JP2005532367A - ピラゾールカルボキサミド殺虫剤 - Google Patents
ピラゾールカルボキサミド殺虫剤 Download PDFInfo
- Publication number
- JP2005532367A JP2005532367A JP2004513260A JP2004513260A JP2005532367A JP 2005532367 A JP2005532367 A JP 2005532367A JP 2004513260 A JP2004513260 A JP 2004513260A JP 2004513260 A JP2004513260 A JP 2004513260A JP 2005532367 A JP2005532367 A JP 2005532367A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkyl
- formula
- group
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002917 insecticide Substances 0.000 title description 6
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 239000000203 mixture Substances 0.000 claims abstract description 79
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000007787 solid Substances 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims abstract description 21
- 239000003085 diluting agent Substances 0.000 claims abstract description 19
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 17
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 14
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 12
- 239000004094 surface-active agent Substances 0.000 claims abstract description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- -1 C 1 -C 4 alkylthio Chemical group 0.000 claims description 66
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000006315 carbonylation Effects 0.000 claims description 3
- 238000005810 carbonylation reaction Methods 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- 239000000126 substance Substances 0.000 abstract description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000012360 testing method Methods 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 241000254173 Coleoptera Species 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 241000238631 Hexapoda Species 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 241001124076 Aphididae Species 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 230000006378 damage Effects 0.000 description 11
- 241000238876 Acari Species 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000008187 granular material Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 235000005911 diet Nutrition 0.000 description 8
- 230000037213 diet Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- 0 Cc1ccnc(*)c1 Chemical compound Cc1ccnc(*)c1 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 241001674048 Phthiraptera Species 0.000 description 7
- 241000254062 Scarabaeidae Species 0.000 description 7
- 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 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000011550 stock solution Substances 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000239290 Araneae Species 0.000 description 6
- 241000193388 Bacillus thuringiensis Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 6
- 229940097012 bacillus thuringiensis Drugs 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 239000005660 Abamectin Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 241000258937 Hemiptera Species 0.000 description 5
- 241000255777 Lepidoptera Species 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical group OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 241000237858 Gastropoda Species 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 241000256247 Spodoptera exigua Species 0.000 description 4
- 241000256251 Spodoptera frugiperda Species 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000000642 acaricide Substances 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 230000000967 entomopathogenic effect Effects 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000021 stimulant Substances 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 3
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 3
- XHZWFUVEKDDQPF-UHFFFAOYSA-N 5-bromo-1h-pyrazole Chemical compound BrC1=CC=NN1 XHZWFUVEKDDQPF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000238421 Arthropoda Species 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 239000005884 Beta-Cyfluthrin Substances 0.000 description 3
- 239000005895 Esfenvalerate Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005899 Fipronil Substances 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 241000578422 Graphosoma lineatum Species 0.000 description 3
- 241001147381 Helicoverpa armigera Species 0.000 description 3
- 241000256244 Heliothis virescens Species 0.000 description 3
- 239000005906 Imidacloprid Substances 0.000 description 3
- 239000005907 Indoxacarb Substances 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000005950 Oxamyl Substances 0.000 description 3
- 241000255969 Pieris brassicae Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000005925 Pymetrozine Substances 0.000 description 3
- 241001454295 Tetranychidae Species 0.000 description 3
- 239000005940 Thiacloprid Substances 0.000 description 3
- 241001414989 Thysanoptera Species 0.000 description 3
- 241000256856 Vespidae Species 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 241000209149 Zea Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 description 3
- 229950008167 abamectin Drugs 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 150000003927 aminopyridines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 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 3
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 3
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229940013764 fipronil Drugs 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 229940056881 imidacloprid Drugs 0.000 description 3
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 3
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000005645 nematicide Substances 0.000 description 3
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 235000001508 sulfur Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 108700012359 toxins Proteins 0.000 description 3
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 description 2
- WJUKOGPNGRUXMG-UHFFFAOYSA-N 1,2-dibromo-1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)(Br)C(Cl)(Cl)Br WJUKOGPNGRUXMG-UHFFFAOYSA-N 0.000 description 2
- CCXJCKFHRYPKEP-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl CCXJCKFHRYPKEP-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- FORBXGROTPOMEH-UHFFFAOYSA-N 5-bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl FORBXGROTPOMEH-UHFFFAOYSA-N 0.000 description 2
- SICJSQIIOGHYJD-UHFFFAOYSA-N 5-bromo-n-(2-bromo-4,6-difluorophenyl)-2-(3-chloropyridin-2-yl)pyrazole-3-carboxamide Chemical compound BrC1=CC(F)=CC(F)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl SICJSQIIOGHYJD-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241001259789 Amyelois transitella Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 108700003918 Bacillus Thuringiensis insecticidal crystal Proteins 0.000 description 2
- 241001302798 Bemisia argentifolii Species 0.000 description 2
- 241000254127 Bemisia tabaci Species 0.000 description 2
- 241001631693 Blattella asahinai Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000282465 Canis Species 0.000 description 2
- 241000242722 Cestoda Species 0.000 description 2
- 241000258920 Chilopoda Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 241001124134 Chrysomelidae Species 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 241001414720 Cicadellidae Species 0.000 description 2
- 241001672694 Citrus reticulata Species 0.000 description 2
- 239000005888 Clothianidin Substances 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 241000254171 Curculionidae Species 0.000 description 2
- 239000005946 Cypermethrin Substances 0.000 description 2
- 241000586568 Diaspidiotus perniciosus Species 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001057636 Dracaena deremensis Species 0.000 description 2
- 239000005894 Emamectin Substances 0.000 description 2
- 241000995027 Empoasca fabae Species 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 241000917107 Eriosoma lanigerum Species 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000894055 Haematopinus eurysternus Species 0.000 description 2
- 241000255967 Helicoverpa zea Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000238681 Ixodes Species 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000243785 Meloidogyne javanica Species 0.000 description 2
- 239000005916 Methomyl Substances 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000084931 Neohydatothrips variabilis Species 0.000 description 2
- 241001671709 Nezara viridula Species 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- 241001012098 Omiodes indicata Species 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 241000721451 Pectinophora gossypiella Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 241000256682 Peregrinus maidis Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241000286209 Phasianidae Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241001516577 Phylloxera Species 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 239000005927 Pyriproxyfen Substances 0.000 description 2
- 235000014443 Pyrus communis Nutrition 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 241000167882 Rhopalosiphum maidis Species 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- 241001510236 Rhyparobia maderae Species 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 241000256011 Sphingidae Species 0.000 description 2
- 239000005930 Spinosad Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000270666 Testudines Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000244030 Toxocara canis Species 0.000 description 2
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 2
- 241000255993 Trichoplusia ni Species 0.000 description 2
- 239000005942 Triflumuron Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 244000274883 Urtica dioica Species 0.000 description 2
- 235000009108 Urtica dioica Nutrition 0.000 description 2
- 241001248766 Zonocyba pomaria Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001298 alcohols Polymers 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229960002587 amitraz Drugs 0.000 description 2
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000005667 attractant Substances 0.000 description 2
- 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 2
- 239000003124 biologic agent Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229960001591 cyfluthrin Drugs 0.000 description 2
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 2
- 229960005424 cypermethrin Drugs 0.000 description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin 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](NC)[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 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 2
- 239000002871 fertility agent Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008202 granule composition Substances 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000000232 haloalkynyl group Chemical group 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006263 metalation reaction Methods 0.000 description 2
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- YCMHUZBMXRJVBM-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound CC1=CC=CC(Cl)=C1NC(=O)C1=CC(C(F)(F)F)=NN1C1=NC=CC=C1Cl YCMHUZBMXRJVBM-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000003016 pheromone Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000005180 public health Effects 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 229940014213 spinosad Drugs 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- LZTIMERBDGGAJD-SNAWJCMRSA-N (2e)-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)\C=C1/NCCCS1 LZTIMERBDGGAJD-SNAWJCMRSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 1
- SOUGWDPPRBKJEX-AWEZNQCLSA-N (S)-zoxamide Chemical compound ClCC(=O)[C@](C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-AWEZNQCLSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- FBTQQNYGMICJQZ-UHFFFAOYSA-N 1-chloro-2-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1N=C=O FBTQQNYGMICJQZ-UHFFFAOYSA-N 0.000 description 1
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- LSJVQKDTVCDSPE-UHFFFAOYSA-N 1h-pyrazole-5-sulfonamide Chemical compound NS(=O)(=O)C=1C=CNN=1 LSJVQKDTVCDSPE-UHFFFAOYSA-N 0.000 description 1
- MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- IYPAPRRNUCGNKP-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-n-(2,4-dichlorophenyl)-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound N=1C=CC=C(Cl)C=1N1N=C(C(F)(F)F)C=C1C(=O)NC1=CC=C(Cl)C=C1Cl IYPAPRRNUCGNKP-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 description 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- XXTPHXNBKRVYJI-UHFFFAOYSA-N 2-pyrazol-1-ylpyridine Chemical compound C1=CC=NN1C1=CC=CC=N1 XXTPHXNBKRVYJI-UHFFFAOYSA-N 0.000 description 1
- NWPHYUJSBUUVRT-UHFFFAOYSA-N 3,4-dimethylpyrazole-1-sulfonamide Chemical compound CC1=CN(S(N)(=O)=O)N=C1C NWPHYUJSBUUVRT-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PYBWMCRVFDXECL-UHFFFAOYSA-N 3-bromo-n,n-dimethylpyrazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=CC(Br)=N1 PYBWMCRVFDXECL-UHFFFAOYSA-N 0.000 description 1
- IADZROUQPRNNNZ-UHFFFAOYSA-N 3-chloro-2-[3-(trifluoromethyl)pyrazol-1-yl]pyridine Chemical compound N1=C(C(F)(F)F)C=CN1C1=NC=CC=C1Cl IADZROUQPRNNNZ-UHFFFAOYSA-N 0.000 description 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- RZJPBQGRCNJYBU-UHFFFAOYSA-N 3-chloropyridin-2-amine Chemical compound NC1=NC=CC=C1Cl RZJPBQGRCNJYBU-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000132121 Acaridae Species 0.000 description 1
- 206010063409 Acarodermatitis Diseases 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241001516607 Adelges Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000059559 Agriotes sordidus Species 0.000 description 1
- 241000566547 Agrotis ipsilon Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 235000008553 Allium fistulosum Nutrition 0.000 description 1
- 244000257727 Allium fistulosum Species 0.000 description 1
- 241000902876 Alticini Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238679 Amblyomma Species 0.000 description 1
- 241000238682 Amblyomma americanum Species 0.000 description 1
- 241000242266 Amphimallon majalis Species 0.000 description 1
- 241000663922 Anasa tristis Species 0.000 description 1
- 241000415078 Anemone hepatica Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241001600407 Aphis <genus> Species 0.000 description 1
- 241001151957 Aphis aurantii Species 0.000 description 1
- 241000271857 Aphis citricidus Species 0.000 description 1
- 241000952611 Aphis craccivora Species 0.000 description 1
- 241000273311 Aphis spiraecola Species 0.000 description 1
- 241000256837 Apidae Species 0.000 description 1
- 241001002469 Archips Species 0.000 description 1
- 241001002470 Archips argyrospila Species 0.000 description 1
- 241001423656 Archips rosana Species 0.000 description 1
- 241000244185 Ascaris lumbricoides Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- 241000701412 Baculoviridae Species 0.000 description 1
- 239000005874 Bifenthrin Substances 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000929635 Blissus Species 0.000 description 1
- 239000005739 Bordeaux mixture Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241001113967 Bovicola ovis Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 241001643374 Brevipalpus Species 0.000 description 1
- 241001034435 Brevipalpus obovatus Species 0.000 description 1
- 241001455939 Brissus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001414201 Bruchus pisorum Species 0.000 description 1
- 241001388466 Bruchus rufimanus Species 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 241001425384 Cacopsylla pyricola Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000722666 Camponotus Species 0.000 description 1
- 241001491934 Camponotus pennsylvanicus Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 241000252229 Carassius auratus Species 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 244000068645 Carya illinoensis Species 0.000 description 1
- 235000009025 Carya illinoensis Nutrition 0.000 description 1
- 241001166141 Chelisoches Species 0.000 description 1
- 241001166081 Chelisoches morio Species 0.000 description 1
- 241000606069 Chlamydiaceae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000191839 Chrysomya Species 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 102100032392 Circadian-associated transcriptional repressor Human genes 0.000 description 1
- 101710130150 Circadian-associated transcriptional repressor Proteins 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- MKORXOPACGNFQO-UHFFFAOYSA-N ClC1=NC=CC=C1Cl.BrC1=NN(C=C1)C1=NC=CC=C1Cl Chemical compound ClC1=NC=CC=C1Cl.BrC1=NN(C=C1)C1=NC=CC=C1Cl MKORXOPACGNFQO-UHFFFAOYSA-N 0.000 description 1
- 241000909969 Clambus Species 0.000 description 1
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 1
- 241001340508 Crambus Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- 239000005891 Cyromazine Substances 0.000 description 1
- 241000283323 Delphinapterus leucas Species 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 241001480793 Dermacentor variabilis Species 0.000 description 1
- 241001124144 Dermaptera Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241001205778 Dialeurodes citri Species 0.000 description 1
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 239000005762 Dimoxystrobin Substances 0.000 description 1
- 241000258963 Diplopoda Species 0.000 description 1
- 241000243988 Dirofilaria immitis Species 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- 241001581006 Dysaphis plantaginea Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241001572697 Earias vittella Species 0.000 description 1
- 241001549209 Echidnophaga gallinacea Species 0.000 description 1
- 241000995023 Empoasca Species 0.000 description 1
- 241001555556 Ephestia elutella Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- 241001515686 Erythroneura Species 0.000 description 1
- 239000005897 Etoxazole Substances 0.000 description 1
- 235000006647 Eugenia jambos Nutrition 0.000 description 1
- 241001619920 Euschistus servus Species 0.000 description 1
- 239000005772 Famoxadone Substances 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 239000005774 Fenamidone Substances 0.000 description 1
- 239000005775 Fenbuconazole Substances 0.000 description 1
- 239000005777 Fenpropidin Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000005657 Fenpyroximate Substances 0.000 description 1
- 239000005900 Flonicamid Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- 239000005785 Fluquinconazole Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 241000720914 Forficula auricularia Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000027294 Fusi Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 241000257232 Haematobia irritans Species 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
- 241001000403 Herpetogramma licarsisalis Species 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241001058149 Icerya Species 0.000 description 1
- 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 1
- 239000005796 Ipconazole Substances 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 241001638457 Lasius alienus Species 0.000 description 1
- 241000238866 Latrodectus mactans Species 0.000 description 1
- 241000500881 Lepisma Species 0.000 description 1
- 241000661779 Leptoglossus Species 0.000 description 1
- 241000683448 Limonius Species 0.000 description 1
- 241000272317 Lipaphis erysimi Species 0.000 description 1
- 241001261104 Lobesia botrana Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241000238864 Loxosceles Species 0.000 description 1
- 241000131091 Lucanus cervus Species 0.000 description 1
- 241000920471 Lucilia caesar Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001280337 Lycosidae Species 0.000 description 1
- 241000258912 Lygaeidae Species 0.000 description 1
- 241000501345 Lygus lineolaris Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241000922538 Melanoplus sanguinipes Species 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000180212 Metopolophium Species 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 241000238745 Musca autumnalis Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 241000133263 Nasonovia ribisnigri Species 0.000 description 1
- 241000359016 Nephotettix Species 0.000 description 1
- 241000615716 Nephotettix nigropictus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001446843 Oebalus pugnax Species 0.000 description 1
- 241000258913 Oncopeltus fasciatus Species 0.000 description 1
- 241000975417 Oscinella frit Species 0.000 description 1
- 241001147397 Ostrinia Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241000935974 Paralichthys dentatus Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000517307 Pediculus humanus Species 0.000 description 1
- 241000517306 Pediculus humanus corporis Species 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- 241000048273 Periplaneta japonica Species 0.000 description 1
- 235000003823 Petasites japonicus Nutrition 0.000 description 1
- 240000003296 Petasites japonicus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000907661 Pieris rapae Species 0.000 description 1
- 239000005923 Pirimicarb Substances 0.000 description 1
- 241000219843 Pisum Species 0.000 description 1
- 241000691880 Planococcus citri Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000005821 Propamocarb Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241000722234 Pseudococcus Species 0.000 description 1
- 241001414857 Psyllidae Species 0.000 description 1
- 241000718000 Pulex irritans Species 0.000 description 1
- 239000005869 Pyraclostrobin Substances 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005926 Pyridalyl Substances 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241001509967 Reticulitermes flavipes Species 0.000 description 1
- 241001152954 Reticulitermes hesperus Species 0.000 description 1
- 241001620634 Roger Species 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000277331 Salmonidae Species 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000447727 Scabies Species 0.000 description 1
- 241000722027 Schizaphis graminum Species 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000180219 Sitobion avenae Species 0.000 description 1
- 241000254152 Sitophilus oryzae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000176086 Sogatella furcifera Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 239000005837 Spiroxamine Substances 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000122938 Strongylus vulgaris Species 0.000 description 1
- 244000087016 Syzygium jambos Species 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241001157792 Tapinoma Species 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005937 Tebufenozide Substances 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241000270708 Testudinidae Species 0.000 description 1
- 239000005840 Tetraconazole Substances 0.000 description 1
- 241001374808 Tetramorium caespitum Species 0.000 description 1
- 241000488577 Tetranychus mcdanieli Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000289813 Therioaphis trifolii Species 0.000 description 1
- 241000028626 Thermobia domestica Species 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 241000339374 Thrips tabaci Species 0.000 description 1
- 241000212886 Thunnus atlanticus Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 239000005848 Tribasic copper sulfate Substances 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 241001414858 Trioza Species 0.000 description 1
- 239000005859 Triticonazole Substances 0.000 description 1
- 241000722921 Tulipa gesneriana Species 0.000 description 1
- 241001389006 Tuta absoluta Species 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 235000011862 Vitis cinerea Nutrition 0.000 description 1
- 244000272739 Vitis cinerea Species 0.000 description 1
- 241000908413 Wasmannia Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- CGIHPACLZJDCBQ-UHFFFAOYSA-N acibenzolar Chemical compound SC(=O)C1=CC=CC2=C1SN=N2 CGIHPACLZJDCBQ-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- 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 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-UHFFFAOYSA-N blasticidin-S Natural products O1C(C(O)=O)C(NC(=O)CC(N)CCN(C)C(N)=N)C=CC1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 235000001436 butterbur Nutrition 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- RXDMAYSSBPYBFW-PKFCDNJMSA-N carpropamide Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(=O)[C@@]1(CC)[C@H](C)C1(Cl)Cl RXDMAYSSBPYBFW-PKFCDNJMSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 description 1
- 229950000775 cyromazine Drugs 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 1
- 150000004844 dioxiranes Chemical class 0.000 description 1
- 229940099686 dirofilaria immitis Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 238000007350 electrophilic reaction Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000004634 feeding behavior Effects 0.000 description 1
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229940014144 folate Drugs 0.000 description 1
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 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 1
- 150000002334 glycols Chemical class 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000005347 halocycloalkyl group Chemical group 0.000 description 1
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 208000028454 lice infestation Diseases 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007758 mating behavior Effects 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- QYPPRTNMGCREIM-UHFFFAOYSA-M methylarsonate(1-) Chemical compound C[As](O)([O-])=O QYPPRTNMGCREIM-UHFFFAOYSA-M 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- RFYSRCRZAGKOIY-UHFFFAOYSA-N n,n-dimethylpyrazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=CC=N1 RFYSRCRZAGKOIY-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WMZYZYFPPQOFKY-UHFFFAOYSA-N n-phenyl-1h-pyrazole-3-carboxamide Chemical class C1=CNN=C1C(=O)NC1=CC=CC=C1 WMZYZYFPPQOFKY-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000010653 organometallic reaction Methods 0.000 description 1
- 238000007122 ortho-metalation reaction Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 239000002675 polymer-supported reagent Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- NWUWYYSKZYIQAE-LBAUFKAWSA-N propan-2-yl n-[3-methyl-1-[[(1s)-1-(4-methylphenyl)ethyl]amino]-1-oxobutan-2-yl]carbamate Chemical compound CC(C)OC(=O)NC(C(C)C)C(=O)N[C@@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-LBAUFKAWSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 231100000654 protein toxin Toxicity 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
【化1】
[式中、AはOまたはSであり、Bは1〜5個のR2によって各環が場合により置換されていてもよいフェニル環またはピリジン環であり、Jが本明細書に定義されるようなピラゾールまたはピロール複素環式環系であり、そしてR1はH、あるいはそれぞれ場合によりハロゲン、CN、NO2、ヒドロキシ、C1〜C4アルコキシ、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C2〜C4アルコキシカルボニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノおよびC3〜C6シクロアルキルアミノよりなる群から選択される1個もしくはそれ以上の置換基によって置換されていてもよいC1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニルまたはC3〜C6シクロアルキルである]の化合物、そのN−オキシドおよび塩を提供する。無脊椎有害生物またはその環境を、少なくとも1種の式Iの化合物、そのN−オキシドまたは塩(例えば、本明細書に記載の組成物として)の生物学的に有効な量と接触させることを含んでなる少なくとも1種の無脊椎有害生物の防除方法も開示する。また本発明は、少なくとも1種の式Iの化合物、そのN−オキシドまたは塩、ならびに界面活性剤、固体希釈剤および液体希釈剤よりなる群から選択される少なくとも1種の追加成分を含んでなる組成物に関する。
Description
AはOまたはSであり、
Bは1〜5個のR2によって各環が置換されているフェニル環またはピリジン環であり、
JがJ−1、J−2、J−3、J−4、J−5およびJ−6よりなる群から選択されるピラゾールまたはピロール複素環式環系であり、
R1はC2〜C6アルキルカルボニル、C2〜C6アルコキシカルボニル、C2〜C6アルキルアミノカルボニルまたはC3〜C8ジアルキルアミノカルボニルであり、
各R2は独立してH、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C3〜C6シクロアルキル、C1〜C6ハロアルキル、C2〜C6ハロアルケニル、C2〜C6ハロアルキニル、C3〜C6ハロシクロアルキル、C2〜C4シアノアルキル、ハロゲン、CN、NO2、ピペリジン、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4ハロアルキルチオ、C1〜C4ハロアルキルスルフィニル、C1〜C4ハロアルキルスルホニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノおよびC3〜C6シクロアルキルアミノよりなる群から選択されるか、あるいは
各R2は独立して各環が場合によりC1〜C4アルキル、C2〜C4アルケニル、C2〜C4アルキニル、C3〜C6シクロアルキル、C1〜C4ハロアルキル、C2〜C4ハロアルケニル、C2〜C4ハロアルキニル、C3〜C6ハロシクロアルキル、ハロゲン、CN、NO2、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノ、C3〜C6シクロアルキルアミノ、C4〜C7(アルキル)シクロアルキルアミノ、C2〜C6アルコキシカルボニル、C2〜C6アルキルアミノカルボニルおよびC3〜C8ジアルキルアミノカルボニルよりなる群から選択される1個もしくはそれ以上の置換基によって置換されていてもよいフェニル、ベンジルまたはフェノキシ環よりなる群から選択され、
R5は
各R6、R6aおよびR7は独立してH、C1〜C6アルキル、C3〜C6シクロアルキル、C1〜C6ハロアルキル、ハロゲン、CN、C1〜C4アルコキシ、C1〜C4アルキルチオ、C1〜C4ハロアルコキシおよびC1〜C4ハロアルキルチオよりなる群から選択され、そして
R8はH、C1〜C6アルキル、C1〜C6ハロアルキル、C3〜C6アルケニル、C3〜C6ハロアルケニル、C3〜C6アルキニル、C3〜C6ハロアルキニルまたはC1〜C4ハロアルコキシである]
AはOまたはSであり、
Bは1〜5個のR2によって各環が置換されているフェニル環またはピリジン環であり、
JがJ−1、J−2、J−3、J−4、J−5およびJ−6よりなる群から選択されるピラゾールまたはピロール複素環式環系であり、
R1はC2〜C6アルキルカルボニル、C2〜C6アルコキシカルボニル、C2〜C6アルキルアミノカルボニルまたはC3〜C8ジアルキルアミノカルボニルであり、
各R2は独立してH、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C3〜C6シクロアルキル、C1〜C6ハロアルキル、C2〜C6ハロアルケニル、C2〜C6ハロアルキニル、C3〜C6ハロシクロアルキル、C2〜C4シアノアルキル、ハロゲン、CN、NO2、ピペリジン、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C2〜C4アルコキシカルボニル、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4ハロアルキルチオ、C1〜C4ハロアルキルスルフィニル、C1〜C4ハロアルキルスルホニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノおよびC3〜C6シクロアルキルアミノよりなる群から選択されるか、あるいは
各R2は独立して各環が場合によりC1〜C4アルキル、C2〜C4アルケニル、C2〜C4アルキニル、C3〜C6シクロアルキル、C1〜C4ハロアルキル、C2〜C4ハロアルケニル、C2〜C4ハロアルキニル、C3〜C6ハロシクロアルキル、ハロゲン、CN、NO2、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノ、C3〜C6シクロアルキルアミノ、C4〜C7(アルキル)シクロアルキルアミノ、C2〜C6アルコキシカルボニル、C2〜C6アルキルアミノカルボニルおよびC3〜C8ジアルキルアミノカルボニルよりなる群から選択される1個もしくはそれ以上の置換基によって置換されていてもよいフェニル、ベンジルまたはフェノキシ環よりなる群から選択され、
R5は
各R6およびR7は独立してH、C1〜C6アルキル、C3〜C6シクロアルキル、C1〜C6ハロアルキル、ハロゲン、CN、C1〜C4アルコキシ、C1〜C4アルキルチオ、C1〜C4ハロアルコキシおよびC1〜C4ハロアルキルチオよりなる群から選択され、そして
R8はH、C1〜C6アルキル、C1〜C6ハロアルキル、C3〜C6アルケニル、C3〜C6ハロアルケニル、C3〜C6アルキニル、C3〜C6ハロアルキニルまたはC1〜C4ハロアルコキシである、式Iの化合物である。
好ましい1.JがJ−1、J−2、J−3またはJ−6である、上記式Iの化合物、ならびにそのN−オキシドおよび塩。
R1がHであり、
1〜3個のR2基がH以外であり、かつ独立してC1〜C6アルキル、C1〜C6ハロアルキル、C2〜C4シアノアルキル、ハロゲン、CN、NO2、ピペリジン、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C2〜C4アルコキシカルボニル、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4ハロアルキルチオ、C1〜C4ハロアルキルスルフィニルおよびC1〜C4ハロアルキルスルホニルよりなる群から選択され、そして
直前に記載の少なくとも1個のR2がNR1C(=A)J部分に対してオルトにある、好ましい1の化合物。
R7がH、CH3、CF3、CH2CF3、CHF2、OCH2CF3、OCHF2またはハロゲンである、好ましい2の化合物。
R6がClまたはBrであり、そして
R7がハロゲン、OCH2CF3、OCHF2またはCF3である、好ましい4の化合物。
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である、好ましい4の化合物。
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である、好ましい4の化合物。
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である、好ましい4の化合物。
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である、好ましい4の化合物。
N−(2−クロロ−6−メチルフェニル)−1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミドの調製
工程A:3−クロロ−2−[3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ピリジンの調製
乾燥N,N−ジメチルホルムアミド(300mL)中2,3−ジクロロピリジン(99.0g、0.67モル)および3−(トリフルオロメチル)ピラゾール(83g、0.61モル)の混合物に、炭酸カリウム(166.0g、1.2モル)を添加し、次いで48時間かけて反応を110〜125℃まで加熱した。反応を100℃まで冷却し、そしてセライト(Celite)(登録商標)珪藻土フィルターエイドを通して濾過し、固体を除去した。周囲圧力での蒸留によって、N,N−ジメチルホルムアミドおよび過剰量のジクロロピリジンを除去した。減圧下での生成物の蒸留(b.p.139〜141℃、7mm)によって、透明黄色油状物として表題の化合物を得た(113.4g)。
1H NMR(CDCl3):δ6.78(s,1H)、7.36(t,1H)、7.93(d,1H)、8.15(s,1H)、8.45(d,1H)
−75℃の乾燥テトラヒドロフラン(700mL)中3−クロロ−2−[3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ピリジン(すなわち、工程Aからのピラゾール生成物)(105.0g、425ミリモル)の溶液に、カニューレを通して、乾燥テトラヒドロフラン(300mL)中リチウムジイソプロピルアミド(425ミリモル)の−30℃溶液を添加した。深紅色溶液を15分間撹拌し、その後、溶液が淡黄色になって、そして発熱が停止するまで、−63℃で溶液中に二酸化炭素をバブリングした。反応をさらに20分間撹拌し、次いで水(20mL)でクエンチングした。溶媒を減圧下で除去し、そして反応混合物を、エーテルと0.5N水酸化ナトリウム水溶液との間で分配した。水性抽出物をエーテル(3×)で洗浄し、セライト(Celite)(登録商標)珪藻土フィルターエイドを通して濾過し、残渣固体を除去し、次いで、オレンジ色油状物が形成する約4のpHまで酸性化した。水性混合物を強力に撹拌し、そして2.5〜3までpHを低下させるために、さらに酸を添加した。オレンジ色油状物は顆粒状固体へと凝固し、これを濾過し、水と1N塩酸とで連続的に洗浄し、そして真空下50℃で乾燥させ、オフホワイト色固体として表題の生成物を得た(130g)。(類似手順に従うもう1回の実行からの生成物は、175〜176℃で融解した。)
1H NMR(CDCl3):δ7.61(s,1H)、7.76(dd,1H)、8.31(d,1H)、8.60(d,1H)
テトラヒドロフラン(50ml)中3−クロロ−2−[3−(トリフルオロメチル)−1H−ピラゾール−1−イル]ピリジン(すなわち、工程Aからのピラゾール生成物)(2.72g、11.14ミリモル)の溶液を−70℃まで冷却した。リチウムジイソプロピルアミン(THF/ヘプタン中2M、5.5mL、11.0ミリモル)を2分かけて添加し、そして混合物を15分間撹拌した。2−クロロ−6−メチルフェニルイソシアネート(1.90g、11.33ミリモル)をシリンジを介して添加した。混合物を20℃まで加温させ、そして塩化アンモニウムの飽和水溶液(50mL)でクエンチングした。反応生成量を酢酸エチル(100mL)で抽出し、硫酸マグネシウム上で乾燥させ、そして濃縮した。3:1ヘキサン/酢酸エチルから1:1ヘキサン/酢酸エチルの勾配によるシリカゲル上クロマトグラフィによって、212〜213℃で融解する固体として、本発明の化合物である表題の化合物を得た(3.0g)。
1H NMR(CDCl3):δ2.24(3H)、7.1(1H)、7.2(1H)、7.25(1H)、7.4(1H)、7.6(1H)、7.9(1H)、8.5(1H)
N−(2−ブロモ−4,6−ジフルオロフェニル)−1−(3−クロロ−2−ピリジニル)−3−ブロモ−1H−ピラゾール−5−カルボキサミドの調製
工程A:3−ブロモ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミドの調製
−78℃の乾燥テトラヒドロフラン(500mL)中N−ジメチルスルファモイルピラゾール(44.0g、0.251モル)の溶液に、温度を−60℃未満に保持しながら、n−ブチルリチウムの溶液(ヘキサン中2.5M、105.5mL、0.264モル)を滴下して添加した。添加の間、厚みのある固体が形成した。添加完了時に、反応混合物をさらに15分間保持し、その後、温度を−70℃未満に保持しながら、テトラヒドロフラン(150mL)中1,2−ジブロモ−テトラクロロエタン(90g、0.276モル)の溶液を滴下して添加した。反応混合物は透明オレンジ色に変化し、撹拌をさらに15分間継続した。−78℃浴を取り外し、そして反応を水(600mL)でクエンチングした。反応混合物を塩化メチレン(4×)で抽出し、そして有機抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮した。溶出剤として塩化メチレン−ヘキサン(50:50)を使用して、シリカゲル上クロマトグラフィによって粗製生成物をさらに精製し、透明無色油状物として表題の生成物を得た(57.04g)。
1H NMR(CDCl3):δ3.07(d,6H)、6.44(m,1H)、7.62(m,1H)
トリフルオロ酢酸(70mL)に、3−ブロモ−N,N−ジメチル−1H−ピラゾール−1−スルホンアミド(すなわち、工程Aのブロモピラゾール生成物)(57.04g)をゆっくり添加した。反応混合物を30分間、室温で撹拌し、次いで減圧下で濃縮した。残渣をヘキサン中に溶解し、不溶性固体を濾過して除去し、そしてヘキサンをエバポレーションして、油状物として粗製生成物を得た。溶出剤として酢酸エチル/ジクロロメタン(10:90)を使用して、シリカゲル上クロマトグラフィによって粗製生成物をさらに精製し、油状物を得た。油状物をジクロロメタン中に溶解し、重炭酸ナトリウム水溶液で中和し、塩化メチレン(3×)で抽出し、硫酸マグネシウム上で乾燥させて、そして濃縮し、白色固体として表題の生成物を得た(25.9g)。融点(m.p.)61〜64℃。
1H NMR(CDCl3):δ6.37(d,1H)、7.59(d,1H)、12.4(br s,1H)
乾燥N,N−ジメチルホルムアミド(88mL)中2,3−ジクロロピリジン(27.4g、185ミリモル)および3−ブロモピラゾール(すなわち、工程Bの生成物)(25.4g、176ミリモル)の混合物に、炭酸カリウム(48.6g、352ミリモル)を添加し、そして反応混合物を18時間、125℃まで加熱した。反応混合物を室温まで冷却し、そして氷水(800mL)中に注入した。沈殿が形成した。沈殿した固体を1.5時間撹拌し、濾過し、そして水(2×100mL)で洗浄した。固体濾過ケーキを塩化メチレン中に溶解し、そして連続的に水、1N塩酸、飽和重炭酸ナトリウム水溶液およびブラインで洗浄した。次いで、有機抽出物を硫酸マグネシウム上で乾燥させ、そして濃縮し、39.9gのピンク色固体を得た。粗製固体をヘキサン中に懸濁させて、そして1時間強力に撹拌した。固体を濾過し、ヘキサンで洗浄し、そして乾燥させて、オフホワイト色粉末として表題の生成物を得た(30.4g)。これは、NMRによって、純度>94%であると決定された。さらなる精製をせずに、この材料を工程Dで使用した。
1H NMR(CDCl3):δ6.52(s,1H)、7.30(dd,1H)、7.92(d,1H)、8.05(s,1H)、8.43(d,1H)
−76℃の乾燥テトラヒドロフラン(250mL)中2−(3−ブロモ−1H−ピラゾール−1−イル)−3−クロロピリジン(すなわち、工程Cの生成物)(30.4g、118ミリモル)の溶液に、−71℃未満の温度が保持されるような速度で、テトラヒドロフラン中リチウムジイソプロピルアミド(118ミリモル)の溶液を滴下して添加した。反応混合物を−76℃で15分間撹拌し、次いで、混合物中に二酸化炭素を10分間バブリングすると、−57℃まで加温が生じた。反応混合物を−20℃まで加温し、そして水でクエンチングした。反応混合物を濃縮し、次いで水(1L)およびエーテル(500mL)中に溶解し、次いで水酸化ナトリウム水溶液(1N、20mL)を添加した。水性抽出物をエーテルで洗浄し、そして塩酸で酸性化した。沈殿した固体を濾過し、水で洗浄し、そして乾燥して、黄褐色固体として表題の生成物を得た(27.7g)。(類似手順に従うもう1回の実行からの生成物は、200〜201℃で融解した。)
1H NMR(DMSO−d6):δ7.25(s,1H)、7.68(dd,1H)、8.24(d,1H)、8.56(d,1H)
塩化オキサリル(0.043mL、0.5ミリモル)を、室温で、塩化メチレン30mL中3−ブロモ−1−(3−クロロ−2−ピリジニル)−1H−ピラゾール−5−カルボン酸(すなわち、工程Dの生成物)(200mg、0.66ミリモル)および2滴のN,N−ジメチルホルムアミド(DMF)の混合物に添加し、そして反応を10分間混合した。この後、4−(ジメチルアミノ)ピリジンの触媒量を添加し、続いて、塩化メチレン10mL中トリエチルアミン(184mL、1.4ミリモル)および2−ブロモ−4,6−ジフルオロアミリンの混合物を滴下して添加した。反応を一晩撹拌し、次いで乾燥状態に近づくまで濃縮した。溶出剤としてヘキサン/酢酸エチル勾配(9:1〜1:1)を使用するシリカゲル上クロマトグラフィによって、油状物を得た。次いで、油状物をドライアイス中で冷却し、そしてエーテル/ヘキサンによって倍散し、138〜139℃で融解する固体として、本発明の化合物である表題の化合物(0.22g)を得た。
1H NMR(CDCl3):δ6.90(m,1H)、6.98(s,1H)、7.18(m,1H)、7.40(dd,1H)、7.55(br s,1H)、7.90(d,1H)、8.47(d,1H)
1−(3−クロロ−2−ピリジニル)−N−(2,4−ジクロロフェニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボキサミドの調製
塩化メチレン60mL中1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボン酸(すなわち、実施例1の工程Bからの生成物)(6.0g、20.76ミリモル)の溶液に、塩化オキサリル(5.7g、44.88ミリモル)と、それに続いて2滴のDMFを添加した。混合物を2時間撹拌し、その後、反応を減圧下でロータリーエバポレーター上で濃縮し、クロロホルム中に溶解し、そして2回目の濃縮をし、そして残留塩化オキサリルを除去した。得られた酸塩化物を、次の工程で直接使用した。
1H NMR(CDCl3):δ7.16(s,1H)、7.2(m,1H)、7.42(s,1H)、7.48(dd,1H)、7.94(dd,1H)、8.17(dd,1H)、8.38(br s,1H)、8.52(dd,1H)
索引表Bのアミドライブラリーの調製
塩化メチレン25mL中1−(3−クロロ−2−ピリジニル)−3−(トリフルオロメチル)−1H−ピラゾール−5−カルボン酸(すなわち、実施例1の工程Bからの生成物)(1.467g、6.3ミリモル)の溶液に、塩化オキサリル(2.6mL、37.8ミリモル)を添加した。最初のガス発生が停止した後、溶液を加熱し、2.5時間還流した。次いで、混合物を室温まで冷却し、そして濃縮した。得られた黄色油状物残渣を塩化メチレン(3×25mL)で倍散し、そして微量の塩化オキサリルを除去した。塩化メチレンで63mLの体積まで残渣を希釈することによって、この酸塩化物の0.1M保存液を調製した。次の工程で、直ちに保存液を使用した。ライブラリーで使用されるアニリンのそれぞれの塩化メチレン中0.1M保存液を調製した。0.5mg/mLの4−(ジメチルアミノ)ピリジンを含有する、塩化メチレン中トリエチルアミンの0.83M保存液を調製した。ドライボックスにおいて、ピペットによって、96ウェルブロックの個々のウェルに、アニリン保存溶液(250μL)を分配した。各ウェルに、酸塩化物保存液(300μL)、続いてトリエチルアミン保存液1(50μL)を添加した。次いで、ブロックを密封し、ドライボックスから取り出し、そして改造されたフレキシケム(Flexchem)(登録商標)オーブン(米国、カリフォルニア州、サニーベールのロビンス サイエンティフィック カンパニー(Robbins Scientific Co.Sunnyvale,California,USA))中に置き、窒素雰囲気下で一晩室温で撹拌した。次いでブロックの上部を取り外し、そして各ウェルにトリスアミン樹脂(75mg)を添加した。ブロックを再密封し、そして一晩撹拌した。ブロックの内容物を96ウェルマイクロタイタープレート中に濾過し、そして塩化メチレン200μLで洗浄した。200mgのハイドロマトリックス(Hydromatrix)(プラスか焼された珪藻土)(米国、カリフォルニア州、ウォールナット クリークのバリアン,インコーポレイテッド(Varian,Inc.Walnut Creek,California,USA))で各ウェルに充填し、次いで0.1M水酸化ナトリウム200μLによって水和することによって予め調製されたワットマン(Whatman)(登録商標)MBPPフィルタープレートに、組み合わせた濾液を添加した。プレートを、予め計量されたミクロニクスプレートに重力濾過し、そしてヒドロマトリックス(Hydromatrix)を塩化メチレン300μLで同一プレート中へと洗浄した。LCMS(液体クロマトグラフィマススペクトロメトリー)分析のために試料を取り出し、次いで溶媒を減圧下で除去した。調製されたライブラリーを索引表Bに報告する。エレクトロスプレーイオン化モードで操作されるマイクロマスLCT(商標)TOF(飛行時間)マススペクトロメーター上LCMS(英国、マンチェスターのマクロマス インコーポレイテッド(Macromass Inc.Manchester,UK))を使用して生成物分析を実行し、そして9分間100〜1200ダルトンからデータを収集した。LCシステムは、2.1×30mm ゾルバックス(Zorbax)SB−C18 ラピッド レゾリューション(Rapid Resolution)カラムを有するウォーターズ アリアンス(Waters Alliance)2790(米国、マサチューセッツ州、ミルフォードのウォーターズ カンパニー((Waters Co.Milford,Massachusetts,USA))であった。化合物を溶出するために、0.1%ギ酸を有する100%アセトニトリルへの0.1%ギ酸を有する水中10%アセトニトリルの6分の直線勾配、続いて3分保持を使用した。各インジェクションは、約0.5mg/mL溶液3μLであった。観察されたM+H(プロトン化分子イオン)を索引表Bに報告する。
本発明の化合物は一般的に、少なくとも1種の液体希釈剤、固体希釈剤または界面活性剤を含んでなる農業的に適切な担体とともに製剤または組成物として使用される。製剤または組成物成分は、活性成分の物性、適用形態、ならびに土壌タイプ、湿度および温度のような環境要因と調和するように選択される。有用な製剤は、場合によりゲルへと濃厚化されることが可能な、溶液(乳化可能な濃縮物を含む)、懸濁液、乳液(ミクロエマルジョンおよび/またはサスポエマルジョンを含む)等のような液体を含む。有用な製剤はさらに、水分散性(「水和」)または水溶性であり得る、ダスト、粉末、顆粒、ペレット、タブレット、フィルム等のような固体を含む。活性成分を(マイクロ)カプセル化することができ、さらに懸濁液または固体製剤へと形成することができ、あるいは活性成分の全製剤をカプセル化(または「オーバーコート」)することができる。カプセル化により、活性成分放出を制御することができるか、または遅らせることができる。噴霧可能な製剤を適切な培地に施すことができ、1ヘクタールあたり約1〜数百リットルの噴霧量で使用することができる。さらなる製剤の中間体として、最初に高強度組成物を使用する。
ヒメトビイロケアリ(Lasius alienus フォースター(Forster))、コヌカアリ(Tapinoma sessile セイ(Say)))、ハチ(クマバチを含む)、スズメバチ(hornet)、スズメバチ(yellow jacket)、大形のハチ(wasp)をはじめとするハチ目の昆虫害虫;ミゾガシラシロアリ(Reticulitermes flavipes コラー(Kollar))、セイヨウシロアリ(Reticulitermes hesperus バンクス(Banks))、イエシロアリ(Coptotermes formosanus シラキ(Shiraki))、ハワイシロアリ(Incisitermes immigrans シンダー(Snyder))および他の経済的観点から重要であるシロアリなどのシロアリ目の昆虫害虫;セイヨウシミ(Lepisma saccharina リンネ(Linnaeus))、マダラシミ(Thermobia domestica パッカード(Packard))などのシミ目の昆虫害虫;コロモジラミ(Pediculus humanus capitis デ・ギーア(De Geer))、アタマジラミ(Pediculus humanus humanus リンネ(Linnaeus))、ニワトリハジラミ(Menacanthus stramineus ニッツ(Nitszch))、イヌハジラミ(Trichodectes canis デ・ギーア(De Geer))、fluff louse(Goniocotes gallinae デ・ギーア(De Geer))、ヒツジハジラミ(Bovicola ovis シュランク(Schrank))、ウシジラミ(short−nosed cattle louse)(Haematopinus eurysternus ニッツ(Nitszch))、ウシジラミ(long−nosed cattle louse)(Linognathus vituli リンネ(Linnaeus))ならびに、人間や動物につく他の吸血シラミおよびハジラミを含むハジラミ目の昆虫害虫;ケオプスネズミノミ(Xenopsylla cheopis ロッシュチャイルド(Rothschild))、ネコノミ(Ctenocephalides felis ブーシュ(Bouche))、イヌノミ(Ctenocephalides canis カーティス(Curtis))、ニワトリノミ(Ceratophyllus gallinae シュランク(Schrank))、ニワトリフトノミ(Echidnophaga gallinacea ウェストウッド(Westwood))、ヒトノミ(Pulex irritans リンネ(Linnaeus))および人間や鳥を悩ます他のノミを含むノミ目の昆虫害虫が挙げられる。包含されるさらに他の節足動物害虫として、ドクイトグモ(Loxosceles reclusa グレッチュおよびミュレイク(Gertsch & Mulaik))ならびにクロゴケグモ(Latrodectus mactans ファブリシウス(Fabricius))などのクモ目のクモ、イエムカデ(Scutigera coleoptrata リンネ(Linnaeus))などの唇脚綱ゲジ目のムカデが挙げられる。本発明の化合物はまた、経済的観点から重要な農業害虫(すなわち、ネコブセンチュウ属の根こぶ線虫、ネグサレセンチュウ属の根ぐされ線虫、ユミハリセンチュウ属のユミハリ線虫など)ならびに動物および人間の健康を害する害虫(すなわち、経済的観点から重要なあらゆる吸虫、条虫および回虫であり、ウマの普通円虫(Strongylus vulgaris)、イヌの犬回虫(Toxocara canis)、ヒツジの捻転胃虫(Haemonchus contortus)、イヌの犬糸状虫(Dirofilaria immitis レイディ(Leidy))、ウマの葉状条虫(Anoplocephala perfoliata)、反芻動物の肝蛭虫(Fasciola hepatica リンネ(Linnaeus))など)などであるがこれに限定されるものではない、円虫目、回虫目、蟯虫目、ラブジチダ目、センビセンチュウ目、エノプルス目の経済的観点から重要な虫類をはじめとする、線虫綱、条虫綱、吸虫綱および鉤頭動物門の虫類に対する活性を有する。
試験A
コナガ(Plutella xylostella)の防除を評価するために、12〜14日齢ラディッシュ植物を内部に含む小型開放容器で試験ユニットを構成した。コアサンプラーの使用により、昆虫食餌の一片において10〜15個体の新生幼虫で、これを事前に外寄生させ、シート上に多くの発育幼虫を有する硬化した昆虫食餌のシートからプラグを取り出し、そして幼虫および食餌を含有するプラグを試験ユニットに移した。食餌プラグが乾燥すると、幼虫は試験植物上へと移動した。
ヨトウガの一種(Spodoptera frugiperda)の防除を評価するために、4〜5日齢コーン(トウモロコシ)植物を内部に含む小型開放容器で試験ユニットを構成した。昆虫食餌の一片において10〜15個体の1日齢幼虫で、(コアサンプラーの使用により)これを事前に外寄生させた。
オオタバコガ(Heliothis virescens)の防除を評価するために、6〜7日齢綿植物を内部に含む小型開放容器で試験ユニットを構成した。昆虫食餌の一片において8個体の2日齢幼虫で、(コアサンプラーの使用により)これを事前に外寄生させた。
シロイチモジヨトウ(Spodoptera exigua)の防除を評価するために、4〜5日齢コーン植物を内部に含む小型開放容器で試験ユニットを構成した。昆虫食餌の一片において10〜15個体の1日齢幼虫で、(コアサンプラーの使用により)これを事前に外寄生させた。
ヨトウガの一種(Spodoptera frugiperda)の防除を評価するための代替方法として、175μLの鱗翅目昆虫のダイズコムギ胚芽食餌で充填したマイクロタイタープレートで試験ユニットを構成した。75/25アセトン/水中に配合された1050μM(またはそれ以下)実験化合物25μLで、各ウェルを処理した。化学的適用後、24時間、換気式囲いの中でプレートを乾燥させた。24時間の乾燥期間の後、ヨトウガの一種の卵でプレートを外寄生させ、次いで密封した。次いで、6日間、27℃(日)70%相対湿度で、試験ユニットを貯蔵した。昆虫の死亡を基準として活性を評価した。
**250ppmで試験された。
***50ppmで試験された。
Claims (14)
- 式I
[式中、
AはOまたはSであり、
Bは1〜5個のR2によって各環が置換されているフェニル環またはピリジン環であり、
JがJ−1、J−2、J−3、J−4、J−5およびJ−6よりなる群から選択されるピラゾールまたはピロール複素環式環系であり、
R1はH、あるいはそれぞれ場合によりハロゲン、CN、NO2、ヒドロキシ、C1〜C4アルコキシ、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C2〜C4アルコキシカルボニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノおよびC3〜C6シクロアルキルアミノよりなる群から選択される1個もしくはそれ以上の置換基によって置換されていてもよいC1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニルまたはC3〜C6シクロアルキルであるか、あるいは
R1はC2〜C6アルキルカルボニル、C2〜C6アルコキシカルボニル、C2〜C6アルキルアミノカルボニルまたはC3〜C8ジアルキルアミノカルボニルであり、
各R2は独立してH、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C3〜C6シクロアルキル、C1〜C6ハロアルキル、C2〜C6ハロアルケニル、C2〜C6ハロアルキニル、C3〜C6ハロシクロアルキル、C2〜C4シアノアルキル、ハロゲン、CN、NO2、ピペリジン、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4ハロアルキルチオ、C1〜C4ハロアルキルスルフィニル、C1〜C4ハロアルキルスルホニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノ、C3〜C6シクロアルキルアミノよりなる群から選択されるか、あるいは
各R2は独立して各環が場合によりC1〜C4アルキル、C2〜C4アルケニル、C2〜C4アルキニル、C3〜C6シクロアルキル、C1〜C4ハロアルキル、C2〜C4ハロアルケニル、C2〜C4ハロアルキニル、C3〜C6ハロシクロアルキル、ハロゲン、CN、NO2、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4アルキルアミノ、C2〜C8ジアルキルアミノ、C3〜C6シクロアルキルアミノ、C4〜C7(アルキル)シクロアルキルアミノ、C2〜C6アルコキシカルボニル、C2〜C6アルキルアミノカルボニルおよびC3〜C8ジアルキルアミノカルボニルよりなる群から選択される1個もしくはそれ以上の置換基によって置換されていてもよいフェニル、ベンジルまたはフェノキシ環よりなる群から選択され、
R5は
であり、
各R6、R6aおよびR7は独立してH、C1〜C6アルキル、C3〜C6シクロアルキル、C1〜C6ハロアルキル、ハロゲン、CN、C1〜C4アルコキシ、C1〜C4アルキルチオ、C1〜C4ハロアルコキシおよびC1〜C4ハロアルキルチオよりなる群から選択され、そして
R8はH、C1〜C6アルキル、C1〜C6ハロアルキル、C3〜C6アルケニル、C3〜C6ハロアルケニル、C3〜C6アルキニル、C3〜C6ハロアルキニルまたはC1〜C4ハロアルコキシである]
の化合物、そのN−オキシドまたは塩。 - JがJ−1、J−2、J−3またはJ−6である
請求項1に記載の化合物。 - AがOであり、
R1がHであり、
1〜3個のR2基がH以外であり、かつ独立してC1〜C6アルキル、C1〜C6ハロアルキル、C2〜C4シアノアルキル、ハロゲン、CN、NO2、ピペリジン、C1〜C4アルコキシ、C1〜C4ハロアルコキシ、C2〜C4アルコキシカルボニル、C1〜C4アルキルチオ、C1〜C4アルキルスルフィニル、C1〜C4アルキルスルホニル、C1〜C4ハロアルキルチオ、C1〜C4ハロアルキルスルフィニルおよびC1〜C4ハロアルキルスルホニルよりなる群から選択され、そして
直前に記載の少なくとも1個のR2がNR1C(=A)J部分に対してオルトにある
請求項2に記載の化合物。 - 2個のR2がNR1C(=A)J部分に対してオルトにある請求項3に記載の化合物。
- R6がH、C1〜C4アルキル、C1〜C4ハロアルキル、ハロゲンまたはCNであり、そして
R7がH、CH3、CF3、CH2CF3、CHF2、OCH2CF3、OCHF2またはハロゲンである
請求項3に記載の化合物。 - JがJ−1であり、
R6がClまたはBrであり、そして
R7がハロゲン、OCH2CF3、OCHF2またはCF3である
請求項5に記載の化合物。 - JがJ−2であり、
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である
請求項5に記載の化合物。 - JがJ−3であり、
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である
請求項5に記載の化合物。 - JがJ−5であり、
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である
請求項5に記載の化合物。 - JがJ−6であり、
R6がClまたはBrであり、そして
R8がCH2CF3またはCHF2である
請求項5に記載の化合物。 - 少なくとも1種の請求項1に記載の化合物と、界面活性剤、固体希釈剤および液体希釈剤よりなる群から選択される少なくとも1種の追加成分とを含んでなる組成物。
- 少なくとも1種の他の生物学的に活性な化合物または薬剤をさらに含んでなる請求項11に記載の組成物。
- 無脊椎有害生物またはその環境を、少なくとも1種の請求項1に記載の化合物の生物学的に有効な量または請求項11に記載の組成物の生物学的に有効な量と接触させることを含んでなる少なくとも1種の無脊椎有害生物の防除方法。
- 組成物が、無脊椎有害生物を防除するための少なくとも1種の他の生物学的に活性な化合物または薬剤の生物学的に有効な量をさらに含んでなる請求項13に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38824402P | 2002-06-13 | 2002-06-13 | |
PCT/US2003/018609 WO2003106427A2 (en) | 2002-06-13 | 2003-06-10 | Pyrazolecarboxamide insecticides |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005532367A true JP2005532367A (ja) | 2005-10-27 |
JP4287816B2 JP4287816B2 (ja) | 2009-07-01 |
Family
ID=29736447
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004513260A Expired - Fee Related JP4287816B2 (ja) | 2002-06-13 | 2003-06-10 | ピラゾールカルボキサミド殺虫剤 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7754738B2 (ja) |
EP (1) | EP1511733A2 (ja) |
JP (1) | JP4287816B2 (ja) |
KR (1) | KR20050009747A (ja) |
CN (1) | CN100335477C (ja) |
AU (1) | AU2003245464A1 (ja) |
BR (1) | BR0311707A (ja) |
MX (1) | MXPA04012214A (ja) |
WO (1) | WO2003106427A2 (ja) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010536926A (ja) * | 2007-08-27 | 2010-12-02 | ビーエーエスエフ ソシエタス・ヨーロピア | 無脊椎動物系害虫を防除するためのピラゾール化合物 |
US8710056B2 (en) | 2009-07-06 | 2014-04-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
US8729083B2 (en) | 2008-09-24 | 2014-05-20 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
JP2015511229A (ja) * | 2012-02-07 | 2015-04-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 置換アントラニル酸誘導体を製造する方法 |
US9029639B2 (en) | 2009-07-06 | 2015-05-12 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
JP2015517487A (ja) * | 2012-05-07 | 2015-06-22 | キョン ノン コーポレーション | カルバミン酸により置換されたジアミノアリール誘導体及びこれを含有する殺虫剤組成物 |
US9125414B2 (en) | 2009-07-24 | 2015-09-08 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
JP2017507160A (ja) * | 2014-03-07 | 2017-03-16 | バイオクリスト ファーマスーティカルズ,インコーポレイテッドBiocryst Pharmaceuticals,Inc. | ヒト血漿カリクレイン阻害剤 |
US12116346B2 (en) | 2023-04-18 | 2024-10-15 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
TWI312274B (en) | 2001-08-13 | 2009-07-21 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
CN1865258A (zh) | 2001-08-15 | 2006-11-22 | 纳幕尔杜邦公司 | 用于控制无脊椎害虫的邻位取代的芳基酰胺化合物 |
EP1417176B1 (en) | 2001-08-16 | 2008-12-17 | E.I. Du Pont De Nemours And Company | Substituted anthranilamides for controlling invertebrate pests |
TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
EP1560820B1 (en) | 2002-11-15 | 2010-05-26 | E.I. Du Pont De Nemours And Company | Novel anthranilamide insecticides |
CA2512242C (en) | 2003-01-28 | 2012-07-24 | E. I. Du Pont De Nemours And Company | Cyano anthranilamide insecticides |
JP4543043B2 (ja) | 2003-06-12 | 2010-09-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 縮合オキサジノンの製造方法 |
JO2540B1 (en) | 2004-07-01 | 2010-09-05 | اي.اي.ديو بونت دي نيمورز اند كومباني | Control factors for pests from invertebrate insects include a symbiotic mixture of anthranilamide |
CA2582777A1 (en) * | 2004-09-30 | 2006-04-06 | Takeda Pharmaceutical Company Limited | Proton pump inhibitors |
KR101292486B1 (ko) * | 2004-11-18 | 2013-08-01 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 안트라닐아미드 살충제 |
JP5039703B2 (ja) | 2005-08-24 | 2012-10-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 無脊椎有害生物防除用アントラニルアミド |
DK1919865T3 (da) | 2005-08-30 | 2011-05-23 | Takeda Pharmaceutical | 1-Heterocyclylsulfonyl, 2-aminomethyl, 5-(hetero-)aryl-substituerede 1-h-pyrrolderivater som syresekretionsinhibitorer |
US8933105B2 (en) | 2007-02-28 | 2015-01-13 | Takeda Pharmaceutical Company Limited | Pyrrole compounds |
US8299115B2 (en) * | 2007-06-08 | 2012-10-30 | Debnath Bhuniya | Pyrrole-2-carboxamide derivatives as glucokinase activators, their process and pharmaceutical application |
CN101808995A (zh) | 2007-07-27 | 2010-08-18 | 百时美施贵宝公司 | 新颖的葡糖激酶激活剂及其使用方法 |
WO2009108180A2 (en) * | 2007-12-20 | 2009-09-03 | University Of Georgia Research Foundation, Inc. | Plant production and delivery system for recombinant proteins as protein-flour or protein-oil compositions |
EP2725022B1 (de) * | 2008-06-13 | 2017-03-29 | Bayer CropScience AG | Neue Amide als Schädlingsbekämpfungsmittel |
EP2318390B1 (en) | 2008-08-27 | 2013-05-01 | Takeda Pharmaceutical Company Limited | Pyrrole compounds |
CN102216276A (zh) | 2008-09-11 | 2011-10-12 | 辉瑞大药厂 | 取代的杂芳基物 |
WO2010034738A2 (en) * | 2008-09-24 | 2010-04-01 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
PL2406253T3 (pl) | 2009-03-11 | 2013-10-31 | Pfizer | Pochodne benzofuranylu jako inhibitory glukokinazy |
CN102834391A (zh) | 2010-03-23 | 2012-12-19 | 巴斯夫欧洲公司 | 防治无脊椎动物害虫的哒嗪化合物 |
ES2589792T3 (es) | 2010-03-23 | 2016-11-16 | Basf Se | Compuestos de piridazina para el control de plagas de invertebrados |
EP2582693B1 (de) * | 2010-06-15 | 2016-03-30 | Bayer Intellectual Property GmbH | Neue ortho-substituierte arylamid-derivate |
WO2012083190A1 (en) * | 2010-12-17 | 2012-06-21 | The Rockefeller University | Insect odorant receptor antagonists |
IN2014CN00979A (ja) | 2011-08-12 | 2015-04-10 | Basf Se | |
MX2014001038A (es) | 2011-08-12 | 2014-03-27 | Basf Se | Compuestos tipo anilina. |
KR20140051401A (ko) | 2011-08-12 | 2014-04-30 | 바스프 에스이 | N-치환된 1h-피라졸-5-카르보닐클로라이드 화합물을 제조하는 방법 |
JP2014522876A (ja) | 2011-08-12 | 2014-09-08 | ビーエーエスエフ ソシエタス・ヨーロピア | N−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
CN103889960A (zh) | 2011-08-18 | 2014-06-25 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的氨基甲酰基甲氧基-和氨基甲酰基甲硫基-及氨基甲酰基甲基氨基苯甲酰胺 |
CN102391248B (zh) * | 2011-09-29 | 2016-05-11 | 杭州宇龙化工有限公司 | 邻氨基苯甲腈类化合物及其制法与用途 |
BR112014012243A2 (pt) | 2011-11-21 | 2017-05-30 | Basf Se | processo de preparação de compostos |
EP3377486B1 (en) * | 2015-11-18 | 2024-09-18 | Monsanto Technology LLC | Method of controlling insect pests |
CN105541794A (zh) * | 2016-01-08 | 2016-05-04 | 南开大学 | 含有七氟异丙基的吡啶基吡唑酰胺类衍生物及其应用 |
CN105712975B (zh) * | 2016-01-26 | 2018-10-12 | 西安近代化学研究所 | 一种含有1,2,3-三唑环的吡唑酰胺化合物和应用 |
KR102035091B1 (ko) * | 2018-02-08 | 2019-10-23 | 한국화학연구원 | 오가노설퍼기를 포함하는 피라졸 카복사마이드 화합물 및 이를 함유하는 살충제 조성물 |
KR102483540B1 (ko) * | 2018-11-14 | 2023-01-02 | 한국화학연구원 | 오가노설퍼기를 포함하는 피라졸 카복사마이드 화합물을 함유하는 살진드기제 조성물 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2934543A1 (de) * | 1979-08-27 | 1981-04-02 | Basf Ag, 6700 Ludwigshafen | Substituierte n-benzoylanthranilsaeurederivate und deren anydroverbindungen, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
JPH02129171A (ja) * | 1988-11-08 | 1990-05-17 | Nissan Chem Ind Ltd | ピラゾールカルボキサニリド誘導体及び有害生物防除剤 |
US6020357A (en) | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
SK86699A3 (en) | 1996-12-23 | 2000-11-07 | Du Pont Pharm Co | Nitrogen containing heteroaromatics as factor xa inhibitors |
US6548512B1 (en) | 1996-12-23 | 2003-04-15 | Bristol-Myers Squibb Pharma Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
US5998424A (en) | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
IL133526A0 (en) | 1997-06-19 | 2001-04-30 | Du Pont Pharm Co | Inhibitors of factor xa with a neutral p1 specificity group |
MY138097A (en) | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
US20040102324A1 (en) * | 2002-02-28 | 2004-05-27 | Annis Gary David | Heterocyclic diamide invertebrate pest control agents |
CN1280277C (zh) | 2001-05-21 | 2006-10-18 | 纳幕尔杜邦公司 | 含非芳族杂环的肼无脊椎害虫防治剂 |
EP1417200B1 (en) | 2001-08-13 | 2010-06-02 | E.I. Du Pont De Nemours And Company | Substituted 1h-dihydropyrazoles, their preparation and use |
AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
TWI356822B (en) | 2001-08-13 | 2012-01-21 | Du Pont | Novel substituted dihydro 3-halo-1h-pyrazole-5-car |
TWI312274B (en) | 2001-08-13 | 2009-07-21 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
KR20040022246A (ko) * | 2001-08-15 | 2004-03-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무척추 해충 방제용 오르토-헤테로시클릭 치환 아릴 아미드 |
CN1865258A (zh) * | 2001-08-15 | 2006-11-22 | 纳幕尔杜邦公司 | 用于控制无脊椎害虫的邻位取代的芳基酰胺化合物 |
EP1417176B1 (en) | 2001-08-16 | 2008-12-17 | E.I. Du Pont De Nemours And Company | Substituted anthranilamides for controlling invertebrate pests |
US7179824B2 (en) | 2001-09-21 | 2007-02-20 | E. I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
WO2003026415A2 (en) * | 2001-09-21 | 2003-04-03 | E.I. Du Pont De Nemours And Company | Insecticidal diamides |
DE60230651D1 (de) | 2001-10-15 | 2009-02-12 | Du Pont | Iminobenzoxazine, iminobenzothiazine and iminoquinazoline zur bekämpfung von wirbellosen schädlingen |
US20040110777A1 (en) | 2001-12-03 | 2004-06-10 | Annis Gary David | Quinazolinones and pyridinylpyrimidinones for controlling invertebrate pests |
WO2003062226A1 (en) | 2002-01-22 | 2003-07-31 | E. I. Du Pont De Nemours And Company | Quinazoline(di) ones for invertebrate pest control |
WO2003062221A1 (en) | 2002-01-22 | 2003-07-31 | E.I. Du Pont De Nemours And Company | Diamide invertebrate pest control agents |
-
2003
- 2003-06-10 CN CNB038127318A patent/CN100335477C/zh not_active Expired - Fee Related
- 2003-06-10 EP EP03739103A patent/EP1511733A2/en not_active Withdrawn
- 2003-06-10 JP JP2004513260A patent/JP4287816B2/ja not_active Expired - Fee Related
- 2003-06-10 AU AU2003245464A patent/AU2003245464A1/en not_active Abandoned
- 2003-06-10 US US10/514,183 patent/US7754738B2/en not_active Expired - Fee Related
- 2003-06-10 BR BR0311707-3A patent/BR0311707A/pt not_active IP Right Cessation
- 2003-06-10 WO PCT/US2003/018609 patent/WO2003106427A2/en active Application Filing
- 2003-06-10 MX MXPA04012214A patent/MXPA04012214A/es not_active Application Discontinuation
- 2003-06-10 KR KR10-2004-7020187A patent/KR20050009747A/ko not_active Application Discontinuation
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8642597B2 (en) | 2007-08-27 | 2014-02-04 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US9204647B2 (en) | 2007-08-27 | 2015-12-08 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
JP2010536926A (ja) * | 2007-08-27 | 2010-12-02 | ビーエーエスエフ ソシエタス・ヨーロピア | 無脊椎動物系害虫を防除するためのピラゾール化合物 |
US8729083B2 (en) | 2008-09-24 | 2014-05-20 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US9375008B2 (en) | 2008-09-24 | 2016-06-28 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US8710056B2 (en) | 2009-07-06 | 2014-04-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
US9029639B2 (en) | 2009-07-06 | 2015-05-12 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
US9125414B2 (en) | 2009-07-24 | 2015-09-08 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
US9969717B2 (en) | 2012-02-07 | 2018-05-15 | Bayer Intellectual Property Gmbh | Method for producing substituted anthranilic acid derivatives |
JP2015511229A (ja) * | 2012-02-07 | 2015-04-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 置換アントラニル酸誘導体を製造する方法 |
US9670182B2 (en) | 2012-02-07 | 2017-06-06 | Bayer Intellectual Property Gmbh | Method for producing substituted anthranilic acid derivatives |
JP2015517487A (ja) * | 2012-05-07 | 2015-06-22 | キョン ノン コーポレーション | カルバミン酸により置換されたジアミノアリール誘導体及びこれを含有する殺虫剤組成物 |
JP2017507160A (ja) * | 2014-03-07 | 2017-03-16 | バイオクリスト ファーマスーティカルズ,インコーポレイテッドBiocryst Pharmaceuticals,Inc. | ヒト血漿カリクレイン阻害剤 |
US10329260B2 (en) | 2014-03-07 | 2019-06-25 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US10633345B2 (en) | 2014-03-07 | 2020-04-28 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US10689346B2 (en) | 2014-03-07 | 2020-06-23 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US11192861B2 (en) | 2014-03-07 | 2021-12-07 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US11203574B2 (en) | 2014-03-07 | 2021-12-21 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US11230530B2 (en) | 2014-03-07 | 2022-01-25 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US11685721B2 (en) | 2014-03-07 | 2023-06-27 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US11708332B2 (en) | 2014-03-07 | 2023-07-25 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US11708333B2 (en) | 2014-03-07 | 2023-07-25 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
US12116346B2 (en) | 2023-04-18 | 2024-10-15 | Biocryst Pharmaceuticals, Inc. | Human plasma kallikrein inhibitors |
Also Published As
Publication number | Publication date |
---|---|
AU2003245464A1 (en) | 2003-12-31 |
MXPA04012214A (es) | 2005-02-25 |
CN100335477C (zh) | 2007-09-05 |
US7754738B2 (en) | 2010-07-13 |
WO2003106427A2 (en) | 2003-12-24 |
CN1659160A (zh) | 2005-08-24 |
US20060167060A1 (en) | 2006-07-27 |
BR0311707A (pt) | 2005-03-15 |
WO2003106427A3 (en) | 2004-06-24 |
JP4287816B2 (ja) | 2009-07-01 |
KR20050009747A (ko) | 2005-01-25 |
EP1511733A2 (en) | 2005-03-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4287816B2 (ja) | ピラゾールカルボキサミド殺虫剤 | |
JP4394953B2 (ja) | 無脊椎有害生物防除のためのキナゾリン(ジ)オン | |
JP4648705B2 (ja) | 新規アントラニルアミド殺虫剤 | |
JP4445751B2 (ja) | 無脊椎有害生物を防除するためのo−複素環式置換アリールアミド | |
JP4370098B2 (ja) | ヘテロ環式ジアミド無脊椎有害動物防除剤 | |
JP4095959B2 (ja) | 無脊椎有害生物を防除するためのオルト置換アリールアミド類 | |
JP4224397B2 (ja) | 無脊椎有害生物の防除用の置換アントラニルアミド | |
JP3764895B1 (ja) | シアノアントラニルアミド殺虫剤 | |
JP2006502226A (ja) | アントラニルアミド殺虫剤 | |
JP2004515543A (ja) | 有害無脊椎動物を防除するためのキナゾリノン類およびピリジニルピリミジノン類 | |
JP4317752B2 (ja) | 無脊椎害虫を防除するためのイミノベンゾオキサジン、イミノベンズチアジンおよびイミノキナゾリン | |
JP2008510721A (ja) | 無脊椎有害生物の防除に有用な新規アントラニルアミド | |
JP2007532661A (ja) | アントラニルアミド殺虫剤 | |
JP2004515547A (ja) | 置換複素環式フタル酸ジアミド殺節足動物剤 | |
JP2005516037A (ja) | ジアミド無脊椎有害生物防除剤 | |
DE60302572T2 (de) | Insektizide amide mit stickstoffhaltigen kondensierten bizyklischen ringsystemen | |
JP2004511538A (ja) | 殺昆虫性1,8−ナフタレンジカルボキサミド類 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20080208 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20080208 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20080405 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090303 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20090327 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120403 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130403 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140403 Year of fee payment: 5 |
|
LAPS | Cancellation because of no payment of annual fees |