CN1140449A - 用作害虫防治剂的n-吡唑基苯胺和n-吡唑基氨基吡啶 - Google Patents
用作害虫防治剂的n-吡唑基苯胺和n-吡唑基氨基吡啶 Download PDFInfo
- Publication number
- CN1140449A CN1140449A CN95191611.4A CN95191611A CN1140449A CN 1140449 A CN1140449 A CN 1140449A CN 95191611 A CN95191611 A CN 95191611A CN 1140449 A CN1140449 A CN 1140449A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- represent
- chlorine
- fluorine
- haloalkyl
- 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.)
- Pending
Links
- CMAOIURPBUCSJE-UHFFFAOYSA-N n-phenyl-1h-pyrazol-5-amine Chemical class C=1C=CC=CC=1NC=1C=CNN=1 CMAOIURPBUCSJE-UHFFFAOYSA-N 0.000 title claims abstract description 9
- GXXITYWMMSFJHS-UHFFFAOYSA-N 1-(1h-pyrazol-5-yl)-2h-pyridin-2-amine Chemical class NC1C=CC=CN1C1=CC=NN1 GXXITYWMMSFJHS-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000000575 pesticide Substances 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims description 142
- 229910052801 chlorine Inorganic materials 0.000 claims description 62
- 239000000460 chlorine Substances 0.000 claims description 60
- 239000011737 fluorine Substances 0.000 claims description 59
- 229910052731 fluorine Inorganic materials 0.000 claims description 59
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 57
- 238000002360 preparation method Methods 0.000 claims description 55
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 54
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 54
- 229910052794 bromium Inorganic materials 0.000 claims description 54
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910004013 NO 2 Inorganic materials 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- -1 methylidene, ethyl Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 14
- 238000010572 single replacement reaction Methods 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 241000607479 Yersinia pestis Species 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000011630 iodine Substances 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000006414 CCl Chemical group ClC* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 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 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 238000012360 testing method Methods 0.000 description 26
- 239000003995 emulsifying agent Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 229920000151 polyglycol Polymers 0.000 description 12
- 239000010695 polyglycol Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 241000256259 Noctuidae Species 0.000 description 7
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- 241001454293 Tetranychus urticae Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 150000003851 azoles Chemical class 0.000 description 6
- 238000007598 dipping method Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 239000005660 Abamectin Substances 0.000 description 5
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 5
- 241001414720 Cicadellidae Species 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 241000233679 Peronosporaceae Species 0.000 description 5
- 241000228452 Venturia inaequalis Species 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 244000000010 microbial pathogen Species 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241001674044 Blattodea Species 0.000 description 4
- 235000007516 Chrysanthemum Nutrition 0.000 description 4
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241000238675 Periplaneta americana Species 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- 241000267822 Trogoderma granarium Species 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 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 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 229940031815 mycocide Drugs 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000012549 training Methods 0.000 description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
- KNCHDRLWPAKSII-UHFFFAOYSA-N 5-ethyl-2-methylpyridine Natural products CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- 241000238421 Arthropoda Species 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 235000011303 Brassica alboglabra Nutrition 0.000 description 3
- 235000011302 Brassica oleracea Nutrition 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241000257162 Lucilia <blowfly> Species 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 3
- 241001649229 Psoroptes Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000012747 synergistic agent Substances 0.000 description 3
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 description 2
- ATROHALUCMTWTB-WYMLVPIESA-N (z)-n-diethoxyphosphinothioyloxybenzenecarboximidoyl cyanide Chemical compound CCOP(=S)(OCC)O\N=C(/C#N)C1=CC=CC=C1 ATROHALUCMTWTB-WYMLVPIESA-N 0.000 description 2
- QMTFKWDCWOTPGJ-KVVVOXFISA-N (z)-octadec-9-enoic acid;tin Chemical compound [Sn].CCCCCCCC\C=C/CCCCCCCC(O)=O QMTFKWDCWOTPGJ-KVVVOXFISA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001427556 Anoplura Species 0.000 description 2
- 235000011330 Armoracia rusticana Nutrition 0.000 description 2
- 240000003291 Armoracia rusticana Species 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 2
- 241001674939 Caulanthus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000675108 Citrus tangerina Species 0.000 description 2
- 241001498622 Cixius wagneri Species 0.000 description 2
- 241001427559 Collembola Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000005946 Cypermethrin Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241001517923 Douglasiidae Species 0.000 description 2
- 241000086608 Empoasca vitis Species 0.000 description 2
- 239000005899 Fipronil Substances 0.000 description 2
- 206010018498 Goitre Diseases 0.000 description 2
- 241000256257 Heliothis Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 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 2
- 239000005912 Lufenuron Substances 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000896238 Oidium Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241000517307 Pediculus humanus Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005663 Pyridaben Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241001157780 Scutigera coleoptrata Species 0.000 description 2
- 241000258242 Siphonaptera Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000005658 Tebufenpyrad Substances 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- QYIJPFYCTROKTM-UHFFFAOYSA-N [Sn].P(O)(O)(O)=O Chemical compound [Sn].P(O)(O)(O)=O QYIJPFYCTROKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 210000003323 beak Anatomy 0.000 description 2
- XEGGRYVFLWGFHI-UHFFFAOYSA-N bendiocarb Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)O2 XEGGRYVFLWGFHI-UHFFFAOYSA-N 0.000 description 2
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 2
- KJQZTGPKDPXWBE-UHFFFAOYSA-N benzoic acid;tin Chemical compound [Sn].OC(=O)C1=CC=CC=C1 KJQZTGPKDPXWBE-UHFFFAOYSA-N 0.000 description 2
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 description 2
- 235000005822 corn Nutrition 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
- 230000002939 deleterious effect Effects 0.000 description 2
- WEBQKRLKWNIYKK-UHFFFAOYSA-N demeton-S-methyl Chemical group CCSCCSP(=O)(OC)OC WEBQKRLKWNIYKK-UHFFFAOYSA-N 0.000 description 2
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 2
- ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 description 2
- 229940013764 fipronil Drugs 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 description 2
- 238000003958 fumigation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 201000003872 goiter Diseases 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 2
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 2
- 229960000521 lufenuron Drugs 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 2
- YFBPRJGDJKVWAH-UHFFFAOYSA-N methiocarb Chemical compound CNC(=O)OC1=CC(C)=C(SC)C(C)=C1 YFBPRJGDJKVWAH-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 2
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000007096 poisonous effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000003222 pyridines Chemical class 0.000 description 2
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000005936 tau-Fluvalinate Substances 0.000 description 2
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 2
- 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 2
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 150000003751 zinc Chemical class 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
- OTLLEIBWKHEHGU-TUNUFRSWSA-N (2R,3S,4S,5S)-2-[(2R,3R,4R,5S,6R)-5-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-4-phosphonooxyhexanedioic acid Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=2N=CN=C(C=2N=C1)N)O[C@@H]1[C@@H](CO)O[C@H](O[C@H]([C@H](O)[C@H](OP(O)(O)=O)[C@H](O)C(O)=O)C(O)=O)[C@H](O)[C@H]1O OTLLEIBWKHEHGU-TUNUFRSWSA-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
- FSJYRLHKLVGCNH-UHFFFAOYSA-N (3-tert-butylphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(C(C)(C)C)=C1 FSJYRLHKLVGCNH-UHFFFAOYSA-N 0.000 description 1
- RZXVEBVXHRSQPO-UHFFFAOYSA-N (5-chloro-1,3-thiazol-2-yl)methylsulfanyl-dimethoxy-sulfanylidene-lambda5-phosphane Chemical compound COP(=S)(OC)SCc1ncc(Cl)s1 RZXVEBVXHRSQPO-UHFFFAOYSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 1
- RURQAJURNPMSSK-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-{[2-(4-ethoxyphenyl)-3,3,3-trifluoropropoxy]methyl}benzene Chemical compound C1=CC(OCC)=CC=C1C(C(F)(F)F)COCC1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 RURQAJURNPMSSK-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-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
- MATNVOCQJRAYPF-UHFFFAOYSA-N 2-(diiodomethyl)-1-[2-(diiodomethyl)-4-methylphenyl]sulfonyl-4-methylbenzene Chemical compound IC(I)C1=CC(C)=CC=C1S(=O)(=O)C1=CC=C(C)C=C1C(I)I MATNVOCQJRAYPF-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-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
- NCDBYAPSWOPDRN-UHFFFAOYSA-N 2-[dichloro(fluoro)methyl]sulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)F)C(=O)C2=C1 NCDBYAPSWOPDRN-UHFFFAOYSA-N 0.000 description 1
- KRMBZNHPORRLSK-UHFFFAOYSA-N 2-chloro-1,3-dinitrobenzene trifluoromethylbenzene Chemical compound FC(C1=CC=CC=C1)(F)F.ClC1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-] KRMBZNHPORRLSK-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-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
- 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 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241001143309 Acanthoscelides obtectus Species 0.000 description 1
- 241000934064 Acarus siro Species 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000059559 Agriotes sordidus Species 0.000 description 1
- 241000218473 Agrotis Species 0.000 description 1
- 241001157812 Alternaria brassicicola Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238679 Amblyomma Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241001435074 Anthomyia Species 0.000 description 1
- 241000254177 Anthonomus Species 0.000 description 1
- 241001414828 Aonidiella aurantii Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000273311 Aphis spiraecola Species 0.000 description 1
- 241000256844 Apis mellifera Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241001289510 Attagenus unicolor Species 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241001490249 Bactrocera oleae Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- 241001142394 Bibio marci Species 0.000 description 1
- 239000005874 Bifenthrin Substances 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000272639 Brachycaudus mimeuri Species 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 1
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 1
- 241001444260 Brassicogethes aeneus Species 0.000 description 1
- 241000982105 Brevicoryne brassicae Species 0.000 description 1
- NYQDCVLCJXRDSK-UHFFFAOYSA-N Bromofos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl NYQDCVLCJXRDSK-UHFFFAOYSA-N 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- PXQCTMPKKDEGNE-UHFFFAOYSA-N C(CCC)NC(OCC#C)=O.[I] Chemical compound C(CCC)NC(OCC#C)=O.[I] PXQCTMPKKDEGNE-UHFFFAOYSA-N 0.000 description 1
- KCMZYCFSSYXEQR-UHFFFAOYSA-N CCCC[K] Chemical group CCCC[K] KCMZYCFSSYXEQR-UHFFFAOYSA-N 0.000 description 1
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical group CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 description 1
- 241000345998 Calamus manan Species 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 241000257163 Calliphora vicina Species 0.000 description 1
- 241000282836 Camelus dromedarius Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical compound CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000259759 Cassida nobilis Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 1
- 241000931705 Cicada Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- PITWUHDDNUVBPT-UHFFFAOYSA-N Cloethocarb Chemical compound CNC(=O)OC1=CC=CC=C1OC(CCl)OC PITWUHDDNUVBPT-UHFFFAOYSA-N 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000771760 Coniosporium <Dothideomycetes incertae sedis> Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- 241000256113 Culicidae Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- YPHMISFOHDHNIV-FSZOTQKASA-N Cycloheximide Natural products C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 239000005644 Dazomet Substances 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 241001481695 Dermanyssus gallinae Species 0.000 description 1
- 241001124144 Dermaptera Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- WGOWCPGHOCIHBW-UHFFFAOYSA-N Dichlofenthion Chemical compound CCOP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl WGOWCPGHOCIHBW-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VBKKVDGJXVOLNE-UHFFFAOYSA-N Dioxation Chemical compound CCOP(=S)(OCC)SC1OCCOC1SP(=S)(OCC)OCC VBKKVDGJXVOLNE-UHFFFAOYSA-N 0.000 description 1
- 108700004685 Drosophila y Proteins 0.000 description 1
- 241001425472 Dysdercus cingulatus Species 0.000 description 1
- 241000223924 Eimeria Species 0.000 description 1
- 239000005894 Emamectin Substances 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241000738498 Epitrix pubescens Species 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 241000283070 Equus zebra Species 0.000 description 1
- 241000917107 Eriosoma lanigerum Species 0.000 description 1
- 241000917171 Eriosomatinae Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 239000005895 Esfenvalerate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000060469 Eupoecilia ambiguella Species 0.000 description 1
- 241001331999 Euproctis Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000005656 Fenazaquin Substances 0.000 description 1
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 241000720914 Forficula auricularia Species 0.000 description 1
- 239000005791 Fuberidazole Substances 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000192128 Gammaproteobacteria Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 241000282575 Gorilla Species 0.000 description 1
- 241000578422 Graphosoma lineatum Species 0.000 description 1
- 241001243091 Gryllotalpa Species 0.000 description 1
- 241000145313 Gymnocorymbus ternetzi Species 0.000 description 1
- 241000790933 Haematopinus Species 0.000 description 1
- 241001659689 Hercinothrips Species 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 241000771999 Hippobosca Species 0.000 description 1
- 241001272567 Hominoidea Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 241001480803 Hyalomma Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- 241000832180 Hylotrupes bajulus Species 0.000 description 1
- 241001508566 Hypera postica Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 241001495069 Ischnocera Species 0.000 description 1
- 241001149911 Isopoda Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 244000001369 Juglans ailantifolia Species 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241000257166 Lucilia cuprina Species 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- NTAHCMPOMKHKEU-AATRIKPKSA-N Methacrifos Chemical compound COC(=O)C(\C)=C\OP(=S)(OC)OC NTAHCMPOMKHKEU-AATRIKPKSA-N 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- 239000005918 Milbemectin Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 241001668536 Oculimacula yallundae Species 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241000168255 Opiliones Species 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- JAYZFNIOOYPIAH-UHFFFAOYSA-N Oxydeprofos Chemical compound CCS(=O)CC(C)SP(=O)(OC)OC JAYZFNIOOYPIAH-UHFFFAOYSA-N 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000721451 Pectinophora gossypiella Species 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000932963 Philopteridae Species 0.000 description 1
- 241001516577 Phylloxera Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000351396 Picea asperata Species 0.000 description 1
- TZBPRYIIJAJUOY-UHFFFAOYSA-N Pirimiphos-ethyl Chemical group CCOP(=S)(OCC)OC1=CC(C)=NC(N(CC)CC)=N1 TZBPRYIIJAJUOY-UHFFFAOYSA-N 0.000 description 1
- 239000005924 Pirimiphos-methyl Substances 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- DTAPQAJKAFRNJB-UHFFFAOYSA-N Promecarb Chemical compound CNC(=O)OC1=CC(C)=CC(C(C)C)=C1 DTAPQAJKAFRNJB-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241001180370 Psylliodes chrysocephalus Species 0.000 description 1
- 241001105129 Ptinus Species 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241001509970 Reticulitermes <genus> Species 0.000 description 1
- 241001481703 Rhipicephalus <genus> Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 241000125162 Rhopalosiphum Species 0.000 description 1
- 241000318997 Rhyzopertha dominica Species 0.000 description 1
- OUNSASXJZHBGAI-UHFFFAOYSA-N Salithion Chemical compound C1=CC=C2OP(OC)(=S)OCC2=C1 OUNSASXJZHBGAI-UHFFFAOYSA-N 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 241000180219 Sitobion avenae Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 240000004535 Sorbus decora Species 0.000 description 1
- 241001674391 Sphaerulina musiva Species 0.000 description 1
- 241000252794 Sphinx Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001494139 Stomoxys Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- 239000005937 Tebufenozide Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- 241001124685 Tenthredinidae Species 0.000 description 1
- BGHCVCJVXZWKCC-UHFFFAOYSA-N Tetradecane Natural products CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- IRVDMKJLOCGUBJ-UHFFFAOYSA-N Thionazin Chemical compound CCOP(=S)(OCC)OC1=CN=CC=N1 IRVDMKJLOCGUBJ-UHFFFAOYSA-N 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 241000339374 Thrips tabaci Species 0.000 description 1
- OTLLEIBWKHEHGU-UHFFFAOYSA-N Thuringiensin Natural products C1=NC=2C(N)=NC=NC=2N1C(C(C1O)O)OC1COC1C(CO)OC(OC(C(O)C(OP(O)(O)=O)C(O)C(O)=O)C(O)=O)C(O)C1O OTLLEIBWKHEHGU-UHFFFAOYSA-N 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 241000031845 Tilletia laevis Species 0.000 description 1
- 241000130771 Tinea pellionella Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- 241001249488 Triatoma sanguisuga Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 239000005942 Triflumuron Substances 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 241001645389 Trombidiidae Species 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 241000514371 Ustilago avenae Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 241000607598 Vibrio Species 0.000 description 1
- 206010047400 Vibrio infections Diseases 0.000 description 1
- 235000011453 Vigna umbellata Nutrition 0.000 description 1
- 240000001417 Vigna umbellata Species 0.000 description 1
- CVQODEWAPZVVBU-UHFFFAOYSA-N XMC Chemical compound CNC(=O)OC1=CC(C)=CC(C)=C1 CVQODEWAPZVVBU-UHFFFAOYSA-N 0.000 description 1
- 241000353223 Xenopsylla cheopis Species 0.000 description 1
- 241000429635 Xestobium rufovillosum Species 0.000 description 1
- 241001466330 Yponomeuta malinellus Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- XHQNHTRJJRRYEP-UHFFFAOYSA-N [P].C(CC)N Chemical compound [P].C(CC)N XHQNHTRJJRRYEP-UHFFFAOYSA-N 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000001467 acupuncture Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- GMAUQNJOSOMMHI-JXAWBTAJSA-N alanycarb Chemical compound CSC(\C)=N/OC(=O)N(C)SN(CCC(=O)OCC)CC1=CC=CC=C1 GMAUQNJOSOMMHI-JXAWBTAJSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 244000000054 animal parasite Species 0.000 description 1
- 239000012874 anionic emulsifier Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000012752 auxiliary agent Substances 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
- RQVGAIADHNPSME-UHFFFAOYSA-N azinphos-ethyl Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OCC)OCC)N=NC2=C1 RQVGAIADHNPSME-UHFFFAOYSA-N 0.000 description 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-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
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229950007134 bromofos Drugs 0.000 description 1
- 229960003168 bronopol Drugs 0.000 description 1
- 235000021329 brown rice Nutrition 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
- 239000001273 butane Substances 0.000 description 1
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- VAYGVODTVNMVPV-UHFFFAOYSA-N carbamic acid;cyclohexanamine Chemical compound NC([O-])=O.[NH3+]C1CCCCC1 VAYGVODTVNMVPV-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XFDJMIHUAHSGKG-UHFFFAOYSA-N chlorethoxyfos Chemical compound CCOP(=S)(OCC)OC(Cl)C(Cl)(Cl)Cl XFDJMIHUAHSGKG-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
- 238000005660 chlorination reaction Methods 0.000 description 1
- QGTYWWGEWOBMAK-UHFFFAOYSA-N chlormephos Chemical compound CCOP(=S)(OCC)SCCl QGTYWWGEWOBMAK-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 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
- 238000013375 chromatographic separation Methods 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- GQDHEYWVLBJKBA-UHFFFAOYSA-H copper(ii) phosphate Chemical compound [Cu+2].[Cu+2].[Cu+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GQDHEYWVLBJKBA-UHFFFAOYSA-H 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- SVOAENZIOKPANY-UHFFFAOYSA-L copper;octadec-9-enoate Chemical compound [Cu+2].CCCCCCCCC=CCCCCCCCC([O-])=O.CCCCCCCCC=CCCCCCCCC([O-])=O SVOAENZIOKPANY-UHFFFAOYSA-L 0.000 description 1
- BXNANOICGRISHX-UHFFFAOYSA-N coumaphos Chemical compound CC1=C(Cl)C(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 BXNANOICGRISHX-UHFFFAOYSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-UHFFFAOYSA-N 0.000 description 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 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
- 230000000881 depressing effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 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
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- VEENJGZXVHKXNB-VOTSOKGWSA-N dicrotophos Chemical compound COP(=O)(OC)O\C(C)=C\C(=O)N(C)C VEENJGZXVHKXNB-VOTSOKGWSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 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
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 210000005069 ears Anatomy 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
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 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 1
- 230000008029 eradication Effects 0.000 description 1
- 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 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 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
- 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
- YOWNVPAUWYHLQX-UHFFFAOYSA-N fluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 YOWNVPAUWYHLQX-UHFFFAOYSA-N 0.000 description 1
- 229950006719 fluazuron Drugs 0.000 description 1
- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- HAWJXYBZNNRMNO-UHFFFAOYSA-N furathiocarb Chemical compound CCCCOC(=O)N(C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 HAWJXYBZNNRMNO-UHFFFAOYSA-N 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- WIFXJBMOTMKRMM-UHFFFAOYSA-N halfenprox Chemical compound C=1C=C(OC(F)(F)Br)C=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 WIFXJBMOTMKRMM-UHFFFAOYSA-N 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- ROASJEHPZNKHOF-UHFFFAOYSA-N hexyl carbamate Chemical compound CCCCCCOC(N)=O ROASJEHPZNKHOF-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-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
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- KLGMSAOQDHLCOS-UHFFFAOYSA-N mecarbam Chemical compound CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC KLGMSAOQDHLCOS-UHFFFAOYSA-N 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 239000002855 microbicide agent Substances 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 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
- 150000002780 morpholines Chemical class 0.000 description 1
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[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 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 description 1
- 229960004816 moxidectin Drugs 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- BUYMVQAILCEWRR-UHFFFAOYSA-N naled Chemical compound COP(=O)(OC)OC(Br)C(Cl)(Cl)Br BUYMVQAILCEWRR-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- PZXOQEXFMJCDPG-UHFFFAOYSA-N omethoate Chemical compound CNC(=O)CSP(=O)(OC)OC PZXOQEXFMJCDPG-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- PMCVMORKVPSKHZ-UHFFFAOYSA-N oxydemeton-methyl Chemical group CCS(=O)CCSP(=O)(OC)OC PMCVMORKVPSKHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000003071 parasitic effect Effects 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
- 229960000490 permethrin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 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
- 150000003904 phospholipids Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 150000004885 piperazines Chemical class 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
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 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
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- 229960002026 pyrithione Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- 230000023882 response to organophosphorus Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-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
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical class N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 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
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229940032912 zephiran Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- 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
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
-
- 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
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及新的式(I)的N-吡唑基苯胺和N-吡唑基氨基吡啶,其制备方法,及其作为杀虫剂的用途,其中R1、R2、R5、R4、X、Y和Z为说明书中给出的定义。
Description
本发明涉及新的N-吡唑基苯胺和N-吡唑基氨基吡啶,其多种制备方法,及其作为害虫防治剂的用途。
已公开了一些N-杂芳基-2-硝基-苯胺,例如N-[1,3-二甲基吡唑-5-基]-2,6-二硝基-4-三氟甲基苯胺和N-[5-三氟甲基-1,3,4-噻二唑-2-基]-2,6-二硝基-4-三氟甲基苯胺,具有杀真菌和杀虫性质(参考:EP-A-0478974,WO93/19054)。可是在一些情况下,特别是以低浓度的活性化合物和低施用剂量使用时,上述活性化合物的活性总不能令人完全满意。
其中
X代表C-NO2、C-卤素、C-卤代烷基或N,
Y代表NO2、CN、卤素或卤代烷基,
Z代表NO2、卤素、卤代烷基、卤代烷氧基或卤代烷硫基,
R1代表氢、或各自可被可选择取代的烷基、链烯基、炔基、芳基、杂芳基或芳烷基,
R2和R3各自独立地代表
氢、卤素、氰基或硝基、或各自可被可选择取代的烷基、芳基或杂芳基、或下述基团之一:CO2R5、CONR6R7、CSNR6R7、S(O)nR8
R4代表氢、各自可被可选择取代的烷基、链烯基、链炔基、芳烷基、芳氧基或芳烷氧基或下述基团之一:SO2NR6R7、SO2R9、COR10或CH2N(R9)w,其中
w代表CO2R5或SO2R5,
R5代表烷基,
R6和R7各自独立地代表氢或烷基、或与和它们相连的N原子一起形成一个环,该环可选择的至少还含有一个杂原子,
R8代表烷基或卤代烷基,
R9代表烷基或可选择取代的芳基,
R10代表烷基、烷氧基、或各自可被可选择取代的芳基或芳氧基,
n代表0、1或2,和
条件是
当
R4代表氢,并且同时
X代表C-NO2,和同时
Y或Z之一代表卤代烷基而另外一个代表NO2时,
R1不代表烷基、可选择取代的苯基、可选择取代的苯基磺酰基或吡啶基,和/或
R2不代表氢、烷基或苯基,和/或
R3不代表氢、CN、卤素、可选择取代的苯基、可选择取代的苯基磺酰基、CO2-烷基或CO2-苄基。
而且,已发现A)式(I)的N-吡唑基苯胺和N-吡唑基氨基吡啶可通过下述方法制备:
在碱存在下和在稀释剂存在下使式(II)的5-氨基吡唑与式(III)的化合物反应,
其中
其中
Hal代表氟、氯、溴或碘,优选氟和氯,和
X、Y和Z为上述定义
且如果适合,在碱存在下和如果适合在稀释剂存在下,接着使所得的式(Ia)化合物与式(IV)化合物反应
其中
X、Y、Z、R1、R2、和R3为上述定义
R11-V (IV)
其中
V代表阴离子离去基团,例如氯、溴、碘、乙酰氧基、甲苯磺酰基或甲磺酰基,和
R11为上述除去氢之外的R4的定义;和
B)通过下述方法制备式(Ib)化合物:
其中
R1、R2、R3、X、Y和Z为上述定义,和
R11为上述定义
在碱存在下和在稀释剂存在下,使式(II)的5-氨基吡唑与式(IV)的化合物反应
其中
R1、R2和R3为上述定义
R11-V (IV)
其中
R11和V为上述的定义
其中
其中Hal、X、Y和Z为上述定义。
新的式(I)化合物所具有的性质使得它们可用作农药。特别的,它们可用作杀虫剂、杀节肢动物剂和杀真菌剂。
式(I)提供了根据本发明的N-吡唑基苯胺和N-吡唑基氨基吡啶的总的定义。
在本文上述和下述给出的通式中的优选取代基,或基团范围将在下文中例示。
X优选代表C-NO2、C-卤素、C-C1-C6-卤代烷基或N。
Y优选代表NO2、CN、卤素或C1-C6-卤代烷基。
Z优选代表NO2、卤素、C1-C6-卤代烷基、C1-C6-卤代烷氧基或C1-C6-卤代烷硫基。
R1优选代表氢、C1-C8-烷基、C1-C8-氰基烷基、C1-C8-卤代烷基、C1-C8-羟烷基、C1-C4-烷氧基-C1-C8-烷基、或代表苯基或苯乙基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基、苯基、苯氧基、CN或NO2,或代表吡啶基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-烷氧基或C1-C4-卤代烷基,或代表嘧啶基、噻二唑基或噻唑基,其各自可被下述相同或不同的取代基可选择的单取代至二取代:卤素、C1-C4-烷基、C1-C4-烷氧基或C1-C4-卤代烷基。
R2和R3各自独立地优选代表
氢、卤素、氰基、硝基、C1-C8-烷基、C1-C8-卤代烷基、C1-C8-羟烷基、C1-C4-烷氧基-C1-C8-烷基、
或代表苯基或噻吩基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基或C1-C4-卤代烷硫基,或下述基团之一:CO2R5、CONR6R7、CSNR6R7、S(O)nR8。
R4优选代表氢、C1-C8-烷基、C1-C8-卤代烷基、C1-C8-羟烷基、C1-C4-烷氧基-C1-C8-烷基、C3-C8-链烯基、C3-C8-卤代链烯基、C3-C8-羟链烯基、C1-C4-烷氧基-C3-C8-链烯基、C3-C8-链炔基、C3-C8-卤代链炔基、C3-C8-羟链炔基、C1-C4-烷氧基-C3-C8-链炔基、或代表苯氧基、苄基或苄氧基、其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基或C1-C4-卤代烷氧基,或代表下述基团之一:SO2R9、COR10、CH2N(R9)w、SO2NR6R7。
w优选代表CO2R5或SO2R5。
R5优选代表C1-C8-烷基。
R6和R7各自独立的优选代表氢或C1-C8-烷基、或与和它们相连的N原子一起形成一个5-至7-元环,该环可选择的至少还含有另外两个杂原子,杂原子由N、O和S组成。
R8优选代表C1-C8-烷基或C1-C8-卤代烷基。
R9优选代表C1-C8-烷基或代表苯基,其可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基或C1-C4-烷氧基。
R10优选代表C1-C8-烷基或C1-C8-烷氧基、或代表苯基或苯氧基,其各自可被卤素、C1-C4-烷基或C1-C4-烷氧基可选择的单取代至三取代。
n优选代表0、1或2。
X特别优选代表C-NO2、C-氟、C-氯、C-溴、或具有1至5个相同或不同的卤原子的C-C1-C3-卤代烷基,卤原子由氟、氯和溴组成,或代表N。
Y特别优选代表NO2、CN、氟、氯、溴或具有1至7个相同或不同的卤原子的C1-C4-卤代烷基,卤原子由氟、氯和溴组成。
Z特别优选代表NO2、氟、氯、溴、各自具有1至7个相同或不同的卤原子的C1-C4-卤代烷基、C1-C4-卤代烷氧基或C1-C4-卤代烷硫基,卤原子由氟、氯和溴组成。
R1特别优选代表各自具有一至三个相同或不同的卤原子的C1-C6-烷基、C1-C6-氰基烷基、C1-C6-卤代烷基、卤原子由氟、氯和溴组成,或代表C1-C6-羟烷基、C1-C2-烷氧基-C1-C6-烷基、
或代表苯基、苄基或苯乙基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、C1-C3-烷基、C1-C3-烷氧基、各自具有一至三个相同或不同的卤原子的C1-C3-卤代烷基、C1-C3-卤代烷氧基或C1-C4-卤代烷硫基、卤原子由氟、氯和溴组成,或CN或硝基,
或代表吡啶基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、C1-C3-烷基、C1-C3-烷氧基或具有一至三个相同或不同的卤原子的C1-C3-卤代烷基,其中的卤原子由氟、氯和溴组成,或代表嘧啶基或噻二唑基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴,C1-C3-烷基、C1-C3-烷氧基和具有一至三个相同或不同的卤原子的C1-C3-卤代烷基,其中的卤原子由氟、氯和溴组成。
R2和R3各自独立地特别优选代表
氢、氟、氯、溴、氰基、C1-C6-烷基、具有一至六个相同或不同的卤原子的C1-C6-卤代烷基、其中卤原子由氟、氯和溴组成,或代表C1-C2-烷氧基-C1-C6-烷基、或代表苯基或噻吩基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、C1-C3-烷基或C1-C3-烷氧基,或代表下述基团之一:CO2R5、CONR6R7、CSNR6R7、S(O)nR8。
R4特别优选代表氢、或代表C1-C6-烷基、C3-C6-链烯基或C3-C6-链炔基,其各自可被一至三个由氟、氯和溴组成的卤原子可选择的取代,或代表C1-C4-烷氧基甲基、
或代表苄基或苄氧基、其各自可被氟、氯或溴可选择地单取代至二取代,或代表下述基团之一:SO2R9、COR10、CH2N(R9)CO2R5。
R5特别优选代表C1-C4-烷基。
R6和R7各自独立的特别优选代表氢、甲基或乙基。
R8特别优选代表C1-C4-烷基或具有一至三个氟和/或氯原子的C1-C4-卤代烷基。
R9特别优选代表C1-C4-烷基,或代表苯基,其可被氟、氯和/或溴可选择地单取代至三取代。
R10特别优选代表C1-C4-烷基、或代表苯基,其可被氟、氯和/或溴可选择的单取代至三取代。
n特别优选代表0、1或2,
X更特别优选代表C-NO2、C-Cl或N。
Y更特别优选代表NO2、CN、氟、氯或CF3。
Z更特别优选代表NO2、氟、氯、CF3、OCF3或SCF3。
R1更特别优选代表甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基的各种异构体或己基的各种异构体,它们各自可选择的被氟和/或氯单取代至三取代或被氰基单取代,
或代表苯基、苄基或苯乙基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、CF3、OCF3、SCF3、CN和NO2,或代表吡啶基、嘧啶基或噻二唑基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴或CF3。
R2和R3各自独立地更特别优选代表
氢、氯、溴、CN、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、CF3、C2F5或CH2OCH3、
或代表苯基,其可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、甲基或甲氧基,或代表下述基团之一:CO2R5、CONR6R7或S(O)nR8。
R4更特别优选代表氢、甲基、乙基、2-丙烯基、2-丙炔基、甲氧基甲基、乙氧基甲基、丙氧基甲基、异丙氧基甲基或正丁氧基甲基。
R5更特别优选代表甲基或乙基。
R6和R7更特别优选地代表氢。
R8更特别优选代表甲基、乙基、三氟甲基、1,1-二氟乙基或2,2,2-三氟乙基。
n更特别优选代表0、1或2,
下述在各种情况下都适用:
如果
R4代表氢且同时
X代表C-NO2和同时
Y或Z之一代表卤代烷基而另一个取代基代表NO2,则
R1不代表烷基、可选择取代的苯基、可选择取代的苯基磺酰基或吡啶基和/或
R2不代表氢、烷基或苯基和/或
R3不代表氢、CN、卤素、可选择取代的苯基、可选择取代的苯基磺酰基、CO2-烷基或CO2-苄基。
优选的一组化合物是式(I-1)化合物
其中
R1、R2、R3、R4、X、Y和Z为上述定义,
条件是
如果
R4代表氢和同时
X代表C-NO2和同时
Y或Z之一代表卤代烷基而另外一个取代基代表NO2,则
R1不代表烷基、可选择取代取代的苯基、可选择取代的苯基磺酰基或吡啶基和/或
R2不代表氢、烷基或苯基和/或
R3不代表氢、CN、卤素、可选择取代的苯基、可选择取代的苯基磺酰基,CO2-烷基或CO2-苄基。
其中
X1具有上述X的定义,但X为C-NO2除外和
R1、R2、R3、R4、Y和Z为上述定义,
条件是
如果Z代表NO2,Y不代表NO2。
其中
X1具有上述的定义,
Y1具有上述Y的定义,但Y为NO2除外和
R1、R2、R3、R4和Z为上述定义。
在通式或在优选范围中的上述基团定义或例示可根据需要彼此组合,即在每个范围和优选范围之间的组合也是可能的。上述原则适用于终产物且类似的适用于前体和中间体。
本发明优选的式(I)、(I-1)、(I-2)和(I-3)化合物是各自包含上述例示的优选定义组合的那些化合物。
本发明特别优选的式(I)、(I-1)、(I-2)和(I-3)化合物是各自包含上述例示的特别优选定义组合的那些化合物。
本发明更特别优选的式(I)、(I-1)、(I-2)和(I-3)化合物是各自包含上述例示的更特别优选定义组合的那些化合物。
在本发明化合物的定义中已述及的烃基如烷基,在尽可能的情况下,各自为直链或支链的烷基,其也可与杂原子连接,如烷氧基。
进行本发明方法所需的起始物式(II)的5-氨基吡唑是已知的和/或可通过已知方法制备(例如参考:Chem.Het.Comp.17(1981),1;J.Org.Chem.21(1956),1240;EP0201852;EP0392241;Chem.Ber.95(1962),2871;J.Org.Chem.29(1964)1915;Isv.Attad.Nauk SSR,Ser.Khim 11(1990)2583;J.Chem.Research(5),1993,76)。
进行本发明方法所需的起始物式(III)的化合物是已知的和/或可通过已知方法制备(例如参考:EP0398499,J.Org.Chem.47(1982)2856;US3888932;US3928416)。
进行本发明方法所需的起始物式(IV)的化合物是有机化学中已知的物质。
下述的资料是在本发明方法中,可选择的方法A)和B)的各种步骤中使用的。
根据本发明的制备新的式(I)化合物的方法优选在稀释剂存在下进行,适合的稀释剂基本上是各种惰性有机溶剂。上述稀释剂优选包括可选择卤代的脂肪族和芳香烃,如戊烷、己烷、庚烷、环己烷、石油醚、汽油、石油英、苯、甲苯、二甲苯、二氯甲烷、二氯乙烷、氯仿、四氯化碳、氯苯、邻二氯苯,醚类如乙醚和二丁基醚、乙二醇二甲基醚和二乙二醇二甲基醚、四氢呋喃和二噁烷,酮类如丙酮、甲基乙基酮、甲基异丙基酮和甲基异丁基酮,酯类如乙酸甲酯和乙酸乙酯,腈类如乙腈和丙腈,酰胺类如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,以及二甲基亚砜、环丁砜和六甲基磷酰三胺。
在本发明的方法中可使用的碱是在这种类型的反应中常规使用的各种酸束缚剂。优选适合的是:碱金属氢化物和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氢氧化物和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属碳酸盐,碱土金属碳酸盐,碱金属碳酸氢盐和碱土金属碳酸氢盐,如碳酸钠、碳酸氢钠、碳酸钾或碳酸氢钾、以及碳酸钙,碱金属乙酸盐,如乙酸钠和乙酸钾,碱金属醇化物,如叔丁基钠和叔丁基钾,还有碱性氮化合物,如三甲胺、三乙胺、三丙基胺、三丁基胺、二异丁基胺、二环己基胺、乙基二异丙基胺、乙基二环己基胺、N,N-二甲基苄基胺、N,N-二甲基-苯胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2,4-二甲基、2,6-二甲基-、2-乙基、4-乙基-和5-乙基-2-甲基-吡啶、1,5-二氮杂二环[4,3,0]-壬-5-烯(DBN)、1,8-二氮杂二环-[5,4,0]-十一碳-7-烯(DBU)和1,4-二氮杂二环[2,2,2]-辛烷(DABCO)。
在本发明的方法中的反应温度可在相当宽的范围内变化。反应通常在0℃至100℃,优选10℃至80℃的温度下进行。
本发明的方法通常在大气压力下进行。可是也可在提高或降低的压力下进行。
为了进行本发明的方法,在各种情况下通常使用大约等摩尔量的起始物。可是,在一些情况下,还可使两种成分中的一种过量。通常,反应在酸束缚剂存在下在适合的稀释剂中进行,并在所需的反应温度下搅拌反应混合物数小时。在本发明的方法中,通过常规的方法进行加工处理(参考:制备实施例)。
本发明的式(I)化合物可用作杀虫剂。害物是有害的动物,特别是对植物或高等动物有害的昆虫和螨类。
本发明的活性化合物适合防治有害动物,并具有良好的植物耐受性和对温血动物的低毒性,动物优选节肢动物,特别是在农业、森林业、储藏产品和材料的保护和卫生领域中遇到的昆虫和螨类。它们对正常敏感和抗性品系以及对所有或一些发育阶段都有活性。上述有害动物包括:
等足目:例如,潮虫、平甲虫和带鼠妇。
倍足目:例如,具斑马陆。
唇足目:例如,食果地蜈蚣和蚰蜒。
综合目:例如,庭园么蚰。
缨尾目:例如,西洋衣鱼。
弹尾目:例如,具刺跳虫。
直翅目:例如,东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国小蠊、家蟋蟀、蝼蛄属、热带飞蝗、长额负蝗和蚱蜢。
革翅目:例如,欧洲球螋。
等翅目:例如,犀白蚁属。
虱目:例如,体虱、血虱属和颚虱属。
食毛目:例如,羽虱和啮虱。
缨翅目:例如,温室条蓟马和烟蓟马。
半翅目:例如,褐盾蝽、棉红蝽、甜菜拟网蝽、臭虫、长红蜡蝽和吸血猎蝽。
同翅目:例如,甘蓝粉虱、棉粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶鹿隐瘤额蚜、甜菜蚜、苹果蚜、苹果绵蚜、桃大尾蚜、麦长管蚜、桃蚜属、忽布瘤额蚜、粟缢管蚜、美核桃根瘤蚜、瘿绵蚜属、叶蝉属、纹叶蝉、黑尾叶蝉、李蜡蚧、揽珠蜡蚧、灰飞虱、褐飞虱、红圆蚧、春藤园盾蚧、粉蚧属和木虱属。
鳞翅目:例如,红铃虫、松天蛾、冬天蛾、苹果细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜叶蛾、桔潜叶蛾、地老虎属、切根虫属、褐夜蛾、实夜蛾属、棉铃虫属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、黏虫属、粉纹夜蛾、苹果蠹蛾、粉蝶属、螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织夜蛾、亚麻黄卷蛾、烟卷蛾、云杉卷夜蛾、葡萄果蠹蛾、茶长卷夜蛾和栎纵卷夜蛾。
鞘翅目:例如,具斑窃蠹、谷蠹、大豆象、家天牛、赤杨紫跳甲、萤叶甲、马铃薯甲虫、蜡根猿叶甲、条叶甲属、油菜跳甲、墨西哥豆瓢虫、隐金甲属、锯谷盗、花象甲属、谷象属、葡萄黑耳象、香蕉根叶甲、甘蓝荚象甲、苜蓿叶象甲、肾斑皮蠹、皮蠹属、黑皮蠹属、圆皮蠹、黑毛皮蠹、粉蠹属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、金针虫属、金龟、六月金龟和新西兰肋翅鳃角金龟。
膜翅目:例如,松叶蜂、叶蜂属、蚁属、厨蚁和胡蜂属。
双翅目:例如,伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厩蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、螫蝇属、鼻蝇属、皮蝇属、虻属、螗蜩、花园毛蚊、瑞典麦杆蝇、麦花蝇属、甜菜潜叶蝇、地中海实蝇、油橄榄实蝇和欧洲大蚊。
蚤目:例如,东方鼠蚤和蚤。
蛛形纲:例如,蝎和盗蛛和黑寡妇球腹蛛。
蜱螨目:例如,粗脚粉螨、隐喙蜱、钝喙蜱属、鸡皮刺螨、兔瘿螨、桔锈螨、牛蜱属、头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属、皮痒螨属、疥螨属、附线螨属、苜蓿苔属螨、全爪螨属、红叶螨属和Hemitarsonemus spp。
本发明的活性化合物还具有杀真菌活性,并在植物保护中可用作杀真菌剂,例如,防治水稻稻瘟病的致病微生物(Pyricularia oryzae)。
在植物保护中,本杀菌剂可用来杀灭根肿病菌纲、卵菌纲、弧菌纲、接合菌亚纲、子囊菌纲、担子菌纲和半知菌纲的微生物。
下述以非限定的方式列举了上述系统命名下的一些真菌病害的致病微生物:
腐霉属,例如:甘薯斑腐病;
疫病属,例如:马铃薯晚疫病;
假霜霉属,例如:律草假霜霉或生姜腐败病;
单轴霉属,例如:葡萄霜霉病;
霜霉菌属,例如:豌豆霜霉或大白菜霜霉病;
白粉菌属,例如:葫芦白粉病;
球壳霉属,例如:黄瓜白粉病;
足球霉属,例如:苹果白粉病;
黑星菌属,例如:苹果黑星病;
核腔菌属,例如:大麦网斑病或大麦条纹病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
旋孢霉素属,例如:稻胡麻斑病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
单孢锈菌属,例如:菜豆锈病;
双孢锈菌属,例如:小麦叶锈病;
腥黑粉菌属,例如:小麦网腥黑穗病;
黑粉菌属,例如:裸黑粉菌或燕麦散黑穗病;
薄膜霉属,例如:稻纹枯病;
梨孢霉属,例如:稻瘟病;
镰刀霉属,例如:禾杆镰孢菌;
葡萄孢属,例如:灰葡萄孢;
壳针孢霉属,例如:小麦颍枯病;
细球壳菌属,例如:小麦白叶斑病;
尾孢霉属,例如:小豆褐斑病;
交链孢属,例如:甘蓝黑斑病和
葡萄假尾孢霉属,例如:Pseudocercosporella herpotrichoides。
植物对消灭植物病害所需浓度的活性化合物的良好的耐受性,使得用其处理植物的地上部分、植物的繁殖原种和种子,以及植物生长的土壤成为可能。
在本文中,可使用本发明的活性化合物非常有效地防治果树和蔬菜栽培中的病害,如防治苹果黑星病的致病微生物(苹果黑星菌)。另外,本发明的活性化合物具有好的在体外的活性。
在用作杀虫剂、杀螨剂和杀真菌剂时,本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与其它活性化合物的混合物的形式存在,其它活性化合物如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂。例如,杀虫剂包括:磷酸酯、氨基甲酸酯、羧酸酯、卤代烃类、苯基脲类和从微生物中生产的物质等。
可述及的为下述化合物:
氟酯菊酯、甲体氯氰菊酯、氟氯氰菊酯、氟氯菊酯、brofenprox、顺-苄呋菊酯、clocythrin、乙氰菊酯、β-氟氯氰菊酯、三氟氯氰菊酯、氯氰菊酯、溴氰菊酯、高氰戊菊酯、醚菊酯、分扑菊酯、氰戊菊酯、氟氰戊菊酯、氟胺氰菊酯、α-三氟氯氰菊酯、氯菊酯、反灭菊酯、除虫菊、silafluofen、四溴菊酯、zetamethrin,
棉铃威、恶虫威、丙硫克百威、全杀威、丁叉威、西维因、杀螟丹、苯虫威、fenobucarb、双氧威、异丙威、灭虫威、灭多威、metolcarb、甲叉丙威、抗蚜威、猛杀威、残杀威、叔丁威、硫双灭多威、特铵叉威、三甲威、二甲威、xylylcarb,
乙酰甲胺磷、谷硫磷、乙基谷硫磷、溴硫磷、硫线磷、三硫磷、毒虫威、氯甲磷、毒死蜱、甲基毒死蜱、杀螟腈、内吸磷、甲基内吸磷、甲基内吸磷S赶磷酸酯、二嗪农、敌敌畏、dicliphos、除线磷、百治磷、乐果、甲基毒虫威、敌杀磷、乙拌磷、克瘟散、乙硫磷、氯嘧啶磷、杀螟松、倍硫磷、地虫磷、安果、庚虫磷、iprobenfos、异唑磷、异恶唑磷、甲拌磷、马拉硫磷、灭蚜磷、速灭磷、甲丙硫磷、虫螨畏、杀扑磷、甲胺磷、二溴磷、氧化乐果、砜吸磷、oxydeprofos、对硫磷、甲基对硫磷、稻丰散、伏杀磷、亚胺硫磷、磷胺、辛硫磷、乙基虫螨磷、虫螨磷、丙虫磷、丙硫磷、发果、吡唑硫磷、哒嗪硫磷、喹硫磷、salithion、克线丹、治螟磷、乙丙硫磷、杀虫威、双硫磷、甲基乙拌磷、治线磷、敌百虫、三唑磷、蚜灭多,
噻嗪酮、Lufenuron、定虫隆、氟脲杀、氟螨脲、氟虫脲、氟铃脲、蚊蝇磷、tebufenozide、氟虫隆、triflumuron,
咪蚜胺、nitenpyram,
齐墩螨素(abamectin)、虫螨醚、齐墩螨素(avermectin)、azadirachtin、杀虫磺、苏云菌亚孢杆菌、灭蝇胺、杀螨隆、齐墩螨素(emamectin)、醚菊酯、fenpyrad、fipronil、flufenprox、lufenuron、多聚甲醛、milbemectin、pymetrozin、tebufenpyrad、三唑磷、
涕灭威、恶虫威、丙硫克百威、呋喃丹、丁硫克百威、chlorethoxyfos、cloethocarb、乙拌磷、ethophrophos、氯嘧啶磷、克线磷、fipronil、地虫磷、噻唑硫磷、呋线威、六六六、异唑磷、丙胺磷、灭虫威、久效磷、甲叉丙威、甲拌磷、辛硫磷、丙硫磷、吡唑硫磷、克线磷、silafluofen、tebupirimiphos、七氟菊酯、特丁磷、硫双灭多威、thiafenox,
唑环锡、哒螨酮、四螨嗪、三环锡、杀螨隆、乙硫磷、喹螨醚、杀螨锡、苯硫威、fenpyrad、唑螨酯、氟啶胺、fluazuron、氟螨脲、氟虫脲、氟胺氰菊酯、
fubfenprox、噻螨酮、杀扑磷、moxidectin、伏杀磷、溴丙磷、哒螨酮、pyrimidifen、tebufenpyrad、thuringiensin、triarathene、triazophos、
和下式的化合物
可述及的杀真菌剂为下述:
亚磺酰胺类,如苯氟磺胺(Euparen)、对甲抑菌灵(Methyleuparen)、灭菌丹、氟灭菌丹(fluorofolpet);
苯并咪唑类,如多菌灵(MBC)、苯菌灵、麦穗宁、涕必灵及其盐;
硫氰酸酯类,如清菌噻唑(TCMTB)、巯苯噻唑(MBT);
季铵化合物,如氯化苄基二甲基十四烷铵、氯化苄基-苄基-十二烷铵、氯化十二烷基-二甲基铵;
吗啉衍生物,如C11-C14-4-烷基-2,6-二甲基-吗啉同系物(克啉菌)、(±)-顺-4-[叔丁基苯基-2-甲基丙基]-2,6-二甲基吗啉(丁苯吗啉)、falimorph;
苯酚类,如对苯基苯酚、三溴苯酚、四氯苯酚、五氯苯酚、3-甲基-4-氯苯酚、双氯苯酚、氯酚或其盐;
氮杂茂环类,如唑菌酮、唑菌醇、双苯三唑醇、丙环唑、五环唑、己唑醇、丙氯灵、环唑醇、1-(2-氯苯基)-2-(1-氯环丙基)-3-(1,2,4-三唑-1-基)-丙-2-醇或1-(2-氯苯基)-2-(1,2,4-三唑-1-基-甲基)-3,3-二甲基-丁-2-醇。
碘炔丙基衍生物,如碘炔丙基丁基-氨基甲酸酯(IPBC)、碘丙炔基氯苯基缩甲醛、碘丙炔基苯基氨基甲酸酯、碘丙炔基己基氨基甲酸酯、碘丙炔基环己基胺氨基甲酸酯、碘丙炔基-氧乙基苯基氨基甲酸酯;
碘衍生物,如二碘甲基-对甲苯基砜;
溴衍生物如溴硝丙二醇;
异噻唑啉类,如N-甲基异噻唑啉-3-酮、5-氯-N-辛基异噻唑啉-3-酮、4,5-二氯-N-辛基异噻唑啉-3-酮、N-辛基异噻唑啉-3-酮;
苯并异噻唑啉酮类、环戊烯异噻唑啉类;
吡啶类,如1-羟基-2-吡啶硫酮(及其钠、铁、锰或锌盐)、四氯-4-甲基磺酰基吡啶;
金属皂类,如环烷酸锡、辛酸锡、2-乙基己酸锡、油酸锡、磷酸锡、苯甲酸锡、环烷酸铜、辛酸铜、2-乙基己酸铜、油酸铜、磷酸铜、苯甲酸铜、环烷酸锌、辛酸锌、2-乙基己酸锡、油酸锡、磷酸锡、苯甲酸锡、氧化物,如TBTO,Cu2O
CuO,ZnO;
有机锡化合物,如环烷酸三丁基锡和氧化三丁基锡;
二烷基二硫代氨基甲酸盐类,如二烷基二硫代氨基甲酸的钠和锌盐,四甲基秋兰姆二硫化物(福美双);
腈类,如2,4,5,6-四氯异邻苯二甲腈(百菌清)和其它的具有活化卤素基团的杀微生物剂,如氯乙酸、百亩威、tectamer、溴硝二丙醇、bromidox;
苯并噻唑类,如2-巯基苯并噻唑;棉隆;
喹啉类,如8-羟基喹啉;
释放甲醛的化合物,如苄基醇、单(聚)半缩醛、恶唑啉、六氢-s-三嗪、N-甲基氯乙酰胺;
三-N-(环己基二氮烯翁二氧)-铝、N-(环己基二氮烯翁二氧)-三丁基锡或K盐、双-(N-环己基)二氮杂烯翁-(二氧-铜或-铝)。
本发明的活性化合物可以其市售制剂和从上述制剂制备的应用形式,以及与增效剂的混合物的形式存在,增效剂是能够增加活性化合物活性,但加入的增效剂本身不一定有活性的化合物。
从市售制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。使用形式中活性化合物的浓度为0.0000001至95%重量的活性化合物,优选0.0001至1%重量。
本化合物以适用于使用形式的常规方法进行使用。
根据本发明的化合物还特别适合处理植物和生产的繁殖材料,例如,谷物、玉米、蔬菜等的种子,或它们的球茎、插条等。
当用来防治卫生害虫和储藏产品的害虫时,在木材和粘土上,本活性化合物具有极好的残留活性以及对碱性石灰基质的好的稳定性。
本活性化合物可以其制剂形式或通过进一步稀释上述制剂制备的应用形式使用,使用形式如现用液剂、悬浮剂、乳剂、粉剂、糊剂和颗粒剂。它们可以常规方式使用,例如,通过泼浇、喷雾、弥雾、撒播的方式使用。
根据本发明的活性化合物可在植物萌发前或萌发后使用。
还可将它们在播种前混入土壤。
活性化合物的使用量可在很宽的范围内。使用量根据所需效果的性质而决定。通常,使用量为每公顷土壤表面10g至10Kg活性化合物,优选每公顷50g至5Kg活性化合物。
为了制备杀虫剂,将根据本发明的活性化合物,根据其特定的物理和/或化学性质,转化成为常规的制剂,如液剂,乳剂,悬浮剂,粉剂,泡沫剂,糊剂,颗粒剂,气雾剂,用活性化合物浸渍的天然和合成材料,在聚合物中的微细胶囊和种子包衣组合物,用于燃烧设备的制剂,如熏蒸筒、熏蒸罐和熏蒸盘管等,以及超低容量冷弥雾剂和热弥雾剂。
这些制剂是以已知方法生产的,例如,通过将活性成分与填充剂,即液体溶剂、加压下液化的气体和/或固体载体混合而生产,制剂中可选择的可使用表面活性剂,即乳化剂和/或分散剂,和/或成泡剂。在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘,氯代芳烃类或氯代脂肪烃类,如氯苯,二氯乙烷或二氯甲烷,脂肪烃类,如环己烷或烷属烃,例如矿物油馏份,醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水;液化气体填充剂或载体意为在室温下是气体的加压液体,例如气雾推进剂,如卤代烃类以及丁烷,丙烷,氮和二氧化碳;适当的固体载体有:例如,天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机的合成颗粒和有机粉末,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎;适当的乳化剂和/或成泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如木质素亚磺酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它的粘着剂可以是矿物油和植物油。
可能使用的着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物如金属盐,例如,铁、锰、硼、铜、钼和锌盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5%-90%的活性化合物。
本发明的活性化合物不仅对植物害虫、卫生领域害虫和储藏产品害虫具有活性,而且在兽医领域,对防治动物寄生虫也有活性,动物寄生虫例如scaly ticks、隐缘蜱科、马痒螨、恙螨科;蝇(叮咬和吸食)、寄生性蝇幼虫、虱目、头虱、鸟虱和蚤目。例如它们对蜱(微小牛蜱)表现出极突出的活性。
本发明使用的式(I)的活性化合物也适用于防治侵扰农业家畜的节肢动物,农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂,其它家养动物,例如狗、猫、笼养鸟和水族馆的鱼,还有所谓的试验动物,例如田鼠、豚鼠、大鼠和小鼠。通过防治上述节肢动物,旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等),因此,通过使用本发明的活性化合物,可以使畜牧业更经济、更简单。
在兽医部门,本发明的活性化合物可用已知方法给药,即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、饲养过程和栓剂等形式进行;非经肠给药(肌肉注射、皮下注射、静脉注射、腹膜内注射等)、植入法;经鼻给药;经皮给药,例如以浸泡或洗浴、喷雾、泼上或擦上、洗涤和撤粉形式进行,也可借助于还有活性化合物的成型制品,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等。
本发明的组合物除了至少含有一种通式(I)的化合物外,如果需要,除了填充剂和助剂外,优选至少含有一种表面活性剂。
除非另外指明,所有的百分比都以重量计。
根据本发明的式(I)化合物的制备,将通过下述制备实施例例示。
制备实施例:
将1.2g(0.04mol)的NaH(80%分散于矿物油中)倒入20ml的DMF中,加入5.3g(0.02mol)的1-(4-氯苯基)-3-硫甲基-4-氰基-5-氨基吡唑。加入5.0g(0.02mol)的3,4,5-三氯苯并三氟化物,在80℃下加热混合物18小时。将反应混合物加入到已倒入10ml冰醋酸的300ml水中,接着用二氯甲烷(3×100ml)提取上述混合物。干燥合并的有机相,在减压下除去溶剂,剩余物在硅胶上用二氯甲烷作为洗脱剂进行色谱分离。获得4.5g(理论值的47%)的N-[1-(4-氯苯基)-3-硫甲基-4-氰基吡唑-5-基]-2,6-二氯-4-三氟甲基苯胺。
M.p.:135℃。
实施例2
将1.14g(0.038mol)的NaH(80%分散于矿物油中)倒入100ml的THF中,并分批加入6.0g(0.019mol)的1-(4-氯苯基)-3-硫甲基-4-氰基-5-氨基吡唑。接着滴加4.3g(0.020mol)的2,3-二氯-5-三氟甲基吡啶,并将混合物回流18小时。冷却反应混合物并倒入已加入10ml冰醋酸的300ml冰水中,通过吸滤过滤黄色沉淀。获得6.5g(理论值的75%)的N-[1-(4-氯苯基)-3-硫甲基-4-氰基吡唑-5-基]-2-氨基-3-氯-5-三氟甲基吡啶。
M.p.194℃
将0.35g(0.0116mol)的NaH(80%分散于矿物油中)倒入50ml的THF中,并连续加入3.0g(0.0058mol)的N-(1-甲基-3-五氟乙基-4-三氟甲基吡唑-5-基)-2,6-二硝基-4-三氟甲基苯胺的10mlTHF溶液和1.1g(0.0116)的氯甲基乙基醚。回流反应混合物2小时,冷却并倒入400ml的冰水中。通过吸滤过滤掉已分离的沉淀并干燥。获得2.9g(理论值的86%)的N-乙氧基甲基-N-(1-甲基-3-五氟乙基-4-三氟甲基吡唑-5-基)-2,6-二硝基-4-三氟甲基苯胺。
M.p.:103℃。
类似的和根据一般的指导可获得下述式(I-1)的化合物。表1续表续表续表续表续表续表续表续表续表续表续表续表续表续表续表续表续表续表 *C6H5=苯基 =PhBu =丁基Pr =丙基Et =乙基应用实施例在下述应用实施例中,使用以下例示的化合物作为对比物质:化合物(A),公开于EP0478974化合物(B),公开于WO93/19054
实施例A
辣根猿叶甲幼虫试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸沾在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用辣根猿叶甲幼虫(Phaedoncochlearia)侵染。
在一段确定的时间后,确定死亡%。100%意为所有猿叶甲幼虫被杀死;0%意为没有猿叶甲幼虫被杀死。
在此试验中,3天后,例如用制备实施例10、11、37、44、47、60、71、73和75的活性化合物,用0.01%的活性化合物的试验浓度,死亡率为100%,同时用已知的化合物(A)和(B)处理,结果无损伤。
实施例B
菜蛾试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸沾在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用菜蛾幼虫(P1utellamaculipennis)侵染。
在一段确定的时间后,确定死亡%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,3天后,例如用制备实施例13、60、61和75的化合物,用0.001%的活性化合物的试验浓度,死亡率至少为80%,同时用已知的化合物(A)和(B)处理,结果无损伤。
实施例C
夜蛾试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝叶(Brassica oleracea)浸沾在所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用菜蛾幼虫(Spodopterafrugiperda)侵染。
在一段确定的时间后,确定死亡%。100%意为所有幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,3天后,例如用制备实施例8、11、12、13、28、30、31、32、60、74和89的化合物,用0.1%的活性化合物的试验浓度,死亡率为100%,同时用已知的化合物(A)处理,结果无损伤。
实施例D
叶蝉试验
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,并用水稀释浓缩物至所需浓度。
将水稻秧苗(Oryza sativa)浸沾于所需浓度的活性化合物的制剂中,进行处理,在叶面保持湿润的情况下用黑尾叶蝉(Nephotettixcincticeps)侵染。
在一段确定的时间后,确定死亡%。100%意为所有叶蝉被杀死;0%意为没有叶蝉被杀死。
在此试验中,6天后,例如用制备实施例22、60和63的化合物,用0.1%的活性化合物的试验浓度,死亡率为100%,同时用已知的化合物(A)和(B)处理,结果无损伤。
实施例E
红叶螨试验(有机磷抗性)
溶剂: 7重量份的 二甲基甲酰胺
乳化剂: 1重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和预定量的乳化剂混合,并用含有乳化剂的水稀释浓缩物至所需浓度。
将用各种发育期的温室红叶螨(Tetranychus urticae)严重侵染的菜豆(Phaseolus vulgaris),浸沾于所需浓度的活性化合物的制剂中。
在一段确定的时间后,确定有效%。100%意为所有红叶螨被杀死;0%意为没有红叶螨被杀死。
在此试验中,7天后,例如用制备实施例8、13、28和60的化合物,用0.01%的活性化合物的试验浓度,死亡率为100%,同时用已知的化合物(A)和(B)处理,结果无损伤。
实施例F
霜霉病试验(葡萄)/保护作用
溶剂: 4.7重量份的 丙酮
乳化剂: 0.3重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了试验保护活性,将幼苗用活性化合物的制剂喷雾,直到湿润。在喷雾层干燥后,对植物用葡萄霜霉病的孢子水悬液接种,然后保持在20至22℃和相对湿度100%的小室中1天。然后,将植物放置在21℃和相对湿度90%的温室中5天。然后植物保持湿润,并放置在潮湿的小室中1天。
接种6天后,进行评价。
在此试验中,例如用制备实施例7、16、36、37和60的化合物,在10ppm的活性化合物的试验浓度下,有效率至少为90%。
实施例G
白粉病试验(苹果)/保护作用
溶剂: 4.7重量份的 丙酮
乳化剂: 0.3重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了试验保护活性,将幼苗用活性化合物的制剂喷雾,直到湿润。在喷雾层干燥后,对植物用苹果白粉病(Podosphaera leucotricha)致病微生物的孢子的粉末接种。
然后,将植物放置在23℃和相对湿度大约70%的温室中。
接种10天后,进行评价。
在此试验中,例如用制备实施例44、10、37和60的化合物,在25ppm的活性化合物的试验浓度下,有效率至少为96%。
实施例H
黑星病试验(苹果)/保护作用
溶剂: 4.7重量份的 丙酮
乳化剂: 0.3重量份的 烷基芳基聚乙二醇醚
为了生产活性化合物的适合的制剂,将1重量份的活性化合物与预定量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
为了试验保护活性,将幼苗用活性化合物的制剂喷雾,直到湿润。在喷雾层干燥后,对植物用苹果黑星病(Venturia inaequalis)致病微生物的孢子的孢子悬浮液接种,然后,将植物保持在20℃和相对湿度100%的接种室中1天。
然后,将植物放置在20℃和相对湿度大约70%的温室中。
接种12天后,进行评价。
在此试验中,例如用制备实施例37和60的化合物,在10ppm的活性化合物的试验浓度下,有效率至少为99%。
实施例I
绿蝇(Lucilia cuprina)抗性幼虫试验
乳化剂:35重量份的乙二醇单甲基醚
35重量份的壬基酚聚乙二醇醚
为了生产活性化合物的适合的制剂,将三重量份的活性化合物与七重量份的上述溶剂混合物混合,并将根据上述获得的浓缩物,各自用水稀释至所需浓度。
将大约20只绿蝇的抗性幼虫放入含有大约1cm3马肉和0.5ml活性化合物的制剂的试管中。24小时后确定损伤率。
100%意为所有的幼虫被杀死;0%意为没有幼虫被杀死。
在此试验中,例如用制备实施例60的化合物,在1000ppm的活性化合物的试验浓度下,损伤率为100%。
实施例J
家蝇试验
试验动物:家蝇(Musca domestica),WHO品系(N)
溶剂: 35重量份的 乙二醇单甲醚
乳化剂: 35重量份的 壬基酚聚乙二醇醚
为了生产活性化合物的适合的制剂,将三重量份的活性化合物用七份上述溶剂/乳化剂混合物稀释,并用水稀释由此获得的乳油至所需的具体浓度。
将2ml的上述活性化合物的制备物,用吸管吸至适当大小的培替氏培养皿的滤纸片上(直径9.5cm)。滤纸干燥后,将25只供试动物放入培替氏培养皿中,并盖住盖。
24小时后,确定活性化合物制剂的有效率。有效率用百分比表示。100%意为所有家蝇被杀死;0%意为没有家蝇被杀死。
在此试验中,例如用制备实施例60的化合物,用1000ppm的活性化合物的试验浓度,有效率为100%。
实施例K
蟑螂试验
试验动物:美洲大蠊(Periplaneta americana)
溶剂: 35重量份的 乙二醇单甲醚
乳化剂: 35重量份的 壬基酚聚乙二醇醚
为了生产活性化合物的适合的制剂,将三重量份的活性化合物用七份上述溶剂/乳化剂混合物稀释,并用水稀释由此获得的乳油至所需的具体浓度。
将2ml的上述活性化合物的制备物,用吸管吸至适当大小的培替氏培养皿的滤纸片上(直径9.5cm)。滤纸干燥后,将5只德国小蠊(B.germanica)或美洲大蠊(P.americana)放入培替氏培养皿中,并盖住盖。
3天后,确定活性化合物制剂的有效率。有效率用百分比表示。100%意为所有的蟑螂被杀死;0%意为没有蟑螂被杀死。
在此试验中,例如周制备实施例60的化合物,用1000ppm的活性化合物的试验浓度,有效率为100%。
Claims (9)
其中
X代表C-NO2、C-卤素、C-卤代烷基或N,
Y代表NO2、CN、卤素或卤代烷基,
Z代表NO2、卤素、卤代烷基、卤代烷氧基或卤代烷硫基,
R1代表氢、或各自可被选择取代的烷基、链烯基、链炔基、芳基、杂芳基或芳烷基,
R2和R3各自独立地代表
氢、卤素、氰基或硝基、或各自可被选择取代的烷基、芳基或杂芳基、或下述基团之一:CO2R5、CONR6R7、CSNR6R7、S(O)nR8,
R4代表氢、各自可被选择取代的烷基、链烯基、链炔基、芳烷基、芳氧基或芳烷氧基或下述基团之一:SO2NR6R7、SO2R9、COR10或CH2N(R9)w,其中
w代表CO2R5或SO2R5,
R5代表烷基,
R6和R7各自独立的代表氢或烷基、或与和它们相连的N原子一起形成一个环,该环可选择的至少还含有一个杂原子,
R8代表烷基或卤代烷基,
R9代表烷基或可选择取代的芳基,
R10代表烷基、烷氧基、或各自可被选择取代的芳基或芳氧基,和
n代表0、1或2,
条件是
如果
R4代表氢和同时
X代表C-NO2和同时
Y或Z之一代表卤代烷基而另外一个取代基代表NO2,则
R1不代表烷基、可选择取代的苯基、可选择取代的苯基磺酰基或吡啶基和/或
R2不代表氢、烷基或苯基和/或
R3不代表氢、CN、卤素、可选择取代的苯基、可选择取代的苯基磺酰基、CO2-烷基或CO2-苄基。
2.根据权利要求1的式(I)化合物,其中
X代表C-NO2、C-卤素、C-C1-C6-卤代烷基或N,
Y代表NO2、CN、卤素或C1-C6-卤代烷基,
Z代表NO2、卤素、C1-C6-卤代烷基、C1-C6-卤代烷氧基或C1-C6-卤代烷硫基,
R1代表氢、C1-C8-烷基、C1-C8-氰基烷基、C1-C8-卤代烷基、C1-C8-羟烷基、C1-C4-烷氧基-C1-C8-烷基、或代表苯基、苄基或苯乙基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基、苯基、苯氧基、CN或NO2,
或代表吡啶基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-烷氧基或C1-C4-卤代烷基,或代表嘧啶基、噻二唑基或噻唑基,其各自可被下述相同或不同的取代基可选择的单取代或二取代:卤素、C1-C4-烷基、C1-C4-烷氧基或C1-C4-卤代烷基,
R2和R3各自独立地代表
氢、卤素、氰基、硝基、C1-C8-烷基、C1-C8-卤代烷基、C1-C8-羟烷基、C1-C4-烷氧基-C1-C8-烷基、
或代表苯基或噻吩基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基或C1-C4-卤代烷硫基,或下述基团之一:CO2R5、CONR6R7、CSNR6R7、S(O)nR8,
R4代表氢、C1-C8-烷基、C1-C8-卤代烷基、C1-C8-羟烷基、C1-C4-烷氧基-C1-C8-烷基、C3-C8-链烯基、C3-C8-卤代链烯基、C3-C8-羟链烯基、C1-C4-烷氧基-C3-C8-链烯基、C3-C8-链炔基、C3-C8-卤代链炔基、C3-C8-羟链炔基、C1-C4-烷氧基-C3-C8-链炔基、
或代表苯氧基、苄基或苄氧基、其各自可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基或C1-C4-卤代烷氧基,或代表下述基团之一:SO2R9、COR10、CH2N(R9)w、SO2NR6R7,
w代表CO2R5或SO2R5,
R5代表C1-C8-烷基,
R6和R7各自独立的代表氢或C1-C8-烷基、或与和它们相连的N原子一起形成一个5-至7-元环,该环可选择的至少还含有另外两个杂原子,杂原子由N、O和S组成,
R8代表C1-C8-烷基或C1-C8-卤代烷基,
R9代表C1-C8-烷基或代表苯基,其可被下述相同或不同的取代基可选择的单取代至三取代:卤素、C1-C4-烷基或C1-C4-烷氧基,
R10代表C1-C8-烷基或C1-C8-烷氧基、或代表苯基或苯氧基,其各自可被卤素、C1-C4-烷基或C1-C4-烷氧基可选择的单取代至三取代,
n代表0、1或2,和
条件是
如果
R4代表氢且同时
X代表C-NO2和同时
Y或Z之一代表卤代烷基而另一个取代基代表NO2,则
R1不代表烷基、可选择取代的苯基、可选择取代的苯基磺酰基或吡啶基和/或
R2不代表氢、烷基或苯基和/或
R3不代表氢、CN、卤素、可选择取代的苯基、可选择取代的苯基磺酰基、CO2-烷基或CO2-苄基。
3.根据权利要求1的式(I)化合物,其中
X代表C-NO2、C-氟、C-氯、C-溴、或具有1至5个相同或不同的卤原子的C-C1-C3-卤代烷基,卤原子由氟、氯和溴组成,或代表N,
Y代表NO2、CN、氟、氯、溴或具有1至7个相同或不同的卤原子的C1-C4-卤代烷基,卤原子由氟、氯和溴组成,
Z代表NO2、氟、氯、溴、各自具有1至7个相同或不同的卤原子的C1-C4-卤代烷基、C1-C4-卤代烷氧基或C1-C4-卤代烷硫基,卤原子由氟、氯和溴组成,
R1代表各自具有一至三个相同或不同的卤原子的C1-C6-烷基、C1-C6-氰基烷基、C1-C6-卤代烷基、卤原子由氟、氯和溴组成,或代表C1-C6-羟烷基、C1-C2-烷氧基-C1-C6-烷基、
或代表苯基、苄基或苯乙基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、C1-C3-烷基、C1-C3-烷氧基、各自具有一至三个相同或不同的卤原子的C1-C3-卤代烷基、C1-C3-卤代烷氧基或C1-C4-卤代烷硫基,其中的卤原子由氟、氯和溴组成、或CN或硝基,或代表吡啶基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、C1-C3-烷基、C1-C3-烷氧基或具有一至三个相同或不同的卤原子的C1-C3-卤代烷基,其中的卤原子由氟、氯和溴组成,
或代表嘧啶基或噻二唑基,其各自可被下述相同或不同的取代基可选择的单取代或二取代:氟、氯、溴,C1-C3-烷基、C1-C3-烷氧基和具有一至三个相同或不同的卤原子的C1-C3-卤代烷基,其中的卤原子由氟、氯和溴组成,
R2和R3各自独立地代表
氢、氟、氯、溴、氰基、C1-C6-烷基、具有一至六个相同或不同的卤原子的C1-C6-卤代烷基、其中卤原子由氟、氯和溴组成,或代表C1-C2-烷氧基-C1-C6-烷基、或代表苯基或噻吩基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、C1-C3-烷基或C1-C3-烷氧基,或代表下述基团之一:CO2R5、CONR6R7、CSNR6R7、S(O)nR8,
R4代表氢、或代表C1-C6-烷基、C3-C6-链烯基或C3-C6-链炔基,其各自可被一至三个由氟、氯和溴组成的卤原子可选择的取代,或代表C1-C4-烷氧基甲基、
或代表苄基或苄氧基、其各自可被氟、氯或溴可选择地单取代至二取代,或代表下述基团之一:SO2R9、COR10、CH2N(R9)CO2R5,
R5代表C1-C4-烷基,
R6和R7各自独立地代表氢、甲基或乙基,
R8代表C1-C4-烷基或具有一至三个氟和/或氯原子的C1-C4-卤代烷基,
R9代表C1-C4-烷基,或代表苯基,其可被氟、氯和/或溴可选择地单取代至三取代,
R10代表C1-C4-烷基、或代表苯基,其可被氟、氯和/或溴可选择的单取代至三取代,和
n代表0、1或2,
条件是
如果
R4代表氢且同时
X代表C-NO2和同时
Y或Z之一代表卤代烷基而另一取代基代表NO2,则
R1不代表烷基、可选择取代的苯基、可选择取代的苯基磺酰基或吡啶基和/或
R2不代表氢、烷基或苯基和/或
R3不代表氢、CN、卤素、可选择取代的苯基、可选择取代的苯基磺酰基、CO2-烷基或CO2-苄基。
4.根据权利要求1的式(I)化合物,其中
X代表C-NO2、C-Cl或N,
Y代表NO2、CN、氟、氯或CF3,
Z代表NO2、氟、氯、CF3、OCF3或SCF3,
R1代表甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基的各种异构体或己基的各种异构体,它们各自可选择的被氟和/或氯单取代至三取代或被氰基单取代、或代表苯基、苄基或苯乙基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、CF3、OCF3、SCF3、CN和NO2、或代表吡啶基、嘧啶基或噻二唑基,其各自可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴或CF3,
R2和R3各自独立地代表
氢、氯、溴、CN、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、CF3、C2F5或CH2OCH3、
或代表苯基,其可被下述相同或不同的取代基可选择的单取代至三取代:氟、氯、溴、甲基或甲氧基,或代表下述基团之一:CO2R5、CONR6R7或S(O)nR8,
R4代表氢、甲基、乙基、2-丙烯基、2-丙炔基、甲氧基甲基、乙氧基甲基、丙氧基甲基、异丙氧基甲基或正丁氧基甲基,
R5代表甲基或乙基,
R6和R7代表氢,
R8代表甲基、乙基、三氟甲基、1,1-二氟乙基或2,2,2-三氟乙基,和
n代表0、1或2,
条件是
如果
R4代表氢且同时
X代表C-NO2和同时
Y或Z之一代表卤代烷基而另一个取代基代表NO2,则
R1不代表烷基、可选择取代的苯基、可选择取代的苯基磺酰基或比啶基和/或
R2不代表氢、烷基或苯基和/或
R3不代表氢、CN、卤素、可选择取代的苯基、可选择取代的苯基磺酰基、CO2-烷基或CO2-苄基。
5.根据权利要求的式(I)化合物的制备方法,其特征在于A)为了制备式(I)的N-吡唑基苯胺和N-吡唑基氨基吡啶,
其中
R1、R2和R3为权利要求1中给出的定义
其中
Hal代表氟、氯、溴或碘,和
X、Y和Z为权利要求1中给出的定义
其中
X、Y、Z、R1、R2和R3为上述定义
R11-V (IV)
其中
V代表阴离子离去基团,例如氯、溴、碘、乙酰氧基、甲苯磺酰基或甲基磺酰基,和
R11为上述在权利要求1中给出的,除去氢的R4的定义,和
B)为制备式(Ib)化合物,
其中
R1、R2、R3、X、Y和Z为上述定义,和
R11为上述定义
在碱存在下和在稀释剂存在下,使式(II)的5-氨基吡唑与式(IV)的化合物反应,
其中
R1、R2和R3为上述定义
R11-V (IV)
其中
R11和V为上述的定义
接着,在碱存在下和在稀释剂存在下,使所得的式(V)化合物与式(III)的化合物反应,
其中
其中Hal、X、Y和Z为上述定义。
6.至少包含一种根据权利要求1的式(I)化合物的杀虫剂。
7.应用根据权利要求1的式(I)化合物消灭有害动物的用途。
8.消灭有害动物的方法,其特征在于使根据权利要求1的式(I)化合物作用于有害动物和/或其环境。
9.防治有害动物的组合物的制备方法,其特征在于将根据权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4405207A DE4405207A1 (de) | 1994-02-18 | 1994-02-18 | N-Pyrazolylaniline und N-Pyrazolylaminopyridine |
DEP4405207.3 | 1994-02-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1140449A true CN1140449A (zh) | 1997-01-15 |
Family
ID=6510572
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN95191611.4A Pending CN1140449A (zh) | 1994-02-18 | 1995-02-06 | 用作害虫防治剂的n-吡唑基苯胺和n-吡唑基氨基吡啶 |
Country Status (9)
Country | Link |
---|---|
US (1) | US5849778A (zh) |
EP (1) | EP0745067A1 (zh) |
JP (1) | JPH09509163A (zh) |
CN (1) | CN1140449A (zh) |
AU (1) | AU1807595A (zh) |
BR (1) | BR9506832A (zh) |
DE (1) | DE4405207A1 (zh) |
MX (1) | MX9603465A (zh) |
WO (1) | WO1995022530A1 (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102421756A (zh) * | 2009-03-03 | 2012-04-18 | 纳幕尔杜邦公司 | 杀真菌的吡唑化合物 |
CN103140136A (zh) * | 2010-09-01 | 2013-06-05 | 杜邦公司 | 杀真菌吡唑以及它们的混合物 |
CN108003103A (zh) * | 2017-12-15 | 2018-05-08 | 浙江工业大学 | 一种磺酰化的5-氨基吡唑类化合物的合成方法 |
CN109535142A (zh) * | 2018-12-26 | 2019-03-29 | 西华大学 | 2-(1-吡唑基)嘧啶衍生物及其制备方法和应用 |
CN116023335A (zh) * | 2022-12-28 | 2023-04-28 | 河北科技大学 | 一种苯甲酰脲衍生物及其制备方法和应用 |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19532066A1 (de) * | 1995-08-31 | 1997-03-06 | Bayer Ag | Substituierte 5-Aminopyrazole |
FR2745466B1 (fr) * | 1996-03-04 | 1998-04-10 | Rhone Poulenc Agrochimie | Pyrazoles fongicides |
FR2745469B1 (fr) * | 1996-03-04 | 1998-09-18 | Rhone Poulenc Agrochimie | Pyrazoles fongicides |
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 |
US6409988B1 (en) | 1999-07-01 | 2002-06-25 | 3-Dimensional Pharmaceuticals, Inc. | Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands |
US6506784B1 (en) | 1999-07-01 | 2003-01-14 | 3-Dimensional Pharmaceuticals, Inc. | Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides |
US6518266B1 (en) | 1999-07-22 | 2003-02-11 | 3-Dimensional Pharmaceuticals | 1- Aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides |
US6545033B1 (en) | 1999-10-06 | 2003-04-08 | 3-Dimensional Pharmaceuticals, Inc. | Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides |
AR049418A1 (es) * | 2004-02-27 | 2006-08-02 | Bayer Pharmaceuticals Corp | Derivados de heteroarilaminopirazol y composiciones farmaceuticas para el tratamiento de la diabetes. |
EP1871743A4 (en) * | 2005-04-11 | 2009-12-30 | Univ Murdoch | ANTIPARASITIC COMPOUNDS |
DE102007003036A1 (de) * | 2006-12-20 | 2008-06-26 | Bayer Cropscience Ag | Pyrimidinylpyrazole |
WO2009156090A2 (de) * | 2008-06-26 | 2009-12-30 | Bayer Cropscience Aktiengesellschaft | Insektizide schwefel-derivatisierte 1-azinylpyrazole |
BR112012011064A2 (pt) | 2009-11-11 | 2015-10-06 | Bayer Cropscience Ag | novos compostos de diazinilpirazolila. |
BR102012004142A2 (pt) * | 2011-02-25 | 2015-04-07 | Dow Agrosciences Llc | Composições pesticidas e processos relacionados às mesmas |
TWI568721B (zh) * | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
NZ628080A (en) | 2012-03-16 | 2016-09-30 | Axikin Pharmaceuticals Inc | 3,5-diaminopyrazole kinase inhibitors |
NZ631142A (en) | 2013-09-18 | 2016-03-31 | Axikin Pharmaceuticals Inc | Pharmaceutically acceptable salts of 3,5-diaminopyrazole kinase inhibitors |
WO2016092559A1 (en) * | 2014-12-12 | 2016-06-16 | Oat & Iil India Laboratories Private Limited | Substituted pyrazole derivatives having activity as fungicides |
TWI703133B (zh) | 2014-12-23 | 2020-09-01 | 美商艾克斯基製藥公司 | 3,5-二胺基吡唑激酶抑制劑 |
US10351532B2 (en) | 2014-12-29 | 2019-07-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Small molecule inhibitors of lactate dehydrogenase and methods of use thereof |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR9305466A (pt) * | 1992-03-26 | 1994-12-20 | Dowelanco | Nitroanilinas n-heterocíclicas usadas como fungicidas |
-
1994
- 1994-02-18 DE DE4405207A patent/DE4405207A1/de not_active Withdrawn
-
1995
- 1995-02-06 AU AU18075/95A patent/AU1807595A/en not_active Abandoned
- 1995-02-06 MX MX9603465A patent/MX9603465A/es unknown
- 1995-02-06 WO PCT/EP1995/000416 patent/WO1995022530A1/de not_active Application Discontinuation
- 1995-02-06 JP JP7521545A patent/JPH09509163A/ja active Pending
- 1995-02-06 BR BR9506832A patent/BR9506832A/pt not_active Application Discontinuation
- 1995-02-06 CN CN95191611.4A patent/CN1140449A/zh active Pending
- 1995-02-06 US US08/693,063 patent/US5849778A/en not_active Expired - Fee Related
- 1995-02-06 EP EP95909674A patent/EP0745067A1/de not_active Withdrawn
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI548344B (zh) * | 2009-03-03 | 2016-09-11 | 杜邦股份有限公司 | 殺真菌之吡唑 |
CN107011326B (zh) * | 2009-03-03 | 2019-11-12 | Fmc公司 | 杀真菌的吡唑化合物 |
CN107011326A (zh) * | 2009-03-03 | 2017-08-04 | 纳幕尔杜邦公司 | 杀真菌的吡唑化合物 |
CN102421756A (zh) * | 2009-03-03 | 2012-04-18 | 纳幕尔杜邦公司 | 杀真菌的吡唑化合物 |
CN106417305A (zh) * | 2010-09-01 | 2017-02-22 | 杜邦公司 | 杀真菌吡唑以及它们的混合物 |
CN103140136B9 (zh) * | 2010-09-01 | 2016-06-29 | 杜邦公司 | 杀真菌吡唑以及它们的混合物 |
CN103140136B (zh) * | 2010-09-01 | 2016-05-11 | 杜邦公司 | 杀真菌吡唑以及它们的混合物 |
TWI504350B (zh) * | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
CN103140136A (zh) * | 2010-09-01 | 2013-06-05 | 杜邦公司 | 杀真菌吡唑以及它们的混合物 |
CN108003103A (zh) * | 2017-12-15 | 2018-05-08 | 浙江工业大学 | 一种磺酰化的5-氨基吡唑类化合物的合成方法 |
CN108003103B (zh) * | 2017-12-15 | 2020-10-27 | 浙江工业大学 | 一种磺酰化的5-氨基吡唑类化合物的合成方法 |
CN109535142A (zh) * | 2018-12-26 | 2019-03-29 | 西华大学 | 2-(1-吡唑基)嘧啶衍生物及其制备方法和应用 |
CN109535142B (zh) * | 2018-12-26 | 2022-01-14 | 西华大学 | 2-(1-吡唑基)嘧啶衍生物及其制备方法和应用 |
CN116023335A (zh) * | 2022-12-28 | 2023-04-28 | 河北科技大学 | 一种苯甲酰脲衍生物及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
DE4405207A1 (de) | 1995-08-24 |
EP0745067A1 (de) | 1996-12-04 |
BR9506832A (pt) | 1997-10-14 |
US5849778A (en) | 1998-12-15 |
MX9603465A (es) | 1997-03-29 |
AU1807595A (en) | 1995-09-04 |
WO1995022530A1 (de) | 1995-08-24 |
JPH09509163A (ja) | 1997-09-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1140449A (zh) | 用作害虫防治剂的n-吡唑基苯胺和n-吡唑基氨基吡啶 | |
CN1075060C (zh) | 用作除草剂和农药的烷氧基-烷基取代的1-h-3-芳基-吡咯烷-2,4-二酮 | |
CN1031238C (zh) | 3-氰基-5-烷氧基-1-芳基吡唑杀虫剂 | |
CN1105709C (zh) | 作为杀虫剂的3-硫代氨甲酰吡唑衍生物 | |
CN1115344C (zh) | 取代苯基酮-烯醇衍生物,制备方法和用途 | |
CN1059672C (zh) | 1,2,4-二唑衍生物 | |
CN1039079C (zh) | 含有1-芳基吡咯的杀虫药组合物及其用途 | |
CN1071163A (zh) | 杂环化合物 | |
CN1141032A (zh) | 杀虫剂 | |
CN1119436A (zh) | 稠合含氮杂环化合物及其它们作为杀虫剂和杀菌剂等的应用 | |
CN1050878A (zh) | 新型硅烷衍生物,含该衍生物的制剂及其作为农药的应用 | |
CN1260793A (zh) | 4-卤烷基-3-杂环基吡啶类及4-卤烷基-5-杂环基嘧啶类化合物,其制法,含其的组合物及其用作杀虫剂的用途 | |
CN1045775C (zh) | 取代的硝基嘧啶及其制备和在杀虫剂中的应用 | |
CN1210518A (zh) | 芳基吡唑杀虫剂 | |
CN87103967A (zh) | 1,2,3,6-四氢-5-硝基—嘧啶衍生物 | |
CN1112849C (zh) | 1,2,3-噻二唑羧酸(硫代)酯防治害物的用途 | |
CN1384826A (zh) | 作为农药的N-杂芳基-α-烷氧亚氨基羧酸酰胺 | |
CN1096446C (zh) | N-(邻位取代苄氧基)亚胺衍生物及其用作杀真菌剂、杀螨剂或杀虫剂的用途 | |
CN1028228C (zh) | 制备1-芳基吡唑的方法 | |
CN1207725A (zh) | 农药 | |
CN1113238A (zh) | 取代的吡唑啉衍生物 | |
CN1033622A (zh) | 杂环杀虫剂 | |
CN1086215A (zh) | 取代的氨基甲酰基吡唑啉 | |
CN1083804A (zh) | 羧酸衍生物 | |
CN1086513A (zh) | 取代的2-芳基吡咯 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C01 | Deemed withdrawal of patent application (patent law 1993) | ||
WD01 | Invention patent application deemed withdrawn after publication |