DK173341B1 - 2-substituerede methyl-propenoatforbindelser, en fremgangsmåde til deres fremstilling, samt deres anvendelse som fungicider - Google Patents

2-substituerede methyl-propenoatforbindelser, en fremgangsmåde til deres fremstilling, samt deres anvendelse som fungicider Download PDF

Info

Publication number: DK173341B1
Authority: DK; Denmark
Prior art keywords: compounds; plant; methyl; compound; general formula
Prior art date: 1985-08-22

Application number

DK198603945A

Other languages

Danish (da)

English (en)

Other versions

DK394586A (da

DK394586D0 (da

Inventor

John Martin Clough

Christopher Richard Ay Godfrey

Original Assignee

Zeneca Ltd

Priority date (The priority date 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 date listed.)

1985-08-22

Filing date

1986-08-19

Publication date

2000-07-31

1986-08-19 Application filed by Zeneca Ltd filed Critical Zeneca Ltd

1986-08-19 Publication of DK394586D0 publication Critical patent/DK394586D0/da

1987-02-23 Publication of DK394586A publication Critical patent/DK394586A/da

2000-07-31 Application granted granted Critical

2000-07-31 Publication of DK173341B1 publication Critical patent/DK173341B1/da

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 15
239000000417 fungicide Substances 0.000 title claims description 9
230000008569 process Effects 0.000 title claims description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 105
239000000203 mixture Substances 0.000 claims description 39
239000003795 chemical substances by application Substances 0.000 claims description 28
239000004480 active ingredient Substances 0.000 claims description 17
230000008635 plant growth Effects 0.000 claims description 17
230000001105 regulatory effect Effects 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
230000000855 fungicidal effect Effects 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 4
239000005648 plant growth regulator Substances 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 4
241000233866 Fungi Species 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000006413 ring segment Chemical group 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
230000001276 controlling effect Effects 0.000 claims description 2
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 2
229910000343 potassium bisulfate Inorganic materials 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
229940125773 compound 10 Drugs 0.000 claims 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
241000196324 Embryophyta Species 0.000 description 47
-1 C3 ^ Chemical group 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
239000003921 oil Substances 0.000 description 24
235000019198 oils Nutrition 0.000 description 24
235000013339 cereals Nutrition 0.000 description 23
239000000243 solution Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
201000010099 disease Diseases 0.000 description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
238000011282 treatment Methods 0.000 description 16
239000002904 solvent Substances 0.000 description 14
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 13
230000000694 effects Effects 0.000 description 13
239000002689 soil Substances 0.000 description 13
239000000126 substance Substances 0.000 description 13
239000004615 ingredient Substances 0.000 description 11
239000007788 liquid Substances 0.000 description 11
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
240000007594 Oryza sativa Species 0.000 description 10
235000007164 Oryza sativa Nutrition 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
229940126543 compound 14 Drugs 0.000 description 10
230000012010 growth Effects 0.000 description 10
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 10
235000009566 rice Nutrition 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
240000005979 Hordeum vulgare Species 0.000 description 8
235000007340 Hordeum vulgare Nutrition 0.000 description 8
241000209140 Triticum Species 0.000 description 8
235000021307 Triticum Nutrition 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000005507 spraying Methods 0.000 description 8
229930182692 Strobilurin Natural products 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
239000003480 eluent Substances 0.000 description 7
238000000338 in vitro Methods 0.000 description 7
229910052573 porcelain Inorganic materials 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
JSCQSBGXKRTPHZ-WMSPMLHYSA-N Strobilurin A Natural products COC=C(/C(=C/C=C/c1ccccc1)/C)C(=O)OC JSCQSBGXKRTPHZ-WMSPMLHYSA-N 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
JSCQSBGXKRTPHZ-SYKZHUKTSA-N mucidin Chemical compound CO\C=C(\C(=O)OC)/C(/C)=C\C=C\C1=CC=CC=C1 JSCQSBGXKRTPHZ-SYKZHUKTSA-N 0.000 description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
241000221785 Erysiphales Species 0.000 description 5
244000068988 Glycine max Species 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
241000220225 Malus Species 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000004696 coordination complex Chemical class 0.000 description 5
239000003337 fertilizer Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000007921 spray Substances 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
241000233679 Peronosporaceae Species 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000012267 brine Substances 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
230000002089 crippling effect Effects 0.000 description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
230000005520 electrodynamics Effects 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000945 filler Substances 0.000 description 4
239000012530 fluid Substances 0.000 description 4
230000002538 fungal effect Effects 0.000 description 4
238000003306 harvesting Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
NAVKCQMYRLUWFQ-UHFFFAOYSA-N methyl 3-(3-phenylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=CC(C=2C=CC=CC=2)=C1 NAVKCQMYRLUWFQ-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
241000894007 species Species 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
244000105624 Arachis hypogaea Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
244000025254 Cannabis sativa Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
244000061456 Solanum tuberosum Species 0.000 description 3
235000002595 Solanum tuberosum Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
230000009102 absorption Effects 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000009826 distribution Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
238000000227 grinding Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
238000009413 insulation Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
235000020232 peanut Nutrition 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
235000013311 vegetables Nutrition 0.000 description 3
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 3
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 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RTFPTPXBTIUISM-UHFFFAOYSA-N 1-(bromomethyl)-3-phenylbenzene Chemical compound BrCC1=CC=CC(C=2C=CC=CC=2)=C1 RTFPTPXBTIUISM-UHFFFAOYSA-N 0.000 description 2
NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
229940093475 2-ethoxyethanol Drugs 0.000 description 2
GNOMLLKHNCKJRX-UHFFFAOYSA-N 2-phenylethylalumane Chemical compound C1(=CC=CC=C1)CC[AlH2] GNOMLLKHNCKJRX-UHFFFAOYSA-N 0.000 description 2
VFUQDUGKYYDRMT-UHFFFAOYSA-N 3-methoxyprop-2-enoic acid Chemical group COC=CC(O)=O VFUQDUGKYYDRMT-UHFFFAOYSA-N 0.000 description 2
MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 2
241001480061 Blumeria graminis Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000371644 Curvularia ravenelii Species 0.000 description 2
240000009088 Fragaria x ananassa Species 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
241001507673 Penicillium digitatum Species 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
241001123583 Puccinia striiformis Species 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 0.000 description 2
206010039509 Scab Diseases 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
241000228452 Venturia inaequalis Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
239000000654 additive Substances 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical class [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
235000021016 apples Nutrition 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
239000012043 crude product Substances 0.000 description 2
YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
235000021186 dishes Nutrition 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
LVPKHWZGTOOBOT-UHFFFAOYSA-N methyl 2-(3-phenylphenoxy)acetate Chemical compound COC(=O)COC1=CC=CC(C=2C=CC=CC=2)=C1 LVPKHWZGTOOBOT-UHFFFAOYSA-N 0.000 description 2
HMRYYDCVPHSQLQ-UHFFFAOYSA-N methyl 2-(3-phenylphenyl)sulfanylacetate Chemical compound C1(=CC=CC=C1)C=1C=C(SCC(=O)OC)C=CC1 HMRYYDCVPHSQLQ-UHFFFAOYSA-N 0.000 description 2
GVTOZLWETRQOAA-UHFFFAOYSA-N methyl 2-(n-methyl-3-phenylanilino)acetate Chemical compound COC(=O)CN(C)C1=CC=CC(C=2C=CC=CC=2)=C1 GVTOZLWETRQOAA-UHFFFAOYSA-N 0.000 description 2
MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 2
AUHMONDMJSDIGF-UHFFFAOYSA-N methyl 3-hydroxy-2-(3-phenylphenoxy)prop-2-enoate Chemical compound COC(=O)C(=CO)OC1=CC=CC(C=2C=CC=CC=2)=C1 AUHMONDMJSDIGF-UHFFFAOYSA-N 0.000 description 2
QIQCANMEUGRUTA-UHFFFAOYSA-N methyl 3-hydroxy-2-(3-phenylphenyl)sulfanylprop-2-enoate Chemical compound OC=C(C(=O)OC)SC1=CC(=CC=C1)C1=CC=CC=C1 QIQCANMEUGRUTA-UHFFFAOYSA-N 0.000 description 2
RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 description 2
JCCWBLXWOYOGSL-UHFFFAOYSA-N methylsulfanyl prop-2-enoate Chemical group CSOC(=O)C=C JCCWBLXWOYOGSL-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
244000052769 pathogen Species 0.000 description 2
239000003415 peat Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
230000000885 phytotoxic effect Effects 0.000 description 2
244000000003 plant pathogen Species 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000012015 potatoes Nutrition 0.000 description 2
238000004382 potting Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000004904 shortening Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
235000021012 strawberries Nutrition 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 description 1
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
DARPYRSDRJYGIF-PTNGSMBKSA-N (Z)-3-ethoxy-2-naphthalen-2-ylsulfonylprop-2-enenitrile Chemical compound C1=CC=CC2=CC(S(=O)(=O)C(\C#N)=C/OCC)=CC=C21 DARPYRSDRJYGIF-PTNGSMBKSA-N 0.000 description 1
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
RMOGWMIKYWRTKW-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)CC1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UHFFFAOYSA-N 0.000 description 1
SLRVNRROEYCAHO-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,6-dimethyl-2-oxopyridine-3-carboxylic acid Chemical compound O=C1C(C(O)=O)=C(C)C=C(C)N1C1=CC=C(Cl)C=C1 SLRVNRROEYCAHO-UHFFFAOYSA-N 0.000 description 1
VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
OGBSAJWRIPNIER-UHFFFAOYSA-N 2-chloro-6-(furan-2-ylmethoxy)-4-(trichloromethyl)pyridine Chemical compound ClC1=CC(C(Cl)(Cl)Cl)=CC(OCC=2OC=CC=2)=N1 OGBSAJWRIPNIER-UHFFFAOYSA-N 0.000 description 1
OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
RZCJYMOBWVJQGV-UHFFFAOYSA-N 2-naphthyloxyacetic acid Chemical compound C1=CC=CC2=CC(OCC(=O)O)=CC=C21 RZCJYMOBWVJQGV-UHFFFAOYSA-N 0.000 description 1
UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
ZOMKCDYJHAQMCU-UHFFFAOYSA-N 4-butyl-1,2,4-triazole Chemical group CCCCN1C=NN=C1 ZOMKCDYJHAQMCU-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
241000223602 Alternaria alternata Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000017060 Arachis glabrata Nutrition 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
229930192334 Auxin Natural products 0.000 description 1
239000005734 Benalaxyl Substances 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
241000123650 Botrytis cinerea Species 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000006008 Brassica napus var napus Nutrition 0.000 description 1
241000233685 Bremia lactucae Species 0.000 description 1
239000005489 Bromoxynil Substances 0.000 description 1
239000005742 Bupirimate Substances 0.000 description 1
239000005885 Buprofezin Substances 0.000 description 1
AZOXXYBGRGVQRC-GHRIWEEISA-N CO\C=C(C(=O)OC)/CC1=CC=CC(C=2C=CC=CC=2)=C1 Chemical compound CO\C=C(C(=O)OC)/CC1=CC=CC(C=2C=CC=CC=2)=C1 AZOXXYBGRGVQRC-GHRIWEEISA-N 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
206010007134 Candida infections Diseases 0.000 description 1
235000002566 Capsicum Nutrition 0.000 description 1
239000005745 Captan Substances 0.000 description 1
239000005490 Carbetamide Substances 0.000 description 1
239000005746 Carboxin Substances 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
241000530549 Cercospora beticola Species 0.000 description 1
241001065113 Cercosporidium Species 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
239000005944 Chlorpyrifos Substances 0.000 description 1
244000223760 Cinnamomum zeylanicum Species 0.000 description 1
241000407098 Colletotrichum coffeanum Species 0.000 description 1
241000222233 Colletotrichum musae Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000005752 Copper oxychloride Substances 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
241000219122 Cucurbita Species 0.000 description 1
239000005756 Cymoxanil Substances 0.000 description 1
239000005975 Daminozide Substances 0.000 description 1
NOQGZXFMHARMLW-UHFFFAOYSA-N Daminozide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
URDNHJIVMYZFRT-UHFFFAOYSA-N Diclobutrazol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)CC1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-UHFFFAOYSA-N 0.000 description 1
239000005947 Dimethoate Substances 0.000 description 1
239000005765 Dodemorph Substances 0.000 description 1
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
241000510928 Erysiphe necator Species 0.000 description 1
OQOULEWDDRNBSG-UHFFFAOYSA-N Fenapanil Chemical compound C=1C=CC=CC=1C(CCCC)(C#N)CN1C=CN=C1 OQOULEWDDRNBSG-UHFFFAOYSA-N 0.000 description 1
PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
VEVZCONIUDBCDC-UHFFFAOYSA-N Flurprimidol Chemical compound C=1N=CN=CC=1C(O)(C(C)C)C1=CC=C(OC(F)(F)F)C=C1 VEVZCONIUDBCDC-UHFFFAOYSA-N 0.000 description 1
239000005786 Flutolanil Substances 0.000 description 1
239000005787 Flutriafol Substances 0.000 description 1
239000005789 Folpet Substances 0.000 description 1
239000005791 Fuberidazole Substances 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
241000223194 Fusarium culmorum Species 0.000 description 1
229930191978 Gibberellin Natural products 0.000 description 1
HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
239000005562 Glyphosate Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000208818 Helianthus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
PFDCOZXELJAUTR-UHFFFAOYSA-N Inabenfide Chemical compound C=1C(Cl)=CC=C(NC(=O)C=2C=CN=CC=2)C=1C(O)C1=CC=CC=C1 PFDCOZXELJAUTR-UHFFFAOYSA-N 0.000 description 1
FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
238000002768 Kirby-Bauer method Methods 0.000 description 1
240000008415 Lactuca sativa Species 0.000 description 1
235000003228 Lactuca sativa Nutrition 0.000 description 1
239000005574 MCPA Substances 0.000 description 1
241001330975 Magnaporthe oryzae Species 0.000 description 1
BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
239000005802 Mancozeb Substances 0.000 description 1
240000004658 Medicago sativa Species 0.000 description 1
OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 1
239000005807 Metalaxyl Substances 0.000 description 1
240000005561 Musa balbisiana Species 0.000 description 1
235000018290 Musa x paradisiaca Nutrition 0.000 description 1
239000005811 Myclobutanil Substances 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
VJAWBEFMCIINFU-UHFFFAOYSA-N Nitrothal-isopropyl Chemical group CC(C)OC(=O)C1=CC(C(=O)OC(C)C)=CC([N+]([O-])=O)=C1 VJAWBEFMCIINFU-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
240000006460 Panicum notatum Species 0.000 description 1
241000736122 Parastagonospora nodorum Species 0.000 description 1
241000315044 Passalora arachidicola Species 0.000 description 1
239000005813 Penconazole Substances 0.000 description 1
239000005814 Pencycuron Substances 0.000 description 1
241000122123 Penicillium italicum Species 0.000 description 1
241001223281 Peronospora Species 0.000 description 1
244000025272 Persea americana Species 0.000 description 1
235000008673 Persea americana Nutrition 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241000233622 Phytophthora infestans Species 0.000 description 1
241000758706 Piperaceae Species 0.000 description 1
239000005923 Pirimicarb Substances 0.000 description 1
241000317981 Podosphaera fuliginea Species 0.000 description 1
241001337928 Podosphaera leucotricha Species 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000005820 Prochloraz Substances 0.000 description 1
239000005822 Propiconazole Substances 0.000 description 1
239000005823 Propineb Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
241001281802 Pseudoperonospora Species 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241001123559 Puccinia hordei Species 0.000 description 1
241001123569 Puccinia recondita Species 0.000 description 1
241001515786 Rhynchosporium Species 0.000 description 1
241001533598 Septoria Species 0.000 description 1
229910003691 SiBr Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
239000005842 Thiophanate-methyl Substances 0.000 description 1
239000005843 Thiram Substances 0.000 description 1
239000005845 Tolclofos-methyl Substances 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
239000005846 Triadimenol Substances 0.000 description 1
CNFMJLVJDNGPHR-UKTHLTGXSA-N Triapenthenol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1CCCCC1 CNFMJLVJDNGPHR-UKTHLTGXSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
240000000359 Triticum dicoccon Species 0.000 description 1
229920001938 Vegetable gum Polymers 0.000 description 1
241001123669 Verticillium albo-atrum Species 0.000 description 1
235000002096 Vicia faba var. equina Nutrition 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
CVQODEWAPZVVBU-UHFFFAOYSA-N XMC Chemical compound CNC(=O)OC1=CC(C)=CC(C)=C1 CVQODEWAPZVVBU-UHFFFAOYSA-N 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
AMRQXHFXNZFDCH-SECBINFHSA-N [(2r)-1-(ethylamino)-1-oxopropan-2-yl] n-phenylcarbamate Chemical compound CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1 AMRQXHFXNZFDCH-SECBINFHSA-N 0.000 description 1
XVPDKXBMFMQVIM-UHFFFAOYSA-N [F].ClC(Cl)Cl Chemical compound [F].ClC(Cl)Cl XVPDKXBMFMQVIM-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
229940008309 acetone / ethanol Drugs 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000001931 aliphatic group Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
239000011717 all-trans-retinol Substances 0.000 description 1
235000019169 all-trans-retinol Nutrition 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
229920005550 ammonium lignosulfonate Polymers 0.000 description 1
IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002363 auxin Substances 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
238000010296 bead milling Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 0.000 description 1
PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229920005551 calcium lignosulfonate Polymers 0.000 description 1
201000003984 candidiasis Diseases 0.000 description 1
JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
229940117949 captan Drugs 0.000 description 1
229960005286 carbaryl Drugs 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000004891 communication Methods 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-UHFFFAOYSA-N 0.000 description 1
239000004062 cytokinin Substances 0.000 description 1
UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
WEBQKRLKWNIYKK-UHFFFAOYSA-N demeton-S-methyl Chemical compound CCSCCSP(=O)(OC)OC WEBQKRLKWNIYKK-UHFFFAOYSA-N 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
235000019621 digestibility Nutrition 0.000 description 1
FWCBATIDXGJRMF-UHFFFAOYSA-N dikegulac Natural products C12OC(C)(C)OCC2OC2(C(O)=O)C1OC(C)(C)O2 FWCBATIDXGJRMF-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
DPKKZJSKBHGNDF-UHFFFAOYSA-N dimethyl 2-[(3-phenylphenyl)methyl]propanedioate Chemical compound COC(=O)C(C(=O)OC)CC1=CC=CC(C=2C=CC=CC=2)=C1 DPKKZJSKBHGNDF-UHFFFAOYSA-N 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000005489 dwarf bean Nutrition 0.000 description 1
244000013123 dwarf bean Species 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
BBXXLROWFHWFQY-UHFFFAOYSA-N ethirimol Chemical compound CCCCC1=C(C)NC(NCC)=NC1=O BBXXLROWFHWFQY-UHFFFAOYSA-N 0.000 description 1
CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical group CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 1
WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
238000001914 filtration Methods 0.000 description 1
PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
244000000004 fungal plant pathogen Species 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000003448 gibberellin Substances 0.000 description 1
IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
229940097068 glyphosate Drugs 0.000 description 1
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000004404 heteroalkyl group Chemical group 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000003617 indole-3-acetic acid Substances 0.000 description 1
JTEDVYBZBROSJT-UHFFFAOYSA-N indole-3-butyric acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CNC2=C1 JTEDVYBZBROSJT-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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 1
PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
229960001669 kinetin Drugs 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000035800 maturation Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
MJDFHMBRNYFGHC-PKNBQFBNSA-N methyl (e)-2-benzyl-3-methoxyprop-2-enoate Chemical compound CO\C=C(C(=O)OC)/CC1=CC=CC=C1 MJDFHMBRNYFGHC-PKNBQFBNSA-N 0.000 description 1
CNTVWMRWECWTRT-UHFFFAOYSA-N methyl 2,5-dichloro-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C=C1Cl CNTVWMRWECWTRT-UHFFFAOYSA-N 0.000 description 1
GSEAWBXOZLYRQE-UHFFFAOYSA-N methyl 2-benzyl-3-hydroxyprop-2-enoate Chemical compound COC(=O)C(=CO)CC1=CC=CC=C1 GSEAWBXOZLYRQE-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
KFKXSMSQHIOMSO-UHFFFAOYSA-N methyl 2-oxoacetate Chemical compound COC(=O)C=O KFKXSMSQHIOMSO-UHFFFAOYSA-N 0.000 description 1
ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical group CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XQIJIALOJPIKGX-UHFFFAOYSA-N naphthalene 1,2-oxide Chemical compound C1=CC=C2C3OC3C=CC2=C1 XQIJIALOJPIKGX-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000002420 orchard Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
235000019629 palatability Nutrition 0.000 description 1
OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
239000011505 plaster Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000001965 potato dextrose agar Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
239000012882 rooting medium Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
DEWVPZYHFVYXMZ-QCILGFJPSA-M sodium;(3ar,4as,8ar,8bs)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate Chemical compound [Na+].O([C@H]12)C(C)(C)OC[C@@H]1O[C@]1(C([O-])=O)[C@H]2OC(C)(C)O1 DEWVPZYHFVYXMZ-QCILGFJPSA-M 0.000 description 1
HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000005082 stem growth Effects 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
239000004308 thiabendazole Substances 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
235000010296 thiabendazole Nutrition 0.000 description 1
229960004546 thiabendazole Drugs 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 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
229960002447 thiram Drugs 0.000 description 1
OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
OAGIOQZKOZPWKF-UHFFFAOYSA-N tributyl-[(2,4-dichlorophenyl)methyl]phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl OAGIOQZKOZPWKF-UHFFFAOYSA-N 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000009105 vegetative growth Effects 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 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
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- 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
- 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
- A01N37/44—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

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

DK198603945A 1985-08-22 1986-08-19 2-substituerede methyl-propenoatforbindelser, en fremgangsmåde til deres fremstilling, samt deres anvendelse som fungicider DK173341B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB858521082A GB8521082D0 (en)	1985-08-22	1985-08-22	Fungicides
GB8521082		1985-08-22

Publications (3)

Publication Number	Publication Date
DK394586D0 DK394586D0 (da)	1986-08-19
DK394586A DK394586A (da)	1987-02-23
DK173341B1 true DK173341B1 (da)	2000-07-31

Family

ID=10584187

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198603945A DK173341B1 (da)	1985-08-22	1986-08-19	2-substituerede methyl-propenoatforbindelser, en fremgangsmåde til deres fremstilling, samt deres anvendelse som fungicider

Country Status (17)

Country	Link
US (3)	US4802913A (fr)
EP (1)	EP0212859B1 (fr)
JP (1)	JPH0819047B2 (fr)
KR (1)	KR910000249B1 (fr)
AU (1)	AU598741B2 (fr)
BR (1)	BR8603992A (fr)
CA (1)	CA1280417C (fr)
DE (1)	DE3674114D1 (fr)
DK (1)	DK173341B1 (fr)
ES (1)	ES2001880A6 (fr)
GB (2)	GB8521082D0 (fr)
HU (1)	HU201726B (fr)
IE (1)	IE59221B1 (fr)
MY (1)	MY100929A (fr)
NZ (1)	NZ217048A (fr)
PT (1)	PT83233B (fr)
ZA (1)	ZA865792B (fr)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6013722A (ja) *	1983-07-05	1985-01-24	Teijin Yuka Kk	エチルベンゼンの異性化方法
DE3906160A1 (de) *	1989-02-28	1990-10-11	Basf Ag	Ortho-substituierte 1-naphthylether und diese enthaltende fungizide
US5286750A (en) *	1989-10-11	1994-02-15	Basf Aktiengesellschaft	Phenylacetic acid derivatives and fungicides containing them
US5187170A (en) *	1989-11-16	1993-02-16	Basf Aktiengesellschaft	Thiocarboxylic esters and fungicides containing them
GB8926630D0 (en) *	1989-11-24	1990-01-17	Ici Plc	Fungicides
DE4215469A1 (de) *	1992-05-11	1993-11-18	Bayer Ag	Pyridyl-Derivate
US5371095A (en) *	1990-02-08	1994-12-06	Bayer Aktiengesellschaft	Pyridyl compounds which have pesticidal activity
PH11991042549B1 (fr) *	1990-06-05	2000-12-04
DE4025891A1 (de) *	1990-08-16	1992-02-20	Bayer Ag	Pyrimidyl-substituierte acrylsaeureester
DE4108029A1 (de) *	1991-03-13	1992-09-17	Bayer Ag	Triazinyl-substituierte acrylsaeureester
DE4142191A1 (de) *	1991-12-20	1993-06-24	Bayer Ag	Verfahren zur herstellung von 3-alkoxy-acrylestern
DE4227748A1 (de) *	1992-08-21	1994-02-24	Bayer Ag	Pyridyloxy-acrylsäureester
DE69316505T2 (de) *	1992-10-08	1998-07-16	Koninkl Philips Electronics Nv	Bandreinigungssystem mit Magnetbandkassette und Magnetbandgerät
US5436369A (en) *	1993-06-16	1995-07-25	Bristol-Myers Squibb Company	Alicyclic phospholipase A2 inhibitors
JPH11508227A (ja) *	1995-05-09	1999-07-21	ビーエーエスエフアクチェンゲゼルシャフト	（ヘテロ）アリールオキシ−、−チオ−および−アミノクロトン酸エステル、その製造法および使用法
FR2751642B1 (fr) *	1996-07-24	1998-09-11	Hoechst Schering Agrevo Sa	Nouveaux derives de l'acide beta-methoxy acrylique, leur procede de preparation et leur application comme pesticides
WO1998027562A1 (fr) *	1996-12-18	1998-06-25	Medtronic, Inc.	Condensateurs a haute densite d'energie et composes entrant dans leur fabrication
JPH10218839A (ja)	1997-02-06	1998-08-18	Mitsubishi Chem Corp	フェノキシ酢酸誘導体並びにそれを含有する農園芸用除草剤
AU3536699A (en)	1998-04-27	1999-11-16	Ihara Chemical Industry Co. Ltd.	3-arylphenyl sulfide derivatives and insecticides and miticides
US6409809B1 (en)	1999-02-08	2002-06-25	Cognis Corporation	Pigmented coatings exhibiting reduced fading
WO2001000562A1 (fr) *	1999-06-25	2001-01-04	Sumitomo Chemical Company, Limited	Derives d'acide acrylique, leur utilisation et intermediaires pour leur preparation
US6846783B2 (en)	2000-06-22	2005-01-25	The Lubrizol Corporation	Acylatign agents and dispersants for lubricating oil and fuels
WO2002041891A2 (fr) *	2000-11-01	2002-05-30	The Procter & Gamble Company	Traitement de l'infection par le vih
GB0028164D0 (en) *	2000-11-18	2001-01-03	Lovesgrove Res Ltd	Compositions for, and a method of, exterminating pests
JP2005521712A (ja) *	2002-03-26	2005-07-21	アリゾナボードオブリージェンツオンビハーフオブザユニバーシティーオブアリゾナ	弱塩基の可溶化
AU2003289229A1 (en) *	2002-12-06	2004-06-30	Kaneka Corporation	Process for producing optically active 3-hydroxypropionic ester derivative
BRPI0402260B1 (pt) *	2004-06-15	2015-02-18	Botica Com Farmaceutica Ltda	Composição para produtos de higiene, cosméticos e perfumes.
AR115870A1 (es)	2018-07-31	2021-03-10	Sumitomo Chemical Co	MÉTODO PARA CONTROLAR EL HONGO DE LA ROYA DE LA SOJA QUE TIENE RESISTENCIA AL INHIBIDOR DE SITIO Qₒ
AR116628A1 (es) *	2018-10-18	2021-05-26	Syngenta Crop Protection Ag	Compuestos microbiocidas
WO2020165403A1 (fr)	2019-02-15	2020-08-20	Syngenta Crop Protection Ag	Dérivés de thiazole substitués par phényle en tant que composés microbiocides
GB201903942D0 (en) *	2019-03-22	2019-05-08	Syngenta Crop Protection Ag	Microbiocidal compounds
CN114026060A (zh) *	2019-06-28	2022-02-08	住友化学株式会社	丙烯酸酯衍生物、其用途及其制造中间体
US20230150909A1 (en) *	2020-01-31	2023-05-18	Sumitomo Chemical Company, Limited	Phenylacetic acid derivative, use therefor, and production intermediate thereof
UY39052A (es)	2020-01-31	2021-03-26	Sumitomo Chemical Co	MÉTODO DE CONTROL DEL HONGO DE LA ROYA DE LA SOJA QUE ES RESISTENTE A LOS INHIBIDORES Qo
UY39115A (es)	2020-03-05	2021-10-29	Syngenta Crop Protection Ag	Mezclas fungicidas de derivados de arilo metoxiacrilato
KR20250174036A (ko) *	2023-04-10	2025-12-11	스미또모 가가꾸 가부시끼가이샤	3-하이드록시비페닐 화합물 및 그 유도체의 제조 방법
AR133238A1 (es) *	2023-07-19	2025-09-10	Sumitomo Chemical Co	Compuesto de dimetilpent-2-enodioato y uso del mismo
AR133235A1 (es) *	2023-07-19	2025-09-10	Sumitomo Chemical Co	Compuesto de metileno bisbifenilo y uso del mismo
AR133236A1 (es) *	2023-07-19	2025-09-10	Sumitomo Chemical Co	Compuesto derivado del ácido acrílico y uso del mismo
PY2459059A (es) *	2023-07-19	2025-04-22	Sumitomo Chemical Co	Compuesto de bifenilo y uso del mismo
CN116731643B (zh) *	2023-08-14	2023-11-03	广东远东高分子科技有限公司	一种钢排钉安装用胶粘剂及其制备工艺
AR133732A1 (es) *	2023-09-08	2025-10-29	Pi Industries Ltd	Nuevos compuestos de 1,2,4-oxadiazoles como fungicida

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3922345A (en) *	1971-10-29	1975-11-25	Pfizer	Pyrimidinones and hydroxy pyrimidines
US3941889A (en) *	1972-09-08	1976-03-02	Pfizer Inc.	5-(Substituted phenoxy)-4-amino pyrimidines as anti-ulcer agents
GB1563201A (en) *	1975-11-05	1980-03-19	Shell Int Research	Preparation of herbicidally acitve alanine derivatives
DE2550519A1 (de) *	1975-11-11	1977-05-12	Bayer Ag	Chlorsubstituierte vinylamino-benzoesaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren
US4492683A (en) *	1982-08-06	1985-01-08	Buffalo Color Corporation	Method for inhibiting the growth of fungi with phenyl glycine compounds
NZ213630A (en) *	1984-10-19	1990-02-26	Ici Plc	Acrylic acid derivatives and fungicidal compositions

1985
- 1985-08-22 GB GB858521082A patent/GB8521082D0/en active Pending
1986
- 1986-07-23 DE DE8686305655T patent/DE3674114D1/de not_active Expired - Lifetime
- 1986-07-23 EP EP86305655A patent/EP0212859B1/fr not_active Expired - Lifetime
- 1986-07-23 GB GB8617984A patent/GB2179346B/en not_active Expired
- 1986-07-25 IE IE198686A patent/IE59221B1/en not_active IP Right Cessation
- 1986-07-31 NZ NZ217048A patent/NZ217048A/xx unknown
- 1986-08-01 ZA ZA865792A patent/ZA865792B/xx unknown
- 1986-08-05 US US06/893,272 patent/US4802913A/en not_active Expired - Lifetime
- 1986-08-13 AU AU61099/86A patent/AU598741B2/en not_active Ceased
- 1986-08-18 HU HU863604A patent/HU201726B/hu not_active IP Right Cessation
- 1986-08-19 DK DK198603945A patent/DK173341B1/da not_active IP Right Cessation
- 1986-08-20 CA CA000516428A patent/CA1280417C/fr not_active Expired - Lifetime
- 1986-08-21 KR KR1019860006893A patent/KR910000249B1/ko not_active Expired
- 1986-08-21 PT PT83233A patent/PT83233B/pt not_active IP Right Cessation
- 1986-08-21 BR BR8603992A patent/BR8603992A/pt not_active IP Right Cessation
- 1986-08-22 ES ES8601301A patent/ES2001880A6/es not_active Expired
- 1986-08-22 JP JP61195741A patent/JPH0819047B2/ja not_active Expired - Fee Related
1987
- 1987-04-03 MY MYPI87000430A patent/MY100929A/en unknown
1988
- 1988-10-31 US US07/264,874 patent/US4913721A/en not_active Expired - Lifetime
1989
- 1989-10-03 US US07/416,609 patent/US5124353A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IE861986L (en)	1987-02-22
MY100929A (en)	1991-05-31
KR870002044A (ko)	1987-03-28
US5124353A (en)	1992-06-23
PT83233A (en)	1986-09-01
US4802913A (en)	1989-02-07
ES2001880A6 (es)	1988-07-01
CA1280417C (fr)	1991-02-19
GB8521082D0 (en)	1985-09-25
JPH0819047B2 (ja)	1996-02-28
IE59221B1 (en)	1994-01-26
PT83233B (pt)	1989-03-30
EP0212859B1 (fr)	1990-09-12
HUT41597A (en)	1987-05-28
KR910000249B1 (ko)	1991-01-23
DK394586A (da)	1987-02-23
HU201726B (en)	1990-12-28
GB8617984D0 (en)	1986-08-28
DE3674114D1 (de)	1990-10-18
EP0212859A3 (en)	1988-05-04
EP0212859A2 (fr)	1987-03-04
AU6109986A (en)	1987-02-26
BR8603992A (pt)	1987-04-07
GB2179346A (en)	1987-03-04
US4913721A (en)	1990-04-03
JPS6248649A (ja)	1987-03-03
ZA865792B (en)	1987-04-29
AU598741B2 (en)	1990-07-05
NZ217048A (en)	1989-11-28
GB2179346B (en)	1989-08-02
DK394586D0 (da)	1986-08-19

Legal Events

Date	Code	Title	Description
2000-07-31	B1	Patent granted (law 1993)
2003-03-31	PBP	Patent lapsed	Country of ref document: DK

Publication	Publication Date	Title
DK173341B1 (da)	2000-07-31	2-substituerede methyl-propenoatforbindelser, en fremgangsmåde til deres fremstilling, samt deres anvendelse som fungicider
RU2024496C1 (ru)	1994-12-15	Производные пропеновой кислоты, обладающие фунгицидной активностью
JP6867370B2 (ja)	2021-04-28	トリアゾール誘導体、その中間体および殺真菌剤としてのそれらの使用
RU1811528C (ru)	1993-04-23	Способ получени производных пиридина
JP6501802B2 (ja)	2019-04-17	ジフルオロメチル−ニコチン酸−インダニルカルボキサミド類
DK173235B1 (da)	2000-05-01	Acrylsyrederivater i form af (E)-isomerer, deres fremstilling, fungicider indeholdende disse samt anvendelsen af fungicidet
DK164595B (da)	1992-07-20	3-methoxy-2-pyridyl-methylacrylater, fremgangsmaade til fremstilling deraf, middel indeholdende forbindelserne og disses eller midlets anvendelse til bekaempelse af svampe
JPH07121906B2 (ja)	1995-12-25	アクリル酸誘導体、その製造方法及びこれを有効成分とする農薬組成物
HU201009B (en)	1990-09-28	Process for producing 2-heterocyclic-3-alkoxy-(or alkylthio)-acrylic acid esters and fungicides comprising such compounds as active ingredient
DE3788928T2 (de)	1994-05-19	Chemische Verbindungen.
DK171398B1 (da)	1996-10-14	1-substituerede indoler, fremgangsmåde og mellemprodukter til fremstilling heraf samt indolernes anvendelse som og i fungicide, plantevækstregulerende og miticide midler
EP1236717B1 (fr)	2004-02-04	Composes oxime o-ether et fongicides utiles dans l'agriculture et l'horticulture
RO110665B1 (ro)	1996-03-29	Derivati de piridilciclopropani, procedee pentru prepararea acestora, intermediari pentru realizarea procedeelor, compozitie fungicida si metoda pentru combaterea fungilor
TW201641493A (zh)	2016-12-01	新穎三唑衍生物
KR19990082300A (ko)	1999-11-25	살균제로서의 피리딘 유도체
EP0193270B1 (fr)	1991-09-11	Composés hétérocycliques
CN102471286A (zh)	2012-05-23	苯基(氧基/硫基)烷醇衍生物
US5229393A (en)	1993-07-20	Fungicidal alpha substituted acrylates
JPS63287750A (ja)	1988-11-24	プロペン酸化合物、その製造法及びそれを含有する殺菌組成物
JPH0557261B2 (fr)	1993-08-23
JPH0656784A (ja)	1994-03-01	殺菌性化合物、その製造法、その中間体、殺菌剤組成物及びカビ菌類の防除方法
KR950009751B1 (ko)	1995-08-28	살균제
TW201144320A (en)	2011-12-16	Dithiinopyridazinone derivatives
JPH05194506A (ja)	1993-08-03	ピリジルチアゾール系化合物、その製造方法、殺菌剤組成物及び殺菌方法