DE2149312C3 - Thiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Nematicide und Bodeninsektizide - Google Patents
Thiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Nematicide und BodeninsektizideInfo
- Publication number
- DE2149312C3 DE2149312C3 DE2149312A DE2149312A DE2149312C3 DE 2149312 C3 DE2149312 C3 DE 2149312C3 DE 2149312 A DE2149312 A DE 2149312A DE 2149312 A DE2149312 A DE 2149312A DE 2149312 C3 DE2149312 C3 DE 2149312C3
- Authority
- DE
- Germany
- Prior art keywords
- active ingredient
- test
- soil
- preparation
- solvent
- 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.)
- Expired
Links
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title claims description 9
- 239000002689 soil Substances 0.000 title description 23
- 238000002360 preparation method Methods 0.000 title description 15
- 238000000034 method Methods 0.000 title description 5
- 239000002917 insecticide Substances 0.000 title description 2
- 239000005645 nematicide Substances 0.000 title description 2
- 239000004480 active ingredient Substances 0.000 description 63
- 239000002904 solvent Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
- 241001465754 Metazoa Species 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 241000238631 Hexapoda Species 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 241000244206 Nematoda Species 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- -1 alkali metal salts Chemical class 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 230000001069 nematicidal effect Effects 0.000 description 5
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical class OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 241000256118 Aedes aegypti Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000003197 gene knockdown Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YNWKEXMSQQUMEL-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1Cl YNWKEXMSQQUMEL-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000256113 Culicidae Species 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BAYGVMXZJBFEMB-UHFFFAOYSA-N 4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1 BAYGVMXZJBFEMB-UHFFFAOYSA-N 0.000 description 2
- 241000218475 Agrotis segetum Species 0.000 description 2
- 241000627010 Delia brassica Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000399949 Ditylenchus dipsaci Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000379510 Heterodera schachtii Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IEMNQLAXBXXIKT-UHFFFAOYSA-N 2,6-dibromo-4-(trifluoromethyl)phenol Chemical compound OC1=C(Br)C=C(C(F)(F)F)C=C1Br IEMNQLAXBXXIKT-UHFFFAOYSA-N 0.000 description 1
- ILWGCRQDVDJDIT-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)phenol Chemical compound OC1=C(Cl)C=C(C(F)(F)F)C=C1Cl ILWGCRQDVDJDIT-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241000294569 Aphelenchoides Species 0.000 description 1
- 241000134843 Aphelenchoides besseyi Species 0.000 description 1
- 241000294568 Aphelenchoides fragariae Species 0.000 description 1
- 241000680417 Aphelenchoides ritzemabosi Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 241001414892 Delia radicum Species 0.000 description 1
- 241000399934 Ditylenchus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241001442497 Globodera rostochiensis Species 0.000 description 1
- 241001480224 Heterodera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000243784 Meloidogyne arenaria Species 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001148650 Paratylenchus Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241000201377 Radopholus Species 0.000 description 1
- 241001509967 Reticulitermes flavipes Species 0.000 description 1
- 241000855013 Rotylenchus Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000201423 Xiphinema Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE789463D BE789463A (fr) | 1971-10-02 | Nouveaux esters d'acides thiophosphoriques, leur procede de preparationet leur application comme nematicides et insecticides du sol | |
| DE2149312A DE2149312C3 (de) | 1971-10-02 | 1971-10-02 | Thiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Nematicide und Bodeninsektizide |
| DD165843A DD104177A5 (cg-RX-API-DMAC10.html) | 1971-10-02 | 1972-09-22 | |
| US00292579A US3819755A (en) | 1971-10-02 | 1972-09-27 | O,o-dialkyl-o-(4-trifluoromethylphenyl)-thionophosphoric acid esters |
| BR006737/72A BR7206737D0 (pt) | 1971-10-02 | 1972-09-28 | Processo para a preparacao de esteres de acido tiofosforico e composicoes nematicidas e inseticidas do solo a base destes |
| ZA726691A ZA726691B (en) | 1971-10-02 | 1972-09-29 | Thiophosphoric acid esters,process for their use as nematocides and soil insecticides |
| NL7213244A NL7213244A (cg-RX-API-DMAC10.html) | 1971-10-02 | 1972-09-29 | |
| CH1421672A CH571531A5 (cg-RX-API-DMAC10.html) | 1971-10-02 | 1972-09-29 | |
| AT841372A AT312991B (de) | 1971-10-02 | 1972-09-29 | Nematizides und bodeninsektizides Mittel |
| JP7297257A JPS5534159B2 (cg-RX-API-DMAC10.html) | 1971-10-02 | 1972-09-29 | |
| JP47097258A JPS4840935A (cg-RX-API-DMAC10.html) | 1971-10-02 | 1972-09-29 | |
| IL40469A IL40469A0 (en) | 1971-10-02 | 1972-09-29 | Thiophosphoric acid esters,their preparation,and their use as nematocides and soil insecticides |
| DK484572AA DK129796B (da) | 1971-10-02 | 1972-09-29 | Nematodicidt og jordinsecticidt virksomme thiophosphorsyreestere. |
| IL7240468A IL40468A (en) | 1971-10-02 | 1972-09-29 | Thiophosphoric acid esters,their preparation and their use as nematocides and soil insecticides |
| IT29973/72A IT968530B (it) | 1971-10-02 | 1972-09-30 | Esteri dell acido tio fosforico procedimento per la loro prepara zione e loro impiego come nemato cidi e come insetticidi del terreno |
| FR7234813A FR2154775B1 (cg-RX-API-DMAC10.html) | 1971-10-02 | 1972-10-02 | |
| GB4534672A GB1348459A (en) | 1971-10-02 | 1972-10-02 | Thiophosphoric acid esters process for their preparation and their use as nematocides and soil insecticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2149312A DE2149312C3 (de) | 1971-10-02 | 1971-10-02 | Thiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Nematicide und Bodeninsektizide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2149312A1 DE2149312A1 (de) | 1973-04-05 |
| DE2149312B2 DE2149312B2 (de) | 1979-06-21 |
| DE2149312C3 true DE2149312C3 (de) | 1980-06-04 |
Family
ID=5821321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2149312A Expired DE2149312C3 (de) | 1971-10-02 | 1971-10-02 | Thiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Nematicide und Bodeninsektizide |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3819755A (cg-RX-API-DMAC10.html) |
| JP (2) | JPS4840935A (cg-RX-API-DMAC10.html) |
| AT (1) | AT312991B (cg-RX-API-DMAC10.html) |
| BE (1) | BE789463A (cg-RX-API-DMAC10.html) |
| BR (1) | BR7206737D0 (cg-RX-API-DMAC10.html) |
| CH (1) | CH571531A5 (cg-RX-API-DMAC10.html) |
| DD (1) | DD104177A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2149312C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK129796B (cg-RX-API-DMAC10.html) |
| FR (1) | FR2154775B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1348459A (cg-RX-API-DMAC10.html) |
| IL (2) | IL40468A (cg-RX-API-DMAC10.html) |
| IT (1) | IT968530B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7213244A (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA726691B (cg-RX-API-DMAC10.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3911122A (en) * | 1971-09-30 | 1975-10-07 | Ciba Geigy Corp | Insecticidal and acarididal substituted phenyl thiophosphoric acid esters |
| US3891728A (en) * | 1971-09-30 | 1975-06-24 | Ciba Geigy Corp | O-alkyl-S-alkyl-O-substituted phenyl-thiophosphoric acid esters |
| US4123526A (en) * | 1975-12-24 | 1978-10-31 | Stauffer Chemical Company | Thionophosphate insecticide activators |
| IL57962A0 (en) * | 1978-08-21 | 1979-12-30 | Kumiai Chemical Industry Co | Organic phosphoric ester derivatives their preparation and bacteriocidal insecticidal and miticidal compositions containing them |
| US4259510A (en) * | 1979-05-02 | 1981-03-31 | Rohm And Haas Company | Preparation of trifluoromethylphenyl nitrophenylethers |
| US4262152A (en) * | 1979-05-02 | 1981-04-14 | Rohm And Haas Company | Preparation of trifluoromethylphenyl nitrophenylethers |
| DE3037414A1 (de) * | 1980-10-03 | 1982-05-19 | Basf Ag, 6700 Ludwigshafen | 4-trifluormethylphenyl-(di)thiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| DE3201227A1 (de) * | 1982-01-16 | 1983-07-28 | Basf Ag, 6700 Ludwigshafen | 2-trifluormethylphenyl-(di)-thiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| JPS6024358U (ja) * | 1983-07-26 | 1985-02-19 | ヤンマー農機株式会社 | 静電粉体農薬散布装置 |
| JPS60144230U (ja) * | 1984-03-02 | 1985-09-25 | 日立コンデンサ株式会社 | 金属化コンデンサ |
| JP2566845B2 (ja) * | 1990-08-13 | 1996-12-25 | カルピス食品工業 株式会社 | 乳蛋白含有酸性飲料 |
| US6092620A (en) * | 1998-09-22 | 2000-07-25 | Klim; Rory | Support frame |
-
0
- BE BE789463D patent/BE789463A/xx unknown
-
1971
- 1971-10-02 DE DE2149312A patent/DE2149312C3/de not_active Expired
-
1972
- 1972-09-22 DD DD165843A patent/DD104177A5/xx unknown
- 1972-09-27 US US00292579A patent/US3819755A/en not_active Expired - Lifetime
- 1972-09-28 BR BR006737/72A patent/BR7206737D0/pt unknown
- 1972-09-29 CH CH1421672A patent/CH571531A5/xx not_active IP Right Cessation
- 1972-09-29 AT AT841372A patent/AT312991B/de not_active IP Right Cessation
- 1972-09-29 ZA ZA726691A patent/ZA726691B/xx unknown
- 1972-09-29 JP JP47097258A patent/JPS4840935A/ja active Pending
- 1972-09-29 DK DK484572AA patent/DK129796B/da unknown
- 1972-09-29 NL NL7213244A patent/NL7213244A/xx not_active Application Discontinuation
- 1972-09-29 JP JP7297257A patent/JPS5534159B2/ja not_active Expired
- 1972-09-29 IL IL7240468A patent/IL40468A/xx unknown
- 1972-09-29 IL IL40469A patent/IL40469A0/xx unknown
- 1972-09-30 IT IT29973/72A patent/IT968530B/it active
- 1972-10-02 FR FR7234813A patent/FR2154775B1/fr not_active Expired
- 1972-10-02 GB GB4534672A patent/GB1348459A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD104177A5 (cg-RX-API-DMAC10.html) | 1974-03-05 |
| FR2154775B1 (cg-RX-API-DMAC10.html) | 1976-05-21 |
| JPS4840935A (cg-RX-API-DMAC10.html) | 1973-06-15 |
| IL40468A0 (en) | 1972-11-28 |
| GB1348459A (en) | 1974-03-20 |
| AT312991B (de) | 1974-01-25 |
| JPS5534159B2 (cg-RX-API-DMAC10.html) | 1980-09-04 |
| NL7213244A (cg-RX-API-DMAC10.html) | 1973-04-04 |
| CH571531A5 (cg-RX-API-DMAC10.html) | 1976-01-15 |
| DE2149312A1 (de) | 1973-04-05 |
| DK129796B (da) | 1974-11-18 |
| IL40469A0 (en) | 1972-11-28 |
| IT968530B (it) | 1974-03-20 |
| DE2149312B2 (de) | 1979-06-21 |
| BR7206737D0 (pt) | 1973-08-23 |
| DK129796C (cg-RX-API-DMAC10.html) | 1975-04-28 |
| JPS4840751A (cg-RX-API-DMAC10.html) | 1973-06-15 |
| ZA726691B (en) | 1973-06-27 |
| IL40468A (en) | 1975-06-25 |
| US3819755A (en) | 1974-06-25 |
| BE789463A (fr) | 1973-03-29 |
| FR2154775A1 (cg-RX-API-DMAC10.html) | 1973-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete renunciation |