AU2024201111B2

AU2024201111B2 - Preparation method of high content saflufenacil

Info

Publication number: AU2024201111B2
Application number: AU2024201111A
Authority: AU
Inventors: Hui Ming Zhang; Yi Xiang Zhang
Original assignee: Leadfarm Australia Pty Ltd
Current assignee: Leadfarm Australia Pty Ltd
Priority date: 2021-08-25
Filing date: 2024-02-21
Publication date: 2025-04-17
Anticipated expiration: 2041-08-25
Also published as: AU2021221601A1; AU2024201111A1

Abstract

Preparation Method of High-content Saflufenacil Abstract The invention discloses a preparation method of herbicide high-content saflufenacil preparation, which comprises water dispersible granule and DF, and consists of saflufenacil API, one or more kinds of surfactants, a small amount of modifier and filler, wherein the saflufenacil content of the preparation is 75-9 2 wt%, and the preparation methods are rotary extrusion granulation method, boiling granulation method and spray granulation method.

Description

Preparation Method of High-content Saflufenacil

Cross-reference to related application This application is a divisional of Australian Patent Application No. 2021221601, the entire contents of which are incorporated herein by cross-reference.

Technical field The invention involves pesticide processing technology, in particular preparation technology of saflufenacil herbicide 75-92wt% high-content preparation, wherein the preparation is in a WDG (water dispersible granules) or DF (dry flowable) form, and the product can be used for weeding before and after seedlings of gramineous and broadleaf crops such as rice, rape and leguminous crops, and is mainly used for preventing and killing broadleaf weeds.

Technical background Saflufenacil is a uracil (or pyrimidine diketone) herbicide developed by BASF. Chemical name: N'-[2-chloro-4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4 trifluoromethyl pyrimidine-1-yl] benzoyl ]-N-isopropyl-N- methyl sulfonamide Chemical structural formula is:

F C4 F H 3C CH 3 F N 0 'N 'NN 03 '1Y F 0

CAS login number: 372137-35-4 The molecular formula is C17H17ClF4N405S The content of the API is over 95%, and it is white powder, melting point is 189-193.4°C.

Principle: saflufenacil is an inhibitor of protoporphyrinogen oxidase (PPO). By preventing the transformation of protoporphyrin iv to protoporphyrin iv in the process of chlorophyll biosynthesis, it destroys chlorophyll synthesis, causes chloroplast pigment whitening, tissue necrosis, and finally inhibits the growth until the plant dies.

Saflufenacil is mainly absorbed by roots and seedlings, with foliar contact and residual activities in soil, and can be bidirectionally transmitted in plants. It can conduct upward from xylem and downward from phloem, thus distributing throughout the plant.

Application field: saflufenacil can be used for more than 30 crops such as soybean, corn, grain, sugar cane, fruits and vegetables, rice, cotton, sorghum, etc. It can contain more than 90 broad-leaved weeds, such as abutilon, amaranthus retroflexus, ragweed, xanthium sibiricum, solanum nigrum, etc. It can be used as a pre-bud herbicide for corn and sorghum. Before planting, it is used for soybean, cotton, small grain and legume crops; post-bud treatment is used for fruit trees and nut crops; used as defoliant for cotton, sunflower and legume crops; as anon-selective herbicide, it is used in fallow land and non cultivated land. In addition, saflufenacil is also used to control weeds resistant to glyphosate, triazine herbicides and acetolactate synthase (ALS) inhibitors, such as chenopodium album, erigeronjaponicus, amaranthus longissima, ragweed, etc. The dosage of effective ingredients is 18 ~ 125 g/hm 2

. The appearance of pesticide in WDG and DF form is solid granules, in which the effective ingredients are 10-90wt%, and which can be evenly dispersed in water after being stirred in water. The finished product of granular pesticide preparation has stable performance, no dust, good fluidity, can save packaging materials and expenses, and is convenient for transportation and storage; the application method is flexible, and the product can be applied by spraying or mixing with soil; from the analysis of physical properties of dosage forms, WDG and DF are one of the most advantageous and competitive dosage forms of pesticide formulations, and have been rapidly developed and widely used all over the world.

The preparation of pesticide in WDG form is generally by a dry process, that is, the pesticides, auxiliaries and fillers are mixed, crushed by air flow or micronized into wettable powder with a particle size of 10-25tm, then added with water and kneaded into a wet material, then granulated (the granulation methods generally include disc granulation, extrusion granulation, high-speed shear granulation, fluidized bed granulation and dry powder compression granulation, etc.) and dried (the drying methods generally include fixed bed drying, boiling bed drying and fluidized bed drying, etc.).

The preparation of pesticide in DF form is generally by a wet sand grinding process, that is, grinding pesticide, auxiliary agent and filler into slurry with particle size of 5-15tm by sand mill or colloid mill, and then dehydrating by pressure spray granulation.

Due to poor physical properties, chemical stability and granulation of saflufenacil, its solid preparation content is generally between 1Owt% and 70wt%. For example, the Eragon product registered by BASF for controlling broadleaf weeds in non-cultivated land (stem and leaf spray) and citrus garden (directional stem and leaf spray) is 70wt% saflufenacil WDG, which is the highest preparation content reported in the market and publications at present. By screening and testing various surfactants and selecting and controlling the manufacturing process, the present inventor has been able to increase the content of the preparation to 92wt% on the premise of keeping the good drug effect of saflufenacil. Commercialization of this technology can greatly save the manufacturing cost and packaging materials, and facilitate transportation and storage.

Content of the invention The invention aims to provide a preparation method of high-content saflufenacil.

In order to solve the problems in the existing technology, the technical scheme provided by the invention is as follows: the surfactants enabling a content of 75-92wt% of saflufenacil can be screened out through tests on various surfactants, other chemical adjuvants can be added as modifiers according to the physical property requirements, such as defoamers, calcium and magnesium ion complexing agents, binders, etc., to improve the performance of the preparation, and inert materials (fillers) can be added for balancing if the balance is left.

Furthermore, preferable preparations of the invention comprises 75-92% of saflufenacil and 3.5-15.0% of surfactant by weight percentage.

The surfactant is one or more of polycarboxylate, lignosulfonate, alkyl naphthalene sulfonate, alkyl naphthalene sulfonate formaldehyde condensate salt, alkyl phenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, alkyl sulfate and alkyl sulfonate.

The filler is one or more of kaolin, light calcium carbonate, ammonium sulfate (potassium and sodium), diammonium hydrogen phosphate (potassium and sodium), ammonium chloride (potassium and sodium), ammonium nitrate (potassium and sodium), corn starch, white carbon black, sodium carbonate, sodium bicarbonate or sodium tripolyphosphate.

Summary According to a one aspect the invention provides a herbicidal saflufenacil preparation, comprising saflufenacil, one or more surfactants and wherein the content of saflufenacil is 75wt% or above.

According to another aspect the invention provides an herbicidal saflufenacil preparation, comprising saflufenacil as the sole active ingredient, one or more surfactants, wherein the content of saflufenacil is 75wt% or above, wherein the preparation is in a WDG (water dispersible granule) or a DF (dry flowable) form.

According to another aspect the invention provides a process for preparing an herbicidal saflufenacil preparation according the invention, the process comprising: mixing 75-92wt% saflufenacil and the one or more surfactants, and pulverizing the mixture, and granulating and drying the pulverised mixture.

According to another aspect the invention provides a method for preparing an herbicidal saflufenacil preparation according to the invention, the method comprising:

(i) mixing saflufenacil, a surfactant and a filler uniformly and pulverizing the mixture to 10-43 pm in a jet mill; (ii) adding 10- 2 5wt% water to the pulverized mixture and kneading to provide a wet powder; and (iii) extruding the wet powder into granules in a rotary granulator; and (iv) drying the granules at 50-100°C, and sieving to remove fine powder to provide an herbicidal saflufenacil preparation in WDG form.

(i) mixing saflufenacil, a surfactant and a filler uniformly and pulverizing the mixture to 10-43 pm in a jet mill; (ii) adding the resultant mixture to a boiling granulator or a disc granulator to provide a granulate; (iii) spraying 5-15wt% atomized water as a mist onto the granulate to provide wet granules; and (iv) drying the wet granules at 50-100°C, and sieving to remove fine powder to provide an herbicidal saflufenacil preparation in WDG form.

(i) mixing saflufenacil, a surfactant and, where required, a filler and water in a sand mill and grinding the resultant mixture to a particle size of 5-43pm; and (ii) spray granulating the ground mixture at 3.5MPa and 100-150°C, and sieving to remove fine powder to provide an herbicidal saflufenacil preparation in DF form.

Unless the context clearly requires otherwise, throughout the description and the claims, the words "comprise", "comprising", and the like are to be construed in an inclusive sense as opposed to an exclusive or exhaustive sense; that is to say, in the sense of "including, but not limited to".

Preferably, the content of saflufenacil is 75wt% - 9 2 wt%, and more preferably the composition comprises 75-92% by weight of saflufenacil and 3.5-15.0% by weight of surfactant.

The composition is preferably in the form or granules, wherein the granules comprise particles of 5-43pm size.

Preferably, the surfactant is one or more of polycarboxylate, lignosulfonate, alkyl naphthalene sulfonate, alkyl naphthalene sulfonate formaldehyde condensate salt, alkyl phenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, alkyl sulfate or alkyl sulfonate.

The herbicidal saflufenacil preparation may further comprise one or more conventional additives to improve the performance of the preparation. For instance the one or more conventional additives to improve the performance of the preparation are selected from defoamers, calcium and magnesium ion complexing agents, binders.

The herbicidal saflufenacil preparation may also further comprise a filler. For example, the filler may be selected from kaolin, light calcium carbonate, ammonium sulfate (potassium, sodium), diammonium hydrogen phosphate (potassium, sodium), ammonium chloride (potassium, sodium), ammonium nitrate (potassium, sodium), corn starch, white carbon black, sodium carbonate, sodium bicarbonate, sodium tripolyphosphate or mixtures thereof.

The herbicidal saflufenacil preparation according to any one of the preceding claims maybe prepared by the following process: 75-9 2 wt% saflufenacil, one or more surfactants and optionally one or more conventional additives or fillers are mixed and pulverized and the resultant product is granulated and dried.

In one embodiment, the herbicidal saflufenacil preparation may be produced by the following method: Saflufenacil, surfactant and filler are mixed uniformly and pulverized to 10-43pm in a jet mill; 10- 2 5wt% water is added and the mixture is kneaded to make a wet powder; the wet powder is then extruded into granules in a rotary granulator, dried at 50-100°C, and sieved to remove fine powder to provide saflufenacil (WDG).

In another embodiment, the herbicidal saflufenacil preparation may be produced by the following method: Saflufenacil, surfactant and filler are mixed uniformly and pulverized to 10-43pm in a jet mill; The resultant mixture is added to a boiling granulator or a disc granulator In the process, and spraying 5-15wt% atomized water is applied as a mist to granulate, The resultant wet granules are dried at 50-100°C, and sieved to remove fine powder to provide saflufenacil (WDG).

In yet another embodiment, the herbicidal saflufenacil preparation may be produced by the following method: Saflufenacil, surfactant and, where required, filler and water are mixed in a sand mill and ground to a particle size of 5-43pm; and the resultant material is spray granulated at 3.5MPa and 100-150°C, and sieved to remove fine powder to obtain saflufenacil (DF).

Specific scheme of the invention is as following: Method 1: Rotary extrusion granulation method: mix saflufenacil API, surfactant and filler evenly, crush the material to 10-43 pm in ajet mill, add 10- 2 5wt% water, knead into wet powder, then extrude into granules in a rotary granulator, dry at 50-100°C, and screen to remove fine powder to obtain saflufenacil WDG;

Method 2: Boiling granulation method: mixing saflufenacil API, surfactant and filler evenly, crushing the material to 10-43 pm in an airjet mill, adding into a boiling granulator or a disc granulator, spraying 5-15wt% atomized water for granulation, drying at 50-100°C, and sieving to remove fine powder to obtain saflufenacil WDG;

Method 3: spray granulation method: add saflufenacil API, surfactant, filler and proper amount of water into a sand mill, grind the materials to 5-43mu, spray granulate at 3.5MPa and 100-150°C, and screen to remove fine powder to obtain saflufenacil DF.

Specific implementation method The above scheme will be further explained with specific examples as below. It should be

understood that these examples are for illustrating the present invention and are not limited to limiting

the scope of the present invention. The implementation conditions adopted in the examples can be further adjusted according to the conditions of specific testers, and the unspecified implementation conditions are usually those in routine experiments.

Introduction and overview

Various aspects of the present invention will be described below. However, it is obvious to

those skilled in the field that the present invention can be implemented according to only some or all

aspects of the present invention. For the sake of illustration, specific numbers, materials and

configurations are given here, so that people can thoroughly understand the present invention. However,

it will be apparent to those skilled in the field that the present invention can be practiced without specific

details. In other examples, well-known features are omitted or simplified in order not to obscure the

present invention.

According to the general requirements of pesticide WDG and DF, the evaluation basis of the

embodiments of the invention is shown in Table 1 as below:

Table I Indicator name Standard value Note Active ingredients,%. 75-92.0 High Pcrformance Liquid Chromatography External mim Standard Method (HPLC)(X*XXX/WG/(M)/3) Suspension rate.%, m/m, 70 CIPAC MT168

Wetting time, s, S 30 CIPAC MT53.3.2 (dynamic)

Disintegration time. s, < 60 CIPACMT53.32 (dynamic)

Fineness (after 98 Wet screening method (through 0.043mm aperture) disintegration),%, > CIPAC MT185 Loss on drying, %. m/m, 2.5 CIPAC MT30.1

PH value (1% 4-7,5 CIPAC MT75 by PH meter suspension) I _II

Storage stability Qualified It passed the test after 14 days at 54L I°C

Example 1: preparation of 75wt% saflufenacil WDG

Weigh 78.1 g of 96wt% saflufenacil API (Nutrichem Co.,Ltd), 8.0 g of alkyl naphthalene

sulfonate formaldehyde condensate salt (Dispersant NNO; Nami (Thailand) Co., Ltd.), 2.0 g of alkyl

naphthalene sulfonate (SP-2888; Jiangsu Qingyu), 8 g of corn starch and 3.9 g of kaolin, mix them evenly, pulverize them into ultrafine powder with a particle size of 15-25tm in an air flow pulverizer, add them into a kneader, add 20 g of water, knead them into wet material, extrude them with a D1mm diameter rotary granulator, and granulate the wet particles in a boiling dryer at 70°C until water content is less than 2wt%, screen 12-60 particles to prepare 75wt% saflufenacil WDG with the appearance of

DImm cylindrical particles.

Example 2: preparation of 75wt% saflufenacil WDG

Weigh 78.1 g of 96wt% saflufenacil (Nutrichem Co.,Ltd), 8.0 g of lignosulfonate (REAX 85A,

REAX 910; Meadwestvaco), 3.0 g of alkylphenol polyoxyethylene polyoxypropylene ether (NPE-108;

Jiangsu Haian Petroleum Chemical Factory), 6.0 g of kaolin and 4.9 g of light calcium carbonate, mix

them evenly, pulverize them into ultrafine powder with a particle size of 15-25tm in an air flow

pulverizer, add them into a boiling granulator, slowly spray 16 g of water in boiling state, and heat them

to 60°C for drying until the water content is less than 2wt%, screen 24-60 particles to prepare 75wt%

saflufenacil WDG with irregular spherical appearance.

Example 3: preparation of 75wt% saflufenacil DF

Weigh 78.1 g of 96wt% saflufenacil API (Nutrichem Co.,Ltd), 15.0 g of lignosulfonate (REAX

85A, REAX 910; Meadwestvaco), 2.0 g of polycarboxylate (GY-DF85; Beijing Guangyuan Yinong),

0.5 g of defoaming agent (FLP; Shanghai Lansheng), 0.5 g of complexing agent (EDTA), 3.9 g of

ammonium sulfate and 100 g of water, mix them evenly, grind them in a sand mill to a suspension with

D50 of 5tm, spray granulate the suspension in a spray granulator at pressure of 3.5MPa and temperature

of 110°C, and screen 60-120 particles to prepare 75wt% saflufenacil DF with uniform small spherical

particles appearance.

Example 4: preparation of 80wt% saflufenacil WDG

Weigh 83.3 g of 96wt% saflufenacil (Nutrichem Co.,Ltd), 6.0 g of polycarboxylate (GY-DF85;

Beijing Guangyuan Yinong), 3.0 g of alkyl sulfonate (sodium dodecyl benzene sufonate; Nanjing Gige,

or NR500; Nanjing Taihua Chemical Co., Ltd.), 4.0 g of corn starch and 3.7 g of sodium sulfate, mix

them evenly, pulverize them into ultrafine powder with particle size of 15-25tm in an air-flow

pulverizer, add them into a kneader, add 18 g of water, knead them into wet material, extrude them with

a DImm diameter rotary granulator, and granulate them in a boiling dryer at temperature less than 65°C until water content is less than 2wt%, screen 12-60 particles to prepare 80wt% saflufenacil WDG with the appearance of DImm cylindrical particles.

Example 5: preparation of 80wt% saflufenacil WDG

Weigh 83.3 g of 96wt% saflufenacil API (Nutrichem Co.,Ltd), 6.0 g of sodium alkyl

naphthalene sulfonate (SP-2888; Jiangsu Qingyu), 2.0 g of polycarboxylate (GY-DF85; Beijing

Guangyuan Yinong), 3.0 g of alkyl sulfate (sodium lauryl sulfate (K12); Solvay), 0.5 g of defoamer

(FLP; Shanghai Lansheng), 2.0 g of adhesive (PVA1788; Shanghai Petrochemical Co., Ltd., or BP-17;

Hebei Guanlang Biotechnology Co., Ltd.) and 3.2 g of kaolin, mix them evenly, pulverize them into

ultrafine powder with a particle size of 15-25tm in an air flow pulverizer, add them into a boiling

granulator, slowly spray 16 g of water in boiling state, and heat them to 60°C until water content is less

than 2wt%, screen 24-60 particles to prepare 80wt% saflufenacil WDG with irregular spherical

appearance.

Example 6: preparation of 80wt% saflufenacil DF

Weigh 83.3 g of 96wt% saflufenacil (Nutrichem Co.,Ltd), 8.0 g of maleic acid-acrylic acid

copolymer (LAS-70; Jiangsu Qingting), 5.2 g of alkyl naphthalene sulfonate (SP-2888; Jiangsu

Qingyu), 2.0 g of alkyl sulfate (sodium lauryl sulfate (K12); Solvay), 0.5 g of defoaming agent (FLP;

Shanghai Lansheng), 1.0 g of adhesive (PVA1788; Shanghai Petrochemical Co., Ltd., or BP-17; Hebei

Guanlang Biotechnology Co., Ltd.) and 100 g of water, mix them evenly, grind them in a sand mill to

a suspension with D50 of 5tm, spray granulate the suspension in a spray granulator at pressure of

3.5MPa and temperature of 110°C, and screen 60-120 particles to prepare 80wt% saflufenacil DF with

uniform small spherical particles appearance.

Example 7: preparation of 90wt% saflufenacil WDG

Weigh 93.8 g of 96wt% saflufenacil (Nutrichem Co.,Ltd), 5.0 g of polycarboxylate (GY-DF85;

Beijing Guangyuan Yinong) and 1.2 g of alkylphenol polyoxyethylene polyoxypropylene ether (NPE

108; Jiangsu Haian Petroleum Chemical Factory), mix them evenly, pulverize them into ultrafine

powder with a particle size of 15-25tm in an air flow pulverizer, add them into a kneader, add 16 g of

water, knead them into wet materials, extrude and granulate them with a rotary granulator with a

diameter of D1mm, and dry them in a boiling dryer at 65°C until the moisture content is less than 2wt% and screen 12-60 particles to prepare 90wt% saflufenacil WDG with the appearance of Dlmm cylindrical particles.

Example 8: preparation of 90wt% saflufenacil WDG

Weigh 93.8 g of 96wt% saflufenacil (Nutrichem Co.,Ltd), 5.0 g of maleic acid-acrylic acid

copolymer (LAS-70; Jiangsu Qingting), 1.0 g of alkyl sulfonate (sodium dodecyl benzene sufonate;

Nanjing Gige, or NR500; Nanjing Taihua Chemical Co., Ltd.) and 0.2 g of sodium tripolyphosphate,

mix them evenly, pulverize them into ultrafine powder with particle size of 15-25pm in an air flow

pulverizer, add them into a boiling granulator, slowly spray 15 g of water in boiling state, heat to 60°C

and dry them until the water content is less than 2wt%, and screen 24-60 particles to prepare 90wt%

saflufenacil WDG with irregular spherical appearance.

Example 9: preparation of 90wt% saflufenacil DF

Weigh 93.8 g of 96wt% saflufenacil (Nutrichem Co.,Ltd), 2.5 g of maleic acid-acrylic acid

copolymer (LAS-70; Jiangsu Qingting), 3.2 g of lignosulfonate (REAX 85A, REAX 910;

Meadwestvaco), 0.5 g of defoamer (FLP; Shanghai Lansheng) and 100 g of water, mix them evenly,

grind them in a sand mill to a suspension with a D50 of 5tm, spray granulate the suspension in a spray

granulator at 110°C under pressure of 3.5MPa, and screen 60-120 particles to prepare 90wt%

saflufenacil DF with uniform small spherical particles appearance.

Example 10: preparation of 92wt% saflufenacil WDG

Weigh 95.8 g of 96wt% saflufenacil (Nutrichem Co.,Ltd) and 4.2 g of maleic acid-acrylic acid

copolymer (LAS-70; Jiangsu Qingting), mix them evenly, pulverize them into ultrafine powder with

particle size of 15-25tm in ajet mill, add them into a kneader, add 16 g of water, knead them into wet

material, extrude and granulate them with a rotary granulator with a diameter of Dlmm, dry the wet

particles in a fluidized bed dryer at 65°C until the water content is less than 2wt%, and screen 12-60

particles to prepare 92wt% saflufenacil WDG with the appearance of Dlmm cylindrical particles.

The related performance indicators of the saflufenacil preparations prepared in each example

all meet the technical requirements of the industry. The results are shown in Table 2 and Table 3:

Table 2: Example!I xampke2 Exatmpltc3 Fxample 4 Example 5

Idctr wrxi WJi DF AY. WTD( Itm

75wi 4 ' 75t 75wt%, 40t 0w% Active 75-9240 75.0 74.87 75.12 ISO20 8009 1 igh Performane ingredienK,,~ LtquidChromatography mm External Stmndard Method qIIPLC)(XXXXW6(M

Sn"siemsion 70.0 9(07 97,41 91,2 88,6 89,6 CIPACMT268 rate.' 0 n

Werilnuile. 10 60o 21.0 3110 14.0 22.0 CIPACMT5.3.3.2 S.s (dynamic) Disintegration 60 241.0o iIfA6.0 I8K0 21,01 c'IAcMT53..2 tujne!, < (dynamic) Fmnene i after 98 Qualified Qualified Qualified Qualified Qualified Wletscreeig methodi disinegraion)(through 0.043mm ... aperture) CIPAC

Lson2.5 1.7 2.2 210 1.6 2.8 CIPACMTAOI drying,%

P1 alue (11 4-7.5 58s 3,7 5.8 5. 1 5.1 ('IPAC MT75 byPH N, meter suspension) Storage Qualified Qualified Qualified Qualified Qualified Qualified It passed the test after stability ______2days at 54 fI A 14_____J_____

Table 3: Example Fxample7 Example8 Example 9 Fxample 10 Item Indicator DF WDG Wim DF WDG Method basis Requiremnt K 8w% 90wt% 9Owt% 90wt0 , 92wt¶ Active 75-920 79.78 9003 90.18 90,07 91 77 lligh Performance ingredients%. Liquid Chromaography inm External Standard Method (IIPLCXIXXX/W(i(M

Suspension 70,0 90.4 90,3 877 89.9 82.5 CIPAC MT168 rate.%, m/m.

Weting time, 30 27.0 15.0 23.0 30.0 16.0 CIPAC MT53.3.2 S.5 (dynamic) Disintegration 60 120 16.0 14.0 13.0 43.0 CIPAC MT5332 time, S. : (dynamic) Fineness (after 98 Qualified Qualified Qualified Qualified Qualified Wet screening method dismtegmiton) Ithrough 0043 mm . aperture) CIPAC MTI85

Loss on 25 2.2 1.4 1,7 2.3 2.2 CIPAC MT3O I drying. mIm, PH valueI 4-75 5.2 4.9 5A 5.0 48 CIPAC MT7 by lP suspnon)meter Storage Qualified Qualified Qualified Qualified Qualified Qualified It paied the test after stability 14 days at 54 f VC

The embodiment of the invention is used for the weed control test in soybean field, 100g of

effective ingredients per hectare are diluted by 2,500 times, and the control effect is investigated after

25 days. The results show that the effects of all the examples are slightly higher than those of the

commercial 70wt% saflufenacil WDG, as shown in Table 4 below:

Table 4: Dosage of Plant Fresh weight active control control effect Dosage Granulation Sample Specifications ingredients effect form mode (g/ha) Control Control effect(%) effect(%) Example I 75wt% WDG Extrusion 100 92.2 94.6 Example 2 75wt% WDG Boiling 100 89.7 91.3 Example 3 75wt% DF Spray 100 92.1 93.5 Example 4 80wt% WDG Extrusion 100 91.3 95.2 Example 5 80wt% WDG Boiling 100 91.8 93.4 Example 6 80wt% DF 100 92.4 87.5 Spray DF Example 7 90wt% WDG Extrusion 100 89.8 91.0 Example 8 90wt% WDG Boiling 100 93.3 92.4 Example 9 9Owt% DF Spray 100 92.2 93.8 Example 10 92wt% WDG Extrusion 100 85.3 85.7 Marketed 70Owt% WDG Extrusion 100 84.7 88.3 Artificial 90.3 84.6 weeding

The specific embodiments described above are only the preferred embodiments of the present invention. It should be pointed out that, for those of ordinary skill in the technical field, without departing from the principles of the present invention, several improvements or substitutions can be made, and these improvements or substitutions should also be regarded as the protection scope of the present invention.

The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Claims

26898671..DCC-26/03/2025 Claims

1. An herbicidal saflufenacil formulation, comprising saflufenacil as the sole active ingredient, one or more surfactants, wherein the content of saflufenacil is 75wt% - 92wt%, wherein the formulation is in a WDG (water dispersible granule) or a DF (dry flowable) form, and wherein the one or more surfactants is selected from polycarboxylate, lignosulfonate, alkyl naphthalene sulfonate, alkyl naphthalene sulfonate formaldehyde condensate salt, alkyl phenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, alkyl sulfate and alkyl sulfonate.

2. The herbicidal saflufenacil formulation according to claim 1, wherein the content of saflufenacil is 80wt% - 92wt%.

3. The herbicidal saflufenacil formulation according to claim 1 or claim 2, comprising 3.5wt% - 15.Owt% of surfactant.

4. The herbicidal saflufenacil formulation according to any one of claims 1 to 3, in the form or granules, wherein the granules comprise particles of 5-43pm size.

5. The herbicidal saflufenacil formulation according to any one of claims I to 4, further comprising one or more additives to improve the performance of the formulation.

6. The herbicidal saflufenacil formulation according to claim 5, wherein the one or more additives to improve the performance of the formulation are selected from defoamers, calcium and magnesium ion complexing agents, and binders, or a combination thereof.

7. The herbicidal saflufenacil formulation according to any one of claims I to 6, further comprising a filler.

8. The herbicidal saflufenacil formulation according to claim 7, wherein the filler is selected from kaolin, light calcium carbonate, ammonium sulfate (potassium, sodium), diammonium hydrogen phosphate (potassium, sodium), ammonium chloride (potassium, sodium), ammonium nitrate (potassium, sodium), corn starch, white carbon black, sodium carbonate, sodium bicarbonate, sodium tripolyphosphate or mixtures thereof.

9. The herbicidal saflufenacil formulation according to any one of claims 1 to 8 prepared by a process comprising: mixing the saflufenacil and the one or more surfactants, pulverizing the mixture, and granulating and drying the pulverized mixture.

26898671..DCC-26/03/2025

10. The herbicidal saflufenacil formulation according to any one of claims 1 to 8 produced by a method comprising: (i) mixing the saflufenacil, the one or more surfactants, and the one or more additives and/or the filler as required, uniformly and pulverizing the mixture to 10-43 pm in a jet mill; (ii) adding 10- 2 5wt% water to the pulverized mixture and kneading to provide a wet powder; and (iii) extruding the wet powder into granules in a rotary granulator; and (iv) drying the granules at 50-100°C, and sieving to remove fine powder to provide an herbicidal saflufenacil formulation in WDG form.

11. The herbicidal saflufenacil formulation according to any one of claims 1 to 8 produced by a method comprising: (i) mixing thesaflufenacil, the one or more surfactants, and the one or more additives and/or the filler as required, uniformly and pulverizing the mixture to 10-43 pm in a jet mill; (ii) adding the resultant mixture to a boiling granulator or a disc granulator to provide a granulate; (iii) spraying 5-15wt% atomized water as a mist onto the granulate to provide wet granules; and (iv) drying the resultant wet granules at 50-100°C, and sieving to remove fine powder to provide an herbicidal saflufenacil formulation in WDG form.

12. The herbicidal saflufenacil formulation according to any one of claims 1 to 8 produced by a method comprising: (i) mixing the saflufenacil, the one or more surfactants, the one or more additives and/or the filler as required, and water in a sand mill and grinding the mixture to a particle size of 5-43pm; and (ii) spray granulating the ground mixture at 3.5MPa and 100-150°C, and sieving to remove fine powder to provide an herbicidal saflufenacil formulation in DF form.

13. A process for preparing an herbicidal saflufenacil formulation according to any one of claims I to 8, the process comprising: mixing the saflufenacil and the one or more surfactants, pulverizing the mixture, and granulating and drying the pulverised mixture.

14. A method for preparing an herbicidal saflufenacil formulation, wherein the content of saflufenacil is 75wt% - 9 2 wt%, comprising:

(i) mixing saflufenacil and one or more surfactants uniformly and pulverizing the mixture to 10 43 pm in a jet mill; (ii) adding 10- 2 5wt% water to the pulverized mixture and kneading to provide a wet powder; and (iii) extruding the wet powder into granules in a rotary granulator; and (iv) drying the granules at 50-100°C, and sieving to remove fine powder to provide an herbicidal saflufenacil formulation in WDG form,

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wherein the one or more surfactants is selected from polycarboxylate, lignosulfonate, alkyl naphthalene sulfonate, alkyl naphthalene sulfonate formaldehyde condensate salt, alkyl phenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, alkyl sulfate and alkyl sulfonate, and wherein the herbicidal saflufenacil formulation comprises saflufenacil as the sole active ingredient.

15. A method for preparing an herbicidal saflufenacil formulation, wherein the content of saflufenacil is 75wt% - 9 2 wt%, the method comprising:

(i) mixing saflufenacil and one or more surfactants uniformly and pulverizing the mixture to 10 43 pm in a jet mill; (ii) adding the resultant mixture to a boiling granulator or a disc granulator to provide a granulate; (iii) spraying 5-15wt% atomized water as a mist onto the granulate to provide wet granules; and (iv) drying the wet granules at 50-100°C, and sieving to remove fine powder to provide an herbicidal saflufenacil formulation in WDG form, wherein the one or more surfactants is selected from polycarboxylate, lignosulfonate, alkyl naphthalene sulfonate, alkyl naphthalene sulfonate formaldehyde condensate salt, alkyl phenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, alkyl sulfate and alkyl sulfonate, and wherein the herbicidal saflufenacil formulation comprises saflufenacil as the sole active ingredient.

16. A method for preparing an herbicidal saflufenacil formulation, wherein the content of saflufenacil is 75wt% - 9 2 wt%, the method comprising:

(i) mixing saflufenacil, one or more surfactants and water in a sand mill and grinding the resultant mixture to a particle size of 5-43pm; and (ii) spray granulating the ground mixture at 3.5MPa and 100-150°C, and sieving to remove fine powder to provide an herbicidal saflufenacil formulation in DF form, wherein the one or more surfactants is selected from polycarboxylate, lignosulfonate, alkyl naphthalene sulfonate, alkyl naphthalene sulfonate formaldehyde condensate salt, alkyl phenol polyoxyethylene polyoxypropylene ether, ethylene oxide-propylene oxide block copolymer, maleic acid-acrylic acid copolymer, alkyl sulfate and alkyl sulfonate, and wherein the herbicidal saflufenacil formulation comprises saflufenacil as the sole active ingredient.

17. The method according to any one of claims 14 to 16, for preparing an herbicidal saflufenacil formulation wherein the content of saflufenacil is 80wt% - 92wt%.