UA77546C2

UA77546C2 - Pyrazolepyrimidines and using thereof to control harmful organisms

Pyrazolepyrimidines and using thereof to control harmful organisms Download PDF

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Publication number: UA77546C2
Authority: UA; Ukraine
Prior art keywords: formula; carbon atoms; methyl; plants; cycloalkyl
Prior art date: 2002-05-29

Application number

UA20041210941A

Other languages

English (en)

Ukrainian (uk)

Priority date

2002-05-29

Filing date

2003-05-16

Publication date

2006-12-15

2003-05-16 Application filed filed Critical

2006-12-15 Publication of UA77546C2 publication Critical patent/UA77546C2/uk

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APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 claims abstract description 17
-1 amino, hydroxy Chemical group 0.000 claims description 271
239000013543 active substance Substances 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 36
125000000753 cycloalkyl group Chemical group 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 35
150000002367 halogens Chemical class 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 33
239000003085 diluting agent Substances 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
125000001188 haloalkyl group Chemical group 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
125000004663 dialkyl amino group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
XMBHGEAQFMUJMX-UHFFFAOYSA-N 2,4-dihydro-1h-pyrazolo[4,3-d]pyrimidine-3,5-dione Chemical class N1=C(O)N=C2C(O)=NNC2=C1 XMBHGEAQFMUJMX-UHFFFAOYSA-N 0.000 claims description 5
125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
125000006323 alkenyl amino group Chemical group 0.000 claims description 2
125000006319 alkynyl amino group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
238000000034 method Methods 0.000 abstract description 90
239000000126 substance Substances 0.000 abstract description 22
239000000543 intermediate Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
241000196324 Embryophyta Species 0.000 description 84
125000004432 carbon atom Chemical group C* 0.000 description 80
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
239000000203 mixture Substances 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
241000894007 species Species 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 21
239000000460 chlorine Substances 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
230000009471 action Effects 0.000 description 16
239000011737 fluorine Substances 0.000 description 16
229910052731 fluorine Inorganic materials 0.000 description 16
239000000463 material Substances 0.000 description 16
239000000047 product Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
125000004494 ethyl ester group Chemical group 0.000 description 15
238000007796 conventional method Methods 0.000 description 14
244000005700 microbiome Species 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
238000012545 processing Methods 0.000 description 14
239000002904 solvent Substances 0.000 description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
150000001412 amines Chemical class 0.000 description 13
239000003995 emulsifying agent Substances 0.000 description 13
230000003993 interaction Effects 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
229910052794 bromium Inorganic materials 0.000 description 12
125000005843 halogen group Chemical group 0.000 description 12
235000011167 hydrochloric acid Nutrition 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
241000700605 Viruses Species 0.000 description 11
238000001816 cooling Methods 0.000 description 11
230000001681 protective effect Effects 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
241000607479 Yersinia pestis Species 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
239000003960 organic solvent Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000007858 starting material Substances 0.000 description 10
241000233866 Fungi Species 0.000 description 9
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
240000008042 Zea mays Species 0.000 description 9
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
235000002017 Zea mays subsp mays Nutrition 0.000 description 9
239000002585 base Substances 0.000 description 9
235000005822 corn Nutrition 0.000 description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
235000011118 potassium hydroxide Nutrition 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229920000742 Cotton Polymers 0.000 description 8
244000299507 Gossypium hirsutum Species 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 7
238000011160 research Methods 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
241000894006 Bacteria Species 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
235000010469 Glycine max Nutrition 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
238000009835 boiling Methods 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
150000002366 halogen compounds Chemical class 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
239000002689 soil Substances 0.000 description 6
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 6
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 6
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
244000068988 Glycine max Species 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
125000002877 alkyl aryl group Chemical group 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
230000006378 damage Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000001153 fluoro group Chemical group F* 0.000 description 5
239000008187 granular material Substances 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
230000009261 transgenic effect Effects 0.000 description 5
239000002023 wood Substances 0.000 description 5
ZKSRIPVNRIUEOM-UHFFFAOYSA-N 1,2-dihydropyrazolo[4,3-d]pyrimidin-3-one Chemical class N1=CN=C2C(O)=NNC2=C1 ZKSRIPVNRIUEOM-UHFFFAOYSA-N 0.000 description 4
CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
244000061456 Solanum tuberosum Species 0.000 description 4
235000002595 Solanum tuberosum Nutrition 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
150000004657 carbamic acid derivatives Chemical class 0.000 description 4
229950005499 carbon tetrachloride Drugs 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000000417 fungicide Substances 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
235000004977 Brassica sinapistrum Nutrition 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
244000070406 Malus silvestris Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
125000005396 acrylic acid ester group Chemical group 0.000 description 3
125000002723 alicyclic group Chemical group 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000003899 bactericide agent Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
229940117389 dichlorobenzene Drugs 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
238000005516 engineering process Methods 0.000 description 3
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