HU225984B1 - Phenylacetic acid derivatives, process and intermediates for producing them, fingicide, insecticide, arachnicide and nematocide compositions containing these compounds as active ingredients and use thereof - Google Patents

Info

Publication number

HU225984B1

HU225984B1 HU9802578A HUP9802578A HU225984B1 HU 225984 B1 HU225984 B1 HU 225984B1 HU 9802578 A HU9802578 A HU 9802578A HU P9802578 A HUP9802578 A HU P9802578A HU 225984 B1 HU225984 B1 HU 225984B1

Authority

HU

Hungary

Prior art keywords

compounds

formula

alkyl

always

moiety

Prior art date

1995-10-23

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• 150000001875 compounds Chemical class 0.000 title claims description 2091
• 239000004480 active ingredient Substances 0.000 title claims description 35
• 239000000203 mixture Substances 0.000 title claims description 26
• 238000000034 method Methods 0.000 title claims description 17
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims description 5
• 239000000543 intermediate Substances 0.000 title description 3
• 239000002917 insecticide Substances 0.000 title description 2
• 230000001069 nematicidal effect Effects 0.000 title 1
• 239000005645 nematicide Substances 0.000 title 1
• -1 methoxyimino, methoxymethylene Chemical group 0.000 claims description 735
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 350
• 125000000217 alkyl group Chemical group 0.000 claims description 81
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 241000233866 Fungi Species 0.000 claims description 14
• 241000607479 Yersinia pestis Species 0.000 claims description 14
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 14
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 12
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 12
• 241001465754 Metazoa Species 0.000 claims description 11
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 125000005110 aryl thio group Chemical group 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
• 239000000463 material Substances 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 241000244206 Nematoda Species 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
• 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 4
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 3
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
• 241000238631 Hexapoda Species 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
• 241000239223 Arachnida Species 0.000 claims description 2
• 239000000654 additive Substances 0.000 claims description 2
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
• 125000004122 cyclic group Chemical group 0.000 claims description 2
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
• 125000005367 heteroarylalkylthio group Chemical group 0.000 claims 1
• 230000000269 nucleophilic effect Effects 0.000 claims 1
• 101150065749 Churc1 gene Proteins 0.000 description 30
• 102100038239 Protein Churchill Human genes 0.000 description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 26
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 description 23
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 14
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 14
• 241000196324 Embryophyta Species 0.000 description 14
• 239000000243 solution Substances 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 13
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 13
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 13
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 13
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 13
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 13
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 13
• 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 12
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 12
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 12
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 12
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 12
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 12
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 12
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 12
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 12
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 12
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 12
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 12
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 12
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 12
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 12
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 12
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 12
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 12
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
• 238000006243 chemical reaction Methods 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 229910052757 nitrogen Chemical group 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 8
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
• 239000003995 emulsifying agent Substances 0.000 description 8
• 238000002844 melting Methods 0.000 description 8
• 230000008018 melting Effects 0.000 description 8
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 238000005481 NMR spectroscopy Methods 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 239000000417 fungicide Substances 0.000 description 7
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 125000004434 sulfur atom Chemical group 0.000 description 7
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000007921 spray Substances 0.000 description 6
• 239000011593 sulfur Chemical group 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
• 241000219094 Vitaceae Species 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 235000013339 cereals Nutrition 0.000 description 5
• 239000007795 chemical reaction product Substances 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 239000012990 dithiocarbamate Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 235000021021 grapes Nutrition 0.000 description 5
• 229920005610 lignin Polymers 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 229910052938 sodium sulfate Inorganic materials 0.000 description 5
• 235000011152 sodium sulphate Nutrition 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 125000004149 thio group Chemical group *S* 0.000 description 5
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 241000209140 Triticum Species 0.000 description 4
• 235000021307 Triticum Nutrition 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 238000011109 contamination Methods 0.000 description 4
• 239000002270 dispersing agent Substances 0.000 description 4
• 239000013583 drug formulation Substances 0.000 description 4
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 4
• 230000000855 fungicidal effect Effects 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
• 239000012044 organic layer Substances 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 239000006072 paste Substances 0.000 description 4
• 125000003367 polycyclic group Chemical group 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
• 235000013311 vegetables Nutrition 0.000 description 4
• 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 3
• 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 3
• 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• 208000031888 Mycoses Diseases 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
• 235000007164 Oryza sativa Nutrition 0.000 description 3
• 241001281803 Plasmopara viticola Species 0.000 description 3
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
• 235000012211 aluminium silicate Nutrition 0.000 description 3
• 239000002585 base Substances 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
• 229910052801 chlorine Inorganic materials 0.000 description 3
• 239000007859 condensation product Substances 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 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 3
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 238000004321 preservation Methods 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 235000009566 rice Nutrition 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• 239000011701 zinc Substances 0.000 description 3
• 229910052725 zinc Inorganic materials 0.000 description 3
• ZVJBPHMCBRHVEV-GQCTYLIASA-N (2e)-2-hydroxyiminopentan-3-one Chemical compound CCC(=O)C(\C)=N\O ZVJBPHMCBRHVEV-GQCTYLIASA-N 0.000 description 2
• NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• 235000000832 Ayote Nutrition 0.000 description 2
• 241001480061 Blumeria graminis Species 0.000 description 2
• 241000488564 Bryobia Species 0.000 description 2
• JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 241000254173 Coleoptera Species 0.000 description 2
• 241000219122 Cucurbita Species 0.000 description 2
• 235000009854 Cucurbita moschata Nutrition 0.000 description 2
• 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 2
• 241000489975 Diabrotica Species 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• 241000221785 Erysiphales Species 0.000 description 2
• 241001480224 Heterodera Species 0.000 description 2
• 241000379510 Heterodera schachtii Species 0.000 description 2
• 241000256602 Isoptera Species 0.000 description 2
• 241000255777 Lepidoptera Species 0.000 description 2
• 241000736227 Lucilia sericata Species 0.000 description 2
• 241001330975 Magnaporthe oryzae Species 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
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