MXPA05003337A

MXPA05003337A - Insecticidas de antranilamida.

Insecticidas de antranilamida.

Info

Publication number: MXPA05003337A
Authority: MX; Mexico
Prior art keywords: alkyl; compound; halogen; alkoxy; formula
Prior art date: 2002-10-04

Application number

MXPA05003337A

Other languages

English (en)

Spanish (es)

Inventor

Martin Stevenson Thomas

Original Assignee

Du Pont

Priority date

2002-10-04

Filing date

2003-10-01

Publication date

2005-07-05

2003-10-01 Application filed by Du Pont filed Critical Du Pont

2005-07-05 Publication of MXPA05003337A publication Critical patent/MXPA05003337A/es

Links

239000002917 insecticide Substances 0.000 title description 7
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 152
239000000203 mixture Substances 0.000 claims abstract description 95
241000607479 Yersinia pestis Species 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
239000003085 diluting agent Substances 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 15
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
239000007787 solid Substances 0.000 claims abstract description 9
239000004094 surface-active agent Substances 0.000 claims abstract description 9
239000007788 liquid Substances 0.000 claims abstract description 8
150000001204 N-oxides Chemical class 0.000 claims abstract description 7
229910052740 iodine Inorganic materials 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
-1 C4-cycloalkyl Chemical group 0.000 claims description 57
125000001424 substituent group Chemical group 0.000 claims description 30
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 27
108010081348 HRT1 protein Hairy Proteins 0.000 claims description 27
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 27
125000001188 haloalkyl group Chemical group 0.000 claims description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
229910052794 bromium Inorganic materials 0.000 claims description 17
239000007921 spray Substances 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 16
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
241000255925 Diptera Species 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 10
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 10
235000013305 food Nutrition 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
125000004663 dialkyl amino group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
125000004995 haloalkylthio group Chemical group 0.000 claims description 8
125000000232 haloalkynyl group Chemical group 0.000 claims description 8
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 7
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 7
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 7
239000000463 material Substances 0.000 claims description 7
241000239290 Araneae Species 0.000 claims description 6
241000257303 Hymenoptera Species 0.000 claims description 6
241000256856 Vespidae Species 0.000 claims description 6
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
125000004438 haloalkoxy group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
241001674044 Blattodea Species 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
241000256602 Isoptera Species 0.000 claims description 4
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 4
125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
239000003906 humectant Substances 0.000 claims description 4
CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 4
239000003380 propellant Substances 0.000 claims description 4
125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
241001425390 Aphis fabae Species 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
239000000443 aerosol Substances 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
241000692235 Lipoptena cervi Species 0.000 claims 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
241000257191 Oestridae Species 0.000 claims 1
239000000460 chlorine Substances 0.000 description 68
238000006243 chemical reaction Methods 0.000 description 50
230000009418 agronomic effect Effects 0.000 description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
241000238631 Hexapoda Species 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
241000196324 Embryophyta Species 0.000 description 19
238000003786 synthesis reaction Methods 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 18
238000012360 testing method Methods 0.000 description 18
239000000047 product Substances 0.000 description 17
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000009472 formulation Methods 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
239000002253 acid Substances 0.000 description 14
241000238876 Acari Species 0.000 description 12
241000209149 Zea Species 0.000 description 12
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
235000002017 Zea mays subsp mays Nutrition 0.000 description 12
235000005822 corn Nutrition 0.000 description 12
239000008187 granular material Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
241001124076 Aphididae Species 0.000 description 10
244000299507 Gossypium hirsutum Species 0.000 description 10
241000244206 Nematoda Species 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
238000010992 reflux Methods 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
229920000742 Cotton Polymers 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 8
241000254173 Coleoptera Species 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
241001414989 Thysanoptera Species 0.000 description 8
230000003647 oxidation Effects 0.000 description 8
238000007254 oxidation reaction Methods 0.000 description 8
239000000843 powder Substances 0.000 description 8
150000003217 pyrazoles Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
230000006378 damage Effects 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
241000193388 Bacillus thuringiensis Species 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
229940097012 bacillus thuringiensis Drugs 0.000 description 6
229940125904 compound 1 Drugs 0.000 description 6
235000013399 edible fruits Nutrition 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
239000005660 Abamectin Substances 0.000 description 5
235000013162 Cocos nucifera Nutrition 0.000 description 5
244000060011 Cocos nucifera Species 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241000237858 Gastropoda Species 0.000 description 5
241000258937 Hemiptera Species 0.000 description 5
241000500437 Plutella xylostella Species 0.000 description 5
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
235000020971 citrus fruits Nutrition 0.000 description 5
235000005911 diet Nutrition 0.000 description 5
230000037213 diet Effects 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
235000013311 vegetables Nutrition 0.000 description 5
WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 4
241000273311 Aphis spiraecola Species 0.000 description 4
241000238421 Arthropoda Species 0.000 description 4
241000207199 Citrus Species 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
241000258916 Leptinotarsa decemlineata Species 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
241001674048 Phthiraptera Species 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000036541 health Effects 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
239000008188 pellet Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
238000005507 spraying Methods 0.000 description 4
150000003512 tertiary amines Chemical class 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
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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241001014341 Acrosternum hilare Species 0.000 description 3
241001600408 Aphis gossypii Species 0.000 description 3
241000254127 Bemisia tabaci Species 0.000 description 3
239000005884 Beta-Cyfluthrin Substances 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000258920 Chilopoda Species 0.000 description 3
241000254171 Curculionidae Species 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
241000233866 Fungi Species 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
241001387505 Heterotermes tenuis Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000005906 Imidacloprid Substances 0.000 description 3
239000005907 Indoxacarb Substances 0.000 description 3
241000255777 Lepidoptera Species 0.000 description 3
241000255908 Manduca sexta Species 0.000 description 3
239000005916 Methomyl Substances 0.000 description 3
241000257226 Muscidae Species 0.000 description 3
241000721621 Myzus persicae Species 0.000 description 3
241001012098 Omiodes indicata Species 0.000 description 3
241000238814 Orthoptera Species 0.000 description 3
239000005950 Oxamyl Substances 0.000 description 3
241000517307 Pediculus humanus Species 0.000 description 3
241000255969 Pieris brassicae Species 0.000 description 3
239000005925 Pymetrozine Substances 0.000 description 3
240000003768 Solanum lycopersicum Species 0.000 description 3
241000517830 Solenopsis geminata Species 0.000 description 3
241000985245 Spodoptera litura Species 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000005940 Thiacloprid Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
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229940100198 alkylating agent Drugs 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
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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 3
239000000969 carrier Substances 0.000 description 3
238000005660 chlorination reaction Methods 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
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
229940013764 fipronil Drugs 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
230000026030 halogenation Effects 0.000 description 3
238000005658 halogenation reaction Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 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
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 3
238000002156 mixing Methods 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
239000000575 pesticide Substances 0.000 description 3
102000004169 proteins and genes Human genes 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
150000003233 pyrroles Chemical class 0.000 description 3
125000000168 pyrrolyl group Chemical group 0.000 description 3
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