DE1297400B - Schaedlingsbekaempfungsmittel - Google Patents
SchaedlingsbekaempfungsmittelInfo
- Publication number
- DE1297400B DE1297400B DES96570A DES0096570A DE1297400B DE 1297400 B DE1297400 B DE 1297400B DE S96570 A DES96570 A DE S96570A DE S0096570 A DES0096570 A DE S0096570A DE 1297400 B DE1297400 B DE 1297400B
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethyl
- carboxylic acid
- ester
- trichlorobenzimidazole
- benzimidazole
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 241000607479 Yersinia pestis Species 0.000 title description 2
- 239000000460 chlorine Substances 0.000 claims description 5
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001556 benzimidazoles Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 13
- 239000002917 insecticide Substances 0.000 description 13
- -1 cycloalkyl radical Chemical class 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 241000500437 Plutella xylostella Species 0.000 description 7
- 241001454293 Tetranychus urticae Species 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- JQULGDSPPLTYIF-UHFFFAOYSA-N 4,5,6-trichloro-2-(trifluoromethyl)benzimidazole-1-carboxylic acid Chemical compound ClC1=C(C(=CC=2N(C(=NC21)C(F)(F)F)C(=O)O)Cl)Cl JQULGDSPPLTYIF-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- MJABXZWILYUAEB-UHFFFAOYSA-N benzimidazole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)C=NC2=C1 MJABXZWILYUAEB-UHFFFAOYSA-N 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 230000003151 ovacidal effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000194 ovacidal Toxicity 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BXCSXZJKEJQDKS-UHFFFAOYSA-N 4,5,6-trichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound ClC1=C(Cl)C=C2NC(C(F)(F)F)=NC2=C1Cl BXCSXZJKEJQDKS-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 108700031361 Brachyury Proteins 0.000 description 1
- 240000008100 Brassica rapa Species 0.000 description 1
- 235000011292 Brassica rapa Nutrition 0.000 description 1
- NVQQVRAFZNRHES-UHFFFAOYSA-N C(CC(C)C)OC(=O)N1C(=NC2=C1C=C(C(=C2Cl)Cl)Cl)C(F)(F)F Chemical compound C(CC(C)C)OC(=O)N1C(=NC2=C1C=C(C(=C2Cl)Cl)Cl)C(F)(F)F NVQQVRAFZNRHES-UHFFFAOYSA-N 0.000 description 1
- UQIFYGHOQSRKBM-UHFFFAOYSA-N C1=NC2=CC=CC=C2N1C(=O)OC1=CC=CC=C1 Chemical compound C1=NC2=CC=CC=C2N1C(=O)OC1=CC=CC=C1 UQIFYGHOQSRKBM-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 241000238631 Hexapoda Species 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
- 241000257226 Muscidae Species 0.000 description 1
- 241000118205 Ovicides Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- KEAQRENIDURQFY-UHFFFAOYSA-N benzyl benzimidazole-1-carboxylate Chemical compound C1=NC2=CC=CC=C2N1C(=O)OCC1=CC=CC=C1 KEAQRENIDURQFY-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003181 biological factor Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000007681 cardiovascular toxicity Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MGUJLJPUQIWMFE-UHFFFAOYSA-N methyl 4,5,6-trichloro-2-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound ClC1=C(Cl)C=C2N(C(=O)OC)C(C(F)(F)F)=NC2=C1Cl MGUJLJPUQIWMFE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- CCTJHZUUXXGMAM-UHFFFAOYSA-N propan-2-yl 4,5,6-trichloro-2-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C(=O)(OC(C)C)N1C(=NC2=C1C=C(C(=C2Cl)Cl)Cl)C(F)(F)F CCTJHZUUXXGMAM-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940035339 tri-chlor Drugs 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES96570A DE1297400B (de) | 1965-04-15 | 1965-04-15 | Schaedlingsbekaempfungsmittel |
| DE19651620264 DE1620264A1 (de) | 1965-04-15 | 1965-04-15 | Verfahren zur Herstellung substituierter Benzimidazol-I-carbonsaeureester |
| FR57393A FR1484718A (fr) | 1965-04-15 | 1966-04-03 | Esters de l'acide benzimidazole-1-(thio) carboxylique substitués |
| US542204A US3884933A (en) | 1965-04-15 | 1966-04-13 | Certain substituted benzimidazoles |
| GB16182/66A GB1114943A (en) | 1965-04-15 | 1966-04-13 | Substituted benzimidazole-1-carboxylic acid esters |
| DK189466AA DK129316B (da) | 1965-04-15 | 1966-04-13 | Anvendelse af substituerede benzimidazol-1-carboxylsyreestere til bekæmpelse af arachnidae eller deres æg. |
| DE19661567132 DE1567132A1 (de) | 1965-04-15 | 1966-04-13 | Herbizides Mittel |
| IL25573A IL25573A (en) | 1965-04-15 | 1966-04-13 | Substituted benzimidazole-1-carboxylic and thiocarboxylic acid esters,their preparation and use |
| CH535966A CH480794A (de) | 1965-04-15 | 1966-04-13 | Pestizides Mittel mit einem substituierten Benzimidazol-1-carbonsäureester |
| BR178696/66A BR6678696D0 (pt) | 1965-04-15 | 1966-04-13 | Composicoes pesticidas compreendendo um ester de acido benzimidazol-substituido-1-(10) carboxilico como ingrediente ativo e processo para preparar tal ester |
| NL6605140A NL6605140A (en:Method) | 1965-04-15 | 1966-04-15 | |
| BE679607D BE679607A (en:Method) | 1965-04-15 | 1966-04-15 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44824365A | 1965-04-15 | 1965-04-15 | |
| DES96570A DE1297400B (de) | 1965-04-15 | 1965-04-15 | Schaedlingsbekaempfungsmittel |
| DES0096569 | 1965-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1297400B true DE1297400B (de) | 1969-06-12 |
Family
ID=27212933
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES96570A Pending DE1297400B (de) | 1965-04-15 | 1965-04-15 | Schaedlingsbekaempfungsmittel |
| DE19651620264 Pending DE1620264A1 (de) | 1965-04-15 | 1965-04-15 | Verfahren zur Herstellung substituierter Benzimidazol-I-carbonsaeureester |
| DE19661567132 Pending DE1567132A1 (de) | 1965-04-15 | 1966-04-13 | Herbizides Mittel |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651620264 Pending DE1620264A1 (de) | 1965-04-15 | 1965-04-15 | Verfahren zur Herstellung substituierter Benzimidazol-I-carbonsaeureester |
| DE19661567132 Pending DE1567132A1 (de) | 1965-04-15 | 1966-04-13 | Herbizides Mittel |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3884933A (en:Method) |
| BE (1) | BE679607A (en:Method) |
| BR (1) | BR6678696D0 (en:Method) |
| CH (1) | CH480794A (en:Method) |
| DE (3) | DE1297400B (en:Method) |
| DK (1) | DK129316B (en:Method) |
| GB (1) | GB1114943A (en:Method) |
| IL (1) | IL25573A (en:Method) |
| NL (1) | NL6605140A (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0844998B1 (de) * | 1995-08-10 | 2003-04-23 | Bayer CropScience AG | Halogenbenzimidazole und ihre verwendung als mikrobizide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2933502A (en) * | 1958-02-12 | 1960-04-19 | Du Pont | Benzimidazolone derivatives |
| US2933504A (en) * | 1959-08-10 | 1960-04-19 | Du Pont | Derivatives of polyalkoxycarbonyl imine |
-
1965
- 1965-04-15 DE DES96570A patent/DE1297400B/de active Pending
- 1965-04-15 DE DE19651620264 patent/DE1620264A1/de active Pending
-
1966
- 1966-04-13 BR BR178696/66A patent/BR6678696D0/pt unknown
- 1966-04-13 DK DK189466AA patent/DK129316B/da unknown
- 1966-04-13 DE DE19661567132 patent/DE1567132A1/de active Pending
- 1966-04-13 US US542204A patent/US3884933A/en not_active Expired - Lifetime
- 1966-04-13 GB GB16182/66A patent/GB1114943A/en not_active Expired
- 1966-04-13 CH CH535966A patent/CH480794A/de not_active IP Right Cessation
- 1966-04-13 IL IL25573A patent/IL25573A/en unknown
- 1966-04-15 BE BE679607D patent/BE679607A/xx unknown
- 1966-04-15 NL NL6605140A patent/NL6605140A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6605140A (en:Method) | 1966-10-17 |
| CH480794A (de) | 1969-11-15 |
| IL25573A (en) | 1970-04-20 |
| DK129316B (da) | 1974-09-30 |
| GB1114943A (en) | 1968-05-22 |
| DK129316C (en:Method) | 1975-04-14 |
| BR6678696D0 (pt) | 1973-10-23 |
| DE1567132A1 (de) | 1970-07-23 |
| DE1620264A1 (de) | 1970-02-12 |
| BE679607A (en:Method) | 1966-10-17 |
| US3884933A (en) | 1975-05-20 |
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