Cypyrafluone (Huanbifucaotong): New HPPD Inhibitor Herbicide from KingAgroot, China

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 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.)

BY Companies including :

1. Qingdao Kingagroot Chemical Compound Co., Ltd. (28)
2. Bayer A.-G. (5)
3. Jiangsu Qingyuan Nongguan Weed Control Co., Ltd. (2)
4. Nanjing Agricultural University (1)
5. Nanjing Gaozheng Agricultural Chemical Co., Ltd. (1)
6. Nanjing Zhengrong Pharmaceutical Chemical Co., Ltd. (1)
7. Qingdao Qingyuan Resistant Weeds Control Co., Ltd. (1)
8. Shandong Agricultural University (1)
9. Taian Institute of Agricultural Sciences (1)

Basic Details of Cypyrafluone (Huanbifucaotong):

CAS RN. 1855929-45-1

IUPAC: 1-​[2-​Chloro-​3-​[(3-​cyclopropyl-​5-​hydroxy-​1-​methyl-​1H-​pyrazol-​4-​yl)​carbonyl]​-​6-​(trifluoromethyl)​phenyl]​-​2-​piperidinone

Class / Activity: Herbicides (benzoylpyrazole herbicides)

Innovator: KingAgroot’s

QINGDAO KINGAGROOT CHEMICAL COMPOUND CO., LTD filed fifteen polymorph international patent applications on “Cypyrafluone”.

Access Patents:

1. WO2020133013 - CRYSTALLINE FORM B OF CYPYRAFLUONE ISOPROPYLAMINE SALT, AND PREPARATION METHOD AND USE THEREFOR https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133013&_cid=P10-KCHO2Y-15250-1

2. WO2020133019 - CRYSTALLINE FORM B OF CYPYRAFLUONE DIMETHYLAMINE SALT, AND PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133019&_cid=P10-KCHO2Y-15250-1

3. WO2020133020 - CYPYRAFLUONE DIMETHYLAMINE SALT C CRYSTAL FORM, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133020&_cid=P10-KCHO2Y-15250-1

4. WO2020133017 - CYPYRAFLUONE MONOISOPROPYLAMINE SALT CRYSTALLINE FORM F AND PREPARATION METHOD AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133017&_cid=P10-KCHO2Y-15250-1

5. WO2020133015 - CYPYRAFLUONE MONOISOPROPYLAMINE SALT D CRYSTAL FORM, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133015&_cid=P10-KCHO2Y-15250-1

6. WO2020133016 - CYPYRAFLUONE MONOISOPROPYLAMINE SALT E CRYSTAL FORM, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133016&_cid=P10-KCHODJ-17252-2

7. WO2020133024 - CYPYRAFLUONE TRIETHANOLAMINE SALT, PREPARATION METHOD THEREFOR, AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133024&_cid=P10-KCHODJ-17252-2

8. WO2020133022 - CYPYRAFLUONE DIMETHYLAMINE SALT, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133022&_cid=P10-KCHODJ-17252-2

9. WO2020133021 - CYPYRAFLUONE DIMETHYLAMINE SALT D CRYSTAL FORM, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133021&_cid=P10-KCHO2Y-15250-1

10. WO2020133014 - CRYSTALLINE FORM C OF CYPYRAFLUONE MONOISOPROPYLAMINE SALT, AND PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133014&_cid=P10-KCHODJ-17252-2

11. WO2020133025 - CYPYRAFLUONE TRIETHANOLAMINE SALT B CRYSTAL FORM, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133025&_cid=P10-KCHO2Y-15250-1

12. WO2020133012 - CYPYRAFLUONE MONOISOPROPYLAMINE SALT AND PREPARATION METHOD AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133012&_cid=P10-KCHODJ-17252-2

13. WO2020133018 - AMORPHOUS CICLOPIROX FLURIDONE DIMETHYLAMINE SALT, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133018&_cid=P10-KCHO2Y-15250-1

14. WO2020133023 - AMORPHOUS CYPYRAFLUONE TRIETHANOLAMINE SALT, PREPARATION METHOD THEREFOR AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133023&_cid=P10-KCHO2Y-15250-1

15. WO2020133011 - AMORPHOUS CYPYRAFLUONE MONOISOPROPYLAMINE SALT AND PREPARATION METHOD AND USE THEREOF https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020133011&_cid=P10-KCHO2Y-15250-1

Basic Product Patent Information:

Patent Number: WO2017075910A1 Est. Expiry: Jan 08, 2036

Assignee: Qingdao Kingagroot Chemical Compounds Co., Ltd., China

Priority: Nov 06, 2015

Publication Date: 2017-05-11

Application Number: WO2016-CN70453

Application Date: 2016-01-08

Equivalent: AU2016350960A1; AU2016350960B2; BR112018007527A2; CA2979570A1; CN105218449A; CN105218449B; WO2017075910A1; CN107311980A; CN107311980B; EP3287445A1; EP3287445A4; EP3287445B1; LT3287445T; RU2697417C1; US2018055054A1

Indian Patent Equivalent: IN 201717033107

Title: Pyrazole ketone compound or salt thereof, preparation method, herbicidal composition and application

Cypyrafluone has a systemic action and is an HPPD inhibitor herbicide for post-stem and leaf treatment of the wheat field. It has good biological activity and effectively prevents a variety of weeds in wheat fields.

On May 22, 2018, the patent “An herbicidal composition containing Cypyrafluone and Bipyrazone and its application” (CN105961401B; Applicant: Tai’an Acad Of Agricultural Sciences) was issued for publication.

Cypyrafluone was registered by Jiangsu KingAgrootWeed Management Co., Ltd. In China.

The field demonstration evaluation and acceptance of the patented compound Cypyrafluone, invented by KingAgroot for control of resistant Alopecurus japonicas, was held in Nanjing City and Anhui Province in China from 6 – 7 April 2019. A committee consisting of 13 well-known experts endorsed. The experts are of the opinion that this is the first HPPD inhibiting herbicide for control of grassy weed in wheat fields which does not cause cross-resistance to the currently mainstream wheat field-applied ALS inhibitors, such as mesosulfuron and pyroxsulam, as well as the ACCase inhibitors, such as clodinafop-propargyl, pinoxaden and fenoxaprop-p-ethyl. Experts hold that it is a new herbicidal for control of the most difficult weeds, such as Alopecurus japonicas, and that the research has been fully completed.

China Registrations info for Cypyrafluone:

• PD20184021: 95% Cypyrafluone technical;
• PD20184019: 6% Cypyrafluone dispersible oil suspension;
• PD20184020: 25% Cypyrafluone and isoproturon dispersible oil suspension (22% isoproturon + 3% cypyrafluone).

About KingAgroot:

Established in 2009 and headquartered in Qingdao. Qingdao is a city in China’s eastern Shandong province, is a port city of skyscrapers, parks, and beaches bordering the Yellow Sea. 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.

Research and development is the belief of everyone in KingAgroot. In terms of compound invention, KingAgroot’s innovation team has successfully developed 4 HPPD inhibitors: Cypyrafluone, Bipyrazone, Tripyrasulfone, Fenpyrazone. By the end of July 2019, KingAgroot has filed 108 national invention patents (including 32 authorized ones) and 84 PCT patents (including 4 authorized ones), accumulatively entering 79 countries (region)-time.

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