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ZA200508026B - Fungicides containing methoxy acrylic acid methyl ester compound - Google Patents

Fungicides containing methoxy acrylic acid methyl ester compound Download PDF

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Publication number
ZA200508026B
ZA200508026B ZA200508026A ZA200508026A ZA200508026B ZA 200508026 B ZA200508026 B ZA 200508026B ZA 200508026 A ZA200508026 A ZA 200508026A ZA 200508026 A ZA200508026 A ZA 200508026A ZA 200508026 B ZA200508026 B ZA 200508026B
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South Africa
Prior art keywords
compound
powdery mildew
composition
mildew
cucumber
Prior art date
Application number
ZA200508026A
Inventor
Xu Tianming
Kong Xiaolin
Zheng Yunhong
Chen Dinghua
Zhu Weigang
Original Assignee
Zhejiang Chemical Industry Res
Zhejiang Hetian Chemical Co Lt
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Publication date
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Publication of ZA200508026B publication Critical patent/ZA200508026B/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734Ethers
    • C07C69/736Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

N 4
Fungicides Containing Methoxy Acrylic Acid Methyl Ester Compound
Field of the Invention
The present invention relates to a fungicide of methoxy acrylic acid methyl ester, 1.e. methyl methoxyacrylate, for agricultural use. More specifically, the present invention relates to a methyl mecthoxyacrylate compound having excellent fungicidal action, a process for producing it , a composition containing it , and its use as fungicides .
Background Art
US 4,914,128 have disclosed some methyl methoxyacrylate compounds, furthermore, the fungicidal action thercof has also been disclosed.
The present inventors discovercd unexpectedly that some compounds represented by the general formula disclosed in US 4,914,128 have cxtremely high fungicidal action, but their molecular structure are not definitely disclosed. Based on these, the present invention has completed.
Methyl methoxyacrylate fungicides are highly effective fungicides for agricultural usc, which are obtained by structural modification of the natural compounds.
These fungicides exhibit a broad-spectrum fungicidal action, lower biological toxicity and better environmental compatibility ~~ Many companies have researched and discovered several methyl mecthoxyacrylate fungicides with promising market. This kind of fungicide occupied more and more market shares and was supposed to become the dominating alternative species of triazole fungicides.
Summary of the Invention
The invention relates to novel methyl methoxyacrylate compound and its preparation methods, to a fungicidal compositions containing the methyl methoxyacrylate and its use as fungicides. The chemical name of methyl methoxyacrylate compound as fungicide is: methyl
! kl (E)-2-(2-((2,5-dimethylphenoxy)methylphenyl))-3-methoxyacrylate represented by the following formula:
CH, 0}
On =—0,
H,C CH,
O=ch,
I
The compound of the present invention can be prepared by following processes:
Process 1
Compound I can be prepared by the following reaction:
Hy . CH
J alkali o + OANA, _ oH, ¢ ° "ot,
CH, Ong, Hy Sc,
II II I
Compound II can be preparcd by following procedures: 2,5-dimethylphenol of formula II and methyl 2-(2-halomethylphenyl)-3-methoxyacrylate of formula III arc added to a suitable solvent, and then a suitable alkali is added, at an appropriate temperature, the mixture reacts for an appropriate period of time to obtain compound I, in which X represents leaving group such as halogen, preferably chlorine, bromine or iodine.
Solvent which can be preferably used is acetone or tetrahydrofuran.
Said alkali can be organic base or inorganic base. Specific examples of the organic base include triethylamine and pyridine ctc., and specific examples of the organic base include sodium hydroxide, potassium hydroxide, sodium hydride,
sodium carbonate and potassium carbonate ctc. The alkali preferably used in the present invention is sodium carbonate or potassium carbonate.
The temperature range preferably used in the above-mentioned reaction is about 0~100°C.
Process 2
Compound I can be prepared by the following reactions:
Hy p Hy
Me alkak & + eo
H HCP Hy HC
I Ivy Vv
Hy
HCOOCH, o mel tating spent Eh - 2? 0. alkali Oy a afkali He. Sch, 4 H,C 1 CH,
VI I
Compound I can be prepared by the following procedures: 2,5-dimethylphenol of formula IT and compound of formula I'V are added into a suitable solvent, then an appropriate alkali is added, the mixture reacts for an appropriate period of time at an appropriate temperature to obtain V. In compound TV, X represents leaving group such as halogen, preferably chlorine, bromine or iodine. Suitable alkali and an appropriate amount of methyl formate are respectively added into a solution of V in a suitable solvent. At an appropriate temperature, thc mixture reacts for an appropriate period of time to obtain Compound VI. Methylating agent such as dimethyl sulfate or iodomethane etc. is added into a solution of VI in a suitable solvent, followed by adding a suitable alkali. At an appropriate temperature, the mixture reacts for an appropriate period of time to obtain compound L.
When producing V, solvent preferably used is acetone and tetrahydrofuran. Said alkali can be organic base or inorganic base. Specific examples of the organic base include triethylamine and pyridine etc., and specific examples of the organic base include sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate and potassium carbonate etc. The alkali preferably used in the present invention is sodium carbonate or potassium carbonate. The temperature range preferably used in the reaction is about 0~100°C.
When producing VI, alkali preferably used is sodium methoxide or sodium hydride etc.; solvent preferably used is ether or methanol. The temperature range preferably used in the reaction is about -5~100° C.
When producing I, solvent preferably used is acetone or tetrahydrofuran. Said alkali can be organic base or inorganic base. Specific examples of the organic base include triethylamine and pyridine etc., and specific examples of the organic base include sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate and potassium carbonate ctc. The alkali preferably used in the present invention is sodium carbonate or potassium carbonate. The temperature range preferably used in the reaction is about 0~100°C.
Compound I of the present invention is an cffective fungicide, which is especially effective for controlling the following plant diseases: powdery mildew of wheat and barley, powdery mildew of vegetables, powdery mildew of melons, powdery mildew of fruit trees, powdery mildew of grape, powdery mildew of strawberry, and powdery mildew of flowers; stripc rust, leaf rust and other rust diseases of wheat and barley; downy mildew of cucumber, downy mildew of grape; anthracnose of melons, etc.
The invention also provided a fungicidal composition comprising the above-defined compound and the preparation processes thereof.
The composition of the invention preferably contains 0.1~99.0% by weight active ingredient of formula I, and suitable carriers and/or surfactants.
Process for producing the composition according to the present invention is
_ mixing compound I with at least one carricr. The composition can also contain other active ingredient of pesticides.
The carriers of the present invention can be substances that satisfy the following conditions: after mixing the carriers with active ingredient(s), the composition formed are conveniently used to the locations need to be treated, for example, the locations can be plant, seed or soil; or the composition can be advantageous for storing, shipping or operation. Carriers can be solid or liquid, and can be any carrier which is conventionally used in the composition of pesticides and bactericides.
Suitable solid carriers include natural and synthetic silicates such as diatomaceous earth, talc, attapulgite, aluminum silicate (kaolin), montmorillonite, and mica; calcium carbonate, calcium sulfate, ammonium sulfate; synthetic oxidized calcium silicate or oxidized aluminum silicate; elements such as carbon and sulfur; natural and synthetic resins such as benzofuran resin, polyvinyl chloride and styrcne polymer and copolymer; solid polychlorophenol; asphalt; waxes such as beeswax, paraffin.
Suitable liquid carriers include water; alcohols such as isopropyl alcohol and ethanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ether; aromatic hydrocarbons such as benzcne, toluene, xylenc; petroleum fractions such as kerosene and mineral oil; chlorinated hydrocarbons such as carbon tetrachloride, perchloroethylene and trichloroethanc. Generally, the mixture thereof are also appropriate.
The composition with other pesticides and bactericides are usually manufactured in concentrated form for shipping convenience. Users should dilute the composition before use. Small amount of surfactant as carrier is helpful for dilution. Therefore, the composition of the present invention preferably contain surfactant.
Said surfactant can be emulsifier, dispersant or wetting agent: it can be ionic surfactants or nonionic surfactants such as sodium salt or calcium salt of
® polyacrylic acid and lignosulfonic acid; fatty acid or fatty amine or amide having at least 12 carbon atoms; condensation compounds of ethylene oxide and/or propylene oxide; fatty acid ester of glycol, sorbitol, sucrose or pentaerythritol, and the condensation compounds thereof with ethylene oxide and/or propylene oxide; fatty alcohol or alkyl phenol such as paraoctyl phenol or the condensation compounds thereof with propylene oxide and/or ethylene oxide; sulfate or sulfonate of the above-mentioned condensation compounds; alkali metal or alkaline earth metal salts of sulfate or sulfonate having at least 10 carbon atoms, and sodium salts such as sodium lauryl sulfate, sodium secondary alkyl sulfate, sodium salt of sulfonated castor oil, sodium salt of alkyl aryl sulfonate such as sodium dodecyl benzene sulfonate are preferable.
The specific examples of the composition according to the present invention can be wettable powders, dusts, granules, emulsifiable concentrates, cmulsions, suspension concentrates, smoke aerosols and aerosols. Said wettable powders usually contain 20~80wt% active ingredient, and usually contain 2~10wt% dispersant in addition to solid inert carriers, and adding 0~10wt% stabilizer and/or other additives such as penetrant or agglutinant if necessary. Said dusts are usually manufactured into dust concentrates and the compositions thercof are similar to the wettable powders except for the existence of dispersant, the dust concentrates can be further diluted with solid carriers in the field before its use, and the compositions obtained by dilution usually contain 0.5~10wt% active ingredients. Said granules are usually manufactured into 10-100 screen mesh by using conglobation or infusion technology. Said granules usually contain 0.1~ 80wt% active ingredient and 0~ 10wt% other additives such as stabilizer, surfactant, slow release agent etc. Said “flowable dry powder” contains the smaller granules with the relatively higher concentration of the active ingredient.
Said emulsifiable concentrates usually contain 1~50% w/v active ingredient, 2~20% w/v emulsifier and 0~20% w/v othcr additives such as stabilizer, penctrant and corrosion inhibitor in addition to solvent, and may contain cosolvent if necessary. Said suspension concentrates usually contain 10~80wt% active ingredient, 0.5~ 15wt% dispersant, 0.1~10wt% other additives such as defoamcr, corrosion inhibitor, stabilizer, penetrant and agglutinant.
®
For water dispersants and emulsions, for example, the compositions obtained by diluting the wettable powders or the concentrates according to the present invention with water are also included in the scope of the present invention. Said emulsions can be W/O-emulsion or O/W-emulsion.
A compositions with a boarder-spectrum fungicidal action than that of compound (1) alone are obtained by adding other one or more fungicides thereto. In addition, other fungicides can produce synergism to the fungicidal action of compound (I). Specific examples of the compounds as fungicides which can be added in the compositions of thc present invention arc captan, thiophal, pyrimethanil, tridemorph, fenarimol, fludioxonil, cuprous oxide, difenoconazole, zincb, mancozeb, thiram, difolatan, iprodione, methyl-dichlozoline, hexaconazole, tebuconazole, pencycuron, cymoxanil, myclobutanil, guazatine acetate, prothiocarb, cyclafuramid, flumorph, flusilazole, SSF-129, picoxystrobin, metrafenone, pyraclostrobin, resveratro, dimoxystrobin, UBF-307, BASF490F,
ICIA5504, TH-164, RH7592, diniconazole, flutolanil, carbendazim, benomyl, triadimefon, cyproconazole, diethofencarb, thiophanate-methyl, hymexazol, fenpropimorph, propamocarb, metalaxyl, furalaxyl, benalaxyl, oxadixyl, methasulfocarb, pyrifenox, fenpropidin, mepanipyrim, dimethomorph, fenpiclonil, propiconazole, chlorothalonil, diazinon, cupric sulfate, dichlofluanid, phosethyl-Al, hymexazol and the like.
Specific examples of insecticides which can be mixed with the compounds of the present invention to form the compositions are bromopropylate, dicofol, 1605-methyl, 1605, fenitrothion, diazinon, carbosulfan, chlorpyrifos, fipronil, chlorfenapyr, methomyl, monosultap, bisultap, cartap , avermectins, permethrin, cypermethrin, tetramethrin, tcfluthrin, cyfluthrin, fenvalerate, cypermethrin, flufenoxuron, triflumuron, chlorfluazuron, fenpyroximate, imidacloprid, fenoxycarb, triazophos, fenazaquin, diafenthiuron, pyridaben, clofentezine etc.
Some compounds are synthesized by the inventors in order to control various fungi diseases only using very small amount thc compounds, these compounds exhibit a broad-spectrum fungicidal action for controlling the diseases in the plant caused by various fungi such as phycomycetes, oomycetes, ascomycetes and deuteromycetes ctc. , and a low dosage of these compounds is needed to obtain the satisfactory effect of controlling the diseases duc to their excellent biological activity. These compounds exhibit good biological activity not only for controlling powdery mildew, downy mildew and anthracnose, but also for controlling black pox and white rust of grape.
The compound provided by the present invention not only has very high biological activity, but also is friendly to environment and has no environmental pollution.
Furthermore, the compound can lower cost compared with that of other similar products, and thus is a novel promising fungicide for agricultural use.
Description of the Preferred Embodiments
Then the present invention will be described more specifically by the following examples. However, the present invention should not be restricted to them in any way. Unless otherwise indicated, all parts in the present invention are by weight.
Synthesis example
Into a 500ml three-necked flask containing 150ml of anhydrous acetone, 12.2 g of 2,5-dimethly phenol was added at room temperature, then 13.8 g of potassium carbonate was added . The solution was stirred for 20 minutes at room temperature, then 28.5 g of methyl (E)-2-[2-(bromomethyl)phenyl]-3-methoxyacrylate was slowly added into the reaction mixture. The mixture was refluxed for 3 hours.
The reaction mixture was filtered and concentrated in vacuum to give the crude product. The crude product was purified by column chromatography using ethyl acetate: petroleum ether (1:4) as eluant to give 26.08 g of white solid (yield 80%).
Melt point: 108~110°C '"HNMR:2.235(3H,s), 2.279(3H,s), 3.706(3H,s), 3.835(3H,s), 4.944(2H.s), 6.584(1H,s), 6.655-6.673(1H,d), 7.013-7.032(1H,d), 7.164-7.168(2H,d), 7.300-7.382(2H,m), 7.596(1H,s), 7.617(1H,s)
Note: "HNMR spectrum was recorded using CDCl; as solvent. The abbreviation used in the data is as follows: NMR=nucleic magnetic resonance, s=single peak,
d=double peaks and m=multiple peaks.
Formulation Examples
Formulation Example
Compound of the present invention (40 kg), diatomaccous carth (53 kg), C12-20 alcohol sulfate (4 kg), and sodium dodecyl benzene sulfonate (3 kg) were homogeneously mixed together and ground to give a wettable powder containing 40% active ingredient.
Formulation Example 2
Compound of the present invention (30 kg), xylene (33 kg), dimethylformamide (30 kg), and polyoxyethylene alkylpropyl ether (7 kg) were homogeneously mixed together, and dissolved to give a emulsion containing 30% active ingredient.
Formulation Example 3
Compound of the present invention (10 kg), talcum powder (89 kg), and polyoxycthylene alkylpropyl ether (1 kg) were homogeneously mixed together, and ground to give a dust containing 10% active ingredient.
Formulation Example 4
Compound of the present invention (5 kg), clay (73 kg), bentonite (20 kg), sodium dioctyl thiosuccinate (1 kg) and sodium phosphate (1 kg) were homogeneously mixed together and ground adequately, then an appropriate amount of water was added, and homogeneously mixed again, granulated and dricd to give a granule containing 5% active ingredient.
Formulation Example 5
Compound of the present invention (10 kg), sodium lignosulfonate (4 kg), sodium dodecyl benzene sulfonate (1 kg), xanthic acid (1 kg) and water (84 kg) were homogeneously mixed together. The above mixture were ground by wet grind process to give particles with the granularity smaller than 1 micron, and a colloidal suspension containing 10% active ingredient was obtained.
Formulation Example 6
_
Compound of the present invention (8 kg), mancozeb (50 kg), kaolin (30 kg), sodium dodecyl benzene sulfonate (4 kg) and sodium lignosulfonate(8 kg) were homogeneously mixed together, and the mixture was adequatcly ground to give a wettable powder containing 8% active ingredient.
Formulation Example 7
Compound of the present invention (1 kg), triazolone (20 kg), kaolin (64 kg), sodium dodecyl! benzene sulfonate (6 kg) and sodium lignosulfonate (9 kg) were homogeneously mixed together , and the mixture was adequately ground to give a wettable powder containing 1% active ingredient.
Effect examples
The compound of the present invention has better biological activity than the known fungicides, can effectively control discases caused by fungi with a very low dosage, and is particularly effective for controlling following disease: powdery mildew, rust diseases, downey mildew, anthracnose , such as powdery mildew of wheat and barley, powdery mildew of cucumber, powdery mildew of pumpkin, powdery mildew of strawberry, powdery mildew of grape, rust diseases of wheat and barley, downey mildew of grape, downey mildew of cucumber, anthracnose of cucumber. In addition, it can inhibit black pox and white rust of grape to a certain extent.
Effect example 1
The prevention and treatment tests for controlling powdery mildew of cucumber (in the green house)
The fungicide used in the test was compound I (emulsifiable oil containing 5% of compound I, and six concentrations 10, 5, 2.5, 1.25, 0.625, 0.3125 ppm were designed. To compare with ZA-1963 (i.e. picoxystrobin, manufactured by
Syngenta Company, a compound commercially available which had been described in the resemble patent) (emulsifiable oil containing 5% of ZA-1963), six concentrations 10, 5, 2.5, 1.25, 0.625, 0.3125 ppm were designed. To compare with emulsifiable oil containing 20% of triazolone, thrce concentrations 100, 50,
_ ppm were designed. Some pot-grown cucumber healthy seedlings with two opened true leaves, which grew up to the period of two leaves with onc bud, were selected and sprayed. 24 hours after spraying with the tested compound, the prevention test was carried out by inoculation; 24 hours after inoculation, the treatment test was carried out by spraying with the tested compound. The inoculated cucumber scedlings were placed into an artificial climate chamber to be cultivated in humidity. The prevention and treatment effect was investigated after 7 days. The results are shown in Table 1.
Table 1 Results of tests for controlling powdery mildew of cucumber
Fungicides , or) 0 ww [ww]
Compound
P1963
IEEE A
SE EC: N— tiazolone | SO | 82
IEC ET
Results of the prevention and treatment tests demonstrate that the prevention effect of compound I is slightly better than the treatment effect thereof. When the concentration of compound I is 0.625 ppm, the prevention effect is 85.31%, while the treatment effect is 64.81%. At the same time, the prevention effect and the treatment effect of compound I are obviously better than that of ZA-1963, especially for the treatment effect. It is clcarly that the biological activity of
® compound I is much better than that of triazolone.
Effect example 2
The prevention and treatment tests for controlling powdery mildew of wheat (in the green house)
The fungicide ed in the tests was compound I (cmulsifiable oil containing 5% of compound I), and six concentrations 25, 12.5, 6.25, 3.125, 1.563, 0.781 ppm were designed. To compare with ZA-1963 (i.c. picoxystrobin, manufactured by
Syngenta Company, a compound commercially available which had been described in the resemble patent) (emulsifiable oil containing 5% of ZA-1963), six concentrations 25, 12.5, 6.25, 3.125, 1.563, 0.7815 ppm were designed. To compare with emulsifiable oil containing 20% of triazolone, three concentrations 100, 50, 25 ppm were designed. Some pot-grown wheat, which grew up to the period of two leaves with one bud, was selected and sprayed. 24 hours after spraying with the tested compounds, the prevention tests were carried out by inoculation; 24 hours after inoculation, the treatment tests were carried out by spraying with the tested compounds. The inoculated wheat was placed into an artificial climate chamber to be cultivated in humidity. The prevention and treatment effect was investigated after 7 days. The results are shown in Table 2.
_
Table 2 Results of tests for controlling powdery mildew of wheat
EE nT ww] ns ww
Compound es [ww @
P1963 ow
Ee I I I
EE A A
Results of the prevention and treatment tests demonstrate that the prevention and treatment effect of compound I is obviously better than that of ZA-1963, especially for the treatment effect. The biological activity of compound 1 is much better than that of triazolone.
Effect example 3
Simulation field tests for controlling powdery mildew of wheat
Treating concentrations of compound I were 50, 25, 12.5, 6.25, 3.125 ppm, treating concentrations of the compared fungicide ZA-1963 were the same as these of compound I, while treating concentrations of triazolone were 100, 50, 25 ppm.
Cultivating pot-grown wheat to the 4-5-lcaf period, and taking its own course to bad until the metaphase of powdery mildew of wheat, the infected leaves were sprayed using the tested compounds with the concentrations mentioned above.
The prevention and treatment effect was investigated after 10 days. The results are shown in Table 3.
Table 3 Results for controlling powdery mildew of wheat in simulation field test 2 0] eo
Compound @
EEE
Parse:
Triazolone
Results of the simulation field test demonstrate that the pot-grown wheat when taking its own coursc to bad until the metaphase was sprayed using compound I, the control effect thereof is still excellent, and the control effect is better than that of the compared fungicides ZA-1963 and triazolone.
Effect example 4
Duration tests
Treating concentrations of compound | and ZA-1963 were 50, 25 mg/l. The test object was the powdery mildew of wheat. The pot-grown wheat was sprayed when two true Icaves thereof were opened. 24 hours after spraying, E. graminis f-sp.tritici of wheat was inoculated to the tested plant, and then the inoculated wheat was placed into the green housc to be cultivated in humidity. The control effect was investigated after 7, 10, 15, 20, 25, 30 days. The results are shown in
Table 4.
Table 4 Results of duration tests . Concentration Control effect (%)
Fungicides (mg/l) 10days | 15days | 20days
Compound | ___50___| 100 | too | 6 | lo 0 CER 643 | wa
ZA-1963 | 100 | 100 | wo [iw | %a1 | mies
The results of duration tcsts demonstrate that the duration of compound 1 is slightly longer than that of ZA-1963 when the artificial inoculation is carried out in the green house.
Effect example 5
The tests for controlling powdery mildew of pumpkin (in the field)
The field tests for controlling powdery mildew of pumpkin were carried out in the sheds at Modern Agriculture District in Shaoxing City, Zhejiang province of China in June 2002.
Four concentrations of compound I (aqucous suspension containing 10% of compound I 50, 25, 12.5, 6.25 ppm were designed. To compare with thc compared fungicide triazolone EC (20%), the concentration of triazolone EC was 100 ppm. The control test was carried out using water. Onc treatment was repeated for four times. The effect was investigated after 7 days. The results are shown in Table 5.
Table 5 The test results for controlling powdery mildew of pumpkin (in the field) trati Di | t of
Fungicides Concentration |56A58 neremen © Control effect (%) (ppm) index | disease index
Compound ms 1 | wa o [m5 [ms] 3s | ws |]
Note: Values in the CK column of the control effect are the increment value of the discasc index.
It is illustrated from Table 5 that compound I with the concentration of 6.25 ppm has very high activity for controlling powdery mildew of pumpkin, the cffect is obviously better than that of the compared fungicide triazolone.
Effect example 6
The tests for controlling powdery mildew of cucumber (in the field)
The ficld tests for controlling powdery mildew of cucumber were carried out in the sheds at Modern Agriculture District in Shaoxing City, Zhejiang province of
China in June 2002.
Four concentrations of compound I (aqueous suspension containing 10% compound I 50, 25, 12.5, 6.25 ppm were designed. To compare with the compared fungicide triazolone EC (20%), the concentration of triazolone EC was 100 ppm. The control test was carried out using water. One treatment was repeated for four times. The effect was investigated after 7 days. The results are shown in Table 6.
Table 6 The test results for controlling powdery mildew of cucumber (in the field)
Fungicides Disease index . i (ppm) discasc index (%)
Compound 0
C&O ms | ms | ws
Note: Values in the CK column of the control effect are the increment value of the disease index.
It is illustrated from Table 6 that compound I with the concentration of 6.25 ppm has very high activity for controlling powdery mildew of cucumber, the effect is obviously better than that of the compared fungicide triazolone.
Effect example 7
The tests for controlling downey mildew of cucumber (in the green house)
Treating concentrations of compound I were 100, 50, 25, 12.5, 6.25, 3.125 ppm,
The concentration of the compared fungicide ZA-1963 were same as that.
Treating concentration of metalaxy is 500 ppm. Some pot-grown cucumber healthy seedlings with two opened true leaves, which grew up to the period of two leaves with one bud, were sclected and sprayed. 24 hours after spraying with the tested compounds, prevention test was carried out by inoculation; 24 hours after inoculation, treatment test was carried out by spraying with the tested compounds.
The inoculated seedlings were placed into an artificial climate chamber to be cultivated in humidity. The prevention and treatment effcct was investigated after 7 days. The results are shown in Table 7.
Table 7 Results of tests for controlling downy mildew of cucumber (in the green house) — wm [wm ®
The control effect of compound I is obviously better than that of the compared fungicide ZA-1963 and mctalaxyl with the same concentration in the green house.
Effect example 8
The tests for controlling downey mildew of grape (in the ficld)
The tests in the field for controlling downy mildew of grape were carried out at the
Agriculture Technology Demonstration Farm in Stone Bridge village, Dangtu
County, Maanshan city, Anhui province in July 2002.
Five concentrations of compound I (emulsifiable oil containing 5% of compound I) 200, 100, 50, 25, 12.5 ppm were designed, treating concentrations of the compared fungicide the wettable powder of Curzate (72%) manufactured by Du Pont was 1000ppm, and another was the blank control test. One treatment was repeated for four times. 7 days after spraying, the effect was investigated. The results are shown in Table 8.
Table 8 Results of tests for controlling downy mildew of grape (in the field) (ppm) using fungicides | index
Compound 0 (Cum | 0 [1s | Te | wey
Tok [www]
It is demonstrated from the above results that the effect of compound I for controlling downey mildew of grape with the concentration of 200 ppm is comparative with that of thc compared fungicide Curzate with the concentration of 1000 ppm.
Effect example 9
The tests for controlling downey mildew of cucumber (in the field)
The tests in the field for controlling downy mildew of cucumber were carried out at the Agriculture Technology Demonstration Farm in Stone Bridge village,
Dangtu County, Maanshan city, Anhui province in July 2002.
Five concentrations of compound I (emulsifiable oil containing 5% of compound 1) 200, 100, 50, 25, 12.5 ppm were designed, treating concentrations of the compared fungicide the wettable powder of Curzate (72%) manufactured by Du Pont was 1000ppm, and another was the blank control test. One treatment was repeated for four times. 7 days after spraying, the effect was investigated. The results are shown in Tablc 9.
Table 9 Results of tests for controlling downy mildew of cucumber (in the field) (ppm) fungicides index ns | os [3m [sw
Compound 0 ok [om [es
It is demonstrated from the above results that the effect of compound I for controlling downey mildew of cucumber with the concentration of 200 ppm is comparative with that of the compared fungicide Curzate with the concentration of 1000 ppm.
Effect example 10
The tests for controlling anthracnose of cucumber (in the green house)
Treating concentrations of compound I and the compared fungicide ZA-1963 were 500, 250, 125, 62.5, 31.25 ppm. The test object was anthracnose of cucumber.
The pot-grown cucumber seedlings were sprayed when they grew up to the period of one true leaf. 24 hours after spraying, the spore suspension of anthracnose was inoculated, then the inoculated seedlings were placed into an artificial climate chamber maintaining the relative humidity of 100% and the temperature of 20°C. 24 hours after inoculation, the relative humidity 85% in the artificial climate chamber was maintained. The effect was investigated after 7 days. The results are shown in Table 10.
Table10 Results of tests for controlling anthracnose of cucumber (in the green house)
Compound @
Za196
The prevention and treatment effect of compound I is slightly better than that of the compared fungicide ZA-1963 with the samc concentration in the green house.

Claims (9)

Claims:
1. A fungicidal composition of methoxyl methylacrylate wherein said composition contains a compound represented by formula (I) and its isomers , CH, 0} Of/ 0, H,C CH, O~cH 3 M
2. The fungicidal composition according to claim 1, wherein said composition contains 0.1-99.0wt% compound (I) as active ingredient.
3. The fungicidal composition according to claim 1 or 2, wherein said compound (I) can be formulated into emulsions, dusts, wettable powders, suspension and granules.
4. A using method of the fungicidal composition according to any one of claims 1-3, wherein said composition can be used independently or used in a binary or ternary mixing formulations with one or more bactericides, pesticides , herbicides or plant-growth regulators.
S. The using method of the composition according to claim 4, wherein the composition can be uscd on plants to control diseases of various plants caused by a broad range of fungi such as phycomycetes, oomycetes, ascomycetes and deuteromycetes.
6. The using mcthod of the composition according to claim 4, wherein the composition can be used on plants to control powdery mildew of cereals, powdery mildew of melons, rust diseases of cereals, powdery mildew of vegetables, powdery mildew of fruits, powdery mildew of flowers; downey mildew of cucumber, downey mildew of grape; anthracnose of cucumber.
7. A fungicidal compound according to claim 1, said compound is a compound represented by formula (I) and its isomers , CH, Oo On/ 0, H,C CH, O~cH, (D
8. The method for producing the compound according to claim 7, wherein compound (I) can be obtained by the reaction of compound (II) and compound (III) in the present of alkali, He lp alkali Sta + —— o Ren, & o % on ¢ Hy Osen, Hy Och, II III I in compound (III), X represents leaving group, the reaction can be carried out in solvent if necessary.
9. The method for producing the compound according to claim 7, wherein compound (I) can be prepared by the following reactions: &* = & atkali + — ° CH, HCO Hy HC jit v Vv CH, HCOOCH, melhivlating spesit CH © o Ihali or o a Bali MH nw alkal " iC Son, HC Lon, CH, VI 1
ZA200508026A 2003-03-25 2005-10-04 Fungicides containing methoxy acrylic acid methyl ester compound ZA200508026B (en)

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Families Citing this family (174)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101524076B (en) * 2005-08-17 2012-11-07 浙江省化工研究院有限公司 Fungicide composition
CN100401889C (en) * 2005-08-17 2008-07-16 浙江化工科技集团有限公司 Fungicide composition
CN101642119B (en) * 2009-08-24 2013-06-05 陕西上格之路生物科学有限公司 Agricultural sterilizing composition containing kresoxim-methyl benzene
JP2013502412A (en) 2010-04-21 2013-01-24 オスコテク インコーポレイテッド α-Arylmethoxyacrylate derivative, process for preparing the same and pharmaceutical composition containing the same
CN102115458B (en) * 2010-11-25 2019-12-13 大连九信精细化工有限公司 Synthetic method of 3-methoxy-2-aryl methyl acrylate compound
CN102919240B (en) * 2010-12-08 2014-08-13 陕西美邦农药有限公司 Tridemorph-containing sterilizing composition
CN102835399B (en) * 2012-09-27 2014-04-30 陕西上格之路生物科学有限公司 Metrafenone-containing bactericidal composition
CN103975927B (en) * 2013-04-07 2016-06-08 海南正业中农高科股份有限公司 A kind of bactericidal composition containing cyflufenamid and pyraoxystrobin or ZJ0712 and application
CN103598193B (en) * 2013-10-23 2015-04-01 江苏丰登作物保护股份有限公司 Picoxystrobin and thiram containing sterilization composition and application thereof
AU2015342067B2 (en) 2014-11-07 2019-10-31 Basf Se Pesticidal mixtures
WO2016174042A1 (en) 2015-04-27 2016-11-03 BASF Agro B.V. Pesticidal compositions
WO2017076757A1 (en) 2015-11-02 2017-05-11 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3370525A1 (en) 2015-11-04 2018-09-12 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
BR112018009566A2 (en) 2015-11-13 2018-11-06 Basf Se compounds, mixture, agrochemical composition, use of compounds and method to combat phytopathogenic harmful fungi
EP3373733A1 (en) 2015-11-13 2018-09-19 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
CA3003949A1 (en) 2015-11-19 2017-05-26 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
CA3003946A1 (en) 2015-11-19 2017-05-26 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3202267A1 (en) 2016-02-05 2017-08-09 Basf Se Pesticidal mixtures
EP3205208A1 (en) 2016-02-09 2017-08-16 Basf Se Mixtures and compositions comprising paenibacillus strains or fusaricidins and chemical pesticides
WO2017153200A1 (en) 2016-03-10 2017-09-14 Basf Se Fungicidal mixtures iii comprising strobilurin-type fungicides
BR112018068695B1 (en) 2016-03-16 2022-12-27 Basf Se USE OF A COMPOUND AND METHOD TO CONTROL PHYTOPATHOGENIC FUNGI
CA3015744C (en) 2016-03-16 2024-04-23 Basf Se Use of 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one for combating resistant phytopathogenic fungi on cereals
WO2017157916A1 (en) 2016-03-16 2017-09-21 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
BR112018069897B1 (en) 2016-04-11 2023-01-17 Basf Se COMPOUND OF FORMULA I, AGROCHEMICAL COMPOSITION, PROCESS FOR PREPARING COMPOUNDS OF FORMULA I, NON-THERAPEUTIC USE OF COMPOUNDS AND METHOD FOR COMBATING HARMFUL PHYTOPATHOGENIC FUNGI
CN105766919A (en) * 2016-04-22 2016-07-20 广东中迅农科股份有限公司 Bactericidal composition containing triflumizole and (E)2-[2-(2, 5-dimethylphenoxytoluene)-phenyl]-3-methoxyacrylate
US20190200612A1 (en) 2016-09-13 2019-07-04 Basf Se Fungicidal mixtures i comprising quinoline fungicides
WO2018054723A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018054721A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018054711A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018065182A1 (en) 2016-10-04 2018-04-12 Basf Se Reduced quinoline compounds as antifuni agents
WO2018073110A1 (en) 2016-10-20 2018-04-26 Basf Se Quinoline compounds as fungicides
US20190322631A1 (en) 2016-12-19 2019-10-24 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3339297A1 (en) 2016-12-20 2018-06-27 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3338552A1 (en) 2016-12-21 2018-06-27 Basf Se Use of a tetrazolinone fungicide on transgenic plants
EP3571190A1 (en) 2017-01-23 2019-11-27 Basf Se Fungicidal pyridine compounds
WO2018149754A1 (en) 2017-02-16 2018-08-23 Basf Se Pyridine compounds
WO2018153730A1 (en) 2017-02-21 2018-08-30 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
CN116082366A (en) 2017-03-31 2023-05-09 巴斯夫欧洲公司 Pyrimidinium compounds and mixtures thereof for combating animal pests
US20200187500A1 (en) 2017-04-06 2020-06-18 Basf Se Pyridine compounds
EP3606912A1 (en) 2017-04-07 2020-02-12 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2018188962A1 (en) 2017-04-11 2018-10-18 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
TW201838965A (en) 2017-04-20 2018-11-01 印度商Pi工業公司 Novel phenylamine compounds
US20210084902A1 (en) 2017-05-02 2021-03-25 Basf Se Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
WO2018202491A1 (en) 2017-05-04 2018-11-08 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
EP3619207B1 (en) 2017-05-04 2021-06-23 Basf Se Substituted 5-(haloalkyl)-5-hydroxy-isoxazolines for combating phytopathogenic fungi
EP3618628A1 (en) 2017-05-05 2020-03-11 Basf Se Fungicidal mixtures comprising triazole compounds
WO2018210661A1 (en) 2017-05-15 2018-11-22 Basf Se Heteroaryl compounds as agrochemical fungicides
WO2018210658A1 (en) 2017-05-15 2018-11-22 Basf Se Heteroaryl compounds as agrochemical fungicides
WO2018210659A1 (en) 2017-05-15 2018-11-22 Basf Se Heteroaryl compounds as agrochemical fungicides
WO2018210660A1 (en) 2017-05-15 2018-11-22 Basf Se Heteroaryl compounds as agrochemical fungicides
EP3630731B1 (en) 2017-05-30 2023-08-09 Basf Se Pyridine and pyrazine compounds for combating phytopathogenic fungi
WO2018219797A1 (en) 2017-06-02 2018-12-06 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2018234139A1 (en) 2017-06-19 2018-12-27 Basf Se 2-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryloxy](thio)acetamides for combating phytopathogenic fungi
WO2019002158A1 (en) 2017-06-30 2019-01-03 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019025250A1 (en) 2017-08-04 2019-02-07 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019038042A1 (en) 2017-08-21 2019-02-28 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019042800A1 (en) 2017-08-29 2019-03-07 Basf Se Pesticidal mixtures
WO2019042932A1 (en) 2017-08-31 2019-03-07 Basf Se Method of controlling rice pests in rice
EP3453706A1 (en) 2017-09-08 2019-03-13 Basf Se Pesticidal imidazole compounds
WO2019052932A1 (en) 2017-09-18 2019-03-21 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019057660A1 (en) 2017-09-25 2019-03-28 Basf Se Indole and azaindole compounds with substituted 6-membered aryl and heteroaryl rings as agrochemical fungicides
WO2019072906A1 (en) 2017-10-13 2019-04-18 Basf Se Imidazolidine pyrimidinium compounds for combating animal pests
EP3713936B1 (en) 2017-11-23 2021-10-20 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019115511A1 (en) 2017-12-14 2019-06-20 Basf Se Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
US11839214B2 (en) 2017-12-15 2023-12-12 Basf Se Fungicidal mixture comprising substituted pyridines
WO2019121143A1 (en) 2017-12-20 2019-06-27 Basf Se Substituted cyclopropyl derivatives
WO2019123196A1 (en) 2017-12-20 2019-06-27 Pi Industries Ltd. Fluoralkenyl compounds, process for preparation and use thereof
WO2019145140A1 (en) 2018-01-09 2019-08-01 Basf Se Silylethynyl hetaryl compounds as nitrification inhibitors
WO2019137995A1 (en) 2018-01-11 2019-07-18 Basf Se Novel pyridazine compounds for controlling invertebrate pests
WO2019150311A1 (en) 2018-02-02 2019-08-08 Pi Industries Ltd. 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms
BR112020014817A2 (en) 2018-02-07 2020-12-08 Basf Se USE OF COMPOUNDS OF FORMULA I, COMPOUNDS OF FORMULA I, COMPOSITION, USE OF A COMPOUND OF FORMULA I, METHOD FOR COMBATING PHYTOPATHOGENIC FUNGI AND SEED
WO2019154665A1 (en) 2018-02-07 2019-08-15 Basf Se New pyridine carboxamides
EP3530118A1 (en) 2018-02-26 2019-08-28 Basf Se Fungicidal mixtures
EP3530116A1 (en) 2018-02-27 2019-08-28 Basf Se Fungicidal mixtures comprising xemium
JP7444780B2 (en) 2018-02-28 2024-03-06 ビーエーエスエフ ソシエタス・ヨーロピア Use of N-functionalized alkoxypyrazole compounds as nitrification inhibitors
IL276312B2 (en) 2018-02-28 2023-09-01 Basf Se Use of alkoxypyrazoles as nitrification inhibitors
WO2019166252A1 (en) 2018-02-28 2019-09-06 Basf Se Fungicidal mixtures comprising fenpropidin
US11498885B2 (en) 2018-02-28 2022-11-15 Basf Se Use of pyrazole propargyl ethers as nitrification inhibitors
UA126830C2 (en) 2018-03-01 2023-02-08 Басф Агро Б.В. Fungicidal compositions of mefentrifluconazole
EP3533331A1 (en) 2018-03-02 2019-09-04 Basf Se Fungicidal mixtures comprising pydiflumetofen
EP3533333A1 (en) 2018-03-02 2019-09-04 Basf Se Fungicidal mixtures comprising pydiflumetofen
EP3536150A1 (en) 2018-03-06 2019-09-11 Basf Se Fungicidal mixtures comprising fluxapyroxad
WO2019175712A1 (en) 2018-03-14 2019-09-19 Basf Corporation New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways
WO2019175713A1 (en) 2018-03-14 2019-09-19 Basf Corporation New catechol molecules and their use as inhibitors to p450 related metabolic pathways
JP7433244B2 (en) 2018-05-15 2024-02-19 ビーエーエスエフ ソシエタス・ヨーロピア Mixtures containing benzpyrimoxane and oxazosulfil and methods of use and application thereof
WO2019219464A1 (en) 2018-05-15 2019-11-21 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019224092A1 (en) 2018-05-22 2019-11-28 Basf Se Pesticidally active c15-derivatives of ginkgolides
WO2020002472A1 (en) 2018-06-28 2020-01-02 Basf Se Use of alkynylthiophenes as nitrification inhibitors
EP3826982B1 (en) 2018-07-23 2023-11-01 Basf Se Use of a substituted thiazolidine compound as nitrification inhibitor
WO2020020777A1 (en) 2018-07-23 2020-01-30 Basf Se Use of substituted 2-thiazolines as nitrification inhibitors
AR115984A1 (en) 2018-08-17 2021-03-17 Pi Industries Ltd 1,2-DITIOLONE COMPOUNDS AND THEIR USES
EP3613736A1 (en) 2018-08-22 2020-02-26 Basf Se Substituted glutarimide derivatives
CA3112042A1 (en) 2018-09-28 2020-04-02 Basf Se Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof
EP3628157A1 (en) 2018-09-28 2020-04-01 Basf Se Method of controlling insecticide resistant insects and virus transmission to plants
EP3628158A1 (en) 2018-09-28 2020-04-01 Basf Se Pesticidal mixture comprising a mesoionic compound and a biopesticide
EP3628156A1 (en) 2018-09-28 2020-04-01 Basf Se Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants
EP3643705A1 (en) 2018-10-24 2020-04-29 Basf Se Pesticidal compounds
WO2020095161A1 (en) 2018-11-05 2020-05-14 Pi Industries Ltd. Nitrone compounds and use thereof
EP3670501A1 (en) 2018-12-17 2020-06-24 Basf Se Substituted [1,2,4]triazole compounds as fungicides
EP3696177A1 (en) 2019-02-12 2020-08-19 Basf Se Heterocyclic compounds for the control of invertebrate pests
US12342821B2 (en) 2019-02-20 2025-07-01 Basf Se Pesticidal mixtures comprising a pyrazole compound
EP3730489A1 (en) 2019-04-25 2020-10-28 Basf Se Heteroaryl compounds as agrochemical fungicides
EP3769623A1 (en) 2019-07-22 2021-01-27 Basf Se Mesoionic imidazolium compounds and derivatives for combating animal pests
BR112021019416A2 (en) 2019-05-29 2021-12-07 Basf Se Compounds, composition, methods of protecting crops and combating, controlling, preventing or protecting against infestations, non-therapeutic method of treating infested animals, seed and use
WO2020244968A1 (en) 2019-06-06 2020-12-10 Basf Se Fungicidal n-(pyrid-3-yl)carboxamides
WO2020244970A1 (en) 2019-06-06 2020-12-10 Basf Se New carbocyclic pyridine carboxamides
WO2020244969A1 (en) 2019-06-06 2020-12-10 Basf Se Pyridine derivatives and their use as fungicides
EP3766879A1 (en) 2019-07-19 2021-01-20 Basf Se Pesticidal pyrazole derivatives
WO2021063736A1 (en) 2019-10-02 2021-04-08 Basf Se Bicyclic pyridine derivatives
WO2021063735A1 (en) 2019-10-02 2021-04-08 Basf Se New bicyclic pyridine derivatives
WO2021130143A1 (en) 2019-12-23 2021-07-01 Basf Se Enzyme enhanced root uptake of agrochemical active compound
WO2021170463A1 (en) 2020-02-28 2021-09-02 BASF Agro B.V. Methods and uses of a mixture comprising alpha-cypermethrin and dinotefuran for controlling invertebrate pests in turf
EP4114185A1 (en) 2020-03-04 2023-01-11 Basf Se Use of substituted 1,2,4-oxadiazoles for combating phytopathogenic fungi
BR112022020612A2 (en) 2020-04-14 2022-11-29 Basf Se FUNGICIDAL MIXTURE, AGROCHEMICAL COMPOSITION, NON-THERAPEUTIC USE OF THE MIXTURE AND METHOD TO CONTROL HARMFUL PHYTOPATHOGENIC FUNGI
EP3903584A1 (en) 2020-04-28 2021-11-03 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iv
EP3903582A1 (en) 2020-04-28 2021-11-03 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ii
EP3903581A1 (en) 2020-04-28 2021-11-03 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors i
BR112022021631A2 (en) 2020-04-28 2022-12-06 Basf Se COMPOUNDS, COMPOSITION, METHODS TO COMBAT OR CONTROL INVERTEBRATE PEST, TO PROTECT GROWING PLANTS AND TO TREAT OR PROTECT AN ANIMAL, SEED AND USE OF A COMPOUND
EP3903583A1 (en) 2020-04-28 2021-11-03 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iii
EP3909950A1 (en) 2020-05-13 2021-11-17 Basf Se Heterocyclic compounds for the control of invertebrate pests
EP3945089A1 (en) 2020-07-31 2022-02-02 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors v
WO2021249800A1 (en) 2020-06-10 2021-12-16 Basf Se Substituted [1,2,4]triazole compounds as fungicides
EP3960727A1 (en) 2020-08-28 2022-03-02 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors vi
EP3939961A1 (en) 2020-07-16 2022-01-19 Basf Se Strobilurin type compounds and their use for combating phytopathogenic fungi
WO2022017836A1 (en) 2020-07-20 2022-01-27 BASF Agro B.V. Fungicidal compositions comprising (r)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1- (1,2,4-triazol-1-yl)propan-2-ol
EP3970494A1 (en) 2020-09-21 2022-03-23 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors viii
TW202229241A (en) 2020-09-26 2022-08-01 印度商皮埃企業有限公司 Nematocidal compounds and use thereof
US20230397607A1 (en) 2020-10-27 2023-12-14 BASF Agro B.V. Compositions comprising mefentrifluconazole
WO2022090069A1 (en) 2020-11-02 2022-05-05 Basf Se Compositions comprising mefenpyr-diethyl
WO2022090071A1 (en) 2020-11-02 2022-05-05 Basf Se Use of mefenpyr-diethyl for controlling phytopathogenic fungi
WO2022106304A1 (en) 2020-11-23 2022-05-27 BASF Agro B.V. Compositions comprising mefentrifluconazole
EP4018830A1 (en) 2020-12-23 2022-06-29 Basf Se Pesticidal mixtures
CA3206495A1 (en) 2021-02-02 2022-08-11 Alexander Wissemeier Synergistic action of dcd and alkoxypyrazoles as nitrification inhibitors
EP4043444A1 (en) 2021-02-11 2022-08-17 Basf Se Substituted isoxazoline derivatives
BR112023023592A2 (en) 2021-05-11 2024-03-12 Basf Se FUNGICIDAL MIXTURE, AGROCHEMICAL COMPOSITION, USE OF THE MIXTURE AND METHOD TO CONTROL HARMFUL PHYTOPATHOGENIC FUNGI
CN117355519A (en) 2021-05-18 2024-01-05 巴斯夫欧洲公司 Novel substituted pyridines as fungicides
BR112023024017A2 (en) 2021-05-18 2024-02-06 Basf Se COMPOUNDS, COMPOSITION, METHOD TO COMBAT PHYTOPATHOGENIC AND SEED FUNGI
CA3219311A1 (en) 2021-05-18 2022-11-24 Basf Se New substituted quinolines as fungicides
BR112023024012A2 (en) 2021-05-21 2024-02-06 Basf Se USE OF ETHYNYLPYRIDINE COMPOUND, COMPOSITION FOR USE IN NITRIFICATION REDUCTION, AGROCHEMICAL MIXTURE AND METHODS OF NITRIFICATION REDUCTION AND FERTILIZER TREATMENT OR COMPOSITION
BR112023024208A2 (en) 2021-05-21 2024-01-30 Basf Se USE OF A COMPOUND, COMPOSITION, AGROCHEMICAL MIXTURE AND METHODS TO REDUCE NITRIFICATION AND TO TREAT A FERTILIZER
EP4094579A1 (en) 2021-05-28 2022-11-30 Basf Se Pesticidal mixtures comprising metyltetraprole
EP4358725A1 (en) 2021-06-21 2024-05-01 Basf Se Metal-organic frameworks with pyrazole-based building blocks
EP4119547A1 (en) 2021-07-12 2023-01-18 Basf Se Triazole compounds for the control of invertebrate pests
EP4380926A1 (en) 2021-08-02 2024-06-12 Basf Se (3-quinolyl)-quinazoline
CA3227665A1 (en) 2021-08-02 2023-02-09 Wassilios Grammenos (3-pirydyl)-quinazoline
EP4140986A1 (en) 2021-08-23 2023-03-01 Basf Se Pyrazine compounds for the control of invertebrate pests
EP4140995A1 (en) 2021-08-27 2023-03-01 Basf Se Pyrazine compounds for the control of invertebrate pests
EP4151631A1 (en) 2021-09-20 2023-03-22 Basf Se Heterocyclic compounds for the control of invertebrate pests
WO2023072671A1 (en) 2021-10-28 2023-05-04 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ix
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EP4455137A1 (en) 2023-04-24 2024-10-30 Basf Se Pyrimidine compounds for the control of invertebrate pests
WO2024223034A1 (en) 2023-04-26 2024-10-31 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors xvi
EP4467535A1 (en) 2023-05-25 2024-11-27 Basf Se Lactam pesticidal compounds
EP4488273A1 (en) 2023-07-06 2025-01-08 Basf Se Triazole compounds for the control of invertebrate pests
EP4488270A1 (en) 2023-07-06 2025-01-08 Basf Se Triazole compounds for the control of invertebrate pests
EP4488269A1 (en) 2023-07-06 2025-01-08 Basf Se Triazole compounds for the control of invertebrate pests
EP4574819A1 (en) 2023-12-22 2025-06-25 Basf Se Diazinone compounds for the control of invertebrate pests

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3545319A1 (en) * 1985-12-20 1987-06-25 Basf Ag ACRYLIC ACID ESTERS AND FUNGICIDES THAT CONTAIN THESE COMPOUNDS

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