IL40476A - O,s-dialkyl-o-phenyl thiophosphoric acid esters,their manufacture and their use in pest control - Google Patents
O,s-dialkyl-o-phenyl thiophosphoric acid esters,their manufacture and their use in pest controlInfo
- Publication number
- IL40476A IL40476A IL40476A IL4047672A IL40476A IL 40476 A IL40476 A IL 40476A IL 40476 A IL40476 A IL 40476A IL 4047672 A IL4047672 A IL 4047672A IL 40476 A IL40476 A IL 40476A
- Authority
- IL
- Israel
- Prior art keywords
- parts
- formula
- compound according
- manufacture
- active
- Prior art date
Links
- 241000607479 Yersinia pestis Species 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 241000238876 Acari Species 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003415 peat Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 1
- 229940031826 phenolate Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 12
- 239000013543 active substance Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- -1 chlorobenzene nitriles Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000019993 champagne Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 230000001473 noxious effect Effects 0.000 description 2
- 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 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- FKTNGDYCQLRWLV-UHFFFAOYSA-N 3-ethyl-N-propylpentan-3-amine Chemical class CCCNC(CC)(CC)CC FKTNGDYCQLRWLV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000994522 Anthrenus flavipes Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001124134 Chrysomelidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000576083 Ionidae Species 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 241000041821 Necrobia Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical group O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- DYFIVHNTJCEYOT-UHFFFAOYSA-L disodium;1,2-dibutylnaphthalene;sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O.C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 DYFIVHNTJCEYOT-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- HZZOEADXZLYIHG-UHFFFAOYSA-N magnesiomagnesium Chemical compound [Mg][Mg] HZZOEADXZLYIHG-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000013102 re-test Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene 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)
Description
ona Hew enyl thiophoaphoric acid their manufacture and their use in pest control 38479 t This invention relates to acid esters of the formula wherein X is hydrogen and Y chlorine or X is chlorine and Y Another subject is the manufacture of the of formula I and their use as active ingredients in pesticidal especially ihsecticidal The compounds of formula I are most generally disclosed in French Patents and 1 567 corresponds o Israel patent specification The DOS discloses and The instant compounds have a similar spectrum of activity but are surprisingly more A disclosure of even more closely related compounds such as the and acid ester is to be found in the DOS corresponds to Israel patent ification Accordingly the are selection out of the latter and show surprisingly superior activities on at least the same toxicity level as the closest known especially with respect to their initial effect towards cotton The new thiophosphoric acid phenylesters may be prepared according to known processes such acid j In the above formulae Me represents an alkali particularly or ammonium or R stands for a especially methyl or ethyl and Hal is a halogen atom such as iodine especially however chlorine or As acid binding agents there may be used tertiary tria kylamines pyridine or dialkylanilines also suitable are inorganic bases such as carbonates and bicarbonates of alkali and alkaline earth Depending on conditions it may be desirable in order to enhance the yield or reduce the duration of the reaction to use a catalyst as copper or copper he processes la 3b are out at a reaction temperature between and at normal pressure and in solvents or diluents inert to the Suitable as inert solvents or diluents are for example ethers and ethereal compounds such as diethyl dipropyl amides such as ic acid aliphatic and aromatic which may be halogenated particularly chlorobenzene nitriles such as aceton For processes 3a and 3b alcohols such as or isoprupanol are uncfe of I broad insect and cidal activity against plantp thogenic peats being compounds above all as contact poison and thus can used for the control of all velopment stages such as pupae and adults of chewing d boring posts and Noxious viduals of this kind are to be found in the field of forest and stored products Most results how ver are achieved against pests noxious to cotton and this connection the following families of insects and acarina must be Chrysomel idae ionidae enebr idae Ilyponomeutidae Lymantri threut i dae ranychidae insecticidal acaricidal effects can bo broadened and matched to given cumstances by the addition of other insecticides or aca icides Such additional active ingredients may be selected from the group of nitrophenols and derivatives chlorinated pyrethr inlike compounds and amid especially formamidines a most valuable of which is 1 2 i The compoundjof formula I may be used as active or together with suitable carriers Suitable carriers and additives may be solid or liquid and correspond to he substances in Lion as wetting ad binders application the instant m be processed to ventionally formulated preparations as they are commonly application te may be used as concentrates or lutions according to the of such parations are in solid scattering agents or granules in liquid concentrates of active ingredient dispersible in wettable pastes or emulsifiabie solutions above pesticidal preparations may be manufactured in known manner by intimately mixing grinding the active dient with the suitable optionally with the addition of dispersants or solvents which are inert towards the active To manufacture dusts and scattering the active substance mixed according to known methods with solid Suitable carriers for ground precipitated alkaline earth and potassium aluminum silicates and and magnesium magnesium ground for example ammonium ammonium ground vegetable as corn bark nutshell cellulose residues of plant activated charcoal granular formulations can be easily manufactured according to known To these mixtures may also be added stabilizers for the active ingredient anionic and cationic surface active which for example improve the adhesion of the active ingredients on plants or parts of plants and ensure a better wettability and dispersibility Suitable additives are for example cellulose derivatives carboxymethyl hydroxyethyl glycol ethers of monoalkyl and dialkyl phenols having 5 to 15 ethylene oxide radicals per molecule and 8 to 9 carbon atoms in the alkyl lignin sulfonic their alkali metal and alkaline earth metal polyethylene glycol ethers fatty alcohol polyethylene glycol ethers having 5 to 20 ethylene oxide radicals per molecule and 8 to 18 carbon atoms in the fatty alcohol condensation products of ethylene polyvinyl pyrrolidones polyvinyl condensation products of urea and and also latex The concentrates of the active substance wettable pastes and emulsifiable are agents which can be diluted with water to any concentration They consist of active optionally additives which stabilize the active substance and agents silicone optionally Suitable additives are well known in the formulation technique and the manufacture of the concentrates is achieved by known I dissolved in a suitable organic solvents or in Such solvents are well known in the formulation The content of active substance in the above described prepara tions is between to and most preferably between 2 and In this connection it should he that if the application is carried out from aircraft or with some other suitable it is possible to of up to or even pure active The application rate of active ingredient on the other hand is as a rule about to kg per active substancesof formula I for be formulated as Dusts The following substances are used to manufacture a and 5 parts of active ingredient 95 parts of talcum 2 parts of ingredient 1 part of highly disperse silica 97 parts of The active ingredient is mixed with the carriers and Granules The following substances are used to produce 5 parts of active ingredient parts of epichlorohydrin parts of cetyl polyglycol ether parts of polyethylene glycol 91 parts of kaolin size The active substance is with and dissolved with 6 parts of the polyethy glycol and cetyl polyglycol ether then The thus obtained solution is sprayed on to and the acetone subsequently evaporated in lettable The following constituents are used for the preparation of and a and a 40 parts of active substance 5 parts of sodium lignin sulphonate 1 part of sodium dibuty halene sulplionatc parts of silica 25 parts of active substance parts of lignin parts of Champagne cellulose ture parts of sodium dibutyl naphthalene sulphate parts of silica acid parts of Champagne chalk parts of 25 parts of active substance parts of isooctylphcno parts of Champagne parts of sodium aluminium silicate q parts of 46 parts of kaolin 10 parts of active ingredient 3 parts of a mixture of the sodium salts of saturated fatty alcohol sulphates 5 parts of naphthalenesttlphonic condensate 82 parts of The active ingredient is intimately in suitable with the the mixture being then ground in an appropriate mill and Wettable powders are obtained which can be diluted with water to give suspensions of any desired The following substances are used to produce a a and a emulsifiable 10 parts of active ingredient parts of epoxidised vegetable oil parts of a combination emulsifier consistingof fatty alcohol polyglycol ether and sulphonate calcium salt 40 parts of parts of 25 parts of active ingredient parts of epoxidised vegetable oil 10 parts of an alcohol polyglycol ether mixture 5 parts of dimethylformamide parts of parte of calcium 20 parts of cyclohexanone 20 parts of xylene From these concentrates it is possible to by dilution with emulsions of any desired The fallowing substances are used to ure a and 5 parts of active ingredient 1 part of epichlorohydrin 94 parts of petrol range 95 parts of active ingredient 5 parts of epichlorohydrin following examples illustrate the and testing of the compound according to the present Example 1 g were dissolved in 150 ml benzene and g triethylamine were then At g of were added dropwise with continuous Stirring was then continued for 12 hours at room The mixture was washed with solution and water and dried over anhydrous sodium The benzene was distilled off and the residue purified by distillation 49 g of the ester of the formula 20 was obtained with a refractive index The compound of the formula was made in analogous 2 Pott d cotton and tobacco plants respectively were 125 of active ingredient in the form of si er the coating had the treated plants were w t third instar larvae of lleliothis The tests were running under greenhouse conditions at and 60s relative humidity Assessments to evaluate the initial effect of the ate acitivity of the active ingredient were carried out 24 and 48 hours after the infestation of the plants with the Lest plan i h the individuals 2 and 8 days after the of the active test was nd compounds C o Y A test analogous to that described under was accomplished by spraying the plants with 500 ppm of active ingredient in the form of an aqueous Assessments to evaluate the initial effect of the activity over a prolonged period were carried out as the coated test plants were infested with the test individuals 8 days after the application of the active ingredient and checked 4 and 24 hours after the compoun s In this test too compounds I and III clearly show a better initial vulgaris had an infested of leaf a mass culture of Totranychus urticae placed on them 12 re test for the acaricidal occupying mobile were sprayed with the emulsified testing preparation Ί p n Γ L In this test too I and clearly show a better initial vulgaris had an infested piece of a mass culture of urticae on 12 t test for the occupying were sprayed with the testing preparation i a chromatography atomiser so that the sprayed layer did not run The number of living and dead adults and eggs were evaluated after 7 days under a stereoscopic microscope the result expressed in During the the treated plants were kept in greenhouse compartments at 2 The evaluation was of the test proved qood activity of the active 4 Λ dust on a base of talcum and containing active ingredient was applied to filter paper in concentrations of 2 and of active substance per m Onto each of the treated substrates were applied 5 Necrobia Rhyzoperta Anthrenus vorax and Tribolium confusum individuals respec Lively Evaluation took place 24 hours Test compounds were same as set forth in Example insufficientOCRQuality
Claims (7)
1. A compound of the formula wherein X is hydrogen and Y chlorine or X is chlorine and Y bromine . compound according to claim 1 , 1» /
CI
3. The compound according to claim 1
4. A proceea for the preparation of a compound according claim 1 which compriaea reooting, in the presence of an id binding agent, a halophosphate of the formula with a phenol of the formula or with a phenolate of the formul wherein X and Y have the meaninga given in olaim 1 and Me ia an alkali metal, ammonium or alkylammonium group.
5. A peat control agent which cornprioes aa active component a compound according to any of claima 1 to 3 together with suitable carriers and/or other additivea.
6. A method of pest control against insects and representatives of the order Acarina which comprises applying to the said pests a pesticidally effective amount of a compoun according to any of claims 1 to 3.
7. A method according to claim 6 which comprises controlling insects harmful to cotton and vegetables.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1485571A CH570762A5 (en) | 1971-10-12 | 1971-10-12 | O-ethyl-s-propyl-o-(halophenyl) thiophosphates - with insecticidal and acaricidal activity |
CH1278072 | 1972-08-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
IL40476A0 IL40476A0 (en) | 1972-12-29 |
IL40476A true IL40476A (en) | 1976-02-29 |
Family
ID=25710971
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL40476A IL40476A (en) | 1971-10-12 | 1972-10-02 | O,s-dialkyl-o-phenyl thiophosphoric acid esters,their manufacture and their use in pest control |
Country Status (19)
Country | Link |
---|---|
JP (1) | JPS527056B2 (en) |
AR (1) | AR195503A1 (en) |
BE (1) | BE789937A (en) |
BG (1) | BG19089A3 (en) |
CA (1) | CA1051915A (en) |
CY (1) | CY887A (en) |
DD (1) | DD101541A5 (en) |
DE (1) | DE2249462A1 (en) |
ES (1) | ES407515A1 (en) |
FR (1) | FR2156230B1 (en) |
GB (1) | GB1417116A (en) |
HK (1) | HK6277A (en) |
IL (1) | IL40476A (en) |
IT (1) | IT986856B (en) |
KE (1) | KE2694A (en) |
MY (1) | MY7700160A (en) |
NL (1) | NL161157C (en) |
OA (1) | OA04201A (en) |
SU (1) | SU673138A3 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4223026A (en) * | 1979-03-23 | 1980-09-16 | The Dow Chemical Company | Insecticidal synergistic mixture of O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate and O-ethyl O-(2-chloro-4-bromophenyl)-S-n-propyl phosphorothioate |
JPH04148180A (en) * | 1990-10-05 | 1992-05-21 | Hoshizaki Electric Co Ltd | Both left-and-right opening door structure for box body |
DE102007045955A1 (en) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Active agent combination, useful e.g. for combating animal pests and treating seeds of transgenic plants, comprises substituted amino-furan-2-one compound and at least one compound e.g. diazinon, isoxathion, carbofuran or aldicarb |
EP2127522A1 (en) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Active-agent combinations with insecticidal and acaricidal properties |
-
1972
- 1972-09-15 NL NL7212564.A patent/NL161157C/en not_active IP Right Cessation
- 1972-10-02 IL IL40476A patent/IL40476A/en unknown
- 1972-10-04 CA CA153,177A patent/CA1051915A/en not_active Expired
- 1972-10-09 DE DE2249462A patent/DE2249462A1/en active Granted
- 1972-10-10 BG BG021584A patent/BG19089A3/en unknown
- 1972-10-10 AR AR244550A patent/AR195503A1/en active
- 1972-10-11 SU SU721837120A patent/SU673138A3/en active
- 1972-10-11 BE BE789937D patent/BE789937A/en not_active IP Right Cessation
- 1972-10-11 DD DD166158A patent/DD101541A5/xx unknown
- 1972-10-11 CY CY887A patent/CY887A/en unknown
- 1972-10-11 IT IT30361/72A patent/IT986856B/en active
- 1972-10-11 FR FR7235921A patent/FR2156230B1/fr not_active Expired
- 1972-10-11 GB GB4692772A patent/GB1417116A/en not_active Expired
- 1972-10-11 ES ES407515A patent/ES407515A1/en not_active Expired
- 1972-10-12 JP JP47102314A patent/JPS527056B2/ja not_active Expired
- 1972-10-12 OA OA54722A patent/OA04201A/en unknown
-
1977
- 1977-01-26 KE KE2694A patent/KE2694A/en unknown
- 1977-01-27 HK HK62/77A patent/HK6277A/en unknown
- 1977-12-30 MY MY160/77A patent/MY7700160A/en unknown
Also Published As
Publication number | Publication date |
---|---|
OA04201A (en) | 1979-12-31 |
DE2249462A1 (en) | 1973-04-19 |
CA1051915A (en) | 1979-04-03 |
AR195503A1 (en) | 1973-10-15 |
JPS527056B2 (en) | 1977-02-26 |
FR2156230B1 (en) | 1975-11-21 |
SU673138A3 (en) | 1979-07-05 |
CY887A (en) | 1977-03-18 |
FR2156230A1 (en) | 1973-05-25 |
GB1417116A (en) | 1975-12-10 |
NL7212564A (en) | 1973-04-16 |
IT986856B (en) | 1975-01-30 |
BG19089A3 (en) | 1975-04-30 |
HK6277A (en) | 1977-02-04 |
DE2249462B2 (en) | 1975-10-16 |
IL40476A0 (en) | 1972-12-29 |
ES407515A1 (en) | 1976-01-16 |
KE2694A (en) | 1977-02-11 |
NL161157C (en) | 1980-01-15 |
NL161157B (en) | 1979-08-15 |
MY7700160A (en) | 1977-12-31 |
BE789937A (en) | 1973-04-11 |
JPS4844434A (en) | 1973-06-26 |
DD101541A5 (en) | 1973-11-12 |
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