DD258164A5 - Schaedlingsbekaempfungmittel - Google Patents

Schaedlingsbekaempfungmittel Download PDF

Info

Publication number: DD258164A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; case; spp; hydrogen; pyridyl
Prior art date: 1985-08-21

Application number

DD86293733A

Other languages

German (de)

English (en)

Inventor

Uta Jensen-Korte

Reinhold Gehring

Otto Schallner

Joerg Stetter

Heinz-Juergen Wroblowsky

Benedikt Becker

Wilhelm Stendel

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.)

1985-08-21

Filing date

1986-08-19

Publication date

1988-07-13

1986-08-19 Application filed by ��@��k�� filed Critical ��@��k��

1988-07-13 Publication of DD258164A5 publication Critical patent/DD258164A5/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 57
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 22
239000000203 mixture Substances 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000004961 1-arylpyrazolyl group Chemical group 0.000 claims abstract description 19
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 19
150000002431 hydrogen Chemical group 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
229910052736 halogen Chemical group 0.000 claims abstract description 11
150000002367 halogens Chemical group 0.000 claims abstract description 10
230000000895 acaricidal effect Effects 0.000 claims abstract description 8
239000000575 pesticide Substances 0.000 claims abstract description 7
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
239000000460 chlorine Substances 0.000 claims description 208
-1 difluorochloromethyl Chemical group 0.000 claims description 48
238000002360 preparation method Methods 0.000 claims description 29
238000000034 method Methods 0.000 claims description 15
241000238631 Hexapoda Species 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
230000000749 insecticidal effect Effects 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 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
241000239223 Arachnida Species 0.000 claims description 4
241000244206 Nematoda Species 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
241000239290 Araneae Species 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000004438 haloalkoxy group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 claims 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
125000005998 bromoethyl group Chemical group 0.000 claims 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
239000002917 insecticide Substances 0.000 abstract description 4
239000000642 acaricide Substances 0.000 abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract description 3
230000000361 pesticidal effect Effects 0.000 abstract 1
238000012360 testing method Methods 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
239000002904 solvent Substances 0.000 description 32
241001465754 Metazoa Species 0.000 description 23
239000003085 diluting agent Substances 0.000 description 17
239000004480 active ingredient Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
238000005160 1H NMR spectroscopy Methods 0.000 description 15
239000002253 acid Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
238000009472 formulation Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000003995 emulsifying agent Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 8
241000238876 Acari Species 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
241000607479 Yersinia pestis Species 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000003814 drug Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000002689 soil Substances 0.000 description 7
241000255925 Diptera Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000003071 parasitic effect Effects 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000000126 substance Substances 0.000 description 5
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000254173 Coleoptera Species 0.000 description 4
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
229950005228 bromoform Drugs 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
125000003226 pyrazolyl group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 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
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
241001510236 Rhyparobia maderae Species 0.000 description 3
241001494115 Stomoxys calcitrans Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000011161 development Methods 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
MPXLVMGLMXJXPS-UHFFFAOYSA-N 5-(1h-pyrazol-5-yldisulfanyl)-1h-pyrazole Chemical class C1=CNN=C1SSC=1C=CNN=1 MPXLVMGLMXJXPS-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
241000238657 Blattella germanica Species 0.000 description 2
240000007124 Brassica oleracea Species 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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 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
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
241000258937 Hemiptera Species 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
244000046052 Phaseolus vulgaris Species 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
241000258242 Siphonaptera Species 0.000 description 2
241000254179 Sitophilus granarius Species 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
241001454295 Tetranychidae Species 0.000 description 2
241001454294 Tetranychus Species 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
KDRSHFSCTSFYGH-UHFFFAOYSA-N [dichloro(fluoro)methyl] thiohypochlorite Chemical compound FC(Cl)(Cl)SCl KDRSHFSCTSFYGH-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
150000008360 acrylonitriles Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000011609 ammonium molybdate Substances 0.000 description 2
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 2
235000018660 ammonium molybdate Nutrition 0.000 description 2
229940010552 ammonium molybdate Drugs 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000006193 diazotization reaction Methods 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
150000002170 ethers Chemical class 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
210000004209 hair Anatomy 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
150000003217 pyrazoles Chemical class 0.000 description 2
235000002639 sodium chloride Nutrition 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
235000019345 sodium thiosulphate Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
238000005507 spraying Methods 0.000 description 2
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
DWMGFASJKTZERP-UHFFFAOYSA-N 2-(2,4,6-trichlorophenyl)pyrazol-3-amine Chemical compound NC1=CC=NN1C1=C(Cl)C=C(Cl)C=C1Cl DWMGFASJKTZERP-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
NXJCLNYWBFNGKR-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound NC1=CC=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NXJCLNYWBFNGKR-UHFFFAOYSA-N 0.000 description 1
OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
XHZWFUVEKDDQPF-UHFFFAOYSA-N 5-bromo-1h-pyrazole Chemical class BrC1=CC=NN1 XHZWFUVEKDDQPF-UHFFFAOYSA-N 0.000 description 1
IJPFBRONCJOTTA-UHFFFAOYSA-N 5-chloro-1h-pyrazole Chemical class ClC1=CC=NN1 IJPFBRONCJOTTA-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
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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
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
239000012085 test solution Substances 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical group [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-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
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene 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
- 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)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (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)

DD86293733A 1985-08-21 1986-08-19 Schaedlingsbekaempfungmittel DD258164A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853529829 DE3529829A1 (de)	1985-08-21	1985-08-21	1-arylpyrazole

Publications (1)

Publication Number	Publication Date
DD258164A5 true DD258164A5 (de)	1988-07-13

Family

ID=6278961

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86293733A DD258164A5 (de)	1985-08-21	1986-08-19	Schaedlingsbekaempfungmittel

Country Status (22)

Country	Link
US (1)	US4820725A (fr)
EP (1)	EP0216102A1 (fr)
JP (1)	JPS6245577A (fr)
KR (1)	KR870002080A (fr)
CN (1)	CN86105140A (fr)
AU (1)	AU6114286A (fr)
BR (1)	BR8603971A (fr)
DD (1)	DD258164A5 (fr)
DE (1)	DE3529829A1 (fr)
DK (1)	DK397086A (fr)
ES (1)	ES2001106A6 (fr)
FI (1)	FI863350A7 (fr)
GR (1)	GR862156B (fr)
HU (1)	HUT45024A (fr)
IL (1)	IL79756A0 (fr)
MA (1)	MA20756A1 (fr)
OA (1)	OA08389A (fr)
PL (1)	PL261086A1 (fr)
PT (1)	PT83184A (fr)
SU (1)	SU1447265A3 (fr)
ZA (1)	ZA866277B (fr)
ZW (1)	ZW15386A1 (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3520330A1 (de) *	1985-06-07	1986-12-11	Bayer Ag, 5090 Leverkusen	5-amino-1-pyridyl-pyrazole
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
GB8531485D0 (en) *	1985-12-20	1986-02-05	May & Baker Ltd	Compositions of matter
US5232940A (en) *	1985-12-20	1993-08-03	Hatton Leslie R	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
DE3727260A1 (de) *	1987-08-15	1989-02-23	Bayer Ag	1-arylpyrazole
DE3742822A1 (de) *	1987-12-17	1989-07-13	Bayer Ag	Verfahren zur herstellung von 5-amino-l-phenyl-4-nitro-pyrazolen
IL112721A0 (en) *	1994-03-10	1995-05-26	Zeneca Ltd	Azole derivatives
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
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
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
EP3412659A1 (fr)	2017-06-09	2018-12-12	Solvay Sa	Procédé de fabrication de dérivés pyrazole substitués par du soufre
EP3412658A1 (fr)	2017-06-09	2018-12-12	Solvay Sa	Procédés pour la préparation de dérivés de pyrazole substitués par un soufre
CN109651343B (zh) *	2019-01-07	2020-06-19	中南民族大学	一种氟虫腈吡唑醇环酰亚胺化合物及其微波水热法方法与应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2409753A1 (de) *	1974-03-01	1975-09-11	Basf Ag	Substituierte pyrazole
DE2839270A1 (de) *	1978-09-09	1980-03-20	Bayer Ag	N,n-dimethyl-o-pyrazolyl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
DE2935164A1 (de) *	1979-08-31	1981-03-26	Basf Ag, 67063 Ludwigshafen	Verfahren zur herstellung von 1,2,4-triazolen
GB2073172A (en) *	1980-04-03	1981-10-14	Shell Int Research	Pesticidal Pyrazole Derivatives
GR80558B (en) *	1983-10-08	1985-02-06	Nippon Kayaku Kk	Derivative of pyrazole and use thereof as a herbicide
IL73419A (en) *	1983-11-07	1988-02-29	Lilly Co Eli	1h-pyrazole-4-(thio)carboxamide derivatives,their preparation and herbicidal compositions containing them

1985
- 1985-08-21 DE DE19853529829 patent/DE3529829A1/de not_active Withdrawn
1986
- 1986-08-04 ZW ZW153/86A patent/ZW15386A1/xx unknown
- 1986-08-04 US US06/893,133 patent/US4820725A/en not_active Expired - Fee Related
- 1986-08-11 EP EP86111075A patent/EP0216102A1/fr not_active Withdrawn
- 1986-08-11 PT PT83184A patent/PT83184A/pt unknown
- 1986-08-13 SU SU864027940A patent/SU1447265A3/ru active
- 1986-08-14 JP JP61189736A patent/JPS6245577A/ja active Pending
- 1986-08-14 AU AU61142/86A patent/AU6114286A/en not_active Abandoned
- 1986-08-18 OA OA58933A patent/OA08389A/fr unknown
- 1986-08-18 IL IL79756A patent/IL79756A0/xx unknown
- 1986-08-19 GR GR862156A patent/GR862156B/el unknown
- 1986-08-19 MA MA20984A patent/MA20756A1/fr unknown
- 1986-08-19 FI FI863350A patent/FI863350A7/fi not_active Application Discontinuation
- 1986-08-19 DD DD86293733A patent/DD258164A5/de unknown
- 1986-08-20 PL PL1986261086A patent/PL261086A1/xx unknown
- 1986-08-20 ZA ZA866277A patent/ZA866277B/xx unknown
- 1986-08-20 KR KR1019860006865A patent/KR870002080A/ko not_active Withdrawn
- 1986-08-20 DK DK397086A patent/DK397086A/da not_active Application Discontinuation
- 1986-08-20 ES ES8601223A patent/ES2001106A6/es not_active Expired
- 1986-08-20 BR BR8603971A patent/BR8603971A/pt unknown
- 1986-08-21 CN CN198686105140A patent/CN86105140A/zh active Pending
- 1986-08-21 HU HU863641A patent/HUT45024A/hu unknown

Also Published As

Publication number	Publication date
DK397086A (da)	1987-02-22
IL79756A0 (en)	1986-11-30
HUT45024A (en)	1988-05-30
ZA866277B (en)	1988-04-27
OA08389A (fr)	1988-02-29
CN86105140A (zh)	1987-02-25
ZW15386A1 (en)	1986-10-29
FI863350A0 (fi)	1986-08-19
KR870002080A (ko)	1987-03-30
PL261086A1 (en)	1988-07-21
FI863350L (fi)	1987-02-22
US4820725A (en)	1989-04-11
BR8603971A (pt)	1987-03-31
DE3529829A1 (de)	1987-02-26
JPS6245577A (ja)	1987-02-27
PT83184A (en)	1986-09-01
GR862156B (en)	1986-12-23
AU6114286A (en)	1987-02-26
ES2001106A6 (es)	1988-04-16
FI863350A7 (fi)	1987-02-22
DK397086D0 (da)	1986-08-20
SU1447265A3 (ru)	1988-12-23
EP0216102A1 (fr)	1987-04-01
MA20756A1 (fr)	1987-04-01

Publication	Publication Date	Title
EP0201852B1 (fr)	1990-08-16	Agent contre des plantes nuisibles à base de dérivés de pyrazole
EP0235628B1 (fr)	1991-04-24	1-Arylpyrazoles
EP0231510B1 (fr)	1990-09-26	1-Arylpyrazoles
DD258164A5 (de)	1988-07-13	Schaedlingsbekaempfungmittel
EP0233341A1 (fr)	1987-08-26	Hétérocyclique-5-aryl-1-pyrazoles
DE4032089A1 (de)	1991-07-25	Substituierte pyrazolinderivate
DE3719732A1 (de)	1989-01-05	Substituierte 5-methylamino-1-arylpyrazole
DE3628892A1 (de)	1988-03-10	Substituierte 1-aryl-3-tert.-butyl-pyrazole
DE3724919A1 (de)	1989-02-09	1-arylpyrazole
DE3617554A1 (de)	1987-11-26	5-oxy(thio)-pyrazol-derivate
EP0301339A1 (fr)	1989-02-01	Aryl-1(hétéro)arylméthylamino-5 pyrazoles substitués
EP0287851A1 (fr)	1988-10-26	1-Arylpyrazoles substitués
EP0392241B1 (fr)	1993-06-02	Aryl-1-pyrazoles substitués
EP0280991A1 (fr)	1988-09-07	Amino-5 halogénalcoyle-3 aryle-1 pyrazoles
DE3609423A1 (de)	1987-10-01	Schaedlingsbekaempfungsmittel auf basis von 1-aryl-4-trifluormethyl-5-aminopyrazolen
DE3712204A1 (de)	1988-10-27	3-halogenalkyl-1-aryl-pyrazole
EP0683770A1 (fr)	1995-11-29	Carboxamides de tetrahydropyridazine substitues
DE4233713A1 (de)	1994-04-14	Substituierte 4,5-Dihydro-1-pyrazolcarbonsäureanilide
DE3719733A1 (de)	1989-01-05	Substituierte 5-ethylamino-1-arylpyrazole
EP0303118A2 (fr)	1989-02-15	Aryl-1-pyrazoles
EP0302327A1 (fr)	1989-02-08	3,5-Dialkyl-1-arylpyrazoles
EP0532918A1 (fr)	1993-03-24	Pyrazolines substitués comme pesticides
EP0515893A1 (fr)	1992-12-02	Hétéroaryl-4-pyrazolines substitués