DE1567135A1 - Nematicide Mittel - Google Patents
Nematicide MittelInfo
- Publication number
- DE1567135A1 DE1567135A1 DE19661567135 DE1567135A DE1567135A1 DE 1567135 A1 DE1567135 A1 DE 1567135A1 DE 19661567135 DE19661567135 DE 19661567135 DE 1567135 A DE1567135 A DE 1567135A DE 1567135 A1 DE1567135 A1 DE 1567135A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- dichlorophenyl
- content
- parts
- carbon atoms
- 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
- 239000005645 nematicide Substances 0.000 title claims description 12
- -1 2,4-dichlorophenyl- Chemical group 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 230000001069 nematicidal effect Effects 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000002689 soil Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 235000012343 cottonseed oil Nutrition 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003871 sulfonates Chemical class 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- LEBRQTODERLAMO-UHFFFAOYSA-N ethoxy ethanesulfonate Chemical compound CCOOS(=O)(=O)CC LEBRQTODERLAMO-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 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 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical group CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RVEZEHWSFGFPAW-UHFFFAOYSA-N (2,4-dichlorophenyl) ethenesulfonate Chemical compound ClC1=CC=C(OS(=O)(=O)C=C)C(Cl)=C1 RVEZEHWSFGFPAW-UHFFFAOYSA-N 0.000 description 1
- ICWLIIWNOCWYBG-UHFFFAOYSA-N (4-chloro-2-fluorophenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(Cl)C=C1F ICWLIIWNOCWYBG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- HMPHJJBZKIZRHG-UHFFFAOYSA-M chloromethanesulfonate Chemical compound [O-]S(=O)(=O)CCl HMPHJJBZKIZRHG-UHFFFAOYSA-M 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-M propane-1-sulfonate Chemical compound CCCS([O-])(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-M 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/68—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US475877A US3395232A (en) | 1965-07-29 | 1965-07-29 | Soil-borne nematode control by seeds treated with 2, 4-dihalophenyl ester of lower alkane and haloalkane sulfonic acids |
| US475851A US3395231A (en) | 1965-07-29 | 1965-07-29 | Soil-borne nematode control by seeds treated with 2-chloro-4-halophenyl esters of alkoxyethanesulfonic acids |
| US475842A US3401222A (en) | 1965-07-29 | 1965-07-29 | Nematocidal 2, 4-dihalophenyl esters of ethanesulfonic acid ethers and alcohols |
| US475862A US3346613A (en) | 1965-07-29 | 1965-07-29 | 2, 4-dihalophenyl esters of lower alkane-and haloalkane-sulfonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1567135A1 true DE1567135A1 (de) | 1970-08-27 |
Family
ID=27504206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661567135 Pending DE1567135A1 (de) | 1965-07-29 | 1966-07-27 | Nematicide Mittel |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US3395231A (en, 2012) |
| BE (1) | BE684699A (en, 2012) |
| BR (1) | BR6681614D0 (en, 2012) |
| CH (1) | CH489205A (en, 2012) |
| DE (1) | DE1567135A1 (en, 2012) |
| GB (1) | GB1147035A (en, 2012) |
| NL (1) | NL6610620A (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3395231A (en) * | 1965-07-29 | 1968-07-30 | Shell Oil Co | Soil-borne nematode control by seeds treated with 2-chloro-4-halophenyl esters of alkoxyethanesulfonic acids |
| US3463803A (en) * | 1966-10-28 | 1969-08-26 | Chemagro Corp | Polyhaloethyl and polyhalovinyl sulfinate and thiosulfinate esters |
| US3764698A (en) * | 1970-05-21 | 1973-10-09 | Monsanto Co | Insecticides compositions and methods employing 3,4, substituted phenylmethylsulfinates |
| US3978228A (en) * | 1971-12-13 | 1976-08-31 | Kumiai Chemical Industry Co., Ltd. | Method for killing noxious fungi in plants using dihalo sulfonates |
| CH580905A5 (en, 2012) * | 1973-12-21 | 1976-10-29 | Ciba Geigy Ag | |
| DE19932317A1 (de) * | 1999-07-10 | 2001-01-11 | Merck Patent Gmbh | Verfahren zur Herstellung von Lithiumkomplexsalzen zur Anwendung in elektrochemischen Zellen |
| US6599866B2 (en) * | 2001-04-20 | 2003-07-29 | Exxonmobil Research And Engineering Company | Servo valve erosion inhibited aircraft hydraulic fluids |
| US6764983B1 (en) * | 2001-06-29 | 2004-07-20 | Iowa State University Research Foundation | Antioxidant compositions and industrial fluids containing same |
| TWI730297B (zh) * | 2018-02-27 | 2021-06-11 | 日商組合化學工業股份有限公司 | 巰基酚化合物的製造方法及巰基酚化合物的中間體 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2474350A (en) * | 1944-06-24 | 1949-06-28 | Pittsburgh Plate Glass Co | Polysulfone resin plasticized with ester of organic sulfonic acid |
| US2782217A (en) * | 1953-01-07 | 1957-02-19 | Monsanto Chemicals | Isononylphenyl-nu-octane sulfonate |
| US2728788A (en) * | 1953-01-28 | 1955-12-27 | Du Pont | Process for preparing aromatic sulfonic esters of branched chain aliphatic alcohols |
| GB824853A (en) * | 1956-03-29 | 1959-12-09 | Wellcome Found | Improvements in and relating to quaternary ammonium compounds and the preparation thereof |
| US2894971A (en) * | 1957-04-08 | 1959-07-14 | Jacques G O'rear | Polyfluoroalkyl p-toluenesulfonates |
| US3021258A (en) * | 1958-10-06 | 1962-02-13 | Union Carbide Corp | Diphenyl sulfide nematocide |
| NL286074A (en, 2012) * | 1961-12-01 | |||
| US3395231A (en) * | 1965-07-29 | 1968-07-30 | Shell Oil Co | Soil-borne nematode control by seeds treated with 2-chloro-4-halophenyl esters of alkoxyethanesulfonic acids |
-
1965
- 1965-07-29 US US475851A patent/US3395231A/en not_active Expired - Lifetime
- 1965-07-29 US US475842A patent/US3401222A/en not_active Expired - Lifetime
- 1965-07-29 US US475877A patent/US3395232A/en not_active Expired - Lifetime
- 1965-07-29 US US475862A patent/US3346613A/en not_active Expired - Lifetime
-
1966
- 1966-07-27 GB GB33786/66A patent/GB1147035A/en not_active Expired
- 1966-07-27 CH CH1084766A patent/CH489205A/de unknown
- 1966-07-27 BR BR181614/66A patent/BR6681614D0/pt unknown
- 1966-07-27 DE DE19661567135 patent/DE1567135A1/de active Pending
- 1966-07-28 BE BE684699D patent/BE684699A/xx unknown
- 1966-07-28 NL NL6610620A patent/NL6610620A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3401222A (en) | 1968-09-10 |
| US3346613A (en) | 1967-10-10 |
| BR6681614D0 (pt) | 1973-12-26 |
| CH489205A (de) | 1970-04-30 |
| US3395232A (en) | 1968-07-30 |
| GB1147035A (en) | 1969-04-02 |
| NL6610620A (en, 2012) | 1967-01-30 |
| US3395231A (en) | 1968-07-30 |
| BE684699A (en, 2012) | 1967-01-30 |
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