ZA200508026B - Fungicides containing methoxy acrylic acid methyl ester compound - Google Patents
Fungicides containing methoxy acrylic acid methyl ester compound Download PDFInfo
- 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
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- powdery mildew
- composition
- mildew
- cucumber
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title description 40
- -1 methoxy acrylic acid methyl ester compound Chemical class 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 92
- 239000000203 mixture Substances 0.000 claims description 47
- 241000221785 Erysiphales Species 0.000 claims description 35
- 230000000855 fungicidal effect Effects 0.000 claims description 34
- 240000008067 Cucumis sativus Species 0.000 claims description 25
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 17
- 239000003513 alkali Substances 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 235000009754 Vitis X bourquina Nutrition 0.000 claims description 11
- 235000012333 Vitis X labruscana Nutrition 0.000 claims description 11
- 235000014787 Vitis vinifera Nutrition 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 241000196324 Embryophyta Species 0.000 claims description 7
- 239000000839 emulsion Substances 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 241000219112 Cucumis Species 0.000 claims description 3
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 241000235349 Ascomycota Species 0.000 claims description 2
- 241000233654 Oomycetes Species 0.000 claims description 2
- 235000013399 edible fruits Nutrition 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 240000006365 Vitis vinifera Species 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- DIDDVZFHORVZMG-UHFFFAOYSA-N methyl 2-methylprop-2-eneperoxoate Chemical group COOC(=O)C(C)=C DIDDVZFHORVZMG-UHFFFAOYSA-N 0.000 claims 1
- 239000005648 plant growth regulator Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 41
- 241000209140 Triticum Species 0.000 description 17
- 235000021307 Triticum Nutrition 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 230000002265 prevention Effects 0.000 description 14
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 241000219095 Vitis Species 0.000 description 10
- 238000005507 spraying Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000007530 organic bases Chemical class 0.000 description 9
- 241000233679 Peronosporaceae Species 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
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- 239000003921 oil Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 5
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- 235000009854 Cucurbita moschata Nutrition 0.000 description 5
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- 239000002270 dispersing agent Substances 0.000 description 5
- BTTXESIFAHCXMK-UHFFFAOYSA-N methyl 2-methoxyprop-2-enoate Chemical compound COC(=C)C(=O)OC BTTXESIFAHCXMK-UHFFFAOYSA-N 0.000 description 5
- 235000015136 pumpkin Nutrition 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000005818 Picoxystrobin Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 229940125904 compound 1 Drugs 0.000 description 3
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- 239000000428 dust Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- 241001163841 Albugo ipomoeae-panduratae Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005946 Cypermethrin Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
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- 239000005794 Hymexazol Substances 0.000 description 2
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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- 230000000052 comparative effect Effects 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229960005424 cypermethrin Drugs 0.000 description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
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- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
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- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters 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
- C07C69/73—Esters 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
- C07C69/734—Ethers
- C07C69/736—Ethers 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION 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
- A01N37/00—Biocides, 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
- A01N37/36—Biocides, 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation 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
- C07C67/343—Preparation 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
Landscapes
- 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
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 .
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.
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.
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.
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)
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
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Family Cites Families (1)
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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2003
- 2003-03-25 CN CN 03120882 patent/CN1201657C/en not_active Expired - Lifetime
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2004
- 2004-03-19 WO PCT/CN2004/000226 patent/WO2004084632A1/en active Application Filing
- 2004-03-19 BR BRPI0409037-3A patent/BRPI0409037A/en not_active Application Discontinuation
- 2004-03-19 TR TR2005/03847T patent/TR200503847T1/en unknown
- 2004-03-19 AU AU2004224838A patent/AU2004224838A1/en not_active Abandoned
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2005
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TR200503847T1 (en) | 2006-04-21 |
AU2004224838A1 (en) | 2004-10-07 |
CN1201657C (en) | 2005-05-18 |
WO2004084632A1 (en) | 2004-10-07 |
BRPI0409037A (en) | 2006-03-28 |
CN1456054A (en) | 2003-11-19 |
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