DE1567199A1 - Sulfitester,Verfahren zu deren Herstellung und insektizide Mittel,die diese enthalten - Google Patents
Sulfitester,Verfahren zu deren Herstellung und insektizide Mittel,die diese enthaltenInfo
- Publication number
- DE1567199A1 DE1567199A1 DE19621567199 DE1567199A DE1567199A1 DE 1567199 A1 DE1567199 A1 DE 1567199A1 DE 19621567199 DE19621567199 DE 19621567199 DE 1567199 A DE1567199 A DE 1567199A DE 1567199 A1 DE1567199 A1 DE 1567199A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfite
- tert
- propargyl
- group
- butynyl
- 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.)
- Granted
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 title claims description 48
- 238000002360 preparation method Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 6
- 239000002917 insecticide Substances 0.000 title claims description 4
- -1 sulfite ester Chemical class 0.000 claims description 49
- 239000004480 active ingredient Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- WCTKUENARPWTAY-UHFFFAOYSA-N ac1l9mss Chemical compound OS(Cl)=O WCTKUENARPWTAY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- XFQXBPAWGJCSRO-UHFFFAOYSA-N CCC(C)(C)C(C=C1)=CC=C1OC(CC#C)COS(O)=O Chemical compound CCC(C)(C)C(C=C1)=CC=C1OC(CC#C)COS(O)=O XFQXBPAWGJCSRO-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 2
- 125000004999 nitroaryl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 239000000126 substance Substances 0.000 description 32
- 241000238876 Acari Species 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 23
- 238000012360 testing method Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000006378 damage Effects 0.000 description 11
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 8
- 244000046052 Phaseolus vulgaris Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
- CGXHPTWUDYBMDB-UHFFFAOYSA-N (2-chloro-3-methylbutyl) hydrogen sulfite Chemical compound CC(C)C(COS(=O)O)Cl CGXHPTWUDYBMDB-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#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
- UQXZGMVSUWSPOG-UHFFFAOYSA-N 2-phenoxypropan-2-yl hydrogen sulfite Chemical compound CC(C)(OC1=CC=CC=C1)OS(O)=O UQXZGMVSUWSPOG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- NNQWSOSXFWZTHN-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC=C1OC(C)(CCC#C)OS(O)=O Chemical compound CC(C)(C)C(C=C1)=CC=C1OC(C)(CCC#C)OS(O)=O NNQWSOSXFWZTHN-UHFFFAOYSA-N 0.000 description 1
- CEZYSKSJAYADIF-UHFFFAOYSA-N CC(C)OC(C)(C)OS(O)=O Chemical compound CC(C)OC(C)(C)OS(O)=O CEZYSKSJAYADIF-UHFFFAOYSA-N 0.000 description 1
- YJLFKZHORHAQEH-UHFFFAOYSA-N CC(CCC#C)(OC1=CC=C(C)C=C1)OS(O)=O Chemical compound CC(CCC#C)(OC1=CC=C(C)C=C1)OS(O)=O YJLFKZHORHAQEH-UHFFFAOYSA-N 0.000 description 1
- WJLZEXUTCITNSO-UHFFFAOYSA-N CC(CCOC1=CC=CC=C1)OS(O)=O Chemical compound CC(CCOC1=CC=CC=C1)OS(O)=O WJLZEXUTCITNSO-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 238000001856 aerosol method Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- SFZOVQBYQURCQJ-UHFFFAOYSA-N butan-2-yl hydrogen sulfite Chemical compound CCC(C)OS(O)=O SFZOVQBYQURCQJ-UHFFFAOYSA-N 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- FEYYOXFAQQJEIG-UHFFFAOYSA-N dibutyl sulfite Chemical compound CCCCOS(=O)OCCCC FEYYOXFAQQJEIG-UHFFFAOYSA-N 0.000 description 1
- NVJBFARDFTXOTO-UHFFFAOYSA-N diethyl sulfite Chemical compound CCOS(=O)OCC NVJBFARDFTXOTO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- QAMPNIXQLSTWGU-UHFFFAOYSA-M propyl sulfite Chemical compound CCCOS([O-])=O QAMPNIXQLSTWGU-UHFFFAOYSA-M 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C301/00—Esters of sulfurous acid
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C301/00—Esters of sulfurous acid
- C07C301/02—Esters of sulfurous acid having sulfite groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13174161A | 1961-08-16 | 1961-08-16 | |
| US13174161 | 1961-08-16 | ||
| DEU0008999 | 1962-05-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1567199A1 true DE1567199A1 (de) | 1970-01-29 |
| DE1567199C DE1567199C (enrdf_load_stackoverflow) | 1973-05-24 |
Family
ID=22450817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621567199 Granted DE1567199A1 (de) | 1961-08-16 | 1962-05-25 | Sulfitester,Verfahren zu deren Herstellung und insektizide Mittel,die diese enthalten |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE619254A (enrdf_load_stackoverflow) |
| CH (1) | CH408907A (enrdf_load_stackoverflow) |
| DE (1) | DE1567199A1 (enrdf_load_stackoverflow) |
| GB (1) | GB969091A (enrdf_load_stackoverflow) |
| LU (1) | LU41941A1 (enrdf_load_stackoverflow) |
| NL (1) | NL121168C (enrdf_load_stackoverflow) |
-
1962
- 1962-05-25 DE DE19621567199 patent/DE1567199A1/de active Granted
- 1962-06-15 GB GB2302762A patent/GB969091A/en not_active Expired
- 1962-06-25 LU LU41941D patent/LU41941A1/xx unknown
- 1962-07-11 NL NL280837A patent/NL121168C/xx active
- 1962-08-03 CH CH933362A patent/CH408907A/fr unknown
- 1962-10-15 BE BE619254A patent/BE619254A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL121168C (enrdf_load_stackoverflow) | 1966-09-15 |
| CH408907A (fr) | 1966-03-15 |
| LU41941A1 (enrdf_load_stackoverflow) | 1962-08-25 |
| BE619254A (enrdf_load_stackoverflow) | 1962-10-15 |
| NL280837A (enrdf_load_stackoverflow) | 1964-12-10 |
| GB969091A (en) | 1964-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1567205A1 (de) | Neue Sulfitester und ihre Verwendung als acaricide Mittel | |
| DE2407024A1 (de) | Zur schaedlingsbekaempfung geeignete cyclopropanderivate und verfahren zu ihrer herstellung | |
| DE1068699B (de) | Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphorsäureestern | |
| DE1166790B (de) | Verfahren zur Herstellung von insektizid wirksamem O, O-Dimethyl-O-(3-methyl-4-nitrophenyl)-thionophosphorsaeureester | |
| DE1567199A1 (de) | Sulfitester,Verfahren zu deren Herstellung und insektizide Mittel,die diese enthalten | |
| DE1443933C2 (de) | Thiocyano-phenyl-isothiocyanate und ihre Verwendung als Schädlingsbekämpfungsmittel | |
| DE2008001A1 (de) | Phosphorylierte Äthylendiamine, ihre Herstellung und Verwendung | |
| DE1567199C (enrdf_load_stackoverflow) | ||
| DE1567198C (de) | Schwefligsaurephenyl phenoxyalkyl ester und ihre Verwendung A,5\m Uuwoyal Uic , New Yolk, N Y (V St A) | |
| DE2023791A1 (de) | Epoxidierte Geranylester und deren Verwendung in Insektenbekämpfungsmitteln | |
| DE2061133A1 (de) | Pestizide Verbindung,Verfahren zu ihrer Herstellung und Verwendung | |
| DE1148806B (de) | Schaedlingsbekaempfungsmittel | |
| DE1567199B (de) | Sulfitester, Verfahren zu deren Herstellung und insektizide Mittel, die diese enthalten | |
| DE1181200B (de) | Verfahren zur Herstellung des N-Mono-methylamids der O, O-Di-(ª-fluoraethyl)-dithiophosphorylessigsaeure | |
| DE2608506C2 (de) | Neue 0,0-Dialkyl-(di)thiophosphorsäureester, ihre Herstellung sowie ihre Verwendung in insektiziden und akariziden Zusammensetzungen | |
| DE1089381B (de) | Verfahren zur Herstellung unsymmetrischer Diester der ª-Oxy-ª, ª, ª-trichloraethyl-phosphonsaeure | |
| DE1259331B (de) | Verfahren zur Herstellung von Dithiophosphorsaeureestern | |
| DE1567205C3 (de) | Ester der schwefeligen Säure und ihre Verwendung als Insektizide und Acarizide | |
| DE1493276C3 (de) | Sulfitdiester, Verfahren zu deren Herstellung und ihrer Verwendung | |
| DE1643706C (de) | Thinonophosphon(or)saureester | |
| DE1567198B1 (de) | Schwefligsaeurephenyl-phenoxalkylester und ihre Verwendung | |
| DE1181978B (de) | Mittel zur Bekaempfung von Arthropoden, Mollusken und Fischen | |
| DE974569C (de) | Schaedlingsbekaempfungsmittel | |
| DE1187848B (de) | Insektizides und akarizides Mittel | |
| DE2015854C3 (de) | Phenoxy acethylhydroxamsäurederivate und ihre Verwendung als Fungizide, Algizide und Molluskizide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) |