Cyantraniliprole bromide is an o-formaminobenzamide insecticide discovered and developed in 2007 and marketed in 2012 by the original DuPont (cyantraniliprole and chlorantraniliprole were spun off to FMC at the end of 2017). Since the launch of the product, global sales have increased year by year, and its compound patent in China has expired on January 20, 2024, attracting the attention of many domestic companies.
Based on its unique mechanism of action, excellent product performance, high efficiency and broad spectrum, and good compatibility with non-target biosecurity and environment, bisamide insecticides have become the most concerned in the market after neonicotinoid insecticides, and are also the fastest growing insecticides in recent years, occupying an important market position in the field of lepidopteran pest control. Chlorantraniliprole, the outstanding representative of bisamide insecticides, has long surpassed imidacloprid and thiamethoxam to become the number one product in the global insecticide market.
At present, 9 bisamide insecticide products have been registered and marketed in the world, which are divided into three categories in terms of chemical structure: phthalamide biamide (flubenzamide and chlorofluflutraniliprole, etc.), o-formaminobenzamide (chlorantraniliprole, cyantraniliprole, tetrachlorantraniliprole, tetrazoltraniliprole, cyclobromotraniliprole and thipropaniliprole, etc.) and isobenzoylbenzamide (bromolufenoxanimidide, etc.).
Cyantraniliprole is considered to be an upgraded version of chlorantraniliprole, both have the same mechanism of action, and work by inhibiting fish nitine receptors, resulting in the uncontrolled release and consumption of calcium ions in the insect's body, inhibiting muscle contraction, and eventually paralyzing the insect's muscles until death. The biggest difference between cyantraniliprole and chlorantraniliprole is that the structure of chlorantraniliprole is a "chlorine group", and cyantraniliprole changes the "chlorine group on the structure of the benzene ring to a cyanide group" when the structure is optimized, so that it has stronger systemic activity, higher insecticidal activity and wider insecticidal spectrum, and has become the first bisamide insecticide that can control both chewing mouthparts and sucking mouthparts pests.
As a second-generation fish nitine receptor inhibitor, cyantraniliprole has quickly seized the market since its launch and has become the second largest product of FMC. Cyantraniliprole is suitable for many crops, has a wide range of insecticidal spectrum, and has both stomach toxicity and contact killing effects; It can not only control lepidopteran pests (the main type of pests), but also control Coleoptera and some dipteran and hemipteran pests, and can be used for crops such as corn, sugar cane, cotton, cereals, rice, fruit trees and vegetables. According to relevant research reports, cyantraniliprole has a high control effect on cotton aphid, peach aphid, whitefly and rice planthopper, and on dipteran insects such as orange fruit fly and fruit fly, as well as lepidopteran pests such as diamondback moth and cotton bollworm. The wide range of control of cyantraniliprole is also reflected in its ability to control underground pests such as grubs, ground tigers, and Spodoptera exigua, and cyantraniliprole also has greater market opportunities in terms of small insect control and underground pest control.
In addition to the conductive and osmotic effects of chlorantraniliprole, cyantraniliprole is more systemic and more thorough, and can be applied to the field through seed treatment, mixed soil application, direct root irrigation and foliar spraying. Cyantraniliprole bromide has been developed into a variety of dosage forms, such as suspension agent, water dispersible granules, bait and dispersible oil suspension, etc., and the current registration status in China is shown in Table 1. Among them, there are 3 registration certificates for the original drug, 5 registration certificates for single doses, and 4 registration certificates for compounding with trifluorophenyrimidine, pymetrozine, butyl etherurea and thiamethoxam.
The compound patent for cyantraniliprole in China expired on January 20, 2024, but cyantraniliprole is still protected by a number of patents in terms of raw materials, intermediates, formulation and use technology. For example, the original company's compound preparation patent "liquid preparation of carboxamide arthropod agent" (ZL2007800444994, expires on November 30, 2027) and the intermediate patent "Method for preparing 2-amino-5-cyanobenzoic acid derivatives" ZL2007800453902. It expires on December 18, 2027, which sets a very high entry threshold and commercial barriers for Chinese enterprises to develop cyantraniliprole-related products before the expiration of various patents in 2028. According to the statistics of the China Pesticide Industry Association, from 2008 to 2023, a total of 169 patents have been authorized and under review, and the main applicants are FMC, Jiangsu Rotam Chemical, Syngenta and BASF. So far in 2023, China has applied for 15 patents related to cyantraniliprole.
FMC has also carried out the brand layout of cyantraniliprole on a variety of crops in major countries around the three major brands
As a fish nitine receptor inhibitor, cyantraniliprole also does not avoid the problem of resistance, and relevant studies have shown that diamondback moth populations in some parts of Guangdong Province in China have developed moderate levels of resistance to the agent; In addition, some researchers used cyantraniliprole to screen relatively sensitive strains of gray planthopper for 25 generations, and the resistance factor increased to 1714 times to reach a medium resistance level. It can be seen that the continuous use of a single agent can induce pests to develop resistance. The combination of cyantraniliprole with insecticides with other mechanisms of action can delay the emergence and development of resistance, prolong the service life of pesticides, further expand the pest control spectrum, and reduce the cost of pest control. Multinational companies such as FMC and Syngenta have fully deployed the combination of cyantraniliprole with neonicotinoids and pyrethroid insecticides. In addition, cyantraniliprole can also be compounded with emamectin benzoate, avermectin, chlorfenapyr, ethanthinil, pyripropyl ether, lice cardia, cyanopronidine, indoxacarb, ethylspinosabad and other active ingredients. In addition, the combination of cyantraniliprole with fungicides such as isothiamide and fluazole amide for seed treatment can further expand the development and application of cyantraniliprole. It is foreseeable that after the patent expires in 2024, the compound dosage form will be more abundant, and the multi-compound will dominate the market.
Looking at the global market, since its first listing in Argentina in 2012, FMC has registered cyantraniliprole products in more than 50 countries around the world, covering major agricultural producing countries around the world, including Brazil, China, India, Japan, the United States, Canada, Australia, etc., involving soybeans, grains, rice, rapeseed, cotton, fruits and vegetables and other crop sectors. Especially in the field of fruits and vegetables with relatively high economic added value, the market scale of cyantraniliprole is gradually expanding due to its broad-spectrum high efficiency and wide application range. In the field of rice lepidopteran pest control, because the ** of cyantraniliprole is higher than that of Kangkuan (chlorantraniliprole), the competitive advantage of cyantraniliprole has not yet been reflected in the rice sector. It is expected that after the expiration of China's compound patent in 2024, domestic enterprises will accelerate the layout of production capacity, the cost will sink, and the cost-effectiveness of cyantraniliprole in rice will gradually appear.
Cyantraniliprole bromocarniliprole is a bisamide insecticide with excellent performance, which has stronger systemic activity and higher insecticidal activity than chlorantraniliprole. The insecticidal spectrum is wider, and it can prevent and control chewing mouthparts and stinging and sucking mouthparts pests at the same time, annihilate large insects and small insects, and achieve the purpose of one drug and multiple prevention. Through abundant compounding methods, the control scope of pesticides can be expanded, and the emergence and development of pest resistance can be delayed.
The comprehensive layout and patent protection of cyantraniliprole-related compound brands by multinational companies have greatly increased the complexity of preparation registration for Chinese enterprises. It is foreseeable that the promotion and application of cyantraniliprole-related compound products will be an important trend. Enterprises that have already started product layout should do a good job in the precise positioning of crops and targets, and launch differentiated compounding solutions to seize market share. Judging from the market layout in recent years, pest control in the field of cash crops such as fruits and vegetables is an important sales growth point for cyantraniliprole, and the market potential is huge. After the expiration of the patent, it remains to be seen whether cyantraniliprole can continue the legend of chlorantraniliprole.