(1.9mmol)2-(5-氨基-4-氯-2-氟苯基)异吲哚-1，3-二酮。滴毕，室温反应0.5h，然后加热至回流反应5h。减压脱溶得浅黄色固体，经柱层析得到0.68g目标产物，即1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-3-(2，6-二氟-苯甲酰基)脲，含量95％，m.p.214.6～217.7℃，收率75％。
1H NMR(CDCl3，ppm)δ：1.85(s，4H，cyclohexene)，2.45(s，4H，cyclohexene)，7.00～8.29(m，5H，ArH)，8.50(s，1H，Ar-NH)，11.00(s，1H，NH)。
实施例3：3-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-1，1-二丙基脲(表1中化合物19)的制备。
向装有干燥管的250mL三口烧瓶中加入80mL二氯乙烷和0.44g(1.48mmol)固体光气，搅拌溶解后氮气保护下滴加1.17g(4mmol)2-(5-氨基-4-氯-2-氟苯基)异吲哚-1，3-二酮和0.8g(8mmol)三乙胺的二氯乙烷溶液40mL，30min滴完，滴毕于室温反应30min，再次滴加0.4g(4mmol)二丙基胺和0.8g(8mmol)三乙胺的二氯乙烷溶液40mL，30min滴完，室温反应30min。将反应液水洗(100mL×3)，有机层依次用水、饱和碳酸钠水溶液和饱和盐水洗涤，经无水硫酸镁干燥，减压脱溶得到1.8g油状物，柱层析得浅黄色油状物0.76g，即3-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-1，1-二丙基脲，含量90％，m.p.97.5～99.3℃，收率55％。
1H NMR(CDCl3，ppm)δ：0.93～0.98(m，6H，CH3)，1.61～1.74(m，4H，CH2)，1.82(s，4H，cyclohexene)，2.41(s，4H，cyclohexene)，3.25～3.30(m，3H，NCH2)，6.94(s，1H，NH)，7.22～8.34(m，2H，Ar-H)。
应用实施例1：盆栽除草试验
准确称取样品，用适宜的溶剂溶解后，加少量乳化剂，再加蒸馏水定容至10ml采用适当喷雾机喷洒，折合单位面积药量为75gai/ha。在截面积64cm2的塑料盆钵中定量装土，压平，浇透水，选取籽粒饱满、大小一致的双子叶选用藜(Chenopodium album)、苘麻(Abutilon theophrasti)、凹头苋(Amaranthusascedense)，单子叶选用马唐(Digitaria sanguinalis)、稗草(Echinochloacrus-galli)、狗尾草(Setaria viridis)，分单、双子叶植物分钵栽种，各占钵面积的1/3，覆1cm厚细土并淋水，置于温室培养。待单子叶试材长至1叶1心期、双子叶试材长至2片真叶期，用药液进行苗后茎叶喷雾处理，试材播种次日进行苗前土壤处理。随后放回温室。15天后目测地上部生长情况，按照下式计算生长抑制率：
生长抑制率(％)＝100*(对照株高-处理株高)/对照株高
根据生长抑制率进行除草活性分级：
++，＞80％；+，80～50％；-，＜50％。
表2：盆栽除草试验结果
表2列出了本发明通式(I)所示的N-异吲哚二酮取代苯基脲类部分化合物对盆栽试材植株芽前土壤处理和芽后茎叶处理的抑制效果。本发明部分化合物，如表2中04、06、11、13、19、21、25等化合物，在75g ai/ha的剂量下苗前土壤处理或苗后茎叶处理时，对苘麻、藜、凹头苋等双子叶杂草表现出较好的除草活性，防效≥80％，对马唐、稗草和狗尾草等部分单子叶杂草也有一定的防效。
Claims (4)
1. N-异吲哚二酮取代苯基脲类化合物，其特征在于具有通式(I)所示结构：
其中
X为氢，氰基，甲基，氟或氯；
Y为氢，氟或氯；
R为(取代)苯甲酰基。
2. 根据权利要求1所述的N-异吲哚二酮取代苯基脲类化合物，其特征化合物为：
1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-3-(2，6-二氟-苯甲酰基)脲
1-[2，6-二氟苯甲酰基-3-(5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)(2，4-二氟苯基)脲
1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)苯基]-3-(2-氯-6-氟-苯甲酰基)脲
1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)苯基]-3-(2，6-二氟-苯甲酰基)脲
1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-3-(2，6-二氯-苯甲酰基)脲
1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)苯基]-3-(2，6-二氯-苯甲酰基)脲
1-[2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基]-3-(2，4-二氯-苯甲酰基)脲
1-苯甲酰基-3-(2-氯-5-(1，3-二氧-4，5，6，7-四氢-1H-异吲哚-2(3H)-基)-4-氟苯基)脲。
3. 根据权利要求1或2所述的N-异吲哚二酮取代苯基脲类化合物的制备方法，其特征在于：在溶剂中加入一定量的(取代)苯甲酰基异氰酸酯B，氮气保护下滴加相应量的中间体2-(5-氨基-2，4-二取代苯基)-4，5，6，7-四氢-2H-异吲哚-1，3-二酮A，滴加完毕，在一定的温度下反应1-12小时得到目标化合物(I)，上述反应中溶剂是二氯乙烷；摩尔比为A∶B＝1∶1.3；反应温度是所选溶剂回流温度；反应时间为5小时；具体合成路线如下：
4. 根据权利要求1或2所述的N-异吲哚二酮取代苯基脲类化合物的用途，其特征在于：在75g ai/ha的剂量下，对大多数阔叶杂草和部分单子叶杂草具有除草活性。
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| CNB2005100324251A CN100424074C (zh) | 2005-11-24 | 2005-11-24 | 具有除草活性的n-异吲哚二酮取代苯基脲类化合物 |
| PCT/CN2006/000690 WO2007059663A1 (fr) | 2005-11-24 | 2006-04-17 | Composes phenyluree a substitution isoindol-dione presentant une activite herbicide |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1228009A (zh) * | 1996-08-19 | 1999-09-08 | 巴斯福股份公司 | (z)－2－氯－3－[2－氯－5－(4,5,6,7－四氢－1,3－二氧代异吲哚二酮－2－基)苯基]丙烯酸乙酯的液体 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4439229A (en) * | 1981-06-29 | 1984-03-27 | Rohm And Haas Company | Substituted phthalimides herbicides |
| EP0077938A3 (en) * | 1981-10-23 | 1983-08-24 | Mitsubishi Kasei Corporation | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition |
| AU557324B2 (en) * | 1981-12-25 | 1986-12-18 | Sumitomo Chemical Company, Limited | Tetrahydro phthalimide compounds |
-
2005
- 2005-11-24 CN CNB2005100324251A patent/CN100424074C/zh not_active Expired - Fee Related
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2006
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1228009A (zh) * | 1996-08-19 | 1999-09-08 | 巴斯福股份公司 | (z)－2－氯－3－[2－氯－5－(4,5,6,7－四氢－1,3－二氧代异吲哚二酮－2－基)苯基]丙烯酸乙酯的液体 |
Non-Patent Citations (2)
| Title |
|---|
| 1-[5-(1,3-二氧-4,5,6,7-四氢-1H-异吲哚-2-基)苯基]-3-取代脲衍生物的合成与除草活性研究. 黄明智，程辟，黄可龙，任叶果，雷满香，马扬光，徐满才.有机化学，第25卷第8期. 2005 |
| 1-[5-(1,3-二氧-4,5,6,7-四氢-1H-异吲哚-2-基)苯基]-3-取代脲衍生物的合成与除草活性研究. 黄明智，程辟，黄可龙，任叶果，雷满香，马扬光，徐满才.有机化学，第25卷第8期. 2005 * |
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| WO2007059663A1 (fr) | 2007-05-31 |
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