DE4408005A1 - Substituierte Azadioxacycloalkene - Google Patents

Info

Publication number

DE4408005A1

DE4408005A1 DE4408005A DE4408005A DE4408005A1 DE 4408005 A1 DE4408005 A1 DE 4408005A1 DE 4408005 A DE4408005 A DE 4408005A DE 4408005 A DE4408005 A DE 4408005A DE 4408005 A1 DE4408005 A1 DE 4408005A1

Authority

DE

Germany

Prior art keywords

cyano

carbon atoms

methyl

alkyl

optionally substituted

Prior art date

1993-08-11

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.)

Withdrawn

Links

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• -1 3-thia-1-propene-2,3-diyl group Chemical group 0.000 claims description 274
• 125000004432 carbon atom Chemical group C* 0.000 claims description 77
• 229910052736 halogen Inorganic materials 0.000 claims description 51
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 50
• 239000000460 chlorine Chemical group 0.000 claims description 50
• 229910052801 chlorine Inorganic materials 0.000 claims description 50
• 150000001875 compounds Chemical class 0.000 claims description 49
• 229910052731 fluorine Inorganic materials 0.000 claims description 49
• 239000011737 fluorine Substances 0.000 claims description 49
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
• 150000002367 halogens Chemical group 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 33
• 239000000203 mixture Substances 0.000 claims description 32
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
• 125000005843 halogen group Chemical group 0.000 claims description 30
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• 239000001301 oxygen Substances 0.000 claims description 30
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
• 229910052794 bromium Inorganic materials 0.000 claims description 25
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 238000002360 preparation method Methods 0.000 claims description 24
• 125000001153 fluoro group Chemical group F* 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 19
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 18
• 239000003085 diluting agent Substances 0.000 claims description 18
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 17
• 229910052717 sulfur Chemical group 0.000 claims description 17
• 239000011593 sulfur Chemical group 0.000 claims description 17
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• 239000000417 fungicide Substances 0.000 claims description 7
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
• 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 4
• 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• 239000004606 Fillers/Extenders Substances 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
• 125000005277 alkyl imino group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 230000000694 effects Effects 0.000 claims description 4
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 4
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
• 125000005549 heteroarylene group Chemical group 0.000 claims description 4
• 125000005027 hydroxyaryl group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 239000013543 active substance Substances 0.000 claims description 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 3
• 230000000855 fungicidal effect Effects 0.000 claims description 3
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
• 125000004970 halomethyl group Chemical group 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 239000012433 hydrogen halide Substances 0.000 claims description 3
• 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
• 238000011065 in-situ storage Methods 0.000 claims description 3
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
• 125000000732 arylene group Chemical group 0.000 claims description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 claims description 2
• 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 2
• 229950004394 ditiocarb Drugs 0.000 claims description 2
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
• 238000002955 isolation Methods 0.000 claims description 2
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000004957 naphthylene group Chemical group 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
• 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
• 241000233866 Fungi Species 0.000 claims 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• 239000007858 starting material Substances 0.000 description 28
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
• 239000004480 active ingredient Substances 0.000 description 17
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
• 241000196324 Embryophyta Species 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 239000002904 solvent Substances 0.000 description 13
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 11
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 238000004519 manufacturing process Methods 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• 239000003995 emulsifying agent Substances 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 235000011181 potassium carbonates Nutrition 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• 229910052938 sodium sulfate Inorganic materials 0.000 description 8
• 235000011152 sodium sulphate Nutrition 0.000 description 8
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 241000228453 Pyrenophora Species 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 239000008187 granular material Substances 0.000 description 5
• 238000002844 melting Methods 0.000 description 5
• 230000008018 melting Effects 0.000 description 5
• 235000011118 potassium hydroxide Nutrition 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
• PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 125000002877 alkyl aryl group Chemical group 0.000 description 4
• 229950005499 carbon tetrachloride Drugs 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 238000004440 column chromatography Methods 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
• QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• 239000002243 precursor Substances 0.000 description 4
• 230000009885 systemic effect Effects 0.000 description 4
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• CJJAVRWGJRYWMI-UHFFFAOYSA-N 2-(oxan-2-yloxy)-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OC1CCCCO1 CJJAVRWGJRYWMI-UHFFFAOYSA-N 0.000 description 3
• 239000005660 Abamectin Substances 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
• 241001330975 Magnaporthe oryzae Species 0.000 description 3
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
• 238000005481 NMR spectroscopy Methods 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 240000007594 Oryza sativa Species 0.000 description 3
• 241000736122 Parastagonospora nodorum Species 0.000 description 3
• 241000233614 Phytophthora Species 0.000 description 3
• 241000520648 Pyrenophora teres Species 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 239000012141 concentrate Substances 0.000 description 3
• 239000010949 copper Substances 0.000 description 3
• 229910052802 copper Inorganic materials 0.000 description 3
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