ragweed ( in US soybeans ) and annual ryegrass ( Australian cereals ), often replacing the control once offered by older , higher-rate actives such as glyphosate and trifluralin . Figure 4 outlines the syntheses , required technologies and market information for pyroxasulfone and other AIs used in the mixtures above . Producers of thiobencarb who possess the thiochemistry capabilities would be able to identify what other technologies are required to produce pyroxasulfone . Others would be able to identify the capabilities needed to produce the mixture components sullfentrazone , flumioxazin , aclonifen and diflufenican benefitting from pyroxasulfone .
Figure 4 - Pyroxasulfone synthesis & commercial situation displayed in AgbioChem
Pyroxasulfone
Kumiai Chemical first launched the isooxazoline herbicide pyroxasulfone in 2011 as Sakura . In 2020 , sales of the AI amounted to $ 249 million , having seen substantial average growth of 18.9 %/ year since 2015 , significantly in advance of the overall herbicide market . Kumiai discovered pyroxasulfone through its investigations into the herbicide thiobencarb 1 , which has been on the market since 1970 and is used in rice production systems around the world . The company primarily maintained the thiocarbamate linkage in thiobencarb although converting the sulfide to a sulfone and the carbonyl to an imine contained in the oxazole ring ( Figure 3 ). Ultimately , the chlorobenzene and the diethyl amide functionalities were changed to improve efficacy . Kumiai has pursued a relatively large number of licensing opportunities , to the clear benefit of sales . It has strong representation in Japan and Brazil ( e . g . through Iharabras ), but less so in key cereal , soybean and maize markets , notably Australia and the US . BASF gained a licence to single formulations in the US , with FMC and Sumitomo Chemical gaining access to mixtures , including the PPO inhibitors sulfentrazone and flumioxazin , respectively . In addition , Bayer distributes the product in the single formulation Sakura , and new mixtures including Mateno Complete ( with aclonifen or diflufenican ) in Australia , while BASF and Summit Agro have introduced products more recently in Argentina . Indeed , the inclusion of proprietary AIs like pyroxasulfone can help maintain sales of off-patent mixture partners , a strategy clearly pursued by FMC for its sulfentrazone business . This broad licensing approach has significantly enhanced market reach . Moreover , the physiochemical properties , in combination with the resistance management capability ( VLCFA inhibition is a herbicidal MoA with very few resistant species ), fit a significant market need for a very efficacious weed resistance management tool . Indeed , pyroxasulfone sales have increased , in particular due to the need for control of herbicide-resistant small seeded-broadleaved and grass weed species , such as common
Acetamiprid
The nicotinamide insecticide acetamiprid was developed by Nippon Soda and launched in 1996 as Mospilan . The product was initially launched for use on fruit and vegetables , providing control of a broad range of pests , including Lepidoptera , Coleoptera and Hemiptera . Since this time , a significant off-patent market has emerged , with offerings from offpatent leaders UPL , Sipcam Oxon and Nufarm , who increasingly include the AI in innovative differentiated mixture formulations . Sales of the AI were relatively flat in the years between 2014 and 2018 at around $ 400 million / year , but regulation is expected to be a key driver for future sales growth in the EU . The major nicotinamides , clothianidin , thiamethoxam and imidacloprid , all lost their approval for outdoor uses in the EU in 2019 , and subsequently were not reapproved on approval expiry in 2019 and early 2020 . Acetamiprid does not face the same regulatory pressures as other products in the class , due to its more favourable environmental profile , and the product has been re-approved until the early 2030s in the EU . This represents a significant opportunity for acetamiprid in replacing lost uses
42 SPECIALITY CHEMICALS MAGAZINE ESTABLISHED 1981