Cycloheptan, English common name: Cinmethylin, trade name: Luximo, Luximax, etc., development code: BAS 684 H (BASF). It is a benzyl ether herbicide developed by BASF with a unique chemical structure and novel mechanism of action, focusing on the control of resistant gramineous weeds.
Scope of application
Cycloheptane is a pre-emergence herbicide, which has a long-lasting effect, and is used in winter cereal fields to control many gramineous weeds, including the difficult to control large spike and ryegrass. Studies have shown that cycloheptane is particularly effective against ryegrass and provides a long-lasting effect. Ryegrass is the main refractory weed encountered in large-scale cultivation in many countries around the world.
Cycloheptane can also be used to control important weeds in paddy fields, such as barnyard weeds, duck tongue grass, heteromorphic sedge, etc. It was found that rice had strong resistance to cycloheptane, which was metabolized into hydroxyl derivatives when it entered rice, and combined with glycosides in rice to form conjugated compounds and lost toxicity.
Mechanism of action
Cycloheptanol is a selective inhibitor of acyl carrier protein (ACP) fatty acid thioesterase (FAT), which destroys cell membranes and leads to weed death by inhibiting fatty acid biosynthesis. It is mainly absorbed by the shoots and roots of weeds at the seedling stage, and is transmitted to the growth points of roots and shoots through the xylem, hindering the mitosis of meristems and causing plant death.
BASF notes that FAT is essential for the development and function of plant cell membranes. This inhibition can disrupt the germination and occurrence of grasses and weeds. The company believes that cycloheptane has the potential to be the backbone of effective and sustainable solutions for the control of grasses, through the rotation of herbicides with multiple mechanisms of action to jointly combat resistant weeds. It has been reported that cycloheptane has no known cross-resistance and can be used for comprehensive weed management.
In 2020, cycloheptane received the first new mechanistic classification since 1985 from the International Herbicide Resistance Action Committee (HRAC). It is the first active ingredient in HRAC "Group Q" or "Group 30", the other active ingredient is Methiozolin, both of which are benzyl ether compounds.
Registration
Registration information in China, the European Union, and the United States: No registration information has been queried. There have been 9 products based on cycloheptane in China. As of November 11, 2009, the registration of all these products has expired.
UK Registration Information:
Australian Registration Information:
Patent Information
There are also a number of domestic enterprises that have applied for patents for compounding with cycloheptan, including:
Synthetic routes
α-pinene was used as the starting material to synthesize cycloheptane.
reference
1. Wang Canming, Cheng Chunsheng, Yan Shiqin. Synthesis of Eucalyptol Herbicide Cycloheptyl Ether[J]. PESTICIDES, 1996, 35(3): 34-35.
2. Bai Yaluo. Cycloheptane re-emerges from the rivers and lakes with a new mechanism of action[EB/OL]. http://jsppa.com.cn/news/yanfa/5519.html. 2021-09-28.
3. Li Yanjun, He Hongwu. Research Progress on 1,4-Eucalyptol Derivatives with Herbicidal Activity[J]. Agrochemicals, 2004, 43(3): 101-103.
4. Wu Aiguo, Wang Dongming, Wu Dingbang, etc. Experimental study on weed control by cycloheptyl ether in paddy field[J]. Agrochemicals, 1995, 34(12): 41-42.