Crops will inevitably be infested by diseases, insect pests and weeds during the production process. The use of pesticides can not only effectively prevent and control diseases, insect pests and weeds, but also greatly improve the appearance and yield of crops. In recent years, many pesticide varieties have withdrawn from the market due to environmental and safety issues. The market calls for more new pesticides that are safe for human beings and friendly to the environment.
This article summarizes 16 newly registered and marketed pesticide varieties in the world, including 5 herbicides, 4 insecticides, 5 fungicides, and 2 nematocides. For 16 new pesticide varieties, the mechanism of action, biological activity, patent application, registration and market development are introduced in order to provide reference for the innovative research and development of pesticide companies and R&D personnel in my country.
Herbicides
The five newly registered and marketed herbicides are triflumezin, beflubutamid-M, clomazone, cyclopyranil, and triazosulfotrione.
.1 Trifludimoxazin (trifludimoxazin)
Trifludimoxazin is a new triazinone herbicide developed by BASF. Its English common name is trifludimoxazin, and its development code is BAS 850H. Its CAS registration number is 1258836-72-4, and its structural formula is shown in Figure 1.
Figure 1. Structural formula of triflumezin
Triflumezin is classified as Group E by the Herbicide Resistance Action Committee (HRAC). It is a protoporphyrinogen oxidase (PPO) inhibitor that causes weeds by interfering with chlorophyll biosynthesis die. A few hours after spraying, susceptible plants showed signs of damage and died within 3-5 days. Weed seedlings usually grew to the soil surface or died shortly after emergence.
Triflumezin is suitable for many crops and has a wide weeding spectrum. It can be used in grains, corn, soybeans, peanuts, citrus, pome fruit and other crops to control grass weeds and broad-leaved weeds, such as quinoa, pigweed Grass, ryegrass , cat ear grass, etc. It has good quick-acting properties and long-lasting effect. It can not only quickly control the weeds that have occurred, but also provide a long-lasting effect on various weeds for up to 12 weeks. Triflumezin can also be used as a resistance management tool to control some important resistant weeds, such as Amaranthus (Amaranthus spp.), ragweed (Ambrosiaspp.), etc., as well as difficult-to-control ryegrass. BASF claims that it is not only a PPO inhibitor, but also can control weeds that are resistant to PPO inhibitor herbicides.
BASF applied for a European patent (EP2443102) for compounds of the general formula including triflumezin, and submitted a PCT application with the international publication number WO2010145992A1 on June 11, 2010. The patent has been authorized by China, the United States, Australia, Japan, South Korea, Italy and other countries. The Chinese invention patent application number is CN201080027493.8.
In 2020, triflumezin technical (trade name Tirexor) and its compound suspension product Voraxor (125 g/L triflumezin + 250 g/L saflufenacil) have been registered in Australia successively, valid for 5 years . Voraxor is used for wheat, durum wheat, barley, etc. to control annual ryegrass; it is also used in non-agricultural fields, such as forest vegetation, weeding before construction of idle land, weeding around buildings, and weeding in public areas or gardens.
At the beginning of 2021, Canada intends to approve the registration of the technical triflumezin (Tirexor), the triflumezin-based single-dose suspension product Vulcarus (500 g/L) and the compound product Voraxor. Preparation products are used in barley, corn, peas, soybeans, wheat, lentils, and fallow land, etc., to prevent and control swine worms, Kochia, vines, root grass , retroflexus , rapeseed seedlings, buckwheat vines, Wild mustard, etc., and can effectively control the secondary occurrence of weeds.
In May 2021, the technical product of triflumezin and its suspension product obtained U.S. Environmental Protection Agency approval, and the preparation products are used in cereals (except rice), nut trees, peanuts, legume vegetables, citrus, pomegranate, etc. And non-agricultural fields, such as afforestation areas, industrial greening, natural grass, etc., to control broad-leaved weeds and grass weeds, and can be applied before or after emergence.
BASF has also submitted registration applications to some countries in Asia and the Americas to further expand the market for triflumezin.
.2 Beflubutamid-M
Beflubutamid-M was developed by Ube Industries, Japan, and Stahler (now owned by FMC) obtained its global development rights in 2007.Its CAS registration number is 113614-09-8, and its structural formula is shown in Figure 2.
Figure 2 Beflubutamid-M structural formula
Beflubutamid-M is a phenoxyamide herbicide, which is the S-isomer isolated from the herbicide beflubutamid. Beflubutamid-M is classified into Group F1 by HRAC. By inhibiting weed phytoene dehydrogenase, it destroys carotenoid biosynthesis, causes plant leaves to turn white, and then stops growing.
is similar to flubutamid, and beflubutamid-M is mainly used for controlling broad-leaved weeds in grains (barley, wheat, etc.). A large number of activity studies conducted by FMC have confirmed that beflubutamid-M has a stable structure and its herbicidal activity is at least 1,000 times that of the R-isomer. Therefore, its dosage is lower, and its impact on the environment and non-target organisms is smaller, and it is expected to become an important herbicide variety in grain fields.
Japan Ube Industries Co., Ltd. applied for the European patent (EP0239414) for the general formula compound including beflubutamid-M, and the application date was March 27, 1987. The patent has been authorized by Japan and the United States.
.3 Bixlozone (bixlozone)
Bixlozone is an isoxazolinone herbicide developed by FMC Corporation of the United States. Its English common name is bixlozone, its trade name is Isoflex, and its development code is F9600. Its CAS registration number is 81777-95-9, and its structural formula is shown in Figure 3.
Figure 3 Dichloroclomazone structural formula
Dichloroclomazone is classified into Group F4 by the Herbicide Resistance Action Committee (HRAC), deoxy-D-xylulose phosphate synthase inhibitors, by destroying plastids The biosynthesis of isoprene hinders the synthesis of carotenoids, causing susceptible plants to fail to perform photosynthesis normally, thus stopping growth and dying.
Dichloroclomazone is systemic, absorbed through plant roots and shoots, and conducted in plants via xylem. Formica has carried out extensive field experiments in different regions and under different conditions. Tests have proved that clomazone is suitable for many crops, such as orchards, vegetables, cotton , rice, sugar beet, barley, wheat, rapeseed, etc.; It has a good effect and is effective against difficult-to-control weeds such as ryegrass; its application window period is long and its persistence is good. It can be applied before emergence, early after emergence or when sowing. It not only has good control effect on weeds that have occurred, It also has a certain control effect on weeds that occur later, and the duration of effect is as long as 12 weeks; it can be used for resistance management and is effective for some resistant weeds. In addition, the clomazone product is currently the only herbicide that can be used in the three major winter crops of wheat, barley and rapeseed, providing greater flexibility for crop rotation.
Dichloroclomazone has a similar chemical structure to FMC's old variety of clomazone, only the benzene ring differs by one chlorine atom. When FMC applied for the patent of clomazone, it also disclosed the compound dichloroisomazone Oxadiazone. The invention patent published by FMC is US4405357, and the application date was May 11, 1981.
In April 2020, FMC's 400 g/L dichloroclomazone suspension concentrate (trade name Overwatch) was registered in Australia and will be launched in the 2021 winter planting season. Overwatch is effective against annual ryegrass (Lolium multiflorum), and can control Miscanthus weeds (Vulpia spp), Bifora testiculata, endive (Sonchus oleraceus), cow parsnip (Heracleum sphondylium), loosestrife (Lythrum hyssopifolia ) Wait for weeds.
On July 9, 2021, the Pesticide Control Institute of the Ministry of Agriculture and Rural Affairs of the People's Republic of my country announced the list of the seventh batch of new pesticide products to be approved for registration in 2021, and FMC's 96% dichloroclomazone TC and 36% suspension concentrate were included in it . The preparation product will be used to control annual broad-leaved weeds in winter wheat fields.
.4 Cyclopyranil
Cyclopyranil is a pyrazole herbicide developed by Japan Kyoyu Agriculture Co., Ltd., with the development code KY-1211. Its CAS registration number is 1651191-47-7, and its structural formula is shown in Figure 4.
Figure 4 Cyclopyranil structural formula
Cyclopyranil has pyrazole pyridine structure, which is similar to the herbicide pyraclonil which also has this structure, and its mechanism of action is protoporphyrinogen oxidase (PPO) inhibitor.Cyclopyranil is effective against a variety of annual weeds and perennial weeds , and it is effective against broad-leaved weeds such as Sagittarius Nakano, Moshangcai, Budapest, barnyardgrass, bermudagrass, and firefly rush, gramineous weeds, and sedges in rice fields. Grass family weeds, as well as dry field crops such as Solanum , Abutilon , Ragweed, Annual Capsule, Purslane , Popona , Chinese crabgrass, Chenopodium, Kochia, etc. Control effect; at the same time, it also has high activity against high-leaf weeds and sulfonylurea herbicide-resistant weeds. Field soil treatment, stem and leaf spray treatment can be used.
Japan's KYOYU Agricultural Company applied for a European patent (EP3031806) for general formula compounds including cyclopyranil compounds, and submitted a PCT application with the international publication number WO2015020156A1, and the filing date was August 7, 2014. The patent has been authorized by China, Australia, Brazil, Italy, Japan, South Korea, Russia, and the United States.
.5 Triazole sulfotrione (tripyrasulfone)
Triazole sulfotrione is a p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor herbicide developed by Qingyuan Nongguan. The English common name is tripyrasulfone, and the development code is QYR301 , trade names Daoyu, Daoguying, Saidan, etc. Its CAS registration number is 1911613-97-2, and its structural formula is shown in Figure 5.
Figure 5. Structural formula of triazole sulfotrione
Triazole sulfotrione, by inhibiting the activity of HPPD in plants, hinders the conversion process of p-hydroxyphenylpyruvate into homogentisic acid , and plastoquinone cannot be synthesized normally, thereby affecting Carotenoid biosynthesis in plants leads to leaf bleaching and eventual death.
Triazole sulcotrione is safe to rice seedlings and is suitable for rice transplantation and direct seeding. Its weeding spectrum is wide, and it has high activity on barnyardgrass (Echinochloa crus-galli), Qianjinzi (Leptochloa chinensis), duck tongue grass (Monochoria vaginalis), sweet intestines (Eclipta prostrata), etc. There is no cross-resistance to herbicides currently commonly used in paddy fields, such as clofenac-methyl, penoxsulam and quinclorac . It is also an excellent resistance management tool, which can effectively control the Echinochloa weeds that are resistant to ALS inhibitors and ACCase inhibitors in rice fields, and the daughter of the genus Echinacea that is resistant to ACCase inhibitors. Triazosulfotrione has a certain resistance to rain erosion, so there is no significant correlation between herbicidal activity and the interval of rainfall after drug application.
Qingdao Qingyuan Compound Co., Ltd. applied for the European patent (EP3293178) for the general formula compound including the triazole sulcotrione compound, and submitted the PCT application, the international publication number WO2017113508, and the application date was December 31, 2015. The patent has been authorized by China, Australia, Canada, Japan, South Korea, Russia, and the United States.
In 2020, Jiangsu Qingyuan Nongguan Weed Control Co., Ltd. obtained registration in my country for 95% triazole sulcotrione TC, 6% dispersible oil suspension concentrate, and 28% propanil·triazole sulfotrione dispersible oil suspension concentrate . The preparation product is used for controlling barnyardgrass in paddy field.
Insecticides
Newly registered and marketed insecticides are: Methopridine, benzpyrimoxan, flupyrimin, oxazosulfyl.
.1 Benzpyrimoxan
Benzpyrimoxan is a new type of insecticide developed by Nippon Norochemical Co., Ltd., with the development code NNI-1501. Its CAS registration number is 1449021-97-9, and its structural formula is shown in Figure 6.
Figure 6 Benzpyrimoxan structural formula
Benzpyrimoxan has low toxicity, has little effect on non-target organisms such as pollinators and beneficial arthropods , and has no mutagenicity. Its mechanism of action is still unclear, but the development company is based on its unique chemical structure (the pyrimidine group contains benzyloxy and cyclic acetal), and the existing insecticides fipronil, etofenprox, , buprofezin , imidacloprid , etc. have no cross-resistance, etc. It is speculated that they have a novel mechanism of action. Benzpyrimoxan is suitable for insecticide resistance management and integrated pest management.
The results of laboratory tests carried out by Japanese pesticides show that: using the conventional dipping method, benzpyrimoxan has high activity against rice planthopper nymphs, and also high activity against black-tailed leafhoppers; the activity against other Hemiptera pests is lower than The activity against rice planthopper has extremely high selectivity to rice planthopper; the agent has no cross-resistance with existing insecticides, and the activity against rice planthopper resistant strains and sensitive strains is equivalent. The results of the field efficacy test showed that when the dosage of the active ingredient was 50-75 g/hm2, benzpyrimoxan had a better control effect on resistant brown planthopper and white-backed planthopper ; It can control the population growth, and the duration of effect is more than 3 weeks.
Nippon Nosho Co., Ltd. applied for European patent (EP2810939) for general formula compounds including benzpyrimoxan compound, and submitted PCT application, international publication number WO2013115391A, application date on February 1, 2013. The patent has been authorized by China, Argentina , Australia, Canada, Brazil, Japan, South Korea, and the United States.
Nippon Pesticides is actively developing the global market for benzpyrimoxan. In September 2020, two benzpyrimoxan-based products, Orchestra Flowable and Orchestra Powder, made their debut in Japan, both of which are used in rice to control rice planthoppers and leafhoppers , etc. Tests have proved that: Orchestra has a long-lasting effect, excellent control effect on rice planthoppers, and can control rice planthoppers resistant to other insecticides; Orchestra is safe for humans, animals, aquatic organisms, natural enemies and other beneficial organisms. The risk of phytotoxicity of rice is low.
Japanese pesticides have also submitted registration applications to India and are expected to be launched in Japan in 2021 and in India in 2023.
.2 spiropidion (spiropidion)
spiropidion is a spirotetronic acid insecticide developed by Syngenta , its English common name is spiropidion, and its development code is SYN546330. Its CAS registration number is 1229023-00-0, and its structural formula is shown in Figure 7.
Figure 7 Structural formula of methoxetine
methoxetine is the fourth product developed and marketed after spirodiclofen, spiromesifen and spirotetramat (spirotetramat) Spirotetraketoacid insecticides contain keto-enol interconversion structure in the molecule, and the chemical structure is similar to that of spirotetramat. The International Insecticide Resistance Action Committee (IRAC) classifies them in category 23: Acetyl-CoA carboxylase (ACCase) inhibitors, tetronic acids and tetronic acid derivatives. The mechanism of action of methoxetine is a lipid biosynthesis inhibitor. By inhibiting the activity of ACCase in the process of fat synthesis in the pest, it destroys the synthesis of lipid, blocks the normal energy metabolism of the pest, and finally causes the death of the pest.
Methidine has two-way, systemic conduction properties, conducts apically and basally through the xylem and phloem of plants; in addition, it also has vertical osmosis . After spray application, Metoperidine can not only effectively control foliar pests, but also effectively protect new stems, leaves and parts that are not easily accessible by the liquid medicine, providing protection for the whole plant of the crops. Tests have proved that with the aid of the adjuvant, the two-way conduction of methotrexate is excellent and rapid. After a few hours of application, the parent and diketone metabolites are widely and efficiently distributed throughout the plant.
Methidine is suitable for many crops, including apples, pears, grapes, citrus, tomatoes, leguminous plants, cotton, potatoes, etc. It has a wide control spectrum, including aphids , whitefly , psyllid , shield scale, soft scale, spider mite, rust mite, red spider, peach aphid , tobacco whitefly, cotton aphid and other pests or harmful mites. According to Syngenta's introduction, methotrexate has a good control effect on difficult-to-control piercing-sucking mouthparts pests, including whitefly , aphids, and psyllids, and is effective against some resistant pests, such as neonicotinoids. Insecticide-resistant piercing-sucking mouthparts are effective. Methoxyphene provides a new and effective alternative agent for agricultural production. Methoxyphene has low toxicity and is safe to mammals, pollinators and beneficial organisms, and can be used in IPM projects.
Syngenta applied for a European patent (EP2369934) for compounds of the general formula including methoxetine, and submitted a PCT application with the international publication number WO2010066780 on December 9, 2009.The patent has been authorized by China, Argentina, Australia, Brazil, Canada, Germany, Japan, South Korea, Russia, and the United States.
From 2019 to 2020, Syngenta's methoxetine technical product and its preparations were successively registered in Guatemala , and the preparations were launched in Guatemala at the end of 2020 under the trade name Elestal Neo. In December 2019, methoxetine was registered in Paraguay, and it is expected to be launched in Paraguay in 2021. Registered in Australia in February 2020.
In the next 6 years, Syngenta plans to launch methoxetine products in more than 60 countries around the world. The company plans to launch the methoxetine ethyl ester product in Brazil in 2023, and the registration in Brazil is currently in progress. Gowan Corporation of the United States obtained from Syngenta the exclusive right to develop and sell Methoxyphenidate 300 SC in the US and Canadian markets.
.3 Flupyrimin
Flupyrimin is an insecticide newly developed by Meiji Seika Co., Ltd., Japan, with the development code ME5382. Its CAS registration number is 1689566-03-7, and its structural formula is shown in Figure 8.
Figure 8 Flupyrimin structural formula
Flupyrimin has low toxicity to mammals and aquatic organisms (fish, Daphnia magna and algae ), etc. It is relatively safe to pollinating insects, and its safety is better than imidacloprid, flupyridone, and Flupyrimin Aminonitrile , trifluoropyrimidine and other insecticides that act on nicotinic acetylcholine receptors. In addition, flupyrimin has no teratogenicity and genotoxicity.
Flupyrimin acts on nicotinic acetylcholine receptors, the mechanism of action is the same as cyclopyrid and trifluoropyrimin, and is a nicotinic acetylcholine receptor antagonist. Flupyrimin is selective for nicotinic acetylcholine receptors in animals, and is safe for non-target animals; the mechanism of action and binding site are different from the neonicotinoid insecticide imidacloprid, and flupyrimin is effective against imidacloprid-resistant pests. According to the chemical structure and characteristics, combined with the efficacy of stem and leaf spray and soil irrigation, the development company speculates that flupyrimin has contact killing and gastric toxicity activities, as well as systemic properties, and can be transmitted across layers.
Flupyrimin is suitable for many crops and has a wide insecticidal spectrum. It can be used in rice, wheat, vegetables, fruits, and non-agricultural fields to control Hemiptera pests cotton aphid, whitefly, planthopper, black-tailed leafhopper, Lygus chinensis and small Persian bugs, Lepidoptera pests diamondback moth , beet armyworm, Coleoptera pests rice negative mudworm, rice water weevil, Thysanoptera pests thrips , and Diptera pests housefly, etc. Multiple categories of pests. The results of indoor experiments showed that the insecticidal activity of flupyrimin against western flower thrips, brown planthopper and black-tailed leafhopper was equivalent to that of imidacloprid, and it was effective against housefly, diamondback moth, brown planthopper, white-backed planthopper, negative mudworm, red beard The insecticidal activity of mirid bugs is relatively high, but the insecticidal activity against cotton aphids and whitefly is relatively low. The field test results show that flupyrimin can effectively control the stem borer in the early stage of rice planting and the rice planthopper in the middle and late stage after one application of flupyrimin, and can control rice pests resistant to imidacloprid, and is safe for pollinators.
Meiji Seika Pharmaceutical Co., Ltd. applied for the European patent (EP2633756) for the general formula compound including the flupyrimin compound, and submitted the PCT application, the international publication number WO2013129688A1, and the application date was February 28, 2013. The patent has been authorized by China, Argentina, Australia, Brazil, Canada, Italy, Japan, South Korea, and the United States.
In March 2018, Meiji Seika and Arysta signed an agreement, and Arysta obtained the exclusive right to develop and sell the product in India. At present, the flupyrimin single agent and the compound preparation with thiabendazole, spinosad and tricyclazole are registered in Japan, and they are used in rice and its seedlings to control a variety of thorn-sucking mouthparts pests, and also treat Chilo borer , rice negative mud worm, stinkbug. Registration of flupyrimin in India and South Korea is ongoing.
.4 Oxazosulfyl
Oxazosulfyl is a new type of benzoxazole insecticide developed by Sumitomo Chemical Co., Ltd., with the development code S-1587. Its CAS registration number is 1616678-32-0, and its structural formula is shown in Figure 9.
Figure 9 Oxazosulfyl structural formula
Oxazosulfyl is the first benzoxazole insecticide, and its molecule contains a sulfonyl pyridine fragment, which is more common in sulfonylurea herbicides.Based on the novel chemical structure of oxazosulfyl, the development company predicts that it has a unique mechanism of action. The results of the
biological activity test showed that at a mass concentration of 500 mg/L, oxazosulfyl was more than 90% effective against cotton aphids (Aphis gossypii), brown planthopper (Nilaparvata lugens), and curlworm (Adoxophyes oranafasciata), and against diamondback moth (Plutella xylostella) has a control effect of over 80%, over 95% against Culex pipienspallens, and 100% against housefly (Musca domesticea); at a concentration of 50 mg/L, it is effective against SBPH ( Laodelphax striatella) and white-backed planthopper (Sogatella furcifera) have achieved 100% control effect.
Japan Sumitomo Chemical Co., Ltd. applied for European patent (EP2938601) for general formula compounds including oxazosulfyl compound, and submitted PCT application, international publication number WO2014104407A1, application date on December 26, 2013. The patent has also applied for compound patent protection in China, Australia, Brazil, Canada, Europe, Italy, Japan, South Korea, Russia, the United States and other countries and regions.
Oxazosulfyl is registered for use in rice with the trade name ALLESTM.
Fungicides
Newly registered and marketed fungicides include: fenpicoxamid, aminopyrifen, dichlobentiazox, fluindazole, and ipflufenoquin.
.1 Fenpicoxamid
Fenpicoxamid is a new type of pyridine amide fungicide jointly developed by Dow AgroSciences (currently Corteva) and Meiji Seika, and its development codes are XDE-777, XR-777, X772777. Its CAS registration number is 517875-34-2, and its chemical structure is shown in Figure 10.
Figure 10 Structural formula of Fenpicoxamid
Fenpicoxamid has low toxicity, no carcinogenicity, mutagenicity, endocrine interference activity, neurotoxicity, reproductive and developmental toxicity. It acts on the Qi site of mitochondrial respiratory chain complex III ( cytochrome c reductase or bc1 complex), and blocks the electron transfer from cytochrome b to cytochrome c1, causing the organism to fail to synthesize ATP normally , and then die of exhaustion. The International Fungicide Resistance Action Committee (FRAC) classified fenpicoxamid into Group C4, and the other two members of this subgroup are cyazofamid and amisulbrom.
Fenpicoxamid has high bactericidal activity and long-lasting effect. It is mainly used in cereals, including winter wheat, spring wheat, durum wheat, rye and triticale, etc. It is also used in bananas and other crops. Fenpicoxamid has no cross-resistance with existing cereal fungicides such as methoxyacrylates, triazoles, and succinate dehydrogenase inhibitors, so it can be used as a resistance management tool. Fenpicoxamid is the first new type of pyridine amide fungicide for cereals. Field test results show that it is effective against almost all important diseases of cereals, such as leaf blight, , rust, etc., and has a long lasting effect.
Fenpicoxamid is derived from the natural compound UK-2A through fermentation. Dow AgroSciences has applied for a European patent (EP1438306) for the general formula compound including it, and submitted a PCT application. The international publication number is WO03035617A2, and the application date was October 2002. 23rd. The patent has been authorized by Australia, Canada, Europe, Japan, and the United States.
The European Union is the most widely planted region of cereals and the largest market for fungicides used in cereals. In 2018, fenpicoxamid was registered in the European Union, valid for 10 years. The registered product is 130 g/L suspension concentrate (trade name Inatreq), which is used for winter and spring wheat, durum wheat, rye, and triticale to prevent and control Septoria leaf blight. In March 2020, fenpicoxamid was registered in France and will be launched in the 2021 planting season under the trade name Questar. In 2019, Corteva 50 g/L fenpicoxamid EC (GF-3308) was registered in New Zealand for use in wheat to control leaf blight (Septoria tritici) and leaf rust (Puccinia tritici) caused by Septoria.
In addition to the cereal market, the development company is also actively promoting the registration of fenpicoxamid in other crops. In October 2017, the US EPA made a registration decision on fenpicoxamid (joint review with Canada), and fenpicoxamid products are used in wheat, rye, and bananas.In addition, the fenpicoxamid-based product Kyventiq has been registered in Belize, Colombia, Ecuador, Guatemala, Honduras, Ivory Coast and Panama for use on bananas to control black streak leaf spot (Mycosphaerella fijiensis).
.2 Aminopyrifen
Aminopyrifen is a pyridine fungicide developed by Japan Agro-kanesho Company, with the development code AKD-5195. Its CAS registration number is 1531626-08-0, and its structural formula is shown in Figure 11.
Figure 11 The chemical structure of Aminopyrifen
Aminopyrifen has a unique mechanism of action. It is an inhibitor of the fungal protein GWT-1 (GPI-anchored wall transfer protein 1) in the biosynthetic pathway of glycosylphosphatidylinositol (GPI). GPI is a protein and cell membrane The only way to combine.
Aminopyrifen has a wide bactericidal spectrum and is suitable for many crops. It can be used for rice, wheat, citrus, apple, pear, peach, grape, potato, tomato, tobacco, tea, rape, sugar beet, etc. to prevent and control rice blast, sheath blight, powdery mildew, Head blight, scab, anthracnose , ring spot, etc., have strong activity against a variety of pathogenic bacteria including Botrytis cinerea . In addition, the fungicide has no cross-resistance with existing fungicides such as benzimidazoles, dicarboximides, pyrimidine amines, DMIs, QoIs, and SDHIs. Agro-kanesho company research found that aminopyrifen is active against a variety of pathogenic bacteria, and at very low concentrations, it can inhibit the growth of mycelia.
Japan Agro-kanesho applied for a European patent (EP2871180) for general formula compounds including aminopyrifen compounds, and submitted a PCT application with the International Publication No. WO2014006945 on April 2, 2013. The patent has also applied for compound patent protection in China, Australia, Brazil, Canada, Europe, Japan, South Korea, the United States and other countries and regions.
Aminopyrifen has a high control effect on powdery mildew and gray mold of various fruit and vegetable crops, and is expected to be launched in 2021.
.3 Dichlobentiazox
Dichlobentiazox is a benzothiazole fungicide developed by Japan Combination Chemical Industry Co., Ltd., with the development code KIF-1629. Its CAS registration number is 957144-77-3, and its structural formula is shown in Figure 12.
Figure 12 Structural formula of Dichlobentiazox
Dichlobentiazox has low toxicity to rats, and the residue in the environment is its parent compound, which has no carcinogenicity, reproductive toxicity, teratogenicity and genotoxicity.
Dichlobentiazox is a brand-new fungicide discovered by Japan Combination Chemicals in the process of developing saccharin derivatives, containing benzisothiazole and isothiazole groups. FRAC has not yet classified its mechanism of action, but the development company speculates that it may be a plant defense activator.
Dichlobentiazox has a broad spectrum of prevention and treatment and a long duration of effect. Under different environmental conditions and treatment methods, dichlobentiazox has a stable control effect on rice blast, etc., and has high safety. It has no inhibitory effect on the growth of rice seedlings, and does not delay seed germination. In addition to rice, dichlobentiazox can also control cucumber downy mildew, anthracnose, powdery mildew, gray mold, bacterial spot, wheat powdery mildew, glume blight, leaf rust, rice blast, sheath blight, bacterial blight disease, bacterial grain blight, bacterial blight, brown spot, brown stain, apple scab and other diseases are highly effective.
Combination Chemical Industry Co., Ltd. and Anhara Chemical Industry Co., Ltd. applied for European patent (EP2017268) for general formula compounds including dichlobentiazox compound, and submitted PCT application, international publication number WO2007129454, patent application date on April 20, 2007. The patent has been authorized by China, Europe, Japan, South Korea, and the United States.
Combinatorial Chemistry has submitted the registration application materials for dichlobentiazox. The registered crop is rice, which is expected to be registered and launched this year.
.4 Fluindapyr (fluindapyr)
Fluindapyr is a new type of pyrazole amide fungicide, its English common name is fluindapyr, and its development code is IR9792 and F9990. Its CAS registration number is 1383809-87-7, and its structural formula is shown in Figure 13.
Figure 13 Structural formula of flundafyram
Fluindazole is a succinate dehydrogenase inhibitor (SDHI) fungicide, which acts on complex II in the mitochondrial respiratory electron transport chain of pathogenic bacteria, and interferes with the mitochondria of pathogenic bacteria cells Respiration, which in turn leads to the failure and death of organisms.
Fluindazole is a broad-spectrum, systemic fungicide with protective, therapeutic and eradicating activities. It is suitable for many crops, such as grains, soybeans, rice, nut trees, rape, corn, cotton, fruits and vegetables, lawns and ornamental plants, etc., and the control includes Septoria (Septoriaspp.), Alternaria (Alternariaspp.) diseases, soybean Asian rust, leaf blight, sheath blight, rice blast, flower blight, sclerotinia, anthracnose, gray mold and powdery mildew. While fluindaclostrobin can effectively control diseases, it can also increase crop yields. The results of the efficacy test in field plots carried out by FMC Corporation in my country show that: when the active ingredient dosage of 42% fluindazole SC is 100-120 g/hm2, it can be sprayed before the onset of the disease or at the initial stage of the disease, and sprayed 3 times with an interval of 3 times. After about 7 days, the control effect on cucumber powdery mildew was 80%-90%, and the control effect on tomato gray mold was 75%-85%.
Yisaig applied for the European patent (EP2655333) for compounds of the general formula including fluindazole, and submitted a PCT application with the international publication number WO2012084812A1 on December 19, 2011. The patent has been authorized by China, Argentina, Australia, Brazil, Canada, Italy, Japan, South Korea, and the United States.
Fluindaclostrobin was first discovered by Isagro of Italy, and jointly developed by Isagro and FMC Corporation of the United States. In 2020, FMC acquired the global assets of Yisaig, including intellectual property rights, patented technologies, registrations, and preparations of fluindaclostrobin.
In December 2019, Yisaig's fluindaclostrom-based EC product Zaltus (100 g/L fluindaclostrobin + 100 g/L tetrafluconazole) was first launched in Paraguay for the control of soybean Asian rust. In December 2020, the registration of flundafyram in the United States was announced. The registered product is a suspension agent, which is used for soybeans, grains (except rice), grain feed, forage, nut trees, etc., and non-agricultural fields, including golf courses , lawns, ornamental plants, flowers, etc. In 2021, Onsuva, a new fungicide of FMC's flundafyram product (a compound preparation of flundafyram and difenoconazole), will be launched in Argentina for soybeans and peanuts.
Fluindazone has applied for registration in China and the European Union, and is expected to be launched in China in 2022.
.5 Ipflufenoquin
Ipflufenoquin is a quinoline fungicide developed by Nippon-Soda, codenamed NF-180. Its CAS registration number is 1314008-27-9, and its structural formula is shown in Figure 14.
Figure 14 Ipflufenoquin structural formula
Ipflufenoquin is highly safe and poses no health threat to humans, and has no worrisome risks to the non-target organisms tested, including birds, bees, and terrestrial plants.
Ipflufenoquin has a novel mechanism of action that has not yet been classified by FRAC. Ipflufenoquin has a wide bactericidal spectrum and can be used for rice, barley, wheat, tomato, potato, apple, grape, tobacco, etc. to prevent and control scab, leaf spot, gray spot, anthracnose, sclerotinia, powdery mildew, downy mildew , late blight, etc. It is also used for resistance management, which can effectively prevent and control pathogenic bacteria that are resistant to existing agents, including Venturia (Venturiaspp.), Botrytis (Botrytisspp.) and Sclerotinia (Sclerotiniaspp.), etc.
In 2017, the Agriculture Bureau of Yongshun County, Hunan Province carried out field experiments to verify the control effect of ipflufenoquin products on rice blast and rice leaf diseases in the late growth stage. Heading of rice plants) Spray and apply 2 times. The results show that ipflufenoquin is highly effective against rice blast, and can also treat rice false smut and other leaf diseases; under the test dosage, it is safe for rice growth, with strong leaves and no dead phenomenon.
Nippon Soda Co., Ltd. applied for European patent (EP2522658) for general formula compounds including ipflufenoquin compound, and submitted PCT application, international publication number WO2011081174, and the application date was December 28, 2010. The patent has been authorized by many countries and regions such as China, Australia, Brazil, Canada, Europe, Japan, South Korea, and the United States.
Nippon Soda submitted 3 registration applications based on ipflufenoquin in Japan, with active ingredient contents of 20%, 10% and 8% respectively. The crops to be registered include various fruits, vegetables and rice.In 2021, ipflufenoquin-based products will be registered in the United States for the control of pome head blight, powdery mildew, apricot brown rot, scab, anthracnose, leaf spot, etc.
Nematicides
Newly registered and marketed nematicides include cyclobutrifluram and triflumid.
.1 Cyclobutrifluram
Cyclobutrifluram is a new type of nicotinamide fluorine-containing fungicide and nematicide developed by Syngenta, including (1S,2S)-enantiomer and (1R,2R)-enantiomer, the former accounting for 80% to 100% %, the latter accounts for 0-20%. Its CAS registration number is 1460292-16-3, and its structural formula is shown in Figure 15.
Figure 15 Cyclobutriflura structural formula
Cyclobutrifluram structure is similar to fluopyram (fluopyram), and the development company speculates that it is an inhibitor of mitochondrial electron transport chain complex II. Cyclobutrifluram paralyzes nematode larvae by interfering with respiration, which leads to depletion of energy in the cells, and it inhibits egg hatching.
Cyclobutrifluram has a broad control spectrum and can be used to control nematodes and major fungal diseases caused by nematodes. Its control effect is good, and it can effectively control root-knot nematodes, cyst nematodes, short-body nematodes, gall nematodes, grain nematodes, slippery nematodes, pine nematodes, ring nematodes, and stem nematodes in cucumber, tomato, corn, soybean, sugar beet and other crops. , Spiral nematodes, etc. Cyclobutrifluram is simple and convenient to use, and can be applied directly or treated with seeds, and the dosage is small.
Syngenta Joint Stock Co., Ltd. applied for European patent (EP2644595) for general formula compounds including cyclobutrifluram compounds, and submitted a PCT application, International Publication No. WO2013143811, the application date was March 6, 2013. The patent has been authorized by many countries and regions such as China, Australia, Brazil, Canada, Japan, South Korea, and the United States.
In May 2020, Syngenta announced the launch of TYMIRIUM™, a new fungicidal nematicide based on cyclobutrifluram, for use in seeds and soil. TYMIRIUM™ can provide long-term control of various nematode and soil-borne diseases in all major crops and various terrains, especially has excellent control effect on diseases caused by Fusarium. Syngenta plans to launch the first products with TYMIRIUM™ technology in Latin America in 2021/2022.
.2 Fluazaindolizine (fluazaindolizine)
Fluazaindolizine is a new type of sulfonamide nematocide developed by DuPont (now Corteva), its English common name is fluazaindolizine, and its development code is DPX-Q8U80. Its CAS registration number is 1254304-22-7, and its structural formula is shown in Figure 16.
Figure 16. Structural formula of triflumidazolamide
Triflumidazolamide is a non-fumigation nematicide, which has a different target site from existing nematocides, so it is speculated that it has a new mechanism of action. Triflumid is safe for users, friendly to the environment, harmless to beneficial arthropods, pollinators and soil organisms, can better help farmers manage soil and crops, and is an ideal product in the integrated pest management system (IPM) . Triflumid is highly compatible with naturally occurring or introduced biocontrol agents that help keep crops and soil healthy, such as beneficial fungi and bacteria, nematodes, and other important non-target organisms.
Triflumid is suitable for many crops and has a wide control spectrum. It can be used on fruit and melon vegetables, root vegetables (carrots, sweet potatoes, potatoes), soybeans, sugar cane, coffee, cereals, canola, nut trees, stone fruits and grapes; against tobacco root-knot nematode, soybean cyst nematode, strawberries Various kinds of nematodes, such as smooth edge nematode, potato stem nematode, pine wood nematode, grain nematode and short body (root rot) nematode. Its application method is flexible, and drip irrigation, spraying, and soil application are all available. The dosage varies according to the application method. Usually, the dosage of active ingredients is 0.25-2 kg/hm2. The
development company has conducted extensive laboratory, greenhouse and field trials on triflumid in North America, Latin America, Europe and Asia Pacific.The test results prove that triflumidazide can well control the damage of plant parasitic nematodes. It is effective against a variety of root-knot nematodes (Meloidogynespp.), other important plant parasitic nematodes, such as reniform nematodes (Rotylenchulus reniformis), sword nematodes (Xiphinemaspp. .), Spiral nematode (Helicoty lenchusspp.), and other nematode species, such as short-bodied nematodes (Pratylenchus spp.), etc. At the same time, the test also confirmed that triflumid reduced the damage caused by parasitic nematodes to the root system of plants, and improved the quality and yield of crops.
DuPont applied for a European patent (EP2427058) for compounds of the general formula including trifluridine, and submitted a PCT application with the international publication number WO2010129500 on May 4, 2010. The patent has been authorized by many countries and regions such as China, Australia, Canada, Europe, Japan, South Korea, and the United States.
In 2021, triflumid will be registered in Canada, the United States, and Australia. The trade name of the registered product in Canada is Salibro, which is used to control plant parasitic nematodes, such as root-knot nematodes in tubers, bulbs, cucurbit vegetables, fruits and vegetables, and carrots. U.S. registered products for use include carrots and cucurbit vegetables, certain fruit, tuber and bulb vegetables, and certain crops that do not bear fruit within one year after application of other nematicides, such as citrus fruits, stone fruits, nuts and small climbing plants. Vine fruit (except kiwi downy). The product registered in Australia under the trade name Salibro Reklemel is used to control root-knot nematodes in cucurbits, melon and tuber vegetables.
In November 2020, Shenlibao ®, a nematicide product of Corteva triflumid (Ruigenmei ®), was unveiled at the China Plant Protection Bi-Fair. Shenlibao ® is efficient, safe, less frequently used, and has high selectivity. It can provide lasting protection for the root system and is an effective tool for comprehensive soil management.
Author: Jiangsu Pesticide Association Pesticide Information Network Gu Linling
