ZA200210353B - Combinations of active ingredients, which exhibit insecticidal and acaricidal properties. - Google Patents
Combinations of active ingredients, which exhibit insecticidal and acaricidal properties. Download PDFInfo
- Publication number
- ZA200210353B ZA200210353B ZA200210353A ZA200210353A ZA200210353B ZA 200210353 B ZA200210353 B ZA 200210353B ZA 200210353 A ZA200210353 A ZA 200210353A ZA 200210353 A ZA200210353 A ZA 200210353A ZA 200210353 B ZA200210353 B ZA 200210353B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- optionally
- substituted
- methyl
- alkoxy
- Prior art date
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- 230000000895 acaricidal effect Effects 0.000 title claims description 6
- 230000000749 insecticidal effect Effects 0.000 title claims description 6
- 239000004480 active ingredient Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 239000005864 Sulphur Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 claims description 2
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 2
- 239000005652 Acrinathrin Substances 0.000 claims description 2
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims description 2
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims description 2
- 239000005946 Cypermethrin Substances 0.000 claims description 2
- 239000005892 Deltamethrin Substances 0.000 claims description 2
- 239000005895 Esfenvalerate Substances 0.000 claims description 2
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 claims description 2
- KAATUXNTWXVJKI-QPIRBTGLSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-QPIRBTGLSA-N 0.000 claims description 2
- YLFSVIMMRPNPFK-WEQBUNFVSA-N acrinathrin Chemical compound CC1(C)[C@@H](\C=C/C(=O)OC(C(F)(F)F)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YLFSVIMMRPNPFK-WEQBUNFVSA-N 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-UHFFFAOYSA-N 0.000 claims description 2
- 229960001591 cyfluthrin Drugs 0.000 claims description 2
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 2
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 2
- 229960005424 cypermethrin Drugs 0.000 claims description 2
- 229960002483 decamethrin Drugs 0.000 claims description 2
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 claims description 2
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 claims description 2
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 claims description 2
- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 claims description 2
- WIFXJBMOTMKRMM-UHFFFAOYSA-N halfenprox Chemical compound C=1C=C(OC(F)(F)Br)C=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 WIFXJBMOTMKRMM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229960000490 permethrin Drugs 0.000 claims description 2
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 239000005936 tau-Fluvalinate Substances 0.000 claims description 2
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 claims description 2
- 239000005943 zeta-Cypermethrin Substances 0.000 claims description 2
- -1 cyano- Chemical class 0.000 claims 31
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 239000005874 Bifenthrin Substances 0.000 claims 1
- 239000005896 Etofenprox Substances 0.000 claims 1
- 239000004606 Fillers/Extenders Substances 0.000 claims 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims 1
- 229950005085 etofenprox Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims 1
- 229940108410 resmethrin Drugs 0.000 claims 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 claims 1
- 241001484259 Lacuna Species 0.000 description 10
- 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 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 1
- 150000008047 benzoylureas Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
Landscapes
- 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)
Description
Active compound combinations haying insecticidal and acaricidal properties )
The present invention relates to novel active compound combinations comprising known cyclic ketoenols on the one hand and other known insecticidally active- compounds on the other hand, which combinations are highly suitable for controlling animal pests such as insects and undesired acarids.
It is already known that certain cyclic ketoenols have herbicidal, insecticidal and acaricidal properties. The activity of these substances is good; however, at low application rates it is sometimes unsatisfactory. ’
Bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A-415211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077) with herbicidal, insecticidal or acaricidal action are known.
Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073) and 1H-arylpyrrolidine-dione derivatives (EP-A-456 063, EP-A-521334, EP-A- 596 298, EP-A-613 884, [EP-A-613885, WO 94/01 997, WO 95/26 954,
WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535,
WO 97/02 243, WO 97/36 868, WO 97/ 43 275, WO 98/05 638, WO 98/06 721,
WO 98/25 928, WO 99/16 748, WO 99/24 437, WO 99/43 649, WO 99/48 869 and
WO 99/55 673).
Furthermore, it is already known that numerous heterocycles, organotin compounds, benzoylureas and pyrethroids have insecticidal and acaricidal properties (cf.
WO 93/22 297, WO 93/10 083, DE-A-2 641 343, EP-A-347 488, EP-A-210 487,
US 3,364,177 and EP-A-234 045). However, the activity of these substances is not always satisfactory.
It has now been found that mixtures of compounds of the formula @
G—o X
Y
X :
Z
5" M
D oW ) in which
X represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or cyano,
W. Y and Z independently of one another each represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or cyano, :
A represents hydrogen, in each case optionally halogen-substituted alkyl, alkoxyalkyl, saturated, optionally substituted cycloalkyl, in which optionally at least one ring atom is replaced by a heteroatom,
B represents hydrogen or alkyl,
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom,
D represents hydrogen or an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkoxyalkyl, saturated cycloalkyl in which optionally one or more ring members are replaced by heteroatoms,
A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which is unsubstituted or substituted in the A,D moiety and optionally contains at least one heteroatom,
G represents hydrogen (a) or represents one of the groups x i § .R? SO,—R?® —P.
Fy owe OTT Te
R® :
E pu / ] fy or N (f) L wv (9) in which
E represents a metal ion or an ammonium ion, .
L represents oxygen or sulphur,
M represents oxygen or sulphur,
Rl represents in each case optionally halogen-substituted alkyl, alkenyl, oo alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by at : least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R2 represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl, rR? represents optionally halogen-substituted alkyl or optionally substituted phenyl,
R4 and RS independently of one another each represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio and
RO and R7 independently of one another each represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represents optionally substituted phenyl, represent optionally substituted benzyl or together with the N atom to which. they are attached represent an optionally substituted ring which is optionally interrupted by oxygen or sulphur and pyrethroids, preferably 1. acrinathrin
CF.
Ba
CF; le) — 0)
H,C 0 * cH, © CN known from EP-A-048 186 and/or 2. alpha-cypermethrin [ - § A
NS 0
Cl oO
Oo CN ® known from EP-A-067 461 and/or
3. betacyfluthrin
H,C CH,
Ci : 0) =
Ci } . ©
F known from EP-A-206 14¢ and/or 4, cyhalothrin :
Fy .
Cc 0) 0)
H.C : 3 CH, O ¢n known [lacuna] DE-A-2 802 962 and/or : 10 5. cypermethrin
Cl cr 0)
Oo
H.C 8 CH, O ¢N known [lacuna] DE-A-2 326 077 and/or
6. deltamethrin ’
Br H.C CH, 0 CN )
BY. a known [lacuna] DE-A-2 326 077 and/or 7. esfenvalerate 0 : 1S 0) 0 CN
HC CH, known from DE-A-2 737 297 and/or
8. ethofenprox : oC
IOS ASAS .
HC CH, known [lacuna] DE-A-3 117 510 and/or 9. fenpropathrin .
H,C\ CH,
H,C o IL. 0
Hy, © ©
CN known [lacuna] DE-A-2 231 312 and/or 10. fenvalerate
Cl o CN
BR
H,C CH, known [lacuna] DE-A-2 335 347 and/or
11. flucythrinate o X
FHC” LL CN o - “UO
H,C CH, known [lacuna] DE-A-2 757 066 and/or - 12. lambda-cyhalothrin
H,C CH,
Cl 0]
FC h 0 CN : 0] known [lacuna] EP-A-106 469 and/or
13. permethrin
H,C CH, [ LI 0
Cl X known [lacuna] DE-A-2 326 077 and/or : 14. taufluvalinate .
Cl 0 CN
H jones x ° 1 ®
F.C H.C CH, known [lacuna] EP-A-038 617 and/or 15. tralomethrin
H.C CH,
Br,C 0) JQ oOo. known [lacuna] DE-A-2 742 546 . and/or
16. zeta-cypermethrin
H,C CH,
Cl o i
AA A known [lacuna] EP-A-026 542 and/or 5 . 17. cyfluthrin
H.C CH, F
Cl 0) or XX 0
O H CN ) known from DE-A-27 09 264 and/or 18. bifenthrin
H,C CH,
Cl
NU 0 0 CH, known from EP-A-049 977 and/or
S11 - 19. cycloprothrin
OCH,CH,
Cl
NEY ~
P
© 0 1] dn ) known from DE-A-2653189 . 5 and/or 20. eflusilanate
F.
Ts
H 7 | :
Jor 0 known from DE-A-36 04 781 } 10 and/or 21. fubfenprox
H,G CH, . 0
F
Br—L
F 0) known from DE-A-37 08 231 and/or
Claims (8)
1. Composition, comprising mixtures of compounds of the formula @ G—o X A Y X Z B N Mm op oY in which X represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or cyano, W, Y and Z independently of one another each represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or cyano, A represents hydrogen, in each case optionally halogen-substituted alkyl, alkoxyalkyl, saturated, optionally substituted cycloalkyl, in which optionally at least one ring atom is replaced by a heteroatom, B represents hydrogen or alkyl, A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom, : D represents hydrogen or an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkoxyalkyl, saturated cycloalkyl in which optionally one or more ring members are replaced : by heteroatoms,
A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which is unsubstituted or substituted in the A,D moiety and optionally contains at least one heteroatom, G represents hydrogen (a) or represents one of the groups 0 L Rr? .R? SO—R’ —P.
PN 0), A, (¢), —~ 2 (d), / RS ©). R® L eo E fy) or >— N (f) \ 7 (9) in which . E represents a metal ion or an ammonium ion, L represents oxygen or sulphur, M represents oxygen or sulphur,
) Rl represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R2 represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl, R3 represents optionally halogen-substituted alkyl or optionally substituted phenyl,
- 48 - oo R4 and RS independently of one another each represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio and RO and R7 independently of one another each represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represents optionally substituted phenyl, represent optionally substituted benzyl or together with the N atom to which they are attached represent an optionally substituted ring which is optionally interrupted by oxygen or sulphur and at least one of the compounds below acrinathrin : alpha-cypermethrin betacyfluthrin cyhalothrin cypermethrin deltamethrin esfenvalerate etofenprox fenpropathrin fenvalerate flucythrinate lambda-cyhalothrin permethrin tau-fluvalinate tralomethrin zeta-cypermethrin cyfluthrin bifenthrin cycloprothrin eflusilanate fubfenprox pyrethrin . resmethrin.
2. Composition according to Claim 1, comprising compounds of the formula (I) in which A represents hydrogen, C,-Cy-alkyl, C 1-C4-alkoxy, chlorine, bromine or fluorine, X represents Cy-C4-alkyl, C;-C4-alkoxy, C,-Cy4-halogenoalkyl, fluorine, chlorine or bromine, Y and Z independently of one another each represent hydrogen, C;-Cy-alkyl, halogen, C;-Cy4-alkoxy or C;-C4-halogenoalkyl, A represents hydrogen or in each case optionally halogen-substituted Ci- Cs-alkyl or C3-Cg-cycloalkyl, B represents hydrogen, methyl or ethyl, A,B and the carbon atom to which they are attached represent saturated C3-Cy-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which is optionally mono- or disubstituted by C,-Cy-alkyl, trifluoromethyl or C, -Cs-alkoxy, D represents hydrogen, in each case optionally fluorine- or chlorine- substituted C,-Cg-alkyl, C3-C;-alkenyl or C3-Cg-cycloalkyl,
A and D together represent in each case optionally methyl-substituted C;-Cy- alkanediyl in which optionally one methylene group is replaced by sulphur, G represents hydrogen (a) or represents one of the groups 0 L R* R? O- 3 SE p J R! ®), MN M id ©), _S 2 | R (d), Vi ~ R® (e), R® : . ® Ny 4 ‘ E or N L gf ©@) : in which :
E represents a metal ion or an ammonium ion, L represents oxygen or sulphur and M represents oxygen or sulphur, R! represents in each case optionally halogen-substituted C,-Cjo-alkyl, C,-C 10-alkenyl , C 1 -Cs-alkoxy-C 1 -Cs-alkyl R C 1 -Cy-alkylthio-C 1 -Cs- alkyl or optionally fluorine-, chlorine-, Cy-Cy-alkyl or C,-C»-alkoxy- substituted C3-Cg-cycloalkyl, represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C;- Cs-alkyl-, C;-Cs-alkoxy-, trifluoromethyl- or trifluoromethoxy- substituted phenyl,
represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl, R? represents in each case optionally fluorine- or chlorine-substituted C,-Cip-alkyl, C,-Cjp-alkenyl, C,-Cy-alkoxy-C,-Cy-alkyl,
represents optionally methyl- or methoxy-substituted Cs-Ce-cycloalkyl or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C;-Cy-alkyl, C;-C4-alkoxy, triflouromethyl- or ) trifluoromethoxy-substituted phenyl or benzyl, rR? represents optionally fluorine-substituted C;-Cs-alkyl or represents optionally fluorine-, chlorine-, bromine-, C,-Cs-alkyl, C;-C4-alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro-substituted phenyl, R* represents in each case optionally fluorine- or chlorine-substituted Ci-Cs-alkyl, C;-Cy-alkoxy, C,-Cy-alkylamino, C,-Cy-alkylthio or represents in each case optionally fluorine-, chlorine-, bromine-, : nitro-, cyano-, C;-Cy-alkoxy, trifluoromethoxy, C-Cy-alkylthio, C;- Cs-halogenoalkylthio, C;-C;-alkyl or trifluoromethyl-substituted phenyl, phenoxy or phenylthio, R® represents C;-Cy-alkoxy or C;-Cy-thioalkyl, R® represents C,-Cg-alkyl, C3-Cs-cycloalkyl, C;-Cs-alkoxy, C;-Ce- alkenyl, C,-C4-alkoxy-C;-C;-alkyl, R’ represents C;-Cg-alkyl, C3-Cg-alkenyl or C,-Cy4-alkoxy-C,-Cs-alkyl, R® and R together represent an optionally methyl- or ethyl-substituted C;-Cg- alkylene radical in which optionally one carbon atom is replaced by oxygen or sulphur.
3. Composition according to Claim 1, comprising compounds of the formula (I) in which
Ww represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy, X represents chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy or trifluoromethyl, :
Y and Z independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, trifluoromethyl or methoxy, A represents methyl, ethyl, propyl, i-propyl, butyl, i-butyl, sec-butyl, tert- butyl, cyclopropyl, cyclopentyl or cyclohexyl, B represents hydrogen, methyl or ethyl, A, B and the carbon atom to which they are attached represent saturated Ce-cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, : methoxy, ethoxy, propoxy or butoxy, D represents hydrogen, represents methyl, ethyl, propyl, i-propyl, butyl, i-butyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl, A and D together represent optionally methyl-substituted C;-Cs-alkanediyl, G represents hydrogen (a) or represents one of the groups 0 fo) JR 2 JM 1 -R or pus N R™ (), A mo © of TW © in which M represents oxygen or sulphur,
R! represents C;-Cg-alkyl, C;-Cs-alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl, represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, methoxy-, trifluoromethyl- or trifluoromethoxy- substituted phenyl, represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl, ’ R? represents C,-Cg-alkyl, C,-Cy-alkenyl, methoxyethyl, ethoxyethyl or represents phenyl or benzyl, R® and R’ independently of one another represent methyl or ethyl or together represent a Cs-alkylene radical in which the C;-methylene group is replaced by oxygen.
4. Composition according to Claim 1, comprising compounds of the formula q)) in which Ww represents hydrogen or methyl, X represents chlorine, bromine or methyl, i Y and Z independently of one another each represent hydrogen, chlorine, bromine or methyl, A, B and the carbon atom to which they are attached represent saturated Ce-cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, methoxy, ethoxy, propoxy or butoxy,
D represents hydrogen, G represents hydrogen (a) or represents one of the groups SU ¢ _ N .R? or Sn ; (9) R (b), M (c) ’ le} “rR in which . M represents oxygen or sulphur, R! represents C,-Cs-alkyl, C,-C4-alkenyl, methoxymethyl, ethoxymethyl, ethylmethylthio, cyclopropyl, cyclopentyl, cyclohexyl or represents optionally fluorine-, chlorine-, bromine-, methyl-, methoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro- substituted phenyl, represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl, R? represents C;-Cg-alkyl, C;-Cy-alkenyl, methoxyethyl, ethoxyethyl, phenyl or benzyl, R® and R’ independently of one another each represent methyl, ethyl or together represent a Cs-alkylene radical in which the Cs-methylene group is replaced by oxygen.
5. Composition according to Claim 1, comprising compounds of the formula 4)
H 0 X 3 N Y R Z 4 Zz c~° Ww - in which W,X,Y,Z, R and G are each as defined in the table. Ca CE CO CO CO H CHj 4-CHj 5-CHj3 OCH3 /\ CO—N 0 >CH H CH; 5-CHj3 H OCyHs /\ CO—N 0
5
6. Use of mixtures as defined in Claim 1, 2, 3, 4 or 5 for controlling animal pests.
7. Method for controlling animal pests, characterized in that mixtures as defined in Claim 1, 2, 3, 4 or 5 are allowed to act on animal pests and/or their habitat.
8. Process for preparing insecticidal and acaricidal compositions, characterized in that mixtures as defined in Claim 1, 2, 3, 4 or 5 are mixed with extenders and/or surfactants.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10031765 | 2000-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200210353B true ZA200210353B (en) | 2004-01-26 |
Family
ID=7647262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200210353A ZA200210353B (en) | 2000-06-29 | 2002-12-20 | Combinations of active ingredients, which exhibit insecticidal and acaricidal properties. |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE10036896A1 (en) |
| PE (1) | PE20020138A1 (en) |
| RU (1) | RU2291617C2 (en) |
| TW (1) | TWI291855B (en) |
| ZA (1) | ZA200210353B (en) |
-
2000
- 2000-07-28 DE DE10036896A patent/DE10036896A1/en not_active Withdrawn
-
2001
- 2001-06-18 RU RU2003102605/04A patent/RU2291617C2/en not_active IP Right Cessation
- 2001-06-26 TW TW090115342A patent/TWI291855B/en not_active IP Right Cessation
- 2001-06-28 PE PE2001000640A patent/PE20020138A1/en active IP Right Grant
-
2002
- 2002-12-20 ZA ZA200210353A patent/ZA200210353B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2291617C2 (en) | 2007-01-20 |
| DE10036896A1 (en) | 2002-01-10 |
| TWI291855B (en) | 2008-01-01 |
| PE20020138A1 (en) | 2002-04-27 |
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