PT1638984E - Derivados monossacáridos de avermectina b1 - Google Patents

Info

Publication number

PT1638984E

PT1638984E PT04739912T PT04739912T PT1638984E PT 1638984 E PT1638984 E PT 1638984E PT 04739912 T PT04739912 T PT 04739912T PT 04739912 T PT04739912 T PT 04739912T PT 1638984 E PT1638984 E PT 1638984E

Authority

PT

Portugal

Prior art keywords

spp

alkyl

alkoxy

formula

phenyl

Prior art date

2003-06-16

Links

• Espacenet
• Global Dossier
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• NJTGMYOUKBELLQ-NVQQORPBSA-N avermectin b1 monosaccharide Chemical class O1C(C)C(O)C(OC)CC1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(C3)C=C[C@H](C)[C@@H](C(C)C)O2)C[C@@H]3OC(=O)[C@@H]([C@]23O)C=C(C)[C@@H](O)[C@H]3OC\C2=C/C=C/[C@@H]1C NJTGMYOUKBELLQ-NVQQORPBSA-N 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 210
• -1 C1 -C12 alkenyl Chemical group 0.000 claims description 126
• 239000000203 mixture Substances 0.000 claims description 92
• 125000004432 carbon atom Chemical group C* 0.000 claims description 64
• 238000000034 method Methods 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 27
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 27
• 238000002360 preparation method Methods 0.000 claims description 27
• 241000607479 Yersinia pestis Species 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• 125000004104 aryloxy group Chemical group 0.000 claims description 20
• 150000003839 salts Chemical group 0.000 claims description 19
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 17
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 15
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 14
• 241001465754 Metazoa Species 0.000 claims description 14
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 230000000361 pesticidal effect Effects 0.000 claims description 13
• 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 12
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 11
• 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
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 9
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
• 239000000463 material Substances 0.000 claims description 9
• 239000002671 adjuvant Substances 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
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 7
• 125000004450 alkenylene group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 5
• 238000002156 mixing Methods 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 125000001475 halogen functional group Chemical group 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
• 230000001902 propagating effect Effects 0.000 claims description 2
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
• 235000020094 liqueur Nutrition 0.000 claims 1
• 241000196324 Embryophyta Species 0.000 description 32
• 150000003254 radicals Chemical class 0.000 description 29
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• 239000000460 chlorine Substances 0.000 description 26
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• 230000000694 effects Effects 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
• 229910052794 bromium Inorganic materials 0.000 description 16
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
• 229910052801 chlorine Inorganic materials 0.000 description 15
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
• 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 14
• 239000000839 emulsion Substances 0.000 description 13
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
• 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 description 13
• 239000000243 solution Substances 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 239000005660 Abamectin Substances 0.000 description 11
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
• 239000002202 Polyethylene glycol Substances 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• 239000000654 additive Substances 0.000 description 9
• RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound 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 9
• 239000002585 base Substances 0.000 description 9
• 229920001223 polyethylene glycol Polymers 0.000 description 9
• 239000004094 surface-active agent Substances 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 8
• 239000011737 fluorine Substances 0.000 description 8
• 229910052731 fluorine Inorganic materials 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 241000244206 Nematoda Species 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
• 235000019441 ethanol Nutrition 0.000 description 7
• 239000008187 granular material Substances 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• 239000005995 Aluminium silicate Substances 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 241000238631 Hexapoda Species 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 240000001307 Myosotis scorpioides Species 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 235000012211 aluminium silicate Nutrition 0.000 description 6
• 239000012141 concentrate Substances 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 239000011630 iodine Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 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 6
• 239000000047 product Substances 0.000 description 6
• 241000238876 Acari Species 0.000 description 5
• 244000166124 Eucalyptus globulus Species 0.000 description 5
• 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 5
• 241000256250 Spodoptera littoralis Species 0.000 description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
• 239000004359 castor oil Substances 0.000 description 5
• 235000019438 castor oil Nutrition 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• 235000013399 edible fruits Nutrition 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
• 239000000575 pesticide Substances 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 241001558864 Aceria Species 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• 241000168038 Orthosia <moth> Species 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• 241000589516 Pseudomonas Species 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 240000008042 Zea mays Species 0.000 description 4
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
• 150000002170 ethers Chemical class 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 125000001188 haloalkyl group Chemical group 0.000 description 4
• 230000014759 maintenance of location Effects 0.000 description 4
• 229940098779 methanesulfonic acid Drugs 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 238000005507 spraying Methods 0.000 description 4
• QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 4
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
• 125000000335 thiazolyl group Chemical group 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
• 235000013162 Cocos nucifera Nutrition 0.000 description 3
• 244000060011 Cocos nucifera Species 0.000 description 3
• 244000068988 Glycine max Species 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
• 239000007832 Na2SO4 Substances 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 241000209094 Oryza Species 0.000 description 3
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• 244000046052 Phaseolus vulgaris Species 0.000 description 3
• 241000500437 Plutella xylostella Species 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 241001136852 Rhagoletis Species 0.000 description 3
• 241001486234 Sciota Species 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 241001414989 Thysanoptera Species 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 241001259047 Trichodectes Species 0.000 description 3
• 241000209140 Triticum Species 0.000 description 3
• 235000021307 Triticum Nutrition 0.000 description 3
• 230000000895 acaricidal effect Effects 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
• 125000004429 atom Chemical group 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
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 235000013339 cereals Nutrition 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 239000011248 coating agent Substances 0.000 description 3
• 238000000576 coating method Methods 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
• 238000010790 dilution Methods 0.000 description 3
• 239000012895 dilution Substances 0.000 description 3
• 235000013601 eggs Nutrition 0.000 description 3
• 238000011156 evaluation Methods 0.000 description 3
• 150000004665 fatty acids Chemical class 0.000 description 3
• DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 3
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound 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
• 125000002541 furyl group Chemical group 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 150000002772 monosaccharides Chemical class 0.000 description 3
• 125000001624 naphthyl group Chemical group 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
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• 229920003023 plastic Polymers 0.000 description 3
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• 125000004076 pyridyl group Chemical group 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
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