ZA200603762B - Active agent combinations with insecticidal and acaricidal properties - Google Patents
Active agent combinations with insecticidal and acaricidal properties Download PDFInfo
- Publication number
- ZA200603762B ZA200603762B ZA200603762A ZA200603762A ZA200603762B ZA 200603762 B ZA200603762 B ZA 200603762B ZA 200603762 A ZA200603762 A ZA 200603762A ZA 200603762 A ZA200603762 A ZA 200603762A ZA 200603762 B ZA200603762 B ZA 200603762B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- alkoxy
- haloalkyl
- optionally
- halogen
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title abstract description 10
- 230000000749 insecticidal effect Effects 0.000 title description 7
- 239000013543 active substance Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 50
- 150000002367 halogens Chemical class 0.000 claims abstract description 49
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 23
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 239000000575 pesticide Substances 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 182
- 239000000460 chlorine Substances 0.000 claims description 176
- 150000001875 compounds Chemical class 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 63
- 229910052801 chlorine Inorganic materials 0.000 claims description 57
- 229910052794 bromium Inorganic materials 0.000 claims description 51
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 50
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 47
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 46
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 239000011737 fluorine Substances 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 125000001153 fluoro group Chemical group F* 0.000 claims description 33
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims description 31
- 239000005930 Spinosad Substances 0.000 claims description 31
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 31
- 229940014213 spinosad Drugs 0.000 claims description 31
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 30
- 239000005660 Abamectin Substances 0.000 claims description 30
- 229950008167 abamectin Drugs 0.000 claims description 30
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004076 pyridyl group Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical class [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 4
- 150000003217 pyrazoles Chemical class 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical class 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical class 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 125000000335 thiazolyl group Chemical class 0.000 claims description 3
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 claims description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical class C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 claims description 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 2
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 claims description 2
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims description 2
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims description 2
- 239000005651 Acequinocyl Substances 0.000 claims description 2
- 239000005653 Bifenazate Substances 0.000 claims description 2
- 239000005874 Bifenthrin Substances 0.000 claims description 2
- 239000005654 Clofentezine Substances 0.000 claims description 2
- 239000005897 Etoxazole Substances 0.000 claims description 2
- 239000005656 Fenazaquin Substances 0.000 claims description 2
- 239000005657 Fenpyroximate Substances 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- 239000005661 Hexythiazox Substances 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000005918 Milbemectin Substances 0.000 claims description 2
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005663 Pyridaben Substances 0.000 claims description 2
- 239000005658 Tebufenpyrad Substances 0.000 claims description 2
- QDRXWCAVUNHOGA-UHFFFAOYSA-N acequinocyl Chemical group C1=CC=C2C(=O)C(CCCCCCCCCCCC)=C(OC(C)=O)C(=O)C2=C1 QDRXWCAVUNHOGA-UHFFFAOYSA-N 0.000 claims description 2
- ONHBDDJJTDTLIR-UHFFFAOYSA-N azocyclotin Chemical compound C1CCCCC1[Sn](N1N=CN=C1)(C1CCCCC1)C1CCCCC1 ONHBDDJJTDTLIR-UHFFFAOYSA-N 0.000 claims description 2
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 claims description 2
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- FOANIXZHAMJWOI-UHFFFAOYSA-N bromopropylate Chemical compound C=1C=C(Br)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Br)C=C1 FOANIXZHAMJWOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims description 2
- UXADOQPNKNTIHB-UHFFFAOYSA-N clofentezine Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 UXADOQPNKNTIHB-UHFFFAOYSA-N 0.000 claims description 2
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical group C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 claims description 2
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 claims description 2
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims description 2
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 2
- 229960002418 ivermectin Drugs 0.000 claims description 2
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000002918 oxazolines Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002728 pyrethroid Substances 0.000 claims description 2
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 claims description 2
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims description 2
- SRJQTHAZUNRMPR-UHFFFAOYSA-N spinosyn A Natural products CC1C(=O)C2=CC3C4CC(OC5C(C(OC)C(OC)C(C)O5)OC)CC4C=CC3C2CC(=O)OC(CC)CCCC1OC1CCC(N(C)C)C(C)O1 SRJQTHAZUNRMPR-UHFFFAOYSA-N 0.000 claims description 2
- SRJQTHAZUNRMPR-UYQKXTDMSA-N spinosyn A Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O1)OC)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 SRJQTHAZUNRMPR-UYQKXTDMSA-N 0.000 claims description 2
- VESRDXZDAAOUHS-KXRJSVEISA-N spinosyn B Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O1)OC)CC)[C@H]1CC[C@H](NC)[C@@H](C)O1 VESRDXZDAAOUHS-KXRJSVEISA-N 0.000 claims description 2
- RDECBWLKMPEKPM-UHFFFAOYSA-N spinosyn D Natural products CC1C(=O)C2=CC3C4CC(OC5C(C(OC)C(OC)C(C)O5)OC)CC4C(C)=CC3C2CC(=O)OC(CC)CCCC1OC1CCC(N(C)C)C(C)O1 RDECBWLKMPEKPM-UHFFFAOYSA-N 0.000 claims description 2
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 2
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 claims description 2
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 claims description 2
- 150000004905 tetrazines Chemical class 0.000 claims description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
- 150000003585 thioureas Chemical class 0.000 claims description 2
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 10
- 125000003545 alkoxy group Chemical group 0.000 abstract 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 abstract 3
- 239000000642 acaricide Substances 0.000 abstract 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 2
- JZQBAGOECGRTSA-UHFFFAOYSA-N 3-hydroxy-2h-furan-5-one Chemical class OC1=CC(=O)OC1 JZQBAGOECGRTSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 239000011885 synergistic combination Substances 0.000 abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 abstract 1
- 229940122578 Acetylcholine receptor agonist Drugs 0.000 abstract 1
- 229940121683 Acetylcholine receptor antagonist Drugs 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000002141 anti-parasite Effects 0.000 abstract 1
- 239000003096 antiparasitic agent Substances 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 239000005645 nematicide Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 1
- 150000008047 benzoylureas Chemical class 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical class NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10353281A DE10353281A1 (de) | 2003-11-14 | 2003-11-14 | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603762B true ZA200603762B (en) | 2007-12-27 |
Family
ID=34585116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200603762A ZA200603762B (en) | 2003-11-14 | 2006-05-11 | Active agent combinations with insecticidal and acaricidal properties |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8299036B2 (zh) |
| EP (2) | EP1686858B8 (zh) |
| JP (1) | JP4754495B2 (zh) |
| KR (1) | KR100858869B1 (zh) |
| CN (2) | CN1901798B (zh) |
| AT (1) | ATE425666T1 (zh) |
| AU (1) | AU2004290501C1 (zh) |
| BR (1) | BRPI0416035B1 (zh) |
| DE (2) | DE10353281A1 (zh) |
| ES (2) | ES2322364T3 (zh) |
| IL (1) | IL175582A0 (zh) |
| PL (1) | PL1686858T3 (zh) |
| PT (1) | PT1982594E (zh) |
| WO (1) | WO2005048712A1 (zh) |
| ZA (1) | ZA200603762B (zh) |
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| DE4426753A1 (de) * | 1994-07-28 | 1996-02-01 | Bayer Ag | Mittel zur Bekämpfung von Pflanzenschädlingen |
| PL198287B1 (pl) * | 1998-06-10 | 2008-06-30 | Bayer Ag | Środki do zwalczania szkodników roślin, sposób zwalczania owadów, zastosowanie kombinacji substancji czynnych i sposó wytwarzania środków do zwalczania szkodników |
| AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| TWI312274B (en) | 2001-08-13 | 2009-07-21 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| DE10228102A1 (de) * | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DE10228103A1 (de) * | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| UA81791C2 (uk) | 2003-01-28 | 2008-02-11 | Е.І. Дю Пон Дэ Нэмур Энд Компани | Ціаноантраніламідні сполуки, композиція та спосіб регулювання кількості шкідників |
| DE10335183A1 (de) * | 2003-07-30 | 2005-02-24 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DE10341945A1 (de) * | 2003-09-11 | 2005-04-21 | Bayer Cropscience Ag | Verwendung von fungiziden Mitteln zur Beizung von Saatgut |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10347440A1 (de) * | 2003-10-13 | 2005-05-04 | Bayer Cropscience Ag | Synergistische insektizide Mischungen |
| DE102004006075A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| DE102004021564A1 (de) * | 2003-11-14 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| DE10353281A1 (de) * | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
| DE10356550A1 (de) * | 2003-12-04 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| WO2005053406A1 (de) * | 2003-12-04 | 2005-06-16 | Bayer Cropscience Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden eigenschaften |
| BRPI0417315B1 (pt) * | 2003-12-04 | 2016-03-08 | Bayer Cropscience Ag | agente para controle de pragas animais, seu uso, processo para combater pragas animais, e processo para produção de agentes praguicidas. |
| CN101703067A (zh) * | 2003-12-12 | 2010-05-12 | 拜尔农作物科学股份公司 | 协同杀虫混合物 |
| WO2005081970A2 (en) | 2004-02-24 | 2005-09-09 | The Curators Of The University Of Missouri | Self-assembling cell aggregates and methods of making engineered tissue using the same |
| DE102004011006A1 (de) * | 2004-03-06 | 2005-09-22 | Bayer Cropscience Ag | Suspensionskonzentrate auf Ölbasis |
| DE102004011007A1 (de) * | 2004-03-06 | 2005-09-22 | Bayer Cropscience Ag | Suspensionskonzentrate auf Ölbasis |
| EP1606999A1 (de) * | 2004-06-18 | 2005-12-21 | Bayer CropScience AG | Saatgutbehandlungsmittel für Soja |
| GT200500179A (es) | 2004-07-01 | 2006-02-23 | Mezclas sinergistas de agentes de antranilamida para el control de plagas de invertebrados | |
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| DE102006014482A1 (de) * | 2006-03-29 | 2007-10-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
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| DE102006031978A1 (de) * | 2006-07-11 | 2008-01-17 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102006033154A1 (de) | 2006-07-18 | 2008-01-24 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
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| AU2009271223B2 (en) | 2008-06-24 | 2013-05-16 | The Curators Of The University Of Missouri | Self-assembling multicellular bodies and methods of producing a three-dimensional biological structure using the same |
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-
2003
- 2003-11-14 DE DE10353281A patent/DE10353281A1/de not_active Withdrawn
-
2004
- 2004-10-10 PT PT81602575T patent/PT1982594E/pt unknown
- 2004-10-10 AT AT04791082T patent/ATE425666T1/de active
- 2004-10-10 DE DE502004009184T patent/DE502004009184D1/de not_active Expired - Lifetime
- 2004-10-10 US US10/578,512 patent/US8299036B2/en active Active
- 2004-10-10 ES ES04791082T patent/ES2322364T3/es not_active Expired - Lifetime
- 2004-10-30 CN CN2004800400653A patent/CN1901798B/zh not_active Expired - Lifetime
- 2004-10-30 EP EP04791082.3A patent/EP1686858B8/de not_active Expired - Lifetime
- 2004-10-30 BR BRPI0416035-5A patent/BRPI0416035B1/pt active IP Right Grant
- 2004-10-30 KR KR1020067011360A patent/KR100858869B1/ko active IP Right Grant
- 2004-10-30 CN CN2010102775406A patent/CN101933518B/zh not_active Expired - Lifetime
- 2004-10-30 WO PCT/EP2004/012329 patent/WO2005048712A1/de active Application Filing
- 2004-10-30 JP JP2006538721A patent/JP4754495B2/ja not_active Expired - Lifetime
- 2004-10-30 ES ES08160257.5T patent/ES2477491T3/es not_active Expired - Lifetime
- 2004-10-30 AU AU2004290501A patent/AU2004290501C1/en active Active
- 2004-10-30 EP EP08160257.5A patent/EP1982594B1/de not_active Revoked
- 2004-10-30 PL PL04791082T patent/PL1686858T3/pl unknown
-
2006
- 2006-05-11 ZA ZA200603762A patent/ZA200603762B/en unknown
- 2006-05-11 IL IL175582A patent/IL175582A0/en unknown
-
2010
- 2010-03-09 US US12/719,935 patent/US8778895B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ATE425666T1 (de) | 2009-04-15 |
| WO2005048712A1 (de) | 2005-06-02 |
| AU2004290501A1 (en) | 2005-06-02 |
| CN1901798B (zh) | 2011-02-02 |
| IL175582A0 (en) | 2006-09-05 |
| EP1686858B1 (de) | 2009-03-18 |
| KR20060121159A (ko) | 2006-11-28 |
| KR100858869B1 (ko) | 2008-09-17 |
| US20080027114A1 (en) | 2008-01-31 |
| EP1686858B8 (de) | 2014-06-11 |
| JP4754495B2 (ja) | 2011-08-24 |
| AU2004290501C1 (en) | 2014-07-03 |
| BRPI0416035A (pt) | 2007-01-02 |
| AU2004290501B2 (en) | 2011-07-28 |
| JP2007510682A (ja) | 2007-04-26 |
| EP1982594B1 (de) | 2014-05-14 |
| EP1686858A1 (de) | 2006-08-09 |
| PT1982594E (pt) | 2014-07-16 |
| CN1901798A (zh) | 2007-01-24 |
| ES2477491T3 (es) | 2014-07-17 |
| DE10353281A1 (de) | 2005-06-16 |
| CN101933518A (zh) | 2011-01-05 |
| PL1686858T3 (pl) | 2009-08-31 |
| ES2322364T3 (es) | 2009-06-19 |
| EP1982594A1 (de) | 2008-10-22 |
| BRPI0416035B1 (pt) | 2014-12-30 |
| US20100168042A1 (en) | 2010-07-01 |
| US8299036B2 (en) | 2012-10-30 |
| CN101933518B (zh) | 2013-02-20 |
| DE502004009184D1 (de) | 2009-04-30 |
| US8778895B2 (en) | 2014-07-15 |
| WO2005048712A8 (de) | 2006-06-01 |
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