DD246915A5 - Schaedlingsbekaempfungsmittel, enthaltend aromatische alkanderivate - Google Patents

Schaedlingsbekaempfungsmittel, enthaltend aromatische alkanderivate Download PDF

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Publication number: DD246915A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; phenyl; alkoxy; aryl; alkenyloxy
Prior art date: 1985-02-14

Application number

DD86286987A

Other languages

German (de)

English (en)

Inventor

Helga Franke

Heinrich Franke

Hans-Rudolf Krueger

Hartmut Joppien

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-02-14

Filing date

1986-02-12

Publication date

1987-06-24

1986-02-12 Application filed by ��@��k�� filed Critical ��@��k��

1987-06-24 Publication of DD246915A5 publication Critical patent/DD246915A5/de

Links

-1 aromatic alkane Chemical class 0.000 claims abstract description 56
150000001875 compounds Chemical class 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
125000004996 haloaryloxy group Chemical group 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
241000238631 Hexapoda Species 0.000 claims abstract description 5
150000002431 hydrogen Chemical class 0.000 claims abstract description 5
239000000575 pesticide Substances 0.000 claims abstract description 5
241000238876 Acari Species 0.000 claims abstract description 4
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 3
241000607479 Yersinia pestis Species 0.000 claims abstract description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003435 aroyl group Chemical group 0.000 claims abstract description 3
125000001769 aryl amino group Chemical group 0.000 claims abstract description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 3
125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 3
125000006330 halo aroyl group Chemical group 0.000 claims abstract description 3
125000003106 haloaryl group Chemical group 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 6
239000000969 carrier Substances 0.000 claims description 5
UHLHWVKKDDXDLU-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-5,5-difluoro-4-methylpentyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C)(C(F)F)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 UHLHWVKKDDXDLU-UHFFFAOYSA-N 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims 2
125000003342 alkenyl group Chemical group 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 13
239000003795 chemical substances by application Substances 0.000 abstract description 7
125000005843 halogen group Chemical group 0.000 abstract description 4
125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 2
LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
238000002360 preparation method Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000004793 Polystyrene Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000011521 glass Substances 0.000 description 9
238000000034 method Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
230000000052 comparative effect Effects 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000462639 Epilachna varivestis Species 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
241000256250 Spodoptera littoralis Species 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
230000002147 killing effect Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000238657 Blattella germanica Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000257159 Musca domestica Species 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000013601 eggs Nutrition 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
OVANCIHPSBMNEN-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl)methylcarbamic acid Chemical compound C1=CC(CNC(O)=O)=C2OC(C)(C)CC2=C1 OVANCIHPSBMNEN-UHFFFAOYSA-N 0.000 description 2
IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 2
JACPTQMMZGZAOL-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCS(O)(=O)=O JACPTQMMZGZAOL-KHPPLWFESA-N 0.000 description 2
VBDDRWUBYCYFIN-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-5,5-difluoro-4-methylpent-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C)(C(F)F)C=CCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 VBDDRWUBYCYFIN-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241000239290 Araneae Species 0.000 description 2
240000007124 Brassica oleracea Species 0.000 description 2
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
241000736227 Lucilia sericata Species 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
241000500437 Plutella xylostella Species 0.000 description 2
241000238680 Rhipicephalus microplus Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
240000006677 Vicia faba Species 0.000 description 2
235000010749 Vicia faba Nutrition 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
PHHHFHPVARWSQY-UHFFFAOYSA-N 1-(4-methylpentyl)-3-phenoxybenzene Chemical compound CC(C)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 PHHHFHPVARWSQY-UHFFFAOYSA-N 0.000 description 1
AKBUGLSTCOYIIW-UHFFFAOYSA-N 1-[5,5-difluoro-4-[4-(2-fluoroethoxy)phenyl]-4-methylpentyl]-3-phenoxybenzene Chemical compound FC(C(CCCC1=CC(=CC=C1)OC1=CC=CC=C1)(C)C1=CC=C(C=C1)OCCF)F AKBUGLSTCOYIIW-UHFFFAOYSA-N 0.000 description 1
KLPZBDBSLKKZPO-UHFFFAOYSA-N 1-chloro-4-[1,1-difluoro-2-methyl-5-(3-phenoxyphenyl)pentan-2-yl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=CC=1OC1=CC=CC=C1 KLPZBDBSLKKZPO-UHFFFAOYSA-N 0.000 description 1
XFKWFMFDSJHRFD-UHFFFAOYSA-N 1-hexyl-3-phenoxybenzene Chemical compound CCCCCCC1=CC=CC(OC=2C=CC=CC=2)=C1 XFKWFMFDSJHRFD-UHFFFAOYSA-N 0.000 description 1
DYUYBNJDWMGMTJ-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3,3-difluoro-2-methylpropanal Chemical compound CCOC1=CC=C(C(C)(C=O)C(F)F)C=C1 DYUYBNJDWMGMTJ-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
BDMAQCJENZEGNY-UHFFFAOYSA-N 4-[1,1-difluoro-5-(4-fluoro-3-phenoxyphenyl)-2-methylpentan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 BDMAQCJENZEGNY-UHFFFAOYSA-N 0.000 description 1
AKFNFPJASUKEHX-UHFFFAOYSA-N 4-[4-(4-bromophenyl)-5,5-difluoro-4-methylpentyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(Br)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 AKFNFPJASUKEHX-UHFFFAOYSA-N 0.000 description 1
UQHXHTGMFGNVRC-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-5,5-difluoro-4-methylpentyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 UQHXHTGMFGNVRC-UHFFFAOYSA-N 0.000 description 1
CEMNMRJMRYYULB-UHFFFAOYSA-N 4-[4-[4-(difluoromethoxy)phenyl]-5,5-difluoro-4-methylpentyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(OC(F)F)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 CEMNMRJMRYYULB-UHFFFAOYSA-N 0.000 description 1
WCDIPELQSRXHJZ-UHFFFAOYSA-N 4-[5,5-difluoro-4-(4-methoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OC)=CC=C1C(C)(C(F)F)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 WCDIPELQSRXHJZ-UHFFFAOYSA-N 0.000 description 1
DPXWCUQGUOYBFD-UHFFFAOYSA-N 4-[5,5-difluoro-4-[4-(2-fluoroethoxy)phenyl]-4-methylpentyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(OCCF)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 DPXWCUQGUOYBFD-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
241001300479 Macroptilium Species 0.000 description 1
241001494479 Pecora Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
235000002098 Vicia faba var. major Nutrition 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
FJFYTDBMUXVUSZ-UHFFFAOYSA-N [4-[1,1-difluoro-2-methyl-5-(3-phenoxyphenyl)pentan-2-yl]phenyl] trifluoromethanesulfonate Chemical compound C=1C=C(OS(=O)(=O)C(F)(F)F)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=CC=1OC1=CC=CC=C1 FJFYTDBMUXVUSZ-UHFFFAOYSA-N 0.000 description 1
IWZKAXFUMHRWOX-UHFFFAOYSA-N [4-[1,1-difluoro-5-(4-fluoro-3-phenoxyphenyl)-2-methylpentan-2-yl]phenyl] trifluoromethanesulfonate Chemical compound C=1C=C(OS(=O)(=O)C(F)(F)F)C=CC=1C(C)(C(F)F)CCCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 IWZKAXFUMHRWOX-UHFFFAOYSA-N 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 1
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229920005551 calcium lignosulfonate Polymers 0.000 description 1
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
VJOCYCQXNTWNGC-UHFFFAOYSA-L calcium;benzenesulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1 VJOCYCQXNTWNGC-UHFFFAOYSA-L 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
244000013123 dwarf bean Species 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000006485 halo alkoxy phenyl group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000006028 limestone Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940058401 polytetrafluoroethylene Drugs 0.000 description 1
239000004810 polytetrafluoroethylene Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- 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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)

DD86286987A 1985-02-14 1986-02-12 Schaedlingsbekaempfungsmittel, enthaltend aromatische alkanderivate DD246915A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853505370 DE3505370A1 (de)	1985-02-14	1985-02-14	Aromatische alkanderivate, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
DD246915A5 true DD246915A5 (de)	1987-06-24

Family

ID=6262695

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86286987A DD246915A5 (de)	1985-02-14	1986-02-12	Schaedlingsbekaempfungsmittel, enthaltend aromatische alkanderivate

Country Status (16)

Country	Link
US (1)	US4743622A (da)
EP (1)	EP0191723A1 (da)
JP (1)	JPS61189238A (da)
KR (1)	KR860006428A (da)
CN (1)	CN86100948A (da)
AU (1)	AU5339686A (da)
BR (1)	BR8600619A (da)
DD (1)	DD246915A5 (da)
DE (1)	DE3505370A1 (da)
DK (1)	DK63786A (da)
ES (1)	ES8701709A1 (da)
FI (1)	FI860399A7 (da)
HU (1)	HUT41211A (da)
PH (1)	PH22364A (da)
SU (1)	SU1470172A3 (da)
ZA (1)	ZA861127B (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3602169A1 (de) *	1986-01-22	1987-07-23	Schering Ag	Neue alkan- und alkoxyalkanderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel
GB8605281D0 (en) *	1986-03-04	1986-04-09	Ici Plc	Diphenyl ether derivatives
GB2187452A (en) *	1986-03-04	1987-09-09	Ici Plc	Insecticidal fluoroalkyl benzene derivatives
DE3628300A1 (de) *	1986-08-21	1988-02-25	Schering Ag	Alkan- und alkoxyalkan-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel
GB8703653D0 (en) *	1987-02-17	1987-03-25	Ici Plc	Preparation of insecticidally active compounds
GB8822792D0 (en) *	1988-09-28	1988-11-02	Ici Plc	Insecticidal compounds
GB9408605D0 (en) *	1994-04-29	1994-06-22	British Tech Group	Pesticidal fluoroolefins
GEP20022795B (en) *	1997-06-19	2002-09-25	American Cyanamid Co	Process and Intermediate Compounds for Preparation of Pesticidal Fluoroolefin Compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4397864A (en) *	1980-05-02	1983-08-09	Mitsuitoatsu Chemicals Inc.	2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives
JPS58201737A (ja) *	1982-05-18	1983-11-24	Mitsui Toatsu Chem Inc	新規芳香族アルカン誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤

1985
- 1985-02-14 DE DE19853505370 patent/DE3505370A1/de not_active Withdrawn
1986
- 1986-01-28 FI FI860399A patent/FI860399A7/fi not_active Application Discontinuation
- 1986-02-05 PH PH33395A patent/PH22364A/en unknown
- 1986-02-10 DK DK63786A patent/DK63786A/da not_active Application Discontinuation
- 1986-02-10 SU SU864019299A patent/SU1470172A3/ru active
- 1986-02-11 US US06/828,289 patent/US4743622A/en not_active Expired - Fee Related
- 1986-02-11 AU AU53396/86A patent/AU5339686A/en not_active Abandoned
- 1986-02-12 DD DD86286987A patent/DD246915A5/de unknown
- 1986-02-13 BR BR8600619A patent/BR8600619A/pt unknown
- 1986-02-13 KR KR1019860000998A patent/KR860006428A/ko not_active Withdrawn
- 1986-02-13 EP EP86730022A patent/EP0191723A1/de not_active Withdrawn
- 1986-02-13 ES ES551957A patent/ES8701709A1/es not_active Expired
- 1986-02-13 HU HU86625A patent/HUT41211A/hu unknown
- 1986-02-14 JP JP61029106A patent/JPS61189238A/ja active Pending
- 1986-02-14 CN CN198686100948A patent/CN86100948A/zh active Pending
- 1986-02-14 ZA ZA861127A patent/ZA861127B/xx unknown

Also Published As

Publication number	Publication date
ES8701709A1 (es)	1987-01-01
BR8600619A (pt)	1986-10-29
HUT41211A (en)	1987-04-28
DE3505370A1 (de)	1986-08-14
US4743622A (en)	1988-05-10
ES551957A0 (es)	1987-01-01
SU1470172A3 (ru)	1989-03-30
KR860006428A (ko)	1986-09-11
FI860399A0 (fi)	1986-01-28
DK63786D0 (da)	1986-02-10
PH22364A (en)	1988-08-12
EP0191723A1 (de)	1986-08-20
AU5339686A (en)	1986-08-21
FI860399A7 (fi)	1986-08-15
ZA861127B (en)	1986-09-24
JPS61189238A (ja)	1986-08-22
CN86100948A (zh)	1986-09-03
DK63786A (da)	1986-08-15

Publication	Publication Date	Title
DE2461027A1 (de)	1975-11-06	Derivate von 2-cyclohexen-1-on, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DD282608A5 (de)	1990-09-19	Insektizide und akaridizid wirkende zusammensetzung
EP0179018A1 (de)	1986-04-23	Substituierte Benzylether, Schädlingsbekämpfungsmittel enthaltend diese Verbindungen sowie Verfahren zu ihrer Herstellung
DE3602169A1 (de)	1987-07-23	Neue alkan- und alkoxyalkanderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel
DE3604781A1 (de)	1987-08-27	Neue silane, verfahren zu ihrer herstellung und diese verbindungen enthaltende einsektizide mittel
CH646160A5 (de)	1984-11-15	Heterocyclisch substituierte phenylether, diese enthaltende herbizide mittel, sowie verfahren zu deren herstellung.
EP0191723A1 (de)	1986-08-20	Aromatische Alkanderivate, Schädlingsbekämpfungsmittel enthaltend diese Vebindungen sowie Verfahren zu ihrer Herstellung
DE2149312B2 (de)	1979-06-21	Thiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Nematicide und Bodeninsektizide
EP0198791A1 (de)	1986-10-22	Difluorcyclopropanderivate, Verfahren zu ihrer Herstellung sowie Schädlingsbekämpfungsmittel enthaltend diese Verbindungen
CH616654A5 (da)	1980-04-15
EP0136451A2 (de)	1985-04-10	Arylmethylätherderivate, Schädlingsbekämpfungsmittel enthaltend diese Verbindungen sowie Verfahren zu ihrer Herstellung
DE2647368A1 (de)	1977-05-05	Alpha-(1-pyrrolyl)-carbonsaeure-3- phenoxy-benzylester, verfahren zu ihrer herstellung und ihre verwendung
DE2914300C2 (da)	1989-02-09
DD262992A5 (de)	1988-12-21	Nematizide und insektizide zusammensetzung
CH633675A5 (de)	1982-12-31	Biocid wirksames mittel enthaltend ein arylhydrazonderivat.
DE1813194A1 (de)	1969-08-14	Trichlorthiophen-2-carbonsaeureamide
DD253753A5 (de)	1988-02-03	Schaedlingsbekaempfungsmittel
DD149012A5 (de)	1981-06-24	Bodeninsektizide mittel
DE1301175B (de)	1969-08-14	Totalherbizid mit insektizider Wirkung
DE3227894A1 (de)	1983-02-17	Herbizide phenoxybenzoesaeure-verbindungen
DE3628300A1 (de)	1988-02-25	Alkan- und alkoxyalkan-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel
DE3715872A1 (de)	1988-11-24	Organische zinnverbindungen, ihre herstellung und ihre verwendung als insektizide und akarizide mittel
DE1810581C3 (de)	1977-12-29	N-Acyl-p-dialkylamino-phenylhydrazone, Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von phytopathogene Pilzen
DE3225520A1 (de)	1983-02-03	Triazole und ihre verwendung zur bekaempfung von schaedlingen
DE3522322A1 (de)	1987-01-02	Cyclopentenderivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel