IL106971A

IL106971A - Fluoroalkenylthio- substituted benzoxazoles and benzthiazoles and their use as pesticides

Fluoroalkenylthio- substituted benzoxazoles and benzthiazoles and their use as pesticides

Info

Publication number: IL106971A
Authority: IL; Israel
Prior art keywords: compound; difluorobut; enylthio; formula; optionally substituted
Prior art date: 1992-09-16

Application number

IL106971A

Other languages

English (en)

Other versions

IL106971A0 (en

Original Assignee

Zeneca Ltd

Priority date

1992-09-16

Filing date

1993-09-10

Publication date

1998-06-15

1993-09-10 Application filed by Zeneca Ltd filed Critical Zeneca Ltd

1993-09-10 Priority to IL11981093A priority Critical patent/IL119810A/en

1993-12-28 Publication of IL106971A0 publication Critical patent/IL106971A0/xx

1996-12-11 Priority to IL11981096A priority patent/IL119810A0/xx

1998-06-15 Publication of IL106971A publication Critical patent/IL106971A/en

Links

IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 29
150000000183 1,3-benzoxazoles Chemical class 0.000 title description 4
239000000575 pesticide Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 329
-1 nitro, phenoxy Chemical group 0.000 claims description 181
239000000203 mixture Substances 0.000 claims description 105
238000002360 preparation method Methods 0.000 claims description 95
238000000034 method Methods 0.000 claims description 69
238000006243 chemical reaction Methods 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 48
241000607479 Yersinia pestis Species 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
241000244206 Nematoda Species 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000001188 haloalkyl group Chemical group 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
125000004438 haloalkoxy group Chemical group 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 17
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
239000005864 Sulphur Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
241000238631 Hexapoda Species 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000005518 carboxamido group Chemical group 0.000 claims description 7
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 7
230000001069 nematicidal effect Effects 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
230000000855 fungicidal effect Effects 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
125000000232 haloalkynyl group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 5
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
125000005108 alkenylthio group Chemical group 0.000 claims description 5
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
125000005133 alkynyloxy group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
238000007254 oxidation reaction Methods 0.000 claims description 5
241000233866 Fungi Species 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000005109 alkynylthio group Chemical group 0.000 claims description 4
238000007269 dehydrobromination reaction Methods 0.000 claims description 4
125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000004991 fluoroalkenyl group Chemical group 0.000 claims description 4
125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
230000000895 acaricidal effect Effects 0.000 claims description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
239000012876 carrier material Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
125000004428 fluoroalkoxy group Chemical group 0.000 claims description 3
125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
125000005292 haloalkynyloxy group Chemical group 0.000 claims description 3
239000003701 inert diluent Substances 0.000 claims description 3
230000000749 insecticidal effect Effects 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000005336 allyloxy group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000004965 chloroalkyl group Chemical group 0.000 claims description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims 2
125000003107 substituted aryl group Chemical group 0.000 claims 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 207
238000005481 NMR spectroscopy Methods 0.000 description 130
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 117
239000007787 solid Substances 0.000 description 94
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
239000003921 oil Substances 0.000 description 81
235000019198 oils Nutrition 0.000 description 81
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
239000000243 solution Substances 0.000 description 72
229940093499 ethyl acetate Drugs 0.000 description 69
235000019439 ethyl acetate Nutrition 0.000 description 69
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 66
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 60
239000000047 product Substances 0.000 description 59
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 55
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
229910052943 magnesium sulfate Inorganic materials 0.000 description 33
235000019341 magnesium sulphate Nutrition 0.000 description 33
238000012360 testing method Methods 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
239000004480 active ingredient Substances 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000000126 substance Substances 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
239000007858 starting material Substances 0.000 description 22
229960004132 diethyl ether Drugs 0.000 description 21
238000011282 treatment Methods 0.000 description 21
239000012074 organic phase Substances 0.000 description 20
238000010992 reflux Methods 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
229960001866 silicon dioxide Drugs 0.000 description 20
238000001704 evaporation Methods 0.000 description 19
230000008020 evaporation Effects 0.000 description 19
241000196324 Embryophyta Species 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000725 suspension Substances 0.000 description 18
230000000694 effects Effects 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
239000010410 layer Substances 0.000 description 15
239000007788 liquid Substances 0.000 description 15
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
239000008187 granular material Substances 0.000 description 13
239000012044 organic layer Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
238000001914 filtration Methods 0.000 description 12
239000012442 inert solvent Substances 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
239000002689 soil Substances 0.000 description 12
239000002585 base Substances 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
239000012267 brine Substances 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
239000000843 powder Substances 0.000 description 10
230000009467 reduction Effects 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
239000003480 eluent Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000002917 insecticide Substances 0.000 description 8
125000000896 monocarboxylic acid group Chemical group 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
241000894007 species Species 0.000 description 8
239000004546 suspension concentrate Substances 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
HXQIFAAGEIMFHS-UHFFFAOYSA-N 4,4-difluorobut-3-enyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCC=C(F)F)C=C1 HXQIFAAGEIMFHS-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
241000721621 Myzus persicae Species 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
239000002270 dispersing agent Substances 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000000463 material Substances 0.000 description 7
239000002609 medium Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical class C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 6
241001124076 Aphididae Species 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
239000003094 microcapsule Substances 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 5
CCSNPDFWCFVAEH-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,3-benzoxazol-6-amine Chemical compound NC1=CC=C2N=C(SCCC=C(F)F)OC2=C1 CCSNPDFWCFVAEH-UHFFFAOYSA-N 0.000 description 5
OHRVPBCRXJFTMW-UHFFFAOYSA-N 2-(4,4-difluorobut-3-enylsulfanyl)-1,3-benzoxazol-6-ol Chemical compound OC1=CC=C2N=C(SCCC=C(F)F)OC2=C1 OHRVPBCRXJFTMW-UHFFFAOYSA-N 0.000 description 5
241000243786 Meloidogyne incognita Species 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
239000006071 cream Substances 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000007921 spray Substances 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
239000000080 wetting agent Substances 0.000 description 5
239000011701 zinc Substances 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
OMYOTPPJTUENQI-UHFFFAOYSA-N (4-bromo-4,4-difluorobutyl) methanesulfonate Chemical compound CS(=O)(=O)OCCCC(F)(F)Br OMYOTPPJTUENQI-UHFFFAOYSA-N 0.000 description 4
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