CN1580041A - Unsaturated oximino ether compound with fungicidal, insecticidal activity - Google Patents
Unsaturated oximino ether compound with fungicidal, insecticidal activity Download PDFInfo
- Publication number
- CN1580041A CN1580041A CN 03133668 CN03133668A CN1580041A CN 1580041 A CN1580041 A CN 1580041A CN 03133668 CN03133668 CN 03133668 CN 03133668 A CN03133668 A CN 03133668A CN 1580041 A CN1580041 A CN 1580041A
- Authority
- CN
- China
- Prior art keywords
- compound
- fungicidal
- isomer
- carbon
- insect
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 Unsaturated oximino ether compound Chemical class 0.000 title claims abstract description 9
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 9
- 230000000855 fungicidal effect Effects 0.000 title claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 230000001954 sterilising effect Effects 0.000 claims abstract description 3
- 238000004659 sterilization and disinfection Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 9
- 229940125782 compound 2 Drugs 0.000 description 9
- 229940126214 compound 3 Drugs 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 4
- 241000272639 Brachycaudus mimeuri Species 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 230000003449 preventive effect Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 241000409991 Mythimna separata Species 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000012136 culture method Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000001418 larval effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical class ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000009246 food effect Effects 0.000 description 1
- 235000021471 food effect Nutrition 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BSDQITJYKQHXQR-UHFFFAOYSA-N methyl prop-2-eneperoxoate Chemical compound COOC(=O)C=C BSDQITJYKQHXQR-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Compound | ????R 1 | ????R 2 | Configuration | ????mp(℃) |
????1 | ????Cl | ????H | ????E/E | ????89-90 |
????2 | ????Cl | ????H | ????E/Z | Oily matter |
????3 | ????Cl | ????H | ????Z/E | ????176-178 |
????4 | ????Cl | ????H | ????Z/Z | ????134-136 |
Reagent agent | Treatment dosage ug/ml | Disease refers to | Preventive effect (%) |
Compound 1 (E/E) | ??????200 | ?????0 | ???100 |
??????50 | ?????0 | ???100 | |
??????12.5 | ?????1.85 | ???98.15 | |
Compound 2 (E/Z) | ??????200 | ?????0 | ???100 |
??????50 | ?????0 | ???100 | |
??????12.5 | ?????3.70 | ???96.30 | |
Compound 3 (Z/E) | ??????200 | ?????100 | ???0 |
??????50 | ?????100 | ???0 | |
??????12.5 | ?????100 | ???0 | |
Compound 4 (Z/Z) | ??????200 | ?????81.48 | ???18.52 |
??????50 | ?????100 | ???0 | |
??????12.5 | ?????100 | ???0 | |
Control compound * | ??????200 | ?????0 | ???100 |
??????50 | ?????1.85 | ???98.15 | |
??????12.5 | ?????16.26 | ???83.74 |
Reagent agent | Treatment dosage ug/ml | Wheat powdery mildew | |
Disease refers to | Preventive effect (%) | ||
Compound 1 (E/E) | ????200 | ????0 | ????100 |
????50 | ????2.54 | ????96.77 | |
????12.5 | ????8.79 | ????88.83 | |
Compound 2 (E/Z) | ????200 | ????0 | ????100 |
????50 | ????3.17 | ????95.97 | |
????12.5 | ????9.82 | ????87.52 | |
Compound 3 (Z/E) | ????200 | ????66.54 | ????15.43 |
????50 | ????100 | ????0 | |
????12.5 | ????100 | ????0 | |
Compound 4 (Z/Z) | ????200 | ????69.78 | ????11.31 |
????50 | ????100 | ????0 | |
????12.5 | ????100 | ????0 | |
Control compound | ????200 | ????0 | ????100 |
????50 | ????3.12 | ????96.03 | |
????12.5 | ????17.69 | ????77.52 |
Reagent agent | Dosage (mg/L) | Handle the food rate (%) of getting in back 3 days | Handle back 3 days larval mortalities (%) |
Compound 1 (E/E) | ????500 | ????0.9 | ?????100 |
????250 | ????2.3 | ?????100 | |
????100 | ????7.5 | ?????60 | |
????50 | ????23 | ?????40 | |
Compound 2 (E/Z) | ????500 | ????75 | ?????0 |
????250 | ????100 | ?????0 | |
Compound 3 (Z/E) | ????250 | ????100 | ?????0 |
????100 | ????100 | ?????0 | |
Compound 4 (Z/Z) | ????250 | ????100 | ?????0 |
????100 | ????100 | ?????0 | |
Blank | ????- | ????100 | ?????0 |
Reagent agent | Dosage (mg/L) | Handle back 2 days black peach aphid mortality ratio (%) |
Compound 1 (E/E) | ????250 | ?????100 |
????100 | ?????99 | |
Compound 2 (E/Z) | ????250 | ?????100 |
????100 | ?????90 | |
Compound 3 (Z/E) | ????250 | ?????0 |
????100 | ?????0 | |
Compound 4 (Z/Z) | ????250 | ?????50 |
????100 | ?????0 | |
Blank | ????-- | ?????0 |
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB03133668XA CN1293046C (en) | 2003-08-12 | 2003-08-12 | Unsaturated oximino ether compound with fungicidal, insecticidal activity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB03133668XA CN1293046C (en) | 2003-08-12 | 2003-08-12 | Unsaturated oximino ether compound with fungicidal, insecticidal activity |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1580041A true CN1580041A (en) | 2005-02-16 |
CN1293046C CN1293046C (en) | 2007-01-03 |
Family
ID=34579050
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB03133668XA Expired - Lifetime CN1293046C (en) | 2003-08-12 | 2003-08-12 | Unsaturated oximino ether compound with fungicidal, insecticidal activity |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1293046C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017024971A1 (en) * | 2015-08-12 | 2017-02-16 | 沈阳中化农药化工研发有限公司 | Unsaturated oximino ether compound and use thereof |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0936213B1 (en) * | 1998-02-10 | 2003-03-26 | Dow AgroSciences LLC | Unsaturated oxime ethers and their use as fungicides and insecticides |
-
2003
- 2003-08-12 CN CNB03133668XA patent/CN1293046C/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017024971A1 (en) * | 2015-08-12 | 2017-02-16 | 沈阳中化农药化工研发有限公司 | Unsaturated oximino ether compound and use thereof |
Also Published As
Publication number | Publication date |
---|---|
CN1293046C (en) | 2007-01-03 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: SINOCHEM CORPORATION; SHENYANG CHEMICAL ENGINEERI Free format text: FORMER OWNER: SHENYANG CHEMICAL ENGINEERING INST. Effective date: 20080711 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20080711 Address after: F6-F12, middle block, Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee after: Shenyang Research Institute of Chemical Industry Patentee after: Sinochem Corp. Address before: No 8, Shen Liaodong Road, Tiexi District, Liaoning, Shenyang: 110021 Patentee before: Shenyang Research Institute of Chemical Industry |
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ASS | Succession or assignment of patent right |
Owner name: CHINA CHEMISTRY CO., LTD. Free format text: FORMER OWNER: SINOCHEM CORPORATION Effective date: 20091120 |
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C41 | Transfer of patent application or patent right or utility model | ||
C56 | Change in the name or address of the patentee | ||
CP03 | Change of name, title or address |
Address after: F6-F12, middle block, Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee after: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Patentee after: Sinochem Corp. Address before: F6-F12, middle block, Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee before: Shenyang Research Institute of Chemical Industry Patentee before: Sinochem Corp. |
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TR01 | Transfer of patent right |
Effective date of registration: 20091120 Address after: 28, Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee after: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Patentee after: SINOCHEM Corp. Address before: F6-F12, middle block, Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee before: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Patentee before: Sinochem Corp. |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160122 Address after: 110021 Liaodong Road, Tiexi District, Liaoning, No. 8-1, No. Patentee after: SHENYANG SINOCHEM AGROCHEMICALS R&D Co.,Ltd. Address before: 28, Fuxing Avenue, Xicheng District, Beijing Patentee before: SINOCHEM Corp. Patentee before: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. |
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CX01 | Expiry of patent term |
Granted publication date: 20070103 |
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CX01 | Expiry of patent term |