UA75911C2 - AVERMECTINS SALTS SUBSITUTED IN POSITION 4ö HAVING PESTICIDE PROPERTIES - Google Patents

Info

Publication number

UA75911C2

UA75911C2 UA2003098799A UA2003098799A UA75911C2 UA 75911 C2 UA75911 C2 UA 75911C2 UA 2003098799 A UA2003098799 A UA 2003098799A UA 2003098799 A UA2003098799 A UA 2003098799A UA 75911 C2 UA75911 C2 UA 75911C2

Authority

UA

Ukraine

Prior art keywords

formula

acid

group

deoxy

compound

Prior art date

2001-02-27

Links

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• 150000003839 salts Chemical class 0.000 title abstract description 7
• 239000005660 Abamectin Substances 0.000 title description 24
• 239000000575 pesticide Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 abstract description 191
• 239000000203 mixture Substances 0.000 abstract description 68
• 150000001450 anions Chemical class 0.000 abstract description 66
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 49
• 229910052739 hydrogen Inorganic materials 0.000 abstract description 45
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 44
• 239000001257 hydrogen Substances 0.000 abstract description 40
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 26
• 238000000034 method Methods 0.000 abstract description 23
• 238000002360 preparation method Methods 0.000 abstract description 23
• 125000002947 alkylene group Chemical group 0.000 abstract description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
• 239000004480 active ingredient Substances 0.000 abstract description 3
• 230000008569 process Effects 0.000 abstract description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract description 2
• 230000000361 pesticidal effect Effects 0.000 abstract description 2
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 abstract 2
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 abstract 1
• 239000002253 acid Substances 0.000 description 113
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 98
• -1 benzyl- Chemical group 0.000 description 67
• 150000007513 acids Chemical class 0.000 description 64
• 239000002904 solvent Substances 0.000 description 63
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
• 241000196324 Embryophyta Species 0.000 description 41
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• 238000006243 chemical reaction Methods 0.000 description 37
• 239000013543 active substance Substances 0.000 description 33
• 235000019439 ethyl acetate Nutrition 0.000 description 33
• 229940093499 ethyl acetate Drugs 0.000 description 33
• IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 32
• 150000002431 hydrogen Chemical class 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 26
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
• 241000607479 Yersinia pestis Species 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
• 239000012071 phase Substances 0.000 description 23
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 19
• 150000002367 halogens Chemical class 0.000 description 19
• 125000001424 substituent group Chemical group 0.000 description 19
• 229910052736 halogen Inorganic materials 0.000 description 18
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
• 239000011734 sodium Substances 0.000 description 17
• 239000012074 organic phase Substances 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 238000004587 chromatography analysis Methods 0.000 description 15
• 241000244206 Nematoda Species 0.000 description 14
• 238000009835 boiling Methods 0.000 description 14
• 150000002170 ethers Chemical class 0.000 description 14
• 239000000741 silica gel Substances 0.000 description 14
• 229910002027 silica gel Inorganic materials 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 13
• 235000017557 sodium bicarbonate Nutrition 0.000 description 13
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• 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 12
• 125000003118 aryl group Chemical group 0.000 description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 12
• 241000269627 Amphiuma means Species 0.000 description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
• 240000001307 Myosotis scorpioides Species 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
• 229910052794 bromium Inorganic materials 0.000 description 10
• 229910052731 fluorine Inorganic materials 0.000 description 10
• 239000011737 fluorine Substances 0.000 description 10
• 229930195733 hydrocarbon Natural products 0.000 description 10
• 150000002430 hydrocarbons Chemical class 0.000 description 10
• 229910052708 sodium Inorganic materials 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 230000009471 action Effects 0.000 description 9
• 235000019441 ethanol Nutrition 0.000 description 9
• 239000011521 glass Substances 0.000 description 9
• 244000045947 parasite Species 0.000 description 9
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 239000000654 additive Substances 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 239000012141 concentrate Substances 0.000 description 8
• 235000008504 concentrate Nutrition 0.000 description 8
• 230000006378 damage Effects 0.000 description 8
• 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 8
• 150000008282 halocarbons Chemical class 0.000 description 8
• 125000000623 heterocyclic group Chemical group 0.000 description 8
• 238000005507 spraying Methods 0.000 description 8
• 239000004094 surface-active agent Substances 0.000 description 8
• 241001465754 Metazoa Species 0.000 description 7
• 239000002202 Polyethylene glycol Substances 0.000 description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 7
• 235000013601 eggs Nutrition 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 239000008187 granular material Substances 0.000 description 7
• 230000003993 interaction Effects 0.000 description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 229920001223 polyethylene glycol Polymers 0.000 description 7
• 235000002639 sodium chloride Nutrition 0.000 description 7
• 150000003462 sulfoxides Chemical class 0.000 description 7
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 239000003638 chemical reducing agent Substances 0.000 description 6
• 239000011248 coating agent Substances 0.000 description 6
• 238000000576 coating method Methods 0.000 description 6
• 229940093915 gynecological organic acid Drugs 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 150000007524 organic acids Chemical class 0.000 description 6
• 235000005985 organic acids Nutrition 0.000 description 6
• 125000004076 pyridyl group Chemical group 0.000 description 6
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
• 239000005995 Aluminium silicate Substances 0.000 description 5
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 5
• 241000238631 Hexapoda Species 0.000 description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
• 150000001298 alcohols Chemical class 0.000 description 5
• 125000001931 aliphatic group Chemical group 0.000 description 5
• 235000012211 aluminium silicate Nutrition 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
• 235000013399 edible fruits Nutrition 0.000 description 5
• 125000002541 furyl group Chemical group 0.000 description 5
• 125000001188 haloalkyl group Chemical group 0.000 description 5
• 150000007529 inorganic bases Chemical class 0.000 description 5
• 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 5
• 239000007788 liquid Substances 0.000 description 5
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 244000046052 Phaseolus vulgaris Species 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
• 150000001735 carboxylic acids Chemical class 0.000 description 4
• MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
• 230000001804 emulsifying effect Effects 0.000 description 4
• 125000002883 imidazolyl group Chemical group 0.000 description 4
• 125000001041 indolyl group Chemical group 0.000 description 4
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
• 244000144972 livestock Species 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
• 150000002825 nitriles Chemical class 0.000 description 4
• 239000003921 oil Substances 0.000 description 4
• 235000019198 oils Nutrition 0.000 description 4
• 125000003226 pyrazolyl group Chemical group 0.000 description 4
• 230000009467 reduction Effects 0.000 description 4
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
• 229960001860 salicylate Drugs 0.000 description 4
• 235000017550 sodium carbonate Nutrition 0.000 description 4
• 229940001593 sodium carbonate Drugs 0.000 description 4
• 125000000335 thiazolyl group Chemical group 0.000 description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 3
• 241000238876 Acari Species 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 239000005711 Benzoic acid Substances 0.000 description 3
• 240000007124 Brassica oleracea Species 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
• 241000282326 Felis catus Species 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 125000000217 alkyl group Chemical group 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 3
• 235000010233 benzoic acid Nutrition 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 150000001721 carbon Chemical group 0.000 description 3
• 125000001309 chloro group Chemical group Cl* 0.000 description 3
• 238000007865 diluting Methods 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• 238000001035 drying Methods 0.000 description 3
• 238000005516 engineering process Methods 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• 125000004995 haloalkylthio group Chemical group 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• 239000011976 maleic acid Substances 0.000 description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
• 239000000546 pharmaceutical excipient Substances 0.000 description 3
• 238000012545 processing Methods 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 229920005552 sodium lignosulfonate Polymers 0.000 description 3
• 239000002689 soil Substances 0.000 description 3
• 238000009331 sowing Methods 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
• BQMRHYBXRAYYQS-UHFFFAOYSA-N 4-dihydroxyphosphinothioyloxy-n,n-diethyl-6-methylpyrimidin-2-amine Chemical compound CCN(CC)C1=NC(C)=CC(OP(O)(O)=S)=N1 BQMRHYBXRAYYQS-UHFFFAOYSA-N 0.000 description 2
• OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 241000167854 Bourreria succulenta Species 0.000 description 2
• 235000002566 Capsicum Nutrition 0.000 description 2
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
• 235000005979 Citrus limon Nutrition 0.000 description 2
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