CZ254696A3

CZ254696A3 - Oxime derivatives, process of their preparation and their use for fighting pest

Oxime derivatives, process of their preparation and their use for fighting pest Download PDF

Info

Publication number: CZ254696A3
Authority: CZ; Czechia
Prior art keywords: group; optionally; cyano; butyl; substituted
Prior art date: 1994-03-10

Application number

CZ962546A

Other languages

Czech (cs)

English (en)

Inventor

Peter Gerdes

Herbert Gayer

Bernd-Wieland Kruger

Bernd Gallenkamp

Heinz-Wilhelm Dehne

Stefen Dutzmann

Gerd Hanssler

Klaus Stenzel

Original Assignee

Bayer Ag

Priority date

1994-03-10

Filing date

1995-02-27

Publication date

1996-12-11

1995-02-27 Application filed by Bayer Ag filed Critical Bayer Ag

1996-12-11 Publication of CZ254696A3 publication Critical patent/CZ254696A3/cs

Links

238000002360 preparation method Methods 0.000 title claims description 30
238000000034 method Methods 0.000 title claims description 25
150000002923 oximes Chemical class 0.000 title claims description 17
241000607479 Yersinia pestis Species 0.000 title claims description 7
-1 3-aza-1-propene-2,3-diyl group Chemical group 0.000 claims description 468
125000004432 carbon atom Chemical group C* 0.000 claims description 119
229910052731 fluorine Inorganic materials 0.000 claims description 95
239000011737 fluorine Substances 0.000 claims description 93
229910052801 chlorine Inorganic materials 0.000 claims description 91
239000000460 chlorine Substances 0.000 claims description 90
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 87
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 86
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 73
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 72
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 71
229910052736 halogen Inorganic materials 0.000 claims description 68
150000002367 halogens Chemical group 0.000 claims description 61
125000000217 alkyl group Chemical group 0.000 claims description 60
125000004093 cyano group Chemical group *C#N 0.000 claims description 60
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 57
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 51
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
125000005843 halogen group Chemical group 0.000 claims description 47
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 45
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 42
125000003545 alkoxy group Chemical group 0.000 claims description 40
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 39
229910052794 bromium Inorganic materials 0.000 claims description 39
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 38
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 38
125000004430 oxygen atom Chemical group O* 0.000 claims description 32
229910052717 sulfur Inorganic materials 0.000 claims description 29
125000001153 fluoro group Chemical group F* 0.000 claims description 27
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 25
229910052757 nitrogen Inorganic materials 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 23
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
125000001188 haloalkyl group Chemical group 0.000 claims description 23
125000000623 heterocyclic group Chemical group 0.000 claims description 23
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
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 22
125000000753 cycloalkyl group Chemical group 0.000 claims description 21
125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 19
125000003282 alkyl amino group Chemical group 0.000 claims description 18
125000004663 dialkyl amino group Chemical group 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 18
125000000547 substituted alkyl group Chemical group 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
125000004414 alkyl thio group Chemical group 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 16
239000011593 sulfur Substances 0.000 claims description 16
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 15
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 15
125000004438 haloalkoxy group Chemical group 0.000 claims description 14
125000001624 naphthyl group Chemical group 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000004434 sulfur atom Chemical group 0.000 claims description 13
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
150000001408 amides Chemical class 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
125000002541 furyl group Chemical group 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000000335 thiazolyl group Chemical group 0.000 claims description 9
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 9
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 8
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
125000000262 haloalkenyl group Chemical group 0.000 claims description 8
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 8
125000002098 pyridazinyl group Chemical group 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
125000003302 alkenyloxy group Chemical group 0.000 claims description 7
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000004995 haloalkylthio group Chemical group 0.000 claims description 7
125000001786 isothiazolyl group Chemical group 0.000 claims description 7
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000005291 haloalkenyloxy group Chemical group 0.000 claims description 6
150000002443 hydroxylamines Chemical class 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
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 6
125000000168 pyrrolyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 5
238000002955 isolation Methods 0.000 claims description 5
125000000842 isoxazolyl group Chemical group 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 5
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 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
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000005549 heteroarylene group Chemical group 0.000 claims description 4
125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims description 4
125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 4
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
MJIWQHRXSLOUJN-UHFFFAOYSA-N 1,2,4-triazin-3-amine Chemical compound NC1=NC=CN=N1 MJIWQHRXSLOUJN-UHFFFAOYSA-N 0.000 claims description 2
RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 claims description 2
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical compound C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 claims description 2
ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical compound NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 claims description 2
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
HFZZTHJMXZSGFP-UHFFFAOYSA-N 1-benzofuran-2-amine Chemical compound C1=CC=C2OC(N)=CC2=C1 HFZZTHJMXZSGFP-UHFFFAOYSA-N 0.000 claims description 2
DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 claims description 2
JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 2
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
RNQOHYCJKWDINT-UHFFFAOYSA-N N-phenoxy-N-phenylsulfanylaniline Chemical compound O(C1=CC=CC=C1)N(C1=CC=CC=C1)SC1=CC=CC=C1 RNQOHYCJKWDINT-UHFFFAOYSA-N 0.000 claims description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 2
125000005277 alkyl imino group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
125000000732 arylene group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000005605 benzo group Chemical group 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
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 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
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 claims description 2
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000004957 naphthylene group Chemical group 0.000 claims description 2
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
WHLAXDUXKMECTM-UHFFFAOYSA-N oxadiazol-4-amine Chemical compound NC1=CON=N1 WHLAXDUXKMECTM-UHFFFAOYSA-N 0.000 claims description 2
ICBYIKRIEVEFCX-UHFFFAOYSA-N oxan-2-amine Chemical compound NC1CCCCO1 ICBYIKRIEVEFCX-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([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
XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims description 2
LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 claims description 2
125000005650 substituted phenylene group Chemical group 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 claims description 2
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims description 2
IYCKMNAVTMOAKD-UHFFFAOYSA-N 1,2-thiazol-3-amine Chemical compound NC=1C=CSN=1 IYCKMNAVTMOAKD-UHFFFAOYSA-N 0.000 claims 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
125000005236 alkanoylamino group Chemical group 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 claims 1
229950004394 ditiocarb Drugs 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
239000000945 filler Substances 0.000 claims 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
125000005305 thiadiazolinyl group Chemical group 0.000 claims 1
125000002769 thiazolinyl group Chemical group 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
150000001875 compounds Chemical class 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
241000196324 Embryophyta Species 0.000 description 30
239000002904 solvent Substances 0.000 description 26
238000012360 testing method Methods 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000003995 emulsifying agent Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000004480 active ingredient Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 11
230000001681 protective effect Effects 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
238000011081 inoculation Methods 0.000 description 10
238000005507 spraying Methods 0.000 description 10
239000007858 starting material Substances 0.000 description 10
239000003208 petroleum Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
125000002877 alkyl aryl group Chemical group 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
229920000151 polyglycol Polymers 0.000 description 8
239000010695 polyglycol Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
238000011156 evaluation Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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