New ISO published after October 2020 – 9 new agrochemical candidates published including Benquitrione (Shandong Cynda Herbicide), Bipyrazone (Qingdao Qingyuan Herbicide), Cypyrafluone (Kingagroot Herbicide), Dioxopyritrione (Syngenta Herbicide), Fluoxytioconazole (Corteva Triazol Fungicides), Seboctylamine, Tripyrasulfone (Kingagroot Herbicide), Anisiflupurin (Syngenta Plant Growth Regulators (Cytokinins)) and Spidoxamat (Bayer Insecticides), please refer for more detail.
1. Benquitrione
Bipyrazone, 1,3-dimethyl-4-(2-(methylsulfonyl)-4-(trifluoromethyl) benzoyl)-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazole- 4-carboxylate, is a 4-hydroxyphenylpyaunate dioxygenase (HPPD)-inhibiting herbicide.
Bipyrazone has the potential for control of broadleaf weeds such as D. sophia, C. bursa-pastoris, L. arvense and M. aquaticum, whereas it has little or no efficacy against grassy weeds like some HPPD-inhibiting herbicides, such as mesotrione.
With bipyrazone registration, there is a new mode of action being commercially introduced for the first time in China. Thus, bipyrazone may be an excellent tool to control some broadleaf weeds that have evolved resistance to herbicides with different modes of action. However, careful attention should be paid to preventing or delaying the development of resistance by reducing herbicide selection pressure via alternating between POST and preemergence (PRE), mixing herbicides with different modes of action, and rotation. Also, increasing crop diversity and using biological control are practices to be encouraged.
A mixture of bipyrazone and fluroxypyr-mepthyl is studied for controlling broadleaf weeds and found satisfactory control of sensitive broadleaf weeds. These findings suggest that bipyrazone POST application has good potential for broadleaf weed management in wheat fields.
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-methyl-2,4(1H,3H)-quinazolinedione
- CAS RN..: 1639426-14-4
- ACTIVITY: Herbicides (Aroylcyclohexanedione Herbicides)
- Innovator: Discovered by Central China Normal University; Manufacturer is Shandong Cynda (Chemical) Co., Ltd. Development code Y13161.
- Mechanism of Action (MoA): Possibly Inhibitor Of 4-Hydroxyphenyl-Pyruvatedioxygenase (4-HPPD).
- Other Candidates from The Same Class: Dioxopyritrione; Fenquinotrione; Ketospiradox; Lancotrione; Mesotrione; Quintrione; Sulcotrione; Tefuryltrione and Tembotrione
IP Scenario:
1. WO2015058519A1 (Central China Normal University); Est. Exp. May 21, 2034.
Title: Preparation of triketone compounds for preventing and controlling weeds
Equivalents: CN104557739A; CN104557739B; WO2015058519A1; EP3061755A1; EP3061755B1; ES2687346T3; US20160264532A1; US9771334B2; IN201647014440A; IN312664B
Indian Equivalent: IN201647014440A; IN312664B
Abstract: Disclosed in the present invention is a triketone compound which has a structure of formula I, wherein Z is O or S; R1 is H, alkyl, halo, NO2, alkoxy or CN; R2 is (un)substituted Ph, benzyl, bicycloaryl or tricycloaryl; R3 is H, alkyl, (un)substituted Ph, or benzyl; R4-9 is H, alkyl, alkoxy or halo. Also disclosed in the present invention is a method for preparing the triketone compounds which comprises that under the rearrangement reaction conditions, the compound having a structure of formula II is contacted with a catalyst in the presence of a base and a solvent. Further disclosed in the present invention is the use of a triketone compounds in preventing and controlling weeds. The title compound has the effect of preventing and controlling weeds, in particular having an excellent effect on preventing and controlling broad-leaved weeds and/or gramineae weeds.
2. Bipyrazone
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 1,3-dimethyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate
- CAS RN..: 1622908-18-2
- ACTIVITY: Herbicides (benzoylpyrazole herbicides)
- Innovator: Qingdao Qingyuan Chemical Compound Co Ltd
- Mechanism of Action (MoA): Possibly Inhibitor Of 4-Hydroxyphenyl-Pyruvatedioxygenase (4-HPPD).
- Other Candidates from The Same Class: Benzofenap; Bipyrazone; Cypyrafluone; Fenpyrazone; Pyrasulfotole; Pyrazolynate; Pyrazoxyfen; Tolpyralate; Topramezone and Tripyrasulfone.
IP Scenario:
1. CN103980202A (Est. Exp. : 2034-05-27)
Title: A 4-benzoyl-pyrazole compound with weed control activity
Equivalents: CN103980202A; CN103980202B
Abstract: The invention disclosed a kind of 4-benzoyl-pyrazole compound with weed control activity. The claimed 4-benzoyl-pyrazole compound is shown in structure I (R1 = H, Me, Et; R2 = mesyl, methoxy, Me mercapto, fluoro, chloro or cyano; R3 = H, Me, fluoromethyl, difluoromethyl or trifluoromethyl; R = five-membered aromatic heterocyclic group, six-membered aromatic heterocyclic group, C1-C6 alkyloxy, aromatic hetero-oxy, six-membered aryloxy or six-membered arylamino; m,n = 0 or 1 but not equal one at same time). The claimed comod. is prepared via multiple steps (procedure given). The obtained compound has herbicide and plant growth regulator activities with better selectivity and safety.
3. Cypyrafluone
KingAgroot is a scientific innovation company that dedicates to improving the efficiency and quality of world agriculture production from two aspects, herbicide new compound development, and gene-editing breeding, hoping to make our own contribution to the security of the world food supply.
KingAgroot established in 2009 and headquartered in Qingdao, KingAgroot is a scientific innovation company that dedicates to improving efficiency and quality of world agriculture production from two aspects, herbicide new compound development, and gene-editing breeding, hoping to make our own contribution to the security of world food supply.
Standing on China and embracing the world, KingAgroot is working on providing the most complete solutions from new compounds to gene-editing breeding to resistant weed problems in widely planted crops in the world, such as rice, wheat, corn, soybean, peanut, orchard, vegetable, etc.
KINGAGROOT China got fifteen polymorph international patent applications on “Cypyrafluone” on July 02, 2020.
Cypyrafluone (Huanbifucaotong) is an HPPD inhibiting herbicidal compound, which was granted full registration by the Chinese Ministry of Agriculture and Rural Affairs on the 30th of August 2018. The product, which is based on the ingredient of Cypyrafluon, was successfully launched in the market at the end of 2018.
The application has covered more than 1 million Mu of cropland in its first year of release and has been well recognized by farmers. It is expected that the application will reach a coverage of 40 – 50 million Mu in the year ahead, with global sales reaching $500 – $700 million.
Total Patents for Cypyrafluone: 39 Patent Families filed (composition / combination / Method of Use etc.).
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 1-[2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl]-2-piperidinone
- CAS RN..: 1855929-45-1
- ACTIVITY: herbicides (benzoylpyrazole herbicides)
- Innovator: KingAgroot
- Mechanism of Action (MoA): Inhibitor Of 4-Hydroxyphenyl-Pyruvatedioxygenase (4-HPPD).
- Other Candidates from The Same Class:
IP Scenario:
1. WO2017075910A1 (Est. Exp.: Jan 08, 2036)
Title: Pyrazole ketone compound or salt thereof, preparation method, herbicidal composition and application
Equivalents: AU2016350960A1; AU2016350960B2; BR112018007527A2; CA2979570A1; CN105218449A; CN105218449B; WO2017075910A1; CN107311980A; CN107311980B; EP3287445A1; EP3287445A4; EP3287445B1; LT3287445T; RU2697417C1; US2018055054A1
Indian Patent Equivalent: IN 201717033107
Abstract: The inventive pyrazole ketone compound has structure shown as general formula I, wherein R1R2N represents (un)substituted 3-8 membered nitrogen-containing heterocyclic group containing 1-3 hetero atoms, or R1 and R2 are independently H, alkyl, heteroalkyl, etc.; R3 is H, alkyl, alkenyl, alkynyl, cycloalkyl or alkyl substituted cycloalkyl; R4 is Me, Et, Pr, iso-Pr, or cyclopropyl; X is H, S(O)nR6, R7, or (substituted) 3-8 membered heterocyclic group containing 1-4 hetero atoms, n is 1, 2 or 3; R6 is (un)substituted alkyl or aryl, R7 is (un)substituted alkyl, aryl, alkanoyl or aroyl. Compounds of the invention were prepared and evaluated for their herbicidal activity on various crops (data given). The pyrazole ketone compound has good herbicidal effect, convenient application, low cost, and high com. value.
QINGDAO KINGAGROOT CHEMICAL COMPOUND CO., LTD filed fifteen polymorph international patent applications on “Cypyrafluone”.
For details: please refer to this article
4. Dioxopyritrione
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3(2H)-one
- CAS RN..: 2222257-79-4
- ACTIVITY: herbicides (aroylcyclohexanedione herbicides; pyridazinone herbicides)
- Innovator: The manufacturer is Syngenta Crop Protection AG.
- Mechanism of Action (MoA): Possibly Inhibitor Of 4-Hydroxyphenyl-Pyruvatedioxygenase (4-HPPD).
Other Candidates from The Same Class:
- Other aroylcyclohexanedione herbicides: Dioxopyritrione; Fenquinotrione; Ketospiradox; Lancotrione; Mesotrione; Quintrione; Sulcotrione, Tefuryltrione and Tembotrione.
- Other Pyridazinone herbicides: Brompyrazon, Chloridazon, Dimidazon, Dioxopyritrione, Flufenpyr, Metflurazon, Norflurazon, Oxapyrazon, Pydanon.
IP Scenario:
Dioxopyritrione has assigned CAS Registry number 2222257-79-4. The said registry is not disclosed with any published document, yet. It’s possible, it is covered in the patent as a generic Markush structure.
5. Fluoxytioconazole
Fluoxytioconazole is discovered by Corteva Agriscience. Its development codes are X12499481, XR-481 and XDE-481. The CAS name and Registry Number are for the tautomer that is preferred under the CAS nomenclature rules.
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 4-[[6-[2-(2,4-difluorophenyl)-3-(2,5-dihydro-5-thioxo-1H-1,2,4-triazol-1-yl)-1,1-difluoro-2-hydroxypropyl]-3-pyridinyl]oxy]benzonitrile
- CAS RN..: 2046300-61-0
- ACTIVITY: fungicides (conazole fungicides)
- Innovator: Corteva Agriscience
- Mechanism of Action (MoA): Possibly Inhibition of ergosterol biosynthesis, by inhibition of C14-demethylase (SBI Class I)
- Other Candidates from The Same Class: Azaconazole; Bromuconazole; Cyproconazole; Diclobutrazol; Difenoconazole; Diniconazole; Diniconazole-M; Epoxiconazole; Etaconazole; Fenbuconazole; Fluoxytioconazole; Fluquinconazole; Flusilazole; Flutriafol; Furconazole; Furconazole-Cis; Hexaconazole; Imibenconazole; Ipconazole; Ipfentrifluconazole; Mefentrifluconazole; Metconazole; Myclobutanil; Penconazole; Propiconazole; Prothioconazole; Quinconazole; Simeconazole; Tebuconazole; Tetraconazole; Triadimefon; Triadimenol; Triticonazole; Uniconazole and Uniconazole-P.
IP Scenario:
1. WO2016187201A2 (Est.Exp.: 2036-05-17)
Title: Preparation of pyridinyloxybenzonitrile compounds as metalloenzyme inhibitors useful as antifungal agents
Equivalents: AR104695A1; AU2016265932A1; BR112017024463A2; CA2986041A1; CL2017002929A1; CN107750248A; CO2017012621A2; CR20170574A; EA201792519A1; EP3297998A2; EP3297998A4; EP3297998B1; IN201747045203A; JP2018522821A; KR20180000731A; MX2017014848A; PH12017502082A1; TW201706260A; TWI623527B; WO2016187201A2; WO2016187201A3; US2019216087A1; ZA201707783B
Indian Equivalents: IN201747045203A
Abstract: The invention relates to compounds of formula I [wherein R1 is II or III] or an acceptable salt, solvate, prodrug, or hydrate thereof are claimed and exemplified. E.g., IV was prepared to start from 6-bromopyridin-3-ol and 4-fluorobenzonitrile in five steps. IV was evaluated for activity against leaf blotch of wheat and physicochem. properties. The compounds of formula I are inhibitors of metalloenzymes, such as lanosterol demethylase (CYP51). demethylase (CYP51)
6. Seboctylamine
The name “xinjunan” (辛菌胺) is approved in China. Seboctylamine is known since 1952, there are more than 59 patent applications filed since 1952. New combination of Seboctylamine product with Kasugamycin 2% + (Seboctylamine) Xinjunan acetate 1.2% SL Tomato Leaf mold.
When Seboctylamine is commercialized in the salt form, such as seboctylamine acetate [93839-40-8], Seboctylamine hydrochloride.
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: N1-octyl-N2-[2-(octylamino)ethyl]ethylenediamine
- CAS RN.: 57413-95-3
- ACTIVITY: Bactericides, Fungicides, (aliphatic nitrogen fungicides) Virucides
- Commercialization: The name “xinjunan” (辛菌胺) is approved in China.
- When this substance is used as a salt, its identity should be stated, for example seboctylamine acetate [93839-40-8], seboctylamine hydrochloride.
IP Scenario:
Seboctylamine is known since 1952, there are more than 59 patent applications filed since 1952.
IP Scenario:
1. DE845941 (Est.Exp.: 1968-12-14)
Title: Amino acids having bactericidal properties
Equivalents: DE845941
Abstract: Higher-mol. weight aliphatic monohalides treated with less than 2 moles of a polyalkylenepolyamine (I) having 2 primary NH2 radicals in terminal linkage, the mixture fractionally distilled to remove I HCl salt formed as by-product, and the resulting α,ω-dialkylpolyalkylene-polyamine condensed with a halo carboxylic acid produces the corresponding amino carboxylic acid which may be converted to a water-soluble salt of an organic or inorganic acid. Octyl chloride (110 g.) added within 4 hrs. to 116 g. NH(CH2CH2NH2)2 (II) at the boiling temperature, the crystalline II HCl salt precipitated as by-product removed, and the liquid product fractionated in vacuo gives 72 g. NH(CH2CH2NHC8H17)2 (III), b20 200-50°, as main fraction. Heating III 35 g. with 100 cc. N aqueous ClCH2CO2H solution 45 min. on the boiling water bath gives an aqueous solution of (C8H17NHCH2CH2)2NCH2CO2H HCl salt of excellent bactericidal properties. A similar product is obtained by replacing II by triethylenetetramine.
7. Tripyrasulfone
KingAgroot to launch Tripyrasulfone products in China upon completion of registration review.
On December 2, 2019, the Ministry of Agriculture and Rural Affairs of the People’s Republic of China announced a list of pesticide products to be approved for registration, comprising 17 products based on six new active ingredients, four of which are firstly registered in China. This also includes six pesticide products containing two new active ingredients, Tripyrasulfone, which is independently developed by KingAgroot, a Chinese agrochemical company.
Tripyrasulfone is a brand-new patented compound that is also the world’s first HPPD inhibitor herbicide that can be safely applied to the post-emergent stem and leaf treatment of paddy fields to control grassy weeds. It can effectively control barnyard grass resistant to ALS inhibitors and ACCase inhibitors and leptochloa resistant to ACCase inhibitors in paddy fields, and can significantly improve the global rice yield.
With the launch of paddy field herbicides, “Daoyu®”, “Daoguying®” and “Jingjie®”, with Tripyrasulfone as the active ingredient in the spring of 2020, they will function to clear obstacles and guarantee rice planting in China maintains a high and stable yield.
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1,3-dimethyl-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate
- CAS RN.: 1911613-97-2
- ACTIVITY: Herbicides (Benzoylpyrazole Herbicides)
- Innovator: KingAgroot
- Mechanism of Action (MOA): Inhibitor Of 4-Hydroxyphenyl-Pyruvatedioxygenase (4-HPPD).
IP Scenario:
1. CN105503728B (WO2017113509A1); Est.Exp.: 2035-12-31
Title: Preparation of pyrazole derivatives as herbicides
Equivalents: AU2016382562A1; AU2016382562B2; BR112018012921A2; CA2980382A1; CA2980382C; CN105503728A; CN105503728B; WO2017113509A1; CO2018005848A2; EP3398938A1; EP3398938A4; JP2019509251A; KR20180098258A; PH12017501912A1; RU2688936C1; US2018105513A1; US10556888B2
Abstract: The present invention belongs to the tech. field of pesticide, and particularly relates to a series of pyrazole compounds or salts thereof and preparation method, herbicide composition and application thereof. The pyrazole compound or its salt thereof has the structure as shown in formula I [wherein R1 is hydrogen atom or C1-C4 alkyl; R2 is C1-C3 alkyl; R3 is C1-C6 linear chain or cyclic group containing one or more heteroatom of O, S and N; R4 is C1-C3 alkyl or halogen; R5 is pyrazol ring or pyrazol ring replaced by one or more alkyl, alkoxy, halogen, haloalkyl, amidogen and nitryl]. For example, compound II was prepared in a multi-step synthesis. The pyrazole compound is a good herbicide, and has broad spectrum of biol. activity and outstanding crop safety.
8. Anisiflupurin
New ISO Published – Anisiflupurin-New Candidate by Syngenta Crop Protection AG.
Anisiflupurin is a 6-anilinopurine derivative, which inhibits cytokinin oxidase/dehydrogenase and possesses plant growth regulators activity. Anisiflupurin has a selectivity efficiency index in the inhibition of cytokinin oxidase/dehydrogenase, i.e., that are less toxic yet more efficacious than the other known analogs.
BASIC PRODUCT INFORMATION:
- STATUS: ISO 1750 (provisionally approved)
- IUPAC NAME: 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine
- CAS RN..: 1089014-47-0
- ACTIVITY: Plant Growth Regulators (Cytokinins)
- Innovator: Syngenta
- Mechanism of Action (MoA): Cytokinin oxidase/Dehydrogenase
IP Scenario:
1. WO2009003428A1 (Dolezal Karel ; Frebortova Jitka ; Galuszka Petr ; Gemrotova Marketa ; Schmulling Thomas [De]; Spichal Lukas ; Strnad Miroslav ; Univ Berlin Freie ; Univerzita Palackeho V Olomouc ; Werner Tomas; Zatloukal Marek; Est. Exp. July 02, 2028.
Title: Substituted 6-Anilinopurine Derivatives As Inhibitors of Cytokinin Oxidase/Dehydrogenase and Preparations Containing These Derivatives.
Equivalents: AU2008271800A1; AU2008271800B2; BRPI0812865A2; BRPI0812865B1; CA2691625A1; CA2691625C; CZ2007453A3; CZ302225B6; DK2173173T3; EP2173173A2; EP2173173B1; ES2431926T3; JP2010531818A; JP5539866B2; NZ582642A; PL2173173T3; PT2173173E; US2010190806A1; US8222260B2; WO2009003428A2; WO2009003428A3.
Abstract
The invention relates to substituted 6-anilinopurine derivatives of the general formula I, wherein R denotes one to five substituents independently selected from the group consisting of hydrogen, halogen, hydroxyl, amino, alkyloxy and alkyl group, and R2 denotes amino, halogen, nitro, thio, alkylthio or alkyl group for use as inhibitors of cytokinin oxidase/dehydrogenase. The invention also relates to the compositions containing these derivatives.
9. Spidoxamat (Plenexos)
New ISO Published – Spidoxamat (Trade Name: Plenexos): The Next Generation Ketoenol Insecticide.
First Launches Expected in 2024; > €300m Peak Sales Potential. Spidoxamat is the first keto-enol insecticide expected to offer both foliar and soil uses.
Basic Information of Spidoxamat :
- CAS RN.: 907187-07-9
- ACTIVITY: Insecticides (Tetramic acid insecticides)
- Mechanism of Action (MOA): Inhibitors of acetyl CoA carboxylase
- Innovators: Bayer AG
- Other Tetramic Acid Insecticides: Spidoxamat, Spiropidion, Spirotetramat.
Plenexos will enhance keto-enol insecticides by offering:
- High plant mobility, which ensures high efficacy against key sucking pests (aphids, white flies) at low dose rates for foliar and soil uses.
- Will feature a broad crop scope, as the ketoenol Spidoxamat2 is suitable for application in arable and horticulture crops (soybeans, cotton, fruits and vegetables)
- Regulatory submissions in key markets planned in 2022, approvals expected starting in 2024
- Targeted markets: LATAM, NA, APAC and TAMECIS
IP Scenario:
Compound / Product Patent Details:
1. DE102005008021(BAYER CROPSCIENCE AG); Est. Exp. Feb 08, 2026;
Title: Spiroketal-substituted cyclic ketoenols.
Equivalents:
AR053815A1; AU2006218154A1; AU2006218154B2; BRPI0607807A2; BRPI0607807B1; CA2597777A1; CA2597777C; CN101160049A; CN101160049B; CN101863873A; CN101885700A; CN101885719A; CN103755716A; DE102005008021A1; DK1855529T3; EA012785B1; EA200701772A1; EP1855529A2; EP1855529B1; ES2446240T3; IL185253A; JP2008531486A; JP5095419B2; KR101351261B1; KR20070106554A; MA29324B1; MX2007010111A; MY163974A; TW200640367A; TW201336415A; TWI389640B; TWI475955B; UA88949C2; US2008305955A1; US2011190493A1; US7897543B2; WO2006089633A2; WO2006089633A3; ZA200706980B.
Abstract:
The invention relates to novel spiroketal-substituted cyclic ketones of the formula (I) in which A, B, Q1, Q2, D, G, W, X, Y, and Z are as defined above, to processes and intermediates for their preparation and to their use as pesticides and/or microbicides and/or herbicides. Moreover, the invention relates to selective herbicidal compositions comprising, firstly, spiroketal-substituted cyclic ketoenols and, secondly, a crop plant compatibility-improving compound.
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