DD257381A5 - Schaedlingsbekaempfungsmittel, insektizide und nematizide mittel - Google Patents

Schaedlingsbekaempfungsmittel, insektizide und nematizide mittel Download PDF

Info

Publication number: DD257381A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; optionally; phenyl; haloalkyl; carbon atoms
Prior art date: 1986-01-08

Application number

DD87299131A

Other languages

German (de)

English (en)

Inventor

Uta Jensen-Korte

Otto Schallner

Joerg Stetter

Heinz-Juergen Wroblowsky

Wilhelm Stendel

Benedikt Becker

Bernhard Homeyer

Wolfgang Behrenz

Original Assignee

��@��k��

Priority date (The priority date 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 date listed.)

1986-01-08

Filing date

1987-01-07

Publication date

1988-06-15

1987-01-07 Application filed by ��@��k�� filed Critical ��@��k��

1988-06-15 Publication of DD257381A5 publication Critical patent/DD257381A5/de

Links

239000002917 insecticide Substances 0.000 title claims description 7
239000005645 nematicide Substances 0.000 title claims description 6
-1 2,4-dinitrophenyl radical Chemical class 0.000 claims abstract description 102
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 26
125000004961 1-arylpyrazolyl group Chemical group 0.000 claims abstract description 24
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 6
125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims description 140
238000000034 method Methods 0.000 claims description 40
238000002360 preparation method Methods 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 22
239000004480 active ingredient Substances 0.000 claims description 21
241000238631 Hexapoda Species 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
230000000749 insecticidal effect Effects 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 7
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 6
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 6
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000000575 pesticide Substances 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
241000244206 Nematoda Species 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000005998 bromoethyl group Chemical group 0.000 claims description 2
125000005997 bromomethyl group Chemical group 0.000 claims description 2
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 2
125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])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
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
BFZWJHVEJPNAJI-UHFFFAOYSA-N NC(N(C)NCC)NC Chemical class NC(N(C)NCC)NC BFZWJHVEJPNAJI-UHFFFAOYSA-N 0.000 claims 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
125000006343 heptafluoro propyl group Chemical group 0.000 claims 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 1
125000006193 alkinyl group Chemical group 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical compound [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 55
238000012360 testing method Methods 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
239000002904 solvent Substances 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000003085 diluting agent Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
241001465754 Metazoa Species 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000009472 formulation Methods 0.000 description 14
239000002689 soil Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000003995 emulsifying agent Substances 0.000 description 12
239000007858 starting material Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
239000002253 acid Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
241000238876 Acari Species 0.000 description 7
241000607479 Yersinia pestis Species 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
229920000151 polyglycol Polymers 0.000 description 6
239000010695 polyglycol Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
240000007124 Brassica oleracea Species 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 4
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
239000000969 carrier Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
230000003071 parasitic effect Effects 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
238000003860 storage Methods 0.000 description 4
WAXMYJHKYNNDEI-UHFFFAOYSA-N (5-amino-1h-pyrazol-4-yl) thiocyanate Chemical class NC=1NN=CC=1SC#N WAXMYJHKYNNDEI-UHFFFAOYSA-N 0.000 description 3
QJMTWUBARZORQK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-(trifluoromethylsulfanyl)pyrazole Chemical compound CC1=C(SC(F)(F)F)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QJMTWUBARZORQK-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
FWAQKPHSHQQFQI-UHFFFAOYSA-N 4-(dimethylamino)-3-(trifluoromethylsulfanyl)but-3-en-2-one Chemical compound CN(C)C=C(C(C)=O)SC(F)(F)F FWAQKPHSHQQFQI-UHFFFAOYSA-N 0.000 description 3
241000238657 Blattella germanica Species 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241000257166 Lucilia cuprina Species 0.000 description 3
241000257159 Musca domestica Species 0.000 description 3
241001608567 Phaedon cochleariae Species 0.000 description 3
241000500437 Plutella xylostella Species 0.000 description 3
241000238680 Rhipicephalus microplus Species 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
IYGWTAQAGBMWRC-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-(trifluoromethylsulfanyl)pyrazol-3-amine Chemical compound NC1=C(SC(F)(F)F)C(C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl IYGWTAQAGBMWRC-UHFFFAOYSA-N 0.000 description 2
PGNKEYDZRUGQMQ-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PGNKEYDZRUGQMQ-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
241001143309 Acanthoscelides obtectus Species 0.000 description 2
240000003291 Armoracia rusticana Species 0.000 description 2
235000011330 Armoracia rusticana Nutrition 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241000084475 Delia antiqua Species 0.000 description 2
241001529600 Diabrotica balteata Species 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241000255925 Diptera Species 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000258937 Hemiptera Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
241000257303 Hymenoptera Species 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 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
241000258242 Siphonaptera Species 0.000 description 2
241000254179 Sitophilus granarius Species 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000256248 Spodoptera Species 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
FYOWOHMZNWQLFG-UHFFFAOYSA-N [2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(Cl)C=C(C(F)(F)F)C=C1Cl FYOWOHMZNWQLFG-UHFFFAOYSA-N 0.000 description 2
DGGZPEGQLMBEDD-UHFFFAOYSA-N [2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical compound Cl.NNC1=C(Cl)C=C(C(F)(F)F)C=C1Cl DGGZPEGQLMBEDD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000008360 acrylonitriles Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000011161 development Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
244000078703 ectoparasite Species 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
210000004209 hair Anatomy 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000004440 haloalkylsulfinyl group Chemical group 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000011707 mineral Substances 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003217 pyrazoles Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000005507 spraying Methods 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
239000008096 xylene Substances 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
CHMDPOPGPPRKCR-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-methyl-5-phenyl-4-(trifluoromethylsulfanyl)pyrazole Chemical compound FC(F)(F)SC=1C(C)=NN(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)C=1C1=CC=CC=C1 CHMDPOPGPPRKCR-UHFFFAOYSA-N 0.000 description 1
VBKYDHUPKVGGTF-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-(trifluoromethylsulfonyl)pyrazole Chemical compound CC1=C(S(=O)(=O)C(F)(F)F)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VBKYDHUPKVGGTF-UHFFFAOYSA-N 0.000 description 1
WBFCRVVMKUBKMJ-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl WBFCRVVMKUBKMJ-UHFFFAOYSA-N 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 description 1
ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 1
MPXLVMGLMXJXPS-UHFFFAOYSA-N 5-(1h-pyrazol-5-yldisulfanyl)-1h-pyrazole Chemical class C1=CNN=C1SSC=1C=CNN=1 MPXLVMGLMXJXPS-UHFFFAOYSA-N 0.000 description 1
IXBIXLUXCOIZIG-UHFFFAOYSA-N 5-(methylsulfanylmethyl)-1h-pyrazole Chemical compound CSCC=1C=CNN=1 IXBIXLUXCOIZIG-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241000238818 Acheta domesticus Species 0.000 description 1
241000902874 Agelastica alni Species 0.000 description 1
241001136265 Agriotes Species 0.000 description 1
241000218473 Agrotis Species 0.000 description 1
RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241001398046 Amphimallon solstitiale Species 0.000 description 1
241000411449 Anobium punctatum Species 0.000 description 1
241000256186 Anopheles <genus> Species 0.000 description 1
241001427556 Anoplura Species 0.000 description 1
241000254177 Anthonomus Species 0.000 description 1
241001640910 Anthrenus Species 0.000 description 1
241001414828 Aonidiella aurantii Species 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
241001600408 Aphis gossypii Species 0.000 description 1
241001095118 Aphis pomi Species 0.000 description 1
241000239223 Arachnida Species 0.000 description 1
241001162025 Archips podana Species 0.000 description 1
241000722823 Armadillidium Species 0.000 description 1
241000387321 Aspidiotus nerii Species 0.000 description 1
241001174347 Atomaria Species 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
241000131286 Attagenus Species 0.000 description 1
241000221377 Auricularia Species 0.000 description 1
241001490249 Bactrocera oleae Species 0.000 description 1
241000254127 Bemisia tabaci Species 0.000 description 1
241001142392 Bibio Species 0.000 description 1
241001573716 Blaniulus guttulatus Species 0.000 description 1
241000238662 Blatta orientalis Species 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
241000913391 Brachionus forficula Species 0.000 description 1
235000011331 Brassica Nutrition 0.000 description 1
241000219198 Brassica Species 0.000 description 1
235000011303 Brassica alboglabra Nutrition 0.000 description 1
235000011302 Brassica oleracea Nutrition 0.000 description 1
241001444260 Brassicogethes aeneus Species 0.000 description 1
241000982105 Brevicoryne brassicae Species 0.000 description 1
241001517925 Bucculatrix Species 0.000 description 1
241001491790 Bupalus piniaria Species 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
DASQIKOOFDJYKA-UHFFFAOYSA-N CCIF Chemical compound CCIF DASQIKOOFDJYKA-UHFFFAOYSA-N 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
241000257163 Calliphora vicina Species 0.000 description 1
241001350371 Capua Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000255579 Ceratitis capitata Species 0.000 description 1
241001098608 Ceratophyllus Species 0.000 description 1
241000426499 Chilo Species 0.000 description 1
241000258920 Chilopoda Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000255942 Choristoneura fumiferana Species 0.000 description 1
241001124134 Chrysomelidae Species 0.000 description 1
241001327638 Cimex lectularius Species 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
241001427559 Collembola Species 0.000 description 1
241000683561 Conoderus Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241001212534 Cosmopolites sordidus Species 0.000 description 1
241000500864 Costelytra Species 0.000 description 1
241001094916 Cryptomyzus ribis Species 0.000 description 1
241000256054 Culex <genus> Species 0.000 description 1
241000692095 Cuterebra Species 0.000 description 1
241001635274 Cydia pomonella Species 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
241001124144 Dermaptera Species 0.000 description 1
241001641895 Dermestes Species 0.000 description 1
241000489975 Diabrotica Species 0.000 description 1
241000258963 Diplopoda Species 0.000 description 1
241000511318 Diprion Species 0.000 description 1
241000255601 Drosophila melanogaster Species 0.000 description 1
241001425477 Dysdercus Species 0.000 description 1
241000353522 Earias insulana Species 0.000 description 1
241000995023 Empoasca Species 0.000 description 1
241000122098 Ephestia kuehniella Species 0.000 description 1
241000462639 Epilachna varivestis Species 0.000 description 1
241000917107 Eriosoma lanigerum Species 0.000 description 1
241000060469 Eupoecilia ambiguella Species 0.000 description 1
241000483001 Euproctis chrysorrhoea Species 0.000 description 1
241000515838 Eurygaster Species 0.000 description 1
241000239245 Euscelis Species 0.000 description 1
241001585293 Euxoa Species 0.000 description 1
241000371383 Fannia Species 0.000 description 1
241000233488 Feltia Species 0.000 description 1
241000255896 Galleria mellonella Species 0.000 description 1
241001660203 Gasterophilus Species 0.000 description 1
241000723283 Geophilus carpophagus Species 0.000 description 1
241001043186 Gibbium Species 0.000 description 1
241001243091 Gryllotalpa Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000790933 Haematopinus Species 0.000 description 1
241000256257 Heliothis Species 0.000 description 1
241001659688 Hercinothrips femoralis Species 0.000 description 1
241001466007 Heteroptera Species 0.000 description 1
241000957299 Homona magnanima Species 0.000 description 1
241001417351 Hoplocampa 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
241001495069 Ischnocera Species 0.000 description 1
241001149911 Isopoda Species 0.000 description 1
241000256602 Isoptera Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241001470017 Laodelphax striatella Species 0.000 description 1
241000256686 Lasius <genus> Species 0.000 description 1
241000238866 Latrodectus mactans Species 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
241000500881 Lepisma Species 0.000 description 1
241000258916 Leptinotarsa decemlineata Species 0.000 description 1
241001113970 Linognathus Species 0.000 description 1
241000254025 Locusta migratoria migratorioides Species 0.000 description 1
241000257162 Lucilia <blowfly> Species 0.000 description 1
241000721696 Lymantria Species 0.000 description 1
241000255685 Malacosoma neustria Species 0.000 description 1
241000555303 Mamestra brassicae Species 0.000 description 1
241001415013 Melanoplus Species 0.000 description 1
241000254099 Melolontha melolontha Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
241000952627 Monomorium pharaonis Species 0.000 description 1
241000257229 Musca <genus> Species 0.000 description 1
241000721623 Myzus Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-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
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
241001556089 Nilaparvata lugens Species 0.000 description 1
241001385056 Niptus hololeucus Species 0.000 description 1
241000384103 Oniscus asellus Species 0.000 description 1
241000963703 Onychiurus armatus Species 0.000 description 1
241001491877 Operophtera brumata Species 0.000 description 1
241000131102 Oryzaephilus Species 0.000 description 1
241000131101 Oryzaephilus surinamensis Species 0.000 description 1
241000975417 Oscinella frit Species 0.000 description 1
241001147398 Ostrinia nubilalis Species 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
241000486438 Panolis flammea Species 0.000 description 1
241000282376 Panthera tigris Species 0.000 description 1
241001450657 Parthenolecanium corni Species 0.000 description 1
241000721451 Pectinophora gossypiella Species 0.000 description 1
241000517306 Pediculus humanus corporis Species 0.000 description 1
241000721454 Pemphigus Species 0.000 description 1
241000238675 Periplaneta americana Species 0.000 description 1
241001608568 Phaedon Species 0.000 description 1
241001401861 Phorodon humuli Species 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
241001517955 Phyllonorycter blancardella Species 0.000 description 1
241000255972 Pieris <butterfly> Species 0.000 description 1
241000690748 Piesma Species 0.000 description 1
241000500439 Plutella Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
241000908127 Porcellio scaber Species 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
235000005805 Prunus cerasus Nutrition 0.000 description 1
241000722234 Pseudococcus 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
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
241001509970 Reticulitermes <genus> Species 0.000 description 1
241000722251 Rhodnius Species 0.000 description 1
241000125167 Rhopalosiphum padi Species 0.000 description 1
241001510236 Rhyparobia maderae Species 0.000 description 1
241000318997 Rhyzopertha dominica Species 0.000 description 1
241000316887 Saissetia oleae Species 0.000 description 1
241000253973 Schistocerca gregaria Species 0.000 description 1
241000522594 Scorpio maurus Species 0.000 description 1
241001157779 Scutigera Species 0.000 description 1
241001313237 Scutigerella immaculata Species 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
241000180219 Sitobion avenae Species 0.000 description 1
241000254181 Sitophilus Species 0.000 description 1
241000985245 Spodoptera litura Species 0.000 description 1
241001494139 Stomoxys Species 0.000 description 1
241000883295 Symphyla Species 0.000 description 1
241000255626 Tabanus <genus> Species 0.000 description 1
241000254109 Tenebrio molitor Species 0.000 description 1
241000339374 Thrips tabaci Species 0.000 description 1
241000130771 Tinea pellionella Species 0.000 description 1
241000333690 Tineola bisselliella Species 0.000 description 1
241000511627 Tipula paludosa Species 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
241001238451 Tortrix viridana Species 0.000 description 1
241000018135 Trialeurodes Species 0.000 description 1
241001414833 Triatoma Species 0.000 description 1
241000254086 Tribolium <beetle> Species 0.000 description 1
241001259047 Trichodectes Species 0.000 description 1
241000255993 Trichoplusia ni Species 0.000 description 1
241000267823 Trogoderma Species 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
241001274788 Viteus vitifoliae Species 0.000 description 1
235000013447 Xanthosoma atrovirens Nutrition 0.000 description 1
240000001781 Xanthosoma sagittifolium Species 0.000 description 1
241000353223 Xenopsylla cheopis Species 0.000 description 1
241001466337 Yponomeuta Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
241001414985 Zygentoma Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000011609 ammonium molybdate Substances 0.000 description 1
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
235000018660 ammonium molybdate Nutrition 0.000 description 1
229940010552 ammonium molybdate Drugs 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
244000000054 animal parasite Species 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000005667 attractant Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000004071 biological effect Effects 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
239000001273 butane Substances 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
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 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
150000001735 carboxylic acids Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
230000009189 diving Effects 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000012173 estrus Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000003197 gene knockdown Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 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
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
244000144972 livestock Species 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [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
239000004579 marble Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 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
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003595 mist Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011435 rock Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- 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
- C07D231/18—One oxygen or sulfur atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD87299131A 1986-01-08 1987-01-07 Schaedlingsbekaempfungsmittel, insektizide und nematizide mittel DD257381A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863600287 DE3600287A1 (de)	1986-01-08	1986-01-08	1-arylpyrazole

Publications (1)

Publication Number	Publication Date
DD257381A5 true DD257381A5 (de)	1988-06-15

Family

ID=6291494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87299131A DD257381A5 (de)	1986-01-08	1987-01-07	Schaedlingsbekaempfungsmittel, insektizide und nematizide mittel

Country Status (18)

Country	Link
US (1)	US4810720A (da)
EP (1)	EP0231510B1 (da)
JP (1)	JPH0819107B2 (da)
KR (1)	KR870007133A (da)
AT (1)	ATE56959T1 (da)
AU (1)	AU596389B2 (da)
BR (1)	BR8700046A (da)
DD (1)	DD257381A5 (da)
DE (2)	DE3600287A1 (da)
DK (1)	DK6287A (da)
ES (1)	ES2036172T3 (da)
GR (1)	GR3000881T3 (da)
HU (1)	HU198692B (da)
IL (1)	IL81161A0 (da)
NZ (1)	NZ218806A (da)
PL (1)	PL263578A1 (da)
TR (1)	TR23157A (da)
ZA (1)	ZA8777B (da)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5232940A (en) *	1985-12-20	1993-08-03	Hatton Leslie R	Derivatives of N-phenylpyrazoles
US6372774B1 (en)	1985-12-20	2002-04-16	Rhone-Poulenc Agriculture Ltd.	Derivatives of N-phenylpyrazoles
US5547974A (en) *	1985-12-20	1996-08-20	Rhone-Poulenc Agriculture Ltd.	Derivatives of N-phenylpyrazoles
DE3725660A1 (de) *	1987-08-03	1989-02-16	Bayer Ag	3,5-dialkyl-1-arylpyrazole
DE3726529A1 (de) *	1987-08-10	1989-02-23	Bayer Ag	1-arylpyrazole
IL112721A0 (en) *	1994-03-10	1995-05-26	Zeneca Ltd	Azole derivatives
US6060502A (en) *	1995-06-05	2000-05-09	Rhone-Poulenc Agrochimie	Pesticidal sulfur compounds
US6060495A (en) *	1995-06-05	2000-05-09	Rhone-Poulenc Agrochimie	Pesticidal sulfur compounds
US6136983A (en) *	1995-06-05	2000-10-24	Rhone-Poulenc Agrochimie	Pesticidal sulfur compounds
US5817688A (en) *	1995-12-19	1998-10-06	Rhone-Poulenc Inc.	Pesticidal 1-arylpyrazole derivatives
ES2191076T3 (es) *	1995-12-19	2003-09-01	Bayer Cropscience Sa	Nuevos derivados de 1-aril-pirazol y su empleo como plaguicidas.
US5922885A (en)	1995-12-19	1999-07-13	Rhone-Poulenc Inc.	Pesticidal 1-arylpyrazole derivatives
FR2752525B1 (fr) *	1996-08-20	2000-05-05	Rhone Merieux	Procede de lutte contre les myiases des cheptels bovins et ovins et compositions pour la mise en oeuvre de ce procede
ZA981776B (en)	1997-03-10	1998-09-03	Rhone Poulenc Agrochimie	Pesticidal 1-arylpyrazoles
ZA981934B (en) *	1997-03-10	1999-09-06	Rhone Poulenc Agrochimie	Pesticidal 1-aryl-3-iminopyrazoles.
US6541273B1 (en)	1999-11-12	2003-04-01	Aventis Cropscience, S.A.	Multiple sorbent cartridges for solid phase extraction
GB0016787D0 (en)	2000-07-07	2000-08-30	Pfizer Ltd	Compounds useful in therapy
AU2012203942B2 (en) *	2006-07-05	2014-11-27	Boehringer Ingelheim Animal Health USA Inc.	1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof
WO2008005489A2 (en)	2006-07-05	2008-01-10	Aventis Agriculture	1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof
US9173728B2 (en)	2008-11-19	2015-11-03	Merial Inc.	Multi-cavity container having offset indentures for dispensing fluids
US8450357B2 (en)	2008-11-19	2013-05-28	Merial Limited	Compositions comprising an aryl pyrazole and/or a formamidine, methods and uses thereof
TWI579274B (zh)	2012-04-20	2017-04-21	龍馬躍公司	製備１－芳基－５－烷基吡唑化合物的改良方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3609185A (en) *	1968-06-29	1971-09-28	B P Chemicals U K Ltd	Production of organic acids
US3742046A (en) *	1970-08-05	1973-06-26	Chemagro Corp	{60 -(dichlorovinylthio)-acetophenone
JPS50130761A (da)	1974-04-04	1975-10-16
US3937738A (en)	1974-04-25	1976-02-10	Minnesota Mining And Manufacturing Company	(perhaloalkyl) thio-substituted aldehydes and ketones
US3932508A (en) *	1974-04-26	1976-01-13	Minnesota Mining And Manufacturing Company	Polyfluoromethylthio-substituted compounds
IN140318B (da)	1974-12-27	1976-10-16	Dow Chemical Co
US4127575A (en)	1976-10-20	1978-11-28	The Dow Chemical Company	Preparation of chloro substituted pyridines
IL59748A (en)	1979-04-05	1983-11-30	Lilly Industries Ltd	5-substituted pyranone derivatives,their production and pharmaceutical compositions containing them
DK145684A (da)	1983-03-09	1984-09-10	May & Baker Ltd	N-pyridylpyrazol-derivater med herbicid aktivitet
GR80558B (en) *	1983-10-08	1985-02-06	Nippon Kayaku Kk	Derivative of pyrazole and use thereof as a herbicide
DE3402308A1 (de)	1984-01-24	1985-08-01	Bayer Ag, 5090 Leverkusen	Herbizide mittel auf basis von pyrazolderivaten
DE3509567A1 (de) *	1985-03-16	1986-09-18	Bayer Ag, 5090 Leverkusen	Herbizide und insektizide mittel auf basis von pyrazolderivaten
DE3602728A1 (de) *	1985-05-17	1986-11-20	Bayer Ag, 51373 Leverkusen	Schaedlingsbekaempfungsmittel auf basis von pyrazolderivaten
GB8531485D0 (en) *	1985-12-20	1986-02-05	May & Baker Ltd	Compositions of matter

1986
- 1986-01-08 DE DE19863600287 patent/DE3600287A1/de not_active Withdrawn
- 1986-12-19 AU AU66806/86A patent/AU596389B2/en not_active Ceased
- 1986-12-23 DE DE8686117971T patent/DE3674573D1/de not_active Expired - Lifetime
- 1986-12-23 ES ES198686117971T patent/ES2036172T3/es not_active Expired - Lifetime
- 1986-12-23 EP EP86117971A patent/EP0231510B1/de not_active Expired - Lifetime
- 1986-12-23 AT AT86117971T patent/ATE56959T1/de not_active IP Right Cessation
- 1986-12-30 US US06/947,800 patent/US4810720A/en not_active Expired - Lifetime
1987
- 1987-01-05 IL IL81161A patent/IL81161A0/xx unknown
- 1987-01-06 NZ NZ218806A patent/NZ218806A/xx unknown
- 1987-01-07 DD DD87299131A patent/DD257381A5/de unknown
- 1987-01-07 HU HU8751A patent/HU198692B/hu not_active IP Right Cessation
- 1987-01-07 DK DK006287A patent/DK6287A/da unknown
- 1987-01-07 ZA ZA8777A patent/ZA8777B/xx unknown
- 1987-01-07 PL PL1987263578A patent/PL263578A1/xx unknown
- 1987-01-08 KR KR870000071A patent/KR870007133A/ko not_active Withdrawn
- 1987-01-08 TR TR35/87A patent/TR23157A/xx unknown
- 1987-01-08 JP JP62001147A patent/JPH0819107B2/ja not_active Expired - Fee Related
- 1987-01-08 BR BR8700046A patent/BR8700046A/pt unknown
1990
- 1990-09-27 GR GR90400697T patent/GR3000881T3/el unknown

Also Published As

Publication number	Publication date
HUT42756A (en)	1987-08-28
IL81161A0 (en)	1987-08-31
GR3000881T3 (en)	1991-11-15
EP0231510A3 (en)	1988-02-03
TR23157A (tr)	1989-04-18
HU198692B (en)	1989-11-28
JPH0819107B2 (ja)	1996-02-28
ZA8777B (en)	1987-09-30
ATE56959T1 (de)	1990-10-15
DE3674573D1 (en)	1990-10-31
JPS62164669A (ja)	1987-07-21
DE3600287A1 (de)	1987-07-16
EP0231510B1 (de)	1990-09-26
KR870007133A (ko)	1987-08-17
AU6680686A (en)	1987-07-09
AU596389B2 (en)	1990-05-03
DK6287D0 (da)	1987-01-07
US4810720A (en)	1989-03-07
EP0231510A2 (de)	1987-08-12
NZ218806A (en)	1989-08-29
PL263578A1 (en)	1988-07-21
DK6287A (da)	1987-07-09
ES2036172T3 (es)	1993-05-16
BR8700046A (pt)	1987-12-01

Publication	Publication Date	Title
EP0201852B1 (de)	1990-08-16	Schädlingsbekämpfungsmittel auf Basis von Pyrazolderivaten
EP0235628B1 (de)	1991-04-24	1-Arylpyrazole
EP0231510B1 (de)	1990-09-26	1-Arylpyrazole
EP0200872B1 (de)	1990-04-18	Herbizide und insektizide Mittel auf Basis von Pyrazol-Derivaten
DD258164A5 (de)	1988-07-13	Schaedlingsbekaempfungmittel
DD256699A5 (de)	1988-05-18	Verfahren zur herstellung von 1-arylporozolen
EP0257479A1 (de)	1988-03-02	Substituierte 1-Aryl-3-tert.-butyl-pyrazole
DE3719732A1 (de)	1989-01-05	Substituierte 5-methylamino-1-arylpyrazole
DD285279A5 (de)	1990-12-12	Schaedlingsbekaempfungsmittel, insbesondere insektizide mittel
EP0249033A1 (de)	1987-12-16	5-Oxy(thio)-pyrazol-Derivate
EP0287851A1 (de)	1988-10-26	Substituierte 1-Arylpyrazole
EP0280991A1 (de)	1988-09-07	5-Amino-3-halogenalkyl-1-aryl-pyrazole
EP0392241B1 (de)	1993-06-02	Substituierte 1-Arylpyrazole
DE3712204A1 (de)	1988-10-27	3-halogenalkyl-1-aryl-pyrazole
DE3609423A1 (de)	1987-10-01	Schaedlingsbekaempfungsmittel auf basis von 1-aryl-4-trifluormethyl-5-aminopyrazolen
EP0302327A1 (de)	1989-02-08	3,5-Dialkyl-l-arylpyrazole
EP0295482A1 (de)	1988-12-21	Substituierte 5-Ethylamino-1-arylpyrazole
DE3726529A1 (de)	1989-02-23	1-arylpyrazole
DE3715703A1 (de)	1988-11-24	1-aryl-3-halogenalkyl-4-halogen-pyrazole
DE3712934A1 (de)	1988-11-03	Substituierte 1-arylpyrazole
DD248272A5 (de)	1987-08-05	Insektizide, akarizide und nematizide mittel