New driver to yield increase in agricultural production: Production and market analysis of BASF’s innovative herbicide trifludimoxazin

• BASF’s patented herbicide trifludimoxazin granted registration in three countries

• Trifludimoxazin is manufactured in India, with stable production and sustained growth in 2020

• Market prospect of trifludimoxazin over flumioxazin and pyroxasulfone

The innovative herbicide trifludimoxazin is the first herbicide with a new mode of action that has emerged over the last 20 years, which reveals an excellent effect of control of a large variety of grassy weeds and broad-leaved weeds. After the first product registration of trifludimoxazin in Australia in May 2020, its commercialization rose rapidly worldwide, adding a new blockbuster product to the PPO inhibitor herbicide market. The market release and popularization of trifludimoxazin are expected to bring about a new driver to the yield increase in agricultural production.

Trifludimoxazin, developed in the code name of BAS 850 H, is a triazone herbicide created by BASF, being made public in 2014. Its chemical name is 1,5-dimethyl-6-sulfanylidene-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-1,4-benzoxazin-6-yl)-1,3,5-triazinane-2,4-dione; CAS number is 1258836-72-4; Molecular formula is C16 H11F3N4O4S. The structural formula is as follows:

Registration Overview

So far, trifludimoxazin formulation products at a technical level have been granted registration in Australia, Canada and the United States (US).

On May 28, 2020, BASF’s novel herbicide trifludimoxazin technical was granted registration in Australia for the first time anywhere in the world. On July 1 the same year, BASF’s mixture product Voraxor - 125.0g/L trifludimoxazin + 250.0g/L saflufenacil SC was also granted registration in Australia for use in weed control in commercial, industrial and public fields, agricultural facilities and courtyards as well as for application to weed prevention and control at pre-sowing of barley, in fallow period and non-crop areas, leisure facilities, pastures before forestation and at the pre-sowing of wheat.

On January 21, 2021, Canada granted registration of trifludimoxazin 99.2% TC, 500g/L SC and 375 g/L trifludimoxazin • saflufenacil SC for use in weed control for barley, field corn, pea (dry land), soybean, wheat (including durum wheat, spring wheat and winter wheat) and fallow land.

On May 28, 2021, the US granted registration of 99.2% technical and a 41.53% suspension agent (trade name: TIREXOR) of trifludimoxazin for use in the control of broad-leaved weeds and grassy weeds in corn, legume vegetable, small grain, peanut, sorghum, soybean, citrus, cotton and sunflower fields. In case TIREXOR is used for soil surface treatment before planting of corn, soil treatment before planting or for control of broad-leaved weeds and grassy weeds before seedling, the dosage can be as much as 1.0 fl oz/A. 

Export and Sales Analysis 

There is no available data for sales before 2019. That year, 1.64 tons of trifludimoxazin were sold in Australia, where the price of formulation product was US$2.51/kg; 0.02 tons were sold in other Asian countries, where the price of formulation product was $3.68/kg.

India's Export 

In 2018, Deccan India exported 60kg of the samples of trifludimoxazin technical to BASF USA; in 2019, Deccan exported 45kg to BASF Germany; In 2020, Deccan exported 10.2 tons to Indonesia, 0.3 tons to the United States and 50kg to Germany, at a unit price of $273,955.5 per ton. In the first quarter of 2021, Deccan exported 13.6 tons to Indonesia at a unit price of $269,041.8 per ton.

Indonesia's Export

In 2020, Indonesia BASF exported 19.14 tons of Voraxor (trifludimoxazin 125.0g/L + saflufenacil 250.0g/L SC) to Australia in 2020, with a total export value of $1,427,205 at a unit price of $74,566.6 per ton. In the first quarter of 2021, Indonesia exported 30.62 tons of Voraxor (trifludimoxazin 125.0g/L + saflufenacil 250.0g/L SC) to Australia, with a total export value of $2,060,668 at a unit price of $67,298.1 per ton.

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Production Process and Intermediate

According to published literature, the production process of trifludimoxazin is as follows:

5-Fluoro-2-nitrophenol is used as the initial material, which is processed via reduction, bromodifluoroacetic acidification and annulation, resulting in an intermediate, which then further results in isocyanate via nitrification, alkylation, nitro-reduction and photochemical reaction; and finally, the target product is obtained by cyclization. 

5-Fluoro-2-nitrophenol can be made using 2,4-Difluoro-1-nitrobenzene (Yongtai Technology being a prime Chinese supplier), added with alkali. In addition, the two fluorine atoms in the molecular structure of trifludimoxazin represent a highlight of the product, which can be obtained by reduction of trifluorochlor oethylene into halogenated ethyl difluoroacetate. It is said that Sinochem Lantian, a leading fluorine chemical enterprise in China, can realize this chemical process. According to a research, only one factory in India, which is Gujarat Fluorochemicals Limited (GFL), is importing trifluorochlor oethylene from Jiangsu Blue Planet CO., Ltd, from which 20 tons were imported in 2019 and 44 tons in 2020, at an average price of $11,000 per ton.

The main chemical structure of trifludimoxazin being similar to flumioxazin

Following technical information is provided by Hangzhou Jireh Standard Technology Co., Ltd (www.jirehhz.com):

Flumioxazin was launched by Sumitomo Chemical in 1993, being a PPO inhibitor just like trifludimoxazin, which are both of contact toxicity via foliar uptake. After the target buds or leaves of plants have contact and absorption of the agent, the chlorophyll biosynthesis is interfered, thus photosynthesis is affected, and plants will wither and die out rapidly. The effect and symptoms of the two agents are basically the same, where the susceptible weeds will appear to be damaged, with signs of blight within a few hours of exposure and will then die in about three days. Trifludimoxazin is not easily volatile and will remain stable at normal temperatures. Its structure is similar to flumioxazin, they are both not easily dissolvable in water. Their solubility is 1.78 mg/L and 0.786 mg/ L respectively but is higher in acetone and tetrachloromethane.

Trifludimoxazin and flumioxazin have a similar range of action. They can be both used for control of annual grassy weeds and broad-leaved weeds in soybean, uncultivated land, sugarcane, cotton, corn, grain, peanut, fruit and vegetable fields before sowing, after sowing and before seedling. The difference is that trifludimoxazin has good control over some PPO inhibitor-resistant weeds, such as amaranthus and ambrosia. In addition, the aerobic half-time of trifludimoxazin is about 50 days, which is relatively difficult for soil adsorption. After use, residue mainly remains in the upper 15 cm layer of the soil, which is of certain soil residual activity and can inhibit weed germination by repetition, thus being highly safe for the next-stubble crop. The half-time of flumioxazin is about 20 days, which is also of certain residual activity in the soil.

Flumioxazin has been granted registration in quite a few countries including Brazil, the United States and China. Brazil is the main market for the product. According to Phillips McDougall, in 2018 the global sales of the product was $380 million, ranking 12th in herbicides worldwide. The sales increased twice over five years ago with Brazil accounting for about 28% of global sales.

So far, there have been 47 flumioxazin product registrations with 19 technicals in China. The main registrations are wettable powder, suspension concentrate, water dispersible granule and emulsifiable concentrate. Due to the late development of trifludimoxazin, all registrations are currently suspension concentrates.

Is pyroxasulfone more worthy of attentions from Chinese manufacturers compared with trifludimoxazin?

Pyroxasulfone is a novel broad-spectrum and high-activity herbicide used for soil treatment before seedling, as developed by Kumiai Chemical of Japan. The crops for application and objects of control of pyroxasulfone and trifludimoxazin are somewhat the same and overlap, covering corn, cotton, peanut, wheat and sunflower. The controlled objects include grassy weeds such as green bristle grass, crabgrass and barnyard grass as well as broad-leaved weeds such as amaranth, datura, solanum and abutilon. Research reveals a same or even better effect of control by use of 1/10 of the dosage of s-metolachlor and acetochlor.

The compound patent of pyroxasulfone is about to expire on February 6, 2022, whilst the related process patent is expected to expire between 2027 and 2032. Since its launch, pyroxasulfone has been highly valued and regarded. To expand the sales of the product, Kumiai Chemical entered into a cooperative agreement respectively with BASF, Valent, Bayer and others to promote the product. Till now, the product has been granted registration in Australia, the United States, Canada, South Africa and Brazil. Up to now, only Shanghai Qunli Chemical Co., Ltd owns a registration of pyroxasulfone TC and SC in China. It is expected that when the patent of the compound expires, pyroxasulfone will become an extremely popular product in the herbicide market. At present, the price of the technical of multinational companies is at around Yuan1.3 million. Chinese domestic enterprises have claimed that they would sell at Yuan650,000 once the patent expires.