CN1923819A - compound containing aromatic ether and ditriazole and use thereof - Google Patents
compound containing aromatic ether and ditriazole and use thereof Download PDFInfo
- Publication number
- CN1923819A CN1923819A CN200610140836.7A CN200610140836A CN1923819A CN 1923819 A CN1923819 A CN 1923819A CN 200610140836 A CN200610140836 A CN 200610140836A CN 1923819 A CN1923819 A CN 1923819A
- Authority
- CN
- China
- Prior art keywords
- acid
- aryl oxide
- triazole compounds
- agroforestry
- fungal disease
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 14
- 150000008378 aryl ethers Chemical class 0.000 title abstract 2
- -1 C1-4 Chemical group 0.000 claims abstract description 53
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 241000233866 Fungi Species 0.000 claims abstract description 10
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 229910052736 halogen Chemical group 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 208000031888 Mycoses Diseases 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000011833 salt mixture Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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- 239000001530 fumaric acid Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 150000003852 triazoles Chemical class 0.000 description 12
- 239000005760 Difenoconazole Substances 0.000 description 9
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003899 bactericide agent Substances 0.000 description 7
- 230000000855 fungicidal effect Effects 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 5
- 239000005839 Tebuconazole Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
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- 230000004071 biological effect Effects 0.000 description 3
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- 239000000645 desinfectant Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000452 restraining effect Effects 0.000 description 3
- KVKFSLYUIUDSOI-UHFFFAOYSA-N 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C1=NC=NN1CC(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)(O)CN1C=NC=N1 KVKFSLYUIUDSOI-UHFFFAOYSA-N 0.000 description 2
- 241000193738 Bacillus anthracis Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000233629 Phytophthora parasitica Species 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
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- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Routine number | R 1 | R 2 | R 3 | R 4 | R 5 | R 6 |
1 | H | H | H | H | H | H |
2 | H | H | Cl | H | H | 6-Cl |
3 | Cl | H | Cl | H | H | H |
4 | H | H | Cl | H | H | H |
5 | H | Cl | H | 5-Cl | H | H |
6 | H | Cl | H | 6-Cl | H | H |
7 | H | Cl | H | H | H | H |
8 | H | Br | H | H | H | H |
9 | H | H | CH 3 | H | H | H |
10 | CH 3 | H | CH 3 | H | H | H |
11 | F | H | H | H | H | H |
12 | H | F | H | H | H | H |
13 | H | H | F | H | H | H |
14 | Br | H | H | H | H | H |
15 | H | H | Br | H | H | H |
16 | C 2H 5 | H | H | H | H | H |
17 | H | H | C 4H 9-t | H | H | H |
18 | OCH 3 | H | H | H | H | H |
19 | H | H | NO 2 | H | H | H |
20 | CF 3 | H | H | H | H | H |
21 | H | H | CF 3 | H | H | H |
22 | Br | H | Br | H | H | H |
23 | Br | H | Cl | H | H | H |
24 | Cl | H | Br | H | H | H |
25 | H | Cl | Cl | 6-Cl | H | H |
26 | CH 3 | H | Cl | H | H | H |
27 | NO 2 | H | CF 3 | H | H | H |
28 | NO 2 | H | NO 2 | 6-CF 3 | H | H |
29 | Cl | Cl | H | H | H | H |
30 | CH 3 | H | H | H | 2-CH 3 | H |
31 | H | H | Cl | H | 2-CH 3 | H |
32 | Cl | H | CF 3 | H | H | H |
33 | Cl | H | CF 3 | H | H | 6-Cl |
34 | H | H | Cl | H | 2-CH 3 | H |
35 | H | F | H | H | 2-CH 3 | H |
36 | CH 3 | H | H | H | 2-CH 3 | H |
37 | H | H | OCH 3 | H | 2-CH 3 | H |
38 | H | H | F | H | 2-CH 3 | H |
39 | OCH 3 | H | H | H | 2-Cl | H |
40 | H | H | F | H | 2-OCH 3 | H |
41 | H | H | Cl | H | 3-Cl | H |
42 | H | H | Cl | H | 2-C 2H 5 | H |
43 | H | H | H | H | 2-CH 3 | H |
44 | H | H | H | H | 2-Cl | H |
45 | H | H | H | H | 3-CH 3 | H |
46 | H | H | H | H | 2-CH 3 | 5-CH 3 |
47 | H | H | H | H | 2-C 2H 5 | H |
48 | H | H | CF 3 | H | 3-Cl | H |
49 | H | H | F | H | H | 6-Cl |
50 | H | H | F | H | H | 6-F |
The fungi title | Fungicidal activity (5 μ g/mL), % | ||
Difenoconazole | Tebuconazole | Compound 2 | |
Sugar beet leaf spot bacteria | 100.0 | 100.0 | 100.0 |
Fusarium moniliforme | 100.0 | 100.0 | 100.0 |
Cucumber fusarium axysporum | 80.9 | 99.0 | 80.9 |
Peanut Cercospora bacteria | 100.0 | 100.0 | 100.0 |
Asparagus stem wilt bacteria | 100.0 | 100.0 | 100.0 |
Tomato early blight bacterium | 84.2 | 84.2 | 84.2 |
Fusarium graminearum | 100.0 | 100.0 | 100.0 |
The ring rot of apple bacterium | 94.5 | 91.0 | 91.0 |
The rice green smut bacterium | 100.0 | 100.0 | 100.0 |
Dosporium cucumerinumand its | 94.5 | 91.0 | 91.0 |
Botrytis cinerea pers | 99.0 | 99.0 | 99.0 |
Sclerotinia sclerotiorum | 99.0 | 99.0 | 99.0 |
Apple zonate spot bacterium | 99.0 | 99.0 | 99.0 |
Valsa mali | 99.0 | 99.0 | 99.0 |
Glorosprium musarum Cookeet Mass | 100.0 | 100.0 | 100.0 |
The brown edge germ of banana | 86.5 | 86.5 | 83.8 |
Watermelon anthrax bacteria | 99.0 | 88.5 | 99.0 |
Apple anthrax bacteria | 100.0 | 99.0 | 100.0 |
Cucumber anthracnose | 100.0 | 100.0 | 100.0 |
The pears alternaria | 99.0 | 99.0 | 99.0 |
The root rotof flax bacterium | 99.0 | 99.0 | 99.0 |
The miliary damping-off germ | 99.0 | 95.0 | 99.0 |
Cereal silk nuclear germ | 99.0 | 99.0 | 99.0 |
Cotton-wilt fusarium | 76.2 | 90.5 | 80.9 |
Verticillium dahliae | 92.3 | 92.3 | 92.3 |
Southern corn leaf blight | 99.0 | 99.0 | 99.0 |
The fungi title | Fungicidal activity (1 μ g/mL), % | ||
Difenoconazole | Tebuconazole | Compound 2 | |
Fusarium graminearum | 73.9 | 86.9 | 82.6 |
Tomato early blight bacterium | 95 | 65.5 | 58.6 |
Cucumber fusarium axysporum | 53.1 | 65.6 | 62.5 |
The ring rot of apple bacterium | 69.7 | 68.2 | 90.3 |
Sclerotinia sclerotiorum | 56.7 | 91 | 88.1 |
The miliary damping-off germ | 94.7 | 94.7 | 94.7 |
Cereal silk nuclear germ | 93 | 93 | 93 |
Claims (10)
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