IL95307A - Azul compounds and preparations containing them for killing insect mites and endoplasms of animals - Google Patents

Azul compounds and preparations containing them for killing insect mites and endoplasms of animals

Info

Publication number: IL95307A
Authority: IL; Israel
Prior art keywords: compound; dichloro; trifluoromethylphenyl; optionally substituted; alkyl
Prior art date: 1989-08-10

Application number

IL9530790A

Other languages

English (en)

Hebrew (he)

Other versions

IL95307A0 (en

Original Assignee

Schering Agrochemicals Ltd

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.)

1989-08-10

Filing date

1990-08-07

Publication date

1995-11-27

1989-08-10 Priority claimed from GB898918314A external-priority patent/GB8918314D0/en

1990-03-24 Priority claimed from GB909006653A external-priority patent/GB9006653D0/en

1990-08-07 Application filed by Schering Agrochemicals Ltd filed Critical Schering Agrochemicals Ltd

1991-06-30 Publication of IL95307A0 publication Critical patent/IL95307A0/xx

1995-11-27 Publication of IL95307A publication Critical patent/IL95307A/en

Links

239000000203 mixture Substances 0.000 title claims description 89
230000000749 insecticidal effect Effects 0.000 title description 8
230000000895 acaricidal effect Effects 0.000 title description 6
150000003851 azoles Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 178
-1 YR<2><0> Chemical group 0.000 claims abstract description 95
125000000217 alkyl group Chemical group 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052736 halogen Inorganic materials 0.000 claims abstract description 21
150000002367 halogens Chemical class 0.000 claims abstract description 21
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
125000003118 aryl group Chemical group 0.000 claims abstract description 19
125000002252 acyl group Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 13
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
241001465754 Metazoa Species 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
230000000361 pesticidal effect Effects 0.000 claims abstract description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
244000079386 endoparasite Species 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
241000238631 Hexapoda Species 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000005017 substituted alkenyl group Chemical group 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
238000000034 method Methods 0.000 claims description 17
125000004414 alkyl thio group Chemical group 0.000 claims description 12
239000003085 diluting agent Substances 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
241000607479 Yersinia pestis Species 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 5
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000004438 haloalkoxy group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
102200029950 rs35898499 Human genes 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 abstract description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 9
125000000623 heterocyclic group Chemical group 0.000 abstract description 7
125000005842 heteroatom Chemical group 0.000 abstract description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
239000002904 solvent Substances 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
238000010992 reflux Methods 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 25
239000000047 product Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
239000000284 extract Substances 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 17
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
238000010626 work up procedure Methods 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
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 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
241000736227 Lucilia sericata Species 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000000843 powder Substances 0.000 description 8
241000244206 Nematoda Species 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
241000699670 Mus sp. Species 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 5
239000001117 sulphuric acid Substances 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000001665 trituration Methods 0.000 description 5
229910052721 tungsten Inorganic materials 0.000 description 5
ITNMAZSPBLRJLU-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)aniline Chemical compound NC1=C(Cl)C=C(C(F)(F)F)C=C1Cl ITNMAZSPBLRJLU-UHFFFAOYSA-N 0.000 description 4
241000238876 Acari Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 4
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000013058 crude material Substances 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
238000001035 drying Methods 0.000 description 4
235000013601 eggs Nutrition 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 3
KLLJJCBRSVAMLJ-UHFFFAOYSA-N 2-[2-[2,6-dichloro-4-(trifluoromethyl)phenyl]triazol-4-yl]-1H-imidazole-4,5-dicarbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1N=C(C=2NC(=C(C#N)N=2)C#N)C=N1 KLLJJCBRSVAMLJ-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
241000257159 Musca domestica Species 0.000 description 3
241001556089 Nilaparvata lugens Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241001454293 Tetranychus urticae Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Chemical group 0.000 description 3
229940125797 compound 12 Drugs 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000010410 dusting Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
230000001850 reproductive effect Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000002689 soil Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
150000003852 triazoles Chemical class 0.000 description 3
ASQOQJYHIYYTEJ-GBESFXJTSA-N (1r,7s,9as)-7-decyl-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-ol Chemical compound O[C@@H]1CCCN2C[C@@H](CCCCCCCCCC)CC[C@H]21 ASQOQJYHIYYTEJ-GBESFXJTSA-N 0.000 description 2
IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 2
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
XMZVRBTYQVIYKH-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]triazole-4-carbaldehyde Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1N=C(C=O)C=N1 XMZVRBTYQVIYKH-UHFFFAOYSA-N 0.000 description 2
MLOXIXGLIZLPDP-UHFFFAOYSA-N 2-amino-1h-imidazole-4,5-dicarbonitrile Chemical compound NC1=NC(C#N)=C(C#N)N1 MLOXIXGLIZLPDP-UHFFFAOYSA-N 0.000 description 2
GBJLTTHEBKXDRI-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-methylpyrazole-4-carbaldehyde Chemical compound NC1=C(C=O)C(C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GBJLTTHEBKXDRI-UHFFFAOYSA-N 0.000 description 2
UCYPHJSXEHPSFQ-UHFFFAOYSA-N 5-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-methylpyrazole-4-carbaldehyde Chemical compound ClC1=C(C=O)C(C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl UCYPHJSXEHPSFQ-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
241001124076 Aphididae Species 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
241000243785 Meloidogyne javanica Species 0.000 description 2
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JUHMHPOXZAYYJP-UHFFFAOYSA-N ethyl 5-amino-1-(4-methylphenyl)sulfonylpyrazole-4-carboxylate Chemical class NC1=C(C(=O)OCC)C=NN1S(=O)(=O)C1=CC=C(C)C=C1 JUHMHPOXZAYYJP-UHFFFAOYSA-N 0.000 description 1
YCJZANWKLAEPMR-UHFFFAOYSA-N ethyl 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-4-carboxylate Chemical compound BrC1=C(C(=O)OCC)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YCJZANWKLAEPMR-UHFFFAOYSA-N 0.000 description 1
CFRQJQQYBFNEMH-UHFFFAOYSA-N ethyl 5-bromo-1-[2-nitro-4-(trifluoromethyl)phenyl]pyrazole-4-carboxylate Chemical compound BrC1=C(C(=O)OCC)C=NN1C1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O CFRQJQQYBFNEMH-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002194 fatty esters Chemical class 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000002316 fumigant Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
244000000013 helminth Species 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000001524 infective effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000006028 limestone Substances 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
SJDBEROAEMAOJW-UHFFFAOYSA-N methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate Chemical compound COC(=O)C(C#N)=C(SC)SC SJDBEROAEMAOJW-UHFFFAOYSA-N 0.000 description 1
DUZTVXKYJROMJJ-UHFFFAOYSA-N methyl 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-3-methylsulfanylpyrazole-4-carboxylate Chemical compound N1=C(SC)C(C(=O)OC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DUZTVXKYJROMJJ-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ZXNXJFBNNQBFBC-UHFFFAOYSA-N n-[2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methylpyrazol-3-yl]-n-methylformamide Chemical compound O=CN(C)C1=CC(C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZXNXJFBNNQBFBC-UHFFFAOYSA-N 0.000 description 1
125000005609 naphthenate group Chemical group 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000000590 parasiticidal effect Effects 0.000 description 1
239000002297 parasiticide Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
244000000040 protozoan parasite Species 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 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
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
JYRWUSXRTGACLY-UHFFFAOYSA-N tert-butyl 4-[[3-(4-methylsulfonylphenyl)-[1,2]oxazolo[4,5-d]pyrimidin-7-yl]oxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC2=C1ON=C2C1=CC=C(S(C)(=O)=O)C=C1 JYRWUSXRTGACLY-UHFFFAOYSA-N 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene 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
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL9530790A 1989-08-10 1990-08-07 Azul compounds and preparations containing them for killing insect mites and endoplasms of animals IL95307A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB898918314A GB8918314D0 (en)	1989-08-10	1989-08-10	Pesticides
GB909006653A GB9006653D0 (en)	1990-03-24	1990-03-24	Azole pesticides

Publications (2)

Publication Number	Publication Date
IL95307A0 IL95307A0 (en)	1991-06-30
IL95307A true IL95307A (en)	1995-11-27

Family

ID=26295733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9530790A IL95307A (en)	1989-08-10	1990-08-07	Azul compounds and preparations containing them for killing insect mites and endoplasms of animals

Country Status (22)

Country	Link
US (1)	US5109012A (de)
EP (1)	EP0412849B1 (de)
JP (1)	JPH0383981A (de)
KR (1)	KR910004601A (de)
CN (1)	CN1025582C (de)
AP (1)	AP173A (de)
AT (1)	ATE131820T1 (de)
AU (1)	AU627064B2 (de)
BR (1)	BR9003935A (de)
CA (1)	CA2022993A1 (de)
DE (1)	DE69024281T2 (de)
DK (1)	DK0412849T3 (de)
ES (1)	ES2082828T3 (de)
FI (1)	FI95379C (de)
GR (1)	GR3019353T3 (de)
HU (1)	HU208228B (de)
IE (1)	IE902898A1 (de)
IL (1)	IL95307A (de)
OA (1)	OA09459A (de)
PT (1)	PT94956B (de)
TR (1)	TR26035A (de)
YU (1)	YU47834B (de)

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FR2739255B1 (fr) *	1995-09-29	1998-09-04	Rhone Merieux	Composition antiparasitaire pour le traitement et la protection des animaux de compagnie
AU2003257646B2 (en) *	1996-03-29	2006-03-30	Merial	Direct pour-on skin solution for anitparasitic use in cattle and sheep
IE970215A1 (en) *	1996-03-29	1997-10-08	Rhone Merieux	Direct pour-on skin solution for antiparasitic use in cattle¹and sheep
AU736854B2 (en)	1996-04-25	2001-08-02	Nissan Chemical Industries Ltd.	Ethylene derivatives and pesticides containing said derivatives
GB9625045D0 (en) *	1996-11-30	1997-01-22	Pfizer Ltd	Parasiticidal compounds
HU229905B1 (en) *	1996-12-24	2014-12-29	Merial Ltd	Pesticidal 1-arylpyrazoles
ZA9711534B (en)	1996-12-24	1998-06-24	Rhone Poulenc Agrochimie	Pesticidal 1-arylpyrazoles.
US6350771B1 (en)	1996-12-24	2002-02-26	Rhone-Poulenc, Inc.	Pesticidal 1-arylpyrazoles
EP0911329A1 (de) *	1997-10-07	1999-04-28	Rhone-Poulenc Agro	3-substituierte arylpyrazol-derivate
US5981565A (en)	1997-10-07	1999-11-09	Rhone-Poulenc Inc.	Pyrazole pesticides
US6107314A (en)	1997-10-07	2000-08-22	Rhone-Poulenc Inc.	Pesticides
ES2280087T3 (es) *	1998-05-07	2007-09-01	Basf Agro B.V., Arnhem (Nl), Wadenswil-Branch	Metodo plaguicida.
EP0968651A1 (de) *	1998-07-01	2000-01-05	Rhone-Poulenc Agriculture Ltd.	Verfahren und Zusammensetzung zur Schädlingsbekämpfung
KR20010108050A (ko)	1998-12-25	2001-12-07	도쿠시마 히데이치	아크릴로니트릴 화합물
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US6409988B1 (en)	1999-07-01	2002-06-25	3-Dimensional Pharmaceuticals, Inc.	Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands
WO2001007413A1 (en) *	1999-07-22	2001-02-01	3-Dimensional Pharmaceuticals, Inc.	1-aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides
WO2001025241A2 (en)	1999-10-06	2001-04-12	3-Dimensional Pharmaceuticals, Inc.	Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides
TW200306783A (en) *	2002-04-29	2003-12-01	Fmc Corp	Pesticidal heterocycles
FR2853902B1 (fr) *	2003-04-17	2005-06-24	Evultis	Procede de synthese de composes insecticides
US20090018178A1 (en) *	2003-11-04	2009-01-15	Akzo Nobel N.V.	Use of haloarylpyrazole compounds in the control of parasite infestation on animals
DE602004017347D1 (de) *	2003-11-04	2008-12-04	Intervet Int Bv	Azol-pestiziden
JP4664924B2 (ja)	2003-12-02	2011-04-06	ウーツェーベーファルマゲーエムベーハー	中枢神経因性疼痛の治療のためのペプチド化合物の新規使用
WO2006010767A1 (en)	2004-07-28	2006-02-02	Intervet International B.V.	Veterinary composition comprising an arylpyrazole and a nitroenamine with enhanced antiparasitic activity
UY28617A1 (es) *	2004-11-12	2006-06-30	Popley Pharma Ltda	Nuevas composiciones
WO2006134459A1 (en) *	2005-06-15	2006-12-21	Pfizer Limited	Substituted arylpyrazoles
BR112012006956A2 (pt) *	2009-10-12	2015-09-15	Bayer Cropscience Ag	1- (pirida-3-il) -pirazóisol e 1- (pirimida-5-il) - pirazóisol como pesticidas
KR20130038842A (ko)	2010-03-18	2013-04-18	신젠타 파티서페이션즈 아게	살충성 화합물
CN103261188A (zh) *	2010-12-17	2013-08-21	先正达参股股份有限公司	杀虫化合物
BR112013020213A2 (pt) *	2011-02-09	2016-08-02	Syngenta Participations Ag	compostos inseticidas
MX2014006072A (es)	2011-11-25	2014-08-08	Bayer Ip Gmbh	Derivados de 2-yodo-imidazol.
FR2991323B1 (fr)	2012-06-04	2014-06-13	Arkema France	Sel d'anions bicycliques aromatiques pour batteries li-ion
FR2991324B1 (fr)	2012-06-04	2014-06-13	Arkema France	Sel d'anions bicycliques aromatiques pour batteries li-ion
TW201418242A (zh) *	2012-10-26	2014-05-16	Du Pont	作為除草劑之經取代的三唑
DE102014005771A1 (de)	2014-04-23	2015-10-29	Clariant International Ltd.	Verwendung von wässrigen driftreduzierenden Zusammensetzungen
DE102014012022A1 (de) *	2014-08-13	2016-02-18	Clariant International Ltd.	Organische Ammoniumsalze von anionischen Pestiziden
RU2591206C1 (ru) *	2015-04-14	2016-07-20	Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Российский химико-технологический университет имени Д.И. Менделеева (РХТУ им. Д.И. Менделеева)"	Замещенные 1-(1-трет-бутил-1н-имидазол-4-ил)-1н-1,2,3-триазолы, способ их получения и фунгицидная композиция на их основе
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1990
- 1990-08-01 YU YU149390A patent/YU47834B/sh unknown
- 1990-08-07 IL IL9530790A patent/IL95307A/en active IP Right Grant
- 1990-08-07 OA OA59831A patent/OA09459A/xx unknown
- 1990-08-08 AP APAP/P/1990/000196A patent/AP173A/en active
- 1990-08-08 US US07/564,729 patent/US5109012A/en not_active Expired - Fee Related
- 1990-08-09 BR BR909003935A patent/BR9003935A/pt not_active Application Discontinuation
- 1990-08-09 AU AU60846/90A patent/AU627064B2/en not_active Ceased
- 1990-08-09 HU HU904951A patent/HU208228B/hu not_active IP Right Cessation
- 1990-08-09 JP JP2209367A patent/JPH0383981A/ja active Pending
- 1990-08-09 PT PT94956A patent/PT94956B/pt not_active IP Right Cessation
- 1990-08-09 FI FI903944A patent/FI95379C/fi not_active IP Right Cessation
- 1990-08-09 CA CA002022993A patent/CA2022993A1/en not_active Abandoned
- 1990-08-09 IE IE289890A patent/IE902898A1/en unknown
- 1990-08-10 EP EP90308857A patent/EP0412849B1/de not_active Expired - Lifetime
- 1990-08-10 CN CN90106995A patent/CN1025582C/zh not_active Expired - Fee Related
- 1990-08-10 KR KR1019900012410A patent/KR910004601A/ko not_active Ceased
- 1990-08-10 ES ES90308857T patent/ES2082828T3/es not_active Expired - Lifetime
- 1990-08-10 DK DK90308857.3T patent/DK0412849T3/da active
- 1990-08-10 DE DE69024281T patent/DE69024281T2/de not_active Expired - Fee Related
- 1990-08-10 TR TR90/0732A patent/TR26035A/xx unknown
- 1990-08-10 AT AT90308857T patent/ATE131820T1/de not_active IP Right Cessation
1996
- 1996-03-19 GR GR960400749T patent/GR3019353T3/el unknown

Also Published As

Publication number	Publication date
HU904951D0 (en)	1991-01-28
PT94956A (pt)	1991-04-18
YU149390A (sh)	1992-09-07
KR910004601A (ko)	1991-03-29
AU627064B2 (en)	1992-08-13
IL95307A0 (en)	1991-06-30
FI903944A0 (fi)	1990-08-09
DE69024281D1 (de)	1996-02-01
EP0412849A2 (de)	1991-02-13
DE69024281T2 (de)	1996-07-04
FI95379C (fi)	1996-01-25
FI95379B (fi)	1995-10-13
OA09459A (en)	1992-11-15
JPH0383981A (ja)	1991-04-09
ES2082828T3 (es)	1996-04-01
TR26035A (tr)	1993-11-01
ATE131820T1 (de)	1996-01-15
EP0412849A3 (en)	1992-04-15
CN1049341A (zh)	1991-02-20
PT94956B (pt)	1997-05-28
HUT54462A (en)	1991-03-28
IE902898A1 (en)	1991-02-27
HU208228B (en)	1993-09-28
CN1025582C (zh)	1994-08-10
AP173A (en)	1992-03-05
AP9000196A0 (en)	1990-10-31
AU6084690A (en)	1991-02-14
EP0412849B1 (de)	1995-12-20
DK0412849T3 (da)	1996-04-22
YU47834B (sr)	1996-01-09
US5109012A (en)	1992-04-28
GR3019353T3 (en)	1996-06-30
BR9003935A (pt)	1991-09-03
CA2022993A1 (en)	1991-02-11

Legal Events

Date	Code	Title
1996-05-14	FF	Patent granted
1996-10-31	FF	Patent granted
2000-10-31	KB	Patent renewed
2000-11-21	HP	Change in proprietorship
2004-09-27	KB	Patent renewed
2008-11-27	KB	Patent renewed

Publication	Publication Date	Title
AP173A (en)	1992-03-05	Azole Pesticides.
US6087387A (en)	2000-07-11	Pesticidal 1-arylpyrazoles
WO1992013451A1 (en)	1992-08-20	Imidazole pesticides
US6350771B1 (en)	2002-02-26	Pesticidal 1-arylpyrazoles
CA2010180C (en)	2000-04-18	Pesticidal 3-cyano-5-alkoxy-1-arylpyrazoles
US6069157A (en)	2000-05-30	Parasiticidal compounds
IE892291L (en)	1990-01-15	Derivatives of n-phenylpyrazoles
JPS6368567A (ja)	1988-03-28	新規複素環式化合物及び殺虫剤
US5064844A (en)	1991-11-12	1,2,3-triazole insecticides
AU745011B2 (en)	2002-03-07	Pesticidal 1-Aryl-3-iminopyrazoles
US5629335A (en)	1997-05-13	Pesticidal 1-arylpyrazole-3-carboximidothioic acid esters
JPS61215371A (ja)	1986-09-25	ピラゾール誘導体、その製造方法、除草剤および殺昆虫剤
EP0839810A1 (de)	1998-05-06	1-Polyarylpyrazole als Pestizide
JPS62283961A (ja)	1987-12-09	５−オキシ（チオ）ビラゾ−ル誘導体
US5189053A (en)	1993-02-23	Imidazol(in)e substituted haloarylpyrazole pesticides
DD298101A5 (de)	1992-02-06	Substituierte aryltriazole und deren verwendung als pestizide
JPH05230029A (ja)	1993-09-07	含フッ素ピラゾール化合物、その製法及び有害生物防除剤
US6638956B2 (en)	2003-10-28	Pesticidal 1-arylpyrazoles
US5124333A (en)	1992-06-23	Aminopyrimidine derivatives and harmful organisms preventive agent
JPS63215673A (ja)	1988-09-08	ピリダジノン化合物および病害虫防除剤
JPH06100560A (ja)	1994-04-12	オキサゾリン誘導体、その製法及び殺虫殺ダニ、殺菌剤